Podcast Summary: The Stacking Benjamins Show
Episode: How to Lead (and Evaluate Good Leadership) with David Gergen (SB1733)
Release Date: September 10, 2025
Featured Guest: David Gergen – Former White House advisor to four presidents, Harvard professor, author of Hearts Touched with Fire: How Great Leaders Are Made
Episode Overview
In this special episode, Joe Saul-Sehy and OG welcome legendary White House advisor David Gergen to discuss the essence of leadership—what it means, how it's cultivated, and why evaluating leaders is crucial both in life and as an investor. Gergen, who served under Nixon, Ford, Reagan, and Clinton, shares stories from his remarkable career and offers actionable guidance for aspiring leaders, with particular emphasis on empowering the next generation. The conversation stays away from politics and focuses instead on universal leadership principles.
Key Discussion Points & Insights
1. Why Focus on Young People?
[26:49]
- Gergen’s book centers on youth because, as he says, “they are a great hope for the future… [the] current generation who's in power is [not] capable of overcoming the crises we've been seeing.”
- He describes himself as a “short-term pessimist, long-term optimist,” believing that the next generation provides “glimmers of hope” despite current difficulties.
“The optimism comes from the quality of young people that I think are coming through the system who represent new hope and... fresh vision.” – David Gergen [27:33]
2. Gergen’s Early Struggles & the “True North”
[28:04]
- He talks candidly about his early aimlessness and setbacks—such as failed ambitions to be a pitcher (including a wild throw that broke a second-floor window!).
- Shares that finding true direction is often about “whittling it down”—learning what you don’t want to do.
3. Leadership Lessons from the Navy
[29:50]
- Serving in the Navy exposed Gergen to people from diverse backgrounds, teaching humility (“Within days after I left law school with honors, I was given a toothbrush and I was cleaning latrines”) and the importance of taking responsibility for others.
- Emphasizes that leadership is “not about glory” but about “making a difference” wherever you are.
“Leadership and good works can come from people who didn't go to a fancy school... the day will come when you're called on, if you're ready, if you're up to it, you can make a real difference in life by taking over a leadership position.” – David Gergen [31:19]
4. The Tarnished View of Public Leadership
[31:41]
- Gergen laments that kids today don’t aspire to the presidency due to cynicism and exhaustion with politics.
- Asserts the need for leaders to restore hope and “bring fresh energy and vision.”
“…If we give up hope, we're going to be lost.” – David Gergen [32:57]
5. Role Models: RBG, John McCain, John Lewis
[33:04]
- Gergen highlights diverse leaders to show leadership isn’t monopolized by one demographic.
- Discusses progress in representation across gender and race.
6. How to Become a Leader: “Pay Your Dues”
[34:33]
- Stresses starting early in community service, even in small local roles.
- Story of Eric Lesser: After Harvard, instead of a high-powered career, he ran for state legislature, earned respect, then advanced.
- Recommends avoiding rushing into high office: “Don’t feel you gotta run for Congress 10 minutes after you leave college.”
- Experience, humility, and building trust are paramount.
7. The Power of Bridging Divides
[36:48]
- Gergen recounts bringing people together even amid sharp divisions:
Describes attending a dangerous KKK rally in North Carolina as a young man, realizing later that approaching others as “exhibits” is reckless; real change comes from understanding different perspectives.
“We treated people at the KKK like animals in a zoo... we started them up. It was like waving a red flag in front of a bull and they came charging us.” – David Gergen [41:34]
- Applies lesson to today’s fractured society: “We look at the other side as if we're animals at the zoo and we bait each other.” [41:51]
8. White House Stories: Humor, Humanity, and Leadership
[42:39]
- Shares two memorable stories from the Reagan White House:
- The Dry Erase Marker Incident: During a nationally televised address, a missing marker cap meant Reagan couldn’t draw a vital chart line. Thanks to a quick-thinking aide, a replacement was sneaked in, and Reagan’s quick wit saved the moment.
- Reagan's Birthday Prank: A massive (and unwanted) portrait is gifted to Chief of Staff Jim Baker, with all parties playing along in good fun, showcasing the importance of humor and camaraderie at the highest levels.
“If you’re so uptight you can’t laugh at yourself, you better find a different line of work than trying to be a public leader.” – David Gergen [43:21]
9. On Student Loan Forgiveness and Service
[50:26]
- Gergen supports targeted forgiveness for students who were defrauded (e.g., Corinthian colleges) but prefers a broader approach where public service—such as teaching, community work, or national service—is exchanged for debt relief.
“There ought not to be something for nothing kind of society. I think pride comes when you earn it. Pride comes when you pay your dues.” – David Gergen [53:36]
10. Leadership as a Legacy and a Call to Action
[49:32, 53:36]
- Gergen insists it’s time for older generations to “step back” and “help the next generation,” passing the torch while sharing lessons learned.
- The episode (and Gergen’s book) are positioned as roadmaps for young, diverse leaders to rise.
Notable Quotes & Memorable Moments
- On Hope:
“If we give up hope, we're going to be lost.” – David Gergen [32:57] - On Service:
“It’s very, very important early on to begin paying your dues. We are privileged to live in this country… begin asking young people to do some service early in their communities.” – David Gergen [34:33] - On Bridging Divides:
“It would be healthy for a lot of our current students to go into the Bronx and go into Harlem and see what life is like... It's really, really important, I think, to listen to the voices and try to understand the experiences of those who've been less fortunate.” – David Gergen [42:00] - On Leadership Qualities:
“People don’t recognize… that someone who is comfortable enough to tell self-deprecating stories is pretty well-anchored as a person… Humor helps.” – David Gergen [43:21] - On Civic Engagement & Student Loans:
“Give us a year back in your community and we'll take a year off your college debt… You can work your way out of this in something that will serve your community as opposed to just serving your instant needs.” – David Gergen [53:02] - On Passing the Torch:
“It's time for us… to step back… We need to pass the torch to the next generation. And I think that they're a very promising generation.” – David Gergen [49:32]
Timestamps for Important Segments
- Introduction & Context: [01:10]–[06:53]
- David Gergen Interview Begins: [26:18]
- Focus on the Next Generation: [26:49]
- Leadership Lessons from the Navy: [29:50]
- Restoring Hope in Leadership: [31:41]
- Learning from Past Leaders: [33:04]
- How to Start Leading – Pay Your Dues: [34:33]
- Bridging Divides – KKK Rally Story: [37:35]
- Humor in the White House: [43:09]
- Student Loan Relief & Service: [50:26]
- Passing the Torch: [49:32]
- Closing Thoughts & Book Plug: [54:18]
Tone, Takeaways & Final Thoughts
The conversation was warm, self-effacing, and filled with gentle humor—Gergen’s humility and Joe’s signature lightly irreverent style combined for a lively, insightful dialogue. The hosts consistently kept the focus away from partisanship, underlining the universality of Gergen’s leadership lessons.
Key Takeaways:
- Leadership is cultivated through humility, service, curiosity, and learning from setbacks.
- Young people should be empowered to lead, but must also “pay their dues” and build experience.
- Humor, empathy, and bridging divides are essential qualities in any leader.
- True leadership can—and must—happen at every level: local, national, and personal.
- Even in times of cynicism and crisis, hope and renewal are possible with fresh vision and collective service.
Recommended Reading:
Hearts Touched with Fire: How Great Leaders Are Made by David Gergen
For those seeking actionable wisdom on leadership from one of America’s most experienced advisors, this episode is a masterclass—engaging, accessible, and full of practical guidance for both seasoned and aspiring leaders.