Going Big! with Kevin Gentry

What does it mean to go big with your whole life? For Cesar Grajales, it meant immigrating from Colombia with just $80 in his pocket, working in a Miami bakery, and rising to become one of the most recognized Hispanic voices in American public policy and media.

In this inspiring episode of Going Big!, host Kevin Gentry sits down with Cesar to explore his remarkable journey—from playing guitar on Univisio...

What does it really take to go big? For Jeff Rosenthal, it meant launching a global community from scratch, building a cultural movement atop the largest ski resort in the U.S., and investing in the boldest ideas reshaping our future.

In this high-energy episode of Going Big!, host Kevin Gentry sits down with Jeff Rosenthal—co-founder of Summit, co-author of Make No Small Plans, co-owner and co-developer...

On this episode of Going Big!, host Kevin Gentry welcomes Alexandre Pesey, the visionary founder of the Institut de Formation Politique in Paris. Twenty-five years ago, Alexandre returned from the United States with a bold idea—what if the conservative movement in France could be rebuilt from scratch?

At the time, there was no infrastructure, no training programs, no donor base, and no serious conservative presence in the media, c...

How do you go big at a university that’s over 300 years old? For Katherine Rowe, the 28th—and first woman—President of William & Mary, the answer lies in honoring tradition while boldly embracing change.

In this episode of Going Big!, host Kevin Gentry sits down with President Rowe to explore how one of America’s most historic universities is preparing students not for the world as it is—but for the world that’s coming. From re...

On this episode of the Going Big! Podcast, host Kevin Gentry welcomes Brendan McCord—submariner, AI entrepreneur, and deep thinker—for a bold conversation on the biggest force shaping our future: artificial intelligence.

Brendan helped write the Pentagon’s first AI strategy, built and sold two tech companies for over $400 million, and now leads the Cosmos Institute—a nonprofit reimagining AI’s role in advancing human flourishing. I...

At just 24 years old, Daniel Houghton became CEO of Lonely Planet, the world’s largest travel publisher—leading its transformation into the digital age and redefining what it means to explore the world. Now, as founder and CEO of The Travel Library, Daniel is curating an ever-growing collection of editorial travel content, personal destination guides, and inspirational itineraries for adventurers around the globe.

In this episode o...

What if everything you think you know about trade, tariffs, and the American economy is wrong? In this powerful and timely episode of Going Big, host Kevin Gentry sits down with renowned economist Don Boudreaux—former chair of the economics department at George Mason University and co-author of The Triumph of Economic Freedom—to dismantle some of the most persistent economic myths of our time.

From the m...

How does someone with no media background build one of the most trusted conservative voices in America? Erick Erickson’s journey is a bold reminder that with faith, grit, and purpose, you don’t have to follow a traditional path to make a lasting impact.

In this episode of the Going Big! Podcast, host Kevin Gentry talks with Erick about his unconventional rise from lawyer to blogger, from behind-the-scene...

What does it take to not only believe in big ideas—but to win with them? In this episode of the Going Big! Podcast, host Kevin Gentry sits down with conservative icon Morton C. Blackwell, founder and president of the Leadership Institute, for a remarkable conversation about a life spent shaping leaders, building institutions, and going all-in for the causes that matter.

With a career that spans decades—from being the youngest deleg...

What does it mean to Go Big when the odds are stacked against you? In this powerful episode of the Going Big! Podcast, host Kevin Gentry sits down with Scott Strode, founder of The Phoenix, a free sober active community that is redefining recovery across the country.

Scott shares his personal journey from addiction and adversity to climbing literal mountains—and building one of the most impactful recover...

In this landmark episode of the Going Big! Podcast, host Kevin Gentry sits down with Dr. Douglas Bradburn, historian and President & CEO of George Washington’s Mount Vernon, for a sweeping conversation on leadership, legacy, and the enduring relevance of America’s founding father.

What does it mean to Go Big! in a way that’s rooted in humility, preparation, and purpose? Through the life and character of George Washington, we ex...

In this powerful episode of the Going Big Podcast, Tim Kersten sits down with host Kevin Gentry for a candid, wisdom-filled conversation about leadership, legacy, and the lifelong pursuit of excellence. With more than 40 years of experience in nonprofit fundraising and marketing, Tim brings a rare combination of creative brilliance and deep humility to his role as Chairman and CEO of RKD Group—America’s largest direct response fund...

What would you do if you weren’t afraid to fail? For Emily Seidel, that question reshaped everything—from her earliest doubts about leading a national grassroots movement to becoming the CEO of Americans for Prosperity, one of the most influential citizen-powered organizations in the country.

In this episode of Going Big, Emily shares the deeply personal journey that brought her from answering phones on Capitol Hill to leading a te...

Going Big isn’t just a mindset—it’s a framework for transformation, innovation, and lasting impact. In this episode of Going Big!, host Kevin Gentry welcomes Jimmy Hutcheson, the visionary CEO of SPIN and Next Management Partners, who has mastered the art of taking legacy brands and scaling them into digital powerhouses.

Jimmy’s journey from a small-town upbringing in Springfield, Missouri, to leading some of the most recognizable ...

What does it mean to Go Big when the stakes are life and death? Patrick Henry didn’t just give a speech—he ignited a revolution. On March 23, 1775, in a small church in Richmond, Virginia, his legendary words—“Give me liberty or give me death”—transformed hesitation into action and set the course for American independence.

In this episode, Kevin Gentry sits down with Stephen Wilson, Executive Director of the St. John’s Church Found...

What does it take to truly Go Big in life and business? Will Guidara, world-renowned restaurateur and bestselling author of Unreasonable Hospitality, joins host Kevin Gentry to share how relentless pursuit, bold thinking, and investing in people can transform not just an industry—but the way we live and lead.

From making Eleven Madison Park the #1 restaurant in the world to inspiring some of the most popular episodes of the hit ser...

Going Big isn’t just about taking risks—it’s about turning your passion into something that impacts others. In this episode of the Going Big! Podcast, host Kevin Gentry sits down with Neal Wavra, a hospitality visionary who took a bold leap to create something extraordinary.

From growing up in Chicago, where family meals were the heartbeat of connection, to working in world-class restaurants like Charlie Trotter’s and Blackberry Fa...

What does it truly mean to Go Big? For artist Polly Gentry, it meant taking a personal moment of grief and transforming it into a mission of honor, remembrance, and action. After witnessing the heartbreaking events of the 2021 Afghanistan troop withdrawal, Polly was moved to create a one-of-a-kind tribute—her Flags of Honor series, with each piece dedicated to one of the 13 fallen service members.

But Polly didn’t stop at expressio...

On this episode of the Going Big! Podcast, host Kevin Gentry sits down with former U.S. Senator Phil Gramm, a leader whose career has been defined by taking bold risks and reshaping America’s economic policies.

From his early days as an economics professor to becoming a key architect of the Reagan Revolution, Gramm shares his journey of challenging the status quo, fighting for lower taxes, and making tough decisions that changed th...