wavePod

How to Lead (and Evaluate Good Leadership) with David Gergen (SB1733) - The Stacking Benjamins Show | Wave AI Podcast Notes

Back to The Stacking Benjamins Show

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

The Stacking Benjamins Show

Wed Sep 10 2025

Summary

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.

Loading summary...

Transcript

Joe Saul-Sehy (0:00)

This episode is brought to you by Navy Federal Credit Union. Tapping into your home's equity shouldn't come at a high price. That's why we offer our home equity loan options. We cover 100% of closing costs, which could save you hundreds. And with our fixed equity loans, you can consolidate debt and lower your monthly payments. Plus, we have no application origination fees. So if you want to get more out of your home base, learn more@navy federal.org Navy Federal Credit Union Our members are the Mission this episode brought to you by Progressive Insurance do you ever find yourself playing the budgeting game? Shifting a little money here, a little there, hoping it all works out well? With the name your price tool from Progressive, you can get a better budgeter and potentially lower your insurance bill too. You tell Progressive what you want to.

Doug (0:54)

Pay for car insurance and they'll help.

Joe Saul-Sehy (0:56)

Find you options within your budget. Try it today@progressive.com Progressive Casualty Insurance Company and affiliates Price and coverage match limited by state law. Not available in all states.

Doug (1:10)

This just in.

David Gergen (1:11)

Breaking news from Stacking Benjamin Recently, a.

Joe Saul-Sehy (1:15)

Man who was not only a Harvard professor speechwriter, but he also served four presidents died. David Gergen served Richard Nixon, Gerald Ford, Ronald Reagan and Bill Clinton. Because he served presidents in both parties, you can imagine how people thought about him. He was called left by right wing people and right by left wingers like it's some kind of football game. But I'll tell you, in my view, he was incredibly focused on one thing, building leaders and serving his country. So Joe, wait a minute. Isn't this greatest hits week? Politics on Stacking Benjamins not at all. The reason I wanted so badly to talk to David was because of this topic we're going to share with you today. Leadership. Being good at your job means leadership. Either knowing which leaders to follow or stepping up and leading yourself as an investor. So you'll hear next week from David Gardner, creator of the Motley Fool. Your job is to be able to evaluate leaders and and whether you should put your money in the concern that they're working. And as I mentioned, at the top two, David died recently and even though I spent only about 90 minutes of my life with him, I was much more deeply saddened than I thought that I would have been. He was a guy who I think gets it and you'll hear why on this episode. He also was a man who was incredibly generous. Here's a little quick behind the scenes story about the making of this one. So we first met, I was on my book tour and I set up My recording equipment. I'm in this hotel way up high, by the way, in downtown Chicago. We had an event that night, and when he met me online for our meeting, he was using an iPad, which made me go grown because our recording software doesn't support an iPad. So thinking quickly, and I have this nationally recognized great guest on. I instead said, you know what, David? Let's. Let's move over to Zoom. And I would use then my backup recorder. So I use Zoom infrequently, and I didn't record it on Zoom itself. I just used the system that I normally use as a backup. And later that week, I discovered that even after having done a thousand episodes and never had a problem, the one time I have this man who served four US Presidents on, and I don't run a backup, the file was corrupt. So I've got this. I've got this big decision. So I reach out and I'm like, yeah, we're cooked. In fact, it's funny, when I reached out, I reached out through one of his people, like, yeah, he doesn't have a lot of time. I'm sure he's not going to do it. And then, like, 45 minutes later, the woman writes back and goes, unbelievably, he said that he would do it and he'd be happy to. Although when he did show up to do it again, as you can believe, he was more than a little annoyed at first. And I'm laughing because we recorded again, and I'm so apologetic. I thank him profusely for doing it again, and I apologize for, like, the 10th time. And then David said, and this is why I think David was liked by so many people. He said, I can't do his voice. But no, Joe, I actually think we got it better the second time. And you know what? He wasn't wrong. You'll hear that today. A great discussion on leadership. And now you also know it was because he was so kind that we can actually play an episode for you at all. By the way, young Stackers, remember this takeaway. Mistakes happen, but don't let them happen twice. I now have backup for my backup in the case that we have to switch recording methods. And now I'm very happy to present to you our episode with the amazing late David Gergen, a man I would have loved to have known even better.

David Gergen (34:33)

Oh, I think it's very, very important early on to begin paying your dues. We are privileged to live in the country we live in. 99% of the world looks at us and still is in awe of what we've accomplished over the past. And they worry about our future. I think it's really important that we begin asking young people to do some service early in their communities, to get involved, to work with the homeless. That's something young people can do very, very well to work, say, with first responders to climate problems. When Hurricane Sandy came along, for example, young people went out there and really worked and set an example that has been followed in years since these big storms come. They're frequently positions that young people can play in doing it. So my argument is start early, get in the arena early, then begin to look for places where you can, in fact, make a difference in your community. Work your way up in your community after you've spent time in community, in your hometown, in your home district, in your home rural Area, your own farming area. After you've done that, then you can begin to volunteer for political campaigns or you can do other kinds of things. You can go to college. There are ways you can sign up for things and over time, give yourself time. Don't feel you got to run for Congress for, you know, 10 minutes after you leave college. I think this thing about paying dues is really, really important. I, I know a young man named Eric Lesser who came out of Harvard and he was a, you know, first class young man. I first met him when he was a sidekick to David Axelrod. The political analyst. Yeah. Then Eric was sort of the guardian at the gate, the guardian at this door. And Eric, when he came out, could have had almost any job anywhere. He decided to go to Worcester, Massachusetts and run for the state legislature and he ran as a state representative. Not pretty. Many people marvel go out and do that kind of thing, but he has excelled at it. He's done it now for several years, and he's now running for lieutenant governor of Massachusetts. He's got a good shot at it because people have a lot of respect for Eric. He's a straight shooter, but he put in his time. He really served his district well. And that was. That was the mark of a good leader.

David Gergen (43:09)

Sure. Well, I am a big believer in the power of humor. I think that we get through a lot of life. Yes. Lincoln said, if you don't laugh, you can only cry. Laughter helps. I think it is so important for leadership. People don't recognize, you know, that someone who's comfortable enough to, especially to tell self deprecating stories is pretty well anchored as a person, as a human being. And if you're so uptight you can't laugh at yourself, you know, you better find a different line of work than trying to be a public leader. So anyway, early in the Reagan presidency, he decided he wanted to give a fireside talk, in effect, an evening speech to the country about his economic plan and what he hoped to do. And you know, having a president come on and talk about the deficits is about the most boring thing you can put on television. Right. So with the question in my mind, I was a communications guy with how do we make this interesting? At that time we didn't have social media and we didn't have all the kind of gim cracks that you have to communicate. We had something very simple. So I said, Ms. Bridge, I'd like to get an easel and put it behind you. Sir, when you're giving your speech and midway through your speech, what we'd like you to do is to get up, leave your chair, keep reading the teleprompter, but go over to the easel, pick up the red felt tip pen and draw a line showing what will happen to the national deficits if in fact we don't embrace your program. Here's the danger we face. Would you do that? And he said, yes, I'll be happy to do that. And I said, well, sir, it was a 9 o' clock speech and you're very experienced at these things, but can you come over a little early so we can rehearse? Because you have to, you know, you have to be reading the teleprompter, you got to get up your chair, et cetera. And he said, no, no, I'll be happy to do it, David. So about 20 minutes to 9, he comes over and we sit him down. We have a rehearsal, and he gets up, draws the line. Everything is flawless. Nine o' clock comes. We got 70 million people out there tuned in. And he comes to that part of the speech where he gets up, goes over. And we had forgotten to do one thing. We forgotten to put the cap back on the red felt tip pen that he was going to use, draw that hard line. And so he said, here's what's going to happen to the deficits. And he took this pin and drew it across the chart and all you got was a screech. We had no line.

David Gergen (45:31)

You're watching this thing. And I was. I was standing about 35ft away behind the cameraman, the TV cameraman. I was updating my resume. And so I had an assistant TV guy named Mark Good, who had more foresight than I did. He brought a second red felt tip pen. So as soon as this happened, Reagan was standing up there sort of helplessly. Mark hits the floor, crawls across the Oval Office. Sigma Service is in there, and they're looking at him and looking at us and saying, what the hell? It's not in the playbook. White House staff member attacks prison. And Reagan was looking over, you know, looking around and saying, who's this jackass? Probably across my floor. So Mark crawl up to the desk, crawls behind the desk, gets up to rig his pant leg, holds up a second red felt tip pen and ringing. Gets this little twinkle in his eye and looks. Grabs a pant, looks into the camera and says, I think I'll try my pen again. And they drew a beautiful line. And we were thinking to ourselves, if that had been Nixon, who was a very uptight guy, and it really couldn't. His fingers weren't good in dialing on dial phone. You can imagine how they'd been in the age we live in now with everything, but if Nixon had been president, the speech would have been called off. We would have been thrown out on our butts in the Rose Garden, and the bombers would have been over Vietnam in the morning. There were a lot of moments like that, especially in the Reagan White House. It was people who love to sort of poke fun at each other. I'll tell you one more quick story, if you don't mind. There was a rule in the White House, it's every White House, that if somebody sends you a gift from the outside, you know, unsolicited you don't know this person. I sent you something. You got to mark it down in your notebook that you received it, and then you got to ship it out so it doesn't say in your office, you don't accept whiskey from people. You don't accept other things from people. So one day, Mike Deaver and I were standing around when this great big portrait arrived at Jim Baker's office. Jim Becker was chief of staff. The portrait must have been like 3ft tall and 2ft, 3ft wide. It was big. When Deaver and I got this thing, we said, let's grab this thing. We're going to be able to use it somewhere. We don't know where. Let's grab it. So we went and put it in my closet. But Baker never saw it. He had no idea that painting had ever arrived. So the day came when Reagan had his birthday and was going to fly off to Camp David for the weekend with Nassi. And he met down. Met about three of us down in the Diplomatic room just before you go out to the helicopter to have a little chat before he left for the weekend. So, you know, he had. He could size up and be briefed on the weekend. And David was there, I was there, Baker was there, and Deaver and I had this penny wrapped up in birthday paper. So we had this birthday thing sitting there, and Reagan was looking at it. Well, you know, what is this? And we said, Mr. President, we came a little late because we had to get this. Jim wanted to make sure you got this present before. Before you. We wanted to make sure he got this before. Before he went off to Camp David. And he said. He took it. And they said, oh, thank you, Jim. I really appreciate this. Should I open it? Baker didn't know what the hell's going on. He's really puzzled. I said, I guess so. Don't. Reagan opens it up. The gift from his chief of staff. There's a portrait of his chief, picture of him. Yeah. Baker went nuts.

David Gergen (51:23)

I do have a bias here, but let me say, first of all, I don't know much about these Corinthian schools. They flim flammed a lot of people. I think that 560,000 people and the $5.8 billion, whatever the number is that Biden is supporting, that seemed reasonable to me because they were, they were jipped, they were cheated and Corinthians obviously couldn't pay it. And what it meant for a lot of people who did pay and got nothing out of it. It's a burden they've had to bear in life. And so I'm sympathetic with people who got cheated. But the bigger issue for student debt is what happened to people that went to community colleges or went on to four year schools and how they pile up debts in order to go. I think it's really, really good that they, as a result of their endeavors and went to college, got an education. I think there's a much more productive country because so many people have gone on to school. So that's a good thing. But when it comes to the debt, when it comes to how to pay it back, I would feel more comfortable. And I think if I were on the receiving end, I'd be prouder if I did some work in exchange for canceling out my debt as opposed to sort of lining up at the cash window and say, just give me the money. There's a quality about that. If you borrow the money, you ought to have some skin in the game to help pay it back. I don't think you can pay. I appreciate you can't pay all your loans back and we ought to be helpful on that. But there ought to be some payment and some way to earn money. And I personally would link it to national service and that is, we'd like you to give a year back to your community. Find ways you can be helpful in hospitals or in schools. You know, you can be helping to deal with the dropout rate. You can work with kids who are younger. You can do a lot of different things in your community. Give us a year back in your community and we'll take a year off your college debt or your student debt. You know, give us two years, we'll take two years off. You can work your way out of this in something that will give. It will serve your community as opposed to just serving your instant needs. That's where I come from. I realize there's a bias there, but there ought not to be something for nothing kind of society. I don't think that's where we should be. I think pride comes when you earn it. Pride comes when you Pay your dues. Now, I think if you come out of college with a lot of money you owe, we should make it easy to pay your dues. But there ought to be a little work involved. Hi, I'm David Hirsch, and when I'm.