Going Big! with Kevin Gentry

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.

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, a former high school dropout turned Harvard professor and bestselling author, dives into the importance of individuality and personal fulfillment. He challenges listeners to break free from societal norms that define success through averages. Rose shares his journey from struggle to success, critiques traditional education, and celebrates unique talents in organizations. He also discusses the dangers of collective illusions influenced by social media, encouraging honest conversations that can inspire real change. It's a liberating call to pursue your own path!

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.

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.

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.

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/

Jeff Rosenthal, co-founder of Summit and co-author of 'Make No Small Plans,' shares his journey of building a global community and acquiring Powder Mountain. He discusses the essential mindset of risk-taking and trust in leadership, highlighting how culture surpasses strategy. Jeff emphasizes the significance of embracing failure as a learning opportunity and explores future megatrends in AI and energy. With a focus on building authentic networks, he inspires listeners to dream boldly and redefine their limits for greater success.

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.

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.