Going Big! with Kevin Gentry

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

  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.

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• Going Big with James Piereson: How Bold Philanthropy Helped Build a Movement and Reshaped America

  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.

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• Cesar Grajales: From $80 and a Dream to National Impact — Going Big With Vision and Grit

  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/

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

  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.

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• Going Big in France: How Alexandre Pesey Sparked a National Movement

  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.

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