My First Million - David Rubenstein: We took $5M and turned it into $500B

Episode Date: September 14, 2026

Sam's database on how long it takes to become a millionaire: https://clickhubspot.com/pnlv Episode 861: Sam Parr ( https://x.com/theSamParr ) sits down with David Rubenstein ( https://x.com/DM_Rubenstein ) to talk about turning Carlyle into $500B, his $14B miss, and the greatest business lessons in history.  — Show Notes: (0:00) Turning $5M into $500B (5:13) Scrappy private equity (11:58) Don’t fool yourself (14:14) Turning down 20% of Amazon (16:23) Recruiting big shots (20:40) Finding the right partner (22:02) Trade-offs (27:39) Witnessing ascents to power (31:40) The Greatest Sentence Ever Written (33:37) History that repeats itself (35:49) Recommended Reading — Links: • Carlyl - https://www.carlyle.com/  • David’s books - https://www.davidrubenstein.com/books/  — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com  • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Shaan uses Mercury across all of his companies. you can too: http://mercury.com/  Mercury is a fintech company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /

I 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. But 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. No, because if you're an entrepreneur, you always think something bad's going to happen. You still feel that way? Every day, 99.9% of the companies who start 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 a company was going somewhere, I said, we should have taken that deal. That was stupid. That stock's probably worth $14 billion now.

Can I ask you about seeing people get power? Well. I feel like I can rule the world. I know I could be what I want to. I was looking at this photo. There'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 and it wasn't experienced. But in our system, if you work in a campaign, 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 of the White House, you know, they couldn't believe it. Then I took him in to meet the president, which is what that picture shows, and they were, you know, in awe because they were, what do we 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 a runny office, even if it was a yellow dog. So 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 the most powerful things on earth. What do you do your first month?

Do you remember? Carter had a lot of promises, and 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 promise is better than anybody, and so I would be able to object and say, Mr. President, it's a good idea that this person has, but it's a violation of a campaign promise.

Every administration, the current administration, every administration, as young people who were in their 20s, or 30s who work in the campaign, and they're energetic and eager, and they get jobs, and some one will turn out to be great, and someone will turn out to be not as great. But how did you figure out how to make good decisions, because you are so young. I mean, I didn't have a lot of policy experience. I'd worked on Capitol Hill for about a year, 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 would be, and then we'd have issues, and we'd come up with

remember the president has policy positions that he wants to take because of campaign promises. So we would articulate, you know, how we could fulfill his promises. So you were there for four years. What did you feel like when it was done? Well, when you work in the White House, people come to you and tell you and tell 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. And we win, I'll be maybe the senior investigative eyes 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 don't want to tell my mother, look, your son is unimpleased. Nobody wants a Carter White House aide. Not unlike the experience that 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 couple of years later. I think the best way to become successful is to see how other people did it, whether you're going to copy them, 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 over 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 clicked a 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? I 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 the Mark Zuckerberg's and Bill Gates of the world that are different, but an average person will start at the 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. Did you think, like, a lot of times when people start businesses, they're like, how much runway do I have? When I started, Carla, I was married. When I left in White House, I was a I got married a couple years before I started Carlisle. So you had the pressure of like, I need to provide? Well, you have some pressure, but, you know, it'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. Yeah. 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 six. 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. Well, remember, 99.9% of the

companies that are started 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 smaller percentage are there 10 years later. So most companies that are started just don't work out. What did you do the first handful of weeks after you decided to start the company? Well, 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, Carlisle manages not $5 million, but $500 billion. So it's grown to be one of the larger private equity firms to the world, 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 Conway. And we hired another person, a senior officer from Marriott. So we had a number of people at the beginning, four of us at the beginning, and then we grew it. The companies we, Carlisle controls, have been a million and a half employees.

And the Carlisle itself got about 2,300 core. It sounds like the, like, whenever I started my last company, the people, or in this company, the people who I initially hire, they're basically, like, rejects. Like, it's like, it's like smart, ambitious, rebellious. But it sounds like the people you hired early on were very pedigreeed. Well, 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 realized the job that they currently have may not be so great, so they take a chance, and some people work out, and some people doesn't work out. I know 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.

I 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, you know, 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. What we did that was different was we had multiple funds. In private equity, historically, you had a buy-out fund if you're a buy-out

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 buy-out fund, a growth fund, a real estate fund, a debt fund, and I had multiple funds, and then I had the idea of globalizing and I have a fund in Europe, in 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 I 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, 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 they'd 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. The second fund was a billion. And so we got bigger. How did you pay your team then if you don't have a fund, if you're doing deal by deal? Well, 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 funny. But that's true. Everybody, anybody that's built a successful company is always going to have a hard time at the beginning. And, you know, 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, you know, 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? It was about $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, like, the scrappy stories of what your first office looked like? When I started the firm, we didn't have any money. We had no credibility. So there was a new office bill 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 the movie called Broadcast News with Jack Nicholson in that space. So the space was now available. I said I would take the space was 5,000 square feet. And the leasing agent said, look, you can have another 5,000.

If you want, you 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 attempted 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 practice of law. And I was afraid if I took a bigger space and we would try to expand through rapidly. So that's probably why we didn't do it.

Later, we had to expand. And now we're the biggest tent in the building. About one night a week, I'll be laying in bed with my wife, you know, doing Pilate Talk. And I'm like, you know, one day, if we nail this, this and the next 10 years, maybe we can be this. Or maybe in 50 years, we can be this. and like you have these like, you know, vision sessions, were you doing that with your spouse?

Every day was a challenge because we're trying to start a firm. Remember, in 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, D.C. Washington, D.C. was not New York. People didn't take you seriously. And people asked me, why did you do it in Washington? Well, Senator Everett Dirkson, 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 companies 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.

You're the second person in the past couple weeks. So over here, we've had Ray Dalio recently. And I asked him the same question. I was like, when you were first getting Bridgewater going, did you, like, what were some crazy ambitions? Did you say, like, oh, it would be awesome if we made $100 million or a billion dollars or had 10,000 employees or whatever? and he was like, I just wanted to make $100 grand a year so I could like pay for my family. That was my goal. When 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 like I can't believe that there was no like aspirations early on just for the sake of motivation. You know, if you have the grandiose expectations or plans at the beginning, you might be, you know, 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 that 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 that expanded to Yale or Princeton. That was it. The idea of doing non-students really hadn't, wasn't even surfaced then. I don't think Mark Zuckerberg actually thought he would ever build what he built. Yeah, 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. Look, I saw Jeff at the beginning because he had to get a bibliography of books and print to

go to sell books of the internet. One of our companies had a bibliography, books and 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 I said, we don't want a piece of an ill-liquid company, a startup. That's not more. We want cash. Ultimately, we agreed, I think, $100,000 a year for five years. We rented in the bibliography. Wait, you owned a company that was a book publisher, and it had a book that had a list of every book, every written. And the offer was 25 percent? It's 20 to 25 percent. Later, after a company was going somewhere, I said, we should have taken that deal. I flew out, and I met Jeff Bezos for the first time. He had one office. He was doing the books himself, and he would

take him 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. He got some stock. Then we sold it at the IPO. That was stupid. That stock's probably worth $14 billion now. Did he have any attributes back then that you saw this guy is going to be the guy? He'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 companies are not shrinking violets. You know, 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. And you 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. Well, what happened was when we were, starting the company or right after we started it, they started 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 join 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 were in 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 a lot of corporate boards or maybe 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 a Secretary of State. While this is the ultimate great man of the world, Secretary of State, Secretary of Treasury, White House Chief of Staff, and I was able to recruit him. How many other options did they have?

Why would they trust, like, a startup? I mean, they always had all the 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's also a partner in our firm. And then after Baker, we had Dick Darmine, who had been one of his protegees, who had been the head of L&B. And then later George Herbert Walker Bush, former president of the United States, became 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.

Do you remember what the pitch looks like or sounds like when you're swinging above your weight? Oh, it's saying, look, we're a firm in Washington. We understand 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, you have to build your track record. So if you did one deal and it exited well, then you can go and go and go and, and use that, they say we're going to do another deal similarly. So it worked out. But we made some

mistakes and everybody makes mistakes, but it worked out. Yeah, 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? One time, we had a limited amount of cash. And then we were trying to buy a company, and it was in bankruptcy court. We were trying to buy our 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 said, hey, what are we going to do to meet the payroll? But in the end, we actually got the company,

and in the end, it turned out to be a very successful deal. But, you know, I remember waking up in the middle of the night, thinking, hey, I'm not going to pay the rent? What year or how many years into the company did you feel like you personally were like, all right, I'm financially stable? Maybe yesterday. It takes a while.

I mean, when we were building the company, we ultimately sold a piece of it to CalPERS, I think about 5% of California retirement system, and they'd value the company at something being worth like $2 billion. The company was worth $2 billion or $2.5 billion. Nobody thought that a private equity firm in those days had franchise value and could be sold, but we sold 5% to CalPERS. That was probably 2009 or something like that.

And then a few years later, we sold 7.5% to Mubata, which was an Abu Dhabi investment arm, and that value the company had been worth $20 billion. And then we later took the company public. But 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. No, 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. But 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 common steady, and it's like the greatest pair ever because he's the only one who I will be neurotic with. Well, I have two people that I really built the company, and one of them is now 80 years old and has all dark hair that have one gray hair. So he made me 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-confidence about his abilities to be an investor. But look, you're always worried something bad's going to happen. I'm worried every day. Now the principal owner of the Baltimore's, I'm worried every day that's something bad

going to happen. What are you worried about with the Orioles? I want to make the playoffs. And, you know, we're now one game out of the playoff. But one 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. I get worried about looking stupid on the internet, and like the comments, I act like they don't bother me. They do. Do you get bothered by comments or people criticizing an interview? Advisors 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. I 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?

Well, 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 driven and have businesses that require 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. Do 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? No.

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. will 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 dropped 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.

Hey, let's take a quick break. You know that feeling when strategy is done, the brief is written, 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 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. One 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. Well, 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 in my home this weekend were great athletes. Now they often have artificial hips or artificial knees because they were such great. They hurt themselves. So I don't really have those that problem, though. But when you think of, do you ever think of like who do you admire most, not just for their business ability, but for the holistic, like, this person under these circumstances has mostly nailed aspects of life that I admire? Well, there are a lot of people. I'm a person who was in my

firm, I thought his professional and career was extraordinary, and that was Jim Baker. Great job in the federal government and 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 that's out there. It's perfect. I talked to someone who worked with you at Carlisle. He was an associate, but he was saying something. He's like, 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. Well, I always view myself as being from a blue-collar family in Baltimore. And I always, you know, realized 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 share 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 fancier person, I guess. When we had Lloyd in, he was like, he told the story about how I think his father was a post office. His 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 his father was 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. And 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? You 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, 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 suits there for 10 years. That's a trick. How many do you have? Because that's the only thing I've ever seen to wear. We 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. I'm amortizing them. I'm still wearing the same ties and suits I've had for many years. Well, it looks good.

I mean, that photo, when you're 27, you look sharp there, too. By the way, they dressed the presidents and a 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. And 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 is fair to say. But can I ask you about seeing people get power? Because I've read, I think, is it the governor of Virginia? Was I an intern with you guys? Glenn Yonkin worked at Carl off for 25 years. And he got elected governor, Glenn Yonkin, yes. And 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? Power does change some people. And Glenn Yonkin, I hired him pretty much Adam McKinsey right at a 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 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 it's 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? Yeah, 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, it 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, 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. Well, 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 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, have been different. Can I ask you about owning all these awesome documents? Yeah, sure.

How much have you spent in some? I've never added it up. I don't really honestly know, but what happened was I stumbled into buying the magnet card. I didn't really intend to, but somebody told me it was about to be sold, and it was the only copy of 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 started getting other historic documents, the Emancipation Proclamation, Declaration 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 into 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.

When you're bidding on them, are there other bidders typically? Well, there typically are, sure. When I bought the Magna Carta, I was bidding, but I was in a room. They put me a little room at a telemarketer. phone 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 my documents for a lot less. And they now gravitated to that. So it's more competition. And look, the decoration and penance because of the semi-quinstantial become a document of greater interest to people. So the prices have gone up dramatically to buy these historic copies. Well, 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. And the idea of like we hold these shoes to be self-evident, that's kind of interesting and that it's a very 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 cherish it?

Well, they didn't treat the document that well. When the Declaration of Independence, after it was drafted and signed, they basically folded it. They hit it, place it, they put it in sunlight. No, I don't think they thought that at all. But not until 1823, when John Quincy Adams was Secretary of State, he realized that the document was fading so much. they better get some copies as sooner nobody would be able to see it, and they made copies then.

Yeah, 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. Remember, 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 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, there 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, and he kind of thought 20 years 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. Yeah, look, the founding fathers, if they were to come back today, they'd be astounded that the country, that was a tiny country, in the Eastern Seaboard, it's been for these since World War II,

the most powerful country in the world in every category you can mention. They would never dream that. Today'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.

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And A, members, FDIC. One 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, you like said it like to someone. He's like, I think the world might end. Like in like it was just like funny that there was like different periods of time where people always think like the worst is going to habit and we end up working out. Are there any like sets of rules or axioms or trends that you have seen repeat themselves over? over and over again that have helped you deal with whatever you're dealing with at the current time?

Well, 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 nonexistent. And so what we're really going to have to do is, is in effect, pay it off in devalue dollars, and the dollar will go down on 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 grow 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 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. Secondly, I actually generally interviewing people about books I am interested in reading. and this kind of forces me to do it. Third, it's my anti-Alzheimer's device because they tell you when you reach 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 I do is I read a lot and I interview people.

And when you interview people, you got to keep your brain sharp, as you can see. You got to go back and forth, listen to the person saying. Think of the next question while you're listening to a 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. What are some of the favorite things that you've read in the last six or eight or 12 weeks? I've read a book on Roy Cohn.

It's called American Scoundrel, which was a really good book by Kai Bird, the previous word of book on Robert Oppenheimer that won the Pulitzer Prize. and it's just amazing what Boycone was and so forth. I recently read Beverly Gage's book on Jayhager 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 only. and I pay for it, I host it, and 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, Kerns, Goeburn, 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 is done, and I've now taken the best of those interviews and put them in a book coming out in a couple weeks. Who do you think the audience learned from most, given what they needed to learn at that time? Well, 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. But 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, and that's all I cared about is American history. My father said, John, you'll starve it. That there's no money in American history. Get a real profession. But John went to Harvard in a major 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 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 drivers said, well, when I was a student at Harvard, that's what I majored in also.

So John concluded maybe you didn't want to be a cab driver. He shouldn't be a cab driver. Well, I'm like, history is my passion. American history, particularly from like 1880 to like 1940, that's my favorite era. While there are a lot of great books in that era. I just started reading, finally reading the Power Broker. Power Broker is a historic book considered one of the 50 best books of the 20th century. Yeah, and the American History Museum, or I figure what's called, up here on the Upper West Side,

just did a big exhibit on Robert Caro when he was writing that book. And that's the New York, it's the New York historical. Yeah, sorry. And 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. It's a great book. But 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's sworn in. So the entire Johnson presidency,

we're waiting to see what he thinks after all these years are working on that fifth volume. He's now 90 years old. I 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 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. Well, 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. Yeah, 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 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 to get his work addressed by myself. He's 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 grade in the 20th century as well. Have you read Manhattan about Lincoln's assassination? I did. That is 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 with a Ford's Theater, he would have had 20 military grades around him. probably John Wilkes Booth would not have gotten into that presidential box

because there were been a lot of military aids. Lincoln only had one military aid, and he was drinking at a bar at the time the shot occurred. He wasn't there. One of my, so 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. There's a book, a famous book that. Garfield, the book was written, is a,

It was 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 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.

Well, 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 it was going to be raining or not. And 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, Kenny would have lived. And I think one of his whole schicks was like, look, my father is this big shot rich guy. People think that I'm out of touch. It's important that I, like, I'm like a man of the people. Well, he remember, he, that was the first time that Jackie 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 that she did that. And he wanted to show her off for sure.

Yeah. And then I think like a week prior in Miami, there, he didn't have the bubble top either. And they're driving through like downtown Miami. And the street route surfers 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 him and stuff.

It's crazy to think. I mean, that would never happen today. When I worked for Carter, there were no metal detectors of the White House. You can walk in with a bazooka. There were no metal detectors. And I remember a couple times Carter would stand on the roof of the presidential limousine with a microphone and talking to people. I mean, incredibly exposed. today we're much more careful.

I appreciate you doing this. I've had a lot of admiration for you for years. I'm so happy to go to talk to you. I hope I don't disappoint you. So now you've met me, you say, hey, this guy wasn't as good as I thought, right? No, not, but, you know, I feel that way about reading a lot of books.

Has there anyone who you've read about where you're like, not my guy anymore? Well, usually biographers write books about people they like. They don't usually write about people they don't like. The book on Roy Cohn is not the one somebody that the author like. You know, most of the times you find something to admire. Doris Kern's Goodwin always says she falls in love with the people. Yeah.

And because she has to spend 10 years with them. And, you know, you don't want to spend 10 years with somebody who 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 authors write 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 agree. So 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. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back. All right, let's take a quick break. I want to tell you about marketing school. It is a podcast that is part of the HubSpot Podcast.

network and it is run by Neil Patel and Eric Sue 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 podcast.