Episodes

What does it really take to go from startup to category leader? In this episode of The Jess Larsen Show: Innovation & Leadership, Jess sits down with Avery Pennarun, CEO of Tailscale, to break down the real mechanics behind product-market fit, scaling to a billion-dollar company, and becoming the default choice in your industry. Avery shares hard-earned lessons from building Tailscale into one of the most respected infrastructure companies in tech—used by thousands of teams worldwide. From wh...

We’re revisiting one of our most fascinating conversations on The Jess Larsen Show on Innovation & Leadership. In this throwback episode, Jess sits down with billionaire investor, entrepreneur, and futurist Jim Mellon to explore the ideas shaping the future of business, technology, and human life itself. From his early days witnessing the rise of Silicon Valley alongside figures like Bill Gates and Steve Jobs, to building a global investment career across emerging markets, Jim shares the m...

This episode is a masterclass in leadership, scale, and hard-earned business wisdom. Jess sits down with Gary Kusin—founder of GameStop (formerly Babbage’s), former CEO of Kinko’s, and a leader behind one of the most impressive turnarounds in retail history—to unpack the lessons that shaped his career. Gary shares the real story behind taking Kinko’s from negative EBITDA to a $2.4B acquisition by FedEx, what it was like working directly with Fred Smith, and the leadership principles he develo...

From Wall Street to humanoid robotics, Andrew Kiguel has built a career at the edge of what’s next—and in this episode, he sits down with Jess to unpack what it actually takes to bet on the future before it’s obvious. Andrew, CEO of Realbotix, shares how his journey through investment banking, crypto mining, and high-growth ventures led him to one of the most controversial and fascinating frontiers today: human-like AI robots. From building a $140M revenue crypto company to now developing lif...

In this episode, Jess sits down with Ross Buhrdorf, Co-Founder and CEO of ZenBusiness, to unpack what it really takes to build companies that matter. From helping lead HomeAway through its massive growth and $3.9 billion exit to Expedia, to building ZenBusiness into a billion-dollar platform serving entrepreneurs across America, Ross shares lessons from the front lines of scaling, fundraising, product-market fit, and leadership. He explains why small businesses are the backbone of the economy, h...

What if the most powerful business strategy today isn’t AI, automation, or scale… but relationships? In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with serial entrepreneur and investor Noah Berkson to talk about the surprising power of real human connection in a digital world. Noah shares how he went from a self-described terrible student with ADHD to building and exiting multiple companies—including a recent sale of his farmland marketplace—by focusing on re...

In this episode, Jess sits down with bestselling author Nir Eyal to unpack his newest book, Beyond Belief — and the conversation goes far deeper than productivity hacks or surface-level motivation advice. Nir, the author of Hooked and Indistractable, explains why knowing what to do isn’t the problem. We already have more information than ever. The real challenge is understanding why we don’t do what we know we should. He breaks down the hidden power of belief — how limiting beliefs quietly sabot...

What does it take to jump into a war zone, break a world record, and still come home grounded? In this episode of The Jess Larsen Show, Jess sits down with former Tier 1 Special Boat Service operator Dean Stott to unpack a life that sounds like fiction—but isn’t. Dean shares what it really means to pass one of the world’s toughest special forces selections, why humility and integrity matter more than bravado, and how mindset separates those who quit from those who finish. He opens up about un...

We’re revisiting one of our standout conversations on The Jess Larsen Show on Innovation & Leadership. In this throwback episode, Jess sits down with Glenn Fogel, CEO of Booking Holdings, to unpack the leadership story behind one of the internet’s most remarkable growth narratives. From navigating the dot-com crash to steering through global uncertainty and economic downturns, Glenn shares how long-term thinking, disciplined execution, and relentless focus on product and service helped transfo...

Throwback episode alert. We’re re-releasing one of the most replayed conversations on The Jess Larsen Show. Jess sits down with retired FBI international kidnapping negotiator Chris Voss, bestselling author of Never Split the Difference. Chris takes you inside real hostage negotiations and breaks down the skills that actually move people: tactical empathy, listening for what’s unsaid, staying calm under pressure, and using the right words when stakes are high. This one isn’t just for dealmaker...

This is a repost of one of our favorite episodes. Jess Larsen is joined by Dr. Greg Bailey (biotech investor behind the $11.6B Nurtec exit and a $14.3B Pfizer deal) and Brant Pinvidic, the Hollywood pitch guy who’s sold more than 300 shows and wrote The 3 Minute Rule. Brant talks about leaving Canada, landing in the U.S., and why the “big ideas” weren’t the problem. The problem was getting people to understand them fast. He breaks down why so many founders and CEOs struggle to say what the...

This is an older episode, but it’s one of those conversations that still holds up. Jess Larsen sits down with Jim Stengel to talk about what actually makes companies and leaders last. Not trends. Not hacks. Just the hard-earned lessons that come from seeing brands grow, stumble, and sometimes lose their way. They talk about focus, trust, and why the best organizations are built around serving people—not chasing the next shiny thing. It’s calm, thoughtful, and surprisingly grounding. We’...

We’re resurfacing a favorite Jess Larsen Show conversation with Keith Ferrazzi—bestselling author of Never Eat Alone and the follow-up, Never Lead Alone. In this episode, Keith breaks down why the next era of leadership isn’t “hero CEO” energy—it’s teams stepping into leadership together. Jess and Keith connect the dots between lean/TQM, agile, and what Keith calls the real opportunity right now: re-engineering collaboration and workflows (not just debating office polices). You’ll hear pra...

In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Jessica Markowski from SERHANT. (and Netflix’s Owning Manhattan) to talk about using media as a real business advantage—not a vanity play.Jessica shares how she treats Instagram like a curated portfolio and TikTok like a playground, why she focuses on the work (not follower counts), and how visibility turns into inbound clients—from Starbucks conversations to serious listings. They dig into the mindset shift ...

This is a repost of an earlier episode of the Jess Larsen Show on Innovation & Leadership. In this episode, Jess Larsen sits down with Kyle Hanslovan, cybersecurity expert and CEO of Huntress, to unpack what it really takes to protect small and mid-sized businesses from modern cyber threats. Long before Huntress became a trusted name in defensive security, Kyle’s journey began in the U.S. Air Force, continued through the intelligence community, and ultimately led him into the front lines of cybe...

Bootstrapping to a $4.2B Global Powerhouse: Inside G-P with Founder & CEO Nicole Sahin What does it take to turn a complex, “impossible” idea into a multi-billion-dollar global infrastructure company — without raising a dollar of venture capital for the first eight years? On this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Nicole Sahin, Founder & CEO of G-P (Globalization Partners), the company that pioneered the global Employer of Record model and grew it int...

Seth Godin on Significance, Status, and the Future of Work This episode is a special repost from the archives of The Jess Larsen Show on Innovation & Leadership, featuring legendary author and thinker Seth Godin. Originally recorded around the launch of his book The Song of Significance, this conversation feels even more relevant now than when it was first released. Seth and Jess dig into why the industrial age model of work is breaking down—and what should replace it. They talk about how to ...

In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Holly Parker, legendary NYC broker, bestselling author, and founder of The Holly Parker Team—personally responsible for more than $13 billion in sales. Holly opens up about the real secrets behind long-term success: empathy, emotional intelligence, impeccable integrity, and the ability to serve clients in ways that have nothing to do with square footage or contracts. Holly shares stories from behind the sc...

Luxury, Trust & the Future of Travel: Inside THIRDHOME with Giles Adams What if your second home wasn’t just a retreat—but a passport to the world’s most extraordinary properties? In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Giles Adams, Partner & President at THIRDHOME—the global private club redefining luxury travel, home exchange, and how the world’s wealthiest families experience their time off. With more than 20,000 properties across 103 countries,...

From $700 a Month to a $9B Giant: Building Life360 with Chris Hulls What happens when a founder ignores the “safe path,” bets on himself, and keeps going long after most people would’ve quit? In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Chris Hulls — Co-Founder and Executive Chairman of Life360, the world’s largest family safety platform with 90+ million monthly active users and a public valuation approaching $9 billion. Chris’s journey is anything but ...

Dr. Gordon Neufeld—developmental psychologist and author of Hold On to Your Kids—joins Jess to explain why our children’s greatest need is not techniques, but relationship. Discover the true cost of peer orientation, the five relational needs that never expire, and the power of boredom, nature, and play to refuel connection. Neufeld shares how he won back his own daughters by removing competing attachments and rebuilding time, trust, and warmth. This is a field guide for modern parents who wa...

Eva Yazhari shares hard-earned lessons from Wall Street, her time managing billions, and what she’s learned saying “no” to short-term thinking. This episode is a masterclass in balancing risk, resilience, and relationships. Learn more about your ad choices. Visit megaphone.fm/adchoices

Can trauma be inherited across generations? And more importantly—can it be stopped? Dr. Nadine Burke Harris has spent her career answering those questions. As California’s first Surgeon General, she championed screening for ACEs, built networks between clinics and communities, and pushed for policies that save lives. In this conversation with Jess Larsen, Nadine shares the science, the policy battles, and the deeply human side of this work—from seeing patients transformed when told “you...

Venture capital isn’t luck — it’s math. Jess Larsen sits down with Jamie Rhode, Partner at ScreenDoor, to reveal how elite allocators consistently hit 3× returns and 20–25% CAGR over decades. They break down 42 years of VC data, the power law behind billion-dollar outcomes, and how top investors turn volatility into long-term advantage. Learn more about your ad choices. Visit megaphone.fm/adchoices