Going Big! with Kevin Gentry

What does it take to build something everyone else says is impossible?

In this episode of Going Big!, host Kevin Gentry sits down with author and journalist Josh Dean to explore the remarkable story of Clarence “Kelly” Johnson, the legendary Lockheed engineer who created the Skunk Works and helped produce some of the most consequential aircraft of the 20th century.

Johnson promised to build America’s first jet fighter in 180 days and delivered it in 143. He later led the development of the U-2 and SR-71 Blackbird, transforming aviation and providing the United States with critical intelligence capabilities during the Cold War. Dean explains how Johnson combined audacious goals with disciplined execution: exceptional talent, extreme focus, minimal bureaucracy, delegated authority, and a willingness to challenge conventional thinking.

The conversation offers lessons far beyond aerospace. For anyone leading a business, nonprofit, creative organization, or ambitious project, Johnson’s story raises a fundamental question: How do you create a culture capable of doing things others believe cannot be done?

What happens when you have a big idea but no funding, no guaranteed audience, and no finished plan?

Armin Petschner-Multari decided to find out. He committed to building what became the Berlin Campaign Conference, an international gathering where political strategists, communicators, and campaign leaders from democracies around the world exchange ideas, compare campaign practices, and build lasting relationships.

In this episode of Going Big!, host Kevin Gentry talks with Armin about taking that initial risk, the power of networks, the differences he sees between Anglo-Saxon and continental European campaigning, and the challenge facing traditional political parties as voters increasingly look for alternatives. The conversation also explores what it takes to build something consequential before you know exactly how it will work.

What does it take to build an exceptional craft from the ground up? 

 

In this episode of Going Big!, host Kevin Gentry sits down with Josh Grainer, inaugural winemaker at Lost Mountain Vineyards in Delaplane, Virginia, to explore the unlikely journey that led him into winemaking and the vision behind one of Virginia’s most serious wine projects.

 

Josh traces his path from growing up around agriculture and studying ecology to a transformative spring break trip to Tuscany, working in restaurant kitchens, and eventually apprenticing under legendary Virginia winemaker Jim Law. He shares how persistence opened a door that initially seemed closed, and how an unexpected opportunity at a young age led him to Lost Mountain.

 

The conversation goes deeper into the philosophy of craftsmanship, mentorship, risk-taking, and building something exceptional in an unlikely place. At Lost Mountain, a hillside once considered unsuitable for agriculture because of its rocky soil became the foundation for a distinctive approach to Virginia wine. Josh’s story offers lessons for anyone trying to discover their contribution, take a meaningful risk, and spend a lifetime getting better at their craft.

What happens when parents have the resources to choose the education that best fits their child?

In this episode of Going Big!, host Kevin Gentry sits down with Darla Romfo, president and CEO of Children’s Scholarship Fund, an organization that has awarded more than $1.2 billion in scholarships to nearly a quarter of a million children across America. Darla shares the story behind CSF, the vision of founders John Walton and Ted Forstmann, and why she believes families should be at the center of educational decision-making.

The conversation also explores the major new opportunity created by the upcoming federal tax credit for scholarship funding, which takes effect in 2027. Darla explains how the policy could expand access to educational choice, bring new donors into philanthropy, and create an unprecedented opportunity to scale scholarship programs across the country. She also shares lessons from more than two decades of leading CSF about parents, philanthropy, leadership, and preparing for a moment of enormous growth.

For those interested in education, school choice, philanthropy, nonprofit leadership, or the future of opportunity for children and families, this conversation offers a firsthand look at what it takes to build a movement, scale a proven model, and prepare for a potentially transformative moment.

How much of your day is consumed by work that no longer needs to exist?

In this episode of Going Big!, host Kevin Gentry sits down with Mike Allen, one of America’s most influential political journalists and the co-founder of Axios, to explore the hidden cost of complexity and how leaders can reclaim time for the work that matters most.

Mike traces his journey from traditional newspaper journalism to Politico, where he helped create Playbook, and then to Axios, where he helped pioneer Smart Brevity. Now, in his new book Simplify—which you can get at smartbrevity.com/simplify —Mike and his co-authors apply those lessons to organizations and everyday life. The three-part framework is simple: confront what has accumulated, delete what doesn't add value, and amplify the work that people are uniquely good at.

The conversation explores AI, information overload, storytelling, organizational bloat, meetings, leadership, and the discipline required to say no. Mike shares a striking example from Goldman Sachs, where simplifying work gave one team 500 additional hours each year. 

For anyone interested in learning more about how to simply their work and their life, this episode offers a practical challenge to become more productive without simply doing more. And if you enjoyed the conversation, please subscribe to Going Big!, leave a review, and share this episode with someone who could use some hours back in their day.