驾驭愤怒、滚动电话与打造娱乐帝国｜Ari Emanuel、WME 与 TKO

Correct. This is like a caged tiger. No stories, just having a conversation, because I prefer having a chat. So tell the story. Dana told you the story about Philippe Dauman, or Phil?

Let me back off a little. We were just talking. The funniest story anyone has told on the podcast so far is Dana White’s. He says, “Let me tell you about this guy named Philippe Dauman.” He says, “His name is Phil Dauman, and he’s from Jersey, [expletive].”

And then you say, “That was a fun meeting.” Here it is.

So, we’re here: The UFC has taken off on Spike, right? Our contract ends. This is from when we had the reality show and some fight nights. Then we called a meeting. I was representing them. There were Dana, Lorenzo, Frank, myself, Spike’s boss at the time, Phil, and I think one other person—his other co-CEO or whatever.

We were trying to convince them that they had to consider it a sport. It wasn’t a reality show, et cetera. He says, “I knew this was bad.” He says, “We created them. If they leave, we’ll get someone else and replace them.”

Dana and Lorenzo—I had known them for about 3 years at that point—were ready to explode. Things were getting really tense. You don’t insult someone for what they created, as if you could simply recreate Dana White. Impossible. Think about what Lorenzo put into this—the heart and soul that they put into it.

The meeting ends, and I call him and say, “What are you doing?” It was as if what we were asking for were easy, as if we were duplicating it. It’s a sport. It was their highest-rated show.

I represented WWE. We had moved it back to USA after that. It was when the lawsuit with Barry Diller happened that we got it out of USA. He wasn’t angry, but he was seething. I know how Dana boils. It’s like, “Oh, you want to get competitive with me in a sport I know and in what we’ve done? Do you think someone can replace me?”

That was offensive. This guy had no idea what it was. I couldn’t start anything. He destroyed that company. He destroyed it. He let go of everything of value, only bought bad stocks, and then bought them back from, I think, $80 down. He earned a lot of money.

We had just closed the deal with Fox—an incredible deal at the time. The funny thing is that after we made the deal with Fox, and that deal was getting closer, the world—which is in the book—exploded.

We thought Fox had to make the deal because they owned these things: the regional sports networks, the local station group, and so on. Given how much weight the UFC had in it and what it was doing for the network, they had to make the deal. Rupert then sells that business to Disney. There was no economic need. They were on hold until that deal was finalized.

President Trump halts the AT&T deal, so that disappeared. Comcast didn’t want it. They had all the sports they wanted.

Now, this is after you bought the UFC. This is about 4 years after we moved the UFC. Let’s give some context. You hired Dana, but then you and Egon Durban bought the UFC for $4.2 billion. Everyone tells you, “These guys are complete idiots. They don’t know what they’re doing. They overpaid.” Then, in the book, you talk about the story of trying to sell the rights after the Fox deal.

1. Meeting Egon Durban and buying IMG

We bought IMG for $2.4 billion. $2.4 billion.

The thing is, I love puzzles, and my phone is a way of putting the pieces together. I’m going to back up a lot, if you don’t mind.

I started this company, Raine, with Joe Ravitch and Jeff Sine, this commercial bank. I was raising money for them. I flew to Abu Dhabi and got $100 million from my friends in the UAE. I was reading an article by Marc Andreessen. This was a long time ago.

He comes to see me. It was simply about creating serendipity. What you do in your life—and people who are successful, I think they do it—is develop relationships and discover how they fit into your life in a good way.

At that first meeting, I asked him what he did and whether he would put money into Raine. We were raising funds at the commercial bank. He says, “I will. I’ll do it with this guy, Egon Durban, and Nikesh Arora, who was working at Google back then. They’re in Palo Alto now. We’ll be recording with Nikesh next month.”

It’s fantastic.

Yes. Through that, I met Egon Durban. He had bought a company that then sold to Microsoft for Skype—I don’t know who bought it. That was one of his first big businesses. In that conversation, he realized the value of content on a distribution platform. We were talking about creating animation, and he was really creative. We moved on to lunches and dinners.

Ted Forstmann had bought IMG at that time. Shortly after buying IMG, Forstmann became ill, was dying, and passed away from a brain tumor. Awful.

Egon flies down and says, “Can I have lunch with you?” We had a great relationship thanks to the presentation I gave him. He says, “I want to buy a part of you, and I want to go after IMG.”

I was trying to raise money around him. Mike Batista flew to Brazil. Martin Sorrell at WPP. I was trying to put the pieces together to raise the money. I thought it was going to be around $2 billion.

He says, “I want to do this, and I want to go after them.”

I told him, “They’re a private equity firm. There’s no way they can solve this.”

He says, “Give me your numbers. Give me 3 weeks. I’ll be back.”

And now we have William Morris. That’s a completely different story.

So Patrick and I met with him. He brought his team. We explained our economics, TV packaging, and everything we did. Three weeks later, he returned and made me an offer that we could have signed as is. We closed the deal after a while. I couldn’t not negotiate, could I? It’s my nature. Then we went after IMG.

We gained a global presence in U.S. sports. We had movies, television, music, theater, and books—exactly what we wanted. Then we added events, sports, production, and licensing. It was part of Egon’s vision.

Incredible.

I mean, we had the idea, too. We were just trying to find the money and the perfect partner. In the long run, he cares about what you do. When he gets involved in the company, he learns all about it and contributes amazing ideas. He’s an incredible investor and an incredible partner.

Once we had that, Brent Richards, Mark Shapiro, and I went to him and said, “This is the representation business. In addition to that, since we have all the necessary pieces, we negotiate with all the networks globally for sports, film, and television rights. We should add a portion of ownership—something we own in sports—because that’s the direction the world is heading with Netflix and so on.”

Where did you think the world was headed?

I knew they had a subscription business, where you buy a subscription to Netflix or Hulu. That’s how it started. They were eventually going to switch to the AVOD model, which is based on advertising. One of the things that kept people interested was sports. So we needed to own it. We needed to be in the sports space.

2. Betting $4.2 billion on the UFC

I don’t know if it was a year or 2 later, but Frank and Lorenzo had been toying with the idea of selling the business. About 2 years later, they came back and sold it. We found out and started to get involved.

This is where you call Lorenzo in the book and tell him to at least give you a chance before selling to someone else. But you said he didn’t want to commit.

I didn’t want to say anything. I didn’t want to.

Lorenzo and Frank Fertitta are incredible negotiators—the calmest guys of all time. They’re hard. But what you said to them before we got to that point, I love your line. You told them, “Okay, before you hang up, just close your eyes. With your eyes closed, tell me what incredible number would make you happy. What number do you see when your eyes are closed?”

He says, “That’s a fucking huge number, Ari.”

“And it starts with a 4.”

Exactly. That’s right. The thing is, I just needed to set the framework.

Yes. Right. Were you surprised when he said it started with a 4?

No, because I had been involved with the company for 20 years. I knew where the network business was. I knew how much Fox needed it. I didn’t know what was going to happen. In my mind, I did calculations about how high the licensing fees would get.

I asked Egon if we were going to get to this point, and we started working out our figures for what we needed to achieve. We were in that negotiation, and our biggest competitor was the Chinese, actually.

I thought it would be Warner Bros. and Jeff Bewkes. I think a lot of people at TNT wanted it, but Egon said, “No, it’s Fox,” because he was already at Fox and it was an easy transaction.

I wasn’t thinking about Fox, but I did think TNT might possibly do it. However, Jeff Bewkes was downsizing the company to sell it, so he didn’t want to do that at that time.

We went into it, and at one point I think Dana addressed them and said, “Please, he’s had an amazing relationship with me for 20 years. I wanted to be with someone who knew the business and loved it,” and he knew I did.

So we got it a little cheaper than they would have paid, but at the time it was $4.2 billion.

3. Why you won’t remember the extra $400 million

The hardest thing for Egon and me at that point—and this is where I learned, because he taught me everything—was Brexit. The whole banking system collapsed. The great thing about him is that he held firm as much as he could because he believed in where distribution was going and in the value of sports.

We put it all together with Michael Dell doing the preferred shares. I learned so much about private equity. He took me by the hand and guided me through this whole process. It was incredible. It was just brutal.

Let’s move on to when I got sick.

I actually got physically ill because there was so much stress. We had clients involved in this. We put all our chips on the table: $4.2 billion. People were saying that it was the most expensive deal in sports history. We were crazy to get this deal done.

Egon invested money separately in KKR. Henry Kravis and George Roberts, the founders of KKR, were incredible in backing Egon and me in this situation. Then the world explodes. Rupert sells to Disney.

AT&T—and I thought I had a backup deal in case they didn’t pay what we wanted at Fox, that AT&T would. Now we’re talking about TV rights after the deal, after the deal closes, and there’s nowhere to go. There’s no one to sell it to because Netflix wasn’t in sports. Nobody else had really gotten to that level.

We almost got a deal with Jeff Bezos and Amazon. That was like $260 million or something. Then they pulled out. We had been negotiating for 4 months, and they said, “Oh, it has to go through this committee.” It’s not a big deal; it’s just a formality. This was on a Saturday. We had our fight in Boston, and Monday comes around at 1:40. I freaked out.

Did you go with Jeff?

I think so. Jeff was at one of our parties. Lauren Sánchez, his wife now, said, “Come meet Jeff.” I told her, “He took money out of your pocket, man. He didn’t—you’re not feeding your kids. This is what happened.” It’s a big gamble. He didn’t know anything about it.

Jeff Blackburn. This is my conclusion, and I think I’m absolutely right: They just made a bad estimate. The people under him were above the key. Even though Jeff Bezos realized that all the facts we told him were true, he wasn’t going to go over his team. I understood that as a leader.

So what were they trying to do?

They were just trying to save $120 million. They started doing calculations about our fight nights and our pay-per-views. I don’t know what happened.

We have nothing. We’re pitching the project to ESPN. Kevin Mayer is there, along with John Skipper, and we’re pitching the idea. Fox is now official. No. Mark Shapiro tells me, “You’re lying to yourself. You’re not listening to them. They’ve already rejected it,” and I’m pouring my heart and soul into the pitch.

We pitched to Disney. John Skipper was just stalling because we had so many clients booked, like voice actors and rights. We sold them through IMG, but he didn’t like the UFC.

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It’s still crazy that people think they didn’t like it. They used to call it “human cockfighting” when Dana and the Fertitta brothers bought it. Even to this day, that was John McCain.

Yeah. Yeah.

But that was like 20 or 16 years ago—16 years before where we are in the story, more or less. Even then, it was like, “No, this is a—”

4. Getting the ESPN deal done

“Dirty business.” It was like, you know, and he’s stalling. He’s getting into trouble. Let’s not get into his trouble. It’s in the book.

It’s in the book. He’s getting into trouble. He’s out. Kevin Mayer takes his place. They go straight to the consumer. He calls us. We want the deal.

The first offer was crap. Mark and I worked on it one weekend, and Kevin and I have known each other for a long time. We worked on a letter and sent him what we thought it was worth and why we thought it was worth that. Then they didn’t quite get to where we wanted, and we were negotiating back and forth. He says things; we give him things. Back and forth.

We kept pitching the project to other places. We went in to see Bob Bakish, who’s now at Viacom, and we pitched him our idea: “Let’s reinvent Spike, where we originally started, and turn it into a sports channel.”

Exactly what AT&T wanted to do with TNT.

That was the conversation with AT&T if they’d been able to close that deal. We presented the proposal. I was there, Mark Shapiro was there, and Bob Bakish was there.

I got a WhatsApp message from Kevin Mayer saying the price we wanted. They had a deal: $300 million. I swiped the phone to Shapiro while he was presenting his proposal with all his heart. I was presenting my proposal with all my heart. He looked down, but he kept presenting his proposal. I thought, “The meeting was over. We had to go.”

Why not show it to these guys? Did they want to match it?

Yes. We got in the car because I had the deal I wanted, which was an incredible deal. It came down to the number we had in our pro forma report. We had 4 months left before this turned into a nightmare.

They were on the plane—Bob Iger, Kevin, and us—negotiating. We were going back and forth and negotiating the terms over WhatsApp. It was 8 episodes on ESPN, with the rest behind the paywall on ESPN+. They were launching ESPN+, and so on.

We jump to when we got back to the office. We called Dana. We were all sweating bullets, which was kind of unhealthy, and we said, “It’s 8 episodes.” Dana says, “No, I won’t do that.”

I love him so much. He’s pushed me so hard and made me better. I said, “What are you talking about?” He replies, “I won’t do it unless we have 10.” I said, “We don’t have anyone else right now.” He says, “I don’t care.” I said, “What are you talking about?”

We got to the point where I had no play. No play. I put Kevin on the phone, and I freaked out on him.

This happens several times in the book, where you think, “Okay, I’m just going to freak out.” So explain to people who haven’t read the book yet what it means to freak out.

I said, “Damn, I need 10 freaking episodes. I can’t do this. You have to create stars. You’re going to want stars. You need stars to put behind the paywall so people will buy it. You need it on ESPN so they understand the sport.”

I just told him this whole story, which was actually true. Mark Shapiro—I think he went as pale as this chair, right? I said—and he said, “We don’t have anything.”

I said, “What are you doing?” He said, “Calm down. They’re not going to screw this deal. They want the deal. We’re going to make a move. If we can’t get it, we’ll call Dana. We’ll work it out.”

Cut to Kevin. To Bob Iger’s credit, he started in boxing, and he actually loves combat sports.

Bob Iger—was it ABC? Where was he working?

Boxing. It was ABC.

Yeah.

A long time ago.

Yeah.

Without Mark and me knowing it at the time, Bob told us later that he told Jimmy Pitaro, who was on the plane too, “Just give them the 10. Work it out on the calendar.”

I didn’t know that. Kevin calls back: “We got the 10.” Dana’s happy. Boom, we’re off at full steam. Luckily, Skipper got into trouble. But then we came in.

Wait. I was going to say we’re not quite off at full steam yet, because then you say, “What about this nice present?”

Then we go to the celebration with Kevin and Bob, who were incredible partners. Fantastic. They’ve been incredible partners. They’re incredible.

Oh, no. You go to a celebration to give away something used.

Give away?

Yes. It’s an episode of Seinfeld—Larry David, the regift—and we bring it. It weighs 77 or 100 pounds, and we’re bringing the book.

Wait, the funniest part: It’s this UFC commemorative book that I think Dana gave you, and you guys are on the phone making sure that—I mean, it’s like 3 by 3 feet, with some poor assistant saying, “Make sure Dana didn’t put ‘With love’ on it.”

Exactly. Cut to us sweating bullets while they check the book. It wasn’t there. In 2 seconds, the assistant did a good job. We’re in the meeting. It’s a big meeting, and I’m like, “Fuck off, right? What? You’re going to make Mark and me go sell our pay-per-views while you guys put some behind the paywall? You guys are sons of bitches like that.”

“Bob, I didn’t know. Kevin, did you know we could buy the pay-per-views, too?” Kevin’s a really smart guy, but it took some effort to get everyone over the hurdle. He’s like, “Honey, you’re unbelievable.” He’s like, “We’ll get back to you on Monday.”

Monday comes, and they buy the pay-per-views. Unbelievable. A 7-year deal. Unbelievable. They did unbelievably well with that. We did unbelievably well with that. It was a home run for both of us.

But this is why I wanted to start with the story, because everyone’s saying these guys are idiots. They’re paying—overpaying—to buy UFC. The valuation of this one deal is almost—I think the 7-year deal was almost $4 billion, almost the purchase price of UFC. So, the first deal, right?

Well, it wasn’t a— It kind of signaled where direct-to-consumer was going. It was good. That’s it. Everything that Mark Shapiro, myself, and Egon Durban had thought was happening was happening. We just had to get through some consolidation and deal flow to get there.

The second part of the deal, where they buy the pay-per-views, that’s in a few days.

How long was it from the first time you contacted them until the first deal closed? Was it 2 years?

No. We were getting to the end. We were putting Fox off because we thought they were definitely on the table. We just wanted to see what else was going on. Then, to Iger’s credit, he went for Fox, understandably, for direct-to-consumer and what he wanted Disney+ and Hulu to be. He came in. Fox was there early on, but then they sold.

From the beginning of the conversation to the end, it was 3½ months, I think, with Disney and ESPN.

Most of the deals you’ve made—can we go back to when you were just an agent, or talk about buying all these businesses with Egon? Is that normal? Is there usually that much?

Well, no. I mean, if you’re closing a deal with writers on television, which is what I started my business with, and you’re staffing a show, back when the upfronts used to be, you’d go to New York, you’d be at the upfronts, like May 28, until you had the staff in. It was a 3-week race to get as many writers as possible onto TV shows that had been contracted by the networks.

5. Taking over William Morris

The UFC deal and the IMG deal were probably 6 months to a year each. And then the merger.

There was a merger that took that long?

Yeah. In 2003, they laughed at you, like, “Are you going to buy us?”

That was one of my favorite parts of the book, where you go talk to the Harvard professor and they tell you there’s no such thing as a merger.

That’s a lie. There’s only one company. Professor Nitin Nohria—amazing. In fact, I think he’s in the board meeting with Josh Kushner at Thrive Capital. Thrive just reached out to see if I want to talk to him. Do you think it would be interesting to do that?

But I love what he told you. He says there’s no such thing as a merger. I mean, there’s an alpha, a beta, a conqueror, and a conquered.

You actually mentioned Egon Durban. Michael Dell has been a huge influence on me. He’s become a friend. I just had dinner with him about 2 weeks ago. I met this guy named Hock Tan at one of the Dell events.

Hock Tan, the CEO of Broadcom. He said something really funny because he’s made a lot of acquisitions, and he was giving some advice to another tech founder there. He says, “Here’s my most important piece of advice for you.” He says, “When you’re acquiring somebody, make sure they know from day one—you know, Hock Tan has a very intense personality.” And he says, “Make sure they understand from day one that you’re the conqueror and they are the conquered.”

Yes.

And in your book, I love this scene you take us to, where it’s 2003, in a private dining room in a restaurant. They’re laughing in your face that you’re going to buy them, saying, “We’re a 100-year-old company,” or whatever. And then that deal takes about 4 years.

In those 4 years, Patrick and I were stealing clients, weakening them. We were stealing agents, weakening them, and just listening to what was being said on the street—that there were problems there. A lot of dissension.

Then the moment came. I so botched the first meeting, and Patrick was perfect in that first meeting, where I just freaked out. Frenzy doesn’t always work.

No, no.

That delayed the merger by 4 years. I played a horrible game of chess there. Just horrible.

I was at a Jewish holiday, at a fast-breaking event, and one of their top agents came up to me and said, “It’s time to pick this up again.” I met with him. I met with this woman, Jennifer Rudolph Walsh, who was running their book division, and we revived it. Then it moved pretty quickly. It was about 6 months because we realized they needed it, and there was really a lot of disruption happening in there. A lot of dissent. That dissent allowed Patrick and me to be the conquerors in that situation.

Then Egon coming into our company allowed Patrick and me to financially incentivize everyone and take control.

Before we go back to the Egon part, I think this was very fascinating because I didn’t understand what was going on with the book, and then you shut this down and closed the door to William Morris.

Yes, we’re talking about the merger. I’m sorry.

And you, at this point, said that you ruined the first meeting in 2003, and then you—

“Ruined” is—be nice, be gentle. That was a kind statement.

Okay. But you see, you learned a couple of years later, because then—I forgot the guy’s name—he was like, “Oh, I want to be president. I want this, or I want to choose the others.” And you were just like, “Yeah, right, right, right.”

This is what happened. The deal closes, meaning William Morris votes in favor and Endeavor votes in favor. It would be a merger, right? Which doesn’t exist anymore, right? Patrick and I had been constantly talking to Nitin, who helped us analyze it. Even at closing, a lot of their core members who were shareholders were calling us and saying this wasn’t going to work.

We got to the point where the deals were approved but not closed, and we realized we couldn’t move forward, mainly on their side. First, there were guys who made a ton of money: Peter Grosslight and his music department, one of the biggest divisions, and Mark Itkin in his unscripted business. He’s not on the board; they don’t really pay attention to him. We had to retain them for the merger to work.

I was going to have separate meetings with both of them and involve them in the plan because they hated the idea.

And did you tell them the plans? You already knew?

We had brought them to our side of the fence.

How long were you planning before you carried this out?

This is where Patrick was great. I was really nervous about this. I was like, “This is going to be a nightmare if he’s sitting there.” He had sent a memo: “I have to be on every call with the studio heads.”

I didn’t even understand what that meant. I mean, I’m on a call with a studio head. I’ve run this company with Patrick for years, and you want to be on my call? Like, no. I realized that Patrick said we’d probably go in after 2003. That’s 4 years later—we’re going all in.

I got really scared. Patrick, in the conference room on the third floor—not physically, but he slapped me and said, “What? Don’t you think you can pull this guy off?” That woke me up like a cold shower, and we got down to it.

Then everyone realized on their side that Jim couldn’t be part of this. We negotiated very clear terms of majorities, supermajorities, and what happens with the board. They had 5 votes. We had 4 votes, and a quarter for each of us.

Jennifer Walsh and Patrick went to Jim Wiatt’s lawyer and said, “It won’t work.” It was 2008 or 2009. The world was ending. We don’t remember, but the world was ending. My brother was in the White House, there was a financial crisis, almost a depression, and nobody thought at that time that we were going to write a check for $24 million to buy a guy.

Buy a guy.

You have to buy another one, too.

Yes.

So, he agrees to the deal. He takes the $24 million. They convince him. He says yes. Check signed.

Irv Weitz thinks he’ll get the job once Jimmy leaves, and I call him. Patrick is on the phone. I said, “You don’t have the votes because you need two-thirds, and you don’t have two-thirds. The board doesn’t want you.” It was a little complicated. I won’t go into details, but he finally realized it wasn’t going to work. We wrote him a check for $20 million.

So, we lost $44 million in 2009.

We lost a lawsuit over the building they bought because we were going to have to share the parking garage with our direct competitor, an agency right there. Who the hell would do that?

I don’t know. And then there was another $35 million, so now we’re at $75 million.

Yeah. No, that’s $80 million. Then we had to pay bonuses between $20 million and $40 million. We were screwed.

And, you know, getting a loan from a bank in mid-2008 or 2009—I mean, that’s when Russell Goldsmith, who was part of City National, always had our backs when we needed a million dollars unsecured.

6. Starting Endeavor with a table and a phone

When you left ICM and started Endeavor, let’s talk about that quickly.

When we left ICM, yeah, the 4 of us—

And you started Endeavor.

Endeavor. So, it was Tom Strickler, Rick Rosen, David Greenblatt, and me. Your description of this startup that’s now worth a ton of money—I love it. It says, “Four demons in a room making calls.”

They had a table and a phone, and we couldn’t collect the commission. We put it in escrow because we were being sued by ICM for whatever reason. They thought we’d created a horrible situation. All the press around us made the company even bigger than it actually was.

And then this guy at the bank, whose name was Russell Goldsmith.

Yeah.

He’s the one who backed you with $1 million when you had nothing.

Now we had no money. None of us had any money.

He was amazing. Then, cut to 15 or 19 years later, whatever, and I said to him, “Listen, this dream is going to be over if you don’t do it.” And he did. What happened after that, as I recall, is that we bought IMG. I said to him at the time, “I know how we’re going to pay you, but we’ll pay you eventually.”

He was trying to sell City National and make a deal with the Canadian company, and he said, “Can I have some of your bonds?” This was the $2.4 billion deal. Egon had asked for his relationship; that was his specialty. I told him, “Let me tell you the story. I need $300 million on your credit.” He sorted it out. Egon did, and we gave Russell exactly what he needed and paid him exactly what he needed to convince him of the deal he was making.

And yes, I like how you put this, because I was thinking, “These guys are idiots.” They spent $44 million just on acquisitions—no, we spent $44 million to essentially acquire something that was 100 years old, with a huge list. It’s like we stole it from them. It was incredible. It was the best deal Patrick and I ever made. Nothing even comes close.

The great thing about when we did the IMG deal is that it was very tense while we were doing it. This is the great thing you only learn over time. I have young kids—two 30-year-olds, one 27-year-old, and one 24-year-old, one daughter and three sons—and they have ADHD like I do. I think all kids, when you’re young, just want to get started. The only way you learn is through failure and success, and you have to go through things.

We were in the IMG deal, trying to make it happen, and it was us against Peter Turner. Peter Turner was bidding for it. We were bidding for it, and they didn’t want us. They definitely didn’t want us. They wanted him. I swear to God, what the hell do I care? I learned so much from this.

I think Turner’s offer was $1.9 billion. We offered $2.3 billion or $2.4 billion. This was Egon, right? Egon goes and says, “You’re not going to remember this $400 million. You’re never going to remember it. Let’s make an offer they can’t keep beating. Let’s just take it off the table in one fell swoop.” A fucking genius. Just incredible. I haven’t made these deals. He’s made a million of them.

We did it. We got the deal. Shapiro told me before, “They don’t want you.” I said, “The more heroes, the better.” They may not want us, but this was Egon’s move, and it was perfect.

We had a big fight, and that’s the crazy thing about deals: You only learn about them afterward. We thought we couldn’t do it, that this deal wouldn’t be successful, because we were trying to secure the guys from the college who were running the college side—George Pyne and the head of the college business. They had all that college business within IMG at that time, the American company, and it was quite a heated discussion about how, if we couldn’t get those executives, we couldn’t do the deal because the college business was so important.

Not that the college business was going to fail, but ultimately, the college business wasn’t worth anything within the IMG business. It was all about the international business and everything we’ve done since then. Again, that’s why all the planning is involved in making a deal. Who knew Fox was going to sell? All this says you just have to constantly work at things. If you don’t work, there will be huge mountains you have to climb and huge failures, but if you believe in the strategy, you can overcome it.

This is what you were saying. We had this incredible conversation before we started recording, and I said, “We have to sit down and record some of this, because this conversation is blowing my mind.” You mentioned earlier the advice you gave to the CEO of one of your companies now, and it was very similar.

7. Stop telling yourself stories

Because you can only do what’s in front of you, man. Stop telling yourself a story. Brené Brown says, “Stop telling yourself a story.”

Right. That’s in her books, and one of the great things she—

Who is she?

Brené Brown.

Okay, she has great books. We all do it. We tell ourselves stories in our heads that we then believe, and those aren’t real stories. They’re just stories. They’re not reality.

My CFO of this new company—we started this events business called MARI—comes up to me, and we’re going through the fundraising. We have to do the fundraising, the fundraising, and it’s getting really traumatic. We’re not going to make it, and I said, “Stop. All we have to do is keep making the calls. We’re going to make it. We have a really good product, a really good story. We’re building a great company. The world is on our side. The thesis is correct.”

He says, “Take a deep breath.” He says, “You’re right.” I said, “Let’s keep making the calls, doing our thing, and telling our story.” People will come to us. This story only gets better.

I try every day of my life—and one of the things I say in the book is not to listen to that voice. We all have that voice. We feel guilty about things. We can’t spend enough time with our kids. Is this right? It’s really not worth it. That voice always wants to get negative or tell you something else.

That’s one of the most interesting parts of the book, really—the transformation you see. The first word, the first sentence of the book, is just one word, and it’s “anger.” Then you see this profound change, and the book ends in a very different way, which is what I want to get to before we move on.

I want to go back to what Egon said. He says you won’t remember the $400 million, which is one of the craziest lines in the book because it’s true. What investment bank or what private equity fund would ever say that? That’s why it’s incredible. Nobody says that. They say, “If that guy offered $1.9 billion, let’s bid $2 billion.”

He sees a map that’s very different from everyone else’s in the game about where he wants to go. Here’s the important part: I always say learning isn’t memorizing information. Learning is changing your behavior, right? You didn’t just memorize it. You changed your behavior, because I think it was the UFC deal, or another deal you were working on, and someone inside your own buying team said, “No, no, let’s lower this.” I don’t remember which deal it was.

You said, “Absolutely not.” You quoted Egon, and you ended up getting the deal. Then he says, “You won’t remember saving whatever.” Let’s say it’s $2 million. I remember it was $200 million—$100 million. But you’ll remember the screw-up you made by losing it. You’ll remember the screw-up. You didn’t say “lose”; you said “screw up the deal.”

Yeah, let’s stick with what’s given. You’re going to have to work really hard. Even if it’s the best strategy, even if you’re right about everything, there will be some really tough roads. That’s just called business. Life.

If you commit to working like crazy and overcoming all the difficulties, and you want the deal and believe in the strategy, the $100 million, the $200 million, the $150 million—that’s not the game. The game is that we’re going to have to work really hard. There are going to be some failures. There are going to be things that we think aren’t right, and things that we thought weren’t right that turn out to be even more right. Let’s just keep going.

When Disney bought Capital Cities, maybe I’m wrong about the story, but I think I’m right. I think they valued ESPN at zero. It was the most valuable asset. When Tom Werner and his partner, whom I introduced to Joe Ravitch at Goldman because they had made the YES deal for the Yankees, were buying the Red Sox, I think at that time they had the cable portion of that deal valued at $75 million. It was the most important thing. It’s not that the team is good now; at that time, that was the most important asset.

All these things that we think we know and that we work so hard on—you don’t want to go crazy paying $2 billion more than others, but you know you’re going to work hard. There will be things that you project will be wrong, and things that you project will be wrong that will make it even better. You’re just going to have to work through it. That was a great lesson that Egon gave us.

I think something that I don’t even think I fully grasped from the book, although it’s there for me to understand deeply, now talking to you, is this idea that I’m going to be flexible and play the game that’s right in front of me.

8. David Geffen: Get in traffic and get hit

It’s a phrase of David Geffen’s that he told me when we were trying to do the William Morris thing. I should have listened to it a lot earlier. David Geffen—let’s talk about this. Then David Geffen tells me, “Let me get this straight, because you’re kind of losing it.”

I’ve never read a book like this. The amount of honesty is incredible. You share that, yes, I’m very successful, smart, and determined, but I also have my traumas, like all of us. I think we do ourselves a disservice when we try to pretend we’re perfect. We’re all imperfect human beings, and you just say, “This is what it is. Accept it.”

You probably have this, too. We’re trying to grow the business, and you’re terrified because you have this in mind. It’s like, “I don’t feel safe, because if Endeavor isn’t safe, I’m not safe,” right?

He was an incredible adviser to me and a kind of mentor. He told me, “Just merge with William Morris, get in the traffic, and let yourself get run over.” In the end, he was saying to me, “Believe in yourself, believe in your partners, and you’re going to win that battle.” And he was right.

The way I interpret it, too, is that the worst thing you can do in a changing world is stand still.

He says, “Don’t stand still.” That’s like when we were in the conference room and I was so nervous about the merger, and Patrick slaps me in the face—not physically, but emotionally: “Don’t you think we can win this battle? They’re people just like us. Our culture is better. We’re going to win.”

That was like a bucket of cold water in my face, and he was right. The worst thing you can do in a changing world is stand still.

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I want to get back to Geffen. I just flew back. We have a mutual friend, Jimmy Iovine, right? The crazy story is, I was in England with Jimmy. We were doing an event together, and I was interviewing him onstage. Then he says, “Hey, come back with me.”

So I flew with him on his plane from England to Los Angeles. We’re on the plane, sitting next to each other. He pulls out a book, and I pull out a book. It’s the same book.

Then I said, “Dude, what do you think?” I asked him, “Do you know Ari?” He started telling me story after story about you.

That’s another guy I called out of the blue. I had read about him. It’s my favorite phrase: I like to create serendipity. You read about someone, and you call them. I did the same thing with Michael Rapino, one of the greatest executives of all time.

The company was worth $200 million. I read about it in The Wall Street Journal. I was on vacation, came back, and gave it to my sister. I said, “Get me this guy on the phone.” This was 25 years ago. We met and became great friends quickly. He put me on the board.

We’re going to talk about this because you call it, I think, the Ari—not Ari Gold, but the Ari manual—the entrepreneurship school you created for yourself, which I thought was one of the best ideas in the book.

But I want to tell you, there are 2 things Jimmy told me that I have to ask you about. I said, “Is Ari really like that?” He said, “If he needs anything from me, he’ll call me 16 times in a row.” I want to talk about whether that actually works, because I find it shocking.

We talked about Geffen because Jimmy says David Geffen gave him some of the best advice ever. He just said, “Hey, you and I do pretty much the same job. You just won $500 million. I do the same thing, but I earn much less. I’m thinking of starting my own record label.”

David Geffen said, “You absolutely have to do it.” Jimmy asked, “Why?” He said, “Because there are a lot more people dumber than you who own record companies.”

Listen, he’s one of the great advisors in our business. He has a sober view of the business and gets straight to the point in 1 or 2 sentences.

Jimmy told me this because he still goes to David for advice. He says, “David will tell you the fastest way from here to there.”

Jimmy’s point was simply that you can’t always get there emotionally.

No, because it’s your business. You overcomplicate things in your head.

That’s why you go to David. The voice is still there.

Yeah, you say, “Oh, I have this big problem,” and he says, “Fire that guy, buy that company, marry that girl.” He just says, “There’s 1 thing.” It’s not those 8 or 10 things. It’s that 1 thing, and you just do that.

He did it with you. He says, “Just buy, merge with an agency. Don’t stand still.” I don’t know how he learned to do that. He doesn’t listen to that voice in his head. He just sees it, does it, and you can always count on him.

You lay out the situation to him. 2 seconds later, you hang up the phone, and it probably took me years, but he was right. Just get 1 of those companies. I think we got the right company, but he was right. Just get in the traffic, get hit, and you’ll work harder than anyone.

There will be good things, and although he didn’t explicitly say this, there will be bad things, but you’ll survive. You’re good. That’s what he was saying.

A lot of the guests who come on the show ask me afterward, “Hey, can I help you get someone? Who’s at the top of your list?”

David Geffen is toward the top of my list. People tell me, “Oh, that’s never going to happen. He’s too secretive.”

No, he will.

Oh, then maybe I’ll give you an assignment later.

I’ll give him one.

9. Why Ari rolls the calls

Yes. Obviously, I knew who you were from the character on Entourage. When I heard you were writing a book, I was like, “Roll the Calls?” I didn’t even know what that meant.

So explain why you called the book Roll the Calls.

When I walk into the office and go down the hall to my office, I start yelling to my assistant, “Roll the calls. You know, the people who’ve called me. I want the people.” They just start connecting the calls.

My whole life, like I just said, is how I met Marc Andreessen, which led to Egon Durban, which then led to this, that, and the other thing. It’s a puzzle, and the way I go into the puzzle is through the phone and then by meeting people.

After I read something, I call somebody. You meet someone, and they have, in a good way, created serendipity in my life. I’ve created a world like that.

Passing calls is how I do it. When I get in my car and I’m on the phone, I call my office, have the calls passed, and we just keep passing calls.

I just heard you doing this when you were in the bathroom.

Yeah. Come on, let’s pass the calls. I don’t know where this is going to lead.

Hopefully, if I’m good at my job—and I think this is the great thing about being an agent—what it’s taught me in business is that creating a TV show or a movie that you put together is creating a puzzle.

As great as Martin Scorsese, Jonah Hill, Aaron Sorkin, Seth MacFarlane, and Tyler Perry are—my client list is full of incredible artists—the job as an agent in the entertainment business is that you have to be an incredible businessman, with new ideas for them in their deals and for how to put a movie together and overcome conflicts, because there are always conflicts.

I’ve taken that skill set, through great teachers like Egon and others, and simply by observing people. I call others when I’m in situations. I can take that same skill set and apply it to our businesses.

That’s how I live my life: passing calls, doing my thing, David Geffen, stuck in traffic, taking hits, and not being afraid of having been afraid.

I used to be emotionally scared. My partners have helped me with that. I thought, “Is it because I’m dyslexic? Am I smart enough to do this?” Now I don’t have that fear anymore. I can overcome these deals and be creative.

I observe what Egon does. I look at what Michael Dell does. They are incredible artists at how they run a company and how they build a company. I think it’s a great art form.

Michael Dell has a net worth of, I don’t know, like a quarter of a billion dollars, and I’m telling you, he’s still very underrated. It’s incredible.

It’s exactly like that. It’s funny that you use the word “puzzle,” because that’s what I ask him about, and that’s how he views business: like a giant jigsaw puzzle.

It’s incredible. The guy started his company at 19 with $1,000 in his bedroom. He’s in his 60s now. Look at what he’s doing today. It’s a monster.

But it’s also incredibly user-friendly. I’ve spent hours with him. There’s no reason for him to spend hours with me teaching me things, but he does. Although I assure you, he learns something, too. He’s an extraordinary human being.

Those people you admire, like Marc Andreessen, are artists at what they do. This is what I don’t like about the world right now. For some reason, a certain segment of the population thinks that what these great entrepreneurs have done is horrible.

They think it’s wrong that they’ve created great wealth for people and great wealth for the country—that they’ve created something great—and that somehow it’s not good. I love capitalism. I think it’s incredible.

I’m the son of a Cuban immigrant. I tell this story over and over again, and it’s not a joke. I grew up in South Florida. I literally remember being 9 years old and meeting people who came here on rafts.

How many people go to the southern tip of Florida and put their 4 kids, when they’re little, on a raft from Cuba? That’s a one-way trip. They’re coming this way. Why? Why is that happening? What’s going on?

10. Building your own school of entrepreneurship

I instinctively knew this is a very, very special place. I want to learn from these people.

So let me move on to the next question I have for you. Tell me about this Ari Emanuel School of Entrepreneurship. When did you come up with the idea, and how long have you been doing it?

It just started as 1 of the first ideas about it.

My boss at InterTalent was Bill Block, who ran the company. He was a very curious guy, and he read George Gilder’s *Life After Television*. We still talk about it all the time. It’s still there.

I read the book back then, I think in 1992. It was a very short book, thank God, because I’m very dyslexic. I called George. I don’t know how this happened in my life—I read an article, called the guy, and people answered—but it just happens to me. As you know, if people don’t call me back, I call and call and call until they call me back. Sometimes people think it’s harassment. If you use some lightness, humor, and self-deprecation, you get away with it and don’t end up in jail.

He started talking to me about the business, and that led me to realize that when we started the business in 1995, there was going to be more television. It was about how distribution was going to change: the same number of people making content, maybe some new content—which now includes podcasts, social media, micro-dramas, and so on—and content creators becoming more valuable. That premise was all I needed to start the company with my 3 other partners, who believed the same thing.

That just continued my relationship with Michael Rapino, one of the greatest executives of all time. He grew a company from $200 million to $40 or $50 billion. I don’t know what he’s done; it’s incredible. Marc Andreessen—I mean, that’s my life. That’s how I live my life, and those are the puzzles I create. The great thing about it is that I can always go back to them and call them if something comes up, invite them to lunch, and listen to them.

11. Learning from Elon Musk and betting on live events

That’s how I met Elon Musk. I read about him when he was starting a car company. I didn’t know the guy, but I called him. We met, and we have an amazing relationship. Like in most friendships, I don’t agree with him all the time. I do agree with him, and I learn so much. I disagree so much. That’s life.

What have you learned from Elon?

He predicted early on where AI was going. He was talking about AI in 2007 and what it was going to become. Then he made me see that live sports were going to be important. Definitely, sports were going to be important. We talked about that, Elon, too, and then he said that the one thing that can’t be disintermediated by AI is live entertainment.

He didn’t talk about anything else because I was asking about entertainment, but that’s what he brought up. That was the idea behind MARI, and we’re building quite a big business in that area.

How does MARI relate to TKO?

Separate companies.

Separate companies, but they’re doing similar things.

Yes. One is purely sports.

Yes.

The other is live events, from art to car auctions, holiday events, and tennis events. It’s just live events. Michael Rapino is just in music.

Okay. TKO is just sports, right?

It’s a live sports business, you know, and MARI is an events business. There are some sports assets. We have the Miami Open and the Madrid Open in tennis. We have participatory sports, like Escape from Alcatraz. We have a collectibles business at Frieze and Barrett-Jackson, and this thing called Collect-A-Con, which is in the Pokémon space. It’s all live events globally.

How do you divide your time? Are these the 2 main companies that you dedicate almost 100% of your time to?

These are the 2 companies.

Okay. And what’s the split right now? One is obviously huge and growing, but this one is totally new.

Time is a crazy thing, like you said. I spend a lot of time on both. I just work.

Okay.

I have my clients. I still take care of my clients because it’s important for TKO and everything else. I’ve been doing all the work around MARI. That’s what I’ve been doing, anyway, along with TKO.

12. Learning from Hollywood’s greatest agents

Okay. I want to go back to the beginning of the book, to the very beginning of your career—basically, the start of your new life, right? That led you down the path to where you are today. You can trace it back to when you were 24. You see this job ad: “I’m going to be a talent agent’s assistant.” You didn’t even know what a talent agent was.

Well, sort of. This guy Mike Mendelsohn told me—I landed in New York, and a friend of a friend told me what William Morris was. I’m from the Midwest. I didn’t know. I had no idea what an agent was. I didn’t even know they existed. For some reason, I thought I’d be good at it. I could do it.

There are a handful of things I pulled from that section of the book that I think are really important, that you’ve used your whole life and continue to build upon. Robbie had the same kind of apprenticeship school, but he did it through dictation and writing letters from great minds, and they maintained this discourse. I was like, “Damn, Ari does that later with his phone,” right?

The other thing I found really interesting is that you had someone older and really successful telling you, a young man, “Hey, I can’t serve you anymore. You have incredible talent and determination. Move west and go build your own empire.”

The third most important thing is that you have to listen to their calls. This guy used to be at the top of his game, right? Now you have this younger guy—this is a recurring story—who is younger and hungrier, coming for what you want, and you’re listening to this.

He was the king: Mike Ovitz. Even though he was younger and hungrier, there was Lew Wasserman on Mount Rushmore, and Mike Ovitz on Mount Rushmore. Mike Ovitz created what nobody had created. He created the packaging business and the movie business.

He saw what all these other guys—and there were many, many agencies—didn’t see. He had Ron Meyer and Bill Haber. It was Patrick and me, and Lew Wasserman had Jules Stein. They had a glimpse into what the film and television business could be. Remember, they made a fortune thanks to Bill Haber in the television business.

There’s a parallel here with your own career because people say, “Oh, this UFC thing is kind of dirty. It’s from a lower class or whatever. It can’t be a good business.” You say, “They don’t know what they’re talking about.” They were called the TV guys at CAA. It was a derogatory term, right? And they made the transition.

Yes. But here’s the one thing: I don’t know about you, but I have to go back and listen to your episode with Mike, because this is my conclusion. I have no idea. I really should call Mike about this.

He takes the Coke business, the Coke advertising business. Mike Ovitz was at the very top of the entertainment world. I just didn’t understand why Mike, at that point—because he could have raised any amount of money he wanted—didn’t go and buy Grey Advertising back then. It was a really big agency. I think they handled Coca-Cola, although I could be wrong. Maybe it was McCann, something like that.

It would have changed things and added a new leg to the chair. I don’t know if he just didn’t think about it because he was thinking about a lot of things, or he didn’t want to do it, or he thought the economics wouldn’t be in his favor. But that would have completely changed his business, and as David Geffen said, it would have generated more traffic. You never know what it would have led to, but that’s how I always thought of it. Why didn’t he buy an advertising agency and get more clients? Unless he—I don’t know.

That’s what Patrick and I did, along with Mark Shapiro and Ian. We realized, “No, we want to own an asset.” Maybe we had that in mind when we saw what he did and didn’t follow through on. I think there are 90 reasons why he didn’t, or something must have happened, because he was too smart not to have done it. We concluded that we should do it because of where the world was headed for us at that time.

Going back to that, what were you hearing? What was the difference? You’re on the phone call. You’re with Robbie Lantz. You’re listening to Ovitz, young and hungry. He’s stealing all these clients from your boss. What do you hear on those calls? What were the phone calls that differentiated Robbie from Ovitz at that time?

First, I never heard what he said to clients. His salesmanship, like Ron Meyer’s and Bill Haber’s, was far superior and backed up by everything they did: packaging movies and forcing studios to take them. It was a different time because he had the DVD business and all that.

I can only conclude, because I wasn’t on the calls or at the signing meetings, that they were a packaging machine and that it was going to be profitable. Remember, if I’m not mistaken—and I don’t think I am—Jules Stein and Lew Wasserman were signing people because they had something different. They discovered a tax loophole for clients to save money, and that’s why they signed so many.

Mike had this pitch. Again, I don’t have all the facts, but his ability to package was unprecedented in film and television. It was true. That’s his genius and Ron Meyer’s genius: this whole concept of packaging that they created and the star-driven production business, creating projects so that people weren’t just actors but could also be producers. Nobody had thought of that before. He did it. He really pulled it off, and that’s how he recreated the business.

Yes. The first time I met Marc Andreessen, I asked him because he’s open about saying, “Hey, I designed a16z based on the CIA.” I said, “What do you think Ovitz’s superpower is?”

He replied, “He’s the greatest agent in the world.”

I said, “What does that mean?”

He said, “That means he’s the best salesman in the world.”

And so I'll tell you right now, he's one of the greats as an agent. I worked directly for Bill Haber, and Mike was there, but you can't underestimate Ron Meyer. He was incredible, as flawless as anyone. Whenever you see someone world-class at what they do, their team will be world-class, too.

13. Outgrowing rage without losing ambition

Amazing. It's 100% true. But I needed to get to this crazy transformation because I was looking for your advice. I'm obsessed with people who are decades ahead of me. So, since you know where I'm going with this, I asked, “Hey, what were you doing when you were my age?”

Don't make the mistake I made of not seeing your kids.

We can talk about everything publicly. I'm fine with that. But what I notice about you is that you're a more relaxed version of yourself than I imagined from the book.

Definitely.

I still heard you on the phone, so I thought I was going to get another Ari Gold or something. The book talks about anger, about being a bundle of anxiety, a bundle of fear, about not feeling safe, right? Being angry, getting hit by a damn car and almost dying, and then realizing that this isn't a dress rehearsal. I think that's the most important part—one of the most important things you have to have in your life. When did you decide, “Hey, I have to make this change, because if I keep living life as this uncontrollable bundle of anger, I'm actually going to have an unhappy life?”

There's a character in the book called Dr. K, who's my psychologist. He had this concept called the Ego Project. We all think we can control certain things. You have this thing about your legacy, all those things that are bottled up in the ego. He was trying to break it down and show me that there's your plan and then somebody else's plan. He started with the car, like, “This isn't a dress rehearsal.”

How old were you when you were hit?

32.

Okay, right.

When you're 32, my career is going great, life is great, physically I'm great, and you just realize that it could end like this. That starts a chain reaction in your brain. You have to constantly remind yourself, getting sick with the UFC, “Oh no, you're not invincible. You're human.” You think you can control all of this, and if you play the chess game in your head, you're going to win. When you don't, that's when you get angry.

I kept working on it, realizing it and wanting to improve, and not indulging in the anger all the time. You just get older and you get tired of it.

At what age did you start to get tired of the anger?

Well, this is what I realized: I want to be really successful. I realized that the anger and rage, and the way I was running the business, would never get you to great heights. Why? I wasn't happy with how I was living my life.

One of the things the book does is say, like, J.R., who helped me write the book, reminded me and showed me early on when we were doing this: there were 3 weeks that I couldn't account for. This would happen in these 3 weeks. This would happen this month. How the heck did that happen?

All these things—going to visit my daughter when she was at Montana Academy and up in the Utah mountains, and then coming back, and then this deal happened and that deal happened—it's just crazy. And I wasn't enjoying it, was I? Even though I was getting through it, I wasn't enjoying it.

That just required a process. I saw the toll it took on my marriage. Things get left behind. Now, if you ask my kids, I think my ex-wife and I scored a touchdown with 4 amazing kids. That was great, but I didn't think I could progress the way I wanted, or that the company could do what it does and get to where I wanted to build it, in the state I was in.

Then I went on a journey of meeting people who would help me realize how to become a better person. That required shamans and other means of getting there that were different from Dr. K. They allowed me to realize that the world has existed for 3 billion years. I'm still competitive, but there's a different way of being competitive.

I never realized that going on vacation could be better than not going on vacation. I thought it was a really bad thing for you. Jeff Bezos told me many years ago, “You just have to realize that when you're on the field, be on the field, but it's okay to get off the field. When you're off the field, get off the field and don't play the chess game. Don't be afraid to get off the field.”

It's not a bad thing, because it makes you even more powerful when you're on the field. I never used to get off the field, but with my eyes open and constantly working, plus using 5-MeO and other things that helped me realize all this about legacy—which is nonsense in my mind—or the Ego Project, or whatever other way you want to categorize it, I started to change.

The reason I've been telling all my friends about this book is also because of how brutally honest you are. You're one of the most successful people in the world at what you do. Yet in the book, at the same time that you're the most successful person in your field, you're also trying to fix what's wrong with you—what you feel is wrong inside you—to the point where it makes you better.

You do this 5-day meditation retreat in, I think, India.

India.

And there's this guy you name in the book as the leader. I'm just going to read a few sentences:

“Jennifer Walsh, who helped get rid of Jim Wiatt, recommended this guy to me. So after stabbing someone in the back, you need to go on a 5-day meditation retreat.”

But he says you can't live in a world of war and rage and also in a world of beauty. You have to choose. Do you want to live in a beautiful state?

And then one of the last things he tells you is, “Whatever you do, do it for joy, for the art, or, if not, don't. Then calmly move on.”

Great line. At the time you heard that line, were you in a position where you could actually take that advice, or did it take time?

The first day was like going over my childhood dyslexia, finding my identity, or lack thereof, trying to come up with an identity and what that means, the fear of being found out, and everything that caused.

My mom was amazing; she got me to read. But she had her own issues, coming from her parents. We're amazing people because of both my parents, my siblings, and me. But like all of us, my kids are going to have to go to therapy because of me, right?

This guy, Dr. K—I still see him—told me, “You're really successful. Stop worrying about getting found out and people thinking you're stupid. You're not.”

Dr. K put it a different way. Back in the '50s, really successful people were great entrepreneurs. Very smart people were considered entrepreneurs rather than people who only knew how to read.

I had this whole image because of how I was raised and my education. The only intelligent people are the ones who know how to read. I thought there were all these people who were smarter than me because they had all these other things. I reassured myself in this process that you're not stupid and you don't have to worry. They're not going to find out you're stupid.

Actually, what I do is an art form, and I'm comfortable with that instead of thinking I should be all these other things. Just be comfortable here. That doesn't take anything away from my aggressiveness, my desire to succeed, or any of those other things. And that took a long process.

The only thing is, you did a lot of things to try to alleviate this and try to understand your own inner world. Brené Brown, too—reading that book about anxiety and the fear of exposing yourself. Me being vulnerable and being able to say what I'm saying—is this rooted in some kind of insecurity?

Yes. Remember, I come from a family where my father was an immigrant. My mother is first generation. On my father's side, we were the first generation to get an education, and that was everything. I wasn't very good at it. I couldn't read.

And you clung to that decade after decade.

Sometimes it never goes away. This is very common among great entrepreneurs. Someone who built a $100 million-plus company from scratch—a billionaire, still young. I remember talking to him once, and it was pretty obvious what his answer would be to the question I was going to ask him. This was private, and I said, “Wait a minute, what's your inner monologue?”

He replied, “Why am I so bad?”

“Listen,” I told him, “there's no one—objectively no one on the planet—who thinks you're not talented.”

“Do you have siblings?”

“Yes, I have an older brother and a younger sister.”

“And where do you fit into that mix?”

“I'm the middle child.”

Well, if you've read about this, the oldest child has their point of view on things and how they act, the middle child has their point of view, and the youngest has their point of view. If you're an only child, there's a whole different psychology. I believe in all of that stuff. We all have those issues to overcome.

I was the youngest. My brother Zeke—my mom thought he was the smart one. Rahm was very smart, the artist, and I was the other one, you know. And that sticks with you.

Yeah.

I say it all the time: I just want my mom to love me one week more than she loves you guys.

14. Psychedelics, purpose, and letting go of legacy

Tell me about using psychedelics. I think in the book you call it “the toad.”

The toad. Okay, 5-MeO-DMT. That's the best psychedelic in the world.

Okay. But this is literally the turning point. So let's talk about this.

A friend, someone I knew, had taken this psychedelic with this guy in New Mexico, and he explained it to me.

And I said, “Okay.” Most of the time, when I’m doing my health stuff—and I consider this a health thing, and something emotional is part of health—I always call my brother Zeke and ask him the simplest question. I said, “Can it kill me?” He said, “No.” So I said, “Okay, I’ll do it. I’ll try it.”

I went to New Mexico with Stad, my wife. We weren’t married at the time.

What was going on in your life at this point? You had gone through a divorce. You were in a new relationship. Wasn’t your business screwed up at this point?

I’m divorced at this point. 2022. Okay, 2022. We were coming off that, and “Fight Island” had already happened with the UFC. We were just starting to get back on our feet a little bit.

With 5-MeO, which is the toad, or Bufo, whatever you call it, you smoke it, you read a poem—which is horrible. You have to read a damn poem. I’m dyslexic. What the hell? I can’t escape this reading thing. You have to read it out loud.

Then you disconnect. I don’t know how else to describe it, other than I have another way of describing it, for 10 minutes. Then you have a trip of about 30 minutes, and you realize how small we are in the world and, in a weird way, how insignificant—not in a bad way, like you don’t want to work or anything, or that you’re not aggressive or any of that. You just realize, “Okay, I get what it is.”

You want a meaningful life, not just something good, and that’s more than the ego. Not in a bad way. It just helps me with the ego project. You realize that legacy is nonsense. You just want to be here, be happy, do the best you can, and enjoy your life while you work really hard and have a purpose.

That just started a process for me, experimenting a little bit. I think I’m calmer now. Not that I’m not—I mean, most people in my office would say I’m not calm.

This is the part I need to understand, because Marc Andreessen, who you mentioned a couple of times, was on the show. He’s amazing. But one of the things he talked about on the show was that he hates that everyone in Silicon Valley is trying to get everyone to consume psychedelics because then the founders won’t work as hard.

That’s not true. That’s complete nonsense.

Okay. So here’s what I didn’t understand about the book. I’m having this discussion with Marc.

I mean, it’s all nonsense.

Okay, but tell me the difference. In your work as a person, did it perhaps make you more satisfied instead of being there right now worried about what my legacy will be?

It’ll be what it’s going to be. There will be good parts. There will be bad parts. Like we talked about before we recorded, who was the most important entrepreneur in 1953? Which company? Who’s the guy? I named him, and then you were like, “Okay, you weren’t supposed to know that.” You’re the only person in the world who knows.

Alfred Sloan of GM—nobody gives a shit, right? He was a god, wasn’t he? Hardly anyone knows who Lew Wasserman was. So that’s fine. Presidents, people in entertainment, some singers, some songwriters—very few people are going to have bigger legacies. Probably people who did bad things, right? Really, is that what we’re doing this for?

I do it because I love it. It gives me purpose and meaning. Nine months ago, a year ago, I started this company with Mark Shapiro and some other people. “Mark, let’s do this.” We have a vision for it.

You don’t do things halfway just because you did DMT. Zero halfway, right? There are still a lot of calls. I was up at 5:00 this morning, working out at the office. I did a podcast.

I get it.

I’m going to Montecito for something. I’m working myself to exhaustion. The last 3 weeks have been incredible. My schedule runs through the end of the year. My wife said to me, “What are you?”

But if I didn’t think it was personally meaningful to me and I didn’t enjoy it, I wouldn’t be working as hard sometimes as I do.

I don’t think a guy like you can just sit on the beach. I think you’d be miserable. I think most people would be miserable. One, I think it’s stupid that they care about how high their money pile is. I never think about that. I have money. Obviously, I’m not sitting there thinking about it. It’s ridiculous.

I’m not looking at another person thinking, “Oh, he has more, and I don’t.” I don’t do that.

I work really hard. It’ll be what it’ll be. I love the puzzle. That’s what I love.

You have this great line where you quote Ben Franklin in the book. You’re like, “I don’t think you have any tattoos.” And you said, “If I had tattoos, I’d put them on my knuckles: ‘There is no such thing as a small enemy.’” Which is a bit of a mafia-esque line in the book, by the way.

But that’s not even my favorite Ben Franklin quote. My favorite Ben Franklin quote is—I’m going to paraphrase it—it’s about how you spend your time, because that’s what life is made of. Life isn’t made of money. Life is made of time.

Then there’s what we talked about regarding relationships. You know it’s going to end. It could end tomorrow. You could get hit by a car. You could have died 30 years ago. If that guy had been going a little bit faster, in a different part of your body—

I just did this podcast with Kara Swisher, and I love Kara. I completely disagree with her. I love the fight. She’s amazing.

She was working for Rupert, I think. She had a stroke flying economy. She didn’t realize it, and that was liberating, as awful as it was. She was going to China or Hong Kong for a conference in the beginning. Who the hell knew? She didn’t. I knew.

It sorted something out. She’s better, and she’s amazing. I love arguing with her because I totally disagree with her on a lot of things and agree on some others. She had a stroke around 50. Who would have known this revelation about how I want to spend my time?

Forget legacy. Forget trying to have the biggest fortune. Forget trying to be, in Steve Jobs’ words, the richest man in the cemetery, which is pointless.

This revelation came after decades of therapy. Don’t you think it would have happened without the hallucinogens?

No.

And then, after the fact, you’re more at peace internally. You can go back to Bezos’ idea where it’s like, okay, you’re in the field. You need to be in the field, but you need to learn how to get out of the field. So you’re able to do that now.

Yes.

But your work ethic doesn’t disappear.

No, I work constantly. Even on vacation, of course you’re working, because that whole concept of you not working—you are—but you’re also enjoying different things.

I never, when I was growing up and starting businesses, felt this bad when I took time away from work.

The problem is you can get so obsessed with your work, which you obviously were.

I’m obsessed.

You describe it in the book. I literally thought, “This guy is playing chess in 3D or 4D or something,” because when you say, “I get up, I do 40 minutes of stretching—”

I do dynamic warm-ups.

“I’m going to the sauna for red-light therapy.” It’s like a 2-hour routine. He tries to make his competitors waste 2 hours in the morning doing this stupid stuff while he’s on calls.

Can I tell you something? That whole morning routine—that’s my drug. I don’t drink. I don’t smoke. I don’t do any of that. It makes me feel really good, and then I can go and give it my all.

Other people have other stuff. It’s like the perfect start. A cup of coffee, and I’m ready to go.

15. How Entourage changed Ari’s life

Just one other thing I want to talk to you about is the impact, because you represent Mark Wahlberg, right? He’s like, “Hey, Ari, I’ve got this idea.”

He had this East Coast group, his entourage, and I think Mark came up with it. It was either Mark or his manager, his longtime manager Steve Levinson. They came up with it—I can’t remember which one—but “Entourage” is the perfect name.

And then you end up selling it, right? Then you kind of forget about it, right?

Yeah, at that point. Yeah, before.

But you didn’t think there was—again, it goes back to the fact that you like to say, “Be flexible every day,” because you can’t predict a lot of things. You had no idea of the cultural impact that was going to have.

I thought it was going to be completely negative for my career, my life, everything. Mark Wahlberg and Steve Levinson, his manager, said, “You don’t realize.”

The show started to take off, and he said, “This is going to be the best thing that ever happened to you.” I didn’t believe him at all. I thought it was awful.

My wife, Max's wife, hated it. She never watched it because it was “Mrs. Ari” on Sunday nights in bed. I mean, I didn’t want to go through any of that.

I just started watching it when it finished 2 seasons.

Yeah, right—now?

It was the first time. I had just been fired from ICM and started the new agency.

Okay, hold on. I’m going to get to the rest of the seasons. I just saw this other short interview you did, and they’re giving you other people’s lines. They’re like, “Did you say that? Who said this line?”

You’re reading it, and it’s like, “This sounds like something I said.” Then it turned out to be an Ari Gold line.

That was leading; I was following. You’re sitting there, and the show becomes a hit. People tell you things about the show that I’m not seeing, and you’re thinking, “Did I say that correctly?”

Your character is yourself as a person. You don’t know it, but it’s opening doors. My brother’s in the White House, and he was also a congressman before that—a pretty important congressman. It just happens like a complete volcano erupts.

It was weird, and I think it happened to a lot of Mark’s friends, who were characters, too. It was just a weird event. People would come up and say, “Hug him, [ __ ].” I was like, “What the hell?”

Then I did it. It was great and horrible and fun, and you’re like, “What?”

Weird.

But it had a material impact, like a big financial impact on my business, because I could get anyone on the phone, and the pieces of the puzzle became easier because I could talk to whoever I wanted. Everyone was answering the phone. I could pitch stupid ideas, and they would meet with me. I didn't know how it was going to turn out, but it helped the business.

It gave people a good, bad, and indifferent impression of me—mostly a good one—and of who I was.

The podcast, to a certain extent, really comes back to what I'm obsessed with: playing a similar role. When guests come on my show and on others', do you think they know who you are? No, no, no—not for them. So obviously I focus—hyper-focus—on entrepreneurship. You're an investor, an entrepreneur, a founder, a CEO, and stuff like that, and they'll come. Then I'll hear from them later.

They say, “At every meeting I go to,” he says, “there's no such thing as a cold meeting anymore.” It's a really good way of saying it. There's no cold meeting, and they say it's incredibly impactful.

In some extreme cases, there's this guy, Brad Jacobs, who wrote a book called How to Make a Few Billions. He founded 8 different billion-dollar companies. The book was very successful, and I reviewed it on my other podcast.

He wrote another book a year or two later called How to Make a Few Billions More. In that book, he talks about the fact that 2 people didn't know who he was. I covered his book, and he raised $750 million from 2 people in my audience. He put it in writing—it's in his book.

He had no idea of the impact podcasts have. It's just like, “Well, this guy seems interesting. Let me go and find out what he's working on.” There are a lot of negotiators in the audience. Of course that's going to lead to it. But this idea that there's no such thing as a cold meeting anymore.

16. Ari never had a plan B

Sure. In fact, J.R. says to me, “Are you sure you want to go down this road and show all the damn wounds in the book?” I told him, “I don't know how to do it any other way.” He says, “When you walk into a room, people are going to think they know you.” And I said, “That's fine. It doesn't bother me.”

I had a little bit of that with Entourage, but I'm okay with it. Now I'm getting approached by kids who are young and still watch Entourage, and there's a whole new generation. The good thing is, hopefully, they'll get something out of the book and Entourage.

You have agency for yourself. You know, my own version of The Art of War is: you go all in. I say this all the time: I never had a Plan B. I don't know about you, but in my life, it was have agency or die.

I think, now I'm going to be on social media. No—this is what I'm doing, and I'm going for it. With all the issues, as you know, it's hard to build a business. That's what I hope people get. Jeff Bezos has a great quote: “Plan B should be making Plan A work.”

Yes, exactly. It's a good quote. Great. The book is amazing. I highly recommend it. I'm so glad you wrote the book. I'm so glad we got to hang out. I'm glad we met. This was fantastic. Thank you for your time.

Thank you all. I hope you enjoyed this episode. Please remember to subscribe wherever you listen and leave a review. And be sure to check out my other podcast, Founders. For almost a decade, I’ve obsessively read over 400 biographies of the greatest entrepreneurs in history, looking for ideas they can use in their work. Most of the guests listening on this show found me first through Founders.