Advertise on podcast: The Jess Larsen Show on Innovation & Leadership

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

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

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

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

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

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

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

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