Episodes

Most entrepreneurs track every dollar in and out. Very few stop to ask what the money is actually for. Hunter Terpenny grew up on 40 acres in rural Virginia, watching his dad quietly save for years to pay for college, in a household where you earned what you got and nobody handed you anything. 2008 wiped it out almost overnight. That moment stuck with him and shaped the path that followed, including walking away from a funded startup and spending three years living out of his truck with a climbi...

Most entrepreneurs are good at making money. Far fewer are good at keeping it, or knowing what it's actually for. Keith Roberts spent 24 years building Zen Man, a creative agency that grew into a machine that nearly broke him. He traded his time for money, weathered lawsuits, hid foreclosure notices from his employees, and hit rock bottom before finding his way out. In this conversation, Keith shares the full arc from starving artist to agency founder to author and speaker, and the lessons that ...

Many entrepreneurs achieve success only to realize they are further away from freedom than when they started. Niraj Shah has spent his career building businesses and working closely with entrepreneurs navigating success. Over time, he began to see a common pattern: the pursuit of achievement can quietly pull people away from the life they hoped success would create. In this conversation, Niraj shares how early lessons shaped his thinking about ownership, entrepreneurship, and building wealth tha...

Chris Girbés has built a life rooted in intention, family, and meaningful work, yet his journey with money has been anything but simple. In this episode, Chris and I reflect on how success and fulfillment are shaped not just by what we build, but by how we relate to it. We explore why financial growth does not create a sense of enough and how old money stories continue to drive high performers. Chris also shares what it looks like to redefine wealth around values, family, and lived experience. W...

Step inside The Inner Circle, where Kevin Dahlstrom and I speak freely and honestly without judgment, challenging each other in pursuit of truth. A single question frames this conversation: What’s the most painful truth you’ve had to accept about yourself? Drawing from different stages of life, Kevin and I share the kinds of realizations that only come with time and self examination. The discussion is honest and raw, with their perspectives converging around growth and self awareness. We explore...

Jon Bowerman built and sold a multimillion-dollar agency before realizing that success on paper doesn’t guarantee fulfillment. His story is about rediscovering the artist within and finding that true wealth comes from alignment, not accumulation. Jon shares how growing up with scarcity shaped his drive for success and what it took to walk away from security for a life of greater authenticity and purpose. He reveals how embracing vulnerability helped him reconnect with creativity, joy, and meanin...

Nathan Barry built ConvertKit (now Kit) into a nine-figure company helping creators earn a living online. His journey reveals how early experiences with money can ignite ambition and how the pursuit of mastery can evolve into a deeper sense of purpose. In this conversation, Nathan shares how a childhood moment of scarcity became the spark for a lifelong pursuit of understanding wealth. He reflects on what it means to treat making money as a skill, and how his definition of wealth has evolved fro...

Step inside The Inner Circle, where Kevin Dahlstrom and Mike Brown speak freely and honestly without judgment, challenging each other in pursuit of truth. In this first episode, we unpack one of Mike's most controversial statements: “I wish upon everyone a failure that brings you to your knees.” We’re not talking about pain for pain’s sake, but about what failure can teach us that success never will. We cover: • Why the wins don’t teach you nearly as much as the losses • The identity trap we fal...

At age eleven, Artur Meyster watched his mom pay with food stamps in a New York grocery store. That moment lit a fire that carried him from Wall Street to leading one of tech’s fastest growing education startups. In this episode, Artur shares the truth behind building and leaving Career Karma. What began as an escape from corporate life became a mission to free others, but after the exit came something deeper. We unpack: • How growing up with scarcity shaped his relationship with ambition • Why ...

Nick Eubanks was living the dream. He had built and sold multiple companies, scaled an unsexy business to eight figures, and exited two ventures in the same year. On the outside, it looked like he had it all. Behind the scenes, everything was falling apart. In this conversation, Nick shares what it felt like to reach the peak and realize he didn’t like the view. Beneath the money and momentum was a growing sense of emptiness. What followed was a full collapse. Then he chose to rebuild his life. ...

Aaron Houghton built and sold a tech company for $169 million before his 30th birthday. At its peak, his business was generating $50 million in recurring revenue and employing over 350 people. But behind the scenes, he was unraveling. Chronic stress and panic attacks revealed a hard truth he could no longer outrun. The version of success he was chasing was costing him his health and his peace. In this conversation, Aaron opens up about the hidden toll of hypergrowth and the internal reckoning th...

We’ve been taught to chase success, but what if real wealth has nothing to do with money? Recorded live at the BaseCamp Boulder event, this conversation with Kevin Dahlstrom and Pete Adeney (Mr. Money Mustache) dives into what it truly means to live rich right now. We talk about freedom, purpose, and the five dimensions of wealth that go far beyond your bank account. If you’ve ever wondered what comes after success, this episode reveals how true wealth begins the moment you start living it. Conn...

Marshall Hayes grew up in rural Oregon learning about money from a handwritten ledger his dad kept on a yellow pad. Those early lessons sparked a fascination with investing and entrepreneurship that led him from cleaning bathrooms to building and selling a multimillion dollar marketing agency. For years, he chased success at all costs. The business grew fast, but behind the scenes, he was burning out, losing his relationship, and unraveling under the weight of anxiety and perfectionism. When eve...

Keith Latson was living the dream he had built since childhood. He was operating on Kentucky Derby champions, making seven figures, and working with the most elite horses and trainers in the world. But despite the money and accolades, something was missing. In this conversation, Keith shares what it felt like to stand at the pinnacle of his profession and realize he no longer recognized the man he had become. What followed was a total reorientation. He left his career in equine surgery and stepp...

Dr. Vassily Eliopoulos (Dr. Vass) spent more than a decade working in emergency rooms, treating people in moments that stripped away everything nonessential. Again and again, he sat beside patients who were facing the end and spoke the kind of truth that only becomes possible when there is no time left to pretend. Those moments became his teacher. In this conversation, Vass shares the quiet lessons that most of us miss in the noise. He speaks not just as a physician, but as someone who had to co...

Taylor Frame learned to sell on a Mormon mission in North Carolina. For two years, he knocked on doors, faced rejection, and refined his pitch one conversation at a time. This taught him how to connect, adapt, and keep pushing. That mindset carried him into tech sales and eventually entrepreneurship. He built a seven-figure agency, moved his family to the beach, and created what looked like the perfect life. Beneath the surface, he was unraveling. The harder he worked, the more disconnected he f...

Melanie Balke has built a life most entrepreneurs chase for years. Her business is thriving, her team is energized, and her days move with clarity and intention. She surfs, leads with presence, and shapes her calendar around the rhythm that brings out her best work. Her path reflects more than strategy. It is an identity shift rooted in emotional wealth, sustainable leadership, and the freedom to live life on her terms. This is the inner game of building something that lasts without losing yours...

Delroy Gill grew up flipping candy in the playgrounds of South London, finding creative ways to make money at a young age. When he moved to America, saw the game from a different angle, and started building something far beyond himself. Early on a broken promise taught him that if he wanted something, he had to get it himself. That mindset carried him through the 2008 crash, into real estate, and all the way to the top of the luxury market. But the climb came with a cost. The walls he built to p...

Jack Swift followed the path to success with precision. He graduated from West Point, served as an Army Ranger, and grew to CEO of TIFIN, a category-defining AI fintech platform valued at $842M. Jack spent years building a successful life. He had the titles, the income, and the momentum. Over time, the long hours and constant pressure wore him down, until even the wins stopped feeling meaningful. He realized he was building from fear instead of alignment, and it was costing him his health, his c...

Early life wasn’t easy for Rob Sirstins. He was born into poverty, adopted young, and raised in a world where he never felt like he belonged. Then he rose to success as a Division 1 football star with a career path in sales. From the outside, everything looked perfect. Then injury, betrayal, and loneliness stripped it all away and Rob found himself in a Salt Lake parking lot, finger on the trigger. That night, he chose to live and everything changed. What followed was a rebirth found through pla...

Anthony Vicino once believed financial wins meant freedom. He went from living in a van and scaling cliffs to building million-dollar businesses - only to see it all collapse when betrayal and bankruptcy left him in serious debt. In this raw episode, Anthony shares how losing millions didn’t just reset his bank account - it reshaped his definition of wealth, purpose, and what a rich life truly looks like. We dive into: -How van life and rock climbing shaped Anthony’s earliest views on money and ...

For years, Derek Coburn watched high achievers sacrifice health and joy in pursuit of a “magic number” they believed would bring freedom - only to feel empty when they reached it. In this powerful episode, Derek flips the script on traditional financial wisdom and reveals a truth most advisors won’t say out loud. We dive into: •How to design a life so aligned and fulfilling you’d never want to retire from it. •The hidden cost of postponing happiness and why “later” is the most expensive word in ...

What does it take to unlock your full potential, and why do so many high achievers sabotage themselves before they reach the top? In this conversation, I sit down with world-renowned hypnotherapist and mindset coach Elliot Roe, whose clients include world champion poker players, UFC fighters, Wall Street traders, and entrepreneurs. We dive into: How childhood experiences quietly program your “wealth thermostat” and self-worth. The hidden fears of rejection, isolation, and even success that keep ...

It started with a joke from his childhood. Dave’s mom told him they could afford a new bra for her or hockey gear for him. Then something snapped. That moment became more than a memory, it became a mission - he would never let money limit the life he wanted to live. And so he chased that life - financial freedom, independence and success on paper. But the higher he climbed, the more disconnected he felt, until it all came crashing down. In this deeply personal conversation, Dave and I walk throu...