The Jess Larsen Show on Innovation & Leadership

Graystoke Networks

Jess Larsen interviews exciting people and uncommonly high achievers including Billionaires, Pro Athletes, Fortune 500 CEOs, Hollywood Actors like Danny Glover, New York Times Bestselling Authors, Tech Founders, Four-star Generals, World Class Musicians, Special Ops, VCs, Olympic Athletes, Non-Profit Leaders, Inventors and many more.

  1. 2d ago

    Why do 75% of Exits Fail? | Michael Winn, Co-Founder & Partner at Chartered Wealth Partners

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Michael Winn of Chartered Wealth for the first installment in a new mini-series on one of the biggest questions founders face: why do so many exits fail? Michael breaks down the surprising statistic that 75% of founder exits are unsuccessful, and explains why selling a company is not just a transaction, but a deeply personal, financial, and strategic process. Michael shares the three areas every founder must align before an exit: business readiness, financial readiness, and personal readiness. While most owners focus on whether the business is valuable and transferable, Michael explains why the emotional side is often the most overlooked and the most dangerous, especially when founders lose their identity, purpose, and daily adrenaline after the wire hits. Jess and Michael also explore real client stories, including founders who walked away from $300M+ deals, struggled after $120M exits, or discovered that their “magic number” was not what they thought. The conversation dives into estate planning, wealth gap analysis, tax mitigation, spouse alignment, and the importance of preparing for life after the sale long before the deal closes. Whether you’re actively preparing to sell, years away from an exit, or building a business you may never sell, this episode is a practical and eye-opening guide to avoiding founder regret and creating an exit on your terms, not the buyer’s. Learn more about your ad choices. Visit megaphone.fm/adchoices

    53 min
  2. Jun 11

    Ethereum Co-Founder's Sovereign AI Future | Anthony Di Iorio, CEO & Founder of Decentral

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Anthony Di Iorio, co-founder of Ethereum and one of the earliest builders in the crypto ecosystem, for a wide-ranging conversation on Bitcoin, Ethereum, AI, decentralization, and personal sovereignty. Anthony shares how he first discovered Bitcoin in 2012, bought in when it was under $10, and helped build the Toronto Bitcoin community where he eventually met Vitalik Buterin and became part of Ethereum’s founding story. The conversation moves beyond crypto into Anthony’s deeper mission: helping people regain control of their digital lives. He explains why Ethereum’s real breakthrough was not speculation, but utility, smart contracts, programmable systems, and the removal of unnecessary middlemen. Anthony also shares why he believes too much of today’s digital infrastructure depends on centralized platforms, cloud providers, and business models that extract value from users instead of empowering them. Jess and Anthony dive into his newest work around AI, cognitive sovereignty, and what it could mean for one person or a tiny team to accomplish what used to require hundreds of people. Anthony introduces the ideas behind As You Wish, his AI command platform built around “genies,” and Andiami, his effort to give people tools to run their own nodes, own their data, and reduce reliance on big tech infrastructure. This episode is a fascinating look at the next chapter of decentralization, where crypto, AI, personal computing, and human freedom all collide. If you care about the future of entrepreneurship, digital ownership, or staying in control of your own intelligence in an AI-driven world, this conversation is one to watch. Learn more about your ad choices. Visit megaphone.fm/adchoices

    56 min
  3. Jun 4

    $2.5B in Real Estate to Fulfillionaire | Thrive CEO JP Newman

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with JP Newman, CEO of Thrive FP and founder of Fulfillionaire, for a powerful conversation about success, money, meaning, and what happens after you finally achieve the life you thought would make you happy. JP shares his unconventional path from Sony Pictures and family entertainment to building a real estate platform with more than $2 billion in transactions, and how his early struggles shaped the way he thinks about leadership, risk, and responsibility. But the heart of this conversation goes far beyond real estate. JP opens up about what he calls “the net worth trap,” the shift from chasing money to fearing the loss of it, and why so many successful people still feel anxious, unfulfilled, or stuck after reaching major financial milestones. He explains the five dimensions of wealth behind Fulfillionaire, including prosperity, purpose, people, presence, and play, and why true wealth must support a life of meaning, connection, joy, and service. Jess and JP also explore philanthropy, faith, giving, and the responsibility that comes with managing other people’s money. JP shares the story behind Veritas Impact Partners, his nonprofit created to support residents in workforce housing communities with services like telemedicine, mental health support, financial education, and tutoring. This is a deeply human episode about redefining success, using money as a tool instead of a scoreboard, and building a life where wealth leads to freedom, generosity, and fulfillment. Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 2m
  4. May 21

    Why the Rich are Moving to the Cayman Islands? | Daniel Altneu & Co-hosted with Holly Parker

    In this special co-hosted episode of The Jess Larsen Show on Innovation & Leadership, Jess Larsen is joined by top Compass broker Holly Parker for a fascinating conversation with Cayman Islands attorney Daniel Altneu of Bedell Cristin. Together, they unpack why the Cayman Islands has become one of the world’s most sought-after destinations for ultra-high-net-worth individuals, family offices, entrepreneurs, and global investors. Daniel breaks down the realities behind Cayman residency, offshore structuring, wealth migration, tax strategy, and succession planning — while separating fact from Hollywood fiction about the islands. The discussion explores why affluent families from the U.S., Canada, the U.K., Dubai, and beyond are increasingly relocating assets, businesses, and even future generations to Cayman for lifestyle, privacy, safety, and long-term financial planning. Jess and Holly also dive into the cultural transformation happening in Cayman: world-class dining, luxury real estate, understated wealth, elite healthcare, international schools, and a growing reputation as a discreet alternative to places like Monaco, Dubai, and St. Barts. Along the way, they discuss family office trends, crypto migration, global mobility, co-ownership luxury properties, and what the future of wealth movement may look like in a rapidly changing world. Whether you’re curious about international residency, wealth preservation, offshore law, or simply why so many influential people are quietly choosing Cayman, this episode offers an insider look at one of the world’s fastest-growing hubs for global wealth and lifestyle. Learn more about your ad choices. Visit megaphone.fm/adchoices

    49 min
4.6
out of 5
304 Ratings

About

Jess Larsen interviews exciting people and uncommonly high achievers including Billionaires, Pro Athletes, Fortune 500 CEOs, Hollywood Actors like Danny Glover, New York Times Bestselling Authors, Tech Founders, Four-star Generals, World Class Musicians, Special Ops, VCs, Olympic Athletes, Non-Profit Leaders, Inventors and many more.

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