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From Rock Bottom to Tech Leadership with Ray Freeman | Ep056
Episode Information Show Notes The Week That Changed EverythingRay Freeman’s tech career includes a chapter most people would rather forget. After the 2008 financial crisis, Ray lost his job, his wife lost hers, and their six-bedroom Houston house became a financial prison. Eventually, Ray spent a week sleeping in his car while working contract IT jobs. Today, Ray is President and Chief Strategy Officer of RTS Premier Solutions, serving government agencies with AI and cybersecurity solutions. His story isn’t about avoiding failure, it’s about what happens when you refuse to stay down. What Makes This Episode DifferentRay doesn’t tell the sanitized version of his career. He shares the real story: blowing through money faster than he made it, losing everything in five days, and the humbling experience of living out of his car with a George Foreman grill and a rice cooker from Goodwill. But he also shares how those experiences built the resilience, communication skills, and leadership mindset that drive his success today. You’ll hear about getting fired from AT&T for challenging leadership and then being called back by the CTO who vindicated him completely. Key TakeawaysOn Building Confidence:Ray discovered he was smart by accident. After struggling in traditional school, he took Microsoft certification exams on a whim and scored perfect. That moment changed everything. He learned that finding the right way to learn matters more than fitting into someone else’s system. On Resilience:When Ray lost everything, he didn’t call for help. He bought a styrofoam cooler, found a Dollar General, and figured out how to survive. One week later, he had his first paycheck and could rent an apartment. The experience taught him that survival builds character. On Leadership:Ray got fired from AT&T for going over his manager’s head to warn about a critical infrastructure problem. Weeks later, the CTO called him back, saw the problem immediately, and gave Ray’s company a contract. That experience taught Ray to speak truth to power, no matter the personal cost. On Communication:Ray studied DISC and Emergenetics, psychometric assessments that taught him to recognize how people think and communicate. He learned to modify his tone, pace, posture, and words based on his audience. This skill became the foundation for his ability to simplify complex technical problems for executives. On Goal Setting:When Ray was sleeping in his car, he broke survival into daily goals. Make it to Monday. Get through the week. Get the first paycheck. Find an apartment. This approach of breaking massive goals into manageable chunks became a career skill that serves him to this day. On Business Ownership:Ray used to think owning a business meant doing all the work himself. Learning that business ownership means assembling people, processes, and tools not doing everything personally, transformed how he thinks about scaling and creating opportunities for others. About Ray FreemanRay Freeman is President and CSO of RTS Premier Solutions and co-owner of Win-Win Operations. With over 20 years in technology and a background that includes music production with major artists, Ray brings a unique perspective to tech leadership. His journey from sleeping in his car to leading government technology contracts proves that setbacks don’t define your career, your response to them does. Connect with Ray on LinkedIn or learn more about RTS Premier Solutions. Listen & SubscribeCareer Downloads releases new episodes every week. Subscribe on your favorite podcast platform and never miss a conversation. Visit careerdownloads.com for more episodes and resources. TranscriptionManuel Martinez: Welcome everyone, my name is Manuel Martinez and this is another episode of Career Downloads. For each episode I basically hit the refresh button, bring on a different guest to learn more about their background and their experiences to help you uncover any actionable advice that you can use as you’re managing your own career. For today’s episode I have with me Ray Freeman. He and I have met at a couple different networking events. We talked a little bit about his career. He’s got some very interesting stories and even inspiring, just understanding the different things that people go through. This one’s gonna be really fun for me and hopefully, you know – like I mentioned, inspirational for everybody else. Ray is very open and he’s gonna tell us about some of the struggles and everybody always likes to kind of talk about the successes but he’s very interested in talking about some of the challenges that happened along the way so that you can go ahead and hopefully relate to them or like I mentioned get a little bit of inspiration. So with that I’ll go ahead and introduce Ray. Ray Freeman: Thanks for having me. Manuel Martinez: I appreciate you coming on. It’s been interesting and fun talking to you, getting to know a little bit more about not only what you’re doing now but just what it took to get there. Ray Freeman: Yes, yes. Manuel Martinez: And if you don’t mind just so that people get in a sense of who Ray is now, tell me kind of what your current role is and some of the responsibilities of what it is that you do for this role. Ray Freeman: Sure, sure. So my name is D. Ray Freeman. D is for Donald but I just go by my middle name by Ray Freeman. I’m originally from Texas but I’ve been here in Las Vegas for about five years and I’m a co-owner of RTS Premier Solutions. We do all kind of IT work and you know AI and cyber security around the public sector. I’m also co-owner of a company out of Atlanta Georgia called Win-Win Operations. My partner Shayna Benjamin is there in Atlanta and together. We have about 30 OEM partners that we we work with and about 15 teaming partnerships with other small and medium-sized businesses and we just bring together some of the best technology to the public sector. We serve federal government and state and local and education as well Manuel Martinez: Awesome. I’m excited as part of the conversation to learn a little bit more of kind of what brought you to want to serve the public sector, right? Ray Freeman: Yes, you know when when I first met my my business partner she actually reached out to me on LinkedIn. I was serving as a career advisor and business advisor and she found me on LinkedIn and was like hey I’ve won these government contracts and I’m not sure I know exactly what to do but I’ve won them and I’m starting to service them and I’m like well I’ve started this company and I have a 20-year background in technology and I’m actually going to some of these networking and meetups and I’m not sure exactly what I’m gonna do but I’m making a lot of connections in the public sector and we’re like well why don’t we try to work together? So we decided to partner up and become partners in each other’s business and figure out you how can we work together to serve not only the market that she had already but then the network that I was starting to build here in in Las Vegas and so we ended up closing more contracts and building more together and it’s just been a great partnership and you know so she really got me into a public sector environment that was already established. I just helped to grow it. Manuel Martinez: Got it, okay. So now, as we kind of lead to what you’re doing now, tell me a little bit about where you grew up and then eventually kind of what got your career started because I know that you didn’t necessarily, I mean there’s some technology in there but you know we talked about kind of that fork in the road where you kind of had a couple decisions so you know just tell us a little bit about that. Ray Freeman: Sure, sure so I grew up in Fort Worth Texas you know just outside of Dallas there and you know as a little kid I used to always say I’m gonna go to night school and I’m gonna learn technology and I’m gonna do some kind of job working during the day. I was probably six years old and I was saying that but you know as I grew up of course I got into music more and started playing piano and trumpet but eventually I started making just music just beats for people you know R&B hip-hop music that was just going out and people were getting my songs and starting to use them in their own productions and so I was like forget about this tech stuff I’m gonna be a music producer man that’s where I’m going and I thought that’s where I was gonna be and actually when I was in college I was on a music scholarship in Weatherford College in West Texas I was playing trumpet and a really good jazz band there and some guys I had made a track for, they got signed to a record label in Houston their manager came and he gave me a wad of cash and said “Hey, we want to buy this song from you,” and I was like, “Where’s the pen?” – No lawyer no nothing I signed over and you know gave him that and I immediately thought I’m rich you know I’ve got some money I dropped all my classes left school went and got an apartment in Arlington and blew through that cash in about a month really smart for a 19 year old but I started working during the day I was working on the back of a you know one of those recycling trucks where you buy aluminum cans and stuff like old stinky trucks buying basically garbage from other people I was doing that and I had a little bit of little bit of cash left and I enrolled in a computer class at night so it’s kind of like what my six-year-old self said I would be doing but it was just like a plus stuff just weren’t learning to work on hardware things like that but from from there I just kind of had a knack for computers and technology and I couldn’t really afford to just buy a computer I could buy a motherboard and a case and a power supply and I got some books and just figured out how to build my own computer to put something together installing an OS on it I didn’t think that could be something that I would ever really want to do but I don’t know I got kind of good at it I guess and you know one day I was helping my girlfriend who’s my wife now, we’ve actually been together since back then I was hoping to buy a car, her first car – I’m at the dealership and they couldn’t complete the sale because they were having some issues with Windows 95 and I knew how to work Windows 95 because I had been messing around with it on my own stuff at home so I fixed it and got into the registry and whatever I got it working so the guy’s like, “Give me your ‘beeper’ number”, is how old this is, like – “Give me your beeper number I’m gonna I’ll reach out to you if we have any challenges or tech stuff.” This is before any Geek Squad or any of that kind of stuff existed. So gave him my number, right away I went home and I made some handwritten flyers and start handing them out at car dealerships and like, “I fix computers: 20 bucks.” Put my number on there and he called me a few times he actually owned a couple of car dealerships around Arlington, Texas and I got a few more calls and when it’s time to go back to to college I’d be back there but then I come home and I had clients I was out “fixing” computers during the day so that was kind of the first work that I had was just independent work but eventually I was hired by Page Mart this pager company this of course out of business years and years ago they hired me as a helpdesk guy just doing analyst work going and fixing stuff in the office that was my first real tech job in a real office and I was like, “You know, this seems interesting I might could make a make a go of this, I guess.” That’s how I kind of got started into even thinking that technology may be an option for me. Manuel Martinez: So a couple questions there with regards to kind of thinking that you’re going to be the music producer and- What were some of the skills that kind of looking back now, you probably didn’t realize it at the time, but you know – having to sell your music, were you marketing this to other artists? Did they just kind of, as you’re building this through school, like- I’m just curious how people came to know that D. Ray was the person that produced music. Ray Freeman: Well, I figured out pretty early on that… know if I found it if I found something in a book I could retain whatever I read and I learned about copyright so I learned how to copyright the songs that I was creating and I learned how to reach out to record companies to say you know, “Hey if you have an artist signed-” I’d send them a letter, “If you have an artist signed, then send them to me and I’ll help to make some music for ’em and send them back then y’all can produce it.” So I was sending out letters everywhere I’m sending out demo tapes with my music and other artists on it I was you know going to little battles and little concerts and stuff and I’d hand out tapes no discs or digital back then I’d hand out tapes of my music to people you know eventually I got heard by someone who was a pre-established artist and he brought me in to be a co-producer and a keyboard player with his his group and so that was pretty pretty cool so I was like I’m “signed” kind of you know I’m working with an established artist. Manuel Martinez: In that process, were you always comfortable talking to people and putting yourself out there? Because that’s… I’ve talked about it a couple of times, like transferable skills. Like at the time, you don’t realize, again, going out and… Like if we think about it now, it’s like personal branding, letting people know what it is that you do. Back in the day, the only way to do that was, again, you had to kind of put boots on the ground and hand out tapes and be able to go through and send letters. So is that something that just kind of… you had a natural… I don’t want to say natural, but maybe you kind of developed the skill of being able to talk to people and not being afraid of rejection. Because it’s no different than like applying for a job. Because you’re… basically, it’s the same thing. It’s like, “Hey, I’m applying. I’m applying.” Now, you’re going to get a lot of no’s. Most people might say, “This isn’t for me.” But you stuck with it. So I’m curious what led to you continuing to go on. Ray Freeman: That’s a great question and actually I was terrible at it in the beginning absolutely terrible and when I think back on some of the situations that I was in – of course as everybody says Monday morning quarterback I wish I knew then what I know today because I didn’t know how to brand myself I didn’t know how to market myself I’d be in the room with major artists from major labels and I was just one of the guys hanging out in the studio doing what people do in the studio which is not always the greatest thing so I really didn’t know what to do or how to make myself stand out back then so I’ve missed a lot of opportunities that I really probably could have made that career take off better but no I wasn’t great at it I was just I would do my little part I’d make my music and I kind of just kept my head down and stayed down worse advice I could give somebody is just keep your head down and stay quiet stay in the background, worst thing you can do. Manuel Martinez: So then, obviously, at that point in time, you’re not as vocal or as memorable. So the reason I ask is I have a guest that I interviewed just before you. She talked about like she was a drummer, Rebecca. And that skill of having to go through and market yourself, right? It’s different. It’s not like, hey, I can post stuff on social media. But it is, it’s going out and developing the skill of how do you talk to people and not being afraid of speaking up. Because I don’t… We’re similar in age where like my dad, that was what was instilled in me is keep your head down and just do the work. That might be good advice in certain industries. Like so he was in construction. So, OK, well, maybe that makes sense, right? Like you’re not going to be like, hey, I’m the best bricklayer in the city of Las Vegas. So it makes sense. But in most other industries, you do have to learn to, again, not boast and talk about how I’m the greatest, but make people aware of what you do. So how did… How did you learn from that experience moving forward? Was it not till later on when you were in tech? Is it just those first couple interactions with labels, you know, with these record labels and then you start to develop it? Like did it take you six months, six years? I’m just curious on the time frame. Ray Freeman: It really took years before I developed the the confidence, and actually, you know I really wasn’t great in school when I was in you know in high school or in college – I wasn’t great in classes at all. You know later on I decided I needed a few credentials so I started taking these MCSE classes Microsoft Certified Systems Engineer classes and I said, “Okay I’ll – this seems like something I could do, and I couldn’t afford to take the whole course there was like a full course to take all of – I could only afford to take up the first few classes to get the Microsoft certified professional and then they used to have this bookstore – 50 off bookstore, half- off bookstore, and they had all these books you could go and buy about you know, learn how to take the exams and how to learn about networking and all these things. So, I just bought a bunch of books really cheap and read them. So I went in and I took my first certification class. I got one cert and I said, “Okay, this is good.” And so I was like, “Well let me just see if I can study on my own and take the next-” I think it was a series of five or seven classes you had – or tests you had to pass . So I went and took the next test and I passed it. Back then they used to show you the score and it was up to like a thousand, and I made a thousand on it – still got the document, like I scored perfect on it, and there were guys there who were, you know, 40 years old, 50 years old and I’m, you know, in my 20s at the time and someone would tell me, “This is my third time taking it I still didn’t pass.” Ray Freeman: And I’m like, “Really? That’s weird, it was kind of easy for me.” So I went and I studied for the next one, it’s like, “Server in the enterprise for NT server” or whatever it was back then. Went in, took the test, got another thousand. Like, “This is crazy.” So there’s the next test and it was another Windows NT test I’m like, “I wonder if I could just pay for the test and go in and take the next one like right here, today.” So I did Manuel Martinez: Without studying? Ray Freeman: So I did. Without even studying and I went in and took the test and passed it. I was like, “Holy crap, I’m smart.” I didn’t have the confidence or even think that I- I mean my mom used to say, “Oh, you’re smart, you’re mr. know-it-all,” but I’m like, “I’m not smart, I do terrible in school.” But this is the first time that I was actually excelling in something and it just – that gave me a lot of confidence to feel like, “I really know this stuff.” Manuel Martinez: And do you think you did so well… And again, I believe that you’re smart and everybody’s smart. I think a lot of times, and just people I’ve talked to, do you think school just wasn’t interesting to you? Whereas this technology, that’s something that you have an interest in. So again, you’re going to put more attention to it. So if I think of my son, he doesn’t care much for… like… math. Now, he’s good at math. He just doesn’t put in the effort because it doesn’t interest him. Now, when it comes to history, I mean, he can rattle off facts, tell me about… ancient times and people. And I’m like… Sometimes I think to myself, “I’m going to fact check him.” And I’ll pull something up. I’m like, “Oh my God.” This is right. But again, it’s of interest to him. So again, it’s not that he’s not smart. It’s just he doesn’t have an interest in math. He has an interest in history and English and reading. So do you think that that had something to do with it? Ray Freeman: A hundred percent, and you know in the 80s, 90s, back when I was little and going through school, education was a lot different then, you know. You were taught to not work in groups, not work together. You sit down and you fill out the bubbles on the Scantron or whatever and you do it on your own, and I was more social. I was at my mom’s house a few months back, she still lives in Texas, and she has some of my old report cards and my teachers used to always say, you know, “Donald is a social butterfly, he’s always talking, he won’t stay in his seat,” and I’m looking at this going like, “Mom, did you see this? Did you do anything about this?” But yeah I was always wanting to be social and out and doing something different, and not necessarily just sitting there by myself studying. So you know, this gave me the interest in something that was challenging in a different way, and I didn’t really know how – like I knew how to read I wasn’t saying I didn’t know how to read, but someone taught me that, you know, reading is different for most people. Some people start from the beginning of a book and they read it to the end of the book, you know. Others, they may start in the middle and maybe some in the back, some in the beginning and just kind of flip through and retain it. So I had to learn – how do I learn how do I read and and retain information. And I’m more of a flipper; I flip through and I go through. I may start at chapter seven and go back to chapter two and then go back to the beginning and the end, and… but for some reason I could retain that information and understand it and that had never happened to me before in the past or nobody ever taught me that it’s okay to do it your way and not the way that they say you’re supposed to do it. Manuel Martinez: That’s interesting because I would say I’m the opposite. I’m one of those people that I have to go cover to cover. Like I have to read it from start to end. And then once I almost read things twice because I’ll go through it and just almost skim it. Like I’m reading it fast just because I need to know all the context. Then I will start to flip back and forth. Like, okay, I remember this part. Let me go dig into it. Like chapter three, oh, chapter nine, chapter four, chapter 10, like, and then bounce around. So that’s interesting. I didn’t realize that there’s people like you that will start doing the flipping from the get-go. Ray Freeman: Yeah, if I start in the middle then I’ll be like, “I wonder how we got to this,” and that’ll intrigue me to go backwards a few chapters. Like, “Oh I wonder how this got started.” So I’ll intrigue me to go – you know it just – it’s something about flipping around that just makes me more interested of, “How did we get here?” How did this book- How did the author get to this point?” And that’s that’s where it came from. Manuel Martinez: Interesting. So then now as you’re picking up some of these certs, you’re doing a lot of this learning on your own. You’re realizing that you’re able to retain this information and excel, right? Especially being able to take an exam and just – that same day and just pass it. Because again, it’s not like you went something completely different. You’re not doing Microsoft and like, well, let me go take a Cisco cert. Might’ve been a little bit different, but after you get a couple of these certs, I’m assuming you started to build some confidence that like, “I can succeed.” Not that you weren’t already kind of building that, but now you’ve got some credentials. So what do you decide to do moving forward? Because at this point, are you still at that help desk job? Or had you kind of moved forward a little bit? Ray Freeman: They got rid of me a long time ago, but I started applying for other jobs. Back then when you wanted a job you had to get the newspaper and get the classified ads and in the classifieds – first I wanted to be a music teacher that was really what I was going to school for and when I would look in the classifieds there would be nothing about music or teaching. But it would be page after page of tech jobs just multiple pages and I can almost have my pick because a lot of the people who were around my age and just you know – computers and the Internet was all kind of new then, everybody didn’t have a computer at home and surely didn’t have the Internet at home. So, I did, I had a computer and I had an AOL account so I could get online and I had hands on experience of actually working on stuff and I had some people who were references for me, they could say, “Yes, he did this he fixed this he did a great job for us. So I found that I could get a job pretty easy and so I would apply and I’d get a job and then recruiters would be calling me and sometimes the recruiters would be kind of unscrupulous like they would be whispering “Hey, can you talk?” You know, “Are you at work right now because I want to talk to you about coming to work for us.” So I’m like, “Oh, OK,” you know, so I jumped jobs a lot during that time frame because I was just being poached by so many different companies and you know so having the confidence to excel and try things in technology to get those certifications – and I started getting more certifications I went into to Novell the CNE, CNA certifications. And just from learning more of that getting these jobs, working, getting on the job training – that just gave me more and more confidence that I can really do this. But there was a wrinkle at the same time – the music part was taking off pretty decent at the time. So the guy I was signed to his name – His name was Erotic, nothing weird like that but he had a production studio and I used to work during the day and I’d go to the studio every single night and there would be big artists coming through – Snoop Dogg, OutKast, they would be coming through and they were there to work with him as their producer but I was co-producer, keyboard player. So I had a chance to be featured on a lot of songs that are popular and that went you know – pretty big. You know so I was torn between, “Do I go this tech route or do I keep working on this music thing and see if it if it takes off??” Eventually I got a probably one of the better jobs I had at the time, it was for Citibank. They hired me to come in and work on a CRM system and it was paying pretty good money, it was more than most of the people in my family had ever made and it’s like, “I’m kind of balling right now, this is good.” You know so I had a great job, I’m doing this tech stuff, I was not in school for technology or music anymore, I had work, and I had this music thing going. So that that was the route and it was just a crossroads of “Which one is going to take off?” Manuel Martinez: I have a question there regarding kind of some of the decision-making. So you mentioned earlier on, like where you had kind of gotten that big check as a young producer and kind of blew through it fast and at this point, again, I’m not that familiar with the music industry, but in tech, working for Citibank, like I said, you’re making good money but it’s a regular paycheck. On the music side, I’m sure that it’s not as steady, right? So if you get featured on a song and you co-produce and it does well, financially you do well but when it doesn’t, it’s not steady. It probably ebbs and flows a lot more, right? There’s probably really good months and then not so good months. Did that factor in a little bit into kind of the decision of where I wanna go or did you also think, like, “Man, I’m hanging around artists, I have the ability to maybe continue here and be a Timbaland, be a somebody that can go through and produce for these big artists? Ray Freeman: You know I didn’t have the business savvy then so as I mentioned I wasn’t really speaking up for myself and making sure that I’m mentioned in the credits and that I had the publishing deals. I was just glad to be in the environment and just glad to be there and so I didn’t really you know I made some money I got a chance to travel and go to some different places and meet some different people but it wasn’t paying off the way I want it to. The music thing thing was fun, I was having a great time but the tech was actually paying it was paying the bills and I was was doing pretty good on the tech side. And you know from from the technology side I was actually – since I had these certifications and I was able to pass these tests pretty – relatively easily I started a tech school, South Fort Worth, a friend of mine, we rented this fellowship hall on the side of this old church on the south side of Fort Worth, Texas, and I opened a computer school, called it “Dominion Training” since it was a church. And I had people that would come in and they would take certification classes from me to learn how to go and pass the Microsoft tests. So I was getting a lot of people who were coming to my classes getting certified and I was helping them get jobs and you know how to get into the industry. And this was an inner city area. And it’s kind of a rough area in Fort Worth so some of the people that were coming to this school they definitely would have never been able to afford going to some major either university or even one of the expensive tech schools. So it was a great service to be able to offer. We ended up getting into a voucher program where the city was paying people where they’ll give them a voucher if they’re on unemployment or something where they could bring the voucher as payment to us for them to come and take the class. And the tech side was really starting to just grow and the more that grew the less time I spent in the studio. It just kind of started to fade out and eventually I was making enough money to where I was doing the kind of stuff I wanted to do. I was buying fancy cars. I had a couple of BMWs and I was doing okay at the time. And so the music thing it wasn’t paying as well as I want it to and it just kind of started to fizzle out. Manuel Martinez: That feeling that you mentioned at the very beginning where – like when you’re in the music industry, you were just kind of happy to be there and in that environment. And on the tech side, you’re doing a lot more. You’re getting poached. Like the contrast that I see here is where in the music, you enjoyed it. Not that you were speaking up a lot on the tech side, but it seemed like there’s a difference. Like, oh, I’m good at this. I can help. I can do a lot more. Whereas over here, you’re like, I’m just happy to be here. And I know that a lot of times in really any career, there’s a lot of times where people will get to a role and it is that feeling of, well, I’m just happy to be here. And kind of, I don’t want to say it’s imposter syndrome for some people it might be, but it’s just that feeling of like, I’m just lucky to be here and this is good enough. But on the tech side, it sounds like you didn’t feel that same way. It was almost like, not that you were like, hey, I’m lucky to be here. It’s like, “I worked to get here. I deserve to be here and I’m going to continue to grow and build my skillset.” What made you kind of – like, what made that difference in the tech space versus like in the music industry? Ray Freeman: Great, great question. You know on the music side I was a side guy. I was under someone else who was the premier producer. So he had the spotlight. He had the fancy cars and everything was around him and I was just kind of working under him. And I just stayed down there in my little space. On the tech side I was the man. It’s like you know I had my own building. We had desks and computers. I had this great job. I had an office at my job with a door and stuff. You know so I guess I was in a more respected position on the tech side and I was looked to as an expert. When people came to the class I was teaching the classes. So they saw me as the guru, the tech guru who was able to disseminate this information. I could simplify it to where just regular average people could understand it. I’ve never had just this huge tech vocabulary that I was just so high up but I could just take what is really complex and make it simple for everyday people to understand. And people like that. They would come to me for advice and I was giving career advice and I was seeing people excel from what they were learning from me. And that felt good. On the music side, I was contributing but then my name wouldn’t be on the marquee or my name wouldn’t be on the front of the album. It would be somebody else’s name and somebody else’s production and somewhere in the credits it may say “keys by Ray Freeman.” But it would be in a small print way at the bottom of the CD or you know CDs by then. Manuel Martinez: Where somebody has to search for it as opposed to just front and center. Ray Freeman: Oh yeah, you’d need a magnifying glass to see my name in the credits but it’s in there. But on the tech side it was me and I had partners that I worked with but I’ve just always been a serial entrepreneur of starting little businesses and entities and this one was really taking off. Manuel Martinez: And we kind of touched on it a little bit at the beginning, but you seem to be okay with kind of the rejection and having that entrepreneurial mindset. What is it that kind of kept you pushing forward? Did you experience a little bit of success at the beginning and just enough? And again, it doesn’t have to be, “oh, I’m getting nine out of 10.” Sometimes just one out of 10 or one out of 50 might be enough to say, “Okay, I can keep doing this.” So what is it in you that kind of started that? And then now at this point, like you said, hey, I have a building, there’s also a little bit of creativeness and I’m guessing that that comes from the music, like the art side of it is, okay, hey, I can build a computer business. I can start teaching other people, like most people that go in to kind of tech, they pick a role, they continue on and they progress. You did that, but at the same time, you’re also doing, you know, working for Citibank, but you’re also, hey, I’m teaching people, like you have this creativeness or seeing things a little bit different, like, “I’m really good at taking exams and studying,” and you didn’t just say, “Well, I’m gonna keep going and just gobble up every certification. You’re like, “Hey, there’s something here. Maybe I can teach other people.” Like how did that kind of all come together? Ray Freeman: You know, I think it was the successes that kind of drove it. I’ve always been an ambitious person. I wanted to have things that were better. I wanted to travel different places and see different things. My mom used to take me on trips. Matter of fact, when I was like 14 years old she brought me to Vegas. We lived in Texas, she brought me to Vegas and we stayed at like the Circus Circus or something way back then. And just seeing the city and seeing the lights, I was like, “Man, when I get older I’m coming to that city. I’m going to be there.” So just the things that she exposed me to, she took me to Canada. I went to Toronto. I’ve always wanted to have better things, to be able to do better things and to be an inspiration to other people. And that kind of drove me to not just want to exist, not just get a job and stay stagnant in one area. But how can I keep moving up? How can I move to the next level? And what’s the next thing and the next thing? And I guess I would just get bored easily doing the same thing over and over. And I wanted a challenge. I wanted something new. So I’d always take on a new challenge. So another big stepping stone for me from the Citibank City Group job was I was recruited to come to Houston and work for a deregulated energy company. And I was like, “Wow, this is my first time being relocated. This company is actually going to pay to move me to another city and help me to get established.” I was honored to even be in that kind of position as a young guy. So we packed up and moved to Houston and I started working in that industry. And things were climbing up and that’s when there was a downturn in the industry and things started to change quite a bit. Manuel Martinez: Yep, and it’s perfect, cause that was around, I thought this was around the timeframe. And you mentioned wanting to kind of do more and being comfortable with, “Okay, I’ve achieved more, I’m gonna go through and kind of enjoy a little bit of the fruits of my labor, right?” Like I worked, you worked hard, you got here, you said a couple of cars, you got a nice house, you’re being relocated, you’re being poached. And a lot of times people only see the end result, right? So at some point, you’re climbing, you’re climbing, you’re climbing, and it sounds like around this time is where some of the challenges come in. And you’ve mentioned like it’s a downturn. So this is around the 2008, 2009 timeframe where it wasn’t just a downturn in the tech industry, but I mean, in most industries just across the board. Ray Freeman: Oh yeah. Back then I didn’t really know much about saving or investing, spending wisely. I mean, I may have been making a hundred thousand a year, but I was spending 150 every year. And that just puts you deeper and deeper in the hole. I think I was trying to live a music producer’s life on a tech salary because we were coming to Vegas a lot then. And I could buy a trip for a couple hundred bucks and we’d fly here 10, 12 times. We were coming to Vegas. And I was like, “Man, I’m going to live there one day. It’s just an awesome city.” But I was going on cruises and just doing the craziest stuff, spending so much money. And when that downturn happened, my wife was laid off like to say December 8th. And I was laid off like December 13th, like in the same time. And we hardly had anything saved up. We didn’t have any emergency fund. We had no investments. We had a six bedroom house that we had built in Houston, huge two story building. And when we lost our jobs, I had to start selling stuff out of the house. So eventually we sold most of the furniture, sold most of the TVs and clothes. We just had just us in this big house. I remember the echo in this place. I was so proud to have the house when I first got it, but it just became this albatross. I can’t believe now I’m strapped with this huge mortgage. And I don’t have a job and there’s nobody hiring. And we’re both just sitting here. We’ve sold most of our stuff. We don’t even have a couch to sit on. We’re sitting on the floor. It’s like, “What do we do?” Manuel Martinez: And you make a good point there is a lot of times something that’s not talked about much, right? Is not having, you know, it’s one thing you get a job, you start making more money. And usually the more common thing is you make more, you spend more like, oh, I can, you know, I got a $20,000 raise. That means I can spend an extra $20,000 or I made, you know, another $40,000. You know, you kind of continue to go up and up and not having like that financial education or the literacy and understanding, or even just a mentor, just somebody, because it sounds like the good and the bad is, you know, you’re entrepreneurial, you’re figuring this out on your own, which sounds like you didn’t at the same time have mentors or people that kind of go through and explain to you and say, hey, are you maxing out your 401k? Are you putting away a little bit of savings? Like not having that, I mean, that was, you know, like you said, looking back now, like, wow, like what a huge learning curve that early on. Ray Freeman: Oh yeah. Oh yeah. Oh yeah. I blew so much money during that time. And I mean, I don’t regret it because I had so many awesome experiences and I’ve got the craziest stories on places I’ve been and things I’ve done. So I have no regrets on that end, but the older wiser me says, “Wow, you should have done these things differently because we would be in such a better position today if I had done things differently.” So, you know, it happened. Manuel Martinez: So then now you get laid off, you have this downturn, you’re selling off what you can to kind of continue to live and make ends meet. So like what transpires? Like, well, you know, was this going on for a couple weeks and then like, okay, I’m good to go. Somebody hired me. Like what happens and you know, kind of what’s the next step for you to go through and say, hey, you know, I went from having everything to now almost nothing and how long did that last? Ray Freeman: Oh man, that went on for months, almost a year. I can remember calling BMW and because they were looking for my car to repossess my cars. And I remember just finally just giving up one day, call BMW and say, “Look, just come get both of them. I’m just going to park them outside. I’ll leave the keys in them. Just come get them. I’m tired of running and hiding from you. I don’t have any money to pay you. You can have them.” We’re close to foreclosure. We’re just about to lose the house. And so they came and got the cars and I took about, I had about $700 I got from selling some stuff in the house and I went and bought a 1982 Saab. And that was a beater, man. It was a beater. And I remember being okay with it because my first thought was how embarrassing that I had a huge seven series BMW and a convertible BMW and we’re just ballin’. And all of a sudden I’m driving this old clunker beater at the door doesn’t even say closed and I’ve got tape to hold the door closed. And I was just taking random jobs. I was a DJ for a while. I was DJing weddings, bar mitzvahs and birthday parties and stuff. So just whatever I could do. I was working at Best Buy, putting DVDs on the shelf. Just anything I could do to keep, just to keep the lights on and to keep some food going for my wife and I. But the first break I got for another tech job, it wasn’t even in Houston or Texas at all. It was in Pittsburgh, Pennsylvania. And so I’m like, “How am I going to get to Pennsylvania to get to work?” That was the first job that hired me and it had been almost a year without anything, without any savings and just scrapping by trying to make ends meet. Manuel Martinez: And you mentioned that not feeling embarrassed, right? Cause a lot of times, it’s happened to all of us. It’s happened to me where at one point I’ve had to take those step back, take a job that didn’t pay as much just to kind of either, sometimes you’re just to get the experience, sometimes it’s just to keep income coming, right? To stay employed. And I think I would have had that similar mindset as you as- I don’t feel the embarrassment. Like I’ll tell you right now, I think I’ve have much more pride and I don’t know if maybe it’s your worth ethic or maybe it’s just knowing that you’ve done it before and you can do it again is, heaven forbid, like I don’t wanna lose my job, but if it did, I think I would do similar to you. Like I would go and anything I can do, I have to continue to bring in some sort of income. So was that kind of the mindset is like, okay, I did it once, I can do it again. Ray Freeman: Oh, for sure. My mom, she worked on the same job for 25 years. She worked for a Miller Brewing Company, the Canning Division. And so I watched her work hard, take care of my brother and sister and myself and do things for our family. And just for her to get that job, she did something similar that I did. She went and got some certifications and she landed a job and she took care of her family. I used to watch her work 12 hour days, sometimes 10, 15 days in a row, no days off. And it was nothing for her to work overtime, do whatever it took to keep us going. So we’d never have to do without anything. But she busted her tail to make that happen. So that work ethic was always in me that if somebody’s hiring, I’ll go work for them. I don’t care what it is. If I’m building a fence or cutting yards, whatever I need to do, I’m going to make ends meet. So that’s what just instilled in me from growing up. Manuel Martinez: And it sounds like, and for anybody that is kind of looking like – I wanna get to a certain place or I wanna be around people, I think one of the big things that I’ve taken from what you’ve mentioned is exposure. Your mom exposed you to her work ethic. Your mom exposed you to traveling and seeing other things. So you’re like, oh, there’s more than just kind of where I’m from. I guess the kind of takeaway that I get from there is for other people as well is, if you want to get into a specific area or if you want to be this person surrounding yourself with those people, and I think now there’s no shortage of it. You can go and there’s networking events, but there’s even user groups and all kinds of like-minded people, and if you start to get exposure to that, I think it really helps change or set your mindset similar to you. Where did it come from for you? It wasn’t from people in their neighborhood because you didn’t know other people that were in the tech industry. But there are certain traits, like the work ethic, the being exposed to, hey, I can do other stuff. So it sounds like at this point, you got this job in Pittsburgh, and you weren’t scared about saying, I’ve got to go somewhere else, right? Because you’re like, I’ve traveled before, it’s not a big deal. But from our conversation before, it wasn’t as easy as like, well, I’m just gonna go to Pittsburgh and I’ve got this job, and we’re back in business, right? We’re back to where we were. Ray Freeman: No, man. It wasn’t that easy. We were behind on everything and using credit cards and maxing them out, of course. So I had a card. I charged a one-way trip to Pittsburgh and didn’t know much about how to do the rental car and stuff. So I used the same card, got a rental car, and I get to this hotel I was going to stay at. The car doesn’t work anymore. So I’m like, “Uh-oh.” I had probably 40 bucks or something in my pocket, but this card doesn’t work, that card doesn’t work. I’m tapped out. It’s in the middle of a snowstorm. It is just ice cold where I’m at. It’s late at night, so I’m thinking, “Okay.” When I start this job on Monday, I think I got there on a Saturday night or late Saturday night or something. I start this job on Monday, I’m calculating, thinking, “Okay, I’ll get my first check by Friday, and if I could just survive until Friday, I’ll be good.” My wife’s back home at the huge, almost empty house in Houston, and she’s got what she needs there. So I’m figuring, “I’ll find somewhere to park, and I’ll sleep in the car.” I remember that first night, I went to a Jack in the Box or something and had some food and got a drink. It had ice in it, and I put it in a cup holder, and I just bundled up, and I parked somewhere, and I’m sleeping in the car. Next morning, the drink was just solid ice, and that was like a low point for me I’m like, “I can’t believe I’m sitting here sleeping in this car, and it’s so cold that my drink has turned into a solid block of ice.” So I was like, “Well, I made it through that night, so let me get up and figure out how to get somewhere and get cleaned up. If I can make it and just get to work Monday, I know I’ll be somewhere warm, and I can be at the office all day, and I can just figure out how to bed down at night in this car. If I make it to Friday, I’ll get a decent check. It was an okay job, and I’ll get somewhere to stay.” That’s what I did. I’ll stay in the car for a week. It did warm up, at least to be above freezing, and it was okay. That gave me…it’s a learning experience, but it didn’t take me out. I’m like, “I did not die from this.” I didn’t have to call anybody and say, “I’m down on my luck. Can you send me? I’ll deal with it.” I just figured it out. I started figuring out how to survive when you don’t have a place to really live. I got a styrofoam cooler, and I would get some cheap groceries and stuff. There’s a Dollar General that I could buy groceries from and just keep in this cooler. I go to the Goodwill store, and I found a little George Foreman grill and a rice cooker for a couple of bucks each. I found somewhere to plug up, and I cooked some food. I just learned how to make it and to be okay with it. It wasn’t a super long time, so no disrespect to people who have had to do that for months or years. It was only for a week. I survived it. I got through it, and it built a sense of character and appreciation in me for everything that I have. Manuel Martinez: Right, and it’s funny that you mentioned, after that one, “I survived,” right? “I can do this,” as opposed to, and again, there’s nothing wrong with asking for help either, but there was something in you that says, “I can do this. I don’t need to depend on somebody else.” Now, again, people will say, well, you could have, you should have, again, everybody’s situation’s different, there’s nobody that’s gonna tell you what’s right for you, but I like the fact that you were like, “Nope, I did it once, one night, I could continue.” And you just – it seems like at that point you’re taking it day by day. You weren’t like, okay, I’ve got this job, and you were thinking, from here to Friday, you weren’t like, oh, from here to next month, that’s it, like my problems are solved. You broke it down into manageable steps, right? It’s almost like goal setting, right? Is it a glamorous goal? No, but it’s a goal, and you said, by Friday, okay, I survived one night, okay, one, now I’ve only got six more or five more to go. So is it – is that something that you continue to do forward, is just setting those goals and saying, okay, I did it, I’ve just gotta do this one thing or these two things, and I can continue to grow. Ray Freeman: Oh man, 100%. Breaking big goals down into small chunks. That ended up being something that took my career a long way, but it’s something I grasped early on. That really was my mindset. I can just make it to this week, and I have a plan. I have a plan, but once I do get this first check, what’s going to be my plan? I learned early on, break big goals down into small tasks, have a plan of what you’re going to do, and be able to execute that plan. I knew, “Okay, if I get this check, there’s an apartment complex, and it’s like first month’s free.” You had to show where you had proof of income. I had proof of income. I got the first month’s free. Same thing at a Rent- A-Center or a rent-to-own place. I’m like, “I need a mattress, and I need a microwave.” It was like, “Okay, you get the first two weeks free. Great.” I just started to build up a little piece at a time. Eventually, I had a furnished apartment. After a few months of being there, I’ve had enough to fly home back to Houston and see my wife, or I could bring her to Pittsburgh, and we could stay there for a while so we could get back together again. I was working enough to send money home, but still not really enough to cover paying for that house that we couldn’t afford in the first place, plus my living expenses here. We were still nearing foreclosure there and just barely skimming by. But at least we had food, we had clothes on our back, and we were both in a safe environment. Manuel Martinez: And I think that’s something that a lot of times is missed. We see the end goal, or it’s good to have that kind of that five year plan, but sometimes making sure that that’s not all we’re focused on, right? It just can’t always be the end goal. Sure, it’s good to have dreams and to have an idea of how you wanna move forward, where you wanna get to. But I’ve seen a lot of people that just go, and they’re like, well, that’s it. That’s all they think about, and your career’s a lot longer than, hey, within the next year, I’m gonna be a senior architect, or I’m gonna be a senior cybersecurity person. It doesn’t happen that quickly. And just knowing, okay, that’s something to aspire to. Could you do it in a year? Maybe, but what are the steps you’re gonna get there? Just thinking about it and saying, I wanna get there, I’m gonna get there. That’s not enough. Ray Freeman: Definitely. Manuel Martinez: So then, you get this job in Pittsburgh, you’re starting to kind of put things back together, and how long did that take to eventually, you can start to kind of reunite with your wife. And you’re in Pittsburgh now, right? So you’re going from Texas over to Pittsburgh. Did she eventually move with you? Did you guys move somewhere else together? So I’m just curious kind of what happens next. Ray Freeman: We lived back and forth in different hotels and extended stays. I would book a place that was anywhere from a week to a month at a time. So we never really had a consistent place that we just lived. That went on for almost a year that we were in Pittsburgh. But we made the best of it. When we were there together, we ended up going to Pirates Games and Three Rivers Stadium. Well, it used to be Three Rivers Stadium. Not a big Steelers fan but, was able to go to some Steelers games just to see the city and learn the people and everything. We just embedded in that city and that culture there for a while. Eventually, I wanted to get back to Texas. This was a contract job that I was on. It was coming up on the year when the contract is about to be over. It was an IT contract. I was doing some CRM database transfer, some weird thing I was working on. Eventually, we had brought one of our cars there. Drove from Texas to Pittsburgh. Barely made it, but we had a car there. Just before the contract ended, we took about a two and a half week road trip. We left Pittsburgh, went up to Canada, and just zigzagged across the US. We eventually got to Florida and came all the way back across to Houston. For about two weeks, we just drove around and saw the whole East Coast. Manuel Martinez: And as you’re kind of doing that and knowing that your contract’s ending, I’m assuming during that time period, you’re also kind of putting in applications and you’re like, “Hey, I know at some point I’m gonna go there, so let me kind of make the best of it.” And I do that pretty often, like when I’m going from one role to another, like I bake in a little bit of extra time and say, “Hey, I’m gonna take time and go do something for myself because I know that once I get into this next role, it’s full bore.” And that’s that whole drinking from the fire hose and everybody’s kind of all this information as you acclimate to this new job. Ray Freeman: After all of that was over, we finally got back to Houston. I found a realtor who was willing to help me get out of this house to get it sold. He was just such a really nice guy. He put in some of his own money to help me to get it sold. My wife, she’s in real estate. She was a realtor at the time, but we just needed somebody to help us get out from under this because we were so underwater. We finally got the house sold, but the next job that I got wasn’t in Houston. It was in Austin. We were like, “Okay, we’re moving to Austin.” We moved to Austin. We did something similar. We got a first month’s free apartment. We got some stuff that we moved into the place. That was another surreal moment, going from this huge house to this dinky apartment that wasn’t in a great location. There were some people fighting outside the day we moved in. It was like, “Oh my God, what have we done?” We moved in there. I started working with this company that was actually doing some public sector work. That was kind of cool. That was one of my first avenues into the public sector back then, working on a North Texas Tollway project. That was interesting. I learned how to build an office, physically build an office that was going to house all the public records and put in all the IT and telephony and the staff. I really learned a lot about just building a business and staffing a business and running a business. They taught me a lot there. That was a good time. We had a career restart. She got into relocation and doing more realtor work. We started moving back up again. We started buying nice cars and going on trips again. We went back up to the top. Manuel Martinez: And this time when you’re doing it though, did you learn from the last time and say, Ray Freeman: Of course not. Manuel Martinez: let me, no, no, we’re not gonna save a little bit? We’re gonna go right back. Ray Freeman: Of course not. It took me a while to really learn it. I was hard-headed. After being at the bottom for so long, I felt like I’m finally back, so- Manuel Martinez: You’re like, man, third time’s a charm, right? (laughing) Ray Freeman: Of course I didn’t learn it. It took me a few of those restarts to really get it. I was like, “Wait a minute. You need to do things totally different.” I didn’t get it right then. I made some of the same mistakes, but made some of the same mistakes again. At least this time, we were able to build a home and buy a home there in Austin. We just started living a nice life there. Eventually I was poached to another job that was back in Fort Worth, Texas. We got rid of that place, moved back to Fort Worth. Every time I’d get a better job, I’d move somewhere else and make more money. I could just keep spending because eventually I’ll find out a way to make more. It was working there for a while. Manuel Martinez: So as you’re going through it, so again, now you’re kind of back into that working for other people and doing that. But now at the beginning, you mentioned that you have a business here and then also one in Atlanta. Correct? So how did that come about? Which one came first? It sounds like you’re in the kind of Midwest, probably a little bit East Coast like with Pittsburgh, but so you’re in this area. Did Atlanta come first and then eventually Vegas knowing that, hey, I want to be here. So how did it go from you working for other people and kind of getting poached to saying, okay, I’m going to build a business now? Ray Freeman: You know… along this journey, I had some really good jobs before I even get into these businesses. I worked for American Airlines. I helped to build integration with US Airways. I went to work for Southwest Airlines. I was just good at bringing in methodologies from different companies and different teams who were merging together. I learned about agile methodology and became an agile coach and trainer. That led me to just so many other different positions. There was this whole thing where we moved to Jamaica for about six months, which is a whole other thing. I really wanted to work for myself. I wanted to have my own business, my own entity. I had a good friend of mine named Anthony. Anthony was my coach and also my business partner. We started this company called Agile Consultant Guide. We had landed a contract with AT&T. At the time, AT&T was like a Fortune 5 or Fortune 10 company, huge. We were working with this big entity. There were some things that they were doing that were going to fail. This is not going to work out right. He just gave me some encouragement of some things that I should go out and just say and do and be bold. I remember I had one of those elevator conversations with the CTO of AT&T. I told him, “You know what? Your whole agile release train that the team has put together, everybody’s going to be blocked. First sprint is going to be blocked. Promise you.” He was so pissed. He was shaking his fist and he was like, “What are you talking about? My teams are great…” The company I was contracting through, they got mad at me. They fired me. I went home. Two weeks later, he found me on LinkedIn and reached out to me and said, “Get in here. Everybody’s blocked. Show me what happened and why we’re blocked.” I went back in and we ended up getting that contract back and that was growing. They went to a freeze, moved to Jamaica. We had a contract with a bank on the island. We sold everything, moved to Jamaica. We did a bunch of transformation work there on the island. I moved to Beaverton, Oregon. I took a contract with Nike. I did an agile transformation with them for three months. Eventually, I got a management consulting position with a company called Adaptivate. That was back in Los Angeles. I moved to LA. We were in Marina del Rey, right on the water, right by the boats and everything. My living room window was facing the ocean. It’s a beautiful, beautiful place. This company, I was doing the management consulting work. I’m working for big oil and gas companies. I’m just traveling all over the place. They were starting a separate brand called Tribe. They wanted me to grow this business and just to build it and run the whole P&L. I did. It started growing. I hired staff and we had contractors working in different places. That taught me a different way of running a really sizable business. It wasn’t just me. I had people working in different countries that are reporting to me. This is amazing. I got people in Poland and people in Jamaica and people across the US. They’re all reporting to me. I run the P&L and I report to the CEO. It just gave me a different kind of confidence of not just running something that getting myself a job as an independent. Now, I’m starting to learn how do I get other people jobs? How do I help others to work? I can show value but bring in other people to actually deliver the value. That was another life-changing thing for me. I don’t have to do all the work. I don’t have to be the one who is always at the computer or at the whiteboard. I can bring in other people who are way smarter than me and scale this thing. I can do it globally. That gave me a whole different mindset, a whole different confidence in how to run a business. There was a lot in that thing there. Manuel Martinez: No, there’s a lot, but I think the area that I wanna hone in on is, your friend Anthony told you to kind of be bold, right? And you went to the CTO and you had that moment of like, hey, it wasn’t just be bold, but is it pattern recognition? Was it, did you, you mentioned like, hey, in a week your team is gonna be blocked. Was it through experience? Was it things that you were seeing that kind of – and I’ve talked about this before, a lot of times like we make mistakes, right? And you’ve made plenty of them, but at some point you also start to see through experience, I think a lot of times it’s pattern recognition is you saw something that says they’re gonna be blocked. And here’s why. And like, maybe you saw the blocker, because you’re sometimes it’s just a different perspective. Like they’re so entrenched and here’s what they see and this is what they know. Somebody from the outside sees something different, but then also now you are bold. Again, it’s a different industry than kind of back in the music where you’re just like, hey, I’m gonna sit back, but now you have this confidence, you have this
Building a Sales Career Through Authentic Relationships with Rebekah Panepinto | Ep055
Episode Information Show Notes What happens when a drummer who played for 10,000 people realizes the music business won’t pay the bills? Rebekah Panepinto shares her unconventional journey from Nashville musician to successful Account Executive, proving that your next career move might come from the least expected place. This conversation goes deep on how relationships trump resumes, why being visible matters more than being perfect, and how asking better questions opens doors you didn’t know existed. Guest BackgroundRebekah Panepinto is an Account Executive and podcast host who has built her sales career by prioritizing authentic relationships over transactions. After pursuing music as a drummer for Grammy-nominated artists, she pivoted to tech sales where she discovered her talent for building partnerships. Her journey from healthcare IT to global software consulting shows how following trusted relationships creates better outcomes than chasing job titles. Episode HighlightsThe Pivot MomentRebekah earned just $150 playing drums for 10,000 people while getting paid more per day as a nanny. That moment at 21 forced her to Google “best jobs in Nashville” and discover healthcare IT—launching an unexpected career path. Zero to Sales HeroWithout any sales experience, Rebekah got recruited by a bandmate who saw intangibles in her that she didn’t see herself. He taught her the fundamentals while she brought natural relationship-building skills that can’t be taught. Female Drummer AdvantageBeing a female drummer in a male-dominated music industry prepared Rebekah for tech sales in ways she never expected. It taught her to believe she could do anything and to never back down from male-dominated spaces. The Everyone’s-a-Prospect TrapEarly in her sales career, Rebekah believed everyone on every flight and elevator was a potential customer. Learning to properly qualify prospects saved companies from bleeding money on bad-fit customers. Podcasting Beats NetworkingTraditional networking events create forgettable exchanges. Podcasting builds authentic relationships where people share vulnerable moments and create lasting connections. Continuous Learning PhilosophyGrowing up homeschooled taught Rebekah how to love learning as a lifelong journey. Now she dedicates an hour every morning to podcasts and audiobooks, absorbing insights from business leaders while working out. Key Takeaways1. Follow relationships, not job descriptions. Every one of Rebekah’s career moves came through trusted connections2. Personal branding is non-negotiable. Being visible and consistent makes you memorable when opportunities arise3. Quality relationships beat transactional wins. Nobody should dread your outreach because you only call for the check4. Learn from everything. Even finance podcasts teach you about newsletter strategies and content creation5. Going all-in creates mastery. Whether it’s scuba diving or sales, full commitment accelerates learning Resources Mentioned– Tom Bilyeu’s Impact Theory Podcast– Ramit Sethi’s Money for Couples– Antifragile by Nassim Taleb Listen to the full episode to hear how Rebekah builds multi-channel touchpoints with prospects, why she’d choose relationship quality over quota-hitting, and what she learned from being capped at her first sales job. Released: January 13, 2026 Subscribe to Career Downloads for weekly conversations with tech professionals sharing their career journeys. TranscriptManuel Martinez: Welcome everyone, my name is Manuel Martinez, and this is another episode of Career Downloads, where each episode I basically hit the refresh button, bring on a different guest to learn more about their background and their experiences, to help you uncover any actionable advice that you can use as you’re managing your own career. So I’m excited for today’s episode. I have with me Rebecca Panepinto, and she is she’s an account executive, and she does a lot of, she also has her own podcast, she’s a drummer, so there’s a lot of information there that I think, it’s not just focused just on her career, but a lot of the skill sets that she has developed outside. Talked about it in a couple other episodes, some of those transferable skills. So I think this is gonna be a really good one to kind of, for those people who are like, well, I don’t wanna be just career oriented, I think she gives us a good mix of kind of both realms. So with that, I’ll go ahead and introduce Rebekah. Rebeka: Yes, thanks for having me. Manuel Martinez: I’m glad you were able to kind of make it, being from New York, right? Rebekah Panepinto: Yeah, it’s like, hey, I’m gonna be in Vegas, let’s do a show. Manuel Martinez: That’s awesome. Rebekah Panepinto: Excited, I’ll have you on the show here soon too, but it will be virtual, not in person, not as exciting. It’ll be fun. Yeah, we met through just LinkedIn. I saw what you were doing with your show, and I said, hey, I wanna know you, and understand how you’re doing this, the impact you’re making, and learn a little bit more. So here we are now. Manuel Martinez: Yeah, I like it. And I’m glad you did reach out, because again, I saw that you had a podcast, and kind of what you were doing, so it wasn’t so much career focused, but more around digital transformation, and the different people that you have on. So I have watched a couple of those episodes, and I got some good insights from just, I like hearing how different people think, and then also, I think you do a really good job of kind of asking those good questions, right? And then you got a lot more episodes than I do, but that’s a skill that is helpful not only here, but just in general, just being able to ask better questions, you get better answers. Rebekah Panepinto: Yeah, and just building relationships. There’s something about this that builds a relationship that’s truly authentic, and almost experiential, and like a moment that is shared together, versus just like bumping each other and networking event, you know? And like you quickly forget somebody’s name, or where they’re from. But the way you can build a relationship through podcasting is just a game changer, especially when you’re a salesperson. I’ve always tried to be a salesperson who is not seen as just somebody coming after the next sale, but instead more of a trusted advisor and somebody who wants to build relationships for the long haul, and have a repeat customer when the CIO goes to another company, et cetera. And so by having a conversation, even though typically mine are virtual, you’re able to open really cool doors and get people in a really good place where they feel comfortable to share their career, their advice, their principles, whatever it may be, to be able to be really vulnerable, so. Manuel Martinez: So can you tell me a little bit more about kind of where you grew up, and then eventually what got your career started? You know, what kind of go from there? Rebekah Panepinto: Oh, it’s been an adventure. So I was actually one of those weird homeschool kids, was born in Phoenix, and started college at 16. And so that had me finishing my undergrad at 19, which is a really weird stage in life to be basically like, what do you wanna do for the rest of your life? Because you don’t have a clue at 19. But that was the place I was in. I was like, well, I guess I’ll just get a business degree. And back in the back of my head, as you mentioned earlier, my drumming, is I wanted to be a big drum star. So Nashville was calling my name. So I took off halfway across the country, actually be a live in nanny to start. It got me to Nashville, and I was able to finish my undergrad online while working in the music business on the side, and actually providing for myself through being a nanny, because that’s a pretty good gig in the Nashville area, if you have the right family. And so big drum star was the dream at first. I spent two years, so age 19 to 21, going pretty hard after music. Until 21, I played a show for 10,000 people, and I got paid $150, and that was it. I was like, music business is not gonna happen for me. I love it, great opportunity. I remember I was signing autographs till 2 a.m. that night, just like this is it, and then had to go get in the car, drive through the night to wake up a nanny the next day to get paid more per day as a nanny than that gig even paid. And the craziest part, even that gig, the people I was playing with had paid for the spot, and it was just like, it was insane to see the reality of this is not gonna be financially feasible at all, especially as just the drummer. But hey, I got to feel like a rock star, I got to taste it, and it was fun. Artist I’d played for was Grammy nominated, and it opened some cool doors. It was really fun. I still have some YouTube videos out there somewhere. But I woke up that next day, here 21, just finished my undergrad. I was like, I gotta do something else. This is not it, and I’m not gonna be a nanny for the rest of my life. And so I kid you not, I Googled best jobs in Nashville, Tennessee, and it was healthcare IT. I was like, okay, I think that’s an answer. HCA, number one employer in Nashville, I was like, I guess I should go work for HCA, like the overconfident 21 year old I was. And I applied for a paid internship at HCA, and I got it, I was shocked. Well, here’s the funniest part of it all. The guy who hired me, his son was a drummer. He and his son had been doing drum covers in their little home studio they have similar to yours, and had offered through the interview process even, I wasn’t even hired yet, if I ever wanted to come record, like he had a studio, his son wasn’t really doing it much anymore, and he loved it, like helped me in that aspect. And I sat there laughing, because here I was choosing to go get a big girl job, and leave the music behind, because I need a career, I need to provide for myself. And my soon to be boss is like, come record drum covers at my place. And it all worked out, he was great. He got me my first job, I was a project manager for HCA, and then did my drum covers that actually did fairly well. I think I want a GoPro from one, and like they still live out there in the world that get me a gig from every time to time. But it was just super funny that here I’d been like, music business, not it, I’m gonna go get a real job, I’m gonna do healthcare IT, because it’s the right thing to do. And then in a really weird way, I was able to combine the two, and be able to still really be myself, while getting to work for this guy named Mike Adams. That’s pretty fun. Manuel Martinez: And you talked about it at the very beginning, where just having conversations, and having a lot of these different interests. So do you think that that kind of helped land the role? Granted, it is an internship, right? But having that commonality of just being able to have a conversation with somebody like, hey, I’m a drummer, that kind of leads to a conversation that has nothing to do about the role. Because I’ve been in some of those interviews where just something comes up, and it derails, I won’t say it derails, but it kind of takes it off topic, and it’s led to some pretty good outcomes. Rebekah Panepinto: Yeah, well, and if I would have just done my normal LinkedIn research of him, I never would have known his son was a drummer. Like I would never even known to kind of pull on that string, you know? But it’s who I am, it’s a big part of me. I’ve had this whole alter ego called Becca the Drummer. So naturally, I was gonna say, this is what I like to do on the weekends. And it made me memorable, probably even if he didn’t have a son that had a drummer. I just kind of hit the lottery with that one. But in a lot of cases, even in my sales approach, and getting no people, networking, et cetera, it makes me memorable. And so it doesn’t hurt to say, hey, yeah, I play drums, because how many female drummers do people meet, let alone one that can look up on YouTube, they’re like, oh, she actually can play drums. Or hey, I have a band on Spotify, like here you go, like I’m not just blowing smoke. I’ve been playing drums for 23 years, you know? So it’s a memorable way to impact people, probably the best way to put it. But then with him, what I realized, because I wanted that job, is I turned on the sales skills. And I learned the sales skills by selling myself as a drummer, because I had to go get those gigs. And I didn’t realize I was even selling until later, I was like, oh, that was 100% sales. I had to go find the opportunity, I had to go close the opportunity, then I had to deliver on the opportunity, which thankfully is something I don’t have to always do in my career now. And that was actually the scariest part is, well, now, crap, I gotta learn the music, I gotta actually nail it, the bands gotta like me, I’ve gotta stay on click, you know, all these other things. So I learned naturally just how to sell by selling myself into drum gigs. And then when I turned it on up, was like, I want this gig, I want this internship. I didn’t care, I was like, I wanna work for HCA, I want it on my resume. And so my follow-up was pretty intense. Manuel Martinez: Nice. Rebekah Panepinto: And it all worked out in the end, you know? Manuel Martinez: And you also said that you were homeschooled, and then you went and got your undergrad, and you know having done that a lot earlier than most people, sounds like you didn’t have that typical college experience or even high school. So I guess as part of the homeschooling, or is it because, again, I don’t know if part of the curriculum was to go out and talk to other people, but where did you kind of develop that ability to kind of sell yourself, right? Because again, it’s, you know, when you’re selling yourself to be a drummer, okay, you’re picking up that skill then, and I’m sure the very first one might have been awkward, might not have been, but I don’t know if you had other experiences prior to that. Rebekah Panepinto: Well, that’s something I did start to realize as I got older, obviously, you know, hindsight’s 20-20, and like eventually you’re like, oh, I was always selling. So what homeschooled allowed was freedom of choice of how you spent your day. Because school could be done in a very, like if you got like focused, done in a very condensed time, three, four hours a day. Get school done in the morning and then go live your life. So I was a weird first born kid that decided to start my own nanny babysitting business with that free time. So starting at like the age of nine, I was babysitting every single kid in my neighborhood, because you got paid great, and I had the availability to do it. So I wake up, get my school done, I’d be done by nine or 10, and I’d go work, because I like to work, and that then bought me drums. So what it instilled in me was an entrepreneurial mindset to be able to say like, this is what needs to be accomplished, get it done, and then you have this freedom to craft the rest of your life and what you wanna do. So in that season of life, it was being a nanny and a babysitter, then around 15 along came drums. So then if I wasn’t nanny or babysitting, I was playing drums. And when I moved to Nashville, it was nannying as a full-time job, but then drums as much as I could on the side too. And it was just because that’s how I wanted to spend my day, it’s how I wanted to spend my time. And my parents were like, great, as long as you got your math homework done, go, live your life, they gave us complete freedom. Like, car keys, like, go. They were like, you are fully enabled to go make the life you want, and if you wanna go make money, great. My siblings all have gone in their own different paths, but also really excelled, one that’s a, she’s a ballerina and a nurse. She graduated with her nursing degree at 19, rocked it, like very specialized, working for Vanderbilt these days. My brother was a hardcore wrestler and now manages a discount tire, which is a great career for a young guy, like absolutely crushing it. And my other sister is a CPA and a killer volleyball, like full ride scholarship volleyball. So we all picked like very different paths, but my parents completely enabled us to be like, cool, it’s drums, go, cool, it’s volleyball, go. Like, if that’s how you wanna spend your time, just do it to the best of your ability and how can we enable that? Manuel Martinez: And then also making sure that it sounds like you’re being taught time management skills and then that reward, right? It says, okay, being able to, and we have to do this a lot of times in work, in school and everything else, is okay, I wanna go do this fun thing or whatever it is that I wanna do, because it’s similar to you, I tell my kids, hey, my daughter loves dance, my son’s into wrestling and boxing, all these different things, cool, great, get this done or get your chores, whatever it is that has to be accomplished, finish that. And then after that, sure, I will go through and support you in whatever you want. But the other thing we taught them is you’re gonna finish it out. So like, if you’re gonna start wrestling, okay, you’re gonna do wrestling for that season, if after that you don’t care for it, that’s fine, but you’re not going to just quit and kind of make that quick change in the middle of the season. Rebekah Panepinto: Before you gave it like a fair chance. Manuel Martinez: Right. Rebekah Panepinto: Yeah, my parents are always like, it’s all in, especially like with our education, it was do a subject or a grade level of a subject to mastery and then you get to move on. So it was like, okay, like even if I don’t wanna do this, I’ve got to grit and bear it and like, you know, crush sixth grade grammar. And then I finally get to move on with my life. So it was a great, like I tell a lot of people, like the reason I think I’m so entrepreneurial these days is because I was homeschooled growing up and it was like, what do you wanna learn? Like there’s obviously baseline things you have to accomplish and testing and things like that. And I had to do what I had to do to get a four year degree, obviously, but still there was a lot of freedom in that to find purpose in things I care about, study subjects I care about, take the electives that I wanted, things like that. So I’m super thankful. Manuel Martinez: So then you get this internship, working in healthcare IT and is it what you thought it was gonna be? Rebekah Panepinto: It wasn’t and here’s the crazy part. I still was side hustling as a musician and I was in a band with this guy. We played every once a night, we had a standing gig. He was the CEO of a tech startup called G Squared Wireless at the time. And he knew I was not like digging project management. He’s like, I don’t see that for you. Like, so he actually one time just asked me to coffee, like outside of our normal gigs, like let’s just get coffee and let’s chat. His sales leader was stepping down and he’s like, I just was sitting there and the first person that came to mind was you. He’s like, it was really like an interesting thing because I’m not a salesperson. At the time I was not a salesperson. I was like, you know, 22, like in my first job out of college. But he’s like, yeah, it was just so weird. I was sitting there. I was like, I was like, Rebekah, be great at this. He’s like, so like, He’s like, so like, He’s like, so like, I don’t know if you have interest but I can tell you the intangibles and I can teach you the rest if you wanna come run sales for me. I was like, okay. I knew him, I trusted him. We’d been in a band probably at the time for like three or four years. Knew his sister real well. So it felt really low risk to me. It was like, okay, I’ll go try sales. Like, why not? So I took the job and I think I hit my quota in like the first eight months where he’d capped me even financially. I was like, well, okay, did that. And pretty much every sales job since I’ve followed my network and my relationships it’s all been somebody I know, like trusted, like him and said, hey, I wanna work for you. I wanna sell what you sell cause I can believe in it and stand behind it. And kind of funny how that works. And yeah, that was the last of project management for me but there still is a lot of project management I do as a salesperson. But I definitely was like, when I took the job, I was like, PMP, like I’m, this is it. I’m gonna be a 20 year HCA person, climb the ladder. And then my band mates like, nah, you should come sell. Manuel Martinez: You can do this. Rebekah Panepinto: Okay. And it all worked out. It was really fun. Manuel Martinez: And curious, what were some of those intangibles that he saw? Was it really just kind of your personality being able to speak, you know, and understanding. Like you said, you you have this alter ego or this other personality? Because a lot of times, especially at that young age and I’ve met people later on who like, they’re almost a little timid to try. So it sounds like a lot of your upbringing, just kind of the way that you were brought up to kind of say, I’m gonna give it a try because what’s the worst that can happen is I’ll go do something else. Rebekah Panepinto: Yeah, well, I think even just being a female drummer in a male dominated music industry slash my instrument of choice, made me realize like I can do anything a guy can do because tech and sales is a very male dominated situation. And so it was like, sure, like I can do this. Why would I not? Like that’s always been my reaction. A lot of cases like, why would I not be able to do this? Like let’s just try it. And he was opening a really good door for me. And I felt like in a safe and comfortable position, trusted his company, trusted his leadership. I was like, yeah, let’s see, we’ll go over here. Manuel Martinez: And some of that trust in the leadership is that also from him kind of running the band and knowing that a lot of– Rebekah Panepinto: History. Manuel Martinez: It’s that history, right? It’s that relationship we’ve already built and saying, well, if he’s doing it on this, it’s kind of like a side project where, I mean, technically he could be a little bit more of a jerk if he wanted to, but he wasn’t, especially just based on your experiences prior. So I’m assuming that had a lot– Rebekah Panepinto: Well, and that was still a gig. And so that still was a job. I still was getting paid. There still was a business element to it that he always delivered on. So I think that also like just had built trust over four years of like, I always got paid. I always knew where I needed to be. I know we always knew the set list. It was just like, he’s a good person that like has it together. And back to what you were saying about the Intangibles, I think one that he saw that I didn’t was the natural networking that I just naturally, no matter where I am on an airplane, a little less now in New York, like I’m not making friends on the subway, not that extreme, but always networking, always building relationships. Cause you never know like what those relationships could turn into. And that’s just my natural bent, my natural character and connecting people. And he just saw that I always did that. And was like, you know, like that’s a career for people. Brokering relationships, like they’re called brokers. That’s all they do. He’s like, oh, I never even thought of that. It was like a valuable skillset. Like I just figured everybody networks. He’s like, no, that’s yeah. That’s how you sell stuff. Like, oh, okay. Manuel Martinez: Originally you thought, okay, PMP, and you’re gonna, it seems like everything you do, I’m gonna go all in. So PMP, you’re like, hey, I’m gonna be a project manager. I’m gonna go all in. But then you went over to the sales side and I’m guessing, did you enjoy the project management side a little bit? And then was it when you got into the sales side, you’re like, oh no, this is my wheelhouse. It doesn’t even feel like work because I mean, like you said, it’s just that natural ability to just talk to people. Rebekah Panepinto: Yeah, I like now project management gets me to getting a deal done. So there’s an outcome that’s exciting and that can turn into opportunity financially, et cetera. Whereas just being a pure project manager is just like kind of turn and burn. There’s no real like celebration and upside in a lot of cases. I mean, in this scenario was a healthcare IT company, which is probably why that was to the extreme. But I feel like when I project managed really well to get a deal done now, I get the satisfaction of a deal done, of quota retirement, maybe a commission check. And so that makes it all more motivating to be even more detail oriented and have like a feeling of skin in the game. Everybody I feel like needs that to be truly motivated. I think companies that especially do project management well are people that can figure out how to build incentives to get people to be motivated financially to project management and things like that. That can be a conversation for another day because a lot of companies haven’t all solved that. But sales allows that skillset and that capability essentially to turn into like financial upside and actually like getting things accomplished. Manuel Martinez: And it’s one of those roles where it’s really dependent on you, right? If you are a little bit less, yeah, that individual contributor, like sure you’re part of a team and maybe all that, but as an individual, I mean, your compensation and how well you do is really based on the work that you do. And that’s something in a little bit of time that I spent as a sales engineer. I didn’t realize how much work goes into it. I thought, oh, you just show up and you just talk to them about the product. Hey, answer your questions and you’re out, but there’s a lot of work that goes behind. And if you’re not doing that, I guess it’s quickly, I guess not quickly, but over time you’re able to see the people that are putting in the work versus the people who are just kind of coasting by. Rebekah Panepinto: Yeah, or the fruits of your labor if you did it right. It’s same with running a podcast as you know, deal flow is guests, like basically lineup and making sure you’ve got your next guest in your next episode and things like that. Like you’ve got to constantly be, okay, who do I want to reach out to? Who do I want to have on the show? How do I want to structure it? You got to be thinking, you know, four or five, six weeks in advance, or else in four or five, six weeks, you don’t have anybody to record. It’s same in sales. It’s like pipeline. You got to be thinking of like, what am I gonna do in Q1? Who am I gonna talk to? Who’s gonna have opportunity? And it’s just a constant, like a little bit of always on feeling, but if you’re the right person, you enjoy that. And if that is missing, there’s a lot of like, what do I do with myself? Manuel Martinez: Right. Rebekah Panepinto: Because I’m always ready for the next thing. Manuel Martinez: And you said it, and that drew a good parallel is like even on the podcasting is also the results, right? Because people will go through and they will research. They’ll start to ask and talk to other people. And that’s something that I didn’t anticipate. And I was like, oh, I’m just gonna start asking people about the podcast, but just the amount of work that I was doing ahead of time prepping, so that when I did reach out to a guest, they’re like, oh, I talked to XYZ, or I talked to this person. And they said, it was such a great experience. And like, not even just sharing, but just everything that I had done ahead of time to prep them once I released the episode, after the episode, and just when I see them now, a lot of guests like yourself, like I met through this. So I think that’s been the biggest benefit to me is you talked about, you’re just a natural relationship builder. I didn’t expect that. Kind of, I’m assuming in your sales role, the more you talk to people, like you said, you establish your relationships, but they’re also kind of, they’re doing reference checks on you, okay, hey, is she just selling me something or is she really trying to partner with me to get me what is right for me, so that when I am somewhere else, and she comes and talks to me, I remember what you did to me last time. Rebekah Panepinto: Yeah, well, what I love too is like, in a lot of cases, I’m the first message when somebody loses a job or gets a new job. Like people at the CIO level, that’s pretty cool. They do not have to have me in their inner circle. I’m just their podcast friend, ya know. But I’ve had plenty of people be like, hey, I’m looking at this company thinking about going to do this as CIO, like what do you think? I’m like, it’s pretty cool. It’s again, trusted advisor level relationship that is developed and not just a transactional approach. So it’s just, yeah, it will never be me. Even though I think of it like that, I think of a pipeline, I think of like, I need more guests, I need this, I need four episodes in the queue, but it’s still not losing authenticity. And the fact that there’s just still a machine and a project management element that needs to happen just to get stuff done. Manuel Martinez: Right. And there’s still a process that has to happen in the background. That doesn’t mean that the conversation that you have with them is any less authentic. Rebekah Panepinto: Yeah, or the person, yeah, being a part of, them being part of the machine does not like at all devalue what it is that we’re building together. It’s just there has to be structure in order to get work done. That’s just kind of life. Manuel Martinez: So then that first sales job, what are some of the skills that he taught you that you didn’t have or you didn’t think, or maybe you did have, but he just kind of helped refine over time? Rebekah Panepinto: Learning the product was where we spent the most amount of time in any company. I think that’s where it’s really important to start, is really know your product inside and out. And like, what’s a good customer and what’s not? Because bad customers are miserable. And so it was like a really cool way that he took me about it even was how he had become the CEO of the company. Because he had started just as like a help desk agent for the company. And he had worked his way up over the years to become the CEO. And so he said, you need to go work every job in the company so you know what we do. So you know how the calls are answered by the help desk agents. So you know what customer success looks like, all these things. So that was like my whole first month. Like every other day I went and worked a different job in the company and like literally sat shoulder or shoulder with someone like, how do you do this? How do you do that? And just learned the product. And then I could start selling it. And then together we started to understand like what was a good customer, ideal customer profile, things like that based on their book business they had to date. But the most important thing was just understand product. Get that really down and make sure you know who’s gonna be the right fit for it so that there’s not heartburn on even both sides in some cases. Because there would be some customers that people would be like, can we fire them? Like it wasn’t worth it. These help desk agents were like losing their minds because this customer was so ridiculous. And you just don’t want that. Like a win-win is a successful customer really truly the good fit for what your product does. And then together it can be a long-term partnership. Manuel Martinez: So then you pick up these skills, you’re starting to say, hey, you know what, sales seems to be for me. You’re hitting your quota, you’re maxing out. And then what makes you decide to then stay within the sales role, but then kind of say, all right, it’s time for me to move on. Like I’ve done everything I can here. Rebekah Panepinto: Probably being capped if we’re honest, is why I was like, I’ll see what else is going on. I later learned that in a lot of cases you don’t get capped. I was like, oh, I didn’t know. It was my first sales job, I didn’t know. So when I saw there was higher earning potential, I was open to other people had to offer. And again, in the same case of having this great relationship with the CEO of that company, I had a great relationship with a president of a small dev shop that was looking for his first salesperson and he’s like, I think you’d be great. Want to come work for me? I was like, sure. I kind of again felt like nothing to lose. I mean, get better comp plan, selling software versus what I was doing with the help desk piece. I just got more broad. And so I could sell mobile apps and websites and enterprise software and just let me, like at the time I now know like not everyone is a prospect. But the time my sales brain was literally everyone’s a prospect. Like why would I not talk to everyone on every single flight and every single elevator? Because everyone could want a mobile app. So I was like, okay, let’s go do that. And that was really fun because I had an opportunity, though the company actually is no longer in business, but in that window of a good couple of years, I had the opportunity to be the face of that company in the market. Everybody thought of me synonymously with the time it was called Pilgrim Consulting. It was Rebekah Pilgrim Consulting, Rebekah mobile apps, Rebekah websites, because I just was everywhere. Now looking back, I don’t think I could even keep the schedule I had back then. Like I would wear myself out and probably was wearing myself out back then, but I just was like so motivated. You know, I started making the most money I’d ever made company car, company paid cruise. Like it started to get ridiculous for a 20 something year old. But I was like, I’m selling stuff like this is fun. I want to get up and sell more stuff. So that was really fun. And looking back now, I see how small of a pond, you know, I was really fishing in when I felt like it was like, this is a big thing. Like some of my big customers back then were companies that nobody even knows about or, or no longer even in business. But at the time it was just like, the world is my oyster. Everyone can buy from me. Like, let’s go. And that was really fun. Manuel Martinez: And I’m sure later on, as you started to, cause you talked about it right now, is not everybody’s a prospect. Like when you first get into it, like, yes, this could help everybody. But that’s a skill that takes a little while. And I’m just curious how long it took you to develop is that filtering. While yes, there’s the potential, especially like in a software building websites, there’s a potential it could be for everybody. But then there are, I’m gonna say filters where, okay, yes, we could help you. But the amount of effort that it would take is just, it’s not worth it. Like you talked about some of those bad customers where it’s just, it’s more work than it’s worth. And then there’s other ones where, okay, maybe we’re selling them something, but they’re not using it, right? So you kind of have like the opposite ends and it’s really trying to understand that because that’s something that a lot of times people are like, well, this can help everybody. It can, but does it really? So how did you kind of develop that skill? Or is it just something experience over time that just made you realize, yeah, I need to do a better job of asking the right questions or how are you going about filtering them? Rebekah Panepinto: It was definitely the next job that made me realize I had a smaller pool. So we can get to that in a second, but in the case specifically with what was going on in that situation, we did say yes to everything. And then there was a lot of fires and there was a lot of headaches and there was a lot of threatened lawsuits. And I probably would have eventually led to the company having to unfortunately close their doors. I was gone by then. So I don’t know exactly what all had gone on, but I’m sure bleeding money on bad customers could not have been good for the longevity of the company. But I went from there again was recruited away by who was the, I can’t remember what his title was now, but head of business development. Maybe we call them like SVP business development for a group called E-Mids, which is healthcare software consulting. And so that took me from just like this little pool of middle Tennessee that I can sell all software, all mobile apps, whatever, to now global, but only healthcare software. So now it was on planes. I went to India twice, London. That’s what started getting me to go to New York a lot back in the day, opening my eyes to like a much bigger world. I was like, whoa, I can do business. Like literally the whole world, but only healthcare software consulting. Like only EMRs, health tech companies are gonna do business with us. And so that’s when it started to get really narrow. Like, okay, it’s gotta be the right size of company who’s open to outsourcing, who needs XYZ solutions. There who’s gonna buy for me and they’re ready to spend my time and I need to hop on a plane to go see. So that started to make me realize like, cool, it’s a bigger world, but our customer pool is a lot tighter and the CIOs and CTOs are a lot harder even to get to than run into somebody on airplane. Like it just wasn’t that easy anymore. Manuel Martinez: And then so you go into a bigger pool, right? But at the same time, it sounds like each one of these roles as they’re starting to get a little bit bigger, but maybe a little bit more specialized, you’re having to kind of go through it, put on that Rebekah charm and really get them to open up and in this big of a space, right? Like you said, hey, you’re going to London. People in London don’t know you from anybody else in healthcare. So how did you handle rejection? Because I’m guessing there’s a lot of no’s and for some people like that can be like, oh my gosh, like they take it very personal. You don’t strike me as the kind of person that does, but maybe you did and maybe that drove you a little bit more to like, no, I’m going to get that yes. There’s both aspects. Like some people take that no and they’re like, all right, well, I’ll go somewhere else. Or some people are like, oh, I’m going to get that yes. Or maybe it made you also realize that, okay, there’s a no for a reason. Like it’s really not that fit. Rebekah Panepinto: I think dealing with rejection is a constant growing opportunity for everybody. Like for me every year, I’m like, how do I get better at like being able to take it on the chin and move on? But in that case, for that specific role, I just got really good at tracking my activity. And I knew that if I put in certain inputs and did certain activities like LinkedIn outreach, networking events, conferences, a lot of that, I knew I’d eventually get the win that I was looking for. So I became known by my then he became my boss, sales engineer, like my whole team that we kind of built around what I was trying to do. And they all were like, well, Rebekah, we’ll get you in. It didn’t necessarily meant I always got the deal. It didn’t mean I would like get a win, but I knew with my activity and with wearing it out and with telling enough people like, hey, I’m coming to visit you in Chicago that I’d get in. Eventually somebody would take a meeting and I would get a door open and then we could do with it what we pleased once we were in. But I just knew like, you know, 30 InMail at the time, 30 InMails a month, telling people I’m coming to visit, offering coffees, like eventually somebody will say yes. It’ll be one CIO we haven’t talked to yet. And the team would celebrate that. They were like, she got us in because nobody else could get us in. So that was really good, especially when I would get tired of the like, every month you start over, I just knew to go back and check my activity and just like, if I stayed true to it on the other side, I would get, you know, the least activity wins I was looking for, which then eventually would lead to actual opportunities and deal flow as well. Manuel Martinez: And it’s funny you mentioned that because I just finished reading a book. It’s The 12 Week Year. Rebekah Panepinto: Oh yeah, I’ve heard of. Manuel Martinez: Yes, and basically one of the concepts and it sounds like you implemented this is basically each week is a month, right? So you’re condensing a lot of your activities, but the key point of it is tracking what you’re doing looking back and reflecting here, you know, because the week is the month, right? It’s like, okay, what are the activities that you did that week? Okay, compared it to the previous week. Did you do more? Did you do less? And they don’t focus so much on, like you said, on the outcome. It’s like, hey, we got the deal done. It’s, okay, I got in. And it’s, you can only, you can only in, or affect what you’re doing, right? Like if you’re putting in the activities eventually, like you said, it will lead to a win. It may be later on, it may be sooner, but that’s all you can control. You can’t control the outcome. You can only control the inputs. Rebekah Panepinto: Activity. Manuel Martinez: And again, kind of going back, it sounds like that’s just, is that something again from kind of the homeschooling from the get-go? It’s just like, I know that if I do this, it frees me up to eventually do something else. Or does it also kind of just that persistence because it sounds like the homeschooling didn’t do it, but I’m gonna take drumming into account is the more you practice, the better you got, the more gigs you landed. So is that just something that over time, again, not that you consciously thought about it, but do you, the rewards, do you think that that’s what got into it? It’s like, okay, I’m not gonna get the reward now, but it might come a month, two months, whatever time in the future. Rebekah Panepinto: Well, and I think I’m just a doer and like somebody that’s gotta have a busy schedule and I have a lot going on. And so, if I can be in situations where I lead myself to open it to opportunity, like why would I not walk through that door? And so I have every opportunity that has been presented to me through interesting ways. Like we were talking about, I just did the Macy’s parade last week and that came through a Spartan friend of mine. We were running Spartans together and he said, “Hey, what would you think of being a balloon handler in the parade every year I’m a pilot and can use some good handlers?” I was like, why not? Here four years later, I’m a balloon handler in the parade every year. Like who would have ever thought? But I was just like, why would I not open myself up to opportunity and I’ve built this friendship through a mutual hobby that we enjoy and now we have another one that we share. Just like, just walk myself into wild, crazy opportunities. Manuel Martinez: And we talked about that before, right? Is kind of prior to filming is you do a number of things like Spartans, the balloon handlers, you travel and you do a number of different things. You’re not against trying new opportunities. I know you said like, why would I not? But also I guess the reversal of that, but like, well, why would you? Like what benefit do you get by being a balloon handler at the Macy’s parade other than being able to tell a cool story? Rebekah Panepinto: Oh, the experience, man. It’s so fun. This is the best way to spend Thanksgiving because all these people are just like in awe at this balloon coming down, you know, Sixth Avenue, which is pretty fun. But the people you meet along the way, I’ve met other super interesting people who all have like, cause it’s a volunteer thing, all have real jobs that lead to other cool opportunities to people I spend friends giving with. And just like you kind of follow the trail of just like interesting people introduce you to interesting people and interesting hobbies. And next thing you know, it’s like, it could be something that benefits your career, which is crazy. And maybe it doesn’t always benefit your career, but like, we’re not robots. That’s not the only reason we’re here on earth to, you know, work. So there’s other areas like it brings fulfillment. And in that case, especially with the balloon handling, I’m pretty cool to my nieces and nephews when I’m on Shrek or Bluey, you know, they’re like, what? I’m like, okay, if she wins me aunt points there alone, it’s worth it. So it’s always a nice adventure. It’s fun. Manuel Martinez: And is that something you always try to maintain? Cause it sounds like, I mean, you’re full-bore in anything that you do, but at the same time, you also kind of are open to doing stuff like outside of work. Like it’s not just work all the time. Like when it’s work, it’s work, but when it’s not, like. Rebekah Panepinto: I think it makes you a more well-rounded person. I can’t even keep track of how many people I work with or have done business with that come run Spartan races with me, people that I’ve done podcasting collaborations with and worked with who want to go scuba diving together. Like people that share the same hobby. It was actually weird. I had like three or four episodes in a row where I talked to a CIO about scuba diving. I was like, who would have thought? Like I had this very similar hobby to these CIOs and again, it makes me memorable and it’s another way to connect. And I’m sure one of them all eventually end up on a dive with. So I think like it helps other people see you as a human and just helps you connect with people in other ways that then gives you a longevity to the relationship where again, it’s out of that transactional and it’s into like, no, I actually like you. Like one of my customers today, first thing, we needed to talk business. So we got there, but first thing he was like, how was the parade? And he’s like, we watched for you. I was like, that’s pretty cool. Like that’s fun. It just makes you different. Again, I love the word memorable. Like that comes back to even what we were talking about earlier with like in that first interview ever for HCA to be a project manager, like me being a drummer made me memorable. So it helps stick in people’s mind. And I have plenty of hours in the day to do everything that I wanna do. And then when I don’t find it fulfilling, then I can retire something. And part of it, let’s be completely honest too, comes down to personality. I’m a seven on the Enneagram and it’s just, it’s always what’s next. Manuel Martinez: That’s awesome. Rebekah Panepinto: It’s just how I lived my life. Manuel Martinez: So then as you’re going through and continuing on within your career, what is it that led you into that next endeavor to say, okay, is it the fact that you get so well and you know everybody within like the healthcare space that the challenge is gone? So now you’re like, you need to move on to the next one because it sounds like you and I share that trait where you’re like, okay, I’m capped or like I either, I’m not earning more or I’m doing really well but there’s nothing to kind of challenge me. I need to go find something else. Rebekah Panepinto: Yeah, so two things that happened when working for this group called Emids was that my eyes were open to how big a world was out there and how niche being in just one industry can really be. When you were used to being like everybody’s a prospect and now you’re really niche, it’s like, ooh. So I was aching for bigger city, bigger territory, bigger opportunity and widening my kind of reach again. And so then came the opportunity of even the world I still live in today of the channel. So good old AWS, Amazon. That first job outside of Emids was the first opportunity to go sell on the channel. It was with a multi-cloud group but my boss there actually is still my boss today. We followed each other through a few different companies which has been fun and it opened up my eyes to wow, like I can serve a ton of industries. We’re just staying within the Amazon stack and it also relocated me to New York which opened a whole nother world of possibilities without having to be on a plane literally every week. And so I jumped to the opportunity. It was again through my network, through relationships. Somebody said I had this opportunity when I come along. Story of my life and it was like, yeah, this sounds like a really cool chance to grow and learn the channel and get on the cloud train which is obviously still serving us both very well today. Manuel Martinez: And you mentioned you have these relationships and you’re going through and you’re kind of delivering. So what is it about not only you but the skills that you’re developing to kind of continue to develop these relationships? So it’s one thing like, hey, we have these commonality but when it comes to business, right, there are specific business outcomes that you’re helping deliver. Now I just saw somebody post something and this is what kind of made me think about it is you can say, hey, we’re gonna do this, I’m gonna do this but if you don’t deliver over time, that starts to erode. Now, how do you go through and make sure that you’re delivering? I know that you’re doing your part by closing the deal but there’s a lot that goes on behind the scenes. So is that where that project management part comes in to make sure it says, I promised this, I’m gonna make sure that we at least deliver this. If we can do more, great but at a minimum, I have to continue to make sure that I deliver on what I promised. Rebekah Panepinto: Well, it’s not always worked out, like to be completely honest but that’s where having a personal brand and being able to, to an extent, separate myself from the company when things like that happen has actually served me well and how I’ve gotten CIOs who, it did maybe go bad somewhere, willing to do business with me again somewhere else because they knew like I did all I could within the resource situation I was in with the company. They could tell typically where things fell down, maybe even not immediately but like a couple of years down the road, it was like, it really wasn’t a Rebekah issue. That was a XYZ company failure. So there’s been a good way of building my own brand and building a relationship with my customer. That’s not just being part of the machine of the company that I work for so that they trust me and they know like they can give me a chance somewhere else and like, we’ll get it right, we’ll do the right things because in the end, like everybody’s human and things happen and obviously if I moved on to another company, they can kind of put two and two together. There probably was a reason and you know, give me a chance to earn their business back again. But as much as I can, when I am involved in being able to make sure a project is done to the best of our abilities, I’m all over it. Like I can be slightly obnoxious and I’m with my SAs. I don’t know everything that’s going on. With my customer and Slack every day, I’m usually as all over it as I can be. There’s just sometimes mistakes happen and we all learn and life goes on. Rebekah Panepinto: You mentioned Slack and kind of talking and communicating. What do you think is one of the biggest benefits of being able to communicate properly? So, and I would say, you know, Slack and I guess within your communication, like how do you balance, you know, that, hey, this is Rebekah and you know, hey, I do the Macy’s parade, but also this is Rebekah and I’m professional and I know how to communicate properly and be able to delineate that because I’ve seen people that are good at that, that can, hey, I know what that right level of each of those is and I’ve seen somewhere like that personal gets mixed in too much on the professional. So how do you balance that? Rebekah Panepinto: Well, and I’ve been friend zoned sometimes from that too. And then it’s like, this person is just not in business with me, like it’s okay, we can just be friends and we move on, but it’s just knowing your buyer and your customer. Like there’s other people within the same company that I was talking about the parade with this individual who would have zero interest. And so I would not even volunteer. Like I know they don’t care how I spent my Thanksgiving. So just don’t even go there. But this person wanted to have that conversation, which was really fun. And I was like, sure, I’ve got pictures and whatnot. So it really comes down to like a person to person just situation. And then I like to always hit people through different channels too. So like if it is email or a phone call or on a Zoom call, like usually we’re just getting stuff done. But if I’m just saying, hey, on LinkedIn or interacting with my podcast, like it is a little more like we’re just getting to know each other for lack of a better term. Like this may or may not turn into something down the road. But at least like they’re seeing me, they’re thinking of me. They know I ran a Spartan. Like it’s just another touch point so that I’m top of mind for somebody. When I do reach out and it is the right time to like, okay, now let’s talk about a deal. So it’s totally a case by case basis. I don’t know if there’s like a right or wrong answer. I’ve probably missed it many times. But I would always choose a quality relationship with someone over like getting too in the weeds transactional. Like I don’t want anybody to be like dreading my outreach because they know I’m only calling for the check. I want somebody to still think of me as like, somebody they want to hear from. Manuel Martinez: It goes back to being memorable, right? I want to be remembered as somebody that can do both. Like, okay, when it’s business, it’s business. But when it’s not like this is just a person that I enjoy talking to. Rebekah Panepinto: Yeah. And you never know, again where that relationship could lead. People change jobs. I change jobs. Like, you never know. Rebekah Panepinto: And are you a big reader? Like, as you’re developing these skills, like do you, I guess, how do you continue to develop the skill set? Like, do you read? Do you, is it just, are you one of those people like, I’m just going to learn on the job and, you know, from every mistake or from every win, like there’s something to take away? Like, how do you continue to get better? Rebekah Panepinto: Podcast addict. So yes, I read, but through audio form. So I love Audible and then like, I mean, an hour podcast at least almost every morning will I get a workout in. I love podcasts of all kinds of topics though too. Because even if I’m listening to somebody else’s podcast that’s on finance, I’m hearing how they run a finance podcast and learning like how they do their newsletter. And like, a Ramit Sethi, I’m a huge fan of like, watching how he’s built his, it’s called Money for Couples now, it used to be called I Teach You to Be Rich, how he’s built that little empire of his own. It’s super cool. And then along the way, I’m learning about more financial literacy and like, it’s opening my eyes to really cool ways to build wealth and things like that. So every morning it’s about an hour on a podcast. It’s not always, you know, sales or business oriented, but it’s typically along those lines. I’m not usually going too far off the path. And I learned little things, little nuggets, Tom Billew Impact Theory is another one I love. He has great takes on the world and has built a multi-billion dollar business and sold it to Atkins Quest nutrition, he sold to Atkins and done very well for himself. His podcast also, I think it’s like top three in the world. So I like to just take in that content as I start my day, every day, and then little blurbs around, you know, throughout the day, can give you a little insights and ways to look at things. Manuel Martinez: So it’s just that continuous, like you said, you like to kind of be well-rounded. So, you know, hey, finance, but sure, there’s things that apply to business. You’re not going way off on like a, maybe occasionally you’re like a mystery crime thriller or something like that. Rebekah Panepinto: Those haven’t hit my Spotify, what is it, Spotify wrapped? They’ve all been pretty much, yeah, still a business flavor. Cody Sanchez, love her. Yeah, all my audio books are like Grant Cardone’s of the world, Alex Hormozis. They still kind of all keep that same theme. Manuel Martinez: But just picking up something different from each conversation that they have. Rebekah Panepinto: Just like, yeah, who’s interesting, who’s got a good perspective on something. Yeah, where do I feel stuck? Like I’ve gone through times where like dealing with rejection is like a big thing and I’ll go read books. On like, how to get stronger and like deal with rejection. I can’t remember the title of one book that’s really good and that Tom Billie loves, but I’ve gone to read it before. Antifragile, just came to me. Manuel Martinez: Antifragile. Rebekah Panepinto: Antifragile. That’s big on like making sure like, you know who you are, you have purpose so that you can be antifragile in this crazy world. So I’ve gone down paths of like, this is really where I need to get some support right now. It’s probably a little bit of a homeschool thing. It was just a constant hunger to learn. My parents taught me how to learn and how to enjoy learning and how it’s a lifelong journey. It’s not just like cram for your test, get a B and move on with life. Like, no, I actually want to learn and master something and add it to my repertoire. So I’m like that in other areas of my life too. Like when it’s right now scuba diving, it’s like, I want to go get my advanced cert I want to go all in. I want to go dive the great blue hole. Like it’s just like, it’s all in and then, you know, might not dive as much after all that. Who knows? I’d be surprised because I am enjoying that hobby, but it has some flows. Definitely not racing obstacle course racing to the level I have in the past, because I’ve done most of the major courses. So you pivot to find something else to go and check more off my list. Manuel Martinez: So then, sounds like you’ve gotten pretty much, and I don’t know if I’m correct, but with the person that you’re working for now, it’s a different role, but I mean, it’s the same person and you’re pretty much at where you’re at now. Rebekah Panepinto: Yep, Artisan Studios, yep. Manuel Martinez: So normally I do this at the beginning of the conversation, kept going. So what is it that you currently do? So a lot of times I ask the guests is, you know, like who’s Rebekah and what does she do, right? We got into where you were at and then just kind of conversation flowed. So what is it that you currently do? Rebekah Panepinto: Yeah, so day to day, we are an AWS professional services partner. So 145 ish strong doing all of the fun, agentic, generative, professional service oriented work to side by side with Amazon reps help their customers succeed. So within the AWS ecosystem, obviously it’s big on compute and a lot of folks are working on EDPs and PPAs and just managing, you know, how they’re gonna contract the actual business with Amazon. But in a lot of cases, like if somebody wants to build something, they need a partner to help bring things to life. So that’s where we get introduced to help customers. We call it dream a little dream. We do something called a challenge 24, where my CEO will come and whiteboard with a customer for literally 24 hours. So three eight hour periods over three days, just locking folks in a room and said, hey, if you can have anything you wanted, no resource constraints, no money constraints, like let’s dream together. And then from that, we can find tangible things that we can actually build a product around. So Chick-fil-A is one of our big anchor clients. We’ve been doing business there for over eight years, completely rebuilt their supply chain on AWS. Then a ton of other retail CPG folks. Now we’re servicing through professional services, but also out of the Chick-fil-A relationship, we’ve productized different company solutions. Edge, for example, we’ve got a generative AI solution, Agentic AI solution, that they’re kind of pre-packaged as an accelerator to help our customers to be able to build faster and go to market with a solution versus having to build completely from scratch because once you’ve solved Edge or agentic in certain ways, it’s just pivoting for the use case for the next business that needs it solved. Manuel Martinez: And what I was gonna kind of ask this earlier, I don’t know at what point you decided to kind of start the podcast and what is it that, I know it’s focused around digital transformation, but what is it that really called and said, “Hey, I wanna talk to more of these people and learn more about what they’re doing.” Is it similar to that like, “Hey, dream a dream,” and it’s, you know, are you still just collecting information? Is it, you know, “Hey, I like talking to cool people,” like combination of everything? Rebekah Panepinto: Yeah, well, I’m definitely trying to figure out where it goes next. So an interesting place of like, how do I kind of take this next level? But the origination was out of COVID and how am I gonna sell stuff? Like I’m locked in my 900 square foot apartment in New York and people aren’t meeting, like, how am I gonna do this? I gotta go virtual. I gotta build relationships virtually. And there was a person, I was working for Rackspace at the time, who was like the chief product content guy and kind of showed me the ways of how to, you know, get the camera, interview people, and just like, “This isn’t that hard.” Like you just kind of gotta do the work and just be focused. And so I started it in the like height of COVID. Rackspace was super supportive, which was super cool. And now my current company also is very supportive. So in every iteration, it’s been almost four and a half years now. I’ve had support, it’s opened doors, I’ve met interesting people, and I’ve started to build a following enough that I’m like, “I should keep doing this. Like, why would I not?” Because it also really solves for my creative outlet. Since I don’t play drums to the extent that I used to, like I mean, I used to do three or four gigs a week, it’s a really good creative outlet for me to still get to play with, you know, all the gadgets and just have interesting, yeah, relationship building conversations. So I’m figuring out what it looks like next, now that I have a baseline of a really neat audience that’s pretty engaged.
Networking Your Way Into Your Dream Role with Chelsey Bonilla | Ep054
Episode Information Show Notes Breaking into a major tech company requires more than submitting applications online. Chelsey Bonilla shares how strategic networking, intentional preparation, and genuine curiosity helped her land an account executive role at Gartner, despite not having a traditional technical background. Guest Background:Chelsey Bonilla is an Account Executive at Gartner, one of the world’s leading research and advisory companies. A Las Vegas native and UNLV double alum, she built her career through operations, IT staffing, startup experience, and project management before finding her current role. She’s an active member of SIM (Society of Information Management) Las Vegas, where she volunteers and builds relationships within the tech community. Episode Highlights: Non-Traditional Path to ITChelsey’s career didn’t follow the expected route. Starting in operations and moving through various roles, she found herself drawn to IT despite lacking technical credentials. Her willingness to ask “I don’t understand” became a strength rather than a weakness. Strategic Networking That WorksWhen Chelsey became obsessed with working at Gartner, she didn’t just apply online. She researched everyone attending a SIM networking event, showed up early, and made genuine connections. That preparation led to a phone call about an opportunity that wasn’t even posted yet. The Power of PreparationBefore networking events, Chelsey researches attendees on LinkedIn, follows them strategically, and comes prepared with questions. She calls it “cyber stalking”—and it works. Surviving Seven Rounds of InterviewsLarge organizations have rigorous interview processes for good reason. Chelsey shares what it took to get through seven interviews at Gartner and why each round reinforced that she was on the right path. Key Takeaways: Ask questions freely, even when you don’t have technical knowledge Prepare intentionally for every networking opportunity Build genuine relationships within professional organizations Research people before you meet them Trust the rigorous interview processes at companies you admire Give recruiters the information they need to advocate for you Volunteer and give back to your professional community Connect with Chelsey Bonilla:https://www.linkedin.com/in/chelseybonilla/ Listen to Career Downloads:Available on all major podcast platforms TranscriptionManuel Martinez: Welcome everyone, my name is Manuel Martinez and this is another episode of Career Downloads where each episode I basically hit the refresh button, bring on a different guest to learn more about their background and their experiences, to really try and uncover any actionable advice that you can use as you’re managing your own career. So I’m excited for today’s episode because I have with me Chelsey Bonilla and her and I have, over the last, probably close to a year now, have developed a both professional and personal relationship, just kind of getting to know each other. And ike I’ve mentioned before, there’s different areas of technology. So she didn’t feel that she works in technology, but she really does. So again, I just kind of want to help, I hope that her story kind of helps dispel some of those myths. And we get to learn a little bit more of how she’s navigated it, and hopefully find some things that will be helpful for you. So with that, I’ll go ahead and introduce Chelsea. Chelsey Bonilla: Thank you, Manny. I appreciate all the time and consideration and overthinking that you’ve allowed me to have over the last year. Manuel Martinez: And I appreciate that it kind of, it took time because you’re not the only person that, it takes a little bit to be like, “Well, wait a minute, why me? Why my story?” it’s not something that you do all the time, right? I don’t see you on podcasts all the time or kind of speaking out publicly. So I think this is good because I’ve had a couple of guests like that. And it it helps other people see like, “Okay, it’s not just me.” Chelsey Bonilla: Right, yeah, absolutely. I mean, we met for coffee, you emailed me questions, we had in-person conversations. So on the scale of overthinking, I think I’m on the high end. So I appreciate you indulging me throughout the year. Manuel Martinez: No problem. So if you don’t mind as we get started, if you just kind of tell me a little bit about where you grew up and then eventually kind of what led to you starting your career. Chelsey Bonilla: Absolutely, so I love the story of where I grew up because I actually grew up in Las Vegas. So born and raised never left. And I like to say that because growing up in Vegas, born and raised here, not very far from where we are right now, I’ve kind of seen the growth of the city, seen the change of the environment, but I’m also a double alum from UNLV. And I knew coming out of high school that I wanted to go to UNLV. And when I went back to get my MBA, I knew UNLV was where I wanted to go. And that never left, not to say if someone leaves there’s anything wrong with that, but a lot of people that I grew up with left to UNR, left out of state. And I just, I truly have an affinity for Nevada. And I knew UNLV was my school. So that’s kind of my education. And then starting in my professional career, I started working at the young age of 15, which is crazy to say. So I started working at 15. I worked for a small mom and pop shop here in Vegas, a school uniform company. And I was the right hand to the CEO. So I would do everything from payroll to training, to hiring, to operations, to, I was the controller. I would do bookkeeping. So it was this amazing experience to get exposure to business. 15 to 17, I was basically supporting and helping from a business perspective. So then when I started at UNLV, what am I gonna do with the rest of my life? I naturally gravitated towards a business degree. So I graduated with a bachelor’s degree in business. And it was amazing because I would take these concepts from class, I would come back to the business and say, “Hey, what if we tried this? What if we created a social media account? What if we did marketing campaigns? What if we changed the way our strategy looked?” So it was this amazing playground where the CEO would let me come back with concepts and kind of grow those organically within the business. And then when I graduated with my bachelor’s degree, working through the entirety of my bachelor’s degree, going back to school, I knew I wanted to get my MBA. So I went through the executive MBA program at UNLV, which was great because it was unique to the standard MBA tract because I was with a cohort. So I was with 18 other individuals who are still friends to this day, seven years after graduation. And it was just such an eyeopening experience that really led to my journey and the evolution of my professional career. Manuel Martinez: What is it about that CEO? And do you think it was just them kind of seeing you grow up and knowing that you’re pursuing this business degree, that they gave you the ability to kind of implement a lot of these changes that you wanted to go through because sometimes there’s business owners or just maybe the businesses, it’s so established that they’re like, “No, we’re not gonna do that.” Or, “Hey, that’s great in theory or in a classroom that would never work in an actual business setting.” So is it you communicating, not just like, “Hey, we should do this,” because I’m sure you weren’t just like, “Let’s implement this.” And they were like, “Sure, let’s do it.” You had to kind of build a business case. So what was that kind of interaction like? Chelsey Bonilla: Yeah, that’s a great question. And I love the term business case because I think as IT professionals, we use that all the time. And thinking back 15 years ago, I didn’t even know I was building a business case to why should we do this? So there was a lot of trust that the CEO had in me I think because I was with the business for so long. So I ended up working there for 10 plus years. And just over that time, it allowed me to build that trust with her. So I could come and I could say, “Here’s an idea. Here’s what I’d like to implement.” She was great at building the business, but she didn’t have the college education. So me coming with, “Hey, this is what I’m learning at school. I don’t know if it’ll work, but maybe we could try it.” And there was a lot of freedom for me to kind of try different things and work with the team and say, “Hey, let’s try this. Let’s see if it works.” So like building employee manuals was something that I had so much fun with. And it was the first time the organization ever had an employee manual. So it was like that compliance and that documentation was things that I was learning that I could bring back and then were valuable to the business. And she saw the value as I would execute on those things. Manuel Martinez: And my guess is though, that not every idea was a success. Chelsey Bonilla: Absolutely. Manuel Martinez: And when it didn’t, how did you Did you take it personal or kind of, it sounds like you had a good relationship so that when it didn’t work, how do you determine, “Hey, this isn’t working as opposed to, we just need to keep trying harder.” Chelsey Bonilla: I’m definitely the beat a dead horse. Like there’s nothing I can’t try hard enough to accomplish. But I think the older I’ve gotten, the better I’m at at taking constructive criticism. But there were multiple times where I was like, “Well, maybe we just tweak it slightly, or maybe we try it differently.” And I still think it’s gonna work. And there would be times where it’d be like, “Well, let’s table that idea, but I’m not gonna let it go. But we’re gonna bring it up in the future. But I understand it doesn’t make sense for the business at this time.” So there were definitely those moments where I had to let things go. And that was definitely part of the learning experience. Every idea is not gonna work and it’s okay to fail. And it’s okay to grow from those failures and make changes. Manuel Martinez: So then now you’re working here for 10 plus years. You basically grew up here. You’ve learned a lot both in school and in practice, which a lot of times people don’t get, right? They’re looking for internships. Now it was a small business, but I think it gave you the flexibility to kind of tweak and learn a lot of that. So what made you decide, “Okay, it’s time to kind of leave this environment where I grew up and try and go out for my next venture.” Chelsey Bonilla: So that was, I would say, a key part of the Executive MBA. So going into the Executive MBA, you go through an interview process, you have to have 10 plus years of management experience. And I was the second youngest in the cohort of 18. And I was, I think, the only one who had only had one job. So it was incredibly eye-opening going into the MBA and just seeing the scope of work that people had gone through and the different industries and the exposure that I had. And it was one of those moments where your eyes were open to the potential of the world and you kind of couldn’t go back. So going through my bachelor’s degree, I was working full-time at this operational job. I was a server off the strip, paying for my education. Going into my MBA, I had to take a step back and just focus on work and school. And then when I graduated, it was kind of that what’s next. And I remember going to a networking event at the end of my graduation. And there was an entrepreneur there. And I was the first one to the party. I always loved being on time. We had a conversation right when I walked into the party and he goes, “Okay, you graduate with your MBA, what’s next?” And I said, “I want more. I just don’t know what more is.” And he handed me his business card and said, “Send me your resume, I’d love to talk.” And that naturally led to me jumping into IT. So I left operations and I joined this entrepreneur, CEO, who was managing his own family business. And he was an entrepreneur for the entirety of his life. So I was the chief operations officer for that organization and we would develop different products. We’d monetize them. We would pitch them to investors and it was just a total whirlwind. And I had no experience in IT. So I remember having my OneNote with all my IT acronyms, no idea what anybody was talking about half the time. I would Google at the end of the night, what does Scrum mean? What is Agile? And I was managing a team of developers, which is crazy to think, not really knowing some of these methodologies, but understanding operational and business processes and then learning IT along the way. So that was my jump from small business into startup and IT. And it was just a crazy experience from there over a three-year period. Manuel Martinez: Going and being, overseeing a bunch of developers, right? And not having that background. But one of the things I think is probably important there and it sounds like, especially if you’re developing, you know, employee manuals and things, you know, at your previous employment, is that kind of what this person saw in you and said, “Okay, they figured IT and I’ve seen this now more throughout my career.” You know, people think, “Oh, well, I don’t know much of, you know, I’ve been in IT, I’m a network person, I can’t go to security or I can’t go do this.” But if you’re a person who likes to learn, it sounds like you did a lot of that. It’s the people part that is, sometimes it’s a little bit harder to teach. So they saw that, “Oh, she has, you know, communication skills, obviously you made a good impression.” Do you think that’s what led you there with him? And then he said, “She can learn the IT stuff.” Chelsey Bonilla: Absolutely, yeah. He had been in IT, still in IT for the entirety of his career, but the people skills, the time management and managing teams, I think was the key pieces that I had. And he’s also the visionary, so he would have these big grandiose visions, and this is the idea, and execute. And I was and am very good at taking, okay, I hear you, but now we need to build a step-by-step plan, and how are we actually going to execute on this vision? So I think that was the key piece from an operational perspective that allowed me to succeed in that role. And a lot of people don’t love the compliance and the documentation and the note taking, and that is my bread and butter. I love those things. So I think that was another piece that nicely complemented the visionary to the operational side of things. Manuel Martinez: And as far as the structure goes, like you said, note taking, documentation, I’ll be honest, I’m one of those people, I don’t enjoy it, but I do know the value of it. So I will document the work I have, not because I enjoy it, but because I know if it’s documented, I can then hand it off. Chelsey Bonilla: Yes. Whereas you seem to enjoy the documentation part of it, and is that something, did you learn that going through school, is that something you learned working early as a 15-year-old in business? Where did that understanding of how important it is, and then it sounds like eventually you developed a love for it? Chelsey Bonilla: I would say it’s my learning style, even thinking back to high school, I was always the person with the big notebooks, and I would take a lot of notes, and the way that I retain best is if I’m physically writing something, so I think that is the origin of my love of note taking, and then looking through my, throughout my career, thinking of what that looks like later on, I’ve always gone into roles with the goal of, if the worst case happened to me, or if it’s time for me to move on, I like to build that documentation, so it’s easy to hand off the history. I never wanted to feel like all of the knowledge of a role lived within my head. It’s intended for the business, intended for the organization, so that was always a goal of mine, was to keep records that allowed someone to step into my role, or in my absence, take over if needed. Manuel Martinez: So then, you’re starting to learn all these acronyms, you’re starting to understand, you know, Agile and Scrum, and starting to deal with the developers. In that role, did these, you know, coming from the outside, right? Sometimes I know people who are technical, sometimes they have a bit of that, like, well, you don’t even know IT, like, you don’t know what you’re talking about. Chelsey Bonilla: Yeah. So how did you handle that? Because I’m sure, when you first came in, they’re like, well, who is this person? She has no background, how is she leading us? Chelsey Bonilla: Yeah, absolutely, that’s a great question, and as a female in the organization, I was the only female in the organization, working with individuals, not only in the United States, but overseas as well, so the development team that I was managing was based in Serbia, and the ability to be vulnerable and honest has been the secret weapon that I’ve seen, is being able to say, I don’t know what this means, I don’t understand, can you explain it to me? And when you have that vulnerability, instead of trying to fake your way through something, I’ve seen that works really well, so in that instance, I remember I was talking to our lead developer about APIs, and I did not understand what APIs were, and he drew it out for me, and I’m very much a visual learner, he drew it out for me, and there was this moment where I was like, oh my gosh, I understand, and just the drawing of it out, seeing the API keys, understanding the passwords, and then putting it all together, it was like this aha moment, where I felt like I was vulnerable enough to say, I don’t get it, you need to explain it to me a different way, and that allowed them to welcome me into the team, to say, she doesn’t have the skills that we have, but she has other skills to offer. Manuel Martinez: That’s a good point, right? They’re probably teaching you so that you understand it, like, are you gonna be the one developing, and are you building all these APIs? No, you’re not. But for the leadership and being able to make decisions, you have to understand what the problems are, or why we’re going in this direction. So I think that’s important for anybody, whether you’re that technical person, or you’re not a technical person, is saying, hey, I don’t know, help me understand, and I need to know for X, Y, and Z. I’m not trying to take your job, or I’m not trying to be that go-to person, or if you are gonna be that go-to person, it’s like, I wanna be the go-to person to be able to kind of help guide you in the right direction. I don’t know the answer, but I can find it because I know who to ask. Chelsey Bonilla: And I feel like what’s so common in IT is typically technical individuals rise through the ranks, and then the business is typically guiding decision-making. So that ability to understand technology, but articulate it in a way that individuals in the business can understand, or non-technical individuals can understand, is a true skill and an art. So I think from my perspective, coming from a business background into IT, and building those relationships, to be honest, and say, I don’t understand, has helped me grow in my IT career. Manuel Martinez: And were they asking you similar questions that you were asking them? Like, you’re asking them technical information. Did that vulnerability also allow them to feel comfortable to ask you? Be like, well, why are we doing this from a business standpoint, right? Chelsey Bonilla: Yes. Manuel Martinez: Because a lot of times, you’re technical like, oh, we’re doing it this way because this is how it works, or this is the cool way to do it. Why are you making me do it that way? Chelsey Bonilla: Absolutely, and I think the shifting gears, all too often in IT, we get set on a path, and then we have to pivot very quickly, and especially from a developer mindset. It’s like, wait, what do you mean? You can’t change what I’m doing. I have a plan, and we’re gonna execute on my plan. So being able to articulate to them, this is why, from a business perspective, this is what’s gonna generate the most amount of money, this is what’s gonna make the most sense, this is what’s gonna be most attractive to investors. I think those conversations were eye-opening for them to say, oh, okay, I’m frustrated, but I understand why we’re pivoting or why we’re changing. So it built this level of trust. Manuel Martinez: So in this role, obviously, because you kind of stayed in the IT realm, what is it that said, hey, I like this, and I wanna keep growing within this role? Because you mentioned that the MBA, all these other different industries, there’s all these different experiences, what is it that made you say, hey, you know what? I’m gonna continue this path, even though I don’t know, and I didn’t have that experience, I’m learning, but you stayed with it instead of saying, hey, you know what, I tried it, I didn’t like it, let me go do finance instead, or something else. Chelsey Bonilla: I would definitely say I fell in love with IT. I love the continuous learning nature. I love the community of introverts, as goofy as that sounds. I am able to be an extrovert, but I truly am an introvert, so finding people who are like, I’m good being social, but I also just wanna go home and binge watch TV and read books. I was like, oh, I finally found my people, like this makes sense. So I think being able to continuously learn the evolution of technology and finding a sense of community with people who were similar to me is really what drew me into IT. And then growing in that career, I was three years with that organization. From a startup perspective, I then had my daughter at that point, and the volatility of working in a startup is what shifted me into more of a medium-sized business. So then I transitioned out of the startup into an IT staffing firm, and that was really interesting because I started to learn different roles within IT. So there was a lot of exposure to like, what does a network engineer actually do? What are all these different development languages? What’s a service desk versus an IT tech? So that was a great exposure, and during that time within the IT staffing firm, within the first, I think, month of me starting there, one of the roles that we were recruiting for was an IT project manager for Clark County Elections. And it was a short-term role. It’s very hard to find a project manager who’s willing to work short-term. And I was like, “I’m organized. “Put me in, coach. “I can do it, no big deal.” And so I went onsite to Clark County Elections, and I was like, “Hey, I’m here to be a project manager.” And I just absolutely fell in love with public sector. And I think that was the piece of my career that then translated to my role now that was so essential is I was never, I was actually a practitioner. I was working side-by-side elbow-by-elbow by the systems engineers and the techs and supporting a team of PC techs and senior business systems analysts. So just working within this environment and again, being accepted into the environment and just the propensity to learn, it was such a great experience. And then being able to give back to my home state and my community and my county by working within Elections was such a rewarding experience. Manuel Martinez: Man, there’s a number of things that I kinda wanna dig into here, but I guess the one that I’ll start with is having only been in the industry for three years, right? With this startup and feeling, especially when you first came in like, “Oh my gosh, I don’t know anything.” What gave you that confidence to say, “I can do it.” Like I understand that when you kind of looked at what a project manager does, and again, I’m not trying to simplify this by any means. Chelsey Bonilla: Yeah, yeah. Manuel Martinez: I couldn’t do it. Chelsey Bonilla: Yeah. Manuel Martinez: But you’re like, “Hey, I’m organized, I can do this.” But something also gave you, again, that confidence or at least the ability to think, “I can do this, I’ve seen what it is I can go through.” Even though I’ve never technically been a project manager, maybe you’ve managed smaller projects to kinda go through and say, “We don’t need to hire somebody, I can do it.” Chelsey Bonilla: That’s a great question. Similar to IT, a lot of people fall into IT unintentionally. I’ve heard from a lot of project managers, you fall into project management as well. So it was kind of that, “I’m organized, I’m good at spreadsheets, I’m good at managing people.” Okay, I check most of the boxes, so why don’t I just try this? And I think there was enough faith in me to say, “I think she can do it, let’s let her go try.” So I think there was a little bit of, “I think I can do it, hopefully I can do it,” and kind of thrown into the situation. But also having the confidence from my background, from the people management, throughout my MBA, I learned that I am very organized, which is one of those strengths that I have, which is essential for a project manager. So I think that was a big driving force as well, is knowing that I’m organized, I like spreadsheets, I like managing people, and that kind of naturally led to, “Okay, I think I can do this, give me a chance, I wanna try it.” Manuel Martinez: And is that something that you feel, you know that, “Okay, I have enough of the skills, I can figure it out.” The reason I ask is, that’s what you’re explaining is me. I’ve gone through a lot of these roles, and I’m like, “Okay, I think I have these skillsets, I’m pretty sure I can handle this.” But I know that if I’m put into that situation, even if I don’t have the skills, well, I’ll figure it out. There’s something in me that says, “Okay, even if I’m not confident from day one, that I can do the job, I know that if you give me the runway, oh, I definitely can do it, and I will exceed whatever the standards are.” Is that kind of what you’re seeing? Because it sounds like as you progress through your career, you’re put in situations that you didn’t know, you slowly start to learn and figure out and say, “Okay, I can do this,” or, “Hey, I can apply this,” and it’s kinda snowballs, is that accurate? Chelsey Bonilla: 100%, and I think it’s not having that fear and being okay to say, “Yeah, I think I check enough of the boxes that I just wanna try it,” and like you said, if I’m in a situation where I don’t know how to figure something out, I’m gonna figure out a way, whether it’s self-learning, asking questions, being vulnerable, googling it, whatever it will be, I’m gonna figure out a way to accomplish the goal. So I think, especially going, again, back to the MBA, you’re putting a lot of scenarios where you have no idea how to solve a problem. So it definitely honed my problem-solving skills and also increased that confidence to say, “Maybe I don’t know exactly how to do this, “but I’m gonna figure it out, “and if I struggle along the way, I’m gonna ask for help.” Manuel Martinez: So now you’re in here, you’re a temporary project manager, you’re working for the county for the elections, you start to develop a a love for public sector and kinda helping, and you mentioned community, Vegas and Nevada, just based on your LinkedIn posts, and just talking to you like I can see that, because as someone who’s also born and raised, I wanted to move away a couple times, because you’re like, “Oh, I want these other opportunities. “Something keeps me here,” and then kinda looking back, I’m like, there’s a reason, right? And the IT community is, as big as the city has grown, it’s still a small community. Chelsey Bonilla: Absolutely. Manuel Martinez: So now you’ve developed this love, and you’re learning project management, what do you decide at this point that you’re gonna do? Because again, it’s temporary, it’s not like, “Oh, hey, you’re here, do you go back to your staffing? “Do you decide, hey, you know what, “I wanna get involved more in public sector.” What transpired? Chelsey Bonilla: So, I had a split role during election cycles. I was 100% onsite at Clark County Elections, but I was still an account manager, which was my first time being that role in the IT staffing firm. So I was kind of wearing two hats simultaneously, which was great because it was giving me experience and exposure to account management, which is very much rooted in business relationships and being a support system and being that connective tissue to kind of bring the resources of the business to the client. So I was doing these split roles. Again, my daughter kind of driving some of the decisions that I’m making in life. At this point, she’s about two, and I’m working onsite in an office. And in that startup role, I was 100% remote, and I was remote for three years, which kind of even pre-COVID, I learned to love working remotely for a variety of reasons. And I’m one of those people that will work harder and longer when I’m working from home, because I don’t have to commute. So there’s another 20 minutes that I’m gonna dedicate to working, and I’m definitely one of those people. So there was a pivotal moment where I just made the decision as a mom and as a working mom that I wanted a role that checked a lot of boxes, but was remote. That was really important to me is to find something that was remote. And as a working parent, having that flexibility to drop my daughter off, pick her up if she’s sick, it’s okay to go get her, different things like that. That was really important to me. So I had this little itch in the back of my head that I loved what I was doing, but I needed a role that was a little more flexible to me as a working mom. And so I just kind of serendipitously met someone from consulting while I was onsite at Clark County Elections from an organization called Gartner. And I’m one of those business nerds that when I hear a new business and I’ve never heard of it, I go cyber stalk the business. And I Google them and I look at their value statements and their mission statements and who they are. And I read Glassdoor and the testimonials. I was at this stage in my life where I wanted to find an organization that checked all of the boxes from the values, from the logistics of working from home, from something that’s intrinsically motivating. And so I just did this deep dive into Gartner and I became obsessed, being completely honest. I was like, I want to work there. That is such an amazing organization. I attended webinars of people who worked there. And just, it was a, I distinctly remember it was a panel of women and they had hired a woman who was seven months pregnant. And I was blown away because there’s this stigma that if you’re pregnant, you’re going to take time off. So how could you be hired? And that’s not true for multiple organizations, but just this thing that kind of lived in my mind. I was very worried about if I were to have another child, what’s that going to look like? Is that okay? Can I take time off? So I just became infatuated with Gartner. And I was like, I love this organization. They stand for everything that I stand for. They have high ethical standards, blah, blah, blah, blah, so anyways, fast forward. I fell in love with this organization. And then by, again, fate, I feel like I’m, at the time was the secretary of an organization called SIM, Society of Information Management, which back to your point about the IT community, is a huge piece of the IT community that I’ve built over the last couple of years. And Gartner just happened to be sponsoring this meeting that SIM was having. And I was like, okay, the stars are aligned. Something’s telling me I need to be prepared to meet every person from Gartner there and introduce myself and stand up tall and say, tell me a little bit more about your role. What do you think of the organization? So I openly and honestly cyber stalked everybody who was coming to the meeting, looked at their LinkedIn, did all the learning that I could about them, showed up early to the event, and was just prepared to kind of shoot my shot and see if there was a path in. And me as someone who had never worked for a big organization, had a little bit of a different path, going from operations to startup, to project management, kind of blended. How am I going to get my foot into the door of this $7 billion global organization that is everywhere in IT? And I just didn’t know how to crack that code. It was one of those things I had no idea how to do it. There was no roles available. So fast forward to that SIM event. I introduce myself to everybody. I shake hands, I hand out my business card, I email them that night. Anyone who will talk to me, I connect with them on LinkedIn very strategically. And I just make it known without saying, hi, I want a job, saying I’m very interested in Gartner. And I’m really interested in that organization. So that happened in February, a role popped up two months later. I’m watching the Gartner website, role pops up, I apply for it. I get rejected within three days. And I’m like, is this a sign? Do I need to walk away? Is Gartner not for me? And I get a call a couple of days later from one of the individuals that I had met at that SIM meeting saying, I may have a role for you. It’s not the one you saw on the website. It’s something that’s not open yet. Send me your most recent resume. And so I felt like that was my sign to say, okay, here’s my chance to shine. This is my path in. And that then led to the hiring process at Gartner and the role that I have now. Manuel Martinez: Before we get into more about that role, there’s a couple of things that I’m probably gonna ask multiple questions around here. Chelsey Bonilla: Absolutely. Manuel Martinez: So the first one is, and you touched on it, you became involved in SIM. And at some point, and I wanted to kind of bring that up so it works out perfectly, is how did you get involved with this organization and what made you kind of want to start kind of building that network? Because it is something that’s important. And again, as a recent member of SIM, I just joined this year, that wasn’t something that was, like I didn’t look at and at the time, see the value in it for me. Now also at the time, SIM used to be more for kind of like director level and above, right? So there was that kind of like, hey, it’s closed off. And I was like, I have, you know, and I didn’t know of many other organizations that has since changed. So now it’s more kind of like that professional like engineer, architect and above. But how did you get involved and kind of why? Chelsey Bonilla: So welcome to SIM. Manuel Martinez: Thank you. (both laughing) Chelsey Bonilla: So SIM, I was introduced by the CEO of the staffing company that I was working for. She brought me to a SIM meeting. The first SIM meeting I went to, I met Cynthia Hara, who I know is one of the early on guests on your show. And I remember going to the meeting, there wasn’t a whole lot of attendees then because this was probably about three years ago. And I just remember seeing, you know, people walking up to each other, shaking each other’s hands, giving hugs, asking, hey, how are you doing? Where are you working now? And I remember just watching as kind of a bystander who didn’t know a lot of people in the room, watching the engagements and thinking, oh, this is like a gathering of people who know each other. And it just happens to be around IT and networking and things like that. So I continued to go these meetings over and over again, and I was asked to be the secretary, which was awesome, because it kind of fast forwarded my exposure to SIM. So that was great because I got to learn a little bit more about the organization, where have they come from, what’s the objective, where are they going to? And I think what really cemented it for me was being a part of the golf tournament, the first golf tournament for SIM Las Vegas. I’ve always been someone who likes to help and give back. And again, there was a golf tournament committee. Anybody want to be part of it? Yeah, put me in, coach. I’d love to do it. I’m organized. I can corral people and herd cats. And so I started with the golf tournament, and I remember at the conclusion of the first golf tournament, and I was kind of the person who helped organize meeting notes, registration, different things like that. And I remember seeing 100 plus people in this room, all IT, and just it was the sense of community that came together, and the room just had this electricity about it. And I think that was a moment where I was like, okay, this is something. Manuel Martinez: These are my people. Chelsey Bonilla: These are my people. This is a community. I can walk up to people and hug them and shake their hands and say hi. So I think that was my first exposure to networking within the IT community. And I am incredibly grateful and still a member of SIM, and I absolutely love what SIM does for the community. And the third golf tournament, I’ve been involved in all three, including the one that’s coming up in a couple weeks. So I just absolutely love SIM. But I think that piece of building connections within the IT community, like you said, the IT community in Vegas is very small. And being able to have that place where you know you’re going to meet with your people on a regular basis was incredibly helpful for me as I took that step back and said, what do I want next from my career perspective? Manuel Martinez: And it’s amazing that, like you said, it is that community. It’s the people who know each other. Similar to you being born and raised here, and I’m sure that this might be a similar experience, I would run into people that I knew all over town. And it wasn’t until later on where I started to have more of those same types of interactions, but within IT. Chelsey Bonilla: Yes. Manuel Martinez: Whereas before it was just people I went to school with, people that my dad knew, people that, you know, all over the place. So my wife jokes a lot of the time. She says, when we first started dating, she goes, can we go somewhere and you not know someone? (laughing) And I was like, Chelsey Bonilla: I don’t know about that one. Manuel Martinez: Probably not. And I told her, like, Vegas is small. And she’s like, it’s a big city. I was like, it’s not as big as you think. Chelsey Bonilla: Right, yeah. Manuel Martinez: But IT felt different to me. Like, sure, within the casino, like I said, I knew people that I worked at this casino. I worked in this role, but they weren’t necessarily IT. Chelsey Bonilla: Yeah. Manuel Martinez: And in the last few years, I do feel that. I feel like I go now and I probably run in now more to IT people than I do people outside. Chelsey Bonilla: Yeah, absolutely. Manuel Martinez: So you’re building this community, and do you think that that came, was this around the same time where you got involved with public sector? Like, is that where, you know, hey, not only do I want to meet people, I’m organized, I can help and provide value, but I get to build this community and it’s within where I live. Chelsey Bonilla: And I think a big part of SIM, at least when I joined, were public sector employees. So I got to meet different public sector employees and learn about different agencies. And especially as someone born and raised here, you don’t grow up here and think like, how is my government infrastructure supported? Like, those aren’t the questions you ask yourself. So just seeing like, you know, behind the scenes and how powerful and impactful the work that people in public sector, what that means, I think that was just so rewarding for me. And getting that exposure within SIM, even outside of Clark County, but other agencies, building those relationships and understanding the different roles and why they’re important and what they do, that was such a great experience for me as well. Kind of expanding my network and seeing how collaborative and supportive the IT community is in Las Vegas. I think that’s the other piece is, everybody’s rooting for each other. So I mean, you post on LinkedIn and we comment on each other’s posts and you see somebody out and you say, hey, congratulations on that new role. And it’s just very much a community where we know what’s going on in each other’s lives, which I love. I don’t have personal social media, I only have LinkedIn, but I love that that’s my way to share what’s going on in the world with my community. And I love that we all lift each other up and we all support each other. Manuel Martinez: I think a lot of that, kind of as you’re saying this, I see now where I’ve seen a lot of big companies or I’ve seen a lot of other vendors and stuff like that try to bring people from the outside. And I’m not saying that there are some that are successful and are able to do it because they take the approach of, hey, I really want to understand and I want to be a part of this. But most of the time, and I found out that this is very unique to Vegas is that it’s very, it’s closed off. Like, hey, we’ll support each other, we’ll help you out. But if somebody comes from the outside and there’s this like, hmm, what are you doing here? Like, why are you really here? And maybe they are trying to be part of the community, but there is that guarded, like, I gotta feel you out for a little bit. Chelsey Bonilla: Within the community, we all know each other so well. So it’s definitely that like, hey, who are you? I’m gonna vet you out a little bit. I don’t know you that well. And I think the unique part about, I know we’re gonna get to my current role, but my current role is supporting public sector in Nevada. So that I feel like is another way that I get to give back to my community is the territory that I manage and the territory I support is only Nevada public sector, which is perfect for me. So again, one of those stars aligning type things where it was like, what do you mean? I get to support the state, the city and the county that I love more than any other place in the world. Like, hello, Dream Job. Manuel Martinez: So as you’re talking about getting to your dream job, so one of the things that you talked about, and this is kind of the other section I wanted to cover, was you talked about not only with Gartner, but with the people that were involved. And you said, you know, like openly stalking. And I think it’s more doing your due diligence is the way I see it. Because a lot of times, and I’ve seen this and I’ve heard these stories where like, oh, I’d like to work at Gartner and they’ll apply and they’re like, oh, I can’t get in and that’s it. Or, hey, I met somebody and I asked them if they had a role, but nothing came of it. Chelsey Bonilla: Right, right. Manuel Martinez: It sounds like you did a lot of the work ahead of time. Like it’s preparation. Maybe it’s part of being organized. Again, I feel like you and I kind of lived a similar career path. Because at some point I was like, I want to work at VMware. And I did the same thing. I researched a lot about them, who worked there. I would see people, you know, at the time, Twitter was a little bit bigger within IT. Who were these people? I was making connections and really started to get to know these people. And I was like, this is where I want to work. Chelsey Bonilla: Yeah. Manuel Martinez: You did the same thing, you keep going through and you’re like, hey, I’m going to shoot my shot. But it wasn’t like, well, I’ve never been here and I’m just going to throw stuff. It’s like, okay, hey, I practiced a little bit. I did a little bit of research. And now I’m going to shoot my shot. But like you said, I’m sure that the interactions that you had with these Gartner people was different than if I hadn’t researched it. And I come in like, hey, I’m Manny, tell me about Gartner. Whereas you probably went and was like, hey, tell me about Gartner. And you probably, I don’t know if you did, but maybe said a little something that you had learned. Hey, I recently saw this, or I heard something. So that it shows that you’re like, have a little bit more preparation and you’re not just like, oh, I want to talk to you because you’re a Gartner and that’s it. Chelsey Bonilla: I think part of the role that I have as an account executive, part of that role is doing your research and knowing the team that you’re working with, the environment, the agency, the state, the laws, what’s important. So kind of going back to preparation for interviewing with Gartner, I was unknowingly kind of modeling some of the behaviors that I need to model within my role. So doing that homework, doing the research, and that really stemmed from my experience in staffing because you could be one of a hundred candidates interviewing for a role. So how are you going to prepare and stand out and be different? And that’s the mantra that I lived by with the candidates that I supported as they were going into different roles. And then when it was my turn to apply for different roles, that was my time to say, okay, well now, you talk about this all the time, you need to do it yourself. So I deep dived as far as I could into who is Gartner, what do they do, who do they support, how do they support those people, what are the values, what’s the tenure of the team and the cyber stalking, I have no shame in my cyber stalking. And when I speak to my mentees or students at Tech Impact, I say, don’t shy away from cyber stalking because that could give you that competitive advantage. Instead of walking up to someone with your name, you’re walking up to somebody with, I have done my research and let me tell you about all the research that I’ve done. Manuel Martinez: Is that just, again, you being prepared, being that note taker that you wanna understand because it sounds like that constant thirst for knowledge, that’s where it came out. And you almost didn’t really think about it, like, oh, this is gonna lead me to a job. It’s just like, I wanna know everything I can. And obviously it helped you to make a good impression because like you said, you applied, you get rejected, but then a couple of days later, this person reached out to you. So you must have made a good enough impression at that interaction when you met them in person to say, hey, there’s something that I think you would be good for. Chelsey Bonilla: Kind of going into my present role, it was how much preparation could I do? I knew there was this meeting coming up. I knew it was a SIM meeting sponsored by Gartner. I knew that there were going to be people who worked for Gartner. So how can I put my best foot forward? How much research can I do in advance? Can I follow them on LinkedIn first and then connect with them after the fact? Like, how strategic do I really wanna be about how I’m going to interact with somebody? And that was my chance to kind of show what that looked like, make that impression, and then a couple months later, have that individual reach out to me and he is now my current boss. So he knows I cyber stalked him. It all worked out like it was supposed to. (both laughing) Manuel Martinez: So now you get into this role, you make this good impression. Obviously you did well enough to go through the interview. Sounds like everything is aligning for you. So what is it that you do in this role and why do you think that it’s the perfect fit for you? Chelsey Bonilla: Before I go into that piece of the question, I’d love to talk a little bit about the interview process. Manuel Martinez: Oh yeah, definitely. Chelsey Bonilla: Because I recently did a talk at Tech Impact where I talked a little bit about kind of networking your way into your dream role. So I felt like at this point, I had the chance. My now boss reached out to me and said, “Hey, if you wanna apply for this role, I think we’ve got something for you.” Nevada Public Sector is the territory, account executive, similar to what I was doing at the previous organization. So it was like all the stars aligned, but I didn’t realize the path into Gartner. So I had seven interviews from start to finish. And that was by far the most interviews, the most rigorous interview process I had ever been through. And I tell that because people listening to your podcast or what I’ve heard from your vision is when you get into those situations and you find that role or you think, what’s the path to get there? I was incredibly intimidated by the seven interview process, but it was also that moment to say, okay, I got myself this far, now I need to get myself over the line. So going through that interview process, I got to interact with a lot of different people within Gartner, including leadership that I now work for currently. And it was again that moment where I realized I was doing exactly what I was supposed to be doing because everybody that I interacted with, I was like, these people are awesome. Like I really wanna work with these people. So it was that motivating, the harder the interviews got, the more motivating it got because I was never, there was never a red flag or a yellow flag or an orange flag where I was like, maybe I don’t wanna do this. It was more reaffirming that I was doing the right things and I was moving in the right direction for a role that I really wanted. Manuel Martinez: And when you went through this interview process, did they tell you, hey, you’re gonna interview with seven different people or was it more, hey, you’re gonna go through multiple interviews? Chelsey Bonilla: It was more, you have a recruiter the entirety of the way and they are your guide throughout the process. So that’s great because you have somebody to kind of coach you along the way. They’re not giving you the answers by any means, but they’re walking you through the logistics of what you’re gonna go through. And it’s at least what I’ve heard, similar to large organizations, you see these long interview processes, but people typically stay with these organizations for really long tenure as well. So I always had that in the back of my mind, like, okay, this is a long process. It’s gonna be hard, it’s gonna be challenging, but there’s a reason. This is, there’s a reason that I need to get through these like levels of accomplishment to get to where I wanna go. So going through that process, I interviewed with an HR recruiter, then I interviewed with my manager, then my manager’s manager, then the next level up, then I did a panel interview with the whole team. So it was like those different phased approaches to kind of like video game, you know, unlock the next level. And then when I got to the end, they were the ones who made the decision and I got the call pretty quickly and I was just elated. So it was worth, the juice was worth the squeeze. Manuel Martinez: And I’m glad you brought up, you know, working with the recruiter, because a lot of times if you haven’t worked with one or you’re not sure, or you think like, oh, well they work for the company, they’re not really advocating for me. Earlier on my career, like I was very standoffish with recruiters until I learned, and don’t I remember, actually I do remember, there’s a guy and he’s still here, but now he moved into, God, it’s Branson. His name is Branson. He was a recruiter for a tech company. And that was the first time when I started interacting with him, because he could tell I was very, kind of little standoffish. I’ll give you information, but I’m not gonna really tell you everything. And he had kind of a frank conversation with me and said, hey, listen, the more, I’m asking you these questions for a reason. He goes, the more that you could give me, the more I can advocate for you. And I was like, well, can you really, you know, blah, blah, you know, just, I I didn’t have that type of information, anybody I could ask. So he was the one that kind of really opened my eyes and said, oh, wait a minute, they do advocate for me, while also advocating for the business, right? They’re trying to fill a role. They wanna find the best person. And if they think that I’m that person, or maybe not for this role, but the more information I can give them, they’ll be like, oh, okay, wait a minute. Manny and Chelsea, like, I know you’re trying to go for this role, but you’ve told me kind of what you do. Let me keep you on the back burner so that when something does come up, now you’re that person. And in a large organization, they’re kind of doing the same. They are vetting you, but they’re there to help you and ask questions. They won’t give you the answers, but they will tell you like, hey, this is, like for me, it was like, hey, you’re gonna go through a technical, you know, two or three technical interviews. Be prepared for those types of things. Hey, be honest. You know, they didn’t tell you that, but it was just kind of like, hey, be honest, you know, answer what you can, but just kind of explain to them. And, you know, they do prepare you. Is that something that you had researched ahead of time and knew that that was a process? Or was that recruiter just that open with you where you’re like, oh, okay, well, I feel comfortable. I’m just gonna kind of let them guide me along. Chelsey Bonilla: Yeah, I think in my IT staffing role, that was my exposure to recruiters. So as an account manager in that role, I was supporting a team of recruiters that would provide candidates that I would then bring to clients. So that was my first like, dip my toe into what does a recruiter do? So I had a good context on like, what is a recruiter’s role? But going into Gartner, it’s very different because they’re really making sure that you’re a fit. And I love the term advocate. They’re an advocate not only for you, but for the organization, because what good does it do if you put a square peg in a round hole and you don’t work out? It doesn’t help anybody. It leaves a bad impression on you, the candidate. The organization doesn’t have that role filled. So really leaning on that recruiter as an advocate and as a tour guide to kind of say like, okay, we completed step one. What’s step two, three, four, five, and six, and seven gonna look like together? And then from the research perspective, Gartner is very open, honest, and transparent about the process and what that looks like. So they even have like podcasts from current employees on what the interview process looked like. So I remember listening to those podcasts and hearing more about people. And then I would look on YouTube and watch people talk about the interview process. And there’s a variety of roles within Gartner, but the process is very similar. You’re typically going through a six to seven stage process. It typically takes multiple months to get through the process. So I had an idea, but it was, at that point, it was more, how am I going to succeed in this process? And the recruiter was definitely the advocate along the way. Manuel Martinez: So now you get the great news and you, I’m not gonna assume, I know you accepted the role because you’re there now. So what was it like to kind of go through and again, you have IT experience, you have that account management experience, but now this is different, right? And now it’s almost seems like a combination of all the skills that you’ve been kind of molding, but now you’ve got to put them together. And as much as you’re like, oh, I have this skill, that skill, this skill, that skill, putting them together, that’s got to be a little bit of a challenge, especially coming in to a large organization. So how did you deal with that? And how did kind of the business support you at the same time? Chelsey Bonilla: So I think first off, it was really hard to leave my previous roles. So I think that was part of it was, I knew that I wanted this role more than anything, but the saying goodbyes was challenging to say, I’m doing this because it’s better for me and for my family. That was a hard piece of it too. But then going into, I’d never worked for a big organization. I always knew every single person who worked in the company that I’d worked with. I was typically the right hand of the CEO for the organizations I’d worked for. And now I’m going into this, 8,000 plus workforce global organization. How am I going to stand out? Like how am I going to do the replicates, the things I’ve done? So I think that was like the scariest part for me is going into this really, really big organization with incredibly intelligent people. I mean, I can’t say enough good things about the caliber of people that I trained with and worked with, but Gartner does a really, really good job of training people. So we went through an amazing training process. And then one thing I love about the organization that as an outsider looking in, what really made me interested was the caliber of people, but the open and honestness to help is something that was important to me. And I still feel that, you know, a year plus into my role, I’ve never had a problem that I can’t ping someone on Teams as a remote workforce or call someone or text someone and say, hey, I don’t know how to do this. Can you help me? So throughout that training period, I think I learned that and that has been ingrained in me that again, I can ask for help. So it was a great process really to get acclimated to this big organization and realize, you know, corporate America isn’t as scary as you think it is. There really is inclusive, supportive and helpful culture within the team that I work with. Manuel Martinez: You’ve kind of gone through the ranks. You’ve picked up all these skills. You’ve done, you know, work with SIM. You touched on it before where you’re also kind of trying to find other ways to give back. You’ve talked about, you know, you speak at Tech Impact. So it sounds like you continue to kind of give back and help out. And I know that’s part of the reason that you decided to come on and share your story is again, you’re kind of in a small way giving back and, you know, trying to help others as they’re either starting or maybe they’ve been there for 10, 15 years and they’re like, I want more, but I don’t know how. So hopefully this is that catalyst to kind of move on. What other areas that maybe we haven’t touched on that you think like, oh, this is important or hey, we kind of glazed over this area of my career. Chelsey Bonilla: I think we did a good job to you, credit to you, you know, talking about the full gamut of my career and where I am now. But what I think, especially when I think of like your vision, which you kindly shared with me a year ago of providing exposure to people to understand, you know, there’s not a linear path into IT that you can take twists and turns and you might fall into it and you might not know what your end destination is. But I think what I would love to share is that as a non-traditional IT role an account executive supporting Nevada Public Sector for Gartner, I’m not necessarily a practitioner even though the amazing teams that I get to work with embraced me as if I am one and I’m, you know, members of the team, but just feeling comfortable enough to let the stars align and let fate guide you to what the right role is for you because I’m one of those people who like, okay, I need to make a plan and I’m gonna make a plan and I’m gonna stick to my plan. And then sometimes that can limit that growth. So just being comfortable to say, I’m gonna see where my IT career takes me or I’m gonna see where my career takes me and see where it grows and what it evolves into. And if I think you sit back and let that happen, a lot of times, as long as you’re organized and prepared and a go-getter, you’ll end up in a really amazing place. So I think that’s what I would love to share with the audience is, you know, let the world take you where it’s gonna take you and there could be an amazing outcome at the end of it. Manuel Martinez: Let it take you where it’s gonna take you, but I think you also very well demonstrated, talked about, you also have to be prepared for when that opportunity comes, right? Chelsey Bonilla: Yes. Manuel Martinez: Doing your homework and, you know, doing research on the company, on people, on, you know, organizations and just understanding like what’s available and I think the other thing that, you know, I kind of try to put together is you’re picking up skills in different areas. And like you said, like, it gave you the confidence to say, hey, I can do that because I’m organized, like, I’m sure in the job description, it doesn’t say someone who takes meticulous notes and is very organized, right? Like, that’s not what it is, but understanding how do you read a job description and really know what are they asking? Hey, being able to communicate with people and establish relationships. You learn that, you know, one in that small organization, but when you came in and started leading developers, like being vulnerable, asking questions, you’re like, oh, okay, well, I’m managing a project, that means I’m gonna have to talk to people. Oh, I can do that, I can, will I know exactly how elections work? No, but I can ask questions, I can figure it out and kind of putting all these different skillsets to use because I think that’s the thing that is both fantastic and also probably intimidating about IT is, Chelsey Bonilla: Yeah. Manuel Martinez: You can take any skillset, you can come from any other industry and come into IT. But I think at the same time, there’s so much that people are like, oh my gosh, like, I don’t know if I can do this because there’s, you know, there’s so many different avenues or I don’t know what, you know, a network engineer does or a lead developer. Okay, well, especially now, there’s all kinds of resources to kind of research. So how would you kind of summarize that or in your own words say, hey, this is how I did it and this is why it worked for me as kind of like a non-traditional IT path? Chelsey Bonilla: I think going back to the ability to be vulnerable and say, I don’t know, and especially in IT, even if you think you know, the technology’s probably changing right before your eyes, whether you know it or not. So I think just, you know, putting the ego aside, being vulnerable enough to say, I don’t know the answer but let’s figure it out together or come to your boss or your leader and say, I don’t know, or I always tell people, be okay to say, I don’t know in an interview. When you go into an interview process, if you don’t k
The Career Built on Course Corrections with Ruben Sarino | Ep053
Episode Information Show Notes What happens when you stop planning your career and start asking better questions? Ruben Sarino didn’t set out to co-found an AI security company. The path from military kid bouncing between six countries to RiskHorizon AI co-founder included selling car parts, packaging California honey, working Apple retail, cold calling at CrowdStrike, and several stops in between. None of it was planned. All of it mattered. What You’ll Learn Growing up in Japan showed Ruben what technology could do when it actually worked. Tapping cards to ride trains and buy things felt seamless. Visiting developing countries showed him the same problems without the same solutions. That contrast planted a seed: technology should solve real problems for real people. But Ruben didn’t study computer science. He studied business. His first exposure to entrepreneurship came through a car parts manufacturer where he learned the difference between pushing products and solving problems. Then came a honey business he fell into by chance, where terrible packaging met great product. Apple retail taught him how great companies operate. CrowdStrike as an SDR gave him front-row seats to hypergrowth and mentors who showed him what came next. Each stop built skills that transferred to the next one. Key Insights On Getting Started: “If you know too much, you will never start.” Ruben talks about the danger of over-researching and why ignorance sometimes helps you take the first step. On Career Direction: His annual self-check-in doesn’t ask “what do I want to do?” It asks “how do I want to feel next year?” From there, he works backward to figure out what needs to change. On Problem-Solving: Whether it’s car parts, cybersecurity, or AI, Ruben looks for the underlying problem before building solutions. Not everything needs AI. Some things just need better execution. On Mentorship: The CrowdStrike account executives who took time to show him what happened after the handoff shaped his trajectory. He didn’t formally ask them to be mentors – he asked good questions and stayed curious. On Risk: Being comfortable with change helps, but it’s not required. What matters is believing you can course correct if things don’t work out the way you planned. About Ruben Sarino Ruben Sarino is co-founder of RiskHorizon AI. His career spans car parts manufacturing, honey business, Apple retail, cybersecurity sales at CrowdStrike, workforce intelligence startups, and healthcare technology. He’s comfortable with change, believes in transferable skills, and thinks most people overthink their next move. Connect with Ruben on LinkedIn: Subscribe to Career Downloads New episodes drop every week featuring tech leaders, CIOs, and professionals sharing their career journeys and the lessons they learned along the way. Website: https://careerdownloads.comLinkedIn: https://www.linkedin.com/company/career-downloadsYouTube: https://www.youtube.com/@careerdownloadsTikTok: https://www.tiktok.com/@careerdownloadsInstagram: https://www.instagram.com/careerdownloadsFaceBook: https://www.facebook.com/people/Career-Downloads/61561144531249 TranscriptionManuel Martinez: Welcome everyone, my name is Manuel Martinez, and this is another episode of Career Downloads, where each episode I basically hit the refresh button, bring on a different guest, to learn more about their background and their experiences, to really help uncover any actionable advice that you can use as you’re managing your own career. So I’m excited for today’s episode. I have with me Ruben Sarino, and him and I met at a networking event. We got to talking, just learning about kind of what he’s doing. He was asking me what I was doing. You know, we connected on LinkedIn, got to know each other, our backgrounds. And I think he has a lot to offer, and there should be a lot of good stories, a lot of good information that people can use, you know, whether you’re just starting out or you’ve been in the field for a while, you know, and are looking to make a change, either to a different area or, you know, maybe even promotion-wise. So with that, I’ll introduce Ruben. Ruben Sarino: Hey, how are you? Manuel Martinez: Good, appreciate you coming on and being willing to share your experiences and your story. Ruben Sarino: Thanks for having me. Manuel Martinez: Of course, if you don’t mind, what I tell all the guests is if you want to start off and just tell me a little bit more about you and kind of where you grew up, and then eventually what got you kind of interested in technology. Ruben Sarino: Yeah, that’s a long story. So I think this is the perfect venue for it, right? So let’s see, where I grew up. So my dad was in the military. I was born here in Las Vegas, and right at five years old, moved to about six countries, including Japan, England, and got to travel around, all around Europe, and ended up back in the Philippines for a little bit. Ended up in college in California, went to school in the Bay Area, San Jose State, and then have since moved all around the US as well. So now I’m back in Las Vegas, and that’s where we met. Manuel Martinez: And what is it that kind of got you interested in technology, doing all that? Because I know that you spend a little bit of time in Japan, the Philippines, and I’m sure living in different countries also gives you a different perspective on not only how different countries, not just culture-wise, but the things that they value, don’t value, and like in Japan, like technology’s a big thing. So I’m assuming that had some influence, possibly on what you ended up doing later on in life. Ruben Sarino: Yeah, I think, as a kid, I was always into video games, always looking for ways to beat the system in the video games, and then I moved to Japan, and here during the 2000s, everybody had these amazing cell phones, and everything was so digitized, and the experience was so seamless. And I remember thinking to myself as a kid, Japan has figured it out, and has solved a lot of our day-to-day problems to make living a lot smoother, right? Let’s say commuting to work or buying things. And again, early 2000s, so ordering from an app wasn’t really a thing then. But then I got to travel also to third world countries, developing countries, and seeing those same human problems without those same solutions, and thinking to myself, there has to be a better way. And so technology has always, I’d say, fascinated me because at the end of the day, we’re ideally using technology to solve human problems, day-to-day problems, and really to make our lives a lot easier, because why work harder, right? So technology is a great way to help bridge the gap. Manuel Martinez: And you mentioned day-to-day life. Kind of seeing the differences between a third world country or even a developing country and somebody like Japan that is so technology advanced. Did it feel seamless? Like when you go to Japan, it’s not like, oh my gosh, I have to go and do these things because it flows very well. Like I know people that have gone there, and it just, it seems, and you kind of touched on it a little bit, a part of daily life. It’s not like, well, I have to go out of my way to kind of use technology. It’s built into where it almost feels, I’m gonna say, invisible, even though it’s there. Ruben Sarino: Yeah, that’s the best kind of technology, right? And you hit it spot on. I think, I remember growing up and things were just seamless, right? The way you interact with technology, you don’t think of all of the small systems that build it, but you tap a card to pay. This was, again, early 2000s. So this was like revolutionary, but you tap a card and that’s how you pay for things. That’s how you get into the subway. That’s how you get around. And nowadays that’s, or sorry, traveling to a developing country where I still had to then wait in line to get a ticket, to ride the train, if they had a train in the first place or get a taxi. It was, it’s just mind blowing, right? So being able to see the difference, I would say, like that kind of opened my eyes to like asking, I’ve always been a curious kid, right? Breaking things and taking things apart. And like I said earlier with video games, right? Like I’m always trying to see like, what’s the underlying like technology or system underneath so I can make my life easier, right? So at any rate, yeah, that’s what fascinated me about technology is what’s actually going on underneath that’s helping life become seamless. And then kind of seeing that contrast early on as a kid made me realize like, wait, we can apply probably the same systems to a developing country or to our day-to-day lives or at work. And that’s again, what’s fascinating to me about technology. Manuel Martinez: You kind of grew up, you bounced around and what is it that eventually got your career started? You know, did you think like, hey, I’m gonna go into tech or was it more like, I’m just gonna find a job or go to school or, you know, kind of what was your first step? Ruben Sarino: My first step out of high school, let’s see, travel a lot. So I traveled all over Europe, got to experience a lot of different really cool things. And then I had to really hunker down, right? And I moved back to California after, you know, living overseas almost all my life. And I started going to school and nothing really interested me, except for cars. And I was just fascinated about cars and, you know, everybody has a great car story, but, you know, I come from a huge car family. My dad was a mechanic in the Air Force. So I’ve always been working on cars. And I eventually got the opportunity to work for a company that took old designs for car parts for classic British cars, and they remanufactured them and went to, you know, various countries to make them and really become the major, if not the supplier for restoration parts for cars. And I got my first job as a, you know, salesperson there and really got to learning what it takes to, and really, I mean, it’s such a small company. You got to learn about the supply chain and tooling and engineering and how do you go from this like, you know, schematic from the 1950s and 60s into a part that sits on a shelf that we’re shipping out to a shop that’s doing a restoration. And at the time, the company wanted to expand the product catalog for the Mazda Miata because they were, they saw, they were sort of ahead of the curve and seeing that the Mazda Miata was going to become a future classic, which now, I mean, you can’t scoop them up for less than 10 grand if they’re in good condition, but I digress. So like, I, yeah, I was working on them, you know, just building them for, you know, the racetrack and doing track days and whatnot. And I got put on this team to, you know, help the marketing team understand how, what parts do we need at our catalog to increase the customer base? And I was just so fascinated about that. Like, wait, you’re telling me that we could just add more products, that we add more sales by adding more sales, we can add more products and we just kind of keep that cycle going. And at the same time, I was still, you know, going to school and I, in the process, started a honey business and I was fascinated with branding and what I learned at that company with, you know, with marketing and getting products on the shelf. You know, I said, hey, why not? You know, at this time I’m 22 and I just dove right in. I learned as much as I could about branding and merchandising and eventually got the honey into Whole Foods and local Whole Foods and other specialty retailers around the central coast of California. Manuel Martinez: And that came, I’m assuming you mentioned a lot of that from that car parts business. Ruben Sarino: Yes. Manuel Martinez: Is understanding, you know, how to build this supply, but you don’t just build the supply and say, I’m gonna make car parts for a Miata and I’m gonna make, you know, ball joints and I’m just gonna make a bunch of these and people will come and buy these eventually, right? There’s a process to understanding what is it that we’re going to manufacture? How did that come about? How were you involved in learning, okay, this is what we’re gonna build because you talked about it like, hey, we build more parts, people buy them, we have more revenue, now let’s build more parts. So how did you kind of go through and determine this is what we’re gonna build or as part of the team? Ruben Sarino: So I was, you know, kind of, because I was a huge enthusiast and I worked on the cars myself, I was more, I would say, kind of like the marketing teams, like insight into what the actual demand would be, like what could actually, what would actually sell off the shelves, right? And so learning that part and kind of like watching how they went through that analysis was quite interesting, but on the British side, right? So they’ve been in business for about 60 years at that time, 60 years. And so they had this really interesting problem, right? There’s a lot of British car owners, classic British car owners that did not have a place to buy parts and pretty much had to abandon these amazing cars because of that. And so they found this opportunity to essentially fill the quantity and quality problem that, you know, if you know anything about British cars, they break down all the time because the quality is terrible. So they made improvements and essentially re-started that whole supply chain of parts for people to keep their cars on the road. And so now they’re the manufacturer for all those parts. Manuel Martinez: And then on the Miata side, you talked about, you know, hey, we wanna get into this market. What did they decide? Hey, we’re just gonna start manufacturing every part or, you know, were there specific ones? Like how do you determine, how did you establish the problem instead of just saying, hey, we have a solution, right? Cause it’s a supply and demand thing. Like you can create all this supply and then there’s no demand. And that cycle that you talked about never happens. Or, you know, you’re trying to find like, what’s the demand and then fill it with supply. Ruben Sarino: So there was already a demand. I would say, you know, when you’re also, car parts are kind of interesting because you sort of like, you know, I’m not an expert on the industry, but so this is like what I know from just, you know, what I’ve done. But when you’re filling a catalog, you’re just throwing cool stuff in there, seeing what sticks and then watching the numbers that ride the traction. We had a great customer base that we could sell to. And from there, we effectively tried to understand what did they want. We wanted to get ahead of, you know, trends that were, you know, coming in like roll bars were a huge thing for the Miata because to get on the racetrack, you have to have a roll bar or roll cage. So that became a huge selling point. But then as the cars aged over time, we saw products that were in demand because they were common failure points. Like a soft top is an example. Or there are common problems that, you know, come about from having such a small car that are loved by Americans that are taller than the average Japanese driver. So those modifications were always like cool add-ons to the catalog because you could now sell these modifications and, you know, people would buy them. So just, if we also listened to what the industry, you know, people on forums were saying, like, if you could, man, I wish I could, and then fill in the blank. And if there were enough of those, we would work with our engineering team and see, hey, is that something we can actually manufacture? Manuel Martinez: And I’m glad you kind of touched on that point because I think a lot of times people, I write about this a lot, is, you know, solving business problems with technology. And how do you solve this problem? And I see this, and I know that you probably do as well, and the industry is, hey, I built this thing, there’s this cool thing, and then you’re just trying to push instead of a pull. And it sounds like you guys, at least in that industry, and the reason I bring this up is it’s a transferable skill. I want people to know that there are skills that you can pick up along the way in different industries. And that’s the one is, what’s the problem? And you’re looking at forums, looking at, hey, I wish I could blank. You start to see enough of those. Okay, that’s the problem. Now I can solve it instead of saying, well, I’m gonna create, you know, fancy tail lights, and say, hey, everybody, you should get these, you should get these. And people are like, well, I don’t want those, I don’t like those. That’s not what we want. But you kind of looked at what is the problem? People are like, well, I want to, the problem is I want to take this on the racetrack. In order to do that, I need a roll cage. Okay, we can fill that product, or sorry, we can fill that problem or solve that with this solution. Kind of being able to understand that the way to solve problems, whether technology, with car parts, whatever it is, you have to know what’s really the root cause of what’s the problem and not just try and say, well, there’s this cool technology, AI, which we’ll get to at some point. It’s like, hey, there’s AI, and I’m just gonna put something and hey, everybody use it. And I think that’s kind of what’s been going on now as opposed to, sure, what’s the problem I have? Can AI solve it? Maybe it’s just something else. Ruben Sarino: Yeah, I mean, in your day-to-day life, and I think going back to my early experiences, you know, kind of to Japan, I would remember traveling to, you know, for example, the Philippines and just being so annoyed as a kid because, you know, where I was growing up in Japan, this wasn’t a problem, but here it’s a problem. And I’m sure, you know, if you’ve done any traveling yourself, you probably say like in the United States, this would have been solved, but, you know, if you’re traveling, say to Europe, it’s like, this is a huge problem for them. And, you know, I’ve realized, like, sometimes it’s just like looking at the problem, right? But to kind of go back to the whole, like, push and pull of products, now that I’ve, you know, have more of a career, I mean, that was almost maybe, yeah, like about a decade, more than that at this point. That was a long time ago. And now that I’ve had more experience and, you know, I’ve built, you know, two, three businesses since, I’ve realized that the strength that they really had is their distribution network and the customer base. And by having such a strong distribution network, that is really the key to, to a successful business like that, because you don’t really need a push or pull more so, I mean, you’re the manufacturer. So as long as you have a bevy of shops that you could sell to, or a bevy of like, you know, great customers that you can sell to, or a community that you can sell to, there’s always a way to eventually, yes, push it into the market and just kind of see what sticks. Manuel Martinez: What sticks, that’s cool. So then, you know, you started this honey business, you learned about marketing and, you know, you mentioned you started a couple of different businesses. Is that, that honey business, is that kind of what got you started and said, all right, I want to do something else. Did you always think to yourself, I want to be an entrepreneur or, Ruben Sarino: Sure. Manuel Martinez: Hey, I want to try and, marketing’s my thing, sales my thing, technology, what kind of progressed from that point? Ruben Sarino: So, the honey business was purely by chance. It was part of a lab at the college that I was going to at the time and, met a beekeeper who had terrible packaging and branding. And he had a really modest idea and I wanted to go bigger. You know, and I think the car parts company gave me the confidence, albeit maybe it was also a little like, you know, ignorant, but I was just like, hey, I can do this, if they can do it, I can do it. So I went full steam with it. I had a partner at the time and we, you know, essentially worked with all of these family-owned apiaries, which are, you know, beekeepers, who produce their own honey. And I would go to them, I’d source all the different types of honey that’s native to California. And we packaged it and sold it to, you know, various specialty grocers. Manuel Martinez: And then, I mean, I’m sure you learned a lot running a business as well, right? Cause it’s one thing, like you said, it’s ignorance, but sometimes that’s a good thing, right? It’s just, you don’t know what you don’t know, and then you kind of run into it. And- Ruben Sarino: If you know too much, you will never start. Manuel Martinez: That’s kind of what I was going to get to is, sometimes you, people do too much research. And I’ve done that before where you’re like, evaluating products or like, hey, should I buy this thing or this, you know, like for example, like the cameras, when I was looking to start the podcast, like, should I buy this camera or this camera or this camera? And at some point you’re just like, it doesn’t matter. Like just pick something that meets the minimum requirements or like, you know what, I’ll figure it out as I go and just kind of move along. Ruben Sarino: Yeah, get started and then course correct. Like, you know, it’s always often said, yeah, just get started because getting started is the hardest. And then you realize, well, this camera is, in the case of the cameras, you know, you fall short here. So the next camera I get will have these requirements and maybe I’ll invest in some lighting, you know, on top of that, so yeah. Manuel Martinez: And the same thing with, and I’m sure that you’ve come across this as I buy, is bouncing around in my career. Like, I think I want to do this. And at one point I was like, I’m going to be a server guy. And I did that for a little bit. And I’m like, oh, networking sounds cool. I’m going to go do networking for a little bit. And I’m like, nope, don’t like that. And you just, again, you course correct. And I think sometimes a lot of times, you and I have talked about this offline, is people who are just getting started or people who have been in a little while and say, oh, you know what, cybersecurity is the big thing. Like, I want to get into cybersecurity. I want to be network, you know, the networking engineer. And I’m like, well, try it and see, because I had that same misconception. It’s like, I want to be a network architect. And I started doing it. I was like, God, I don’t want to do this. This is not for me. I like more of the server infrastructure side. Ruben Sarino: Yeah, actually the car parts, just kind of to put a, you know, round that corner. I initially wanted to go into the car parts company because I wanted to be an engineer and design race cars. Manuel Martinez: Okay. Ruben Sarino: And then I realized what the engineers actually do, that design parts. And let’s just say the career lifestyle wasn’t for me. I enjoy the interpersonal, I enjoy the dynamic nature of sales and yeah, engineering just, it sounds cool. And when you’re on the racetrack, it’s really cool. But what I didn’t realize is, and maybe this is just, again, being a little ignorant, is that one day at the track is a whole year’s of research and engineering and developing product or, you know, developing parts that eventually make it to a race car and then eventually makes it to a race. And there’s a whole bevy of teams or engineers and people supporting that effort. And so quickly I realized that wasn’t for me, you know, sitting behind a computer, designing, you know, looking at really small parts all day long, just, it wasn’t for me. And I realized just by kind of, you know, hey, let’s just get started somewhere in the car industry or in the manufacturing industry. I gave it a shot and I realized I had a, I liked another part of it better. So anyways, yeah, to your point, just get started in the general direction and the course correct. Manuel Martinez: So then now you’ve got this other business, you figured out while, you know, in school and you’re kind of doing this, so then what’s– Ruben Sarino: So I moved to the Bay Area because it’s 2013. Manuel Martinez: Okay. Ruben Sarino: Well, you know, cloud came along, the app stores came along, and I learned that people were making some crazy money, making the silliest apps, you know, apps of all sorts, right? Solving real problems and some solving very, you know, simple problems, right? Like the flashlight app, if we can remember that for the early iPhones, right? And so I was just fascinated with this ability to make money out of just kind of thin air with just an idea. And so San Jose State was where I went. And I suppose just by, you know, I said, hey, like if I’m gonna go anywhere, I should go where there’s tech. And at least I’ll be in the general area, I’ll bump into the right people eventually. And I did, my first semester there, I got straight into, you know, networking with some cool entrepreneurs And I think, you know, I wasn’t ever the best student. I will say school was not for me, but I love rolling up my sleeves and getting my hands dirty, and I’m a very hands-on person. And so my first semester there made sure, I’m gonna network with as many entrepreneurs that are in the Bay Area, and specifically San Francisco in order to get in on this action. Because again, it’s 2013, and there were apps flying everywhere, and people were making money in all sorts of cool ways. And you know, why not? Just figure it out. And that’s how I got, you know, started in the Bay. Eventually the honey business shut down, learned a lot about the importance of distribution, and networks, and really understanding like your supply chain and whatnot. And eventually got a gig at the Apple store, right? You know, just job in college, but learned a lot about how, I mean, in a way like technology works as a whole. Even though it was on the hardware side, it was how do people solve business problems, right? We had a huge emphasis on solving, or like helping local businesses through our business program and learning how to sell without selling, and really uncovering problems. I mean, if, you know, Apple doesn’t do corporate selling, or the corporate sale of sales, but man, I mean, like they teach retail employees how to do proper discovery in a meeting, you know, just one-on-one. And they really teach people how to essentially not make it about them, right? I mean, you don’t, you’re not compensated on, on like how you sell, on, you know, what you sell, there’s no commission. So really it’s about then really understanding what is that person’s problem? Like, what are they actually trying to solve? What are they using the products for? And then making recommendations based on that. And one, it yielded to greater customer happiness, but also two, you end up selling more because you’re actually solving a problem and there are other, you know, add-ons that you can get add to, so. Manuel Martinez: And is that, when you say that they teach you that, is it like a sort of program you go through? Is it structured? Is it, you know, kind of shadowing people? I’m just curious how they go about teaching that because you’re right. Doesn’t matter what Apple store, I don’t go in there that often anymore, but when you go in, it’s a very similar experience. At every one you go to, like if I go, you know, like I said, if I go in the Bay Area or if I go to a smaller town, let’s say, or not even a smaller town, but if I go to Austin or if I go to New York, again, the building might look different, the size or whatever, but once you go inside, it’s very similar. So how did you go about, you know, like what was that method that they went about to teach you more about sales and really uncovering problems instead of, you know, most people when they think sales, it’s, hey, here’s this new MacBook, push it, push it, push it, and it sounds like that wasn’t the approach. Ruben Sarino: No, no, no, it was always about the customer. I mean, and I think being obsessed with like your customer’s problems and trying to solve your customer’s problem with the tools that you have at hand, I think that’s what Apple does really well, right? And you can’t do that unless you ask a lot of great questions. So they have a method that they teach and wait, and I don’t know if they still do it this way, but I think then was probably like, it was a great highlight of that, you know, retail program for Apple. Because again, yeah, they, when I went later on into the corporate world, I’m learning all of these skills and it’s like, it’s the same thing, it’s just a discovery. And when you do a really solid discovery, you know, you’re uncovering problems and you’re finding out like the implications of those problems, you can really help guide the customer to a successful outcome. Manuel Martinez: So then you’re picking up this skill now of really doing discovery and it’s not just selling, right? But it’s selling through problem solving, right? Ruben Sarino: Sure. And at that point, I mean, like you said, it’s gonna sell itself, right? And you’re gonna have a happier customer. I’ve never felt at an Apple store that they’re pushing a product on you. Like they’ll ask you those questions like, “No, I’m not interested.” You know, okay, if you have questions, come back. They’re always like, if you have questions, if you have questions. So then you get this, you know, knowledge that you probably, I don’t know if at the time you did or didn’t realize that, “Hey, this is gonna come in handy later on.” But what transpires as you’re kind of working your way through college, you’re meeting all these other entrepreneurs. You’re thinking to yourself, like, “I’m gonna build an app.” Like, did you put those three skills together and say, “All right, I’ve got this now.” Ruben Sarino: Not necessarily technology. So at the time I knew cybersecurity was this amazing, cool part of technology, but I didn’t really know much about it. And I made a friend in one of my classes that had a really quirky teacher and, or professor. And he’s now my business partner, but Emmanuel and I met and he eventually went off to do cybersecurity at NASA and all sorts of cool places. And I’ll let him tell his story eventually, but I learned more about security and kind of like the importance of, you know, at the time Stuxnet was this scary, ominous thing. The OT threat, like as cloud was, you know, becoming a thing, so were, you know, technologies that could control your thermostat as an example, but also like, you know, other parts of corporate life, like, you know, copiers, where you could, you know, or air conditioning systems that could be controlled through a centralized place. But nobody was thinking, “Well, how do we secure that to prevent bad actors from entering that?” So, you know, Target, as we all know now, was compromised because of that. So I had someone in my life that, you know, really inspired me to look into cybersecurity because, you know, coming from a military family understood the importance of security and, you know, kind of the implication of what happens if you don’t secure things. And, you know, cyber also, you know, she, you know, she worked at a great cybersecurity company and she was telling me about the massive paychecks that sales reps were making. And so put two and two together, and I said, “Cybersecurity sounds like a great place to start after college.” So I applied to so many companies and eventually I made my way, I got referred into a company called CrowdStrike. That’s where I got my start in corporate, you know, cybersecurity career. Manuel Martinez: And getting in there, you started on the sales side, is that correct? Yes. So on the sales side, you know, thinking, “Okay, I want to do security, I want to sell security, but I want to sell security because you know that there’s a problem.” Like similar to, sounds like everywhere else, the problem, you seem to be really good at identifying problems and wanting to solve them. So you talked about the car parts, you know, and then eventually the honey business, like, now there, the problem wasn’t so much on the consumer side, it was more the business side, like, “Oh, the packaging, all this is terrible.” You know, and now you’re learning skills on discovery with Apple and, “Hey, I want to go through.” Ruben Sarino: Sure. Manuel Martinez: I would be a fool to say that a lot of the different areas that I tried wasn’t motivated by money. I mean, especially at that age, you know, in my 20s, it’s like, “Oh, I can make money doing this as a network person or as that, like we mentioned before.” But now you get in and I would think on the security side, it’s got to be, “Okay, I can make a lot of money, but there’s a real need for this.” Ruben Sarino: Absolutely. Manuel Martinez: So how do you go through and really determine, “All right, I like the cybersecurity, I think I can do this.” You get your first role, kind of what was the expectation that you had going in, and then what was it really like once you were in that role? Ruben Sarino: Yeah, so I wanted to, I was hungry, right? So like the same, you know, same, I think this is a common theme in my life. I said, “Hey, I just want to get in to the best.” Because I realized, you know, the importance of, even if it was Apple retail, people see Apple and they recognize that it’s just like going to Harvard or it’s just like going to, you know, it’s your part of this community that like, the baseline is really high. And I wanted to do the same in my corporate career. And CrowdStrike at the time was, you know, was a series B startup that was making huge waves because of its EDR product. And I said, “I need to get in, I don’t care how. It’s going to be a big, you know, they’re going to be a great company.” I didn’t realize how big it was going to be, but I knew that they were doing some cool things. So I got a job as a sales development representative, which is, you know, if you can get out of college and become an SDR, I mean, at least, you know, when I did that, Manuel Martinez: SDR is? Ruben Sarino: sales development representative, you know, you’re, it’s an entry-level job, you’re just dialing for dollars, as they say, right? You’re just making as many calls. And, you know, at the time the calling was still huge. Now I don’t know what the reps are using, but I’m sure it’s a lot of AI and a lot of outbound that’s assisted by AI. But I mean, talk about learning how to just go through and develop a pipeline, right? That is the foundation of a pipeline. And if you ever work in a startup or if you ever, you know, end up owning your own book of business, like that is what is key to jump-starting that pipeline. I supported four amazing reps in the Texas region. And eventually they, you know, sort of mentored me into, telling, they did a great job of showing me what was on the other side of just like, you know, dialing for dollars and like cold calling people all day long and sending a thousand emails a week and, you know, doing discovery calls, right? What happened after? So they did a really good job of not just like, you know, hey, like give me the leads, but also let me show you what’s going on with the lead and the deal. And here’s what would, here’s how it progresses, right? And that just fascinated me even more because, you know, like as an SDR, your goal is to become an account executive and eventually make it into the field and go close those big deals. So that, I mean, I gotta give it to those guys because they really, you know, did a good job of just kind of like, I don’t know, kind of like fostering that curiosity that I had, even if they didn’t know. But also CrowdStrike at the time did a great job of mentoring all of the people that came in to really, with the mindset of, hey, you will be the next account executive. So we need to ramp you up as fast as possible because these account executives will eventually become, you know, field sales people. And so at that time of growth, it was just like, hey, let’s just get everybody ramped up. So I was learning a lot all of the time. So, yeah. Manuel Martinez: And a lot of that learning is good and having a, it sounds like they knew and you talked about it before, it’s like a pipeline. They also have like a talent pipeline. Ruben Sarino: Absolutely. Manuel Martinez: Because you’re starting here and you’re kind of, they know that the natural progression is people are gonna wanna do more or the next thing. In most cases, like some people are like, all right, they reach a certain limit or hey, this is, maybe I don’t wanna move on there, but as, if they move out, like let’s say they leave CrowdStrike or they move to a different division, they’re still a position to fill. So they didn’t necessarily, or it doesn’t sound like you necessarily went through and asked them and said, hey, can you be my mentor? Was it the types of questions that you were asking them? What like, how did you establish that relationship with these account execs? Cause I’m sure, like you said, maybe they knew or didn’t know, you know, that they were fostering that curiosity, but there’s also in my experience, there’s something in you that makes people open to sharing information because I’ve been on both sides. I’ve been where I’m like you, I’m naturally curious, I’ll ask questions and then that’s probably enough for them to say, oh, well let me here, here’s how this works. Ruben Sarino: Right. Manuel Martinez: And, or maybe they pushed information and then now you’re kind of going through like, oh, well tell me more. Ruben Sarino: Sure. Manuel Martinez: I’m just curious what your experience was in that because I’ve, like I said, I’ve been on both, where I’ve given information and you see that, that person does nothing with it or they start eating it up and you’re like, oh man, let me feed more, let me feed more. Ruben Sarino: I did a lot to ask questions. I would say, I probably asked more questions than I really needed to and, you know, eventually they were like, well, you know, if you’re so curious, let me just like share, you know, what’s going on. So I think the cadence kind of, it wasn’t just like a, hey, here’s all the sales updates. Like it was more about like, okay, how do we like, you know, how can I help this guy out? You know, I don’t know if, yeah, I don’t really have a good answer for that. I never really thought about that. I mean, I just like to ask a lot of questions because ultimately what they’re doing, I want to understand too, if that’s the direction I want to go. Like it sounds cool and the outcome is cool, but you know, what I learned kind of in the engineering, right, is the day to, is like, you know, is getting, is racing for a day, 364 days of pain that I don’t want to go through. And so I wanted to know what does the day to day look like for you? And is this a career that I would actually like to pursue? So I was always asking questions, you know, and kind of testing my hypothesis. Manuel Martinez: And I like that, that you were going through and said, well, I think I’m going to do this, right? And is the payoff worth it, right? And it sounds like for most engineers, that one day is worth it to them. For you, you’re like, it’s not worth the trade off. For CrowdStrike, I’m assuming it was worth the trade off. And did you kind of end up moving into one of those roles? Ruben Sarino: So I didn’t stay at CrowdStrike, but I did continue the pursuit to become an account executive. And I did it more so because that was the path that I thought I wanted and I continued down it. Ended up at another startup, Series A startup. They did not make it, so I got laid off, ended up at another company, and realized I did not like selling to the SMB persona. And after that, I was kind of rethinking like, man, what do I actually want in a sales career? Because I thought I liked selling. And then I realized, okay, I don’t like selling to this persona. I like selling to the enterprise. And I don’t like selling this type of product or a product that sells this kind of perceived benefit. I wanna sell something that actually makes a huge difference. So I stumbled upon by chance. I got in touch with, how did I get in touch with them? Anyways, I got a contract role. Initially it was supposed to be for 30 days, turned out to extend to six years. (both laughing) And I ended up, as the go-to market, I don’t know what the actual title was, because I had so many hats. But at the end of the day, I put together the internal processes and the HubSpot and the marketing. And eventually I took over the marketing for a while, thanks to the pandemic. And it was just a really amazing experience to learn so many things, so many inner workings that go behind a startup. And, you know, as a seven, eight person startup, on the US side, and it was a very, like, just eye opening experience. I don’t know if you have any questions around that. Manuel Martinez: I do, because one of the things that, and I didn’t realize it at the time is, you know, you mentioned you went from, you know, CrowdStrike, was it, again, Series B, but it’s still a startup, these different startups. What is it about either that culture, or is it really trying to be on the cutting edge that called to you and said, “Hey, I wanna do that,” as opposed to saying, especially after CrowdStrike, like, “Okay, I’m in here, sure, they’re a startup. I’m gaining the experience,” right? Probably because they’re a startup and they, you know, they’re growing at a rate that they’re willing to take on these people that maybe have a little bit less experience. Now that you’ve gained some, what made you continue to stay in the startup kind of ecosystem as opposed to saying, “You know what? I think I’ve established enough of, enough experience, enough knowledge. I wanna go more to an established company.” (both laughing) Ruben Sarino: You know, actually, one thing I loved about Apple is, you know, you’re, especially in the Bay Area, you’re always selling to somebody that works in tech. Right, big tech usually. And I remember he’ll never know that he gave me this advice, but I spoke to, he had just retired like the day before, final day of his career, CFO of a large company. And I was like, “Hey, you know, you’re the CFO of a large company, like, you know, somebody that’s trying, that’s hungry and trying to get into the corporate game. You know, what advice do you have?” He was like, “Don’t go into a startup.” Manuel Martinez: Don’t, go? You’re like, “Sounds great, I’m gonna do that.” Ruben Sarino: Yeah. And at this time, I think I’d already gotten the interview for CrowdStrike or, you know, and he, and I said, “Why? Why not? That’s, you know, I mean, it kind of like, especially with the culture in the Bay Area, it’s like, you know, especially at the time, it was like, everybody had a startup. Why wouldn’t you do it? Right? And he effectively said, “You have nothing to offer. You don’t have skills that were kind of like created and hardened over time that you would have like, say working at like HPE or something, like, you know, IBM, Any old legacy company, you know, you spend six years there and then you go to a startup and you take all of those processes that you learned at IBM or HPE and you add that to the startup. Manuel Martinez: So it’s more about adding value to the startup. Ruben Sarino: Yeah, yeah. Manuel Martinez: Okay. Ruben Sarino: So anyways, I don’t know why, I just, I thought about that conversation I had with that guy. I don’t even remember his name, but man, I haven’t thought about that in a really long time. But yeah, so against better advice, I suppose, I did exactly what he told me not to do. And I think what’s always drawn me to the startup is that my impact is greater. I feel is greater, right? Because if you are playing on a smaller team, your impact is also, it’s more seen. So I think like having that pressure and that accountability has always, in a way, I’ve enjoyed it. I love the entrepreneur story and I’ve always been an entrepreneur. So I’ve always had an entrepreneurial spirit. And I think, I don’t know, I just, I didn’t feel like I fit into the Cisco’s of the world. I had friends that went into Cisco and, you know, that’s amazing, right? There’s nothing wrong with going to the amazing corporate route or the established corporate route. I don’t know, maybe I’m a little bit of a maverick. I just didn’t draw, I wasn’t drawn to it, to be frank. Manuel Martinez: Right, and that’s fine. I was just kind of curious why, because again, some people are drawn to it for a reason and some people aren’t. And, you know, there’s, especially when you talked about, you know, hey, this is where the money’s at. I was just curious, sometimes I’ve seen people that go through, it’s like, I’m gonna go to the startup realm because if it takes off, boom, I’m good. Whereas it sounds like you, like I just wanna have more of an impact. Like I wanna know that the work I’m doing has an effect, whereas not that it doesn’t in a big corporate environment, you know, like I’ve worked for them. So it is, it just doesn’t always feel like that, like I’m a smaller cog, right? Like there’s impact, but it’s not like, like you said, I’m a smaller team, like I’m not that person. Ruben Sarino: But on the other hand, I think maybe if the large company structures it in a way where, is structured in a way where your inputs, like you can see the outcomes, you know, the bigger outcome directly. So I think there’s like kind of that give and take. But I also knew in my gut that I always wanted to be a startup founder or found something like my own company. Like to be an owner, right? From day one, like I remember driving to San Francisco to go do this corporate media event. And for the startup that I was being, that I had to get mentored by for my class. And I just remember thinking to myself, like I wanna be those guys. I don’t want to be like forever, just, you know, like in the sales career. I mean, I love sales, don’t get me wrong, but I wanted to, yeah, be an entrepreneur. I mean, just found my own thing. And like I said, I mean, I guess the common theme is I like to just get in, I like to learn. And then, you know, how does that help me towards my greater mission, right? And so that’s why the startup made sense because I got to see more of the inner workings. Whereas I felt that going to a large company insulated me from a lot of the, like the minutia that I wouldn’t otherwise get to see, right? Yeah. Manuel Martinez: No, and that’s good because, you know, you hear both sides of it, right? Like everybody can be an entrepreneur, but not everybody’s built for it, you know, different things like that. So maybe if you, this might be another area where if somebody’s like, “Hey, I think I want to start something.” Like, well maybe work for a startup and see if that’s really, you know, get that exposure. Well, we talked about it, right? Course correct. “Hey, let me try it. Not for me.” Or, “Hey, maybe this is.” And you know, you kind of develop from there or you say, “Hey, you know what? I like more of that established, that corporate structure. I want that structure.” Again, that’s, there’s no one right way. It’s just try different things. And that’s why I’m glad that you talked about what drove you to do that. And that’s, again, the whole reason behind a lot of this podcast is expose people to, you know, different, just different mindsets, different people, because I’ve run into you and like, “Hey, I’ve gone start up to start up to start up and I’ve talked to other people.” And like, “I’ve been at the same place for 20, 25 years.” Again, there’s no wrong or right way, but hopefully just explaining that I’ve always wanted to have an impact. I’ve always had that entrepreneur, like, “I want to do stuff.” There’s someone that’s listening that says, “Hey, you know what? That’s how I think. Maybe this is the route to give it a try.” Ruben Sarino: Yeah, absolutely. I think, yeah, if there’s any takeaways from this podcast that I’m seeing, you know, coming up, it’s, you know, and I’m reminding myself, like, just go in, try it, of course, correct. Because, I mean, look, like in the startup world and even in just general sales, your initial attempt is not, it’s 98% not going to be correct, right? Generally, you have to pivot to somebody else if you’re selling or if you’re, you know, maybe your messaging is off and you get a ton of, “Hey, stop calling me. You need to pivot,” right? So I think it’s always just get started. And, of course, correct, but also have that bigger vision in mind, right? Like, what is, I always actually ask myself once a year, you know, it’s around that time of the year, I kind of have a one-on-one with myself. And I say, you know, how do I, I always start with like, how do I want to feel next year? Not like, what do I want or what do I want to do? I always kind of start with, how do I want to feel? And from there, it’s like, then I kind of understand, okay, what do I need to do to feel that way? And so that’s how I course correct, I suppose. I don’t know. I don’t know why I brought that up, but. Manuel Martinez: Well, no, it’s good, because I have a friend and he’s been on the podcast where he talked about something similar. He has like three criteria, right? Where he’s like, you know, I don’t remember them, of course, but it’s something like, you know, do I enjoy the people I work with? You know, am I able to kind of go through it? And he says he does this on a regular basis and that’s what he goes through. He’s like, here’s my three things. Do I like the people that I work with? Do I, you know, am I able to make a good living? And I don’t know what the other one is. Maybe it was something like, am I learning a lot? Or do I feel stagnant? So it sounds like you’re doing something different or something similar. It’s a little bit different. It’s like, well, how do I feel? And then you kind of start to work back from there. Like, I want to feel like I’m making an impact. Okay, well, how do I do that? Okay, well, maybe I go to a startup or, hey, I want to feel like I’ve, you know, I’m established. Okay, well, maybe it’s no longer the startup realm. I mean, I’m not saying that that’s what you’re thinking, but kind of working backwards that way and establishing what that end goal is. I like that approach. Ruben Sarino: Yeah, because I think the worst thing that we can do for ourselves is do something for extended periods of time that don’t excite us. So I think, you know, if you’re feeling kind of stagnant or bored or, you know, you’re looking for that next challenge, but you don’t know how, I think just start with, that’s a great place to start. It’s just, how do I want to feel next year? I want to be excited. Well, excited about what? I’m excited about what I’m working on. I’m excited about the people I’m with. I mean, you know, there’s so many ways. And then from there, it’s like, well, if it’s just the people, but you like what you’re working on, okay, maybe switch teams, find a different initiative. If it’s the company, maybe it’s time to try something entrepreneurial or start a side gig or start, you know, especially with vibe coding and AI. I mean, there’s so many ways to take, you know, years and years of expertise and turning it into a prototype software that you could then, you know, commercialize. I mean, if you want, you know, there’s so many things you could do nowadays to kind of like, you know, just dip your toe into the entrepreneurial realm, right? Manuel Martinez: Yeah, and I hope that people start, for people who don’t know exactly what they want to do. I think the way that you frame your, you know, your yearly check-in is a great way to do it. Well, I don’t know what I want to do. Okay, but maybe you have an idea of what you want to feel. Ruben Sarino: Yes. Manuel Martinez: Hey, how do I feel now? Okay, I feel stagnant. Okay. Well, how do I want to feel? Do I want to feel like I’m learning something? Okay, where would I learn something? And it doesn’t necessarily have to be that. So I think a lot of times, and I’ve run into people like, hey, as a kid, what do you want to be when you grow up? Or what do you want to do? And your just always like, ah. I want to be an architect, a policeman, you know, things like that. And people are like, well, I want to get into cybersecurity. Hey, why? Like, what is it about cybersecurity that excites you? Well, that’s where all the jobs are. Okay, is that really a good reason to get into it? I mean, maybe it is, but again, you have to determine that for yourself. Ruben Sarino: Yeah. Yeah. So for me, like this year, like feeling secure is one, is what I want to feel like in 2026. And that can come from a multitude of things, right? And so to use the cybersecurity example, I think, you know, being able to provide for your family as an example is a great way to feel secure. So anyways, that’s why I like to keep it very open-ended because, you know, I kind of go through life and maybe like from month to month, like, oh man, this month was like particularly, I felt particularly bored or I felt particularly like insecure about one part of my life, right? So how can I, you know, address that one part of my life so that I don’t, you know, maybe I need to shift some priorities. But yeah, that’s just how I look at it. I don’t know. I don’t know if that’s like a huge quotable, you know, part of the podcast, but that’s how I like to start my check-ins. Manuel Martinez: No, I like it. Ruben Sarino: I don’t even know how we got off. Sorry. Manuel Martinez: Well, and that’s why I kind of like this forum, right? Is because it’s like something you said kind of brought me there. And we start going through as opposed to… Ruben Sarino: Yeah, don’t let me derail your podcast. Manuel Martinez: No, no, you’re good. Like this is, I kind of like that. Like I have a general sense of what I want to do and what I want to cover. But then again, I never know what you might say or what thought or question that might trigger. So then in this go to market position, sounds like you learned quite a bit, especially because you’re doing everything. Like you became the marketing, you became, you know, the salesperson, a little bit of everything. How much of that was just kind of your prior experience, like the little bit with the honey, right? I see in that position, like how much of that do you think was prior experience versus I’m going to learn and build skills that maybe not that you didn’t have them, but maybe you had them, but they were very, maybe they weren’t as strong. Ruben Sarino: I would say I really… So the initial expectation for the contract was, you know, that 30 day contract was, take your SDR skills that you knew from back in the day and use them so that we can prove, you know, that the leads are not garbage. And so I said, okay, that’s easy. I could do that for 30 days. Ended up converting a lot. And the CEO of the company said, hey, do you want to just come on full time? And so I did. And six years later, that’s sort of what happened. And in the process, it was really organic. I mean, their HubSpot instance was a mess. So I went through and kind of cleaned it up and added some processes and added, you know, kind of just shaped it up to what I had seen in prior startups. And it just really, it just makes sense. When you, once you know the cadence and like how to sell and you know, what the outcome is, then everything else kind of falls into place. I don’t know if there’s anything specific you want to dive into. Manuel Martinez: So I guess the specific, and this will probably lead the conversation is, so in that role, like you said, hey, you had experience on the HubSpot and some of these other things, like how in those first 30 days, it sounds like it’s just the lead qualification. But then after that, as you started kind of moving up and gaining more responsibilities, would you say that as you moved into like, and they gave you the marketing, or you became a full-time employee, how much, like what percentage of the skills that you currently possess, do you think attributed to kind of moving in like, all right, for the SDR position, like 100%, right? Like I, for what they were asking, that was 100%. But then when they gave you marketing, you’re like, ooh, well, I have maybe 25% of the marketing and the other 75% I learned, or maybe it’s 50% and I learned the other 50%. So I’m just curious like, how much you learned combining all these different jobs. Ruben Sarino: Yeah, so going into, now that I think about it, I had to learn probably about like 50%, 60% outside of what I already knew. And only because, yeah, like marketing, I had no idea about marketing. Like what is PPC? What is SEO? How do blogs impact an inbound campaign, all of the campaign management? I didn’t understand any of that. And shout out to HubSpot because they make it so easy, but coming from previously from Salesforce, run environments, like the operations there were so much more complex that if you kind of understood that, then it made HubSpot a breeze. And then because your CRM kind of mimics your operations, like your actual operations, like what you’re doing, then it kind of just, for me, I extrapolated, well, what should we be doing? So, yeah, but yeah, as far as the marketing was concerned, look, I’m not a marketer by any means. So I had to learn how does blogging impact, I guess, all of your organic marketing and how does that convert into leads that then convert into opportunities that convert into deals. That was difficult. I will say probably, I still don’t have any, I would say I’m still like maybe a very advanced novice at it. If I have a marketing team, I definitely use them over my own marketing skills. But I would say after that, that engagement ended. And after six years, I said, well, what do I do next? So I took a month off in the process, I had a heart attack and then I kind of checked in with myself and I said, hey, how do I wanna feel this year? Manuel Martinez: Is that kind of when it started or like that checking in with yourself and how do I feel, how do I wanna feel? Was it after that? Ruben Sarino: No, no, no, I was already doing that. But after I had a heart attack, it wasn’t a large one, it was a small heart attack, but I spent four days in the hospital because they wanted to make sure I, my heart wasn’t failing on me. And I make a joke of it, but it was very serious. And I joke, but there’s, I always say to myself, when I travel or do questionable things like racing cars, the number one rule is don’t die. And so I almost broke that rule. So don’t die. But yeah, I had a small heart attack and I was listening to some, I love audio books and I can’t read books because I don’t have the patience, but I love audio books. And I was just listening to this audio book and it was like making me think, like what do I want to…out of the other side of this? Like, I’m in my late thirties now, like what do I wanna do? There’s this whole AI thing coming up though, what’s happening with that? And I don’t know if it was just by sheer luck, but Emmanuel, my friend from college who went off to NASA to do cyber, we had stayed in touch and I knew he was doing cyber stuff and I knew he was really knocking it out of the park. But he was, he hit me up out of the blue and said, “Hey, there’s this AI stuff, there’s this cyber stuff. I have this idea.” And in college, we had this wacky idea to start a sriracha business. That is a whole other story for another day. Did not work obviously, but we kind of vowed from that point on, like, hey, we do work well together. We like to create cool things. And I kept up with him and his entrepreneurial, his ventures outside of like his day job. So he reached out and said, “Hey, I’m working on this thing.” And, you know, can you just look at it and see if I’m, make sure I’m not crazy? And so when I get out of the hospital, he said, “Hey, you missed the call the other day. Is everything okay?” I was like, “Oh yeah, I just spent four days in the hospital, don’t worry about it.” He’s like, “Okay.” Manuel Martinez: Like, “Oh, okay, no big deal.” Ruben Sarino: I was like, “What do you have to show me? It sounds really exciting.” And ended up, he pitched me on this idea where we would take AI and apply it to cybersecurity. This was like 2020, early, late 2023. So kind of on the like ChatGPT, had just kind of come out. There wasn’t a lot of intelligence or information on the internet. And so we, I don’t know how to go into it without like divulging a lot of stuff, but pretty much he pitched me on this idea, this big vision and he showed me this very like, we call it the super secret slide, but this very like confidential slide that shows the architecture of this whole idea. And I was like, “Whoa, wait, this is really cool.” And then I thought, remember Ruben back in 2016 when you were like looking at CrowdStrike and kind of what they did with cloud and how they took advantage of this new technology. And said, “Hey, we’re going to streamline the way they, we gather intelligence and telemetry and help for incident response and EDR and all that.” And whatever actually became CrowdStrike, right? I said, “This might be our time. This is our moment every 10 years, right? There’s like a new shift in technology. Gen AI and AI might be the way to do it.” So yeah, so I hopped on and just course corrected and we’ve had some wins along the way. So I don’t know if you want to dive into that, but… Manuel Martinez: Yeah, no, definitely. I mean, it sounds like, again, you’re always looking for that thing that’s kind of, how are you going to feel? And it sounds like, “Hey, this is my moment. Hey, I work well with this person.” And having that connection. So obviously he also had some connection with you, right? Because it’s not you reaching out to him and saying, “Hey, I want to be a part of this.” It’s like, “Hey, let’s kind of go through.” And those different skillsets there, which I’m sure also co
From Geology Research to Cybersecurity Leadership: Aakin Patel | Ep052
Episode Information Show NotesSometimes the best careers are the ones you never planned. Aakin Patel went to school for geology. He spent years studying plate tectonics and doing computational modeling. The plan was academia. But grad school revealed something important. The academic life he imagined wasn’t the reality he wanted. So he pivoted. He took his Unix skills from graduate research and landed a job as a system administrator. Just temporary. Just while he figured out his next move. That temporary job turned into a 20+ year career in technology and cybersecurity. In This Episode: Aakin shares his journey from geology to becoming a cybersecurity consultant who advises governments and organizations on strategic implementation. He talks about working at Brookhaven National Labs, dealing with the unique security challenges of international scientific research, and building cybersecurity programs before the field had its current name. The conversation digs into the skills that matter most: problem-solving, communication, and the ability to bridge technical and business worlds. Aakin explains why being able to “dumb things down” is actually proof you understand something deeply, and why teaching others became crucial to his leadership success. You’ll also hear about the day his boss literally put him on a plane to management training, why he initially hated it, and how that moment changed his career trajectory. Key Takeaways: – Career pivots don’t have to be permanent disasters—they can become opportunities – Problem-solving skills transfer across completely different fields – Being the bridge between technical and business teams is a superpower – Learning to communicate complex ideas simply is a leadership essential – Technical burnout is real, and strategic roles can be the answer – Teaching others tests whether you truly understand something – Your ability to build and lead teams matters more than any single technical skill – Reputation and relationships open more doors than resumes About Aakin Patel: Aakin Patel is a cybersecurity consultant specializing in strategic implementation for governments and organizations. His background includes geology and geophysics research, Unix system administration, and cybersecurity leadership at national laboratories. He’s built security teams from scratch and helped organizations implement security programs at strategic levels. His mixed background gives him a unique ability to translate between technical complexity and business needs. TranscriptionManuel Martinez: Welcome everyone, my name is Manuel Martinez, and this is another episode of Career Downloads, where each episode I basically hit the refresh button and bring on a different guest to learn more about their background and their experiences, to help uncover any actionable advice that you can use as you’re managing your own career. So for today’s episode, I’m very excited. I have with me Aakin Patel, and he is a consultant in the cybersecurity space. We’ve had some conversations about, you know, some of the things he’s done earlier on, how he kind of got into, you know, this field, and just the things that he’s done along the way. So I’m interested to kind of get to know him and how he managed his career a little bit more. And with that, I’ll go ahead and introduce Aakin. I appreciate you coming on, Aakin. Aakin Patel: Thank you, it’s good to be here. Manuel Martinez: So one of the things that I kind of start with all the guests is if you don’t mind telling me just a little bit about where you grew up, and then eventually kind of what led you either into the technology field, some people, you know, they fall into it later on. So maybe you started in a different career field. So again, just kind of a little bit of that background about yourself. Aakin Patel: Oh, yeah, so I grew up in the Northeast US in the New York, New Jersey area. I went to college actually for geology and did graduate work in geophysics. And I did a lot of simulation modeling as a part of that because I was studying plate tectonic processes. And, you know, so I did a lot of computer modeling. I got very skilled at like, you know, like Unix systems and like Linux systems when they started coming out and doing some on the programming side, doing some computer modeling. And at some point, I realized that I didn’t want to go into academia, which is where my degree was leading. And kind of as a stopgap measure at the time, I decided to just go out and get a job as a Unix administrator while I figured out what to do with my life. And that’s kind of how I fell into the Unix side of things and kind of grew into cybersecurity as natural evolution roles from that. Manuel Martinez: And when you went to school to kind of study geology, obviously you didn’t want to go the academia side, but what is it that you originally were kind of that attracted you into that field and thought, oh, I want to do something in this area? Aakin Patel: So I’ve always liked like the earth sciences. Like I find them fascinating. I actually very much thought for a very long time that I do want to be a research scientist. So it was like the realities of grad school and seeing like the in-depth look of how that worked and what my long-term, how my long-term career would play out that I realized it wasn’t the path I wanted to proceed down. It was the way it played out in reality. So like I don’t regret doing it. Like I really liked studying that. And it’s kind of like a great like set of background knowledge to have. But like once I realized it wasn’t for me, like I pivoted to something that I could do. And that worked better for me. Manuel Martinez: Yeah, that’s a good point because a lot of times, I mean, especially when we’re that young, right? Or when we’re starting our career, I’ll say, we think that it’s going to be one where we have this grand idea of how it’s going to be and it doesn’t turn out that way. And understanding it’s okay to kind of pivot. So then you decided, okay, I want to do something in the meantime. And you got into Linux system administration. And obviously you didn’t think like, oh, I’m going to make a career at this, at least not at that point. So what is it that you started doing there and kind of start to build that skill set to say, okay, I’m going to at least for now be a good Linux sysadmin? Aakin Patel: So I had to learn Linux system administration and Unix system administration to do the simulation modeling I was doing in grad school, right? Like I worked on Sun Spark stations and then DEC alpha workstations to do a lot of computer modeling. And the DEC alphas ran Linux and the Suns ran Sun OS and then Solaris. So I became good at Unix just as a part of that. So it was like an easy, I could put that on a resume really easily saying, hey, I’ve done all this stuff and get a job doing that. So that was kind of like an easy transition for me while I was looking to go out and kind of figure out, like a stop, I actually just figured I’d be doing that for a year or two, then refresh and then come back into academia. And I just, after a year or two, I was like, I don’t really want to go back. So I didn’t. Manuel Martinez: Did you think that, okay, maybe I’ll pivot and go somewhere else as opposed to staying as a Linux sysadmin? You’re like, okay, I don’t want to go back into academia. That’s not the area for me. Did you think, okay, let me kind of see what this Linux administration does for me or were you kind of exploring other opportunities? Aakin Patel: I wasn’t really sure I was keeping an eye out, but like my first job, like when I switched out was working just off Wall Street in New York City, working on like bonds trading systems. And while a cool job that paid fairly decently, it involved like a two and a half hour commute each way just because of the traffic around New York City. And I rapidly realized that I was doing like 15 hour days that I didn’t want to be doing. And then I got like a different job and I kind of lucked into a job at Brookhaven National Labs, which is one of the department energy national labs, national labs. And they did a lot of very interesting like research projects and like, it was like a very cool facility to work at. And they hired me interestingly because of my mixed background, right? Like they wanted someone with that academic background who was also skilled in technology because it was like a science and research facility and they kind of needed someone who could bridge the two worlds, like the worlds of the academics and the scientists working there with the technology needs and the technology directors of the IT department there that served those scientists. And that’s kind of how I landed in that role. And that was a cool enough job and a cool enough place that I was actually pretty happy staying there for a long time. Manuel Martinez: And it sounds like it probably kind of met a little bit of, like, hey, I’m doing this Linux administration, which you seem to kind of like, but it also gave you some of that research that while you didn’t want to go into academia, it sounded like initially like, hey, this fascinates me. I want to kind of do a little bit more of that research, but not really be like a full-time academic researcher. Aakin Patel: Yeah Manuel Martinez: And having both of those skillsets and being that bridge, one of the things that you kind of told me is there were areas that you weren’t proficient or knowledgeable enough. And it was kind of, you know, you were thrown into this role. So kind of tell me a little bit more about that. Aakin Patel: Yeah, so when I first started, like in the technology field, it’s very weird. Technology environments are very complex and kind of grow organically most of the time. They’re not very well planned out when they first start. And so if you go into a new technology environment, it almost always takes you like several months, sometimes even like a year to like actually get like a good grasp of the environment, like, you know, really understand it. And a lot of the products they were doing were so critical and so expensive that they didn’t want someone new coming in and just like messing things up, right? They’re like, they don’t want you risking downtime. They don’t want you, you know, messing things up. So they’re like, look, your job to start off with is just to learn the environment, you know, learn how it works. But meanwhile, we have this issue where we deal with very intelligent people, very smart people, like all the scientists, and they have their own way of doing things and they don’t want us to tell them how to do things because we’re not scientists. So what we want you to do is be like the bridge between us. We’ll tell you what you want to get done, and you’re going to go talk to the scientists and sell them on it, and they will listen to you because you have the science background. And I thought they were crazy because I was like a 23-year-old kid at the time, you know, trying to tell these, you know, science, like, well, world renowned scientists in their field, like how to do things. But, like, no, it was actually true. That’s actually why they went and hired me is because of their academic background. And they would send me to go talk to the scientists and I would learn about their research, which was really cool, and I could understand their research because it meshed with my background. And, you know, talking to them a little bit about it and then kind of just be like, hey, so we’re doing this on the IT side of things. At first they’d be like, well, we want to do this. I’m like, well, this is a good idea because of this. And they’ll be like, well, if you say so, Aakin. [laughter] Manuel Martinez: I mean, that had to be a weird sensation, right? Like being that young, you know, again, these accomplished scientists and for them to say, well, if you say it’s okay, then we’re good to go. Aakin Patel: Yeah. Manuel Martinez: Is that because they knew that you had kind of both understanding of the IT side and the academic wasn’t so much like, oh, well, this guy knows it all, but they’re like, oh, he understands our business. Aakin Patel: Our perspective. Yeah, exactly. So these guys, they were very intelligent, right? A lot of times, like, if they wanted to do something on the Linux side, they’d be like, I’m just going to figure out how to do it myself and do it. And they would do it. Like they would get their system set up and they’d work on it and they would work. But that’s not great from an enterprise perspective, right? Like that’s not great from the perspective of a centrally managed organization and like a place where you have hundreds and thousands of projects and everything being its own little enclave, it’s kind of a little bit of a nightmare. So as they went to move more and more to, I guess, more centralized set up and more organized and managed set up, there was a lot of pushback from the scientists because they’re like, well, we’re perfectly capable of running it our way. And who are you to tell us that? But because I was approaching it from also having an academic background and I would like explain it to them in the terms that they wanted to know. And that was really the key, right? Like they wouldn’t accept things blindly. They were like scientists, they would question, they would like, we want to know why. And I understood that. I understood the kind of why that they wanted to know. And I would explain that to them. And that’s kind of why they accepted that, right? If I just came in and said, nope, I’m a scientist too. You’re going to do it this way. They would have been like, piss off. [laughter] Manuel Martinez: And that’s– Aakin Patel: And I think a little bit of the awe that I held for them and that I knew the reputation kind of helped a little bit too. Manuel Martinez: Right. And that’s good because a lot of times– well, in this one, it’s very specific, right? It’s scientists, but that’s no different than just any other business, right? It’s understanding the business. Yeah. I’ve had other guests where we talked about that, like, hey, you can kind of go through and I can tell somebody you’re going to do this. But if they don’t understand what the business benefits are, at least from an executive leadership or people who aren’t in IT, and then being able to translate that the other way as well, right? From the business standpoint, when you’re telling IT folks similar to the scientists and saying, hey, we’re going to do this. But if you explain it, hey, here’s what the business is doing and here’s why kind of like in the technology terms, that’s a big benefit. Aakin Patel: That is probably the most useful takeaway I’ve had throughout my entire career. Because through a series of events and steps, I ended up transitioning to cybersecurity, actually almost before cybersecurity was like a thing. And I grew from there, I grew to executive level management. A big part of my success in that regard is being able to explain to the business why this technology or this approach benefits the business and being able to explain to the technology why they need to approach things in a way that benefits the business. Because both sides have a like, well, no, this is what makes sense to us. So this is what we’re going to do. And that’s like a perspective on the business side and on the technology side. And they don’t always meet. And being able to bridge that is kind of critical to basically go anywhere outside of the front line, hands on technical level or the hands on business person. I’m a strategic consultant right now. Like I advise small governments, sometimes larger governments and larger organizations on how to implement things at a very strategic level. And I would not be able to do that without being able to speak to both sides of the house and like to be able to bridge that gap. And having that full understanding of the needs of both sides is very, very important to being able to do that effectively. Manuel Martinez: So you’re in this role. It sounds like you’ve become pretty successful, right? At least both ways of kind of being that bridge. How long were you there? And what made you decide to– I don’t know if you ended up kind of promoting up within, if you decided to kind of look out– Aakin Patel: How long was I at the DOE? Manuel Martinez: At the– Aakin Patel: National Lab. Manuel Martinez: At the National Labs. Aakin Patel: I was actually there for seven, seven years, eight years? About that. Manuel Martinez: But not doing the same role the whole time? Aakin Patel: I started off in the Unix team. And then I got moved. At some point, they wanted like a full blown dedicated cybersecurity team. They’d started to build one up, and they pulled me into there as their Unix expert. And then I spent most of my time there as a part of that team. And growing with that team, growing with the responsibilities, helping start up like one of our first like pen test programs there, like an internal pen test program doing like log analysis, starting up programs that eventually became things like a SIEM, like a security event monitors. So yeah, so they pulled me into the group that for the cybersecurity side of things, because they needed someone specialized in Unix on that side of things. And that’s how I moved into there. And I kind of grew with that role as that team grew. I stayed a hands-on cybersecurity person, and like an incident investigator and incident responder while I was there. When I– at some point, I left that job because I knew I wanted to leave New York, and I came out here. And then out here, I had a couple of roles with a bunch of different groups for short periods of times, like some with the casinos, with a couple of corporations here, a couple of the federal groups out here, some small businesses for a while. I was doing like some consulting for a little bit, and then one of the people I was consulting with hired me as to lead their technology team because they were starting to– their business started to grow really fast, and they wanted me to help scale it up. So that’s how I ended up on the leadership side of things. And because I was advising them on how to scale it up, and the guys were just like, I need you full time. I can’t have you just doing these few hours here and there. I need you to build this team out for me. What can I do to bring you on? Manuel Martinez: And a lot of just the skills that you’re gaining– again, this is before cybersecurity was cybersecurity. It’s still security, but you’re building the skill set, working a couple– quite a few years there in that role. And while you mentioned you built your own SIEM, and before it was really a thing, and what is it that started that security practice? Aakin Patel: Oh. So at the National Labs, it was a very interesting environment. Like the National Labs are very science focused, right? And they have a lot of very cool and high end projects, including particle accelerators. And particle accelerators are very, very interesting in that they’re built to a specific size. They are built to like a physical size, which affects which atom they can spin around at near light speed and smash to get their high energy particle experiments and do the studies on. And these high energy physicists want to study what those effects are, but they want to study it more than just one– like more than just one atom type, right? So at Brookhaven National Labs, they had a particle accelerator. They had multiple particle accelerators, but their big one was one that smashed gold atoms. And it was 2 and 1/2 miles in diameter. That’s how big it had to be in order to spin gold atoms at the speed of light and smash them together. Those are not– that’s not a trivial project to build. And it’s on the orders of hundreds of millions to billions of dollars across– and they need particle accelerators like this for all sorts of different atoms. There is a– I forget which the actual specific organization is, but there’s a consortium of scientists across the world that kind of help plan these out. And they kind of– once a particle accelerator exists, when someone else has got the funding to build another one, they kind of build them at a different size to be able to smash a different atom. And there’s like an international agreement between all the countries to allow scientists to go from accelerator to accelerator to accelerator to do their researches, to do their research. And as a result, there are lots of scientists from all kinds of countries going to all these accelerators, including at our national labs. And we have a lot of very sensitive projects going on in our national labs, and the other countries do their projects as well. So they do their accelerators as well. But also, just because we have this treaty and this agreement does not mean that our respective intelligence departments are not very interested in each other’s experiments, right? So when we would get scientists come in, the scientists might genuinely just be there to do their research. But that doesn’t mean that all their equipment had not been affected by their various intelligence and counterintelligence teams, but they weren’t bringing Trojan software into the environments knowingly or unknowingly. I actually honestly suspect that almost all of them were unknowingly, but it was like a real threat that we had to deal with. There was a lot of very malicious technical activity going on in the network environment just because of the nature of things. And that’s kind of why the cybersecurity teams were stood up, because they needed dedicated people to deal with that and to look for that and detect that and become familiar with how to detect that. That’s before any of these network intrusion softwares were around, before any of these tools to detect the stuff automatically on the network existed, this was like a manual thing that we all did. That and it wasn’t really common enough for these tools to exist. So it was something that every organization that needed something like this, which were the National Labs, for example, would do on their own. And that’s kind of how I got into that role and how those teams got stood up. Manuel Martinez: Because again, it’s newer, right? It’s not like you can buy off the shelf. You can buy off the shelf software or something that’s kind of tailored. You’re learning a lot of this, I’m assuming kind of through trial and error and just figuring this stuff out. Aakin Patel: There weren’t any guidelines for it. They were just like, we need to do this. I’m like, all right, I guess I’m going to figure it out. Manuel Martinez: And I mean, did you find that part exciting? Was it something like going through and saying, OK, I’ve got to figure this out? There’s nobody to rely on. Like, hey, I can’t go ask the person, somebody else, and say, hey, how are you doing this? Because they’re going to be like, that’s not something that we deal with. Aakin Patel: That was very much the case. Also, this was early enough that a lot of social media didn’t exist. There weren’t social media groups. The closest we had was Usenet at the time. I don’t know if you’re familiar with Usenet. You are. OK, yeah. So we had Usenet, but you weren’t going to be talking about classified level problems on Usenet, right? And there wasn’t other places to go to. There was no big collectives. There weren’t large conferences being– things were just starting to come into existence. So a lot of times, we were on our own, or we’d reach out to other national labs, and be like, how are you doing that? And they’re like, how are you doing that? We want to know. Manuel Martinez: Right. And I’m sure, because there’s some of that knowledge sharing, but at the same time, they’re like, well, we don’t know. How are you figuring this out? Aakin Patel: And research institutions have always kind of been– their funding goes towards research. The IT side was always seen as overhead. And so there wasn’t a huge amount of staff there for that. We were a cybersecurity team at our peak while I was there. I think we were six people at our largest for over 15,000 people that were at that facility. And of those 15,000, maybe 8,000 or 9,000 were foreign nationals. Right? So and of those six people, I was the Unix guy. Right. We had a Windows guy. We had a networking person. And we had one pro– someone was a dedicated programming person. And then people focused on the administrative side. Manuel Martinez: It’s not like there’s a group of you. Like, oh, hey, let me bounce it off the other Linux person that’s here. Maybe it’s the Windows person, but they’re different. But just kind of talking through ideas. That’s interesting. So having developed that, and like you said, you wanted to kind of move out of New York, but then also that had to give you– especially starting out, like you’ve started off as just kind of like a communicator. You’re like, OK, I’ve got the communication skills. Now I’m building the technical skills and the problem solving. Is that part of what also gave you the confidence to say, hey, I want to move out of New York, and I know that I can– if I don’t have the skills, I can build the skills to kind of move out into a different role? Aakin Patel: I think so. Probably, right? Like, I’ve always– I always prided myself on the ability to learn what I needed to learn. I think it’s what made me a good scientist. It’s definitely what made me a good person in technology, especially starting out when every technology shop was like build it yourself. You know, you do it in-house. If you can’t do it in-house, why are we even hiring you? Right? Like, that was a lot of the attitude back then. Like, and I know that has changed. Like, nowadays, places are very vendor and product focused. But like, that was not the case for a very long time. It was very much, you’re the guy doing this, so it is your responsibility to get it done, and you’re going to have to figure out how and make it happen. Manuel Martinez: So then when you moved out from New York and you moved into Vegas, did you still kind of find a similar, like– now you’re thinking, oh, I want to get into, like, a security type role? Did you go straight into consulting? Like, what is it that you decided you were looking to pursue now that you have, you know, a couple of years of experience in the tech field and say, OK, I think I want to do X, or– Aakin Patel: At the time, I was– I think by that point, I was pretty firmly cemented in the cybersecurity role. I did like a lot of the assessments and analysis side of things. I got a role pretty quickly with one of the casinos here, helping with their– on their technical audit. Like, I was their internal technical auditor, and that was a lot of fun and very enjoyable. But yeah, I think, like, since then, I’ve kind of focused on cybersecurity-related roles, and they were in different capacities in the cybersecurity field, but they’ve all been cybersecurity focused since then. Manuel Martinez: And it was just kind of the– was it more the problem solving of cybersecurity? Was it more the defense, you know, the kind of finding holes? Like, what is it that really kind of made you think that, yeah, I like this area? Aakin Patel: It was a little bit of all of it. OK. But also, like, my perspective of cybersecurity is that, like, you know, from my background, I became really good at the Unix side of things, and then I moved into cybersecurity for Unix systems because I had the skills and the knowledge to be able to look at systems and be like, these are where the holes are. This is how we fix it. This is how we approach the problem in a better way. I like the idea of approaching the problems in a better way. I like– a lot of my roles since I moved out here were not cybersecurity, just like it was a pure cybersecurity thing, but like cybersecurity as, like, an advisory to the technology department as a whole, like getting involved in every project, helping architect all the new projects that are going in, helping design them to be better from the ground up. And like, that is interesting to me, right? Like, being able to, like, understand the full scope of what’s needed for a project, saying, this is how– this is the initial plan to build it up, but like, if we do it in this way, it’ll be better. It’ll be more effective. It’ll serve the business better. It’ll be more secure. Being able to put all those pieces together and, like, optimize it and strengthen it is very interesting to me. Like, there is that solving the puzzle option. There is that gaining a better understanding, seeing how everything works, seeing how all the data flows together, and making it function in, like, the best way it can is kind of where the real appeal of the field is to me. Manuel Martinez: So then you’ve– sounds like you’re doing a bit of a consulting, and you kind of touched on it earlier, as they were tired of you kind of just doing it on the side and said, hey, we want you to kind of do this full time. In that capacity, are you– when they ask you through that, are you kind of interviewing it? Are you interviewing for that role? Or is it more you’ve kind of established yourself, your knowledge, your credibility, and it’s more like, hey, we want to kind of– Aakin Patel: In that particular case, the CEO of the company just approached me and said, I want you to do this. And I initially turned it down a couple of times. And then the number got really good. And so I was like, all right. Aakin Patel: And that’s, I think, because he’d seen– they approached me to help solve a problem they were having with their operations. And he really liked my approach to solving the problem. And then I helped them solve more problems. And he was like, I like the way this guy approaches problems, the way this guy solves problems. And he saw the direct impact on his business and that let him do a project turnaround that would take his guys normally– his guys would normally take three to four days working like 12-hour shifts to go from one project to another to switch their systems over to being able to just run like an automation script and be done and be good to go. He saw the direct financial impact to his business. So it made sense for him to be like, I want to scale my business. And I need someone with that skill set to help me scale correctly. Manuel Martinez: And when you mentioned you turned it down a couple of times, was it originally because of the financial? Were you not so interested in the type of role? Because there’s a lot of times where I’ve heard from different people where they’ll be approached like that, like, hey, we want you to apply. Or even if you apply and you get the role, it’s the negotiating tactic. And maybe it wasn’t a tactic, but understanding like, OK, was the role not interesting enough? Or was it like, hey, for what you’re asking me to do financially, this doesn’t make sense. Aakin Patel: There’s a combination of a couple of things. One, like, having done the few things that I’d done there, I knew that the scope of work was huge and that there was a lot involved. And I didn’t want to commit to all of that initially, not for the funds he was offering. And two, one of the most interesting things about the national labs is the sheer variety of projects that go on there. Like, there’s everything from chemistry projects to medical to biology, laser science, magnetics, high energy physics, everything. You’re not going to get bored because there’s so much stuff going on. I didn’t want to just commit to one business’s problems at the time because it’s kind of limiting the scope of work and limiting the scope of interest. And I wasn’t super excited about that. But when he said– he was like, the number got good. And he was like, I’ll give you full reign to start up an IT department, run it however you want. You got full authority to do everything, build it up from the ground up. That’s pretty interesting to me. And so the project became a lot more interesting. And the conversation became appropriate. And I was like, all right, I’m down. Manuel Martinez: So then now building a team in an operation that’s something that many people don’t get to experience. So I’m curious what we’re– there’s good from that, right? Because you get to do it your way. But there’s also challenges and things that you’re like, man, this isn’t going how I planned. So I’m just curious, what were some of– Aakin Patel: The biggest challenge– I think the biggest– this all have been true in every single case where I’ve had to build a team from the ground up, which is more than once is financial. Once a business starts tallying the cost of what’s actually involved hiring skilled IT people, and technology projects can get pricey. And there’s a payoff, but the payoff could be a couple years down the line. And for a business looking at that, they’re like, we could just keep on chugging along the way we’ve been chugging along instead of making this huge outlay up front for a payoff three years down the line. That’s not– that’s a hard case to sell. And that’s– once I realized at that level that this is what– like my work was, it was kind of enlightening. And I had to actually pivot a lot. And I had to learn a lot. I was used to being a hands-on guy, and making all the solutions, right? And I feel that this is a challenge that every single person who goes into management or leadership from a technology role encounters and has a very hard time, almost always you get promoted into those roles because you are very good at what you were doing. And what you were doing was being hands-on problem solver. And then you get promoted to management or leadership. And your job is to no longer be the hands-on problem solver. And it’s hard for you to let go of that internal identity, right? Like, your identity is being the problem solver. That’s what you’re good at. And your job is now no longer to problem solve. It’s to make it so other people can problem solve easier. And that’s a very different set of skills and a very different shift in mentality. And I’m sure I messed up a few things until I actually got the hang of that. But one of the things I realized pretty quickly is that, like, you pointed this out earlier. Like, I’ve always been in roles where I have to learn a new technology, learn a new thing, learn a new skill set fast. I realized that my skill set was no longer learning about technology. The things I needed to learn was learn how to deal with people and work with people better, and learn how to deal with organizations and work organizations better in a way that they function better. And the optimization I had to do was not at the technological level, but at the organizational level. Manuel Martinez: Understanding that you had to learn that, is that something that originally you probably kind of fought against a little bit? And the reason I ask is I was in that role, right? Well, I was that hands on. I became a manager where I was still hands on. Like, I was more of a, it was a small team, and I was still a lot more hands on. But once they kind of started asking me to, you know, hey, we need you to be more of, like you said, more of the facilitator, help them solve problems. You need to kind of interface more with the business. I fought against that, right? Like, I didn’t mind learning how to communicate with people, but at some point, I was, you know, there was that internal struggle. And I ended up going back to, you know, actually move to a different role and said, you know what, this is not for me. Turns out it just wasn’t for me at that time. Like, I was still probably too young or I just, I wasn’t done doing a lot of the kind of hands on work. And I went that way, but it sounds like you kind of embraced it. So I’m just curious, is that something? Aakin Patel: So I don’t think I initially embraced it, right? Like, I started, I was still doing a lot of hands on stuff. And I think the CEO saw it pretty quickly. And he had a lot of issues. There were problems working for him. But in many ways, he made the right calls a lot of the times. That’s why he was a successful businessman. When he saw that issue, he showed up one day and he was like, here, like he handed me and they were like two plane tickets. And I’m like, what is this? He’s like, you’re going to Georgia tomorrow. I signed you up for a management class. I’m like, I’m not going to Georgia tomorrow. He’s like, oh, yes, you are. You know. And like, he realized the issue was that I was still trying to do projects. And he was like, I don’t want you doing that. That’s not your job. You have these people do that job and you need to hire more people do that job. I need you to run the department. And he like thrusts me like hard into management training. And like, on the plane right there, I thought about that for a second. I was kind of pissed, but I was like doing it like this is what my boss wants. You know, I got to do it. But on the plane ride there, like I thought about it for a little bit. I was like, no, he’s right. That’s actually my job. My job is different. It’s not what I thought. You know, I don’t know if I would accept it knowing that. But this is actually my job now. And I can like quit or I can actually do a good job at this job. And so I went through the class and with that perspective. And from that perspective, it was actually pretty interesting learning about it. Because I made a point of thinking about it as I would about computer systems and just trying to draw all the correlations. And then it made sense in my brain. And… so it actually ended up being a pretty interesting class because I was able to relate it to my experience and thinking back about– like, I don’t think I consciously processes at the time. But it kind of meshed with my role at Brookham and where I was like the intermediary. I wasn’t working on technical projects to start off. I was working on making the technical project easier to happen, making it easier for the technical team to do their projects by being the intermediary between them and the scientists. And I was like, that’s kind of my role now, is to be the intermediary between the tech team and the rest of the organization. And from that perspective, it became a much more fun and challenging project, a much more fun and challenging and interesting job to do. And I spent a lot of time– like, I went to a bunch of classes. But I got a lot more value out of a lot of books on management. And some of them were like absolute garbage. And some of them were very full of like trite sayings that made me grow and roll my eyes. But most of them had a couple of kernels of wisdom in them. And I would just take that and ignore the rest and go from there. And I think I realized fairly quickly that everyone has their own management style. And I thought back to the managers I really liked and the managers I really hated. I made like a be like this, don’t be like this list. And I just tried to focus on that. And the people I hired, I paid attention to them when they would say– so I’m going to say something that’s not like super kosher, but is actually true. The tech field gets a lot of very interesting personalities. A lot of them are very fixated, a lot of very single-minded, very focused. And not all of them have the best social skills. This can be a detriment or it can be an advantage. Right? Some of them will straight up tell you how it is and not in a nice way. But they are being utterly honest. And you have to embrace they’re being honest. And look at their feedback and be like, what part of this feedback is useful? What part of it is garbage? I had people like that. I had people just be like, no, that’s stupid. And this and this and this. Right? And looking at that, no, the stupid comment is not actually helpful. But some of the things they were saying were dead on. And that’s what I needed to focus on. Right? Because my job was really to let them work better. And what they were telling me was what I was doing was not letting them work better. Manuel Martinez: And you mentioned that you kind of fought it a little bit and you’re pissed originally when they hand you the ticket. And it sounds like he knew wanting to hire you and then also kind of buying those tickets and forcing you to go into this management. Sounds like he probably saw something in you and says, hey, he can do this. Now, the approach, most people would be like, wow, that was the wrong approach to kind of take. Right? He could have talked to you or whatnot. But do you think that in that moment and then at that point in your career, that’s the approach that you needed? Or would you have been open to it if he would have sat you down and said, hey, I think we should look at getting you into management classes and talked through it as opposed to saying, you’re going on a plane and you’re going tomorrow? Because again, different times, different situations. I know that there’s times where I would need that type of, no, you’re going. And not have the time to think about it. And there’s other times where, wait a minute, no, I need that week or let’s have a couple conversations about it. Aakin Patel: I would like to think that if he’d approached me with a normal conversation, I would have accepted and paid attention. But I don’t know. Manuel Martinez: Yeah, I mean, it’s just one of those things. Aakin Patel: I do know that he saw that I was able to get his team to work better than he had been able to get his team to work, so he appreciated that. And I do know that a large part of that was because when he talked to me about that problem, I was like, you just don’t know how to talk to technical people. I know how to talk to technical people. Let me go talk to them. And that wasn’t wrong. I went there and I told them, and I was like, hey, this is what we need to do. This is why. This is why it makes sense to do that thing, even though it may not be the most optimal technical approach. And they were like, all right, fine. Manuel Martinez: You said it, right? A lot of times it’s just that people want to know from both sides. If you force somebody to do something, they don’t want to. But if you explain to them why, and even though– help them understand, well, why would we do this if it’s not, again, the optimal way? But again, they just want that understanding. Oh, oh, I get now why we have to do it, even though you and I both know that’s not the best way to do it. But for this situation, we do, and here’s why. Aakin Patel: Yeah. Manuel Martinez: OK. So you’ve built this team up, and it sounds like you’ve– are slowly learning what your management style is. You’re getting good at– and I like that approach of using that technical approach of kind of filtering, just doing everything else that you’ve done from a technical standpoint. And what is it that now– again, we don’t have to go through every role that you’ve ever been in, but now, what’s that next step? Because you mentioned you were in leadership. You spent building up a bunch of different teams. Is that kind of what you thought? OK, I’ve built this skill set. It’s obviously a good skill set to have, and being able to kind of talk business, talk technical, build teams. And did you think to yourself, this is what I kind of– at least for now, this is what I want to do. I want to be that person that comes in and either builds a team or restructures them. Aakin Patel: I definitely– yeah, absolutely. That is the thought I had, and that is the thought I still have. And it’s like the thought that kind of drives a lot of what I do. I do love doing that sort of stuff. It’s very rewarding. It’s kind of cool to see a project in an organization go from very small or minimal or nonexistent to a fully functional, well-optimized, well-functioning team. I’ve really liked doing that in the past. I’m kind of doing that right now sort of in a different capacity, because I’m focused on starting up my own business, but I would like to grow to the point where I have a team working under me, working well on the consulting side and on that side. And I would love to actually be able to build up a team to do that sort of work and focus on running the team versus being the consultant myself. Manuel Martinez: And what is it that you end up liking about that? Because I’ll tell you, I mentioned management earlier in my career, and I was like, nope, that’s not for me. And it wasn’t until later on– I can’t remember if it was an event or a person, but at some point, I started to switch. And it probably– actually, I think about it, it might be around the time that I started teaching. So I would teach part-time. And that’s where I started to kind of develop more of the understanding and more of a passion of like, oh, I like doing more of the leadership type stuff. I was OK being hands-off, because now I realize that it was more impactful and I could have a greater reach. Instead of me doing it by myself, if I can work with a team of three, four, or five people and help them be successful, there’s a lot more– it scales a lot better, and there’s more impact, as opposed to just me trying to do it all by myself. Aakin Patel: The impact is a big part of it. There’s a few other factors. One is, like, I mentioned that I like being involved with a lot of different projects, right? I like the variety. And that is, frankly, easier to achieve at the strategic level than the tactical level. If you’re hands-on, you’re a tactical person. When you’re in a more advisory capacity, you’re being more strategic, you’re involved in a lot more things. And that is super interesting to me. I like seeing how all the projects interact together to make the organization function as a whole. And to be perfectly honest, a decent chunk of it was also burnout. Like, I had a lot of technical burnout, and I don’t think I’ve realized it for a long time. But being able to shift into leadership roles, being able to guide other people, use my knowledge, especially when I had people who were new to the field, I could be like, you know, like, teach them, you know, like, teach them, guide them, mentor them, as well as, you know, help them grow their skill set without actually doing the hands-on technical work myself, kind of let me feel like I was pulling on all my knowledge, drawing on all my knowledge, and not doing the things that led to burnout. Because at some point, like, I think a lot of people just hit that point, and I had hit that point, and I don’t think I even realized that I had hit that point. Manuel Martinez: And when you say the burnout, it was the burnout of just being tired of doing the day-to-day work, or it was just like, you know, just overwhelming, just, I know what you’re talking about, where I don’t know that I’ve experienced burnout, but maybe there’s that moment in time where you’re just like, I’m tired of doing this, right? And maybe I took it as more of a, like, I’m tired, and maybe it is more burnout. And once I started to kind of teach and get into more of those, you know, even if I wasn’t like a manager, but like more leadership roles where I was like, hey, I was the lead engineer, the lead architect, like, getting into those, and you’re helping other people, that energized me, and I was like, this is what I want to do. Aakin Patel: I think it’s, yeah, like, I think you kind of nailed it, right? It was a lot of getting tired of doing that day-to-day stuff, like, and like, a lot of those hands-on things, like, even like the things that used to be exciting, like when I used to go do incident response, like, we’d detect malicious activity, I’d go, I’d grab the box, we’d do forensics on it, and I’d write them on ports, and like, that was super exciting to me to be able to do that. When I worked with counterintelligence groups to do a lot of work there, like, it used to be super exciting, and then after a while, it just became a grind, and I was tired of that grind. Manuel Martinez: Now you’re doing a lot of this, and you mentioned you started to kind of have contracts, and what is it that kind of led you into eventually kind of starting your own consultancy? Is it because you’re moving on to projects? Did you go from, like, okay, I don’t want to be hired on, I want to do more project role to kind of fill that need of, I want to do different things? Aakin Patel: After I left that company, I got hired on, I started looking for, like, government-specific work, because I really liked the time I had at the National Labs. Like, I liked, I wanted that level of variety, right? Like, I didn’t want, like, that small focus of that, that one small business. I wanted that large variety, and, like, the National Labs had that variety because they functioned like a small city, so I looked for other groups that functioned like a small city. So I started applying to a lot of the local government jobs out here, and I landed a role at the airport, and the airport is absolutely a small city, right? I landed, like, the cybersecurity role there, and that was, again, it was like a build-up the cybersecurity team, which I was super excited by, and the airport has got so many projects. And so that kind of led to a little bit of everything that I wanted, right? Like, I got to build up a team, I got to work on a very large variety of projects, I got to work in, like, the environment I kind of enjoyed, like, back in the government space, and that was kind of how I ended up. So, yeah, I was there for a long time. I was at the airport for seven years, and then I built up that team. We had, like, a good, strong team. We were pretty functional, we were well integrated in the environment by that point. When I started, they looked at me, and they wanted, they made it very clear that they wanted me to start up the team, right? They were like, “We don’t really, we know we need this, we don’t really know how,” and I spent the first two months building up a plan, and then the next six years enacting that plan. But at one point, it became time for me to leave the airport, and I ended up going to the state, and I was the head of the Office of Cyber Defense Coordination there, and that was really cool, because it was coordinating cybersecurity across all the local governments within the state of Nevada. So I got to work with all the cities and all the counties and all the large governmental organizations and non-governmental organizations, some of the utilities, and, like, everything that was going on in the state, I got to be involved in, that was super cool. Manuel Martinez: Being in these types of roles, especially, like, with such a large environment, you’re doing a lot of data gathering, right? Because you’re understanding what they’re doing to kind of help put together, but also, how do you approach having to build a vision of kind of what this looks like moving forward? Because a lot of what you’re doing, it sounds like, you know, yes, I have to understand, I want the variety of projects, you’re getting all this information, but also, at that level, you’re the person, right? Or you’re within the small group of people that are putting together the plan for how we’re going to move forward. So what’s that process like of saying, “Okay, here’s how we’re going to put a plan together when there’s nothing”? Aakin Patel: So for me, the way I approach it is I try to– I will initially start deep diving in, get like a very– as comprehensive a picture as I can about what the current state is. I look at the current state and I’ll be like, “If I was building this up, what would I do differently?” Try to, like– and then be like, “What do I think would be the ideal end state, combine that with what I would do differently, kind of make like where we want to be page, where we are page, and then just roadmap to, you know, like build up that map.” Be like, start doing little– figure out these are the key steps to get there and like what little project can we do that’s opposable to get there? What’s– what can we do immediately? What do we have to do as a priority? What can we put off further down the line? Manuel Martinez: And earlier on in your career, right, you became– you were that sole person, right? So you had to come up with the idea or you had to go through. But now, you know, with– I wouldn’t even say social media, but just with teams growing, with IT becoming a little bit– a lot more prevalent, are you also leveraging other people to figure out what that future state is? Are you researching on your own? Like, just curious, you know, I understand how you get through the assessment of like, “Hey, this is the current state.” But as far as a future state, like what goes into saying, “This is where we want to get to,” and is it just experience? Aakin Patel: A lot of it is experience. I will build up what I think would be good based on my experience, and then I will throw it out there. I’ll talk to everyone who’s like a stakeholder in that, be like, “This is what I think,” and I will let them tear it apart. And they will. They will always tear it apart. And when they’re tearing it apart, you got to sit there and listen. Because sometimes they’re tearing it apart just because it wasn’t their plan. And sometimes they’re tearing it apart because it’s a colossally bad idea. Right? And like, there’s elements of both in like everything. If you want to put out a plan there, you are not the subject matter expert. You got to remember that. Like, you’re not the guy that runs these systems day to day. They will be like, “This can’t happen because of this.” Right? You need to put that into the plan. You have this like, “If this is a stopping block, you got to work around that stopping block and find like an alternative.” In the audit industry, there’s a term compensating control. It’s when you have a change that you know is– when you have a setup that you know is not good, but you can’t change it for whatever reason. So you have some other plan in place to accommodate for that problem existing. The difference between the vision you create and the final vision will always be what sort of compensating controls can you put into place to address all the stopping blocks that everyone can see. Because people are very good at seeing stopping blocks. Right? You throw a plan out there, people will be like, “Oh, no, we can’t do that because of this.” Immediately. That’s cool. You want to know all the stopping blocks because you don’t know the stopping blocks. Let them throw out all the stopping blocks and then work for a plan around them. And then keep on doing that until they say, “All right, I think we can make that work.” Manuel Martinez: And you make a good point there because you will get those stopping blocks a lot easier than you’ll get the solutions. Everybody’s quick to say, “No, no, no, and here’s why.” But understanding, okay, going back to what you said earlier about filtering, “Okay, I’ve got to filter.” Is this really a stopping block or is this just– They’re saying this because they’re trying to stop this because again, it’s not their idea or maybe they just don’t like it. It’s supposed to, “Oh, it’s really something that won’t work.” Aakin Patel: When there’s a stopping block, find the root cause. Okay. And the root cause isn’t always what you’re told it is. Manuel Martinez: Got it. So, now you’ve gone through and you’re doing all this and what other area of… What other skill set are you picking up along the way? So, again, you are a data gatherer, you’re a visionary. So, now you’re getting back into the public sector, you’re going from the airport now over to the state and working with these larger entities. So, the problems, they’re not getting smaller. They’re getting bigger. Aakin Patel: And now politics is in the way. And at this level, almost all your problems are political. A lot of people acknowledge that’s what we should do, but we can’t do it because of this. And this will be some political cause. It’ll be, “I can’t spend money on that because this is… If I don’t spend money on this instead, I’m not going to get reelected.” You know, or… Manuel Martinez: These funds have been allocated for something. Aakin Patel: These funds have been allocated. We can’t make new funds. It is not a part of the campaign message, so we’re not going to waste time on it. All kinds of things. When you get to a very local level, it’s even like other issues. There’s times where it’s like, “We cannot do business with this group because of this thing that happened 15 years ago.” You know, there’s a lot of stuff like that. And, like, grudges get held on. Especially at the political level. There’s… And that… Building up that list of relations and that, like, knowledge of what’s what is kind of where a lot of the data gathering happens now. Right? I’ve been in this field long enough that a lot of the technical data gathering is almost instinctual at this point, but learning about the political challenges and how to navigate that is kind of where my focus is these days and, like, learning how to… Learning what needs to be done and how. Right? Because it’s not always, “This is the plan. This is the right answer.” I’ve put out solutions where people are like, “That’s absolutely the right answer and we can’t do it.” And if we need to do it, we’re going to have to do it like this long, super circuitous way, circuitous way, and it’ll be three years down the line, but we’ll get there. And, like, that’s kind of where I’m at these days. Manuel Martinez: So what is it that ultimately leads you to say, “Okay, I’m going to kind of start my own business. I want to do the consulting and kind of, you know, do things the way that I want to”? Aakin Patel: Part of it is that after I left the state, I saw a need for a thing that needs to exist. That politically can’t. And I want to create it. I’m kind of driven for it. It’s something I tried to do when I was with the state. And it just was not feasible to do just because of the reality of how things have to operate. Right? It’s not even that people are opposed to it. I think most people agree that it was a good idea. But it just wasn’t feasible to do, and I kind of want to do it. And that’s kind of how I’m going about it now. That’s one of the core projects of my consulting group. And then I’m taking on a lot of other business to fund things while I get that up and get that running, get the buy in for that, because that’s one of those super long-term things that will take a while to get going. Manuel Martinez: So it sounds like it’s more of a continuous– and I see a theme throughout this whole thing is, you are really a problem solver. And it sounds like, okay, you came up to a certain point and you’re like, “I can’t do this internally. There’s a roadblock. How do I do this? Oh, if I consult–” Again, it’s not going to be instant. It’s not like, “I’m a consultant now. We can make it happen.” But it’s kind of, okay, I have the ability to make positive change, a positive influence, but I have to do it this way, even though it’s still going to take, again, that’s still two to three years. Aakin Patel: It was made very clear to me that doing it internally was not an option. And I need to stop with that, so. Manuel Martinez: So now up to this point, I mean, we’ve covered a lot within your career. Is there anything that I haven’t asked you or any part of your career that maybe we kind of skipped over that you think, like, “Hey, this is a good lesson,” or kind of looking back over my career, something that I wish I would have known or a challenge that, you kind of overcame. Aakin Patel: I’ll let it ponder, and I might come up with something, but… Manuel Martinez: Okay. So then I guess the other thing is what… I’ve asked you a lot of questions. Is there anything that you kind of want to touch on? You just think, “Hey, this is important. I want to kind of just summarize my career. I want to talk about this thing that… Maybe a little bit more about what you’re working on. I want to kind of give you the opportunity.” Aakin Patel: So I will say this, actually, because I serve on a lot of advisory panels for some of the colleges here, and I’ve mentored a bunch of students and a lot of people looking to get into cybersecurity. And there’s a lot of people looking to get into cybersecurity these days. Get your toehold in however you can. But the real secret to advancing in this field and advancing well is you have to become a subject matter expert at something. Like, cybersecurity is realistically an advanced career choice. And people are getting into it from the beginning right now because we’re at a time when there’s a lot of empty roles and not the skill set needed for those empty roles. But in order to be effective at cybersecurity, in order to see the holes in a system and know how to fix them, you have to understand that system really, really well. You can’t see the holes without knowing what should be there and what isn’t there. And that’s true no matter what part of cybersecurity and whether you’re in policy or you’re in networking or you’re in Windows systems, Unix systems, you’re in IoT, you’re in pen testing, whatever you do, you need to become an absolute expert in that field in order to advance further. Because the higher up you go in the career ladder, the more you’re expected to have a very broad and very crystal clear vision of what the field is and what you want it to be. And you can’t do that if your idea of the fundamentals just isn’t there. Manuel Martinez: And you bring up a good point is there’s a lot of these entry-level cybersecurity roles that are vacant. And I’ve had people that go through it like, I’m having a hard time. They’re asking for so much. And the reason is– and I didn’t kind of put two and two together until as you’re speaking through it– those are like cybersecurity roles are a little bit more– they’re higher level in the fact that you have to have a base knowledge of something. And I think that’s true in probably any area. Even if you’re not going to go into cybersecurity, if you want to try and progress up, you have to find something that you become very proficient at. If you’re not the expert, you’re very good. So that you can be able to talk about that. And then the other thing is be able to talk to others. So for example, I was primarily in infrastructure. So servers, storage, that was kind of my wheelhouse. Now, I dabbled a little bit in networking and things of that nature. Can I configure a router for you? Can I go through and set up a network for an enterprise? No. But I know enough about my field to be able to talk to the netw
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