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...

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...

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),...

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 ...

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...

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...

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...

Nick Huber is an entrepreneur and real estate investor who resides in Athens, Georgia, with his wife and three children. He owns Somewhere.com, Bolt Storage, RE Cost Seg, and several other businesses. His real estate portfolio currently includes sixty-eight self-storage properties, covering two million square feet. His portfolio of companies employs over 325 people and makes over $35 million annually. He’s the author of “The Sweaty Startup: How to Get Rich Doing Boring Things.” Where ...

Arvind Jain is the founder and CEO of Glean, the Work AI platform that connects to all your company’s data so you can find, create, and automate anything. In this episode, Arvind shares his journey as a second-time founder and first-time CEO, reflecting on the challenges of moving from a deeply technical role into leading an organization. He talks about why selling is one of the most important skills for founders, the importance of hiring for desire and cultural fit, and how company culture a...

Naveen Verma is a professor of electrical and computer engineering at Princeton and the co-founder and CEO of EnCharge AI, a startup building radically energy-efficient computers for artificial intelligence. In this episode, Naveen shares how his academic research into in-memory computing evolved over six years into a venture-backed company that’s rethinking the physical limits of AI computers. Naveen explains why traditional computing models can’t keep up with the energy demands of AI, how i...

Craig Walker is the founder and CEO of Dialpad, a business communications platform powered by AI. A former M&A lawyer turned serial entrepreneur, Craig previously co-founded GrandCentral (acquired by Google and relaunched as Google Voice) and sold his prior company to Yahoo. In this episode, Craig shares how his career unfolded from door-to-door dictation sales to running a 1,500-person company, and how AI became central to Dialpad’s strategy long before the hype cycle. Craig opens up abo...

Brad Feld has spent over 40 years building companies, mentoring founders, and investing in the startup ecosystem. He’s the co-founder of Techstars, a prolific venture capitalist, and the author of nine books. In this episode, Brad opens up about the mental reset that came with turning 60, why he stopped chasing “more,” and what led him to dust off a book draft about mentorship that had been sitting on the shelf. We go deep into his new book Give First, his belief in non-transactional ge...

David is the creator of Ruby on Rails, Co-Owner of 37signals, best-selling author, Le Mans class-winning racing driver, antitrust advocate, investor in Danish startups, frequent podcast guest, and family man. He writes regularly on HEY World and speaks on The REWORK Podcast. Hundreds of thousands of programmers around the world have built amazing applications using Ruby on Rails, an open-source web framework he created in 2003, and continues to develop to this day. Some of the more famo...

Bob Young co-founded Red Hat, the first company to build a successful business around open source software, and helped shape the modern internet in the process. In this episode, Bob shares the story of how Red Hat went from a CD in a Ziploc bag to a billion-dollar business that inspired GitHub, Coinbase, and much of the cloud infrastructure we use today. But this conversation is about more than just software. Bob opens up about betting his family’s finances on Red Hat, the moment he realized ...

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 Alisa 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...

Kass and Mike Lazerow are serial entrepreneurs, seasoned investors, and co-authors of the upcoming book Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success. They join Alisa to share an unfiltered look at what it really takes to build companies, navigate chaos, and stay married through it all. Known for founding Golf.com and Buddy Media, which they sold to Salesforce for $745 million, Kass and Mike have also backed more than 100 early-stage startups. Their portfolio inc...

David Ko is the CEO and board member of Calm, the #1 app for sleep, meditation, and mindfulness. A former healthcare executive and tech operator, David previously served as COO of Zynga, held senior roles at Yahoo!, and founded a healthtech company acquired by Calm. He is the bestselling author of Recharge, and has been recognized by TIME, LinkedIn, RockHealth, and NYU Stern for his leadership in digital health. What you’ll learn: How David transitioned from gaming to healthcare through miss...

Mike Seckler is a two-time entrepreneur and tech startup founder who led a company through the dot-com boom and bust, and now leads the charge as CEO of Justworks, the HR tech company focused on uplifting small businesses. In this conversation, he shares hard-earned lessons from building one of the earliest SaaS HR startups, navigating turbulent markets, and guiding Justworks through major transitions. We dive into founder resilience, building high-functioning boards, scaling culture in a hyb...

Jeff Byers is the co-founder and CEO of Momentous, a high-performance wellness company delivering science-backed products used by elite athletes, military operators, and high-performers worldwide. A former NFL player and two-time USC football captain, Jeff brings both personal and professional insight to optimizing performance and building values-driven companies. What you’ll learn: Why Jeff says effort and attitude are the only things you can control—and how they ground him in tough momentsT...

Kevin Evers is a Senior Editor at Harvard Business Review, where he shapes groundbreaking research and develops award-winning and bestselling books on high performance, creativity, innovation, marketing, and digital disruption. He’s also written popular essays on brain science, persuasion, unpredictability, and the power of storytelling. Kevin holds degrees in English and Film Studies, and his forthcoming book with HBR Press, There’s Nothing Like This, offers a strategic analysis of Taylor Sw...