How to Lead (and Evaluate Good Leadership) with David Gergen (SB1733)

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Sep 10, 2025

In this engaging conversation, David Gergen, a former White House advisor and Harvard professor, shares his insights on effective leadership cultivated over decades of service to U.S. Presidents. He emphasizes the importance of purpose and humility in leadership while revealing personal anecdotes from his experiences in the White House, including humorous moments and lessons learned. Gergen advocates for fostering new leaders amid today’s challenges and discusses how good leadership transcends perfection, blending practical advice with entertaining stories.

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ADVICE

Turn Economic Warnings Into Preparedness

Anticipate economic warnings by building a preparedness plan rather than panicking.
Use an investment policy statement and an order of operations to respond calmly to market risks.

INSIGHT

Young People As The Long-Term Hope

Young people represent the best long-term hope for national renewal despite present crises.
David Gergen is short-term pessimistic but long-term optimistic about their potential.

INSIGHT

Service Teaches Practical Leadership

Military service teaches humility, responsibility, and leadership beyond elite education.
Gergen found enlisted sailors often showed more discipline and professionalism than expected.

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What can you learn about leadership from someone who’s served four U.S. Presidents, navigated some of the most intense moments in American politics, and still believes the future depends on building more leaders, not fewer? In this Greatest Hits Week replay, Joe Saul-Sehy, OG, and Neighbor Doug welcome David Gergen—former White House advisor, Harvard professor, and author—to the basement for a masterclass on leadership that applies as much to your career and investments as it does to running a country.

Gergen pulls back the curtain on life inside the White House, from the early lessons he learned in the Navy to the behind-the-scenes moments that revealed the human side of Presidents. Along the way, he shares what separates great leaders from the rest, how to evaluate leadership in others (and yourself), and why service and responsibility are the cornerstones of lasting influence. Whether you’re leading a team at work, managing your family’s financial future, or just trying to be the kind of person others trust, you’ll find plenty here to sharpen your approach.

And because no visit to the basement is complete without some SB-style surprises, you’ll also hear stories of presidential humor gone sideways, a White House prank or two, and reflections on how good leadership isn’t about perfection—it’s about purpose. Plus, the guys tackle a listener question on investing without specific goals, and Doug tests the panel’s trivia chops with a leadership twist.

What You’ll Learn in This Episode:

How David Gergen defines real leadership (and how it’s changed over time)
The telltale signs you’re working with—or for—a great leader
Lessons from the Navy, the West Wing, and history’s most memorable leaders
Why building leaders is just as important as being one
Practical ways to evaluate leadership in politics, business, and investing
How a clear sense of service can make you a better investor and decision-maker

Questions for you while you listen (share with our Facebook group!):

Who’s the best leader you’ve ever worked for, and what made them stand out?
How do you evaluate whether someone is worth following—whether in politics, business, or life?
What’s one leadership skill you wish more people would develop?

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