From Start-Up to Grown-Up

121: Founder Mode on Bitcoin: Double the Volatility, Double the Stakes | Will Reeves, Co-Founder and CEO of Fold 29.06.2026 50min

Building a startup on Bitcoin means you're not riding one rollercoaster, you're riding two at once. The volatility of launching a company is hard enough. Layer on top of that a protocol still finding its own product-market fit, and you get a compounding effect that will break founders who aren't prepared for it. Will Reeves knows this firsthand. He co-founded Fold, lived through deep bear markets with no investor interest in sight, made a critical pivot after realizing he was building t...

120: Miro's Founder on Reinventing a 100-Million-User Company | Andrey Khusid, Founder of Miro 15.06.2026 46min

What happens when you've already built a company used by more than 100 million people, and suddenly the world changes again? In this episode, Alisa Cohn sits down with Andrey Khusid, Founder and CEO of Miro, to explore one of the biggest leadership challenges founders face: reinventing a successful company while it's still growing. As AI transforms the way teams work, Andrey shares how Miro evolved from a digital whiteboard into a collaborative platform where humans and AI agents create toget...

119: Eric Ries, Author of The Lean Startup, The Corporate Governance Crisis No One Wants to Admit 01.06.2026 48min

What if the biggest threat to your company is not competition, but the systems everyone told you to trust? In this episode, Alisa Cohn sits down with Eric Ries, creator of the Lean Startup methodology and bestselling author of The Lean Startup, The Startup Way, and Incorruptible, for a conversation about leadership, corporate governance, innovation, and why so many modern companies lose their way as they grow. Eric unpacks the dangerous side of “best practices,” why shareholder primacy often ...

118: Josh Reeves, Co-Founder and CEO of Gusto, The 3-Part Alignment Framework Every Founder Needs Before Their Next Hire [ENCORE] 18.05.2026 1h 6min

What if you have been hiring wrong this entire time? In this episode, Josh Reeves, Co-Founder and CEO of Gusto, a $10B people platform serving over 300,000 businesses, joins Alisa Cohn for one of the most practical and deeply human conversations about building teams that actually work. This is not a generic leadership talk. This is a masterclass in how to hire people who genuinely care, how to scale a values-driven culture without losing it, and how to lead through the kind of uncertainty tha...

117: Jyoti Bansal, Two-Time Founder, How to Win the AI Race Before Your Competitors Catch Up 04.05.2026 1h 2min

What happens after you “make it”… and realize money was never the point? In this episode, Jyoti Bansal, Founder & CEO of Harness and founder of AppDynamics (sold for $3.7B), sits down with Alisa Cohn for a conversation that cuts deeper than typical startup playbooks. This is not just about building companies. It’s about what happens when the finish line disappears… and you have to decide who you are without it. Jyoti shares the unexpected identity crisis that hit after his exit, why he ch...

116: Gina Bianchini, Founder of Mighty Networks, Stop Building an Audience. Build Community Instead [ENCORE] 20.04.2026 1h 1min

What if the thing you’ve been told to build… isn’t the thing that actually creates results? In this encore episode, Gina Bianchini joins Alisa Cohn to break down why community, not content, not audience size, not algorithms, is the real driver of transformation, retention, and long-term business growth. This conversation goes far beyond theory. It’s a masterclass in how communities actually work, why most founders get it wrong, and what it really takes to build something people don’t just fol...

#115 – Tanay Kothari, Co-Founder & CEO of Wispr Flow: How a 27-Year-Old Founder Is Redefining Leadership, Product, and the AI Revolution 06.04.2026 1h 5min

What does it actually take to lead when the stakes are real, the decisions are heavy, and people are counting on you? In this episode of From Start-Up to Grown-Up, Alisa Cohn sits down with Tanay Kothari, Co-Founder and CEO of Wispr Flow, one of the most talked-about AI companies right now, to explore what it means to build, lead, and grow at a level most founders never reach. Tanay may be a young founder, but the way he thinks about leadership, people, and decision-making is anything but ear...

#114 - Kim Scott, Radical Respect and Radical Candor: How to Build Teams That Challenge Directly and Care Personally [ENCORE] 23.03.2026 1h 18min

What does it actually mean to care about someone at work? In this encore episode, Alisa Cohn sits down with Kim Scott, former Apple and Google executive and bestselling author of Radical Candor and Radical Respect, to explore the real cost of silence, bias, and avoidance inside teams. This episode is not theoretical. It is deeply practical. From how to solicit feedback effectively, to how to “disrupt bias without disrupting the meeting,” to how to move through shame and defensiveness, Kim off...

#113 – Matt Oppenheimer, from Founder to Public Company CEO of Remitly: Why Falling in Love with the Problem Builds Enduring Companies 09.03.2026 54min

What does it really take to evolve from first-time founder to public company CEO without losing conviction, culture, or clarity? In this episode of From Start-Up to Grown-Up, Alisa Cohn sits down with Matt Oppenheimer, Co-Founder and CEO of Remitly, the global financial services company serving customers in more than 170 countries. Matt shares the leadership evolution behind building Remitly from an early-stage startup into a publicly traded company. From spotting the broken experience of int...

#112 - Sal Di Stefano, Co-Founder of Mind Pump Media, How Authenticity, Cofounder Alignment, and Physical Strength Shape Great Leadership [ENCORE] 23.02.2026 1h 22min

What actually drives long-term growth, in business, leadership, and life? In this replay episode, Alisa Cohn sits down with Sal Di Stefano, co-founder of Mind Pump Media, to explore what it really takes to build something that lasts. From turning a podcast into a multi-revenue media company to navigating cofounder relationships, conflict, and personal growth, Sal shares hard-earned lessons from nearly a decade of building Mind Pump without venture capital or shortcuts. This conversation goes ...

#111 – Dr. Becky Kennedy on Why Great Leaders Stop Managing Feelings and Start Building Trust 09.02.2026 51min

What does it actually mean to lead with authority and empathy, without burning out, people-pleasing, or losing yourself in the process? In this episode, Alisa Cohn sits down with clinical psychologist, parenting expert, and bestselling author Dr. Becky Kennedy to explore why the skills that make great parents also create the strongest leaders. Dr. Becky introduces the concept of sturdy leadership, a grounded approach that rejects both authoritarian control and emotional over-accommodation. In...

#110 Jim McKelvey, Cofounder of Square - Innovation When it's Your Only Choice, Overcoming Regulation, and Managing His Intern, Jack Dorsey [ENCORE] 27.01.2026 1h 4min

What does it actually take to build something that has never existed before? In this episode, Jim McKelvey, co-founder of Square (now Block), breaks down the real story behind building Square from scratch, not with a perfect plan, but through necessity, invention, and relentless problem-solving. Jim introduces the concept of the Innovation Stack, why innovation is rarely chosen willingly, and why copying “what worked before” fails when you’re solving a problem no one else has solved. He...

#109 Robbie Bent cofounder of Othership— From Rock Bottom to Community Buildering Community 12.01.2026 1h 18min

In this episode, Robbie Bent,CEO and Co-founder of Othership shares his remarkable journey from addiction recovery to leading one of today’s most innovative wellness brands. Othership combines sauna, ice bath, and guided breathwork to help people regulate their emotions and connect in community. Robbie opens up about the evolution of his leadership, the challenges of scaling a purpose-driven business, and the importance of authenticity as a founder. From a small Toronto garage gathering durin...

#108 Semyon Dukach— MIT Blackjack Team Former Leader, Current VC, Invests Only in Immigrants 30.12.2025 47min

Semyon Dukach, the Founding Partner at One Way Ventures, serial entrepreneur, and former leader of the famed MIT Blackjack team, joins me to share his extraordinary journey from arriving in the U.S. as a Soviet refugee to becoming one of New England’s top venture capitalists. We discuss his path from leading the MIT Blackjack team to startup founder to prolific investor. One Way Ventures invests only in immigrant founders and we discussed how he developed that thesis. We also talk about...

#107 Jonathan Wolf— Co-Founder and CEO of ZOE: The Growth of a Founder, the Most Important Leadership Skills, and How to Raise 7 Million Euros in 3 Weeks (Encore) 15.12.2025 44min

Jonathan Wolf is the co-founder and CEO of ZOE, the science-based nutrition company using data to transform how people eat. In this candid conversation, he joins me to explore what it takes to build a mission-driven company, how to lead with more clarity and transparency, and why the way we eat is more broken and more fixable than most people think. ZOE’s origin story is as unconventional as it is inspiring. After scaling Critéo into a billion-dollar business, Jonathan stepped away with no pl...

#106 Kass and Mike Lazerow— Serial Married Founders Sold their Company to Salesforce for $750M on Loving the Journey (Encore) 01.12.2025 1h 28min

Kass and Mike Lazerow who are serial entrepreneurs, seasoned investors, and co-authors of Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success joined me for one of the most honest conversations I’ve had about what it really takes to build companies and build a life. They share the unvarnished truth about their journey: surviving the dot-com crash, buying Golf.com back from bankruptcy, founding and scaling Buddy Media (eventually acquired by Salesforce for $745 million),...

#105 Randy Komisar— Legendary Kleiner Perkins Investor Shares the 3 “Whys” Every Founder Must Answer (Encore) 18.11.2025 1h 9min

Randy Komisar is an entrepreneur and investor at Kleiner Perkins. Previously, he was a co-founder of Claris Corp., served as CEO for LucasArts Entertainment and Crystal Dynamics, and acted as “virtual CEO” for such companies as WebTV and GlobalGiving. Randy also served as CFO of GO Corp. and as senior counsel for Apple Computer, following a private practice in technology law. Randy is a founding director of TiVo and serves on the Roadtrip Nation Advisory Board and Orrick’s Women’s Leadership ...

#104 Issac Evans— How a Series D CEO Found Product-Market Fit, Stays Self-Aware, and Survived His Bank Melting Dow 04.11.2025 1h 8min

In this episode, Alisa Cohn interviews Isaac Evans, co-founder and CEO of Semgrep, a startup giving security tools directly to developers. Isaac shares his journey from conducting research at the U.S. Defense Department and MIT Lincoln Laboratory, where he explored binary exploitation bypasses, control-flow integrity, and novel hardware defenses on architectures like RISC-V, to founding and leading a fast-growing company at the forefront of developer security. A graduate of MIT with BS and MS...

#103 Patrick Lee— Rotten Tomatoes Founder: The Secrets to Building an Enduring Business 20.10.2025 1h 16min

Patrick Lee is best known as the co-founder and founding CEO of Rotten Tomatoes, the groundbreaking review platform that reshaped how audiences connect with movies and television. What started as a side project born out of his love for film became a global authority that continues to influence critics, fans, and the entertainment industry. In this conversation, Patrick shares his journey from running a small web design firm to creating one of the most recognizable brands in pop culture. He op...

#102 Robert Glazer — Serial Entrepreneur on the Most Important Tool for Success 07.10.2025 1h 7min

Robert Glazer is the founder of Acceleration Partners, a serial entrepreneur, bestselling author, and a leading voice on how values shape leadership. In this episode, Bob shares why stepping down from the company he built triggered a surprising crisis of meaning, how that experience led him to write The Compass Within, and how helping people clarify their core values has become his new personal mission. Bob opens up about the link between pain and passion, the power of writing and brand-build...