Going Big! with Kevin Gentry
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.
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.
Episodes
Mentioned books
Oct 6, 2025 • 44min
Going Big with Don Miller: Why Story Changes Everything
In this episode of Going Big!, host Kevin Gentry sits down with best-selling author and entrepreneur Don Miller. Known for groundbreaking books like Blue Like Jazz, A Million Miles in a Thousand Years, Hero on a Mission, and the transformative Building a StoryBrand, Don shares how storytelling has shaped his life and helped countless leaders and organizations clarify their message.
From his early memoirs to creating one of the most influential frameworks in modern marketing, Don reveals how the art of story can drive growth, inspire action, and create lasting impact. Whether you lead a business, a nonprofit, or a personal project, this episode will help you think bigger, communicate with clarity, and create your own great story.
Now, are you looking to Go Big for your own great cause? Check out Zeffy – the only fundraising platform that delivers 100% of every donor’s gift directly to your cause. Donors can choose to optionally tip Zeffy, but if they give $100, you get $100. Zeffy is a proud sponsor of the Going Big! podcast as we share the goal to empower YOU! to make your greatest impact.
Check them out at https://bit.ly/Zeffy-Going-Big-Podcast
Sep 29, 2025 • 58min
Going Big! With Wendy Borcherdt: Lessons from Ronald Reagan’s Vision for America
Join Wendy Borcherdt, a dedicated Reagan supporter and civic leader, as she shares her firsthand experiences with Ronald Reagan's remarkable journey. She highlights his unique communication style, moral compass, and leadership during turbulent times, including campus riots and the Cold War. Wendy also discusses the grassroots fundraising strategies that fueled his campaigns and reflects on Reagan's commitment to women's roles in leadership. Listeners will gain insights into purposeful leadership and be inspired by Reagan's vision for America.
Sep 22, 2025 • 1h 26min
One Year of Going Big!: The Best of Going Big
This highlights episode of the Going Big! Podcast celebrates our first year with some fantastic guests. Host Kevin Gentry brings together the most powerful clips from Year One, showing what it means to Go Big in business, leadership, and life.
Hear directly from Jeff Rosenthal of Summit and Powder Mountain, Speaker Newt Gingrich, Professor Todd Rose, restaurateur Will Guidara, Senator Phil Gramm, Reverend John Yates, radio host Erick Erickson, businessmen and philanthropists Art Pope, Tom Smith, Doug DeVos, and University President Katherine Rowe.
Their stories highlight how risk-taking fuels growth, how mentors multiply your impact, and how bold leadership inspires others. Whether you are new to Going Big! or have been with us since the beginning, this highlights episode is the perfect way to catch the very best lessons on Going Big! so far.
Sep 15, 2025 • 27min
President Lech Wałęsa on Faith, Courage, and Going Big for Democracy
In this inspiring episode of the Going Big podcast, host Kevin Gentry sits down with President Lech Wałęsa, the shipyard electrician from Gdańsk, Poland, who defied the Soviet Union, ignited a movement of over ten million people, and helped reshape the course of history. With courage rooted in faith and conviction, President Wałęsa led the Solidarity movement, earned the Nobel Peace Prize, and became the first democratically elected President of Poland since 1926— a true example of what it means to go big.
Now in his eighties, President Wałęsa reflects on how faith overcomes fear, why collective wisdom is vital for the future, and the responsibility of today’s leaders to confront global challenges with courage and clarity. From bringing down walls of oppression to calling for bold leadership in the twenty-first century, this conversation is a reminder that going big is not just about ambition — it is about rising to the moment and inspiring others to do the same.
Learn more at historyexplorer.com
Sep 8, 2025 • 39min
🎙️ Going Big with Jim Law: A Vineyard, a Vision, and the Virtue of Patience
Jim Law’s story is not one of chasing spotlight or scale. It is a story of deliberate choices, decades of experimentation, and a deep respect for the land. From the hills of the Congo to the rocky slopes of Virginia’s Blue Ridge Mountains, Jim has lived a life built on clarity, humility, and conviction. At Linden Vineyards, he has chosen to remain small so that the quality could go deep. His focus on terroir, soil, and precision farming has turned him into one of the quiet pioneers of the East Coast wine movement. He did not set out to Go Big—but by following his calling with integrity, that is exactly what he has done.
In this inspiring episode of Going Big, host Kevin Gentry uncovers how Jim built a legacy without ever chasing one. They talk about growing grapes with intention, creating wine that reflects its place, and mentoring a new generation of growers to think long-term and lead with purpose. Whether you're a winemaker, a business builder, or simply someone who wants to live a meaningful life, Jim Law reminds us that you don’t have to scale fast to Go Big. You just have to plant the right seeds and stay true to what matters.
Sep 1, 2025 • 58min
Going Big for Free Speech: Greg Lukianoff on Empowering Minds and Protecting Expression
Going Big means standing up for fundamental principles when it is hard, not just when it is popular. Greg Lukianoff has built a career doing exactly that.
In this timely conversation, host Kevin Gentry talks with Greg, the president of the Foundation for Individual Rights and Expression (FIRE), about what it truly takes to protect one of our most essential freedoms: the right to speak, to question, and to think independently.
Greg has gone big in every way. He has taken on universities, pushed back against digital censorship, partnered with innovators to keep artificial intelligence free from political bias, and defended the kind of open dialogue that fuels human progress. He is not just reacting to the threats of our time. He is shaping the future by building institutions that protect expression at scale.
This episode captures the Going Big spirit. It is about using ideas to build, using courage to lead, and refusing to play small when the stakes are high. If you care about liberty, innovation, education, or the future of truth itself, this conversation will challenge you to think bigger, lead braver, and stand taller.
Aug 25, 2025 • 56min
Going Big in Business, Public Policy, and Philanthropy: The Art Pope Blueprint
Join host Kevin Gentry for an insightful conversation with Art Pope—a principled leader who has gone big in business, in state government, and in giving back.
As CEO of Variety Wholesalers, Art helped grow a 600-store retail network serving thousands of communities. He’s also served as North Carolina’s state budget director, spent years in the legislature, and leads major philanthropic efforts through the John William Pope Foundation and the Bradley Foundation.
In this episode, Art shares lessons from his Depression-era father, the bold moves behind his company’s recent Big Lots acquisition, and why real philanthropy is about investing in freedom and opportunity for future generations.
If you're aiming to lead with conviction, think long-term, and make a lasting impact—this conversation is for you.
Aug 18, 2025 • 1h 35min
Going Big with Rev. John Yates: Faith, Calling, and Transformational Leadership
Join host Kevin Gentry on the Going Big podcast as he sits down with Rev. John Yates, a visionary leader who transformed a struggling church into a thriving community hub with national impact. In this inspiring episode, Rev. Yates shares profound insights on discovering your calling, embracing bold leadership, and living a life dedicated to serving others. From founding innovative programs like the Fellows and Timothies initiatives to navigating the challenges of church renewal and legal battles, John’s story is a testament to resilience, faith, and going big in purpose.
Whether you’re seeking to deepen your leadership, answer a higher calling, or make a difference in your community, this conversation will encourage you to step out in faith, build meaningful relationships, and persist through adversity. Tune in for practical wisdom on mentorship, balancing family and ministry, and how to leverage your unique gifts for lasting impact.
Remember, going big isn’t just about scale—it’s about living boldly with intention and heart. Don’t miss this powerful episode full of hope, challenge, and encouragement to pursue your next big leap!
Aug 11, 2025 • 49min
Going Big with Alan Smolinisky: From Immigrant Roots to Dodger Ownership and Beyond
In this inspiring episode of *Going Big!*, host Kevin Gentry sits down with Alan Smolinisky, a remarkable American entrepreneur, investor, and co-owner of the Los Angeles Dodgers. Alan shares his compelling immigrant family story—from his parents’ courageous journey from Argentina to building a successful garment business in Los Angeles, to his own unconventional path through entrepreneurship and value investing. He discusses the resilience and optimism that fuel his ventures, including his thriving real estate empire and his bold move into professional sports ownership.
Alan also opens up about his philanthropic work focused on poverty alleviation and immigration reform, and how hosting one of the largest naturalization ceremonies at Dodger Stadium became a powerful symbol of hope and patriotism. Reflecting on personal loss, the devastation of the Palisades fire, and the importance of community, Alan’s story is a testament to perseverance, visionary risk-taking, and giving back.
This episode offers invaluable lessons on going big by embracing passion, persistence, and purpose, making it a must-listen for entrepreneurs and dreamers alike.
Aug 4, 2025 • 1h 2min
Going Big: Political Revolutions, Fundraising, and Friendship Across the Aisle with Roger Craver and Richard Viguerie
On this episode of Going Big, host Kevin Gentry brings together two legends who have helped shape American politics and political fundraising from opposite ends of the spectrum: Roger Craver, the driving force behind progressive fundraising efforts for groups like the ACLU and Sierra Club, and Richard Viguerie, the conservative pioneer who transformed direct mail into a movement-building machine.
Despite their sharp political differences, Roger and Richard share something bigger: decades of leadership, innovation, and an enduring friendship built on respect and shared experience. In this conversation, they reflect on the early days of grassroots organizing, the evolution of political fundraising, and how their work empowered citizens to act boldly and shape the future of the country.
Kevin digs into the values that have kept both men grounded through decades of cultural and political change. Going big doesn't mean going-along-to-get-along. It means trendsetting, innovation, big new ideas, and a willingness and openness to lead from your convictions while learning from others.
Whether you're in politics, fundraising, or just looking to make a bigger difference in the world, this conversation will challenge you to think bigger, listen harder, and lead with principle.
