Speaker 1I raised $5 million from four investors in 1987. Today, Carlisle manages not $5 million, but $500 billion. How old were you then when you started Carlisle? 37. I said, geez, if I don't do it now, I'll never do it. Do you have any habits that you think would shock people? I always view myself as being from a blue-collar family in Baltimore.
Speaker 2But even like in year 10, you weren't thinking like, all right, I can breathe a little, this is going to work, I think I'm safe.
Speaker 1No, because if you're an entrepreneur, you always think something bad is going to happen. You still feel that way? Every day, 99.9% of the companies that started in the United States are not in business five years later. If you go back and look at anybody that built a company, they have self-confidence that is staggering. I met Jeff Bezos for the first time. He said, well, I'll give you 20% of the company that I'm about to build. Later, after the company was going somewhere, I said, we should have taken that deal. That was stupid. That stock's probably worth $14 billion now.
Speaker 2Can I ask you about seeing people get power? Well.
Speaker 3I was looking at this photo.
Speaker 1There's this photo here of, I think it's you and your parents. Yes. It's with President Carter. And, you know, I was 27 years old. I got a job as the Deputy Domestic Policy Advisor. I obviously wasn't qualified. I wasn't experienced. But in our system, if you work in a campaign and you win, you might get a job in the White House. And so my parents, who were blue-collar workers, never graduated from high school. When I got a job at 27 in the White House, you know, they couldn't believe it. And then I took them. And they meet the president, which is what that picture shows. And they were, you know, in awe because they were what we would call yellow dog Democrats. What's that? It's an old expression. It means that I'm a Democrat. And I would vote for a Democrat for a candidate for a president or for any office, even if it was a yellow dog.
Speaker 2So they're just hardcore Dems. Absolutely. What do you do your first month when you're in office? Because getting any type of new job is a big deal, particularly one where it's like one of the most powerful things on earth. What do you do your first month? Do you remember? Carter had a lot of promises.
Speaker 1And what I did is I worked on compiling what his promises were. See, there wasn't no internet then. And so Carter had wanted to know what he actually promised in the course of his two years campaign. Well, you have to go dig it out. Talks, interviews, questionnaires. What did he actually promise? And I got to sit in a lot of Carter's meetings because I knew his promises better than anybody. And so I would be able to object and say, Mr. President, it's a good idea. This person asked, but it's a violation of a campaign promise. Every administration, the current administration, every administration, has young people who are in their 20s or 30s who are working the campaign and they're energetic and eager and they get jobs and some of them will turn out to be great and some will turn out to be not as great.
Speaker 2But how did you figure out how to make good decisions? Because you are so young.
Speaker 1I mean, I didn't have a lot of policy experience. I'd worked on Capitol Hill for about a year or so. I didn't really have that much policy experience. My boss did. And then we hired a staff of really talented people. They were all young, but they were talented in their area, energy or environment or whatever it be. And then we'd have issues and we'd come up with positions. Remember, the president has policy positions that he wants to take. He wants to take because of campaign promises. So we would articulate, you know, how we could fulfill his promises.
Speaker 2So you were there for four years. What did you feel like when it was done?
Speaker 1Well, when you work in the White House, people come to you and tell you how great you are. Nobody says, yeah, you're an idiot. They come and tell you, you're a smart guy, you're great. And by the way, can you help me on this or that? And they always will say, and by the way, if you ever want to leave, call me because I will hire you somebody. But I always said, well, I don't want to be hired, but I'm going to be here for four years. When we win, I'll be maybe the senior domestic advisor. So in the next four years, after we lost the election, I started calling these people saying, you remember me, I'm the bright young guy you said I was so great. I didn't get calls back because you're out of power. People want to go and get contacted with the Reagan people. So I struggled for a while to find a law firm that would take me because nobody really wanted a junior White House aide who was a Carter person. And you're 32? I was left in White House at 31. So at 31, I'm trying to figure out, I want to tell my mother, look, your son is unemployable. Nobody wants a Carter White House aide. Not unlike the experience of the Biden. The Biden people have had. The Biden people have found it more difficult to get reestablished than they would have preferred. And when you lose an election, you're out of power. So as Harry Truman said, you want a friend in Washington, get a dog. Eventually, I got a job practicing law, and I realized I wasn't that great a lawyer. I didn't really like it. And so I started an investment firm about a year, a couple of years later.
Speaker 2I think the best way to become successful is to see how other people did it, whether you're going to copy them or just use it as inspiration, because then now you know what's possible. So starting at the age of 24. I did this relentlessly, and I was very methodical about it. And I created a spreadsheet where I tracked roughly 50 people who were uber successful. And I looked at the year that they were born, the year that they started their apprenticeship, and then the year that they started the first thing that made them successful. Finally, the year that they broke through. And I aggregated all this data along with the stories of what they did to be an apprentice and what they did to finally break through. And I put it together in a database and HubSpot went and found this thing that I frankly even forgot about. But it did change my life, and they resurfaced it. They made it even better, and they put it into a thing that you can download for free right now. So if you click the link in the description or click the QR code right here, you can see this database that I made when I was 24, and it changed my life. And so if you're looking to become successful or you're already successful and just want some more inspiration, check it out. How old were you then when you started Carlisle?
Speaker 1I was 37 because I read that an entrepreneur will start his or her first company between the ages of 28 and 37. Now, obviously, there's a market. Mark Zuckerberg's and Bill Gates' are the world that are different. But an average person will start a first company between 28 and 37. If you haven't done it by 37, I read, you probably will never start a company. So if you have an entrepreneurial instinct, you better do something by the age of 37 was what I read. And I was then 37. I said, geez, if I don't do it now, I'll never do it.
Speaker 2Did you think, like a lot of times when people start businesses, they're like, how much runway do I have?
Speaker 1When I started Carlisle, I was married. When I left the White House, I wasn't married. I got married a couple years before I started Carlisle.
Speaker 2So you had the pressure of, like, I need to provide.
Speaker 1Well, you have some pressure, but, you know, there's pressure. But the pressure of getting a company off the ground is considerable. As you know, you started your own company. You never know when you start a company if you're going to be able to pay the rent the next day or next month. And are people going to want your services? You don't know.
Speaker 2Yeah, when I started my first company, that was one that led to some success. I was lucky because I was 24 or 25, and I was single, and, like, I only spent $1,500 or $2,000 a month. And so, like, I had saved up maybe, I don't remember, $50,000. So I'm like, I'm good. I have 36 months or something like that.
Speaker 1Well, remember, 99.9% of the companies that started in the United States are not in business five years later. 99.9%. So it's a small percentage of companies that are there five years later and a very small percentage that are there 10 years later. So most companies that are started just don't work out.
Speaker 2What did you do the first handful of weeks after you decided to start the company?
Speaker 1Well, I had to recruit people and recruit people. And then we raised... And then I had to raise money to get a start. I raised $5 million from four investors in 1987. Today, Carlyle manages not $5 million, but $500 billion. So it's grown to be one of the larger private equity firms in the world with the help of a lot of people. But I did that for many, many years. Who was your first few hires? Well, I had a couple partners. I hired a person who had been the chief financial officer of a company called MCI, which was a long-distance telephone company. And he became my co-CEO with me over for some 30 years. His name is Bill Compton. And we hired another person, a senior officer from Marriott. So we hired a number of people at the beginning, four of us at the beginning. And then we grew it. The companies Carlyle controls have been a million and a half employees. And Carlyle itself has got about 2,300 core.
Speaker 2It sounds like whenever I started my last company, the people who are in this company, the people who I initially hire, they're basically like rejects. It's like smart, ambitious, rebellious. But it sounds like the people you hired early on were very pedigree.
Speaker 1Well, they have pedigrees in the sense that they had went to good schools. I was probably a sucker for hiring people that went to good schools. But in the end, everybody is leaving somewhere because they're not happy there and they're not thinking it's working well for them. So everybody is really incented to try to get a better position in life. And a lot of people at the age of 20 or 30, they realize the job that they currently have may not be so great. So they take a chance. And, you know, some people work out and some people doesn't work out.
Speaker 2I know your job. Your job was recruiting and your job was helping fundraise. And I already know because I've listened to so many of you. You're very charming and you're very persuasive. You're very good with words.
Speaker 1I don't know about that, but I would say that my partners had MBAs. I didn't have an MBA. So they really knew the investment world. So I figured, okay, they can really assess deals better than I can. What I'll do is I'll raise the money and then I'll ultimately recruit people. And then I'll be the face of the firm because I was better at that than maybe they were. And so that's what I did for 30. Plus years run around the world, raising money and then recruiting people to build our new firms. So what we did that was different was we had multiple funds in private equity. Historically, you had a buyout fund if you're a buyout business and you had a venture fund. Every four years, you raise a new one if your track record was good enough to justify it. I came up with the idea of having a buyout fund, a growth fund, a real estate fund, a debt fund that had multiple funds. And then I had the idea of globalizing. I have a fund in Europe and Asia, Japan, so forth. That was novel at the time. But to do that, I had to run around the world recruiting people and raising the money. And so that took a lot of time. Do you remember how, so you got your first $5 million fund. How long did that take to raise? Well, it was one person who was a friend of mine who helped me raise the $5 million and was from four investors. And we did things what's called deal by deal. We didn't have money to do a big fund. So we'd find a deal and then go raise money for that deal. If it worked out, then we'd go raise money for another deal. And we did that for a number of years before we raised our first fund, which was $100 million. conform as a billion. And so we got bigger.
Speaker 2- How did you pay your team then? if you don't have a fund, if you're doing deal by deal?
Speaker 1Well, it's harder because if you do a deal by deal, you have to go to people and say, here's a good deal. Give me some money for it. And they say, I'll get back to you. I'm not sure. So it takes time and it's hard to do what we were trying to do at the time because we were buying publicly traded stocks and you can't tell people here's the opportunity because they could trade on it if they didn't give you the money. And legally, I guess they could trade on it that they shouldn't have. So it took a while to get money, but that's true of everybody. Anybody that's built a successful company is always going to have a hard time at the beginning. And we had a hard time at the beginning, but Blackstone and Apollo and KKR, they all had similar stories having no money at the beginning. And then they started Blackstone, which are the biggest of the private equity firms these days. Steve Schwartzman wrote in his autobiography that they got turned down by 97% of the people they went to to raise their first fund. Yeah, and the first one was huge, wasn't it?
Speaker 2It was maybe 800 million, I think. Yeah, it was huge. But what I'm curious about, I don't think that you don't talk too much about your entrepreneurial side. And I'm always very curious about that. Do you remember the scrappy stories of what your first office looked like?
Speaker 1When I started the firm, we didn't have any money. We had no credibility. So there was a new office building that had been built in Washington. It looked like a building that was a classic building for a wealthy kind of set of tenants. And they had a little space left because they had filmed a movie called Broadcast News with Jack Nicholson in that space. So the space was now available. I said, I would take that. I would take the space. It was 5,000 square feet. And the leasing agent said, look, you can have another 5,000 if you want. You can have an option for 5,000. I said, no. I didn't take it. I said, I don't want it. She said, it's free. You just sign the thing here. You get the option to have 5,000 square feet more. I said, I don't want it because I don't want to be tempted to ever grow that big a firm. Why didn't you want to grow that big? At the time, I didn't know much about business compared to what I know about government or I knew about the practice of law. And I was afraid if I took a bigger space that we would try to expand too rapidly. So that's probably why we didn't do it. Then later, we had to expand. And now we're the biggest tenant in the building.
Speaker 2About one night a week, I'll be laying in bed with my wife, you know, doing pillow talk. And I'm like, you know, one day if we nail this, this, and this, in the next 10 years, maybe we can be this. Or maybe in 50 years, we could be this. And like you like have these like, you know, vision sessions. Were you doing that with your spouse?
Speaker 1Every day was a challenge because we're trying to start a firm. Remember, private equity was not as big as it was today. In fact, the phrase private equity wasn't even invented yet. We were in Washington. Washington, D.C. was not New York. People didn't take you seriously. And people ask me, why did you do it in Washington? Well, Senator Everett Dirksen, used to be a Senate minority leader, said famously, when you're getting kicked out of town, get out in front and pretend you're leading a parade. What does that mean? It means take advantage of the situation you're in. So I said, we're in Washington. We understand the company's heavily affected by the federal government better than the guys in New York. Maybe it was true, maybe it wasn't. But it sounded good, and some people gave us money.
Speaker 2You're the second. You're the second person in the past couple weeks. So over here, we've had Ray Dalio in recently. And I asked him the same question. I was like, when you were first getting Bridgewater going, what were some crazy ambitions? Did you say, oh, it would be awesome if we made $100 million or $1 billion or had 10,000 employees or whatever? And he was like, I just wanted to make $100 grand a year so I could pay for my family. That was my goal. In Ray's case, I think he started the business out of his apartment. Yeah, and he had to ask his dad for money one time because he went broke. He had to borrow money from his father, if that's correct. Yeah. And so it's funny hearing you say this because you've built such an amazing company that I can't believe that there was no aspirations early on just for the sake of motivation.
Speaker 1You know, if you have the grandiose expectations or plans at the beginning, you might be fooling yourself. I don't think Bill Gates, when he started, think he was going to build what he built or Mark Zuckerberg or all these others. For example, Mark Zuckerberg was at Harvard. My now son-in-law was one of his classmates. And I heard about the opportunity. This guy was building his company, and they asked me to invest. And I said, I'm not going to invest. And that's a dating company because the original idea was simply to help people get dates at Harvard. You have pictures of people, their faces, and you can do it through social media. And then they thought maybe they'd expand it to Yale or Princeton. That was it. The idea of doing non-students really wasn't even surfaced then. I don't think Mark Zuckerberg actually thought he would ever build what he built.
Speaker 2Yeah, I think I remember some awesome story of Jeff Bezos at a pitch. He goes, look, if we really nail this, I think we can make $100 million a year.
Speaker 1Look, I saw Jeff at the beginning because he had to get a bibliography of books in print to be able to sell books on the internet. One of our companies had a bibliography of books in print. He came to rent it from us, and we said, we don't rent it. He said, well, I'll give you 20% of the company that I'm about to build. And our guy said, we don't want a piece of an illiquid company, a startup, that's not worth it. We want cash. Ultimately, we agreed to, I think, $100,000 a year for five years. We rented in the bibliography.
Speaker 2Wait, you owned a company that was a book publisher, and it had a book that had a list, a list of every book ever written? And the offer was 25%? It was 20% to 25%.
Speaker 1Later, after the company was going somewhere, I said, we should have taken that deal. I flew out. I met Jeff Bezos for the first time. He had one office, and he was doing the books himself, and he would take them to the post office every night. It was very small. And I said, you know, you're going to compete against Barnes & Noble. He says, yeah, but I understand how to do this better than they do. And so I said, this guy is not going to really make it. I said, look, we'll take some stock now. We'd like some stock. 20% is okay. He said, well, David, that was a couple years ago. Now I don't need you quite as much, but I'll give you some stock. We got some stock, but then we sold it at the IPO. That was stupid. That stock is probably worth $14 billion now.
Speaker 2Did he have any attributes back then that you saw this guy is going to be the guy?
Speaker 1He's very smart and had a lot of self-confidence. And he said he had a lot of good computer skills, and maybe he did. I couldn't judge that. But he was very driven, very smart, hardworking, like a lot of entrepreneurs. Entrepreneurs, people that build. People that build companies are not shrinking violets. If you go back and look at anybody that built a company, they have self-confidence that is staggering. Because if you're a shrinking violet, you're not going to build a company. Bill Gates is a young man, and Jeff Bezos or Mark Zuckerberg or Steve Jobs, the enormous amount of self-confidence, and that's what it takes to really build a company. Did you have that? I didn't have as much as they did because I didn't think I was as smart as they were. But I was surrounded by people that had more. I recruited people that knew more than I did.
Speaker 2You got really good at not just recruiting talented people, but you got really good at recruiting big shots. Like you had a bunch of big shots who were, I don't know the right terminology, they're like advisors.
Speaker 1Well, what happened was when we were starting the company, or right after we started it, they started in 87. Ronald Reagan's presidency was over in 88. And a former law partner of mine said that a man who had been the secretary of defense was going to go on a lot of corporate boards. But in those days, if you were not a lawyer, you couldn't. You weren't a law firm. So he was looking for a place to be a base. And my former law partner knew about what I was doing. And since we weren't a law firm, he said, why don't you interview Frank Carlucci, the former secretary of defense, or about to be a former secretary of defense, and he can join your firm. He's going to be on a lot of corporate boards, and maybe he can open some doors for you. So we interviewed Frank Carlucci. He joined us. And then he could open doors that I couldn't open. He was a former secretary of defense. Four years later, Jim Baker was leaving as secretary of state. But while this is the ultimate great man, the man of the world, secretary of state, secretary of treasury, White House chief of staff, and I was able to recruit him.
Speaker 2How many other options did they have? Like, why would they trust, like, a startup?
Speaker 1I mean, they always had other things that we weren't doing. In Frank Carlucci's case, he was joining, like, six or seven corporate boards. That was his main activity. In Jim Baker's case, he went back to his family's law firm. He was a partner in there, but he was also a partner in our firm. And then after Baker, we had Dick Darman, who had been one of his protégés, who had been the head of OMB. And then later, George Herbert Walker Bush, former president of the United States. Became a, uh, an advisor to us. And then John Major, former prime minister, became an advisor to us as well. So we did open doors with these people because if your last name is Rubenstein and you go to the Middle East to raise money might not be as compelling as if you go with Jim Baker.
Speaker 2Do you remember what the pitch looks like or sounds like when you're, when you're swinging above your weight?
Speaker 1Oh, it's saying, look, we're a firm in Washington. We understand, uh, companies heavily affected by the federal government. We're buying an aerospace defense company. We have a former secretary of defense and, you know, in the end, uh, you have to build your track record. So if you did one deal and it exited well, then you can go and use that to say, we're going to do another deal similarly. So it worked out, but we made some mistakes and everybody makes mistakes and, you know, but it worked out.
Speaker 2Yeah, that's crazy. But it seems like you guys had like a pretty good trajectory. Do you remember any times where you're like, this is not going to work?
Speaker 1One time we had a limited amount of cash and then we were trying to buy a company and it was in bankruptcy court. We're trying to buy a bankruptcy and we basically spent all our money trying to buy it and then we lost in bankruptcy court. So we'd spent all our money. We didn't get the company. We had no more cash. So we were, we said, Hey, what are we going to do to meet the payroll? But in the end, we actually got the company and the end, uh, turned out to be a very successful deal. But, you know, I remember waking up in the middle of the night and thinking, Hey, how am I going to pay the rent?
Speaker 2What year or how many years into the company did you feel like you personally were like, all right, I'm financially stable.
Speaker 1Maybe yesterday. It takes a while. I mean, uh, when we were building the company, we ultimately. Um, sold a piece of it to CalPERS, I think about 5% to California, uh, retirement system. And they'd value the company at something being worth like $2 billion. The company was worth 2 billion or two and a half billion. Nobody thought that a, a private equity firm in those days had franchise value and could be sold, but we sold 5% to CalPERS. Uh, that was probably 2009 or something like that. And then a few years later we sold, uh, seven and a half percent to Mubadala, which was a Abu Dhabi investment arm that. and that value of the company had been worth $20 billion. And then we later took the company public.
Speaker 2But even like in year 10 or so, you weren't thinking like, all right, I can breathe a little. This is going to work. I don't know how well it's going to work, but it's actually going to work. And personally, I think I'm safe.
Speaker 1No, because if you're an entrepreneur, you always think something bad is going to happen. And so I'm always worried that something bad is going to happen. Tomorrow, somebody will do something they shouldn't have done or a deal won't work out. So I never felt comfortable. You know, I tend to be a workaholic a bit, so I'm always working on things. And I'm always thinking, what can go wrong? You still feel that way? Every day. Really? Look, I'm always thinking bad things can happen. Maybe that's what entrepreneurs do because you have to have certain self-confidence, but you always have to assume something bad can happen. You have to protect against it.
Speaker 2But it seems like you've had good partners. I'm highly neurotic. My business partner who runs Hampton is not neurotic at all. And he's very calm and steady. And it's like the greatest pair ever because he's the only one who I will be neurotic with.
Speaker 1Well, I have two people that I really built the company. And one of them is now 80 years old and has all dark hair and then have one gray hair. So he may be not as neurotic as I am. And then Bill Conway has gray hair, but he doesn't seem to worry about some of the things as much as I do, maybe because he's more self-confident about his abilities to be an investor. But look, you're always worried something bad is going to happen. I'm worried every day. I'm now the principal owner of the Baltimore Orioles. I'm worried every day that something bad can happen. What are you worried about with the Orioles? I want to make the playoffs. And we're now one game out of the playoff. Game away from being able to get into the playoffs, but one game behind the Cleveland Guardians. And then there are other teams that could catch up to us. So I'm always worried that I didn't do a good enough job in helping the team.
Speaker 2I get worried about looking stupid on the internet. And the comments, I act like they don't bother me. They do. Do you get bothered by comments or people criticizing an interview?
Speaker 1Advisors have trained me not to read social media because you're inevitably going to find people saying something critical of you. Does that bother you? Well, nobody wants to be criticized, so I tend not to read the social media. Sure. So I generally don't go into social media.
Speaker 2I was reading about how I think you said you were traveling like 200 plus days a year. So how old were your kids when you were doing that? And how did you balance being a good dad?
Speaker 1Well, it's always a challenge, of course. But as you know, all three of my kids have MBAs, and they all are in private equity. So you can say I either did something wrong or did something right. But look, parents who are... who are driven and have businesses that require the travel, you have to depend on your spouse and other people that help make sure the kids get grown. And when I came back on weekends from my travels, you know, I would try to spend time with them.
Speaker 2Do you get to work with them on a weekly or daily basis now? Like, are they part of an organization that you're a part of?
Speaker 1No. I have a family investment office. And very often, a family investment office will be something where you can bring your children to work in it and so forth. Some people do it that way. I didn't want to do that. So... They have their own businesses that I've helped support, but now they're kind of on their own. And I have a family investment office, which is owned largely by the people that work there, professionals, and I own a piece of it as well. And then when I drop dead, my children will get something probably out of it. But I'm committed to giving away most of my money. I was an early original signer of the Giving Pledge, and I've given away a lot of money. And I intend to give away the bulk of what I have left.
Speaker 4Hey, let's take a quick break. You know that feeling when strategy is done, the brief is written, and everyone's aligned, and you realize someone still has to sit down and actually create all the content? That someone is usually you, and it's due tomorrow. Well, the Breeze Assistant from HubSpot can help. It works right inside HubSpot. You can draft a campaign copy, blog posts, emails, all in your brand voice, all using your actual customer data. So you don't create just content. You create content that converts. Check out HubSpot.com, the agentic customer platform for growing businesses.
Speaker 2One of the reasons I respect you is because you seem like a very fulfilled person. Have you ever thought about... Who you know in your life who seems fulfilled and has a really rich life, like a well-rounded, rich life? Because a lot of times, successful people, you don't want to trade spots with them.
Speaker 1Well, there are very few people who everything works perfectly for. There may be some people like that, but everybody's got their challenges. And this weekend, I hosted in Nantucket friends of mine from high school from 60 years ago. When I was growing up, I wasn't a great athlete. Some of the people I had at my home this weekend were great athletes. Some of them were really good athletes, and some of them were really, really good people. And I think that's one of the reasons why I've always been proud of myself. And I think that's the reason why I've always been proud of myself.
Speaker 2And I think that's one of the reasons why I've always been proud of myself. And I think that's one of the reasons why I've always been proud of myself. And I think that's one of the reasons why I've always been proud of myself. And I think that's one of the reasons why I've always been proud of myself. And I think that's one of the reasons why I've always been proud of myself. And I think that's one of the reasons why I've always been proud of myself. And I think that's one of the reasons why I've always been proud of myself. And I think that's one of the reasons why I've always been proud of myself.
Speaker 1Well, there are a lot of people. The person who was in my firm, I thought his professional career was extraordinary, and that was Jim Baker. Great job in the federal government and a very well-respected person. You know, there are lots of business people that I've looked at and admired over the years. And people have great personal lives, professional lives, and the people want to emulate. Yes, there are a lot of people like that, but there's nobody out there that's perfect.
Speaker 2I talked to someone who worked with you at Carlisle. He was an associate. But he was saying, I love working for David because I think he's lived in mostly the same house for a very long time. When you walk into the office, his office, you don't see, like, a lot of fancy stuff. He's pretty low-key. When he leaves the office, there's not, like, a limousine driver or whatever you would think of, like, the stereotype. And he said that that's one of the reasons why I really respect him and I really like him is because he seems like he's still very down-to-earth, regardless of how successful he's got.
Speaker 1Well, I always view myself as being from a blue-collar family. And I always, you know, realize that neither of my parents graduated from high school. I got lucky in life. And, you know, you wouldn't have predicted what would have happened to me. And, you know, I've tried to give back to society, and I've given a lot of things into philanthropy, and I've tried to chair a lot of nonprofit boards and so forth that kind of give back to society. But, you know, in the end, you know, I'm not that fancy a person, I guess.
Speaker 2When we had Lloyd in, he was like, he told the story. I think his father was a post office.
Speaker 1His father had the same job my father had, postal clerk. His father did it in New York, I think Brooklyn, and my father did it in Baltimore. I forget if his father was a high school graduate, but my parents didn't graduate from high school, and my father came back from World War II. The only job he could get was this postal job, and that's the job he had his entire life.
Speaker 2And he told the story. He was like, I still have the lower tier of Netflix. He was like, it's kind of funny. He was like, I could afford these things, but I definitely like being broke or not having a lot of money. At a young age, it still has impacted me. Does it still impact you? Do you have any habits that you think would shock people?
Speaker 1You know, I still go to the same barber for like $15 to get a haircut or something in my neighborhood. So I am wealthy, but not so wealthy that I am, you know, I have yachts. And I don't know, I guess I'm, you know, somewhat old school, and I still have this suit I'm wearing. I've had it for like 10 years. The trick is being able to fit in your suit, say, for 10 years. That's the trick.
Speaker 2How many do you have? Because that's all. That's the only thing I've ever seen you wear.
Speaker 1I have a lot of suits, and it's an interesting phenomenon. Today, in the business world, not wearing a suit is considered more normal. But I guess my father was a blue-collar worker, and he had this obsession with never wearing a tie. He just thought ties were terrible. And I guess to kind of show that I was achieved more than he had achieved, I guess I bought a lot of suits, and I have a lot of ties, and I'm amortizing them. I'm still wearing the same ties and suits I've had for many years.
Speaker 2Well, it looks good. I mean, that photo when you were 27, you looked sharp there. By the way, they dressed, the presidents and government official, they dressed amazing during that era. Like, when you look at Ronald Reagan's suits, he was a sharp dresser. He was very good at dressing compared to a lot of people now. He was an actor, and he wanted to look, you know, good.
Speaker 1And Carter was, you know, Carter was a little cheaper than Reagan was probably. He had his suits made in Plains, Georgia or someplace like that. And, you know, but he wasn't a fashion plate, I think it's fair to say.
Speaker 2Can I ask you about seeing people get power? Because I've read, I think, is it the governor of Virginia was an intern with you guys?
Speaker 1Glenn Youngkin worked at Carlisle for 25 years, and he got elected governor, Glenn Youngkin, yes.
Speaker 2And then you also know world leaders, you know, a lot of really successful entrepreneurs. What is it like when you see someone go from just knowing them as a young person or someone without as much power, money, or success, and then seeing them become, like, the man? Is there something that power can change you?
Speaker 1Power does change some people. Glenn Youngkin, I hired him pretty much out of McKinsey, right out of Harvard Business School. He worked for us for 25 years, and then he decided to leave and run for governor. I didn't think he would get elected because he'd never been in politics before. He got elected, and all of a sudden, people were talking about him being potential president of the United States. So, look, I met a lot of people over the years who I thought were modestly talented or very talented, and you never know which ones are going to be the ones that actually go on. You don't think you can predict that? It's impossible. You know, you just have lucky breaks. I mean, who would have predicted Bill Gates dropping out of Harvard and is going to build a company that became Microsoft? Or Steve Jobs didn't even go to college. Who would have predicted any of these things?
Speaker 2Yeah, but there are some, like, traits or little antidotes or stories that you hear about these guys where they just, like, they sound like animals. Like, I heard this story, and a lot of these stories, they could be myths at this point, but it was a story about Bill Gates, and apparently he didn't have a radio in his car because he said, that distracts me from thinking about Microsoft just in my 20-minute drive. And, like, you hear these things. And you're like, I don't know if it's going to work amazingly well, but, like, you got something where you seem a little bit unstoppable.
Speaker 1Well, but there are a lot of people that have those qualities, and they don't make it. You know, you have to have some luck, too. Microsoft, you know, had some very good fortune at the very beginning. IBM, in effect, made, I think, a mistake. When IBM was looking for a software or operating system for its PC, they hired Microsoft to provide it, but they didn't own the light operating system. Had they owned the system, Microsoft wouldn't have made all that money by selling the effect operating system to other computer operators or by building a whole system of software. If IBM had said, well, buy Microsoft at the beginning because they have the operating system, it would have been different.
Speaker 2Can I ask you about owning all these awesome documents? Yeah, sure. How much have you spent in some?
Speaker 1I've never added it up. I don't really honestly know. But what happened was I stumbled into buying the Magna Carta. I didn't really intend to, but somebody told me it was about to be sold, and it was the only copy in the United States, and it was the only one in private hands, and it would leave the country, blah, blah, blah. So I bought it. And then I put it on display at the National Archives on a permanent display, and then I... I started getting other historic documents, the Emancipation Proclamation, Declaration of Independence. I owned, I think, more rare copies than anybody of that. And then the 13th Amendment, which freed slaves, and then other historic documents. And I started fixing up buildings at the Washington Monument, Jefferson Memorial, Lincoln Memorial. And the reason is I want people to know more about American history. And if you have original documents, people may be more likely to look at them, learn more about history. And the same is true of these buildings. If they're restored, people might go visit them and learn more about American history.
Speaker 2When you're bidding... On them?
Speaker 1Are there other bidders, typically? Well, there typically are, sure. When you have, like, when I bought the Magna Carta, I was bidding, but I was in a room. They put me in a little room at a telephone, and they said, aren't you going to bid? The auction's almost over. And I said, okay, I'll bid. I put a bid in, and they said, sold, right away. I don't know if anybody else ever bid. I never found out. How big is the market, though, of people buying these documents? Yeah, it wasn't as big as it's now becoming, because now some art buyers who spend $300 million for a painting... Are now getting to buy documents for a lot less, and they've now gravitated to that, so there's more competition. And look, the Declaration of Independence, because of the semi-quincentennial, has become a document of greater interest to people, so the prices have gone up dramatically to buy these historic copies.
Speaker 2Well, I think it's Walter Isaacson. He's got a new book about the greatest sentence ever written, and it's awesome. And I didn't realize how amazing the Founding Fathers were when it came to a bunch of different stuff, like thinking really long-term. The idea of, like, we hold these truths to be self-evident, that's kind of interesting, and that it's a very... It's a self-amending document. Like, there's a lot of, like, really interesting parts. Did you think that when they were writing this, that they thought someone is willing to pay all this money to own this and save this and, like, cherish it?
Speaker 1Well, they didn't treat the document that well. When the Declaration of Independence, after it was drafted and signed, they basically folded it, they hid it, placed it, they put it in sunlight. No, I don't think they thought that at all. Wow. Not at all. Until 1823, when John Quincy Adams was Secretary of State, he realized that the document was fading so much, they better get some copies or sooner or nobody would be able to see it, and they made copies then.
Speaker 2Yeah, I often think about that, about what they were, like, where their mind space was when they were doing it, because it's pretty amazing. How old was Thomas Jefferson? I think 33? 33.
Speaker 1Remember, there were 3 million people in the United States at the time of the Declaration of Independence, and half a million slaves and two and a half million whites. And it was on the eastern seaboard, and nobody really thought that. Nobody thought this country would amount to that much, even if we won the war, which no one thought we would do. But even after winning the war, it was not clear the country would survive. Jefferson didn't think it would survive for more than 20 years. He said that? He did. He wasn't at the Constitutional Convention, but he wrote with Madison back and forth,
Speaker 2and he kind of thought 20 years would probably be about what it would take. And so that's kind of like a common trend of what I was asking earlier about Jeff Bezos and how it's kind of hard to, like, have big ambitions when you're just getting going.
Speaker 1Yeah, look, the Founding Fathers, if they were to come back today, they'd be astounded that the country that was a tiny country on the eastern seaboard has been for at least since World War II the most powerful country in the world in every category you can mention. They would never have dreamed that.
Speaker 4Today's podcast is brought to you by my friends at Mercury. They make the world's best banking product. I think you know this already. I use Mercury for all of my businesses. I think I have, like, maybe seven or eight businesses. We use Mercury as our business banking across all of them. And now they actually just launched a personal banking account. So I have my... I have my personal account there. I moved off of Wells Fargo and Chase. I'm just all in on Mercury. Why? I like products that are easy to use. I like products that get me and the problems that I have. So, like, very easy to make a joint account with my wife. Very easy to spin up virtual cards. One click and I get savings yield. It just has all the stuff that I need in one place. So if you're looking for the best banking product on the market, it's definitely Mercury. I will fist fight anybody who disagrees with me on that. Go to mercury.com slash personal and learn more. Mercury is a fintech, not an FDIC insured. Mercury is a fintech, not an FDIC insured. Banking services are provided through Choice Financial Group and Column NA, members FDIC.
Speaker 2One of my favorite parts about reading history is that there's, like, a handful of rules or axioms or trends that, like, tend to repeat themselves. For example, I was reading about Winston Churchill and he was talking about how he was... He, like, said it, like, to someone. He was like, I think the world might end. Like, and, like, it was just, like, funny that there was, like, different periods of time where people always think, like, the worst is going to happen and we end up working out. Are there any, like... Sets of rules or axioms or trends that you have seen repeat themselves over and over again that have helped you deal with whatever you're dealing with at the current time?
Speaker 1Well, you're always worried about things. I worry about the federal debt. For example, we have $40 trillion of federal debt. Our ability to pay this off is virtually non-existent. And so what we're really going to have to do is, in effect, pay it off in devalued dollars and the dollar will go down in value almost certainly. And you always worry if you have children, as you do, right? That are they going to grow up in a world that's going to be more difficult than the world that you grew up in? And will they be ready to deal with the world? Are they going to be educated appropriately? And what are they going to turn out to be? And it's a more complicated situation. Every parent worries about whether the world will be good enough for their children to kind of be able to do what they did. So I've read a lot of great books. And the reason I do it is, one, I have some TV shows where I interview authors and I feel it's a courtesy to the author to read the book. Yeah. Secondly, I actually... Generally, interviewing people about books I am interested in reading, this kind of forces me to do it. Third, it's my anti-Alzheimer's device. Because they tell you when you reach a certain age, if you don't have a genetic predisposition to Alzheimer's, you could still get it by maybe your brain is allowed to not be exercising enough. They tell you to learn a musical instrument, do a crossword puzzle, learn how to do crossword puzzles and do that frequently, or learn a foreign language. I'm not good at any of those things. So one of the things... One of the things I do is I read a lot and I interview people. And when you interview people, you've got to keep your brain sharp. As you can see, you've got to go back and forth, listen to what the person is saying, think of the next question while you're listening to the person, and you've got to keep your brain active. And it's a good way to keep your brain active when you reach my age. So I do it as my anti-Alzheimer's device.
Speaker 2What are some of the favorite things that you've read in the last six or eight or 12 weeks?
Speaker 1I've read a book on Roy Cohn. It's called, I think, "American Scoundrel," which is a really good book by Kai Bird, a previous... Edward Oppenheimer that won the Pulitzer Prize. And it's just amazing what Roy Cohn was and so forth. Recently read Beverly Gage's book on J. Edgar Hoover, which is an astounding book and won the Pulitzer Prize, a really terrific book. So I'm always reading books. And one of the programs... I have another book coming out this year on my best interviews at the Library of Congress. About 15 years ago, I started a program where I interview a great historian about an American history subject in front of members of Congress. Members of Congress only. And I pay for it, I host it, and I... We have a dinner. Members of Congress come. They sit with people from the opposite party. No press is there to see them fraternizing with somebody from the opposite party. And then we have a great person, Doris Kearns Goodwin, or somebody like that. I'll interview them. And members of Congress are fascinated by American history, as they should be. And then they ask questions after the interview's done. And I've now taken the best of those interviews and put them in a book coming out in a couple
Speaker 2weeks. Who do you think the audience learned from most? Given what they needed to learn at that time?
Speaker 1Well, I'll give you one example of a story. I interviewed John Roberts, the Chief Justice of the United States. I wanted members of Congress to learn more about the court. And he did a really good job explaining the court and so forth. And at one point I said, "Mr. Chief Justice, do you always want to be Chief Justice of the United States?" "No." "Well, did you want to be a lawyer?" "No." "Well, what did you want to be when you were growing up?" "I wanted to be an American history professor. That's all I cared about was American history. My father said, 'John, you'll starve to death. There's no money in American history. Get a real profession.'" But John went to Harvard and he majored in American history. And after his junior year, he came back from spring break, got into the airport at Logan in Boston, got into the cab line, got into the cab, and said to the cab driver, "Take me to Cambridge." And the cab driver said, "Are you a student at Harvard?" "Yes, I am." "What are you majoring in?" "I'm majoring in American history." Cab driver said, "Well, when I was a student at Harvard, that's what I majored in also." So John concluded maybe- He didn't want to be a cab driver. He shouldn't be a cab driver.
Speaker 2History is my passion, American history, particularly from like 1880 to like 1940. That's my favorite era.
Speaker 1Well, there are a lot of great books in that era. I just started finally reading The Power Broker. Power Broker is a historic book considered one of the 50 best books of the 20th century.
Speaker 2Yeah. And the American History Museum, or I forget what it's called, up here in the Upper West Side, just did a big exhibit on Robert Caro when he was writing that book. It's the New York Historical. Yeah, sorry. And it was awesome. It was awesome. And so I saw that, and then I also saw you say that it was one of your favorites. So I started reading it last week.
Speaker 1It's a great book. he's now, everybody's waiting for him to finish the fifth volume of his series on Lyndon Johnson, a 35-year project. I don't think I can read five volumes on that. Maybe, but that's a lot. Well, one of the volumes won the Pulitzer Prize. That might be the best one. But, you know, people would really want to see. Remember, the fourth volume ended when John Kennedy was assassinated and Lyndon Johnson sworn in. So the entire Johnson presidency, we're waiting to see what he thinks after all these years of working on that fifth volume. He's now 90 years old.
Speaker 2I also love Titan. That's probably my most favorite business biography. On John D. Rockefeller. Oh, yeah. He was a very fascinating character. He seemed like a mostly a good dad and a good husband and a ruthless businessman. And I like that combination. I think that's super interesting. Carnegie is one of my favorites. I got married at Carnegie Hall because I loved his book so much.
Speaker 1Well, he was famous for, saying you should give away all your money. And there's a book of that era of 1929 by Andrew Ross Sorkin. If you really care about the early 20s, it's a great, great book.
Speaker 2Yeah, I thought that was awesome. Other than, you cite Lincoln all the time, you cite JFK, and I think Washington. When you think back to some of the early presidents or really early leaders or business folks, who do you often refer to when you're like, how would this person handle this situation? Well, look, Lincoln was in a league by himself as president because he saved
Speaker 1the union. He was in a league by himself as president because he saved the union. And he emancipated the slaves. And he did it with grace and humility. He didn't say, guess what, everybody, look how great I am. I just won the Civil War. Or I just wrote the Gettysburg Address by myself. Humble, humility. George Washington set the tone for what a president should be. And he really got us off to a very good start. So those are people that I often cite as really great leaders as presidents. And we obviously had some great in the 20th century as well. Have you read Manhunt about Lincoln's assassination? I did. It's an interesting book in the sense that John Wilkes Booth thought he would be a hero. And interestingly, what happened there is that had Ulysses S. Grant taken the invitation to go to Lincoln that night to see Ford's Theater, he would have had 20 military grades or A's around him. Probably John Wilkes Booth would not have gotten into that presidential box because there would have been a lot of military A's. Lincoln only had one military A and he was drinking at a bar at the time the shot occurred. He wasn't there.
Speaker 2So I've read, there's been four books, four presidents I think have been successfully assassinated. And I've read, I don't know if there's one on McKinley, but there's a bunch on Kennedy. There's a few on Lincoln. And then Garfield has his most famous one, or there's a book, a famous book that- Garfield, the book was written, is a good book this way. Yeah, it's awesome. I didn't know anything about him. He seemed like a really good guy. I didn't realize how great of a person he was. And what's crazy when I'm reading these books is the Secret Service really wasn't a thing until like the 70s. Like they talk about JFK's Secret Service. It was pretty rinky-dink.
Speaker 1Well, I wouldn't use the word rinky-dink, but I would say the mistake that was made on the Kennedy assassination was this. The Secret Service allowed the route to be put in the newspapers. They shouldn't have done that. Secondly, it was raining that day and they had a bubble top on the convertible. The Secret Service asked whether they should take the bubble top off or not because it wasn't clear whether it was going to be raining or not. And President Trump said, President Kennedy's chief of staff said, no, the president wants to be seen, take the bubble top off. Secret Service should not have listened to a political advisor. They should have kept the bubble top on. Had they done that, Kennedy would have lived. And I think one of his whole schticks
Speaker 2was like, look, my father is this big shot rich guy. People think that I'm out of touch. It's important that I'm like a man of the people. Well, remember, that was the first time that
Speaker 1Jackie Kennedy had gone with him on any political trip. First time she'd been west of the Mississippi as first lady. And it was a big deal. And he was like, I'm not going to go with you. I'm not going to deal that she did that. And he wanted to show her off for sure. Yeah. And then I think like a week
Speaker 2prior in Miami there, he didn't have the bubble top either. And they're driving through like downtown Miami. And the Secret Service was like, we've got to be more careful. And he's like, look, guys, I got to be a man of the people. And I think, is this right? Right before or miles before he got shot, he like stopped the car and ran over to like a young family that was holding a sign as he was driving by and thanked them and stuff. It's crazy to think that, I mean, that would never happen
Speaker 1today. When I worked for Carter, there were no metal detectors at the White House. You can walk in with a bazooka. There were no metal detectors. And I remember a couple of times Carter would stand on the roof of the presidential limousine with a microphone and talking to people. I mean, incredibly exposed. Today,
Speaker 2we're much more careful. I appreciate you doing this. I've had a lot of admiration for you
Speaker 1for years. I'm so happy to go to talk to you. I hope I don't disappoint you. So now you met me, you say, hey, this guy wasn't as good as I thought, right? No, not, but you know,
Speaker 2I feel that way about reading a lot of books. Has there anyone who you've read about where you're
Speaker 1not my guy anymore? Well, usually biographers write books about people they like. They don't usually write about people they don't like. The other book on Roy Cohn is not one somebody that the author liked. You know, most of the times you find somebody to admire. Doris Kearns Goodwin always says she falls in love with the people. Yeah. And because she had to spend 10 years with them. And, you know, you don't want to spend 10 years with somebody you hate. So generally people write books about people they tend to admire, generally. And we have so many books about the same people. We have 10,000 books on Lincoln, 10,000 books on Kennedy. Why do we have so many books on the same people? Because people buy these books. People like them. And so people and authors
Speaker 2write more about them. Well, and you've done like the ultimate thing when it comes to writing a book where you just, it's interviews. I don't have what it takes to write a book, but if I did, that's the style. It seems awesome. I love your style of books. I love that style. Well, thanks very much. Yeah. Thanks for doing this, man. You're the man. My pleasure. Appreciate you.
Speaker 3All right. Let's take a quick break. I want to tell you about Marketing School. It is a podcast
Speaker 4that is part of the HubSpot Podcast Network, and it is run by Neil Patel and Eric Hsu. And these guys are both marketers who are running businesses. And so if you want real world tactics from practitioners who are actually out there in the field doing it, this is the podcast for you. Check it out wherever you get your podcasts.
PodcastTranscript AI