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. 3d ago

    From Microsoft To CEO Of $4B Life360 | Lauren Antonoff, Life360

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Lauren Antonoff, CEO of Life360, to talk about leading a roughly $4 billion technology company through its next stage of growth, expanding from family location sharing into a broader platform for keeping people, pets, and things connected. Lauren shares how her career at Microsoft, GoDaddy, and other major technology companies shaped the way she thinks about product, leadership, and customer experience. She also opens up about the transition from founder Chris Hulls to her taking over as CEO, why the process took years of working together, and what founders should consider when choosing someone to lead the company they built. They explore Life360’s growth beyond 100 million users, the company’s investments in pets and aging parents, and how Lauren decides where to allocate capital when there are more opportunities than resources. She explains why some of the biggest opportunities require investing years before the payoff is obvious and why understanding the real behavior of customers matters more than simply responding to feature requests. Jess and Lauren also dive into what it means to become an AI-native company. Lauren shares how Life360 is building AI into both its internal workforce and its products, including a future where technology can better understand family routines, reduce everyday friction, and help people stay connected without keeping them trapped inside an app. The conversation ultimately comes back to one of Lauren’s core beliefs: customer love is one of the strongest competitive advantages a company can build. From product development and M&A to freemium business models and long-term investing, Lauren explains why companies that genuinely understand and serve their customers can create value that is incredibly difficult for competitors to replicate. This episode is a deep conversation about product strategy, AI, leadership transitions, capital allocation, customer obsession, M&A, and building technology that becomes part of people’s everyday lives. Learn more about your ad choices. Visit megaphone.fm/adchoices

  2. Sep 24

    Re-engineering a $4 billion company for the age of AI | Linda Tong, CEO at Weblow

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Linda Tong of Webflow to talk about what it takes to reinvent a $4 billion technology company in the middle of the AI revolution. Webflow helped democratize building for the web, but as AI makes it easier than ever to create websites, apps, content, and digital products, Linda argues that simply being able to build is no longer the advantage. The real differentiators are taste, craft, usefulness, and whether what you create actually solves a meaningful problem. Linda breaks down how Webflow is evolving from a website-building platform into a broader digital experience and growth platform, helping teams improve discovery, SEO, conversion, experimentation, and optimization after a site goes live. She explains how AI can continuously test content, improve customer journeys, surface recommendations, and eventually help businesses create ongoing loops of improvement rather than treating a website as something that is simply built once and published. Jess and Linda also go deep on product leadership and the danger of building more simply because AI makes it possible. Linda shares lessons from her time at the NFL, including how removing thousands of pages and features from its mobile experience ultimately drove stronger engagement and better ratings. Her philosophy is simple: more features do not automatically create a better product. Great product leadership often means deciding what not to build and focusing intensely on the few things customers actually value. The conversation also covers leading through disruption, managing a distributed company, simplifying complex enterprise software, and navigating bias as a leader. Linda closes with her view of the next waves of AI, moving from helping people create, to helping them make what they create matter, and eventually toward systems that can continuously improve and innovate alongside us. This episode is a sharp conversation about AI, product strategy, innovation, leadership, Webflow, digital growth, and what it takes to build something people actually want in a world where creating is becoming nearly effortless. Learn more about your ad choices. Visit megaphone.fm/adchoices

  3. Sep 17

    Infiltrating Biker Gangs & Cartels for the CIA | Matthew Hedger

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Matthew Hedger, a former CIA non-official cover officer, for a rare conversation on undercover work, criminal cover, money laundering, cartels, outlaw motorcycle gangs, and the psychology of trust. Matthew explains what it really means to operate without diplomatic cover, why non-official cover is so different from the spy stories most people see in movies, and how his work eventually led him into criminal environments where he had to build credibility with people who could not afford to trust the wrong person. Jess and Matthew also dig into the art of rapport, and why trust is not just a soft skill, but a life-or-death capability in undercover work. Matthew shares how he built relationships inside dangerous organizations, why pretending to be tough was less useful than actually caring about people, and how reputation, emotional control, humor, and self-awareness can change the outcome of tense situations. The conversation goes deeper into the moral complexity of operating in gray areas, including moments where Matthew had to manage his own emotions, predict dangerous behavior, and decide where the line was between preserving an operation and intervening in the moment. This episode is a fascinating look at espionage, organized crime, human behavior, and leadership under pressure. It is also a powerful reminder that whether you are working undercover, leading a company, negotiating a deal, or trying to understand people better, trust is built through attention, humility, and genuine human connection. Learn more about your ad choices. Visit megaphone.fm/adchoices

  4. Sep 3

    How Did He Grow to $18B | Seth Streeter, Co-Founder of Mission Wealth

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Seth Streeter, Co-Founder of Mission Wealth, for a conversation about building an $18B wealth management firm, redefining what true wealth means, and helping successful leaders design a more fulfilling next chapter. Seth shares how he and his co-founder started with zero assets under management and built Mission Wealth around independence, objectivity, comprehensive financial planning, and a proactive service model. Instead of simply managing investments, Seth explains how the firm focused on understanding the whole client, including their business, family, taxes, estate planning, real estate, lifestyle, and long-term goals. Jess and Seth also dig into the growth journey from $1B to $18B, including the power of partnerships, referral channels, customer experience, company culture, and learning how to get out of your own way as a founder. Seth explains why saying no can be more important than saying yes, how service businesses can scale without losing their human touch, and why taking care of your team becomes a competitive advantage. The conversation then turns to Seth’s deeper mission: helping high-achieving CEOs, founders, and leaders find purpose beyond financial success. After his own personal journey through burnout, divorce, the financial crisis, and a search for deeper meaning, Seth began helping others explore what comes after achievement, from relationships and adventure to creativity, service, and legacy. This episode is a thoughtful look at wealth, leadership, service, purpose, and what it really means to build a life that feels successful from the inside out. Learn more about your ad choices. Visit megaphone.fm/adchoices

  5. Aug 28

    How Did He Build A $1.5B Licensing Portfolio | Sam Bremner

    In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Sam Bremner for a fascinating conversation on licensing, private equity, brand psychology, and the hidden business model behind some of the world’s most powerful intellectual property. Sam breaks down why licensing should not be treated as a side project or simple marketing play, but as a serious engine for low-capital, high-margin growth. From Harry Potter and Marvel to Care Bears, Starbucks, branded real estate, and luxury experiences, Sam explains how the smartest companies turn intellectual property, nostalgia, identity, and emotional connection into billion-dollar businesses. Jess and Sam also explore the rise of branded real estate, why consumers pay premiums for authenticity and experience, and how companies can use licensing to expand without taking on all the risk of manufacturing, inventory, shipping, or retail execution. Sam shares how Care Bears continues to connect with audiences through love, caring, sharing, nostalgia, collaborations, and global licensing partnerships. The conversation also goes deeper into leadership, ownership, private equity, and why Sam believes the best investors and operators understand both numbers and human behavior. He explains why people are predictable, why brands operate like relationships, and why the future belongs to leaders who can recognize patterns, move fast, and connect capital with emotion. This episode is a sharp look at how licensing really works, why feelings drive purchasing decisions, and how founders, investors, and brand builders can monetize identity, authenticity, and culture in ways most businesses completely overlook. Learn more about your ad choices. Visit megaphone.fm/adchoices

  6. Aug 20

    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

  7. 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

  8. 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

See All (1.1K)

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.

Information

You Might Also Like