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. 5d ago

    Investing in the Future of AI CyberSercurity | Andrew Rubin, Illumio Founder & CEO

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Andrew Rubin, founder and CEO of Illumio, for a timely conversation on cybersecurity, AI, investing, and what leaders need to understand about risk in a world where attacks are becoming faster, cheaper, and more sophisticated. Andrew explains the core philosophy behind Illumio: cybersecurity can no longer be only about preventing every breach. Companies still need to stop as much as they can, but they also need a second mission, containing attacks the moment they happen so one breach does not become a full-scale catastrophe. As Andrew puts it, the goal is to make the problem small before it spreads. Jess and Andrew also talk through what this means for founders, CEOs, and investors who may not have large security teams but still hold valuable customer data. Andrew breaks down why smaller companies can still be major targets, how AI is democratizing attack capabilities, and why leaders need to think seriously about partners, risk, reputation, and customer trust before a crisis hits. The conversation also moves into product-market fit, customer feedback, capital allocation, and investment philosophy. Andrew shares how Illumio thinks about building in a fast-changing market, why customer conversations matter more than surface-level feedback, and how he evaluates companies by looking at the market, the idea, the team, and their ability to execute over time. This is a sharp and practical episode about cybersecurity in the age of AI, the importance of moving faster without chasing perfection, and how leaders can make better decisions when the stakes are high and the timeline is shrinking. Learn more about your ad choices. Visit megaphone.fm/adchoices

  2. Aug 14

    How did He Grow to $6.4B | Tom Shea, Co-Founder & CEO of Onestream

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Tom Shea, co-founder and CEO of OneStream, for a deep conversation on building a multibillion-dollar software company, going from private to public and back to private, and what it really takes to create lasting enterprise value. Tom shares the journey behind OneStream, from his early days building software for the office of the CFO to creating a unified platform for consolidation, planning, reporting, and financial data. He explains how his first company, UpStream, led to an acquisition by Oracle, and how that experience gave him the confidence to think bigger, build a platform, and create a company that could serve some of the largest and most demanding organizations in the world. Jess and Tom dive into the principles that shaped OneStream’s growth, including the company’s simple but powerful mission: every customer must be a reference. Tom explains why customer success, product-market fit, transparency, passion, authenticity, and long-term relationships became the foundation of the business, especially when selling mission-critical software to CFOs whose numbers ultimately go to Wall Street. They also discuss the realities of entrepreneurship, from surviving early implementations and coding through hard problems to leading with confidence when things get difficult. Tom shares why founders must know their strengths, surround themselves with the right partners, stay close to customers, and build a culture where the team is willing to do whatever it takes to deliver. This is a practical and thoughtful conversation about scaling a software company, building trust with enterprise customers, navigating public and private markets, and creating a business where customer success is not a slogan, but the operating system. Learn more about your ad choices. Visit megaphone.fm/adchoices

  3. Aug 6

    Fomer Undercover CIA Officer Rescuing Children | Founder and President, ARC

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Bazzel Baz, a former Marine Corps officer, former CIA Ground Branch operator, author, actor, filmmaker, and founder of the Association for the Recovery of Children. Bazzel shares his extraordinary path from the Marine Corps and counterterrorism work after the Beirut barracks bombing to his time in the intelligence community, where he served during some of the most consequential conflicts of the Cold War era. He reflects on the lessons he learned from quiet professionals, the importance of humility, and why real service often happens without applause or recognition. Jess and Bazzel also explore his unexpected move into Hollywood, including his work on The Blacklist and the story behind Hotel Tehran, a film connected to a real-life intelligence story involving hidden money in Iran. But the heart of this conversation is Bazzel’s mission through ARC, the Association for the Recovery of Children, where he has spent decades helping recover missing, exploited, and trafficked children. This episode is a powerful conversation about courage, faith, service, leadership, child rescue, and what it means to dedicate your life to the people most others are too afraid to go after. Bazzel’s message is simple but unforgettable: saving one child may not change the whole world, but for that one child, their entire world changes. Learn more about your ad choices. Visit megaphone.fm/adchoices

  4. Jul 30

    Building One of America’s Largest Private Investment Platforms | 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

  5. 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

  6. 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

  7. 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

  8. 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

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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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