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Going Big! with Kevin Gentry — Business
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, Going Big! has consistently ranked as a top podcast on iTunes in its category and has earned multiple national honors, including the 2024 MarCom Gold Award for Non-Profit Podcast, the 2024 Viddy Gold Award for Non-Profit and Marketing Podcast, the 2025 Viddy Award, and the 2025 Communicator Award.

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.

Listen on Spotify, iTunes, Amazon, iHeart Radio, Pandora, and YouTube. Follow us on social media and visit TenXStrategies.com for more great content and resources.

Copyright: © Copyright 2024 All rights reserved. Best Non-Profit Podcast

Latest Episodes:

The Power of Parents in Education with Darla Romfo (Children's Scholarship Fund) Sep 21, 2026

Show notes

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.

Simplify: Doing What Actually Matters with Axios co-founder Mike Allen Sep 14, 2026

Show notes

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.

The Billion-Dollar Bet on Educational Opportunity with Tony de Nicola Sep 07, 2026

Show notes

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/

Agency: Why He Took a $25K Job With a Harvard MBA with Ian Rowe (American Enterprise Institute) Aug 31, 2026

Show notes

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.

From Green Beret to Media Powerhouse with Nick Freitas Aug 24, 2026

Show notes

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.

Why Pennsylvania is the Key to Victory with Matt Brouillette (Commonwealth Partners) Aug 17, 2026

Show notes

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.

The Character Crisis in American Leadership with Frank Atkinson Aug 10, 2026

Show notes

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/

Building a Fortune 500 Culture at Tractor Supply with Joe Scarlett Aug 03, 2026

Show notes

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

The Young Leaders Fighting for Bolivia's Future with Juan Pablo Chamon and Jorge Velarde Rosso (Libera Bolivia) Jul 27, 2026

Show notes

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.

Making the Constitution Come Alive with Janine Turner and Cathy Gillespie (Constituting America) Jul 20, 2026

Show notes

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.

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