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Going Big! with Kevin Gentry: Daily Summaries Delivered
by Kevin Gentry
Welcome to Going Big! — the podcast where we share the stories of people who have truly gone big in their own lives. Hosted by Kevin Gentry, each episode features in-depth conversations with business owners, entrepreneurs, nonprofit leaders, political figures, and other trailblazers who have achieved extraordinary impact in their work and communities. You’ll hear firsthand how they pursued bold ideas, took major risks, overcame challenges, and built something remarkable. We no longer focus solely on fundraising and marketing. Instead, Going Big! explores the full spectrum of leadership, innovation, and personal drive — uncovering the lessons, values, and pivotal moments that propelled our guests to think bigger and push further. Whether you are an aspiring entrepreneur, a nonprofit leader, a political changemaker, or simply someone inspired by real stories of ambition and achievement, Going Big! offers insights and inspiration to help you take your own next leap.
Latest Episodes
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- Yesterday42 min
The Conference Guiding the Future of the Center-Right with Armin Petschner-Multari
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.
- 1 weeks ago50 min
How Josh Grainer Helped Put Virginia Wine on the Map (Lost Mountain Vineyards)
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.
- 2 weeks ago55 min
The Power of Parents in Education with Darla Romfo (Children's Scholarship Fund)
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.
- 3 weeks ago45 min
Simplify: Doing What Actually Matters with Axios co-founder Mike Allen
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.
- 4 weeks ago57 min
The Billion-Dollar Bet on Educational Opportunity with Tony de Nicola
What happens when a successful private-equity executive decides that one of America’s biggest challenges cannot be solved through philanthropy alone? In this episode of Going Big!, host Kevin Gentry sits down with Tony de Nicola, Chairman of Welsh, Carson, Anderson & Stowe and co-founder of Invest in Education, to explore his decade-long effort to expand educational opportunity for American families. Inspired by his own immigrant family’s experience and the education that changed the trajectory of his life, Tony became convinced that systemic reform was needed to help more children access the schools that best meet their needs. Tony shares the remarkable story of building bipartisan support for education tax-credit legislation in New York, watching it fail at the final stage two years in a row, and then making the decision to take the fight to Washington. That persistence ultimately helped lead to the first federal tax-credit scholarship program in American history, projected at roughly $30 billion over 10 years and potentially capable of supporting millions of scholarships. The conversation also explores Tony’s “venture philanthropy” approach, donor engagement, leadership, risk-taking, learning from failure, and what it takes to pursue a transformational goal over many years. For anyone interested in education, philanthropy, public policy, or pursuing meaningful change over the long term, this is a conversation worth hearing. Be sure to subscribe to Going Big! wherever you listen to podcasts, and share this episode with someone who is working to solve a problem that may be bigger than any one organization can tackle alone. To learn more about the new federal scholarship tax credit program, visit https://scholarshiptaxcredit.org/
- Aug 31, 202655 min
Agency: Why He Took a $25K Job With a Harvard MBA with Ian Rowe (American Enterprise Institute)
What if the obstacles standing in front of a young person do not have to determine the course of that person’s life? Ian Rowe, author and senior fellow at American Enterprise Institute, has spent three decades working across education, philanthropy, government, and the private sector trying to answer that question. In this episode of Going Big!, host Kevin Gentry sits down with Rowe to explore his concept of agency: the combination of free will and moral discernment that allows people to make choices about the lives they will build. Rowe shares the personal story that shaped his thinking, including the moment at age 12 when he challenged his parents’ decision about his school and the later decision to leave a conventional career path after Harvard Business School for a $25,000-a-year position at Teach for America. Rowe also explains the four institutions he believes are essential to cultivating agency in young people: family, religion, education, and entrepreneurship. He discusses Vertex Partnership Academies, the first graduating class from the school he co-founded, and his plans to build additional virtues-based schools that combine rigorous education with career preparation. Listen to the full episode of Going Big! to hear Ian’s story and consider how we can help young people recognize their own agency, overcome obstacles, and become the architects of their own lives.
- Aug 24, 20261h 43m
From Green Beret to Media Powerhouse with Nick Freitas
What if losing the biggest opportunity of your life was actually preparing you for something much bigger? In this episode of Going Big!, host Kevin Gentry sits down with Nick Freitas, an Army Green Beret, former Virginia legislator, two-time congressional candidate, and media entrepreneur whose platform now reaches millions of people. Nick shares the story behind his unconventional journey, from military service and public office to two painful electoral defeats and the unexpected media career that followed. The conversation explores faith, family, responsibility, overcoming adversity, military leadership, entrepreneurship, and the difference between measuring success by outcomes versus obedience. Nick also explains how the team he built through his political campaigns eventually helped launch a rapidly growing media operation, and why he chose to partner with Blaze Media while preserving his independence. For anyone who has experienced disappointment, questioned whether a setback had meaning, or wondered how to identify the next chapter of their life, Nick’s story offers a compelling perspective on what it means to keep going big when the original plan doesn’t work.
- Aug 17, 202656 min
Why Pennsylvania is the Key to Victory with Matt Brouillette (Commonwealth Partners)
What does it take to turn good ideas into lasting policy change? In this episode of Going Big!, host Kevin Gentry sits down with Matt Brouillette, longtime public policy leader and founder of Commonwealth Partners, to explore his journey from teaching history in San Diego to working alongside legendary state-policy leaders Larry Reed and Joe Overton, eventually leading the Commonwealth Foundation and launching a new organization focused on winning political and policy battles in Pennsylvania. The conversation goes deeper into Matt’s new book, You GOTTA Win Pennsylvania!, and his argument that the states are the critical battleground for America’s future. He discusses the importance of durable state-level infrastructure, school choice, energy policy, litigation, coalition building, taking risks, learning from defeat, and maintaining a long-term view when victories do not come quickly. For anyone interested in entrepreneurship, leadership, philanthropy, public policy, or how bold ideas become lasting change, this conversation offers a candid look at what it takes to keep going and build for the long haul.
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About Going Big! with Kevin Gentry
Welcome to Going Big! — the podcast where we share the stories of people who have truly gone big in their own lives. Hosted by Kevin Gentry, each episode features in-depth conversations with business owners, entrepreneurs, nonprofit leaders, political figures, and other trailblazers who have achieved extraordinary impact in their work and communities. You’ll hear firsthand how they pursued bold ideas, took major risks, overcame challenges, and built something remarkable. We no longer focus solely on fundraising and marketing. Instead, Going Big! explores the full spectrum of leadership, innovation, and personal drive — uncovering the lessons, values, and pivotal moments that propelled our guests to think bigger and push further. Whether you are an aspiring entrepreneur, a nonprofit leader, a political changemaker, or simply someone inspired by real stories of ambition and achievement, Going Big! offers insights and inspiration to help you take your own next leap.
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