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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:

Going Big with Bo Ghirardelli & Nicolas Cary: Sky’s the Limit and the American Dream Feb 23, 2026

Show notes

When people are able to apply their unique talents to real-world problems, we all benefit.

But too often, talented entrepreneurs lack the practical tools, know-how, or relationships they need to turn a good idea into a working business -- and so they miss out on the essential seed capital to take those ideas to market.

That’s the gap Bo Ghirardelli and Nicolas Cary built Sky’s the Limit to close.

Together, serial builders and lifelong friends Bo and Nic (of Blockchain.com) developed a digital success platform that delivers tangible support for low-income, earliest-stage entrepreneurs to access education, mentorship, and capital. Now, they're scaling it to truly Go Big.

In this episode of Going Big!, Bo shares the origin story of Sky's the Limit, which began as an idea during the Arab Spring, when Bo was stationed in Morocco and aspiring entrepreneurs kept approaching him with business ideas but no clear path forward. Nic connects those lessons to a massive challenge in the United States: millions of people with talent and ambition, but lacking know-how, community, and early access to capital -- and a growing sense that opportunity is slipping away.

Bo and Nic explain how Sky’s the Limit scaled beyond a brick-and-mortar program into a tech-enabled platform, including “missions” that guide entrepreneurs step-by-step, mentor connections built through community and virtual events, and a funding system that helps founders practice pitching and compete for grants.

The conversation also dives into mentorship as a force multiplier for both skills and character, and touches on Nic's experience in the world of cryptocurrency and innovative financial models. The episode closes with a clear invitation: if you’re looking up at the sky and imagining a better future, Sky’s the Limit exists to help you build it.

Going Big with John Yates III: Faith, Leadership, and the Digital Age Feb 16, 2026

Show notes

What if Going Big doesn’t mean building a massive platform — but laying a foundation that lasts for generations?

In this episode of Going Big!, host Kevin Gentry sits down with Reverend John Yates III, rector of Holy Trinity Anglican Church in Raleigh, North Carolina. The son of influential pastor John Yates II, Yates has chosen a different but equally ambitious path to live out and develop long-term faithfulness.

Yates shares how his father’s steady leadership shaped him, what he learned working closely with renowned theologian John Stott, and why mentoring often happens not through formal instruction but through quiet proximity and example. He explains why playing the long game — investing in people over 10, 20, or 30 years — may be the most countercultural form of leadership in today’s world.

The conversation turns to one of the most pressing challenges facing leaders today: the digital revolution. Yates argues that smartphones and social media are not just tools, but forces shaping our humanity at a scale comparable to Gutenberg’s printing press. He reflects on how this technological shift is transforming attention, community, and even the experience of faith.

From lessons on mentorship and intellectual humility to navigating leadership during COVID and guiding a congregation through cultural change, this episode explores how leaders can remain grounded, curious, and faithful in an age of distraction.

If you’ve ever wondered what the connection is between integrity and real impact — this conversation will challenge and encourage you to rethink what it truly means to Go Big.

Going Big with Fr. Robert Sirico: Faith, Freedom, and the Formation of a Life’s Calling Feb 09, 2026

Show notes

In this episode of Going Big, host Kevin Gentry sits down with Fr. Robert Sirico — priest, thinker, and co-founder of the Acton Institute — to explore a remarkable life shaped by bold ideas, unexpected turns, and an unwavering commitment to the dignity of the human person.

Fr. Sirico reflects on his early years in Brooklyn, his immersion in the social movements of the 1970s, and the intellectual journey that ultimately led him back to faith and into the priesthood. He shares how thinkers like Michael Novak, Cardinal Avery Dulles, and others helped him integrate theology, human freedom, economics, and moral reasoning into a unified vision.

Together, Kevin and Fr. Sirico dive into the founding of the Acton Institute, the risks involved in challenging prevailing assumptions within religious institutions, and the decades-long effort to move global conversations about faith and economics toward a deeper understanding of freedom and virtue.

This conversation also explores the role of mentors, the meaning of humility, lessons from serving as a hospital chaplain, and how suffering, truth, and compassion all shape the pursuit of one’s calling.

Whether you're interested in leadership, intellectual formation, personal transformation, or the intersection of faith and free societies, this episode offers a rare window into a life devoted to Going Big with purpose.

Going Big with Aditi Goel and David Carroll: Taking On America’s Hidden Justice Crisis Feb 02, 2026

Show notes

In this episode of Going Big!, host Kevin Gentry sits down with Aditi Goel and David Carroll, the executive director and founder of the Sixth Amendment Center, to explore one of the most misunderstood crises in American law: the failure of many local courts to provide legal counsel to people who can’t afford it.

Though the Constitution guarantees the right to an attorney, millions of Americans are being prosecuted, sentenced, and even jailed without ever speaking to one. In lower courts, the right to counsel often doesn't exist.

Goel and Carroll share their journey of building the only national organization dedicated solely to this problem. Their unique, nonpartisan model partners directly with states to identify structural gaps, uncover unintentional violations, and help governments meet their constitutional obligations without litigation.

This episode offers a sobering look at what’s broken in America’s criminal justice system—and an inspiring path toward fixing it.

If you care about civil liberties, smart governance, and how to go big with focused mission-driven work, this conversation is essential.

Going Big with Dr. Rand Paul: Independent Leadership from the Operating Room to the Senate Floor Jan 26, 2026

Show notes

What if going big in politics meant doing less?

Dr. Rand Paul is a U.S. Senator from Kentucky—and one of the most consistently independent voices in American government. In this episode of Going Big!, we talk about how his commitment to liberty, limited government, and constitutional principles have shaped every step of his unconventional journey.

You’ll hear how growing up in the household of Ron Paul formed his early worldview, how medicine taught him the value of real-world outcomes, and why his 2010 Senate run nearly started with a political headline and a trip to the doghouse. Rand unpacks the deeper philosophy behind his contrarian stands, from COVID policy to federal spending, and what it takes to speak truth when the easier path is silence.

He makes the case that the job of a legislator isn’t to pass laws—it’s to defend freedom. Even when liberty is the harder argument to sell.

And if you’re wondering how to make a difference? Rand offers a roadmap: start by reading, get a real job, and show up where your voice matters most—especially in primaries.

Going Big with Dr. Michael Crow: Redesigning the American University Jan 19, 2026

Show notes

What if excellence in higher education wasn’t about who you exclude—but about how many you can empower to succeed?

In this episode of Going Big!, host Kevin Gentry sits down with Dr. Michael Crow, President of Arizona State University and one of the most visionary university leaders in America. Over the past two decades, Dr. Crow has led a sweeping transformation of ASU—turning it into the nation’s largest research university, dramatically expanding access, and pioneering a new model of continuous innovation.

They explore how ASU scaled from 55,000 to over 200,000 degree-seeking students without compromising quality, why the university now graduates more engineers than nearly any institution in America, and how it became a driving force behind the largest foreign direct investment in U.S. history. Dr. Crow also unpacks the cultural resistance he faced, the radical accountability embedded in ASU’s charter, and how universities can become true engines of national progress.

If you care about the future of higher education, institutional transformation, or what it means to lead boldly at scale—this conversation will reset your expectations.

Going Big with Governor Glenn Youngkin: From Basketball to the Boardroom to the Capitol Jan 12, 2026

Show notes

In this episode of Going Big!, host Kevin Gentry sits down with Governor Glenn Youngkin for a wide‑ranging and deeply personal conversation that goes far beyond politics.

From growing up in a working‑class Virginia family shaped by resilience, to leading one of the world’s most influential investment firms, to answering an unexpected call to public service, Governor Youngkin shares the defining moments that prepared him for leadership. He reflects on the mentors who challenged him, the role of faith in shaping his marriage and decision‑making, and the lessons sports taught him about teamwork, discipline, and results.

Kevin and Governor Youngkin explore what it really means to go big as a leader—why listening matters more than talking, how values guide hard decisions, and why execution ultimately separates good ideas from real impact. The conversation connects business leadership, public service, and personal purpose in a way that’s practical, honest, and deeply human.

Whether you’re leading an organization, discerning a calling, or simply asking what meaningful service looks like in your own life, this episode offers a compelling blueprint for leading with clarity, conviction, and purpose.

Going Big with Gay Gaines: The Woman Behind the GOP Revolution and the Revival of Mount Vernon Jan 05, 2026

Show notes

What does it take to launch a revolution—twice?

In this episode of Going Big!, host Kevin Gentry sits down with Gay Gaines, one of the most influential civic leaders of the last half-century. She helped build GOPAC into the engine that propelled Newt Gingrich to the speakership in 1994. Then she went on to raise over $100 million to transform Mount Vernon into the national treasure it is today.

Gay’s story is about more than political strategy or philanthropy—it’s about fearlessness. From befriending Margaret Thatcher and Bill Buckley to organizing with Rush Limbaugh and inspiring thousands to give generously, she shows what it means to commit fully to a cause you believe in.

Tune in to hear how she built movements, mentored leaders, and raised money the old-fashioned way: by asking big, bold, unapologetic questions. This is a masterclass in conviction, contribution, and Going Big.

Going Big with Tyler Cowen, the Information Billionaire: The Future Belongs to the Non-Complacent Dec 29, 2025

Show notes

Tyler Cowen returns to Going Big! for a sweeping conversation on ambition, disruption, and how to think clearly in a world moving faster than ever.

From his early days studying Austrian economics at George Mason to running one of the most influential economics blogs in the world with Marginal Revolution, Cowen reflects on the personal choices that shaped his path—and the broader trends that will shape the future. Along the way, he shares what drives his relentless curiosity, why ambition is underrated, and how to keep growing intellectually in a rapidly changing world.

He also offers insights into the rise of AI, the future of education, the bureaucracy of philanthropy, and the subtle dangers of social comfort. Plus: how he reads 5–10x faster than most people, how he chooses podcast guests, and why "not going crazy" is one of the most overlooked traits of long-term success.

If you're curious about what it takes to build a life of impact—and how to stay sharp, bold, and useful in the AI era—this episode is for you.

Going Big with Scott Beaulier: Rethinking Higher Ed with a First-Gen College Dean Dec 22, 2025

Show notes

Host Kevin Gentry sits down with Dr. Scott Beaulier, Dean of the University of Wyoming College of Business, for a conversation about what it takes to keep going when life and leadership get hard. Dr. Beaulier shares how growing up in Iron Mountain, Michigan, working his way up at McDonald’s, and being the first in his family to pursue college shaped his grit, discipline, and drive to pursue something bigger.

From marathon miles to major decisions, he unpacks the moments that define you, including “hitting the wall,” facing pressure, and pushing through when quitting feels easier. He also shares how mentors changed his trajectory, why higher education needs real innovation, and what it looks like to lead with purpose, resilience, and a willingness to challenge the status quo in order to create opportunity for others.

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