Michael Ovitz - Turning Potential into Prominence - [Invest Like the Best, EP.418]

My guest today is Michael Ovitz. Michael is the legendary talent agent and co-founder of CAA, or Creative Artists Agency, and he is joining me on Invest Like The Best for the second time. Michael started CAA in nineteen seventy-five and over the next twenty years built it into the world's most formidable talent agency, changing Hollywood forever. He shares his insights into how he identifies exceptional people across diverse fields, from Hollywood directors like Steven Spielberg to tech founders like Alex Karp of Palantir and venture capitalists like Marc Andreessen. Michael is a force whose expertise extends beyond just people. He's also become a master in creating institutional momentum, which you'll hear in his involvement with MoMA, Gulfstream, and more. We discuss his pilot's checklist for evaluating talent, the importance of time as his most valuable resource, and why he believes maintaining excellence is critical in any field. I'm also excited to watch Ovitz as he helps build the asset management firm Treyville with multiple-time guest Ali Hamed. Please enjoy my great conversation with Michael Ovitz.

So Michael, last time we did this, we covered so many interesting parts of your life, career, and story, but we left a lot out, even in 2 hours. I thought a common theme for today that would make it really fun is this joint notion of you spotting talent extremely early, what the talent you selected had that the hundreds of others you met with didn't, and then helping and watching those people build enduring institutions very quickly.

I'm especially interested in the first 10 years of institution-building around some of these people you've been intimately involved with. Maybe start with that talent piece. What is it that all these different people, who are very different from each other, shared in common when you first saw them, especially the ones who were very young when you saw them? Some of them were in business school and hadn't proven themselves.

Certainly the ones from my world, business and investing, are one batch. Whether it's Alex and Joe at Palantir, Steve Schwarzman at Blackstone, Josh at Thrive, or Mark and Ben at Andreessen Horowitz, the list goes on and on. There are also people in other fields that I'm not familiar with, and companies you were involved in. Take MoMA as an example. Everyone knows MoMA as this preeminent art institution, but it wasn't always MoMA. MoMA wasn't always MoMA.

There are plenty of museums. I'm very interested in the people component of how MoMA became MoMA—what you saw, what you did, who you recruited, and how. These are all examples of the same question over and over again with each of these people, but for context, those are just some of the names.

Let's take MoMA, because it's right here in town, down the street, and it's a phenomenal institution. It's a place I've been on the board of for 35 years. I go there sometimes just to unwind, believe it or not.

There were 2 places I went to in the last 40 years in New York City to unwind. One was MoMA. When I had an hour between meetings, or even a half hour, I'd fly in there, sit in one of the galleries, and take in the extraordinary stimulus of creativity. I'd say to myself, "What were these people thinking? When did they do this? What influenced them? How did they come up with this idea? Why is it different, better than anything else in its genre?"

When you look at MoMA, they have the best of the best, which, as an art collector, is almost impossible to do. The second place I went was to see a very close friend in New York, whom I saw and talked to 3 or 4 times a week, named Roy Lichtenstein. I used to go to his studio, which was also where he lived, in the Village. I'd walk in, his wife Dorothy would take my cell phone, and Roy would let me sit there and watch him paint. We'd talk, and I wasn't allowed to do business. It gave me a great sense of grounding, frankly.

At MoMA, I was very lucky to be asked by David Rockefeller at a very young age to get involved in the museum. If you ask me why David did this, my guess is that he wanted someone from the West Coast, someone involved in the media business, and someone who would bring the mean age of the trustees down a bit and have a culturally contemporary point of view that wasn't necessarily just fine art.

I was in a rather unique position in that I not only represented most of the major working directors in the business—filmmakers who made art, but a different kind—but I was also an avid, rabid art collector.

Mm.

It was a 2fer, I think, for David. It was the best thing I ever did, and I was fortunate enough to be asked to be on the search committee for the new director. This was over 30 years ago.

MoMA was always amazing, going back to the days of Blanchette Rockefeller and all the wonderful women in New York who put the early collection together. As a matter of fact, there's a phenomenal book out right now that tells not just the history of MoMA, but explains how European art was rejected in the United States.

Mm.

It never made it here until the '40s. Remember, in 1906, '07, '08, '09, and '10, some of the greatest work being done by Picasso, Braque, and Klee was created in that timeframe, and it was completely rejected by the United States.

Crazy.

MoMA started collecting it, oddly. So MoMA has always been on the cutting edge.

At the time when we were doing the search, we needed someone who could make a dynamic turn in the museum. The one thing about an art museum is that, at the end of the day, it's entertainment for different strata of social culture. It's not just the elite who look at art or can afford art. There are many people who aren't in that financial category who love art. They can buy posters, they can buy prints. There are a lot of ways to skin that cat.

MoMA was basically a commercial showplace for tourists to come and look. I remember I had a meeting years ago with the mayor of Rio de Janeiro. A friend of mine asked me to meet with him, and the purpose of the meeting—this was 30 years ago—was to discuss how they could make Rio a great city.

What a question.

Yes, and that was what the lunch was about. I hosted him at my house. He brought about 5 associates with him. I said, "Look, the thing that defines great cities at the end of the day is the cultural aspects and the sporting aspects—the places where people gather."

You could have a great city that's beautiful, with amazing architecture, but there's no cultural ethos in it. If you look at the best cities in the world, from New York to London to Paris, they are loaded with cultural initiatives, and people can get lost in them. I don't go to Paris or London without making time to see half a dozen museums, even if it's just for a short touch-and-go.

My answer to him was, "Build an art collection and promote a couple of your sports teams. You have amazing sports stars." I think the museum is critical. In New York, MoMA needed to move to the next level.

So we needed a director, and it was a tough assignment because the director has to be intellectually sufficient, a leader, and a thought provider, as well as someone who has the ability to see around corners. It's very tough to do that. The director also needs a sense of what the constituency wants to see, and that constituency is not just native New Yorkers but visitors.

Yeah.

The number of tourists we get is staggering. We take 20,000 people a day through the museum, 7 days a week.

You need a founder in that role.

Exactly right. You need someone with a founder's mentality. We were lucky enough to stumble on a man named Glenn Lowry, who had absolutely no contemporary art background. He had a PhD in Islamic art and knew nothing about contemporary art, but he was smart, articulate, well-spoken, handled people brilliantly, and had this extraordinary burning desire to learn.

Everyone who was debating it was saying, “Well, he doesn’t know anything about art.” Well, that’s true, but neither did I when I started, and you learn. We chose Glenn. It was an extraordinary long shot, but compared with all the other candidates, who all had mega-museum backgrounds, it turned out to be the greatest thing we ever did.

Glenn came in and didn’t do anything at the beginning except study. There were a lot of employees there. There was a lot of art there. We have 35,000 pieces of art just in storage.

Hmm. Crazy.

We have the greatest reservoir of modern art in the world. We needed someone who knew how to display it, could raise money, understood who the new artists were, and didn’t lean on some of the older postulates of the museum, which was only to take established artists into the collection. How do we start a fund for the 21st century, taking young, new artists? Glenn turned out to be that guy.

If I think about the competitive landscape, this guy did a fantastic job for 30-plus years.

Mm-hmm.

He updated and remade the institution and had that founder energy. Surely other amazing museums were competing for some of the same things that MoMA won, and MoMA won—whether that’s the works specifically, the brand, the cultural resonance, the building, or all these different things. What were the things that you saw him do, or helped the institution do yourself, to win over time in a competitive landscape?

He did so many things that were fantastic. First of all, he led by example. There was nothing he asked anyone to do that he wouldn’t do himself.

Yeah.

That’s the cardinal rule of being a leader: first person out of the foxhole.

Hmm.

You want someone to do that, you better be able to do it yourself. And if they don’t do it, just go do it.

Secondly, he populated the board with the most diverse, amazing group of men and women, but they had one common denominator: they were all art collectors of something.

Yeah.

They collected something, so they had a passion for the arts. There’s a huge difference between an institution with trustees that are financially responsible or socially responsible but don’t have the passion to collect something, and an understanding of the mission of the museum from a collecting standpoint, balanced by a financial standpoint, and also how to show it off. The shows are the best.

Mm-hmm.

The trustees are incredibly supportive. You don’t have to ask anybody for anything. It’s like a club, and everyone gets along, which is really crazy, and supports each other. So it just all works like a Swiss watch.

In the time that you would be in the studio with Roy, what was that like? What was his affect? What was his style? What did you learn from him?

I love that guy. He is the opposite of me. He is at the same speed 99% of his life.

Patrick O’Shaughnessy

Hmm.

He doesn’t let anything bother him. He knows what he’s doing. He enjoys his work. There’s a Zen-like quality around him, and when people say that, you kind of go, “Oh, nonsense.” But, man, he had it.

He had this aura about him of calmness and determination. He was passionate about what he did, excited about his art, but had no emotional swings. He just lived his life and enjoyed his life.

We brought him to L.A. for six weeks to paint a 28-by-26-foot-high mural in the lobby of our building that I. M. Pei designed. It was the greatest six weeks of my life. I sat there and watched—I talked about this on the last podcast—this guy create something off a white canvas out of his head. To me, that’s the ultimate definition of being creative.

Patrick O’Shaughnessy

If you think about the ability to build your reference class in art, or in founders, or in anything, how have you done that most successfully? It intrigued me last time we were together. You said you were going to Brooklyn a lot just to do studio visits here in New York City, and that you’re constantly making time to meet mostly young women artists in Brooklyn lately, of a specific school or style.

Abstraction.

Patrick O’Shaughnessy

Abstraction. It just strikes me that this is something you’ve done over and over again: whoever you’re picking, it’s not that you just met someone and liked them. They’re one of hundreds or thousands of people that you’ve met. Talk about that benchmarking exercise.

That benchmarking exercise applies not just to artists, but to everything in my life.

Patrick O’Shaughnessy

Yeah, right.

All the people you mentioned, I identified early as people I wanted to be involved with. When I met Alex Karp 20 years ago, whom Peter Thiel introduced me to, he wasn’t the Alex Karp he is today, who is highly profiled, incredibly well-spoken, and dogmatically passionate about his point of view. He wasn’t that guy. He was just a brilliant guy who had a Ph.D. in philosophy from Germany and, frankly, looked ill-equipped to run Palantir.

When Peter asked me to meet with him and I looked at his credits, I called Peter and said, “Give me a little color here.” They both spoke German. Peter’s from Germany, so they had a common denominator. But Alex sure didn’t look like the guy who was going to lead this highly technical, cutting-edge company 20 years ahead of the AI infatuation.

But sitting with the guy was the same thing as sitting with a young artist. I’m guessing 30 years ago—I’m not even sure—Larry Gagosian, who, as you know, was my assistant at the William Morris Agency 50 years ago and whom I’m crazy about, calls me up and says, “You’ve got to go see this young artist that I’m looking at.” And I said, “Sure.”

So I go to see this young artist. Her name’s Cecily Brown, and I look at the work. I was mesmerized by the work. She hadn’t had a show yet. I called Larry and said, “She’s amazing.” He said, “Yeah. She’s really good. I just had lunch with her last week. She’s about as important an artist as there is right now working.” I just saw something I liked, and it was the same with Karp.

When I met Alex, we met at the Allen & Company conference, and we spent, I think, three and a half hours talking about everything. Not about his business—just about life, about tech, where it’s going, what’s happening politically, trends of the past, and things that point to the future. And, man, I really liked this guy. I said, “We can build a business around this guy.” He had something very special, and you could tell that he could be a leader. Glenn had that, too.

All these people that I’ve been fortunate enough to come in contact with have very similar traits. They’re interesting, they’re aggressive to certain degrees in their own way—some blatantly, some not so. They’re wicked intelligent, they’re perceptive, and they all have this extraordinary burning desire to learn. They want to learn something every minute of the day, and they don’t want to waste time. Time is a valuable commodity.

So that’s pretty much my philosophy. When I started as an agent, I was 21 years old, and I knew right off the bat that time was my enemy, even at that age. Because if I went and met with someone to judge whether I could do something for them and made a mistake, that mistake was irreparable and a time sink that can’t be recovered. And it’s not a hiatus; it’s a loss. There’s a big difference. It’s a loss. You could be doing something else with that time.

So I started to make a set of parameters when I met people about why I wanted to continue the dialogue. I have a pilot’s checklist in my head of things that are important to me, and it doesn’t really matter what the vocation of the person is.

It doesn’t matter whether it’s Ted Forstmann, when he called me to help him with Gulfstream, which was a dying company—they were going under—and I thought it was an amazing turnaround opportunity and went on the board. We made a decision to recruit. Ted—I was on 5 of Ted’s 13 boards and spent a ton of time with him—was a very close friend until he passed away.

He said, “What can I do to make Gulfstream different?” Bombardier was killing them at the time because they had a bigger cabin. And I said, “Teddy, there’s only one thing you can do. You need to recruit a board that becomes the greatest set of super-salesmen in history, because you don’t need our advice, you don’t need our financial engineering, and you don’t need us to read balance sheets. You need us to sell airplanes.”

What he did is he went out and put a list together. He brought it back to me, and we went through it. On the list was the who’s who of certain areas. On the list was Roger Penske. On the list were Don Rumsfeld, Colin Powell, and Henry Kissinger. There was a guy who was the CFO of GE when they were the most important company in New York City, when Jack Welch was there. Dale Frye was his name.

He had Charlotte DeBeers, who was the most important female advertising executive in New York City. And he had Bill Acquavella, the great art dealer. All of us had assignments, and we all covered areas. Bill covered art, Kissinger covered politics, and Colin Powell covered the U.S. Army and the DOD. Everybody had an assignment.

We met monthly, not quarterly, and the attendance at the meetings was 100% every time. We had so much fun at the board meetings and board dinners that after we sold the company 7 years later, we all continued the board meetings.

Patrick O’Shaughnessy

How did you convince those people, many of them at the peak of their powers, I’m sure, to take their time and do this? What was the pitch? What was the incentive structure? Why did all those people agree to do that?

Well, we divided up the list and called people we had relationships with.

So I called Colin Powell.

Patrick O’Shaughnessy

Those relationships—they did it for you.

Well, everything’s relationships—

Patrick O’Shaughnessy

Yeah.

At the end of the day, or the beginning of them.

Patrick O’Shaughnessy

Right.

The whole idea is to make them and then keep them. If you’ve made a mistake, that’s why you don’t want to make a mistake.

Patrick O’Shaughnessy

Mm.

So I called Colin Powell, who I knew, and I said, “Before you say no, do you want to have some laughs, and do you want to make a little money?” The answer was yes to both.

Patrick O’Shaughnessy

Yeah.

Then, when I told him what we were doing, he said, “What a hoot.” He said, “Okay.” I called Henry because I was friends with Henry Kissinger—he was on the board of MGM. I said the same thing to him, and he thought it was hysterical. He said, “What…” I can’t do his accent, but it was hysterical. He said to me, “What do I know about airplanes?” in this thick, heavy accent. I said, “You fly in them, don’t you?” And he said, “Yeah.” I said, “Great. You’ll find someone to sell them to.”

Patrick O’Shaughnessy

At the board meetings.

At the board meetings. So that was the first thing we did. Teddy would approve the minutes, 100% attendance. Board meetings were always at 5:00, and then we all went to dinner. Colin would stand up and say, “Well, I’ve sold 3 G4s to the U.S. Air Force.” Kissinger would say, “I’ve sold 5 G4s to this royal family.” It was crazy.

Patrick O’Shaughnessy

What fun.

I got up and said, “I sold a G4 to 2 actors,” and I’d give their names. Everybody did that. The sales went crazy for the company. At the end of the day, you have 2 issues with a company like that: a great product, which they had, and sales. There is nothing else. They had a great product, and we provided the sales. He took the company from bankruptcy to a huge sale to General Dynamics.

Patrick O’Shaughnessy

If you think back to your checklist—your pilot’s checklist, an appropriate follow-up to a Gulfstream discussion—what’s on that list? Especially when you’re meeting someone for the first time, and especially when it’s Alex Karp early on, when there’s not a lot of information about him. What is that list that you’re running through in your head?

Well, first of all, you have to see if there’s a visceral connection.

Patrick O’Shaughnessy

Yeah.

That’s not anything that’s on the list. Do you feel some kind of rapport with the person? That’s a given and critical, okay? The list is amorphous.

A longtime client and a good friend, Martin Scorsese, is a genius—an absolute genius—at how he looks at life, the prism he looks at it through, and then how he regurgitates it back into a visual image. His frames, if you pull them out of his movies, could stand on their own as artwork. It’s insane, his frames.

He said—I said, “When you’re looking at actors, what are you looking at?” He said, “Their eyes.” It spoke volumes to me. I also have a frame of reference because I’ve met so many people. I collect art and people. I love people, and I love having relationships. The more you meet, the more benchmarks you have.

When people ask me, “How do I learn how to collect art? Do I read all these books?” I say, “Don’t read anything.” I told you this on the last podcast: just—

Patrick O’Shaughnessy

Go meet a million artists.

Just—

Patrick O’Shaughnessy

See a million pieces of art.

Look at pictures.

Patrick O’Shaughnessy

Yeah.

Just look at pictures. When you asked me about going to museums in Brooklyn, we’re going out Saturday, tomorrow night, to look at a young artist. She’s not in Brooklyn; she’s in New Jersey, but same difference. We’re going to her studio to look around. I went out to Red Hook a couple of weeks ago to look at an artist named Nicholas Party—brilliant young guy, brilliant—and got to go into his cave to see what he does and how he does it. I’m fascinated by process because I can’t do it, so I’m fascinated by the bar I can’t get over. It’s probably why I was an artist representative for years. Watching Nicholas Party create in his environment is a treat beyond belief, right?

Patrick O’Shaughnessy

What kinds of questions do you ask him? When you’re digging into someone’s process, what have you learned is the best way in?

Well, it isn’t questions. It’s observation, and it just bubbles out. He uses pastel, and I was fascinated by that because it comes off the paper. He went over to one of his artworks and banged it on the floor, and dust started coming off.

I said to him, “Nicolas, that could be like an invisible painting in some ways.”

“No, it sticks.”

It fascinated me that he would do that because everything about artists was built for the ages. We’re looking at art from the 18th, 17th, and 16th centuries, right? It’s 600 years old. It’s 500 years old.

Patrick O’Shaughnessy

Can you tell me about Larry Gagosian?

Larry was my assistant at the William Morris Agency in 1970, and he was really good. He had a way with people. He was smart, temperamentally aggressive, and he showed all the promise in the world. We worked together for about a year.

He came in to see me and said, “I hate this place.”

I said, “There’s nothing to hate or love. This is a tool for you to learn. That’s all it is. We’re in graduate school, basically.”

That’s how I looked at it. I was getting a master’s in entertainment there when I was 21. He couldn’t stand the people. He couldn’t stand the backbiting. He couldn’t stand the deceit—all the hallmarks of the entertainment business. He couldn’t stand people not telling the truth. He didn’t like the environment.

I spent a month trying to talk him out of quitting, and he finally quit. He opened up a little poster shop in Westwood, selling $20 posters of fine art. The rest is history. He’s a brilliant dealer. He’s a very loyal guy. He’s tough as nails—tough—and he’s a great negotiator. He has an amazing eye.

His townhouse up on the Upper East Side is the epitome of good taste. If you’re into period furniture from the Art Deco period and great art, it’s all mixed. There’s no period that stands out. He’s mixed Richard Prince and Picasso. Go figure.

Patrick O’Shaughnessy

If you think now about post-talent-spotting—so you meet an Alex Karp and you want to work with him—talk about what you’ve learned helping and watching institutions that end up as big as Palantir has. You’ve been a part of lots of them in those first couple of critical years. What are the common ingredients that you saw for really fast growth and success?

Well, he did something that I did at CAA, which I thought was really smart to do. He didn’t get the idea from me.

Patrick O’Shaughnessy

Yeah.

One of his partners, Stefan Kohn, a brilliant young engineer, would take 1 meeting every 10 minutes with an engineer. I had an office next to him, so I’d watch this parade of young men and women sitting lined up for 10 minutes with Stephen. He’d interview 50 engineers and take 1.

Patrick O’Shaughnessy

Wow.

And he spent the time. We went to lunch one day, and I asked him, “So, what’s the first thing?” He said, “Well, the first thing is, I give them a question—a math question.”

I said, “Give me that question.”

He lost me after the word “the.” I had no clue what the question said. He said, “If they don’t get this question in 10 seconds—”

Patrick O’Shaughnessy

Then it’s over, yeah.

“It’s over.” He would throw them out.

They do stuff in the engineering community that, having come from entertainment, I wasn’t used to. I remember when I first went up to the Valley, I went to see John Donahoe, who was running eBay, and I had 2 young engineers from MIT who had an unbelievable technology. I was fresh up there. This was 20 years ago.

I called John and said, “I want to bring these guys by. I think you guys should buy this tech before we do this startup. It’s a waste of time. We’re going to do the startup. It’s going to be great, and then you’re going to spend a fortune to buy it, and these guys are going to have money and no job. Let’s buy them now. They’ll make some money, and you’ll give them heads of the departments or something.”

He said, “Great.”

We came into this meeting. We were in a conference room. John was sitting at the end. I was at the opposite end, and sitting next to me were my 2 young MIT geniuses. John marched in 4 guys from his engineering department. 2 of them were from India, 1 was from Stanford, and 1 was from the University of Illinois at Champaign—all pedigreed guys.

They started asking my guys questions like rifle shots, and my guys were answering them. Finally, I threw my chair back and said, “This meeting’s over.”

Everyone was looking at me like I was out of my mind, even my guys. One of my guys turned to me and said, “What’s wrong?”

I said, “I think this is disrespectful.”

He said, “What, are you crazy? They’re trying to dig into the technology.”

Patrick O’Shaughnessy

Yeah.

I turned red as a beet. We finished the meeting. John walked me out, put his arm around me, and said, “Welcome to the Valley.”

I said, “Is this standard?”

He said, “Get used to it.”

Patrick O’Shaughnessy

Yeah.

I said, “This is how people treat each other?”

He said, “Oh, this was nice.”

I learned the hard way. By the way, they bought the business. I learned the hard way that it’s not off-limits to ask tough questions, and I kind of ask those questions quietly.

I don't ask them. I manipulate my way around it in a meeting. So, to directly answer your question, my checklist is a series of things that fit into my cognitive frame of reference, weighted and predicated on previous experiences: how the person behaves, what their interests are, and what their social capacity is. It doesn't have to be great in the traditional way. What is their quest for knowledge? Are they motivated? Do they want to work hard? Do they enjoy working? Why are they working? What's the goal? And what's their raw processing power?

In 1999, I got a cold call from Marc Andreessen, and he asked to meet me. I met him for lunch. I budgeted an hour. I'm not a long-lunch guy, and I'm not a long-Zoom guy.

Patrick O’Shaughnessy

You're not a long-anything guy.

I'm not long on anything because I think it's a complete waste of time.

Patrick O’Shaughnessy

Except podcasts.

Yeah.

Patrick O’Shaughnessy

Except my podcast.

But I'm not in control here, Patrick. You are.

So I went and met with Marc at someplace called Hugo's in West Hollywood. Marc comes rolling in in a pair of shorts, a plaid shirt, mismatching socks, and horrible shoes, and we sat down. I'm saying to myself, "Oh my God, what have I gotten myself into here?"

Fifteen minutes into the conversation, I'm in a state of shock. I'm sitting with one of the smartest human beings I've ever talked to. Now, bear in mind, my best friend at the time was a guy named Michael Crichton.

Patrick O’Shaughnessy

Another one, yeah.

You can't get any smarter than that, or more curious or more interesting to sit around with. I'm sitting with his match, maybe better, and 3½ hours went by in 5 minutes.

At the end, he said, "Would you like to join my board?" And I said, "Why? I'm a raving idiot compared to you, and I don't know anything about technology." He said, "That's exactly what I want on my board. I want someone who's not afraid to stand up to all these tech geeks that are on my board."

Patrick O’Shaughnessy

I love the answer around 50 engineers, 10-minute segments. A common theme you see today—with Elon Musk being the prime exemplar of it—is that any ways you can increase your clock speed, save time, and get through cycles faster seems to define who wins.

Can you say a little bit more about time and the respect for time that you have?

For me, time's the foundation of everything, then relationship, because I can't get the relationship without the time. When I met you, I didn't know if I wanted to do your podcast. I didn't know you. We have a mutual friend who raves about you, but that's not enough for me because I may not agree with his perspective, and that happens to me a lot.

People will call me and say, "Can you meet with so-and-so?" It's not that I don't respect their perspective; it's just that I have a different one. For me, time's my enemy, and it's been that way since I was a kid. It has nothing to do with my age chronologically.

I remember being in high school, and I was running for student body president of a 4,000-kid high school. There weren't enough hours in the day for me to do what I felt I needed to do. I had to pander to so many constituencies that no one else had. I had to develop constituencies from groups that everyone had ignored.

No one ever went and spoke to the chess club at my high school. I was in high school in the '60s, and if you weren't an athlete, you were nothing. Your brain worked against you. If you were an intellect, they thought you were an idiot.

It was the '60s in the San Fernando Valley. If you didn't have athletic prowess or some kind of unbelievable skill set in something—like you were a great auto mechanic and could fix a '57 Chevy—something that demonstrated to a working-class community that you had something special, you were ignored.

So I went to all the clubs that were persona non grata to build a constituency outside of what everyone called the normal people, who frankly turned out to be abnormal. They all peaked when they graduated high school, all of them.

We had 3 teams, all-city, number 1. We had 9 of 11 players on our football team make all-city first string. One made it for 5 years in the pros and then got injured. The rest disappeared. Disappeared. They peaked.

So for me, it was about being careful with the time, careful on acceleration, careful on deceleration, and meeting people that would enrich my life intellectually, emotionally, and financially. It's important to add all 3.

I'm a capitalist, and I get into these huge arguments with people who are more socially leaning because it doesn't work. We've seen that over and over again. It's the capitalists who drive the foundation of giving. They make jobs.

Look, they don't do everything right. They do a lot of stuff wrong. Believe me, everybody does, me included. But by and large, it's a better system than Marxism or just being a pure socialist. I think our system's better than the Chinese system. You have 50 million communists controlling 1.4 billion people. That doesn't smell right to me.

I had lunch yesterday with a guy who's very smart named Steve Radner. I was commenting about what an amazingly great mayor Mike Bloomberg was, even though he got in by accident, because he was a business guy. He thought about everything in terms of getting it done: How do you do it? What's the path of least resistance? What's best for everybody?

You're not going to get it right for everybody, but if you can get it right for most of the people, how do you do that? You have to have a business background.

So I said to him at lunch yesterday, "I think that in order to run for governor or mayor of any city or state, or president or vice president of the United States, you have to have had 5 years of business experience. You have to show on your LinkedIn that you ran a business, period."

Yeah.

And that you had employees, and you had health care problems, and people had deaths in the family and needed days off, and somebody was getting a divorce, and you had to balance budgets, and you had to find where to raise money.

These are all things that are critical to running a business, which is a city or a state or a country.

It makes me think of the last 2 answers combined: the ideas of time and executive ability, like Steve Schwarzman's. I'd love to hear about the early days of Blackstone. He has this very famous mantra—"What's next?"—which he writes about in his book. He seems to be one of those people who's always dissatisfied with stasis, always wanting to know what the next thing we can do is that we've earned the right to do.

Yeah. I must say he's one of my heroes. I met Steve in the '80s. He was at Lehman Brothers, a very smart guy, very motivated, and wanted to do something special.

He and his mentor, Pete Peterson—Pete was on the board of MoMA with me. We got involved very early together because Pete was on the board of Sony, and I was Akio Morita, the founder of Sony's personal media adviser.

I got that position because he made a decision that he had better technology with Betamax videotape than Matsushita, also known as Panasonic, had with VHS. His technology was better, but they beat him. They killed him.

They killed him for 2 reasons. One, he had a maximum running time of 2 hours. There's no movie that automatically stops at 2 hours. Sometimes they're 1 hour and 50 minutes, but most of the time they're 2 hours and 10 minutes. So people couldn't record movies, which is all they used those machines for.

Oddly, they were all invented by an American company called Ampex, and they were invented for a reason that you'll never guess. They were invented by a bunch of engineers at Ampex in the United States to record pornography.

It always, always comes back to that—and pizza, technology.

Technology is all about porn and pizza and Diet Coke. But they sold the rights, and Sony bought them.

He said, "We sat for hours in Tokyo. How do I avoid this?" I said, "You have one shot. You can control the content." And I said, "It's a tough shot because it's not profitable, but no one's going to beat you in technology if you combine the 2."

So Pete was his board member, and they revered Pete—revered him. I put Morita together in my home with Kirk Kerkorian, who owned MGM, and the 3 of us met for 3 hours discussing Sony buying MGM.

At the meeting, Morita did something genius. He brought a box about 6 inches square, put it on the coffee table, and let it sit there. You could see Kirk just staring over at this box. It was so Japanese.

Finally, Kirk said, "I can't take it anymore. What's in that box?" Morita said, "Your future." He opened the box, and it was a handheld videotape recorder this big, about 4 inches big, with a little mini-tape in it.

Kirk played with it, used it, and videoed the whole meeting. At the end, Morita took the camera away from Kirk, put it in a box, sealed it, thanked him for the meeting, and said—

Kirk said, "Can I have the camera?" He said, "No, if you sell me the studio."

So we left. We tried to make a deal, but we couldn't make a deal.

Then I started getting involved with a guy named Walter Yetnikoff, who was a client of mine and ran CBS Records. There was an opportunity to take CBS Records away from the Tisch family, who really didn't want to keep it, and Sony became the candidate.

Pete was on the board of Sony, and I was working for Mr. Morita. We got to be friends aside from knowing each other from MoMA, so it made a great common denominator. Steve was the banker, and you'll die when I tell you who the number cruncher was: Roger Altman.

Mm.

He was at Blackstone at the beginning. There was a tiny little office that they had. But Steve had something that Pete didn't have, that nobody else had. Steve had my template, the common denominator among all these guys that I'm crazy about: a drive that had no end, a desire to do something different, a desire to break all the rules illegally, but not to stand on ceremony, and to create a financial institution out of thin air.

It's easy to look at it now. They have a $450 billion credit fund. I was having dinner with the heads of one of the banks in New York, and we were talking about Blackstone, and Steve in particular, and I said, "Would you ever have thought that someone from scratch would create a competitor to you in the credit markets?" Because they get the first call, you don't, and they're the biggest bank in the sector.

Steve had a drive and a brain, and I related to him so much because, in 1974, when I wanted to start CAA, I will never forget this as long as I live. An agent at William Morris, we were friends, and he said to me, "Why are you doing this? You're gonna fail." And I said, "What do you mean I'm gonna fail?" And he said to me, "No one could build an independent agency. There are 200 agencies. You're gonna get killed. You're not gonna get any clients. You won't be able to represent movie stars. You're not gonna get writers. You're gonna be looking for a job in a year. Why not just stay at William Morris? It'd be easier, and you'll make more money?"

And I kept sitting there saying to myself, "What's wrong with this guy?"

Yeah.

What's wrong with this guy? Steve was the same way. I know people said to him, and they'd talk behind his back, "Yeah, yeah, Blackstone, sure. It'll be a boutique bank, great. Maybe someone'll buy you." Well, look who's got the last laugh now.

CAA's 50 years old. Blackstone's an institution. It's all about the founder, and Steve had a vision: "I'm gonna be an institution." He never stopped. So when we started, we started representing people on television only. Then we went to movies, then to music.

What's next?

We just kept going: investment banking, advertising, consulting. Steve did the same thing, one business line after the other. But the genius move is the people. Same as Stefan Cohen at Vallander: get the best people. Pick up the best men and women in the financial universe, pay them more money, give them more freedom and creativity, and let them run.

Now you go into the Blackstone building, and it's like, you know—

Crazy.

It's crazy. It feels like it's been there 100 years. And this is what Andreessen Horowitz are doing. Ben and Marc are building an institution that's gonna outlive them, and that's their goal. They don't wanna be a boutique. They don't wanna be small.

One has to admire that vision because it's the driving factor to success, and success spawns philanthropy, jobs, social movements, and basically the running of the wheels of the economy. It's much different than a couple people being in charge of everybody. I said to someone the other day, "I wouldn't wanna be a startup guy in Beijing if my life depended on it. I don't wanna see what happened to Jack Ma and say, 'Oh my God, I wanna kill myself to do this, but I gotta walk around quaking in my boots.'"

We live in the greatest country in the world. I don't care what anybody says about anything or any elected official; it's not gonna happen here. We run our own lives, and we're creative. I'll put our tech scene up against anyone's in the world, hands down. We'll kill them. We'll kill them. We're just motivated free thinkers.

It seems like momentum is such a critical ingredient in all these stories. Again, this is time cut a different way, I suppose, but the what's-next mentality of Schwarzman, the platform-building and institution-building of Andreessen Horowitz, the way you built CAA, the race to scale—even what you're doing now with Ali at Treyville—it just seems like you have these ways of installing systems that create momentum.

I think at one point you were running a daily fundraising meeting when you were raising a new fund, like every single day.

I'm still doing it.

Still doing it.

Still doing it.

So what are those things—

I haven't asked you for money yet.

Yes, you have. I would love to hear some riffs on momentum. It seems like one of the things you're exceptional at is systems for creating it and maintaining it, and I know you believe deeply in it as a personal brand.

No, it's a postulate for me, and it's a great question because it's highly overlooked. They don't teach it in business school. As a matter of fact, in the curriculum, most business schools are impractical. They don't teach the things that I needed to know. No one taught me how to be an investment banker.

I wanna ask about that, too.

I can look at a balance sheet and read it, but so what? So can everybody else. There's only 4 or 5 numbers that mean anything anyway. But they don't teach you about momentum.

Steve Schwarzman understands momentum. Alex Karp understands momentum. Marc Andreessen understands momentum. Josh Kushner understands momentum. Bill Ackman understands momentum. Teddy Forstmann understood momentum. Glenn Lowry understood creative momentum.

All these executives in their varying silos never took no for an answer. If they were shut down in one silo, they went right to the next. They hired people that could take their jobs. I remember when some of these executives hired people and there was all this back-channeling: "Are they crazy? They're gonna take their jobs."

I remember Steve hiring a guy to run Blackstone, who we all know is fantastic, Tony James, and everyone was saying, "Steve's leaving?" And my answer was, "He just got an amazing guy, makes him 10x stronger than he was." He had confidence.

I had a meeting yesterday with a young guy that Ali and I are recruiting, and I called Ali after the meeting and I said, "We've gotta shore this guy's confidence up. He's much better than he thinks he is." Which is odd for me to say because, as an employer, you want them to think they're not, so they're weak. I want him to realize what his strengths are, to make a decision from a positive place, not a negative one.

All these people that I've mentioned are all about momentum. In other words, they remind me of this toy I bought my grandson that's a remote-control truck that, when it hits a wall, bounces off and turns in the other direction. That's kind of these people. There's no stopping them, and there's no idea that isn't worth considering.

At CAA, we had, every 90 days, a gong show, and we lined everyone up in a circle—250 people who were working executives. They were all seated within an inch of each other, tight in an oval. They had 90 seconds to present a new idea. I didn't care what the idea was. We got some amazing stuff out of it. Just when you think there's no new ideas, you know? That's what I love about technology.

What are the top enemies of momentum?

That's easy: loss of confidence and fear of failure. Fear of failure is the greatest problem outside the United States. So I was in London a couple months ago in a business meeting with 5 or 6 businesspeople, and one of them looked at me and said, "How do we do this?" And these are prominent people.

I said, "You do what?"

He said, "You've been up, down, and sideways, but you never stop, and you don't take no for an answer, and you just keep building. But you know how to build off success and off failure." He said, "If we fail in Europe—"

It's over.

It's over. We run away, we're embarrassed, we're never allowed to come back. I said, "If we fail in America, we take it as a badge of honor."

I can't tell you the number of pivots my young companies have made. I mean, Kevin Systrom's fourth pivot was Instagram. Fourth. I have a young kid I love. I've mentioned him before, James Proud. That deal failed the first time. The second one was a huge hit. You can't stop.

I think if some of these great entrepreneurs—when Mark and Ben wanted to start, everyone told them they were crazy. There were 190 VCs on Sand Hill Road. They were gonna be another one. It didn't matter what their background was, that Ben was a brilliant operator and Marc invented the browser. It didn't make any difference. What did they know about investing?

Speaking of one of your—not pivots, but evolutions—how did you teach yourself investment banking? What was the story of getting into it? Why did you do it? And I'm especially interested in, if you compare the first deal or 2 that you did to the last deal or 2 of that chapter, how you most changed how you did that job.

It was strategic. We had conquered all areas of entertainment. We had a 76% market share of talent. We had 46 of the top 50 grossing directors in the world. We controlled almost everyone except Disney's motion-picture offerings. That was 10 different studios.

We packaged everything. We made the biggest hit movies of anyone. Added together, the biggest hits came out of CAA, from Jurassic Park to Out of Africa to Ghostbusters to Stripes, Meatballs, Casino, Goodfellas. I can go right down the list. It just was endless.

And we had great commercial taste. Great commercial taste. We all loved movies, so we basically picked movies we wanted to see, which always amazes me today when I look at the offerings and I say to myself—

Who's picking this stuff?

Who's picking this stuff? Who'd they pick it for? Because I'm not really interested in this, and I view myself as a normal moviegoer.

But we had hit the top in every area. I was sitting back one day and saying to myself, “There’s a transition going on in the business.” The businesses in between—the distributors, the studios—were too big to be independent and too little to grow because they had no capital. They relied on what their content did. So if they had a 30- to 35-movie slate, which was about average, they were thrilled if 2 were hits, 2 were zeros, and the rest floated in between. But that’s not a money-making business, believe it or not. People didn’t get rich in the studio business.

So I realized that what was gonna happen was that these companies were gonna need sponsors. They were gonna need money. It was pretty clear. It was not some genius observation.

Yeah.

They were dying for cash flow. I could tell because we were having trouble collecting. They’d put us off. We’d get paid for our clients because they had guild rules. But, man, they waited until the last possible second to send the check. We used to have to send messengers to Paramount to get paid, to pick up the check. Do you remember checks?

Vaguely.

They were on paper. And I said, “Wouldn’t it be great if CAA not only had all the clients, but we had all the owners?” We were the ones they had to talk to.

Japan was on fire. On fire. They were producing everything we weren’t producing—everything we’d stopped producing. It’s fascinating to me to this day, because I am such a zealot for America right now. At the end of the day—and I agree with Alex Karp—we better be strong. We better just be strong. Andreessen says the same thing. Peter says the same thing. Anyone I know who’s smart says the same thing. We better be strong. You don’t keep the world at peace by being weak. You just don’t. No one understands weakness. They just don’t, and I surely don’t. I don’t understand it in people because there’s no reason for it.

We all have individual skill sets. Be confident in those skill sets. So I started to cultivate companies in Japan, and the first company I cultivated, oddly, was Nomura. And, oddly, in those days, in the ’80s, they controlled about 3% to 4% of the stock in the top 20 keiretsu companies, which no one knew. They hadn’t invested in them. So they opened a lot of doors for me. I was their media consultant.

When I met Mr. Morita, it became very clear that their money would be very good for American assets. I was highly criticized. The cover of Newsweek bashed me. It had a picture of the Statue of Liberty wrapped in the Japanese flag and ran a nasty article saying that I was selling all of our assets to Japan.

I’ll never forget this: my friend Bill Bradley, who was running for president at the time and was senator from New Jersey, gave them a quote that shut it all down. He said, “Did you ever think that he’s using this for financing? Because they can’t take the studios over to Tokyo. They can’t. They don’t understand how to make the product.”

So it was a no-brainer. They were just good money. With technology, it was a great fit. The fact that they didn’t all use it right is a different story. That’s because they had no interest in growth. They think in a very organized fashion.

I booked Michael Jackson at one of the Tokyo stadiums. They had 60,000 people there. And we had him at Soldier Field in Chicago—100,000 people. When he finished at Soldier Field, there was pandemonium from the Chicagoans. They went wild and ran for the exits and the field, and they went crazy.

When I was in Tokyo and Michael Jackson finished, everyone applauded, and then some guy in a yellow blazer came out to the diamond with a microphone and started dismissing rows one at a time. And I said to myself, “I learned so much—”

In that moment.

In that moment, I learned so much. It was unbelievable.

We are not brought up in an organized fashion. We rebel against authority. We don’t like people telling us what to do. We like original thinking. Failure is an option. Let’s just get on with it. That’s America.

And the great thing about America is that we create movies, we create television shows, and we create books. We’re the masters of fine art now. It used to be all Europe until the ’50s. Then came abstract expressionism, then pop art, then op art. It just kept going. We have the number-one artists in the world here, in New York City, all over the United States.

So when it comes to tech, we’re wide open. For me, it was about getting to a point where no one could talk to the owners of anything without going through us. So if you wanted to talk to the owner of CBS Records or Columbia Pictures, they spoke fluent Japanese, and if you didn’t have a long relationship with them, you had less than zero chance of having a definitive conversation. So it all funneled through us.

Hmm.

So we had the owners of MGM, which were Crédit Lyonnais Bank, whose chairman I was a consultant to. We had the owners of Universal Studios, which was Matsushita Electric, and we had the owners of CBS Records and Columbia, which was Sony, and we had the owners of Bertelsmann. I was a consultant to BMG. And that was pretty much 3/5 of the business.

We didn’t have Disney, but they’re always on their own. And at the end of the day, you needed a favor, and that’s all that business is: one favor after another. You had to call us. You couldn’t call anybody else. Who are you gonna call? Ghostbusters? Yeah, I said, “Who are you gonna call?” There’s no one to call.

Try getting Jean Percival, the chairman of Crédit Lyonnais Bank, on the phone. Good luck. It just doesn’t happen. It’s not simple. And remember, in the ’40s, ’50s, and ’60s, up until the mid-’70s, you could get any owner of any studio on the phone. You could see them in a restaurant. That changed fast, and we saw it coming.

It’s so interesting to think about the evolving business model, where the underlying thing is the same: you just are the nexus point for coordination in this entire world. What was the most fun part of that chapter, of doing those very big deals? I remember that story in your book, but I can’t remember which deal it was, when you netted the fee to you and CAA. It was something like $60 million or $70 million at the time, after you paid everyone else off, and that was just a massive dollar amount.

Well, that was 40 years ago.

Yeah, so it’s probably $200 million equivalent now or something. What did that teach you? That seems like a really important moment in—

Well, it’s what we’ve talked about. It’s—

Yeah.

You asked me how I learned to be an investment banker, and to answer your question—which I’ve avoided skillfully—my oldest son, Chris, asked me the same question when I was doing it. He said, “Dad, how the hell did you figure this out? This is complicated stuff.”

I said, “Chris, I learn on the job every day.” I watched Steve Schwarzman. I watched Pete Peterson. I used to go to lunch with Roger Altman and pick his brain. I am an insatiable sponge. If I can get 30 minutes with Marc Andreessen or a meal with Peter Thiel just to listen, to me, that’s a quadruple net positive because I learn so much.

I have to tell you that I didn’t know what I was doing, but I didn’t need to. I learned it as I did it, because it’s pretty much common sense. I could read a balance sheet. I knew what the SEC checklist was and what had to be met. I had Herb Allen II as my mentor, telling me what to do and what not to do. If I was gonna do something incredibly stupid, he had the nicest way of telling me how stupid I was. Herb and I were on the phone 10 times a day.

What did he teach you? He seems just like such a fascinating, incredible—

Herb is the most extraordinary man on the planet, and by the way, so is his son. I can tell a lot about a guy by their kids. The most I learn about a human being is by meeting their kids.

I have more notes from my first meeting with Herb Allen III on my iPhone than I have from maybe any other meeting in recent memory.

He doesn’t talk much, doesn’t do press. You Google them, there’s nothing. The family’s amazing.

Herb Allen II was my mentor in banking. I went to him with these ideas, and instead of saying no or trying to steal them, he said, “Let’s do it.” He didn’t push me away. He didn’t think I was nuts. He thought it was a great idea that he and I do it together. Every other bank tried to push me out.

When I signed Matsushita as a client, they took me into a room, like a cubby room, and there were stacks of engagement letters from every investment bank in the world, in the world, laying out all their fees and everything else. And Herb said to me, “Don’t ask anybody for anything.”

So I went in, and when I closed the deal with Matsushita, a man named Hirata, who was the senior vice president—the number-two guy in the company; that’s how they worked it—said to me, “What would you like?”

And I said, “Nothing.”

He said, “What do you mean, nothing?”

I said, “If we’re successful, I want you to get a Brink’s armored truck, load it up with gold bars, and send it to Beverly Hills to my office. If we’re not successful, cover our expenses. We get nothing.”

He bowed so deeply that his head hit the table, because it was trust. We never had a written document. In 25 years at CAA, I didn’t have written documents with employees or clients. We never lost a client the whole time I was there. They—

You never had a written document with a client?

No. Sometimes we had what were called guild authorization papers, but they didn’t mean anything, because under the Screen Actors Guild, within...

If a client didn't work for 91 days, they had the right to fire you. Why have a contract? Because it just gives them something to look forward to. I had people stay with us 25, 30 years, never signed a document.

Wow, that's so cool.

But Herb said, “Do it.” I did it. He was right. I did it with everybody. I never asked Sony for anything. I never asked MGM for anything. I never asked Crédit Lyonnais for anything. Bertelsmann—I never asked anybody for anything. I just got paid, and I got paid obscene sums of money, but we gave them really good advice, and we gave them advice they couldn't get from anybody else.

So when we were diligencing the Columbia Pictures library, I had 6 of our guys in the library looking at the names of the films, and they had seen them. They weren't just bankers. They were hyphenates. They had seen the movies, so they could say, “Yeah, this has value. No, this doesn't have value.” They couldn't get that anywhere else.

We were spot-on with what we said the libraries were worth because we didn't inflate it. The other thing we did, which is quite out of the ordinary, is we told the truth, and that drove people crazy in the entertainment business. To tell people the truth was unheard of because the untruths were what drove the business.

Why did you tell me one time that one of the worst things that happened to you was being number 1 on that power list for 8 straight years?

Oh, I hated it.

I can't remember which magazine it was.

No one understands how much I hated it. I don't even remember the name of the magazine, but it was a very nice woman who was the editor. When I saw that, I panicked because that was the beginning of shots being taken, and there's just too big a chance that one of them's gonna hit you.

Why does it matter?

Because someone said to me, “Why did you start this business with Ollie, who's 40 years younger than you, and have all these under-30 people working around your office?”

And I said, “Well, 1, it's stimulating. 2, I'm learning a lot from them. 3, they know things I don't because of their age. 4, they're all really smart, so for me, that's like a feeding zone.” I'm a big Dracula devotee. “And 5, the build is the most fun.”

The best time of my life was the first 10 years of CAA. The worst time was when we came out—

Number 1 on the power list.

…number 1 on the power list, because then everyone wants to kill you. And they don't just wanna kill you, they wanna hack your limbs off and just drag them around the courtyard. Either you can't do what they want you to do, you can't make their dream come true, you can't help them, or you don't help them enough. It's a never-ending litany of problems.

Human beings are basically unsatisfied at every level of their life, except for moments, and the goal is to have as many of those moments as you can.

Are the moments, just to hearken back to the name, all fundamentally creative in your experience?

No, they… Look, some of my greatest moments are with my grandkids. I love having grandkids because I get all the fun and none of the responsibility to raise them, but I get to see my kids in them and a little bit of me, and it's really fun. Doing things that are creative is fun.

For me, business is creative because I'm not a painter or a director or a sculptor or an actor. I have no talent, so I can't do any of the things that I just so admire. That's why I could sit and watch Roy paint. I love the concept.

We were on a vacation together on a boat in the Mediterranean, and Michael Crichton was sitting at his computer. I said, “What are you doing?” He said, “I'm making notes about this town we just went to in Italy.” I said, “What about?” He said, “Well, things I saw that were weird.” “To what end?” “I'm gonna put it in the file, and I'll use it.”

What I realized is that, like a quilt, he would patch all this stuff together into a yarn, and it was either true, false, fiction, nonfiction, but it was a yarn and it came out of nothing. It came out of his head from life experience.

Reminds me of Danny Meyer's “Always Be Collecting Dots,” ABCD. It's kind of a beautiful idea.

Danny Meyer cracks me up. I sat next to him at a MoMA trustee lunch. He's not on the board, but he's very close to the museum, and he was catering it. He fits my description to you of the kind of people I like to be around.

Yeah, totally.

He sat there, and he didn't sit still. He's looking at everything. He's jumping into the kitchen. He's talking to the captain. He's talking to the waiters. He wanted perfection, and to me, that's what it's all about. It's about excellence.

If you can't live your life and achieve some excellence in some silo, then you should move to another planet because that's what it's like. It doesn't matter what the silo is. I had a guy in Los Angeles who was the greatest auto mechanic I ever met in my life. I used to take my cars to him when I was younger because I love cars and I had all these old cars.

I don't know how he did it. He could make them run. I thought the guy was a genius. He was a guy who lived in Little Tokyo in Los Angeles, and he was brilliant at his field.

Why is excellence so important to you? Or why do you get frustrated by people who don't live up to their potential? Kind of the same question.

'Cause I think it's a waste. I guess, as an agent, I've mentored so many young people, and I so enjoy it, but the best part of it is seeing them succeed.

I said to Ollie, “Look,” I said, “You're 40 years younger than me. I want to leave this to you and now to my son, who's joining us. I want you guys to have some foundation that you can quadruple. It's my job to give you that foundation. It's not for me. I already have my career.”

There's 3 things that you've said to me that always stand out, and they're in concert, and I'd love you to reflect on them. One is that you're the world's best friend and the worst enemy. The second is that nothing that you do is by accident. And then the third was from your book, which is something to the effect of: you grew up being bullied and then spent your career bullying others in support of your clients.

Well, I'll take the third one first because I told this story to someone yesterday. Years ago, Bob De Niro was a close friend and a great client, and he and Marty are best friends, and we did 5 movies together.

Occasionally, competitive agents, even though we really didn't have any competition, would somehow eke their way into our clients' good graces with a meal or a meeting. It was highly unusual. So some agent, who I don't want to mention because he's still functioning, gets Bob De Niro in a room here. Two things happened in the same week, one with Bobby De Niro and one with Bill Murray.

With Bob De Niro, he says to him, “You know, Bob, Ovitz is too busy, too many clients, too tough, too much in control. You're losing all your creative judgment, and he's impossible to deal with.” And then he called me all kinds of names that I took as a compliment: that I was too tough and that I was a bulldog. To wit, he has bulldogs on his desk in his office, which is true.

Bob looked at him for a second while he was having coffee. Bob told me this story, and he said to the agent, “Yeah, you're right about everything you said. But you know what?”

The guy said, “What?”

He said, “He's my bulldog.” And he left.

With Bill Murray that week—this is hysterical—a different agent got Bill Murray to have a meeting with him. They were supposed to meet at the Mark Hotel, but Bill was late, and he said, “Come up to my apartment.” Bill didn't know what the meeting was about. He didn't even know the guy was an agent.

Bill, to this day, is one of my close friends. He's one of the smartest, most gifted human beings on the planet. He is a gift to all of us because he's all about making people feel good, unless he thinks you're a joke.

Bill was meeting with this guy in his own apartment, and the guy started pitching him on why he should leave me. Bill shook his head and said, “Could you excuse me for a minute? I've got to go to the bathroom.”

The guy said, “Yeah, sure.” So Bill left the room, and this guy sat there. 5 minutes went by, 10 minutes went by, 15 minutes went by, 30 minutes went by, and he went looking for Bill. Bill went out through the fire escape and left him in his apartment.

I love it.

Yeah, true. All true. You can't make this stuff up.

Why? So, best friend, worst enemy; nothing's by accident, everything is incredibly deliberate.

Look, I'm a zealot and a passionate human being about everything I do. When I started collecting art, I started collecting prints. Now I have a very deep and strong art collection. Not an accident. I've worked really hard at it because I enjoy it, so it's fun. It's rewarding. I envy what these people do.

Tamar and I will sit around sometimes at night after dinner and look at the art on our walls and say, “How did they do it? Why did they do it? Why'd they use that color? What drove them?” It's so interesting. I don't know how anyone could not think that. It's just so interesting.

Take yourself to that moment. What was Picasso thinking when he decided to deconstruct a figure and make it a Cubist look, where it's like a puzzle? Pre-computer, 100 years ago.

One of the coolest things I've seen of yours was the Picassos with the statues that—

The African Mask.

That’s what influenced me to go to MoMA. One of our directors, Bill Rubin, did a show I saw probably 25 times. He came up with the thesis that Picasso and all of those artists—Gauguin, Rock, all of them, Modigliani—were influenced by African statuary from the mid-1800s.

Because in 1850 to 1900, the Nigerians threw the Catholic missionaries out, so they went back to Paris and Brussels, where the greatest primitive art museums are, and they brought all these reliquary figures with them. And in the early 1900s, they ran out of money and put those masks in those Left Bank shops, you know, on the weekends.

Picasso bought 50 of them. He probably spent 2 or 3 francs for each one. There’s a picture of his studio in Mougins, in black and white, that has 50 masks on the wall. You look at these masks, and you look at the faces, and you go, “Good God, it’s right here.”

And Rubin proved that with these 2 volumes that are amazing. I saw that show so many times and started collecting African art the same day. Then I started looking at Picasso very seriously before anyone else. This was before Picasso took off.

As a matter of fact, there was a period in New York in the early ’70s where The New York Times had written a vile review of the late Picasso show at the Guggenheim, and all the dealers had stocked up on it because he had painted 10,000 pictures. It wasn’t hard to get, and it all just sat there. No one would buy it.

And not to disagree with The New York Times, but I went in and bought 3 paintings for nothing.

Hmm.

They were thrilled to sell them to me.

Crazy.

Because I thought he was a genius. They re-reviewed the show 3 months later and said they had made a mistake.

But those are all things that are important. For me, it’s about excellence, and it’s about being the best friend. I want to be the best friend I can be to my friends. I want there to be no question of my loyalty to them.

It was the same with my clients. I did not work for the movie studios. I didn’t care what they thought of me. I didn’t work for the networks. I worked for the clientele of CAA. That was my job, and I worked for my associates.

I wanted them protected. I wanted us to function in unison—client and agent. We had a young agent. We all had assignments, everybody including me. Her assignment was Warner Brothers. The guy running the studio wouldn’t return her calls, which was weird because we had everybody he needed, but he wouldn’t talk to her. He would only talk to more senior people, and we forbade that.

We insisted that if you, Patrick, wanted to package someone in your O’Shaughnessy production, you dealt with the agent who represented CAA and all our clients. That was our conceit. You didn’t go to the agent who handled the client.

The guy shut her down. In a staff meeting, much to everyone’s chagrin, I told everyone not to return this guy’s call, period. No emails, no calls, no communication until further notice. This went on, and about 3 days in, he called me. I didn’t return his call.

5 days in, his wife called me. I did return her call. She said, “Why are you doing this to Bob?” And I said, “Why is Bob being disrespectful to Lori?” She said, “What are you talking about?” I said, “Ask him.”

So she called me back and said, “He’s taking her to lunch.” Then we started calling him again because that kind of movement matters. Now, he hated me for that, and I don’t blame him.

The team probably loved you.

The team loved it because they felt supported. Clients loved it because we taught them a lesson, and we became even more powerful. At the end of the day, power was synonymous with success in getting things done as an agent.

I’m only talking about being an agent because we were there to protect the clients and to protect the constituency. So, was I a good friend to that guy? I was until that moment, and then I decided I wasn’t going to be because he shouldn’t have done that. He embarrassed her to death in a staff meeting. She turned red as a beet. She couldn’t give a report.

So, world’s worst enemy, one of my close friends in Los Angeles called me up and said he needed to see me. He said he had been sued by a woman who worked for him 30 years ago because he thwarted her career. This was not sexual harassment. He never touched her. He thwarted her career.

I said, “Give me every fact.” He did, and I went on a campaign on his behalf because it wasn’t right. It was 30 years ago. She did just fine, but the judge wouldn’t throw it out.

I’m his friend, and I did some things that probably other people would question. Nothing illegal, but I called the lawyer for the plaintiff, whom I know, and gave him my point of view, which was not particularly friendly. I thought that it was shaming his firm, and I told him that. I told him I was going to tell everybody else that too, because I thought what he was doing—what his associate was doing to this man—was not only inappropriate, but there was no legal ground for it, and it was 30 years ago.

So, yeah. Am I the world’s worst enemy and best friend? I think so, and I’m proud of it.

We just finished the NFL season. Tell me about Roger Goodell, someone I know you think very highly of.

I’ve been friends with him. I just had dinner with him. We were laughing about how long we’ve known each other. I met him in the early ’90s. I don’t know what happened. He’s one of those guys. He was number 4 at the NFL when Paul Tagliabue was there. He had something very special. He fits on that list.

Yeah.

He had something very special. He was really smart. He had the best bedside manner of anyone I ever met in sports, anyone I met anywhere. He was fun to be around. He knew the game cold. He knew his stuff.

It’s kind of like Andreessen or Horowitz knows their stuff. I remember sitting with Mark and Ben at a Y Combinator day, and every presentation, Mark would go, “Yep, 19, so-and-so. Saw that, been there, done that.” And Ben would say, “Yep, that didn’t work.” The frame of reference and the memory are frightening.

Yeah.

Roger just knew the game. He knew everything. He couldn’t have been more accommodating to the things we were trying to do. I was trying to buy a team for Los Angeles at the time.

Yeah.

We got to be good friends, and it never stopped. It’s now, I don’t know, 40 years later, and I think I got into a mega, mega argument with his wife at dinner last week, which he’s going to kill me for saying this, but I can’t help myself.

I said, “You know, you actually should be President of the United States.” I said, “You’ve run a business that’s humongous. You’ve grown it 20 times. All the owners have made a fortune. There’s nobody losing money.”

I said, “You should run for senator. You should do something. You should do some good for somebody”—aside from the 32 owners. I thought Jane Skinner, his wife, was going to leap across the table and throttle me.

But you never met a guy with so much integrity, so much creativity, so much ability to communicate, so much of the blind Lady Justice between players and owners. He’s absolutely fearless taking an owner to task. Fearless. He’s been this way since I met him. He didn’t grow into that. If he doesn’t agree with them, he just says it. They respect it.

On top of it, his dad was a senator who took a position against his party, and Roger has something to prove and has proven it 100 times over. And you want to talk about a loyal friend—he’s up there. He makes me look like an amateur.

Pretty cool.

Yeah.

If you think about your arc from agent to banker to all these other things you did, now to investor and working with so many investors, is there anything between those 3 categories that is most distinctive? Are there things in the investing world that just require something different, or is your approach very different than it was in the private sector?

It’s a great question. I got asked this a couple of weeks ago at a dinner I was speaking at, and Mark Andreessen and Ben Horowitz said to me in the early 2000s, “You’re wasting your time doing all the stuff you’re doing, because what you do is exactly what we do. There’s no difference.”

“You find an idea or a young person, so that could be a director or an actor or an idea from Michael Crichton, and then you develop it, and then you finance it, you give it money. Then you help them shape the business or the package, then you cast it, and then you get it distribution, and you market it.”

That’s the definition of a startup. There’s not one thing in my day-to-day that I’m doing differently than I did in 1974. There’s not one thing different. It’s just that the numbers are a little different, but it’s the same blocking and tackling, the same fundamentals.

At the end of the day, for me, I have a very cultural bias in how I invest. I invest very differently than everyone else. It’s the same fundamentals, but I invest in human beings. I may not like their idea, but if I like them, I want to be around them.

I’ve put my money into companies that have gone through the roof, and I’ve put my money into companies that have failed. But the founders have never failed me. They’ve always come back.

What do you think’s going to happen in the future of media? It’s changing so fast. AI is introducing unlimited content, basically.

First of all, I’m not as worried about AI as everybody else is on the content-creation side. I happen to feel it’s going to be a big benefit in production, especially in production planning.

With respect to creativity, I remember looking at Pac-Man. Do you remember that game?

Of course.

How many years ago do you think that was?

40, 50 years ago.

Great. So today, you've got full-motion video with emotional looks on game characters. That was unheard of in those days, right? You're going to get the same thing with AI.

There's no emotion now. Will they get there? Maybe. It's still a handmade craft. I don't think content's the issue. I think the issue's ideas, where we've kind of run the gamut on it.

Everything's a sequel.

Everything's a sequel. When I started as an agent, I bought a 20-volume set of the synopses of the greatest literature in the world, and I would go through it to see if I could find ideas for movies. Some of my favorite authors of all time, like Alexandre Dumas—how many times can you make The Three Musketeers or The Count of Monte Cristo, right? The French just made it for the 5th time.

We've kind of bled the well dry on source material. And then the fiction that's coming out isn't coming at the rate it used to, because we don't encourage young people. We've got a humongous problem in the arts—not in the fine arts, oddly, but in the media arts—of teaching people and giving them an opportunity.

When I signed Tom Cruise when he was 19, I gave him a list of 10 directors that he needed to work with to build his career. All 10 were clients, and he worked with all 10 over 10 years. That's a career builder. You couldn't do that today.

Someone said, "Could you start CAA today?" I said, "No." There's no marketplace for it. If someone had said to me that Netflix, or a company out of San Francisco that mailed DVDs, was going to change worldwide viewing patterns, and that everything would be put up, accessible in multiple places on the internet in perfect quality when you wanted it, I would've thought you were smoking crack. They changed the viewing patterns. No one watches TV the same way anymore.

In the '80s and '90s, you watched Thursday night on NBC because you wanted to see Seinfeld and Kelsey Grammer and all these shows. On Tuesday nights in the '70s, you watched The Mod Squad and then Marcus Welby, M.D., and the Tuesday night movie. That was just the way it was, and you'd talk about it the next day at the office.

Well, first of all, no one's going to the office. Second of all, nothing's ever at the same moment, so no one's talking about anything. It's very hard to build word of mouth, and it cracks me up when these releases are made that such-and-such streaming show had 3.4 million viewers. I crack up because in my day, late night, which was the lowest-viewing center on television but very profitable, Letterman drew 5 million viewers every night.

The day is over, and theaters are tough to go to. Until someone puts capital into the theaters, people don't want to go. You can now get a 100-inch flat screen for around $2,500 max. You can get a surround-sound kit from any of the big Japanese manufacturers for $499 at Costco or anywhere. You get your own little theater, and you can put it in your bedroom, your living room, or your bathroom. It doesn't make any difference.

I just bought a 4K projector that's about 6 inches wide that projects a picture on the wall in my bedroom. It's unbelievable. Technology has just swamped the content possibilities, and we're not growing creative people. Who's the next Steven Spielberg? Who's the next Marty?

Why is that? How do we do that?

You need a fertile marketplace. As I always said when I was at the agency, we're in a business, folks. It's fun to make movies that no one wants to see except the person who makes them because it's some personal statement, and that's fine, but we had a rule: 1 in 3. If you didn't make 2 commercial movies, you were not making an art movie.

Today, go look at the things nominated for Academy Awards and show me the breakout movie. We used to have movies that had an aesthetic value and a commercial value, and when you pushed them together right at that line, they were Tootsie, All the President's Men, Jurassic Park, and Rain Man. Rain Man was a humongous hit. That movie was turned down by everybody.

What do you think the key is to raising money?

Confidence. On the other side, the people you sit with have to have confidence in you that you're going to be diligent about it. Fortunately for me, I don't go into a meeting where people think that I'm not going to take it very seriously. I view other people's money as my own because it's all intermixed, and they also know I hate failure. I just have a thing about it from the time I was a kid.

When I grew up, failing wasn't an option for me because failure was death, frankly. I grew up in a very low-end neighborhood, and my dad worked his ass off but never could make anything of himself. I didn't want that life, and failure was not an option. So it was kind of a life-or-death decision.

I approach everything, including my relationships with people, like I told you about my friend. He's my friend, and he was being wronged. I'm not a judge, but I'm a judge in that situation for him. I'm his advocate. Am I right or wrong? I think I'm right, but if I'm wrong, frankly, I don't really care. Unless he did something egregious, I'm right.

If you sum all this up—and I think about all the lessons I've learned from you in closing here—I bet a lot of people would want to sign up for the sheer amount of experience that you've had: the ability to enjoy so many people, so many works of art, and to help create things; just the prolific nature of how you've worked and lived.

What's the North Star behind all that? Is it happiness? Are you seeking happiness? Do you care about that word? Is it something else? For those who say, "Okay, great. If I'm optimizing for this, I can maybe live something like you have."

Let me give you the foundation for that answer. Every Sunday for 50 years, I do the same exercise. Hell or high water, I've never not done it. I look at my calendar from the week before.

In my early days, I had a paper calendar, a thing called a Day-Timer. It was a little book with 30 pages, 31 pages, and you carried it in your suit pocket. We all wore suits in those days, by the way. It had everything you did every day. That's how I wrote my book, by the way. I had all those from it.

Oh, wow.

Yeah.

Cool.

I look at that every Sunday. I sit down at my desk, I open my calendar—now it's on Outlook—and I have my Outlook calendar on the left screen and my Outlook calendar on the right screen. The one on the left screen is the week before, and the one on the right screen is the coming week.

I go through every single meeting I had, every transaction, every human I met; it could have been social. I decide whether they go on what's called the Sunday list. On Sundays, since I don't do anything, I put on it the names of people I want to get to know better. Then I parse through the week—the names from the week before that I want to reengage with.

They're either people I found wildly intelligent, people I thought were doing really interesting things outside the scope of my expertise, people I made money with, people I lost money with, or people I thought bored me to death. And then there are some people I meet where I can tell in 5 minutes it's a giant mistake. They don't go on the list. Then the list gets carried forward. I've done that my whole life.

I want to basically achieve a state where I'm happy doing what I'm doing. I have no interest in retirement. I hate golf. I do my art, and it's more stimulating. I don't know how to say this: when you have less time, things are more interesting because you have to get it done, and it's more fun.

I don't want too much time on my hands. I want to be stimulated. I want to meet interesting people. I want to have interesting dialogue. For me, it's about achievement and learning. I want to learn something every day. I'm a voracious reader. I want to do interesting things.

I don't want to sit idle, and I don't want to not work. Work for me is therapeutic because I'm helping. At this stage of my life, I'm not building a career. It was a different phase for me. I am helping people, and I want to do that.

I help young people with companies, and I really like it. I help the people who work with me. I'm very excited because my son just joined us on the venture side, and in 2 weeks he's taken a load off me that's unbelievable. The reason it's unbelievable is that it gives me more time, and time is my most precious commodity.

I think that's a beautiful place to close, Michael. Thank you for the ideas, for the stories, for everything.

Patrick, it's a pleasure. I always love talking to you.