50 Chairs: Overnight Success is a Long Story — with Gary Hensley

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. N...

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...

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...

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...

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, bu...

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 see...

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 s...

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...

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 comp...

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 fram...

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 ho...

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 th...

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 upc...