Episodes

What if the reason you're not earning what you're worth has nothing to do with your skills — and everything to do with the stories you believe about money? Are you showing up like someone who knows their value… or playing it small to keep the peace? Let’s be real — money is messy. It brings up all kinds of emotions, expectations, and unspoken rules. In this solo episode, I’m sharing something personal: my own journey around money, self-worth, and what it’s taken for me to finally feel comfortabl...

“No one works as hard as founders do. They’re operating on another level of intensity.” - Medha Agarwal Is your pitch holding you back more than your business idea? Are you making it easy for investors to dream the dream with you? In this episode, I sit down with Medha Agarwal, General Partner at Defy, to talk about the unique challenges founders face—especially women—when pitching their startups, securing funding, and leading through growth. She shares why too many founders unknowingly underse...

"My role is catching the ideas and making them happen." – Stephanie Unwin Is your leadership moving forward, or are you just keeping busy? In the fast-paced world of executive leadership and entrepreneurship, it can feel impossible to carve out time to think strategically. But what if making space for reflection isn’t a luxury—it’s the key to unlocking long-term success? In this episode of Transformative Leadership Conversations, I sit down with Stephanie Unwin, a seasoned executive and busine...

What makes some founders incredible leaders—and others impossible to work with? They are visionaries, but are they always great leaders? Founders bring passion, vision, and drive, but they can also be intense, stubborn, and relentless. Working with them isn’t just about executing their vision—it’s about knowing when to support, when to challenge, and how to scale alongside them. So how do you do that effectively? In this episode of Transformative Leadership Conversations, I dive into what makes...

“Leadership without courage isn't leadership at all, but courage without integrity is dangerous.’’ - Winnie da Silva What if your fear was the key to unlocking your greatest leadership potential? In this episode of Transformative Leadership Conversations, I explore the often-overlooked power of fear in leadership. Fear is something all leaders face, but it's not the fear itself that defines us—it's how we respond to it. You’ll hear me discuss how we can transform fear from a roadblock into a po...

"The old model of leadership, commanding, dominating, and never admitting failure, is outdated, and more importantly, it's ultimately ineffective." - Winnie da Silva Is humility the secret weapon some leaders are overlooking? In today’s fast-paced world, we’re taught to believe that the most successful leaders are the loudest, the boldest, and the most aggressive. But what if humility, often seen as a weakness, is actually the missing ingredient to becoming a more effective and respected leader...

"Encouraging disagreement strengthens decision-making, challenges blind spots, and creates an environment where people feel heard." - Winnie da Silva What if avoiding disagreement is actually holding you back? Most of us instinctively avoid conflict. We’re taught that disagreeing can damage relationships, create tension, or make us look difficult. But what if I told you that the way we approach disagreement could be the key to making better decisions, building stronger teams, and gaining real ...

"Motivation starts with identity—when you believe in the story you’re telling yourself, the actions follow." - Nikhil Paul Is it possible to lead with passion and effectiveness if you no longer feel connected to the business you're running? In this engaging conversation, I have with leadership coach Nikhil Paul, he dives deep into the heart of leadership, self-reflection, and sustainable business practices. Nikhil emphasizes the importance of personal connection to the work and the culture, ask...

"When you align individual motivation with the broader mission, that’s when magic happens and teams thrive.” - James Thorman What does it take to lead a team with purpose, ignite individual motivation, and build a thriving, high-performing culture? In this episode of Transformative Leadership Conversations, James Thorman, a seasoned leader with a wealth of experience from his time at A Place for Mom and other roles, joins me to dive deep into the core elements of effective leadership. He explai...

"Leaders can't motivate people—and nor should they. But what you can do is foster an environment where intrinsic motivation can thrive." - Winnie da Silva What if I told you that motivating your team isn’t your job? It sounds counterintuitive, right? As a leader, your instinct is to inspire your team to perform at their best—but real, lasting motivation comes from within. In this episode of Transformative Leadership Conversations, I challenge the traditional view of leadership by flipping the s...

"Diversity of thought is very powerful. I aggressively seek out people that don’t think like me and are polar opposites of me. That’s the only way to pull yourself out of your own corner." - Mauhan Zonoozy  What if the biggest barrier to innovation isn’t a lack of ideas—but a fear of permission? In this episode of Transformative Leadership Conversations, I sat down with Mauhan Zonoozy, a strategic advisor and expert in innovation and venture building. Mauhan shared bold perspectives on why pe...

What if innovation isn’t just for a select few, but something every single person can access and contribute to? In this episode of Transformative Leadership Conversations, I had the chance to chat with Sandy Fershee, the Head of Design & User Experience at Audible. Sandy shared some truly inspiring thoughts about innovation—how it’s not something reserved for just a select few, but something that everyone can contribute to. We talked about the importance of curiosity, creating psychological safe...

What if the biggest barrier to innovation within your team or organization is you? In this episode, I’m diving into the heart of innovation—what it means for leaders and how we can create an environment that allows it to thrive. I explore the essential role that leaders play in driving meaningful innovation and reflect on how we can overcome the distractions and barriers that keep us from unlocking our full creative potential. In this episode, you’ll hear about: The Innovation Leadership Style...

What’s your story, and how does it shape your brand? In this episode of Transformative Leadership Conversations, I sit down with Maria Ho-Burge, Vice President of Communications at TuneCore, to dive deep into the art of building a personal and professional brand. Maria shares how authenticity, storytelling, and strategy come together to create a brand that not only stands out but also drives value in any industry. From her work in the music industry to her insights into leadership and communica...

What does it take to drive change in a male-dominated industry while staying true to your vision? In this episode of Transformative Leadership Conversations, I sit down with Andreea Gleeson, CEO of TuneCore, to hear her remarkable story. Andreea shares how she transitioned from retail to music, the challenges she’s faced as a woman in leadership, and her mission to empower artists at every level of their careers. From tackling gender inequality in the music industry to fostering innovation at Tu...

How do people really see you, and does that match who you want to be? In this episode of Transformative Leadership Conversations, I take a close look at what it means to shape your leadership brand authentically. Through stories from real clients and practical advice, I’ll show you how to shape and evolve your brand to resonate and stand out in ways that genuinely reflect you. Listen in as I discuss: Defining Your Leadership Brand: It’s about aligning how people see you today with who you want...

How do I define success—and how does that shape the decisions I make? In this episode of Transformative Leadership Conversations, I have the pleasure of chatting with Cherie Hu, a music industry expert and the founder of Water & Music. Together, we dive into decision-making in both creative and business landscapes, exploring how our interpretations of success can shape our paths and the strategies we choose. You’ll here them discuss: Redefining Success: Leaders should understand that success c...

What happens when the very decisions you make as a leader cause unintended ripple effects throughout your organization? In this episode of Transformative Leadership Conversations, I sit down with Prita Kumar to explore the complex balance of short-term goals, long-term planning, and the law of unintended consequences in leadership. Prita shares her experience in managing teams without overwhelming them, how she thinks about qualitative vs. quantitative data, and why creating consistency across d...

What if the decisions you make as a leader are only addressing half the problem? In this episode of Transformative Leadership Conversations, I explore the hidden complexities beneath the surface of leadership challenges and how understanding those deeper issues can lead to more effective decision-making. I talk about the importance of not just focusing on what’s immediately visible but also considering the less obvious factors that might be driving the situation. By adopting a more thoughtful, s...

What if your relationship with work is fundamentally shaping your career decisions? In this episode, I speak with Dr. Nayla Bahri, an executive coach and co-host of The Inside Job Podcast. Nayla is dedicated to helping individuals and teams build thriving relationships with work, collaborating with leaders from startups to renowned organizations like Apple, Google, and the Federal Reserve Bank of NY. With her extensive experience as a former Dean of Students at Columbia Business School, she comb...

Ever wondered how you can turn your career dreams into reality? In this episode of Transformative Leadership Conversations, host Winnie da Silva sits down with career coach Maggie Mistal to explore how aligning your work with your passions can transform your life. Maggie Mistal, a certified life purpose and career coach and author of the Amazon #1 New Release Are You Ready to Love Your Job?, shares her own transition from the corporate world to coaching and reveals her method for career fulfillm...

Are you contemplating a career change but feeling uncertain about taking the leap? In this episode, Winnie explores the evolving nature of work and the increasing prevalence of career pivots. Sharing her own journey from social work to corporate training and consulting, she demonstrates how embracing these transitions can lead to unexpected and fulfilling opportunities. Through compelling statistics and inspiring stories of figures like Vera Wang and Benjamin Franklin, Winnie underscores that ca...

Can ensuring your team feels valued and supported be a tool to boost productivity? In this episode, Kim Lerner and host Winnie da Silva explore how hospitality principles, such as empathy and personalized recognition, can profoundly impact team culture and leadership effectiveness. Kim shares her unique experiences integrating these principles into her leadership approach, demonstrating how they can foster stronger team connections and drive organizational success. You will hear them talk about...

Can a leadership approach grounded in hospitality transform your organization's customer interactions and internal dynamics? In this episode, David Cocchiara and host Winnie da Silva discuss how principles of hospitality—like genuine accountability and composure under pressure—can significantly enhance leadership effectiveness and customer satisfaction. They explore why these seemingly simple strategies are challenging to implement and how they can make a profound difference in fostering positiv...