50 Chairs

What if intelligence tools once reserved for governments could help businesses, families, and everyday people make better decisions?In this episode of 50 Chairs, Gary Hensley talks with Anthony Vinci, CEO of Vico.io, former intelligence officer, and author of The Fourth Intelligence Revolution: The Future of Espionage and the Battle to Save America.Anthony shares how his experience in intelligence, including serving as CTO of the National Geospatial-Intelligence Agency, led him to build Vico, a platform designed to help people forecast future events and make more informed decisions.They discuss:What intelligence officers see that most people missHow misinformation and deception affect businesses, families, and votersWhy AI-generated content creates a new challenge for finding truthHow forecasting can improve decision-makingWhy intelligence is not just about gathering information, but helping people make better choicesThe courage it takes to leave a successful career and build something newAdvice for young people navigating AI and an uncertain futureAnthony also explains why he believes the future belongs to people who can think critically, test information, and take action before certainty arrives.Learn more about Anthony and Vico at https://vico.io  Follow Anthony at https://anthonyvinci.comSubscribe to 50 Chairs for conversations with founders, leaders, and builders navigating the moments that require conviction, courage, and a willingness to start before the path is clear.@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

Erica Donalds is an entrepreneur, education advocate, charter school founder, and former managing partner at a multi-billion-dollar fund. In this conversation, she shares the moment she walked away from a successful finance career to pursue education reform, why she believes parents should have more agency in their children’s schooling, and how charter schools, school choice, AI, and virtual reality are shaping the future of education.In this episode:Leaving finance to pursue education reformWhy school board service showed her the limits of the systemWhat she learned from launching charter schoolsHow parents can have more choice and ownershipWhy AI and virtual reality may change learningWhy entrepreneurship is essential to freedom and innovationListen on Apple Podcasts, Spotify, and YouTube.@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

Johnny Crowder built Cope Notes, an SMS-based mental health platform reaching people in 110 countries, without a paycheck for four and a half years. He did it coming off a career touring in a death metal band, without knowing venture capital was even an option, and without ever automating the human part of his product.This is a conversation about what it actually takes to stay. Not the highlight reel. The moment the bank calls because your account hit zero. The monthly urge every founder gets to walk away. The weight of knowing that when you are out, your employee is out too.Johnny is one of the most honest founders I have sat across from. He talks about bootstrapping as a blind spot, not a badge of honor. About redefining success so many times that the definition that finally stuck would drive an investor up a wall. And about a simple life mission that has never needed to change: make stuff that helps people feel better.If you are in the middle of a hard season and wondering whether the difficulty means you are doing it wrong, this one is for you.@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

Kevin Damoa started as a backup dancer in Los Angeles. Then he went to war.After serving in both the Army and Air National Guard, Kevin spent years at SpaceX, Northrop Grumman, and Harley-Davidson's Serial 1 Cycle Company. At every stop, he kept finding the same broken system hiding in the same place: the seam where road and rail are supposed to hand off to each other. Nobody had fixed it. Not the military. Not the biggest aerospace companies in the world. Not anyone.So Kevin built the fix himself.He's the Founder and CEO of Glīd Technologies, a dual-use logistics infrastructure company building road/rail autonomous vehicles and an AI coordination layer that works across commercial freight and contested defense environments. One system. Two very different threat environments. No new infrastructure required.In this episode, we go deep on the logistics gap that's been hiding in plain sight for decades, why the problem persisted, the grind of building hardware from scratch after leaving some of the most prestigious companies in America, and the moment Taylor Transport's president said he never conceived this technology would exist in his lifetime.Kevin's unfair advantage isn't the technology. It's the biography. Nobody else has the full map.Topics covered:Railhead operations in Iraq and the logistics flaw that wouldn't let him goBuilding dual-mode vehicles that operate on both road and standard-gauge railThe Glīd product suite: GlīderM, Rāden, and EZRA-1SIXDefense logistics, GPS-denied environments, and the dual-use visionWhat it takes to get your first customer when you're selling the future@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

He sold his company, sat in a rocking chair on his farm porch, and lasted about a week before asking himself: what now?Dr. Andy Hafer built Dynamic Communities over 15 years and sold it to private equity. In this episode, he tells Gary the unfiltered version of life at the "mountaintop," and why it's really a mountain range. He talks gratitude, the hand-written thank-you checks he sent his team, and how a kid who set out to be valedictorian became an accidental entrepreneur after hating his first engineering job.Andy ran his first company from behind the wheel of a 36-foot RV, wearing helicopter pilot headphones, while his family traveled the country. From there he co-founded Synapse and helped turn Tampa Bay into a place known for building companies, and now he's aiming the same playbook at the region's toughest societal challenges.What you'll hear:What surprised him most the day the deal closedWhy work ethic, not the grade itself, is the real through lineHow a software user group became a community of thousands"The most powerful force in the universe is people coming together to solve problems"His one-line advice for anyone sitting on an idea: just do itThe mentors who shaped him, from his parents to a civil rights marchWhat's next: Park Junction, an AI startup, and moving Tampa Bay's rankingsFind Dr. Andy Hafer on LinkedIn (search "Dr. Andy Hafer").50 Chairs is hosted by Gary Hensley. Listen on Apple Podcasts, Spotify, and YouTube. More at 50chairs.com.@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

In this episode of 50 Chairs, Gary sits down with Blake Hall, founder and CEO of ID.me, for a conversation about service, identity, leadership, and what happens when a startup grows into national infrastructure.Blake shares the origin story behind ID.me, from seeing veterans forced to expose personal information just to access simple benefits, to building a digital identity platform now trusted across major parts of government, healthcare, and commerce. He reflects on his time as an Army Ranger, the lessons of service, the loneliness of leadership, and the operational discipline required to scale through chaos.Gary and Blake also explore the future of AI, fraud, trust, and what it means to prove who you are in a world where technology is making everything easier to fake.For anyone building in the ugly middle, Blake’s advice is direct: develop a skill that matters, tie it to your superpower, build habits of excellence, and stop waiting.The future belongs to builders.www.50chairs.com@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

Donna Harris joins 50 Chairs to talk about the “middle” of entrepreneurship, the moment when the vision is clear but the chairs are still empty.From leaving corporate life at Oracle, to building her first company, co-founding 1776, and now leading Builders and Backers, Donna shares what it really takes to turn ideas into action. This episode explores agency, startup ecosystems, pitch competitions, family sacrifice, and why America needs more everyday builders.For anyone sitting on an idea and wondering where to start, Donna’s advice is simple: momentum beats perfection.@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

What happens when a West Point graduate, Army intelligence officer, startup founder, and venture capitalist realizes that success was never about the destination?In this episode of 50 Chairs, I sit down with my longtime friend and mentor, Craig Cummings, Co-Founder and General Partner at Moonshots Capital.Craig’s journey spans U.S. Military Academy at West Point, the National Security Agency, building and selling RideScout to Daimler Mercedes-Benz, and now investing in some of the country’s most ambitious founders across defense tech, AI, biotech, and national security.But this conversation goes deeper than resumes and exits.We talk about:Why “the climb is the joy”The loneliness of entrepreneurshipLeaving the military three years before retirementBuilding startups while facing personal adversityHow Moonshots evaluates founders and leadershipWhat authenticity actually means in leadershipThe emotional reality of acquisitionsWhy founders must know when to keep going and when to stopThe secret to “having it all”This is a conversation about ambition, identity, leadership, friendship, and learning to appreciate the journey before the summit.If you’re building something, questioning your next move, or chasing a version of success that still feels out of reach, this episode is for you.🎧 Listen on Spotify, Apple Podcasts, and YouTube 🌐 More episodes and founder playbooks at www.50chairs.com@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

He was cut 13 times, and still made the NFL. Most people quit long before that.In this episode of 50 Chairs, I sit down with former NFL fullback Jed Collins, whose journey is built on resilience, rejection, and relentless belief.This isn’t a highlight reel story. It’s about what happens before the success. When the chairs are still empty.We talk about:Building conviction when no one else sees itWhy greatness is lonelyThe mindset required to keep going through rejectionWhat the NFL teaches about pressure, identity, and disciplineHow Jed turned his journey into a mission around financial literacyJed also shares his framework for “being a pro”: confidence, trust, and adding value. Lessons that apply far beyond football.If you’re in the middle of building something and it’s not working yet… this one will hit.Because success isn’t instant. It’s built one chair at a time.@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

What does it actually take to stay in the game long enough to win?In this episode of 50 Chairs, Gary Hensley sits down with Alex Denning to explore the phase of building that most people never make it through. The part where nothing is working, no one is watching, and the outcome is still uncertain.From the discipline of Formula racing to competing at the highest levels with Lamborghini, Alex shares what it means to operate with conviction when there is no immediate signal.This conversation is about more than racing. It is about patience, belief, and the reality that success is often decided long before it is visible.If you are building something, this one is for you.https://50chairs.com/blog/8d40595f-9b46-4444-9bbf-c19908f915ef@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

What makes someone walk away from a “perfect” career?In this episode of 50 Chairs, Gary sits down with Becca Brown — Harvard graduate, Columbia MBA, and former Goldman Sachs professional, who made the leap into entrepreneurship to solve a problem most people would overlook.What started as a simple frustration turned into a real company, a Shark Tank deal, and a crash course in what it actually takes to build something from nothing.This conversation goes beyond the highlight reel.It’s about the tension, the doubt, and the conviction required to keep going when nothing is guaranteed.In this episode, we cover:• The moment Becca knew she had to leave Goldman Sachs• How small problems can become real businesses• What really happens behind the scenes of Shark Tank• Why authenticity is a founder’s greatest advantage• The importance of creating options, not chasing one outcomeThis is a story about seeing the empty chairs… and choosing to show up anyway.Link to playbook - https://50chairs.com/blog/cfbe8857-fbae-41b5-b559-ed5d52dc133c@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

What does it take to start a car company in today’s world?On this episode of 50 Chairs, Gary Hensley sits down with Mark Tapscott and Daniel Davey, two automotive leaders who helped shape the electric vehicle revolution inside companies like Tesla, Lucid, BYD, and Polestar.After years inside some of the world’s most influential EV companies, they made a bold decision: start their own.Their company, Longbow Motors, is on a mission to reinvent the lightweight electric sports car—built around driver experience, customer community, and a radically different approach to building vehicles.In this conversation, Gary, Mark, and Daniel explore:• Why the best founders see risk differently• What large companies often get wrong about listening to customers• The surprising lessons learned inside Tesla and the EV industry• Why community and storytelling matter as much as engineering• How co-founders survive the ups and downs of building something new• The mindset required to turn an idea into a real companyThey also dive into the origins of Longbow, the philosophy behind their 27 founding principles, and how they’re building a car company designed to last 100 years.This episode is a masterclass in entrepreneurship, conviction, and building something meaningful.If you’ve ever wondered what it takes to go from working inside great companies to starting your own, this conversation is for you.@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

In this episode of 50 Chairs, Gary Hensley sits down with Chris Stott, CEO of Lone Star Lunar, to discuss what it takes to turn a once-radical idea, storing data on the moon, into operational reality.Chris shares how listening deeply to customer pain around data sovereignty and security led him to develop space-based and lunar data centers. He explains the legal, regulatory, and geopolitical frameworks that make off-planet data storage viable and why understanding the “rules of the game” before playing is critical.The conversation explores:Building credibility as a young founderAttracting world-class partners through visionWorking with regulators as strategic alliesThe legal architecture of space sovereigntyRaising a child to pursue purpose over prestigeWhy we are entering an era of technological abundanceThis episode is about vision, courage, and building for a future most people can’t yet see.@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

In Episode 3 of 50 Chairs, Gary Hensley sits down with Lisa Sutton Gunderson to unpack a career defined by ambition, discipline, and reinvention—from law and business bankruptcy to building and exiting a successful bakery brand, competing in pageantry with a high-performance strategy, and ultimately joining The Veteran Fund as a GP through relentless conviction and values alignment. Lisa shares how high standards shaped her confidence, why studying failure patterns is a shortcut to smarter entrepreneurship, and how partnering with strong operators has enabled her to scale across industries while staying grounded in purpose.@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

In this episode of 50 Chairs, host Gary Hensley engages with Ryan Micheletti and Mike Sherbakov from the Veteran Fund, exploring the journey of building a community for veterans through entrepreneurship. They discuss the importance of integrity, conviction, and relationship-building in the investment process, as well as memorable pitches and the future of innovation. The conversation emphasizes the significance of supporting veteran-led startups and the unique qualities that veterans bring to the entrepreneurial landscape.TakeawaysThe Veteran Fund is a culmination of decades of work.Building a community of veterans is essential for success.Investing is a people business, focusing on relationships.Integrity is crucial when pitching to investors.Conviction and passion are key to inspiring others.Memorable pitches often come from founders with deep conviction.The future of innovation relies on supporting veteran-led startups.Clear and simple communication is vital in pitches.Building a tribe of like-minded individuals enhances success.The journey of entrepreneurship is often non-linear and requires resilience.Sound bites"It's important to build a relationship.""It's a people business.""You have to be very clear and simple."Chapters00:00 The Genesis of the Veteran Fund02:58 Building a Community and Ecosystem06:00 The Journey of Entrepreneurship08:52 Connecting the Dots: Military to Business11:57 The Unique Value of Veteran Leadership15:00 The Investor's Mindset17:54 Evaluating Founders and Startups20:56 The Role of Veterans in Innovation24:03 Navigating Challenges in the Tech Space27:04 Red Flags in Pitching29:49 The Long-Term Relationship Between Founders and Investors33:51 Navigating Rejection and Building Relationships36:10 The Importance of Consistency in Communication38:23 Identifying Key Traits in Founders40:06 The Intangible Qualities of Successful Founders42:20 The Role of Conviction in Entrepreneurship45:08 Inspiring the Next Generation of Innovators48:05 Memorable Pitches and Their Impact50:58 The Power of Conviction in Founders54:20 Inspiring Future Generations Through Innovation56:34 Crafting the Perfect Pitch for Investors@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com

In this conversation, Tucker Hamilton shares his remarkable journey from being a test pilot to leading the Air Force's AI initiatives. He discusses the importance of teamwork, resilience, and the role of AI in national security. Tucker reflects on his experiences in high-stakes environments, the challenges of leadership, and the future implications of AI technology. He also introduces his upcoming book, which aims to inspire others to unlock their potential through discipline and resilience.TakeawaysTucker Hamilton's journey reflects the importance of perseverance and adaptability.AI is a critical component of modern national security strategies.Effective teamwork relies on trust, integrity, and open communication.Resilience is a collective effort, not a solo endeavor.The rapid advancement of AI technology poses both opportunities and challenges for society.Leadership in high-stakes environments requires a disciplined and methodical approach.Failure can lead to significant learning and innovation.Tucker's experiences highlight the need for continuous learning and improvement.The future of AI will dramatically reshape various industries and job markets.Tucker's upcoming book aims to inspire others to reach their full potential.@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com