
businessSep 10, 20251:13:32pending
How to Lead (and Evaluate Good Leadership) with David Gergen (SB1733)
About this episode
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?
Learn more about your ad choices. Visit podcastchoices.com/adchoices
Get every episode summarized
Each time The Stacking Benjamins Show publishes, we email you a written briefing from the transcript — the topics, who appeared, and any specific claims, with the ad reads skipped.
Email me new episodesFree for 3 shows. No card needed.
Hosts & guests
No transcript yet
This episode has not been transcribed. Request it and it moves to the front of the queue.
More episodes
More from The Stacking Benjamins Show

Why You Should Stop Saving for Retirement 3 Years Early (SB1826)
The Stacking Benjamins Show
Apr 8, 20261:16:37failed

You Don't Need a Huge Income to Build Real Wealth SB1825
The Stacking Benjamins Show
Apr 6, 20261:08:53failed

Building Your Personal Finance Curriculum (At Any Age) SB1824
The Stacking Benjamins Show
Apr 3, 20261:08:10failed

You Don't Need a Big Break to Become a Millionaire -- You Need a Better System (...
The Stacking Benjamins Show
Apr 1, 20261:05:35failed