The Jess Larsen Show on Innovation & Leadership

In this episode of The Jess Larsen Show on Innovation & Leadership, Jess is joined by former CIA officer Matthew Hedger to sit down with Jay Flores, a former major drug trafficker whose extraordinary story took him from working alongside some of the most powerful figures connected to the Sinaloa Cartel to cooperating with U.S. law enforcement and helping expose how the organization actually worked from the inside. Jay entered the drug trade at a young age and eventually operated at an international level, moving enormous quantities of cocaine through North America and sending billions of dollars in bulk cash back toward Mexico. At the height of that operation, Jay and his brother made the decision to change course. They approached U.S. authorities, spent months conducting dangerous undercover work, provided intelligence that contributed to major cases against the Sinaloa Cartel, and ultimately served lengthy prison sentences for their own crimes. Today, Jay has dedicated much of his life to helping law enforcement understand organized crime through the eyes of someone who actually operated inside it. His central argument is that governments have spent decades fighting a war on drugs when they should be fighting a war on the business of drugs. Jay challenges many of the assumptions popularized by movies and television about how cartels operate. Rather than a single pyramid controlled by one all-powerful kingpin, he describes a network of independent organizations, transportation providers, distributors, money movers, corrupt officials, and other specialists working together because their financial interests align. Removing one leader does not necessarily destroy the system when the underlying business continues functioning. Jess, Matthew, and Jay dig into the economics behind that system, including why restricting the drug supply can sometimes increase profits, how products move through different layers of the supply chain, and why Jay believes law enforcement should focus much more aggressively on the money flowing back through criminal organizations. Jay describes moving millions of dollars in bulk currency at a time and explains why disrupting those profits can create far greater consequences than simply seizing another shipment of drugs. The conversation also explores the importance of human intelligence, informants, relationships, and continuous innovation. Jay explains how criminal organizations constantly studied law enforcement tactics, learned from mistakes, adapted their systems, and shared knowledge to stay ahead. He argues that law enforcement needs the same culture of learning, collaboration, and adaptation if it wants to effectively combat modern organized crime. Jay also opens up about redemption, the consequences of the life he once lived, losing family members to drugs, and why he now believes his experience can serve a different purpose. The discussion ultimately expands beyond narcotics into human trafficking, child exploitation, prevention, and how understanding the economics and incentives behind criminal organizations may provide a better path toward dismantling them. This episode offers a rare look inside the Sinaloa Cartel, El Chapo's criminal network, international drug trafficking, bulk cash smuggling, undercover cooperation, organized crime, law enforcement strategy, human intelligence, redemption, and the business systems that allow criminal organizations to survive long after individual leaders are gone. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Ryan Freedman, co-founder and chairman at Alpaca, to explore the intersection of artificial intelligence, venture capital, real estate, and investing during one of the most unusual market environments in recent memory. Ryan has spent his career across real estate development, asset management, and venture capital, with teams involved in billions of dollars of transactions. Today, he is focused on building an AI-native approach to asset management and using technology to improve how investment firms research opportunities, evaluate risk, and make decisions. Jess and Ryan discuss what higher interest rates could mean for real estate, why distress may continue emerging as loans mature, and where Ryan is still finding opportunities. He breaks down his thesis around build-to-rent housing, infill industrial real estate, luxury residential markets, and why certain markets continue to stand out despite broader uncertainty. They also explore one of Ryan’s most important investing principles: liquidity creates optionality. When markets become dislocated and other investors are forced to sell or cannot access capital, having cash available can create opportunities that simply do not exist during periods of optimism and easy money. The conversation then moves into how Ryan is using AI inside his investment organizations. His team is building systems that can analyze research from across the market, preserve institutional knowledge, track previous investment decisions, and compare assumptions against what actually happened. Rather than replacing investor judgment, Ryan sees AI as a way to help firms ask better questions, identify patterns, and become more intellectually honest about their decisions. Ryan also explains why some of the greatest opportunities come from combining an existing area of expertise with a rapidly emerging technology. His background is real estate, but his growing knowledge of AI creates a new intersection where relatively few people have deep expertise in both. He believes entrepreneurs across virtually every industry have a similar opportunity to rebuild old businesses with better technology, better margins, and better decision-making. Jess and Ryan also discuss emotional discipline, conviction, staying liquid, separating signal from noise, and why being early to a major trend can look almost identical to being wrong. This episode is a wide-ranging conversation about real estate investing, artificial intelligence, venture capital, market cycles, capital allocation, decision-making, liquidity, entrepreneurship, and finding opportunities before the rest of the market recognizes them. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Dr. Stephen Hammond, physician, entrepreneur, and co-owner of Waccamaw Dermatology, to explore how he helped build a rapidly growing dermatology organization serving roughly 200,000 patients a year. Stephen shares how the company grew from seeing around 20 patients a day to building a vertically integrated healthcare platform that combines medical dermatology, surgery, pathology, cancer treatment, clinical research, aesthetics, and other services under one roof. He explains why bringing more of the patient journey in-house has allowed the organization to improve communication, reduce friction, and deliver better care while continuing to scale. Jess and Stephen also dive into how artificial intelligence is beginning to transform healthcare. Rather than relying entirely on outside vendors, Stephen’s team is developing AI capabilities internally using its own clinical data. He discusses where AI can improve efficiency, reduce errors, and support physicians, while also explaining why medicine still requires human judgment when multiple data points have to be combined into a real treatment decision. The conversation goes beyond healthcare into entrepreneurship and leadership. Stephen explains why physicians are often trained to avoid risk, how he learned to reinterpret that risk when becoming an entrepreneur, and why having a strong professional safety net can actually make it easier to take ambitious bets. Stephen also breaks down the strategy behind vertical integration, including why entrepreneurs should often partner with experts before bringing a new capability in-house. He shares how to recognize the right inflection point for expansion and why taking on a new revenue stream also means taking on the complexity required to operate it well. Jess and Stephen close with a deeper discussion about culture, confidence, and leadership. Stephen shares his philosophy of making every employee responsible for the person immediately before and after them in the service chain, creating stronger accountability and teamwork as the organization approaches 300 employees. He also explains why great leaders lower the temperature during difficult moments, remain accessible, and help people build confidence by first giving them opportunities to succeed. This episode is a wide-ranging conversation about healthcare entrepreneurship, AI in medicine, scaling a medical business, vertical integration, leadership, company culture, risk, and building an organization around both operational excellence and patient care. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Will Wang, Founder and CEO of Even Realities, the smart glasses company that recently raised $150 million at a $1 billion valuation. Will shares how his experience working at Apple on the Apple Watch helped shape his belief that smart glasses could become the next major evolution in wearable technology. But after looking at the products already on the market, he saw a fundamental problem: most smart glasses felt like technology first and eyewear second. His goal with Even Realities was to build something people would actually want to wear every day, combining advanced technology with the design, comfort, and aesthetics of premium eyewear. Jess and Will explore what it takes to build a global hardware company from the ground up. Will explains why Even Realities built its engineering operation around Shenzhen, brought in experienced European eyewear designers, and developed sales and marketing teams across different markets rather than trying to build everything from a single technology hub. They also go deep on the economics and strategy of hardware startups, including how Will decides when to grow the team, how he thinks about product-market fit when every new hardware generation requires significant upfront investment, and why founders need to balance building for the future with staying financially grounded in the present. Will shares some of the lessons behind growing Even Realities from fewer than 30 employees to a global team of more than 300, including why vision and talent remain his two biggest priorities. He also reveals one of the moments that convinced him the company had created something special: after launching its first generation of smart glasses, competitors including Apple and Meta began purchasing dozens of pairs to study the product. The conversation also covers fundraising, hiring, supply chain complexity, product design, competing against technology giants, and what investors should look for before backing a hardware startup. Will explains why great hardware requires much more than an innovative prototype, and why years of experience managing suppliers, manufacturing, and global teams can become an enormous competitive advantage. This episode is a deep dive into smart glasses, wearable technology, hardware entrepreneurship, product-market fit, fundraising, global teams, supply chains, and what it takes to build a billion-dollar company while competing with some of the biggest technology companies in the world. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Jillian Share, President of Teton Ridge Entertainment, for a conversation about Hollywood, the future of film and television, and why Western and heartland stories may represent one of the biggest underserved opportunities in entertainment. Jillian shares the path that took her from early days at Legendary Entertainment to working across major film and television projects, including Pacific Rim, The Hangover, Dungeons & Dragons, Transformers, and more. She reflects on learning the business from the ground up, working alongside top filmmakers and producers, and what years inside major entertainment companies taught her about creative risk, production, and leadership. Today, at Teton Ridge Entertainment, Jillian is helping build a new generation of film, television, documentaries, and digital content rooted in the spirit of the American West. She explains why Western storytelling is much broader than cowboys and shootouts, and how themes like family, adventure, loyalty, land, and identity can resonate with audiences across the country. Jess and Jillian also discuss the enormous opportunity in serving audiences that Hollywood has often overlooked. From the success of country music and Western-inspired entertainment to projects like Lonesome Dove and Teton Ridge’s Lainey Wilson documentary, Jillian shares why people show up when they feel represented by the stories on screen. The conversation also dives into the business of entertainment, including how independent films are financed, what investors should understand before putting money into a movie, why a great script still matters more than almost anything else, and how filmmakers can improve their odds by thinking carefully about budget, distribution, talent, and audience before production begins. Jillian also shares her perspective on the constant disruption happening across Hollywood, from streaming and YouTube creators to new distribution models and AI. Her belief is that while the platforms will continue to change, one thing remains constant: people will always want great stories. This episode is a fascinating look at Hollywood, film investing, Western entertainment, storytelling, production, audience building, and the future of movies and television. Learn more about your ad choices. Visit megaphone.fm/adchoices

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

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

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

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

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