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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:

Newt Gingrich on Going Big: Big Ideas, Bold Leadership, and a Vision for America’s Future Jul 28, 2025

Show notes

What does it look like to go big on the national stage, and change the course of history in the process? In this special episode of Going Big!, Kevin Gentry sits down with Newt Gingrich, former Speaker of the United States House of Representatives, to explore the power of bold ideas, strategic leadership, and relentless commitment to getting things done.

From engineering the Contract with America to balancing the federal budget four years in a row, Speaker Gingrich shares behind-the-scenes stories of the decades long effort to transform American politics. He discusses the importance of thinking beyond the status quo, leading with vision, learning every day, and surrounding yourself with people who can help make the impossible possible.

Gingrich also dives into today’s political landscape, offering insight into President Trump’s second term , the threats posed by unchecked bureaucracy, and why we may be on the edge of a new golden age, if we get leadership and innovation right.

This is an episode about thinking long, acting smart, and committing to something bigger than yourself. Whether you're building a movement, launching a business, or fighting for change, Gingrich’s message is clear: the future belongs to those who are willing to go big.

Be sure to check out his latest book, Trump’s Triumph: America’s Greatest Comeback, now available wherever books are sold.

Todd Rose on Breaking the Mold, Ditching Average, and Going Big on Your Own Terms Jul 21, 2025

Show notes

What happens when you stop chasing other people’s definitions of success and start building a life that fits who you really are?

In this episode of Going Big!, Kevin Gentry sits down with Todd Rose—a former high school dropout turned Harvard professor, bestselling author, and co-founder of non-partisan think tank, Populace. From his groundbreaking book The End of Average to his powerful work on Dark Horse and Collective Illusions, Todd has reshaped how we think about individuality, success, and fulfillment.

This episode is a bold invitation to reject one-size-fits-all thinking and embrace a path that’s uniquely yours.

If you’ve ever felt boxed in or stuck following someone else’s blueprint, Todd’s story will challenge you to think bigger, act braver, and start going big—your way.

No Free Lunch: Veronique de Rugy on Debt, Freedom, and the Fight for Growth Jul 14, 2025

Show notes

On this episode of the Going Big! Podcast, host Kevin Gentry welcomes Veronique de Rugy, a nationally syndicated columnist and one of America’s most respected economists advocating for limited government and economic freedom. As the George Gibbs Chair in Political Economy and a Senior Research Fellow at the Mercatus Center at George Mason University, Veronique has spent her career sounding the alarm on unsustainable debt, overregulation, and the quiet damage of bloated government.

In this powerful conversation, Veronique explains why massive government spending isn’t just a political issue—it’s a personal one. It affects your freedom, your future, and your ability to innovate, build, and thrive. She unpacks how unchecked debt drags down opportunity, how economic distortions are quietly paralyzing growth, and why we’re dangerously close to choosing stagnation over progress.

But this isn’t just about what’s wrong—it’s about what’s possible. Veronique shares her own journey from France to America, why she became a champion for free markets, and what she believes we must do now to reignite the spirit of prosperity and unleash a new era of abundance.

If you want a clearer picture of what’s holding America back—and how we break free—this is an episode you don’t want to miss.

Tom Smith on Spend Your Days Like Dollars, Going Big with Integrity, Optimism, and a Life Well Lived Jul 07, 2025

Show notes

What if the real currency of life isn’t money, but your time? For Tom Smith, a highly successful investor and founder of his own investment firm, the most important unit of exchange is the day, and every one of them should be spent wisely.

In this episode of Going Big!, host Kevin Gentry sits down with Tom to explore a remarkable life shaped by hard work, deep thinking, and decisive action. From setting pins in a bowling alley to launching a nationally respected investment firm from above his garage, Tom’s journey proves that where you start doesn’t determine how far you can go.

He shares how a single civics teacher helped change his future, why he left a secure Navy career to pursue the unknown, and how betting on ideas and people became the hallmark of his investing approach.

Tom also delivers a clear warning about America’s mounting debt and why the biggest threats to our future may come from within, not abroad. His message is urgent but hopeful, grounded in experience and a deep belief in personal growth and responsibility.

If you want to learn how to build a meaningful life, contribute to something bigger than yourself, and treat each day like it counts, Tom Smith offers timeless insight from a life lived without shortcuts.

Going Big with James Piereson: How Bold Philanthropy Helped Build a Movement and Reshaped America Jun 30, 2025

Show notes

In this Going Big! conversation, host Kevin Gentry sits down with Dr. James Piereson, renowned political scientist, influential philanthropic leader, and former president of the John M. Olin Foundation, to unpack how big ideas—and bold action—can shape the future of a nation.

Piereson didn’t just write about political revolutions—he funded one. From helping build powerhouse institutions like the Heritage Foundation, Federalist Society, and Manhattan Institute, to championing free markets, constitutional government, and intellectual risk-taking, his story is a blueprint for how to go big with purpose.

In this episode:

Discover how a quiet foundation transformed America’s political and intellectual landscape

Learn why taking a chance on unproven ideas can have a generational impact

Hear how honoring donor intent and sunsetting a foundation created more urgency—and more results

Explore the evolution of the conservative movement through the eyes of one of its chief architects

Get powerful insights on today’s challenges—from political polarization to cultural decline—and what can still be done

Going big isn’t just about scale—it’s about courage, clarity, and conviction. James Piereson lived that model, and this episode is full of hard-earned wisdom for anyone ready to make a difference.

🎧 Tune in now and get inspired to go big in your own way.

Cesar Grajales: From $80 and a Dream to National Impact — Going Big With Vision and Grit Jun 23, 2025

Show notes

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 Univision, to helping build The LIBRE Initiative into a national force for Hispanic outreach, to launching a thriving handmade luxury shoe company called Indie Genius (IG: @buyindiegenius), and now hosting South Florida’s #1 Spanish-language radio show El Escándalo del Día and his own podcast, Sabor a Freedom.

Together, they dive into what it takes to start with nothing and build a life rooted in resilience, joy, and community. Cesar shares how embracing hard work, authenticity, and creativity helped him rise above every challenge—and why enjoying the process is just as important as reaching the destination.

If you’re looking to rediscover what’s possible, this episode is your reminder: Going Big isn’t about titles or trophies—it’s about courage, conviction, and never losing sight of the people you’re inspiring along the way.

Check Cesar Grajales out here https://cesargrajales.news/

Check Libre out here: https://thelibreinitiative.com/

Going Big with Jeff Rosenthal: No Small Plans, No Limits, and the Power of Bold Vision Jun 16, 2025

Show notes

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 of Powder Mountain, and founder of the new venture firm CIV. Together, they explore the early days of turning cold calls into iconic events, the behind-the-scenes story of acquiring Powder Mountain, and the mindset that powers generational leadership.

Jeff opens up about risk, trust, partnership, and why culture always beats strategy. From building authentic communities to backing founders in energy, AI, and advanced manufacturing, his journey is a masterclass in what it means to dream boldly, lead authentically, and execute with purpose.

If you’re ready to challenge your limits, rethink what’s possible, and start living your biggest vision—this episode will show you how.

Going big isn’t a moment—it’s a mindset. And Jeff Rosenthal lives it every day.

Going Big in France: How Alexandre Pesey Sparked a National Movement Jun 09, 2025

Show notes

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, civil society, or education. But Alexandre refused to let that stop him. He began with a single borrowed castle, a handful of students, and a deep conviction that France needed a new generation of leaders.

Alexandre shares how he modeled his efforts on the American conservative movement post-Goldwater, drawing lessons from mentors like Morton Blackwell and Kevin Gentry himself. He discusses how he built not just one institution—but an entire ecosystem of training, journalism, advocacy, and civic engagement. Today, his movement includes over 500,000 donors, a growing national media presence, and a new generation of French leaders with backbone and boldness.

This episode dives deep into the long game—what it takes to inspire people when the odds are stacked against you, how to rally support when you're starting from zero, and why family, faith, and mentorship are the foundation of sustainable impact. Alexandre’s story is proof that one person, with clarity of purpose and relentless determination, can shift the course of a country.

If you’re looking for real-world proof that Going Big! isn’t just possible—it’s necessary—this episode is for you.

Leading a Legacy into the Future: Katherine Rowe on Tradition, Innovation, and Going Big Jun 02, 2025

Show notes

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 reopening during the pandemic to launching a school of computing and coastal sciences, President Rowe shares how bold leadership, deep listening, and strategic vision are guiding William & Mary into the future.

She explains how liberal arts education can thrive in a tech-driven world, why listening is a foundational leadership tool, and how embracing instability often reveals the biggest opportunities to lead.

Whether you're a student, leader, educator, or simply someone navigating change, this conversation is a masterclass in going big—with purpose, with values, and with clarity about the kind of future we want to build.

Brendan McCord on Going Big with AI: Autonomy, Truth, and the Future of Humanity May 26, 2025

Show notes

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. In this episode, he unpacks how we can go big with AI without losing what makes us human.

You’ll hear Brendan’s journey from 610 days beneath the ocean to the front lines of defense innovation and finally to the frontiers of philosophy and public purpose. From decentralization and truth-seeking to why specialization is for ants, Brendan offers a radical vision for how builders and leaders can shape a future worth believing in.

If you're serious about doing meaningful work at scale, this conversation will challenge you to aim higher—and go bigger.

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