Going Big! with Glenn Youngkin

From the Basketball Court to the Governor’s Mansion: A Story of Risk, Reinvention, and Purpose

What does it look like to leave a successful business career and step into the political arena for the first time — and win?

In this episode of Going Big!, Kevin Gentry sits down with Virginia Governor Glenn Youngkin to unpack a journey that few could have predicted. Before he ever ran for office, Youngkin built a decades-long career in private equity, rising to become co-CEO of The Carlyle Group. But long before Wall Street, there was a different proving ground: the basketball court.

This is a conversation about discipline, mentorship, setbacks, faith, and the courage to take a leap when the timing feels uncertain and the stakes are high.

The Foundation: Faith, Family, and Formation

Youngkin traces much of his leadership philosophy back to his upbringing. Raised in a family that emphasized faith, service, and perseverance, he learned early that character matters more than titles.

Basketball became one of his first classrooms. Playing at Rice University, he absorbed lessons about teamwork, preparation, and resilience. Athletics taught him something he would later apply in business and politics alike: you can’t control every outcome, but you can control your effort, your preparation, and your response to adversity.

Those early mentors instilled a mindset that would shape the rest of his life.

Going Big in Business

After earning his MBA, Youngkin joined The Carlyle Group when it was still in its early stages. Over time, he helped scale it into one of the world’s leading private equity firms.

That growth required calculated risk-taking, long-term thinking, and an ability to navigate economic uncertainty. Leadership at that level meant building teams, making tough decisions, and maintaining trust in high-stakes environments.

But as he shares in this episode, success in business did not quiet a deeper question: What is this all for?

The Decision to Run

Few moves are bigger than leaving a secure, high-profile corporate career to enter politics — especially as a first-time candidate. Youngkin had never held public office before launching his campaign for governor.

The decision was rooted in conviction. He saw challenges facing families, schools, and businesses across Virginia and felt called to step forward. The campaign trail presented a new kind of arena, one where listening mattered as much as leading.

It required resilience, humility, and a willingness to engage with people across divides. In many ways, it was another version of stepping onto the court — prepared, focused, and ready to compete.

Leadership Under Pressure

Now serving as Governor of Virginia, Youngkin reflects on what leadership looks like when the stakes are no longer quarterly earnings but the well-being of millions of citizens.

The episode explores how private-sector experience translates, and where it doesn’t.

Governing demands coalition-building, long-term vision, and clarity of values. It also requires the discipline to stay grounded amid constant scrutiny.

Throughout the conversation, one theme emerges clearly: leadership is less about personal ambition and more about service.

Mentors, Risks, and Finding Your Contribution

As with many guests on Going Big!, Youngkin emphasizes the importance of mentors who shape perspective and push you toward growth. Coaches, business leaders, and trusted advisors played critical roles in helping him recognize his strengths and confront his blind spots.

He also speaks candidly about risk. Taking bold steps does not mean being reckless. It means aligning your skills, convictions, and timing — then stepping forward with courage.

For listeners wrestling with their own next chapter, his story offers a compelling reminder: the path to impact is rarely linear.

A Challenge to Go Big

What would it look like to examine your own life through this lens?

Where have discipline and preparation already shaped you? Who are the mentors who helped form your character? And what bold step might be waiting on the other side of your hesitation?

This episode of Going Big! is more than a political conversation. It’s a story about reinvention, purpose, and the courage to enter a new arena when the moment calls.

If you’re thinking about your next big move — in business, service, or life — this conversation with Glenn Youngkin is worth your time.