Episodes

Julie Wainwright transformed the stigma around “used” luxury into a movement worth over a billion dollars. The founder of The RealReal, reveals the story behind the luxury resale empire that changed how the world shops for secondhand fashion. In conversation with Jess Larsen, she shares how she identified a market gap Amazon couldn’t fill, scaled from her living room to IPO, and turned setbacks into strategy. Learn more about your ad choices. Visit megaphone.fm/adchoices

What do Apple, Google, Meta, and Microsoft all have in common? They’ve all relied on Glenn Gow’s expertise. Having coached over 20 CEOs, advised Fortune 500 companies, Glenn joins Jess Larsen to talk about the brain science of leadership, why top founders and athletes all rely on coaches, and how AI is becoming a make-or-break tool for companies. Learn more about your ad choices. Visit megaphone.fm/adchoices

Biotech might produce the world’s next trillion-dollar company—and Simba Gill and Steve Ledger are betting on it. Join Jess Larsen as he explores how Serina Therapeutics’ drug optimization platform could reshape the future of treatment for Parkinson’s, cancer, and beyond. Simba, with four decades of biotech leadership, and Steve, with roots in finance and venture, share how science, capital, and mission come together to drive massive impact. This is a behind-the-scenes look at what happens when ...

Great business isn’t about math alone — it’s about understanding people. Blair LaCorte explains why his biggest lessons came from watching human behavior: investors chasing momentum, CEOs blinded by ego, or leaders too afraid to pivot. From negotiating a $400M Microsoft PIPE to navigating IPO mania, Blair shows how psychology, not spreadsheets, drives billion-dollar outcomes. For founders, investors, and leaders, this conversation is both raw and practical. Learn more about your ad choices...

Michael Episcope started his career on the chaotic trading floor of the Chicago Mercantile Exchange, twice ranked as one of the top 100 traders in the world. But when automation disrupted his industry, he pivoted. With his own wealth on the line, he co-founded Origin Investments in 2007, just before the financial crisis. In this episode with Jess Larsen, Michael shares the hard lessons from losing money in bad deals, the pivot during 2008 that set up Origin’s growth, and how they scaled to more ...

What do millionaires and billionaires know that the average person doesn’t? That it only takes one lawsuit to wipe out a lifetime of work. In this episode, Jess Larsen sits down with Hillel Presser, attorney and founder of The Presser Law Firm, to reveal the step-by-step strategies the wealthy use to bulletproof their assets. From protecting homes and businesses to safeguarding investments and retirement accounts, Presser explains how anyone — not just the ultra-rich — can secure their future. T...

From record-breaking $160M sales to becoming a real estate media empire, Ryan Serhant has redefined what it means to lead with confidence. In this episode, Ryan breaks down the mindset, systems, and self-belief behind his success—including his signature "5 Ps of Power." This isn’t just about real estate. It’s about building a brand that outlasts the market. Learn more about your ad choices. Visit megaphone.fm/adchoices

What does it take to lead a team where decisions happen at 60 mph and trust can’t wait? SailGP Canada Team Coach Billy Gooderham shares the highs and heartbreaks of racing, including recovering from a devastating crash, staying mentally sharp under pressure, and turning risk into high performance. This is leadership—wind, speed, and all. Learn more about your ad choices. Visit megaphone.fm/adchoices

Mark Gerson has built businesses, launched global charities, and written books proving the Torah’s practical power. In this episode of The Jess Larsen Show, he unpacks the wisdom behind rest, generosity, and mission-driven leadership. Whether you’re scaling a company or searching for your calling, his stories will inspire you to rethink what success really means. This is a conversation about community, conviction, and the surprising ROI of doing good. Learn more about your ad choices. Visi...

Jess Larsen and guest co-host Dr. Greg Bailey sit down with world-class sailor Paul Campbell-James (aka CJ), wing trimmer for the Canadian SailGP team, to talk about the speed, strategy, and stakes behind one of the most cutting-edge sports on water. CJ shares stories of competing at 60 mph, racing days after breaking his leg, and what elite sailing teaches us about teamwork, leadership, and resilience under pressure. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jess Larsen sits down with real estate innovator and PropTech entrepreneur Rob Finlay to dive into his new book, Beyond the Building. They explore why top-performing real estate operators are thinking more like tech founders—and how to build enterprise value through adaptability, data, and leadership. From capital strategy to OKRs, Rob shares the mindset and mechanics behind scaling smarter in today’s evolving market. Learn more about your ad choices. Visit megaphone.fm/adchoices

Sal Sferlazza, CEO of Ninja One, discusses the challenges of managing a company experiencing rapid growth. Learn how to balance the needs of long-term employees with the influx of new talent, maintain product quality, and make strategic decisions about expanding into new markets. Learn more about your ad choices. Visit megaphone.fm/adchoices

Learn how Des Hague integrated philanthropy into his business ventures, raising millions of dollars for various causes and initiatives. He shares the story behind his partnership with Juma Ventures, which provided employment opportunities for thousands of at-risk youth Learn more about your ad choices. Visit megaphone.fm/adchoices

As the pioneer in litigation finance, Burford Capital has a unique perspective on the industry's future. CEO Christopher Bogart discusses the potential financial shakeout in mass tort litigation funding and shares his predictions for the evolving legal finance landscape. Learn more about your ad choices. Visit megaphone.fm/adchoices

Discover the insider strategies and mindset that allowed David Weisburd, a seasoned venture capitalist, to turn a $7 million investment into a staggering $500 million exit. In this exclusive interview, David shares his unique approach to identifying and backing the most promising startups, and reveals the key traits he looks for in founders to ensure outsized returns. Whether you're an aspiring entrepreneur or an investor looking to sharpen your skills, this episode is packed with invaluable ins...

Two-time Olympic gold medalist Giles Scott discusses his remarkable journey from youth sailor to SailGP driver. Hear about the experiences, decisions, and lessons learned that have shaped Scott's career and made him one of the most successful sailors of his generation. Learn more about your ad choices. Visit megaphone.fm/adchoices

What does it take to build a truly customer-centric company? Eléonore Crespo, CEO of Pigment, reveals her strategies for putting customers at the heart of everything they do. From regular check-ins and surveys to quarterly business reviews and customer advisory boards, Eléonore and her team go above and beyond to understand their customers' needs and challenges. Discover how this unwavering focus on customer success has fueled Pigment's rapid growth and $1 billion valuation. Learn more ...

Can generosity be a competitive advantage in business? In this thought-provoking episode, entrepreneur Ajay Nwosu shares how adopting an abundance mindset and helping others has propelled his success across various industries. From creating a groundbreaking sport to managing a $100 million impact investment fund, Ajay's journey showcases the power of building relationships and giving back. Join hosts Jess Larson and Dr. Greg Bailey as they delve into the role of generosity in business and its profound effects on personal fulfillment and community growth. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Alex Dean, co-founder of Divvy and Tandem, shares his journey of building Divvy from a small startup to a company that sold for $2.6 billion. He discusses the key principles that led to Divvy's success and how he's applying those lessons to his new venture, Tandem. Tune in for valuable insights on scaling a company, hiring the right people, and maintaining a strong vision. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Frank Rodriguez challenges the conventional wisdom surrounding budgets. Discover his unique approach to measuring progress and success in business, and learn why focusing on year-over-year growth is more effective than relying on arbitrary budgets. Learn more about your ad choices. Visit megaphone.fm/adchoices

Embark on an inspiring journey with Alastair Callender as he shares his story from learning to sail as a young boy in England to becoming a trusted advisor to billionaires in the world of superyachts. Learn about the mentors who shaped his path, including the legendary sailor Sir Peter Blake, and how their guidance led him to combine his passions for yachting and philanthropy. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, we trace Kimberly Flynn's career path from her early days at Morgan Stanley to her role in helping raise $13 billion for innovative products at Nuveen. Discover the lessons she learned along the way and how they shaped her entrepreneurial venture, Zeia Investments. Learn more about your ad choices. Visit megaphone.fm/adchoices

Join us as we dive into the inspiring story of Annie Haeger, a world-class sailor who overcame Olympic disappointment to become a trailblazer in the thrilling world of SailGP. Discover how Annie's resilience, passion, and commitment to being brave led her to excel in one of the most demanding and exciting sailing competitions on the planet. Learn more about your ad choices. Visit megaphone.fm/adchoices

In his new memoir, "Hits, Flops, and Other Illusions," director Ed Zwick opens up about his life and career in Hollywood with unprecedented candor and insight. In this episode, Ed shares some of the most memorable stories from the book, from his early days as a struggling filmmaker to his collaborations with some of the biggest names in the business. If you're looking for a fascinating, behind-the-scenes look at the world of filmmaking, this is an episode you won't want to miss. Learn more...