Going Big! with Kevin Gentry

Episode Description
What does it mean to find your unique skill set when technology is moving faster than most people can process? In this episode, Kevin Gentry sits down with _Wall Street Journal_ columnist and innovation optimist Andy Kessler to break down how high performers and high agency leaders can thrive through the biggest technology shift of our time.

Andy lays out a simple but powerful framework for Going Big today: become relentlessly productive by doing more with less, pursue profit as a signal that you are creating real value for society, and most importantly, learn to spot major trends early so you can get the wind at your back. Kevin and Andy unpack how fast the world has changed since the smartphone revolution, why most people miss the first signals of disruption, and how to “see signposts in the fog” by thinking in five to ten year increments with scale, cost curves, and market elasticity in mind.

They also dig into what “high agency” really means in 2026, why artificial intelligence is a productivity powerhouse that rewards action over credentials, and how the democratization of tools is about to reshape careers across coding, customer service, medicine, law, retail, and education. Andy shares his own unconventional career journey, from Bell Labs engineer to Wall Street analyst to investor to writer, and explains why the best careers are not plotted, they are built by staying curious, staying loose, and learning how to learn.

If you want a more practical way to think about artificial intelligence, innovation, and your next big move, this conversation will help you stop fearing the waves of change and start riding them.

What happens when you stop trying to control a movement and instead design it to be owned by everyone?

In this episode of the Going Big! Podcast, host Kevin Gentry sits down with Asha Curran, Chief Executive Officer of GivingTuesday, the global generosity movement that began as a simple idea and grew into a year-round force for good across more than one hundred countries. Initially conceived as a counter-movement against Black Friday, #GivingTuesday was invented to encourage people to do good through donations and acts of service every year on the Tuesday after Thanksgiving. Asha breaks down how it went from a hashtag to an open source movement by rejecting old rules around branding, permission, and control, and choosing radical trust, co-creation, and civic agency instead.

You will hear how coalition campaigns and collaboration outperform competition, why small and medium nonprofit organizations often move faster than big institutions, and why people respond to authentic storytelling, not slick corporate messaging. Asha also explains how donors are influenced by social proof, why GivingTuesday creates net new giving instead of just moving donations around, and how generosity itself can be an antidote to anxiety.

The conversation closes with practical wisdom on mentorship, skill building early in your career, and simple ways anyone can live a more meaningful life through everyday generosity behaviors.

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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.

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.

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.