The Jess Larsen Show on Innovation & Leadership

Graystoke Networks
  • 4.6 (304)
  • Entrepreneurship
  • Updated Daily

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

    $5B Crowdfunding Success Story | Ben Miller, Co-Founder & CEO of Fundrise

    This is for Ben Miller, founder of Fundrise, and the strongest angle is how Fundrise built a platform that opened private markets to everyday investors, reaching 2M+ investors and managing billions across real estate, credit, and venture/private tech. In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Ben Miller, founder of Fundrise, for a deep conversation on private markets, real estate, venture investing, and what it really takes to build a platform that gives everyday investors access to opportunities once reserved for institutions. Ben shares the story behind Fundrise’s mission to democratize private markets, how the company grew to more than 2 million investors, and why building this kind of business required far more than a clever fintech idea. From real estate and private credit to venture capital and AI companies like OpenAI, Anthropic, Databricks, and Canva, Ben explains how Fundrise evolved into a multi-asset platform built for long-term access and scale. Jess and Ben also explore the painful reality behind compounding success. Ben talks about regulation, fundraising, public offerings, investor education, criticism, persistence, and why most people underestimate how much suffering and repetition it takes to build something that lasts. This is a sharp, honest conversation about democratizing investing, surviving the long game, finding opportunities across cycles, and building a private markets platform in a world being reshaped by AI, technology, and constant change. Learn more about your ad choices. Visit megaphone.fm/adchoices

  2. Jul 23

    A $2.5B AI IT Success Story | Freshworks CEO Dennis Woodside

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Dennis Woodside, CEO of Freshworks, the $2.5B public software company helping IT and customer support teams use AI to work faster, smarter, and more efficiently. Dennis shares how Freshworks serves more than 75,000 companies around the world, including major names across technology, sports, education, entertainment, manufacturing, and enterprise software. Dennis breaks down how AI is transforming the way companies operate, from freeing creative teams from administrative work to helping IT departments automate repetitive requests and focus on higher-value projects. He explains why the next wave of enterprise software will be defined by speed, simplicity, and the ability to help teams adapt without needing months of custom implementation. Jess and Dennis also dive into what it takes to lead a founder-built company through major transitions. Dennis shares lessons from his time at Google, Motorola, Dropbox, Impossible Foods, and Freshworks, including how founders can successfully hand off the CEO role, how public companies can maintain long-term ambition, and why profitability, focus, and discipline matter more than ever in today’s SaaS market. This conversation is a practical look at AI, enterprise software, founder transitions, public company leadership, and how Freshworks is building AI-powered service software for the agile enterprise. If you care about SaaS, scaling, leadership, AI adoption, or the future of IT, this episode is one to watch. Learn more about your ad choices. Visit megaphone.fm/adchoices

  3. Jul 16

    Billion Dollar Success To Robotic Frontier | Lucas Ngoo, Cortex AI Founder

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Lucas Ngoo, CEO of Cortex AI and co-founder of Carousell, the Southeast Asian marketplace that grew to a $1 billion valuation. Lucas explains why the next major leap in AI may not just be chatbots or software, but general-purpose robotics. While robot hardware is getting cheaper and more powerful, Lucas argues that the biggest bottleneck is still data: the real-world human and robot data needed to train machines to operate safely, precisely, and intelligently in everyday environments. Jess and Lucas dive into how Cortex AI is building the data infrastructure for robot brains, collecting human task data from industries like factories, retail, restaurants, hotels, and other real-world environments. They also explore why robots may follow a path similar to Waymo, starting with human supervision and gradually improving until autonomy becomes invisible and widespread. Lucas also shares the lessons he learned from building Carousell from three founders out of school into a billion-dollar company, including how to hire during rapid growth, survive startup chaos, raise capital, choose the right investors, and recognize technologies that are just becoming possible. This is a forward-looking conversation about robotics, AI, entrepreneurship, Silicon Valley ambition, and what it really takes to build the future before the rest of the world sees it coming. Learn more about your ad choices. Visit megaphone.fm/adchoices

  4. Jul 10

    What Attributes Create SEAL Teams 6 Excellence? | Rich Diviney, Retired Navy SEAL Commander

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Rich Diviney, retired Navy SEAL, former SEAL Team Six operator, founder of The Attributes Training Company, and author of The Attributes and Masters of Uncertainty. Rich breaks down the difference between skills and attributes, and why elite performance is not just about what someone knows how to do, but whether they have the internal wiring to perform when pressure, chaos, and uncertainty hit. Drawing from his experience running selection at SEAL Team Six, Rich explains why some of the most talented operators still do not make it through, and what separates those who can adapt, recover, learn, and execute under extreme conditions. Jess and Rich also explore the psychology of high-performing teams, the difference between elite and special, how SEAL Team Six and Delta Force approach selection differently, and why attributes like learnability, resilience, compartmentalization, empathy, caring, discipline, and task switching shape performance in every field, not just the military. This is a fascinating conversation about leadership, human potential, uncertainty, and how to understand yourself and your team at the deepest level. Whether you are building a company, leading people, developing talent, or trying to perform better under pressure, Rich offers a powerful framework for knowing where you are a rock star, where you are a doofus, and how to build the right team around you. Learn more about your ad choices. Visit megaphone.fm/adchoices

  5. Jul 2

    Winning Philosophy of a Billion Dollar Vacation CO | James Henderson, CEO of Exclusive Resorts

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with James Henderson, CEO of Exclusive Resorts and The Exclusive Collective, for a fascinating conversation on the future of luxury travel, community, and what it really means to live well. James shares how Exclusive Resorts evolved from a destination club into a luxury lifestyle platform with more than $1 billion in real estate, hundreds of residences, once-in-a-lifetime trips, and a growing family of brands designed to serve affluent travelers in different ways. From private homes and curated villas to Formula One, the Kentucky Derby, Antarctica, around-the-world jet trips, and exclusive member experiences, James explains why today’s most successful people are increasingly choosing memories, relationships, and seamless service over material status. Jess and James also explore the rise of the experience economy, the power of community among high-net-worth families, and why the best luxury experiences are often defined by what you do not have to think about. James breaks down how his team uses personalization, human touch, brand architecture, and operational discipline to create travel that feels effortless while still deeply personal. This conversation is about more than luxury vacations. It is about time, connection, family, leadership, and building a business around the idea that people may be able to make more money, but they cannot make more time. Learn more about your ad choices. Visit megaphone.fm/adchoices

  6. Jun 25

    How Did He Grow to 2 Million Customers? | KOHO Co-Founder and CEO, Daniel Eberhard

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Dan Eberhard, Founder & CEO of Koho, one of Canada’s most exciting fintech companies. Dan shares how Koho grew from a scrappy idea challenging Canada’s powerful banking system into a company with 2 million customers, hundreds of millions raised, and a real shot at building the next great bank in Canada. Dan opens up about his unconventional path from growing up in a small mountain town in British Columbia to building wind farms, selling his first company, and eventually launching Koho after seeing how much wealth traditional financial products were extracting from everyday Canadians. Jess and Dan dive into the realities of building a fintech company in a market dominated by major banks, including the early grind of raising money, convincing partners like Visa and People’s Trust, nearly running out of cash, and moving the company to Toronto after an investor ultimatum. Dan also breaks down how Koho thinks about product-market fit, customer behavior, fundraising, leadership, and building through chaos. This is a powerful conversation about entrepreneurship, financial freedom, resilience, and what it really takes to build a company that can challenge an entrenched industry. Learn more about your ad choices. Visit megaphone.fm/adchoices

  7. Jun 18

    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

  8. 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

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4.6
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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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