Going Big! with Kevin Gentry

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/

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.

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.

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.

What does it take to lead with integrity when compromise seems inevitable? In this episode of Going Big!, Kevin Gentry sits down with attorney, historian, and author Frank Atkinson to explore one of the most important questions facing leaders today: Can you remain true to your principles while navigating politics, public service, and positions of influence? Drawing from his newly released novel, The Lion's Den: Renewing Our Democracy by Renewing Ourselves , Frank shares how the biblical story of Daniel, the leadership of George Washington and James Madison, and decades of firsthand experience in government shaped his understanding of courage, character, and servant leadership. Together, Kevin and Frank discuss why compromise is sometimes necessary—but why conviction must never be abandoned. They examine the role of virtue in public life, the importance of preparing for difficult moral decisions before they arrive, and why renewing our institutions begins with renewing ourselves. Whether you serve in government, business, the nonprofit sector, or your local community, this conversation offers timeless lessons on leadership, perseverance, and the responsibility each of us has to strengthen the future through our own choices. You can get your copy of Frank's new novel, The Lion's Den: Renewing Our Democracy by Renewing Ourselves, on his website: https://www.frankatkinson.com/

In this episode of Going Big!, host Kevin Gentry sits down with Joe Scarlett, retired CEO of Tractor Supply Company, to explore the leadership principles behind one of retail’s most remarkable turnarounds. For nearly 30 years, Joe helped transform Tractor Supply from a struggling retailer into a Fortune 500 company with more than 2,500 stores nationwide. But Joe believes the company’s greatest achievement wasn’t its growth—it was the culture that made that growth possible. Joe shares how listening to frontline employees, empowering others to make decisions, building trust with partners, and creating a culture of accountability helped reshape an entire organization. He also reflects on the mentors who influenced him, the lessons he’s learned about humility and delegation, and why he has always considered himself a “head coach” rather than simply a CEO. Whether you lead a business, a nonprofit, or a team of any size, this conversation offers practical insights on building organizations where people thrive, culture drives performance, and leadership is measured by the success of others. You can find more of Joe's advice on life, leadership, and giving back, by signing up for his newsletter at joescarlett.com

In this episode of Going Big!, host Kevin Gentry sits down with Jorge Velarde Rosso and Juan Pablo Chamon, the founders of Libera Bolivia, to discuss what it means to defend freedom under extraordinary circumstances. As young leaders living under an increasingly authoritarian socialist government, they chose not to stay silent. Instead, they built a movement dedicated to developing the next generation of leaders committed to liberty, free markets, and democratic institutions—even when that work came at great personal cost. Jorge and Juan Pablo share the remarkable story behind Libera Bolivia, the mentorship that launched their mission, the challenges of building an organization from the ground up, and the difficult decision that forced Juan Pablo into exile after politically motivated criminal charges. They explain why lasting cultural change begins with investing in young people, why freedom requires courage and long-term commitment, and why they remain optimistic about the future of Bolivia and Latin America despite years of political and economic turmoil. Whether you're interested in leadership, institution-building, public policy, or the power of ideas to shape a nation, this conversation offers an inspiring look at what it takes to go big in pursuit of a freer future.

How do you make a document written more than 230 years ago come alive for a generation raised on YouTube, social media, and streaming video? Janine Turner and Cathy Gillespie believe the answer isn't another textbook—it's storytelling. In this episode of Going Big!, host Kevin Gentry sits down with the founder and CEO of Constituting America to explore how they've spent the past fifteen years transforming civics education through film, music, classroom engagement, and student creativity. They share the personal stories that led them to launch the organization, the lessons they've learned building a national nonprofit, and why they believe America's future depends on helping young people understand not just the Constitution itself, but the remarkable ideas that have preserved freedom for nearly 250 years. Whether you're a nonprofit leader, educator, parent, or someone who cares about developing the next generation of leaders, this conversation offers practical insights into visionary leadership, the power of creativity, and what it takes to build a mission-driven organization that is changing lives.

In this episode of Going Big!, host Kevin Gentry sits down with Dr. Joshua Hall, Dean of the John Chambers College of Business and Economics at West Virginia University, for a conversation about leadership, mentorship, economic opportunity, and the future of higher education. Josh shares how one professor changed the course of his life, why thriving communities are built on strong institutions, and how visionary leadership can reshape an entire state. From helping secure a transformational $20 million gift to launching nationally recognized programs in business ethics, artificial intelligence, and experiential learning, he explains why the best leaders focus less on preserving institutions and more on redesigning them to serve people better. Along the way, Josh offers practical lessons on building teams, aligning incentives, raising bold philanthropic support, embracing experimentation, and preparing students for a rapidly changing world. Whether you lead a nonprofit, a business, a university, or simply want to make a greater impact through your own work, this conversation offers an inspiring look at what it really means to go big by investing in people and creating opportunities that last.

David Rubenstein has spent a lifetime building extraordinary institutions—and studying the leaders who built the ones that came before him. In this episode of Going Big!, host Kevin Gentry sits down with the co-founder of The Carlyle Group for a wide-ranging conversation about leadership, American history, entrepreneurship, philanthropy, and the enduring qualities that define great leaders. Drawing on decades of studying presidents, founders, military leaders, and CEOs, Rubenstein shares why humility often matters more than charisma, why perseverance is a better predictor of success than early achievement, and what today's leaders can learn from figures like George Washington, Abraham Lincoln, and James Baker. Together, they explore whether the American Revolution was the greatest startup in history, whether America is still a worthy long-term investment, why capitalism has fueled one of history's greatest traditions of philanthropy, and what gives Rubenstein optimism about the nation's future despite today's challenges. Whether you're leading a business, building a nonprofit, serving your community, or simply looking to make a greater contribution, this conversation offers timeless lessons on leadership, institution building, and living a life that leaves a lasting legacy.

In this episode of Going Big!, host Kevin Gentry sits down with filmmaker Jon Erwin, the creative force behind Young Washington, the new theatrical release opening July 3. Known for I Can Only Imagine, Jesus Revolution, American Underdog, and House of David, Erwin shares why this film is his most ambitious project yet — and why he believes this is a story audiences should experience on the big screen. Together, they explore the little-known early years that shaped George Washington before he became the leader history remembers. Jon explains how Young Washington brings to life a gripping origin story marked by failure, resilience, courage, and servant leadership. If you care about great storytelling, American history, or films that leave you thinking long after the credits roll, don’t miss this conversation. Then make plans to see Young Washington in theaters starting July 3.

In this episode of Going Big!, Kevin Gentry sits down with Senator Steve Daines for a wide-ranging conversation about faith, risk, entrepreneurship, family, and public service. Daines reflects on the major leaps that shaped his life, from moving his young family to China with Procter & Gamble, to helping build RightNow Technologies in Bozeman, to stepping into the political arena and serving 14 years in Congress. Together, they explore what China looks like up close, what entrepreneurship taught him about leadership under pressure, why he felt called into public service, and why he says this next chapter is not about retirement but repurposing. The conversation also touches on marriage, grief, gratitude, and the kind of legacy he hopes to leave for the next generation.

In this episode of Going Big!, host Kevin Gentry sits down with Dr. Jane Kamensky, president and CEO of Thomas Jefferson’s Monticello, for a timely conversation about Thomas Jefferson, the Declaration of Independence, and the ideas that have shaped America for nearly 250 years. Kamensky explains why Jefferson was chosen to draft the Declaration at just 33 years old, how divided and uncertain the Continental Congress really was, and why the document’s opening vision became far more than a list of grievances. She also explores the central contradiction in Jefferson’s legacy: how the author of words about equality could also participate in slavery on a vast scale. Together, they discuss America’s approaching 250th anniversary, the meaning of reflective patriotism, and the role that Monticello plays in preserving that legacy into the future.

In this episode of Going Big!, host Kevin Gentry sits down with Princeton professor Dr. Robert George for a wide-ranging conversation about truth, freedom, virtue, and the future of the American experiment. As the nation approaches its 250th anniversary, Robert reflects on what Americans often misunderstand about the founders, why George Washington was indispensable, and why a republic cannot survive without moral seriousness and civic friendship. George also shares his own remarkable story, from growing up in Appalachia as the grandson of immigrant coal miners to becoming one of the country’s leading public intellectuals. Along the way, he explains why free speech is essential to truth-seeking, what his friendship with Cornel West teaches about disagreement, and why he remains hopeful about the next generation of Americans.

In this episode of Going Big!, host Kevin Gentry welcomes economist Daniel Di Martino back for a timely conversation about Venezuela, freedom, assimilation, and the future of America. Raised in Caracas during one of the most dramatic political and economic collapses in modern history, Daniel shares what it was like to watch shortages, inflation, and repression reshape everyday life, and how those experiences led him to come to the United States and speak out. Together, they explore what prosperous societies forget, why immigration and assimilation matter, what Daniel’s research says about family and culture, and why he remains hopeful about both Venezuela and America. This episode offers a firsthand look at the cost of collectivism and a serious conversation about freedom, opportunity, and where nations go from here.

In this episode of Going Big!, host Kevin Gentry sits down with producer Drake Springer and director Meredith Danluck to discuss Why We Dream, a documentary that follows World War II veterans returning to Normandy 80 years after D-Day. With many of the veterans now more than 100 years old, the film captures a vanishing generation’s memories of war, service, sacrifice, and the lives they built afterward. Together, they explore how to tell a World War II story in a way that feels fresh and deeply human; why the filmmakers fought to keep the veterans, not the brand, at the center; and how storytelling can preserve living memory before it disappears. The conversation also examines risk, leadership, and the hunger many people feel today for meaning, connection, and a renewed sense of duty to one another.

After losing her husband, Navy SEAL Lieutenant Brendan Looney, in Afghanistan, Amy Looney Heffernan could have stepped back from the world. Instead, she chose a harder path: building a life of service, leadership, and impact in his memory. On this episode of Going Big!, host Kevin Gentry talks with Amy, now President of the Travis Manion Foundation, about grief, resilience, Memorial Day, and how service can help turn pain into purpose. She shares the deeply personal story behind her journey, the values Brendan lived by, and how the Foundation is equipping veterans, families of the fallen, and young people to lead with character in communities across America. Learn more about The Honor Project

In this episode of Going Big!, host Kevin Gentry sits down with former Vice President Mike Pence for a conversation about faith, conviction, public service, and the moments that test a leader’s character. Pence reflects on his journey from a young Democrat inspired by John F. Kennedy to a Reagan conservative, the hard lessons he learned from early political defeats, and the principles that shaped his years in Congress, as governor of Indiana, and in the White House. They also discuss January 6, the constitutional duty Pence believed he was bound to uphold, and his continued work to defend traditional conservative ideas through Advancing American Freedom and his new book, What Conservatives Believe: Rediscovering the Conservative Conscience . For anyone interested in leadership under pressure and the future of the conservative movement, this is a conversation worth hearing.

In this episode of Going Big!, host Kevin Gentry talks with Kip Woodward, a Canadian business leader, investor, and public-policy advocate whose career has spanned family enterprise, ranching, health care governance, and reform efforts around some of Canada’s most entrenched institutional challenges. Kip reflects on what it takes to lead at scale, challenge broken systems, and take risks without losing perspective. From entrepreneurial pivots to public controversy, this conversation explores curiosity, resilience, governance, and the kind of leadership required when the answers are neither simple nor popular.

Human trafficking and exploitation are often hidden in plain sight. In this episode of Going Big!, host Kevin Gentry sits down with Rev. Becca Stevens, founder of Thistle Farms, to explore how one home for five women became a survivor-led movement serving around 1,500 women each year through housing, employment, and long-term support. Stevens shares what most people still misunderstand about trafficking, why punishment alone cannot heal deep wounds, and how Thistle Farms built a distinctive model of restorative justice through social enterprise, community, and love put into practice. It’s a conversation about healing, entrepreneurship, faith, and what it takes to build something big enough to help women find their way home again.