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.
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.
Episodes
Episodes



Jan 27, 2025
Jan 27, 2025
50 min
In this episode of the Going Big! Podcast, host Kevin Gentry welcomes Mike Richey, a legendary leader in fundraising and longtime head of philanthropy at the University of Kentucky. With a career spanning over 50 years, Mike has raised billions of dollars, pioneered innovative giving strategies, and inspired countless teams to achieve transformational results.
Mike shares powerful insights on what drives philanthropy, the importance of big ideas, and how to build meaningful relationships with donors. From spearheading groundbreaking campaigns to impacting communities across Kentucky, his wisdom offers a masterclass in leadership, vision, and perseverance.
Whether you're a seasoned fundraiser or just starting out, this episode is filled with actionable advice and inspiring stories that will motivate you to think bigger and aim higher.
Don’t miss this deep dive into the heart of philanthropy and the power of Going Big!



Jan 20, 2025
Jan 20, 2025
58 min
In this episode of the Going Big Podcast, Kevin Gentry sits down with Gary Leff, founder of the renowned travel blog View from the Wing and a globally recognized travel expert. Gary shares his inspiring journey of transforming a personal passion for frequent flyer programs and travel into a blog that reaches millions of readers worldwide.
He delves into the art of maximizing points and miles to create unforgettable travel experiences, from securing once-in-a-lifetime upgrades to helping loved ones overcome travel barriers. Gary’s stories showcase the profound ways travel opens doors—not just for personal exploration but for connecting with those who matter most. Beyond his remarkable anecdotes, Gary offers practical advice for travelers at all levels.
Learn how to navigate loyalty programs, choose the best airlines and hotels, and plan trips that deliver maximum value and enjoyment. Gary also reflects on the lessons he's learned along the way, emphasizing the importance of pursuing passions and making the most of every opportunity.
Whether you're a seasoned traveler or looking to embark on your next adventure, this episode is filled with actionable insights and heartfelt inspiration to help you "go big" in your own travel journey and beyond.



Jan 13, 2025
Jan 13, 2025
1hr 4 min
In this episode of the Going Big! Podcast, Kevin Gentry is joined by Doug DeVos—business leader, philanthropist, and co-chair of the DeVos Family Foundation—for an inspiring conversation about the power of belief, accountability, and resilience. Doug shares personal stories of his family’s journey with Amway, illustrating how a belief in people’s unlimited potential can drive transformation.
From early entrepreneurial ventures to global success, Doug highlights the importance of creativity, integrity, and persistence in overcoming challenges. He also reflects on the principles of free enterprise, civic responsibility, and faith, emphasizing the need to foster respect and dignity for all. Whether you're an entrepreneur or nonprofit leader, this episode will leave you inspired to dream big, overcome obstacles, and make a lasting impact.
Tune in to hear Doug’s incredible insights, and don’t forget to subscribe, leave a review, and share this episode with others who want to "go big" in their mission and purpose!



Jan 6, 2025
Jan 6, 2025
27 min
In this thought-provoking episode of the Going Big! Podcast, host Kevin Gentry sits down with Jeff Frazee, Venture Partner at Liberty Ventures, founder of Young Americans for Liberty, and a visionary leader in the liberty movement. With a career dedicated to advancing freedom and empowering future leaders, Jeff shares his inspiring journey from managing Ron Paul's groundbreaking presidential campaigns to creating organizations that leave a lasting impact on policy and culture.
Jeff delves into the transformative power of grassroots movements, the importance of principled leadership, and how his work with initiatives like Stand Together Ventures and Trust Ventures is shaping a brighter future for freedom in America. He discusses the concept of "Liberty Lighthouse States," an innovative strategy to enact policy changes at the state level, and why building strong, authentic relationships is crucial for achieving lasting success in the liberty movement.
Whether you're a student passionate about political activism, an entrepreneur seeking to make a difference, or simply someone inspired by the power of ideas, this episode offers valuable insights and actionable advice. Join Kevin and Jeff as they explore how we can all contribute to preserving America's foundational values and creating opportunities for future generations. Tune in and be inspired to go big for liberty and leadership!



Dec 30, 2024
Dec 30, 2024
35 min
In this episode of the Going Big podcast, host Kevin Gentry delves into the strategies for achieving ambitious goals with renowned economist and cultural critic Tyler Cowen. They explore the critical elements of success, including cultivating a growth mindset, the importance of mentorship, and the power of embracing risk and overcoming complacency. Tyler shares valuable insights on identifying and pursuing their passions, navigating the trade-offs between credentials and pursuing their dreams, and leveraging the power of artificial intelligence to unlock new possibilities.
This insightful conversation offers listeners practical advice and a fresh perspective on achieving their full potential. Whether they are an aspiring entrepreneur, a non-profit leader, or simply someone seeking to make a greater impact on the world, this episode provides valuable guidance and inspiration to help them break free from limitations and achieve their most ambitious goals.
Subscribe to the Going Big! Podcast and discover how you can help business become a force for good in the world.

Kevin Gentry founded TenX Strategies to help great causes transform their effectiveness by 10xing their fundraising. He previously served as Vice President at Stand Together and also Vice President for Special Projects at Koch, where for more than 20 years he helped build the fundraising and marketing capabilities of organizations dedicated to the principles of a free society. With previous leadership roles at the Institute for Humane Studies, the Mercatus Center at George Mason University, and the Leadership Institute, Kevin brings a wealth of experience to solve big problems and a passion for advancing meaningful causes.







