How To Lead (And Evaluate Good Leadership) With David Gergen (Sb1733) | The Stacking Benjamins Show Podcast

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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