Ari Emanuel - The Anti-AI Bet - [Invest Like the Best, EP.448]

My guest today is Ari Emanuel. Ari runs one of the most influential portfolios in global sports, entertainment, and media. He oversees TKO, which includes the UFC and WWE, serves as the Executive Chairman of WME Group, and recently founded MARI, a new company focused on global events and live experiences. At the center of this conversation is Ari's anti-AI bet: as AI makes digital content cheaper and everyday work more automated, he believes the value will increasingly concentrate in live and physical experiences. He explains how he’s building his portfolio around that belief, what defines a great live experience, and how he thinks about AI’s impact on content and IP. Ari is best known as a dealmaker, and he shares the principles behind his success – relentless follow-up, over-communication, velocity, and an obsession with making things happen – and how those things become the operating system he uses today. If you’re listening to this, I recommend watching the video of this interview. Ari’s energy is constant and visceral, and gives a different dimension to this episode. Please enjoy my conversation with Ari Emanuel. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ramp.com/invest to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. –- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:20) Meet Ari Emanuel (00:05:32) The UFC Story (00:10:03) Mindset, Relentlessness, and Emotional Endurance (00:13:52) AI’s Impact on Content and Distribution (00:18:44) Value, Taste, and the Future of Content (00:19:43) The Anti-AI Bet: Live Events and Experiences (00:22:39) Monetization, User Experience, and the Premium Economy (00:26:21) Building and Scaling Live Event Businesses (00:27:16) Boxing and the Business of Live Entertainment (00:28:45) Lessons from Dana White and Dealing with Dyslexia (00:31:32) Getting a Job at CAA and How to Be a Successful Agent (00:35:50) Ari’s Operating System (00:38:04) Lessons from Egon Durban (00:39:36) Betting on Himself and Elon (00:43:16) Who Wants to be Normal?! (00:44:23) The Art of Dealmaking (00:48:58) Money, Family, and Learning from Mistakes (00:52:45) The Future of Tech, Media and Content (00:57:32) Concerns and Excitement about the Future (01:00:16) Art (01:01:01) The Kindest Thing

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Patrick O'Shaughnessy?

  Ramp is the only platform built to make your finance team leaner, faster, and better, saving businesses 5% annually on average, so you can stay focused on growth. Ramp just opened for business in the United Kingdom. So if you're running a business in the UK, you can now use Ramp's AI-powered finance platform to manage cards, expenses, bills, approvals, and accounting all in one place. I run my business on Ramp, and so should you. Learn more at ramp.com/invest. Rogo is the AI platform purpose-built for financial institutions, serving tens of thousands of bankers and investors at hundreds of leading firms worldwide. Rogo's AI agents autonomously execute large chunk of your firm's workflows. They can screen deals,

• 0:42Patrick O'Shaughnessy?

  draft SIMs, run buyer outreach, and do diligence on data rooms, all with full security and compliance handled. Every action feeds Rogo Intelligence, the firm's context layer, turning years of deal experience into a secure, governed institutional memory that makes each new transaction stronger than the last. To learn more, visit rogo.com/invest. OpenAI, Cursor, Anthy, and Vercel all have something in common. They all use WorkOS. To achieve enterprise adoption at scale, you have to deliver on core capabilities like SSO, SCIM, RBAC, and audit logs. Instead of spending months building these mission-critical capabilities yourself, you can just use WorkOS APIs to gain all of them on day zero. Visit workos.com to get started.

• 1:31Patrick O'Shaughnessy?

  Hello and welcome, everyone. I'm Patrick O'Neal, and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus Review, along with all of our podcasts, at joincolossus.com.

• 1:56Speaker 01

  Patrick O'Neal is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc.

• 2:25Patrick O'Shaughnessy?

  My guest today is Ari Emanuel. Ari runs one of the most influential portfolios in global sports, entertainment and media. He oversees TKO, which includes the UFC and WWE, serves as the executive chairman of WME Group, and recently founded Mari, a new company focused on global events and live experiences. At the center of this conversation is Ari's anti-AI bet. As AI makes digital content cheaper and everyday work more automated, he believes that value will increasingly concentrate in live and physical experiences. He explains how he's building his portfolio around that belief, what defines a great live experience, and how he thinks about AI's impact on content and IP. Ari is best known as a dealmaker, and he shares the principles behind his success: relentless follow-up, over-communication, velocity, and an obsession with making things happen,

• 3:10Patrick O'Shaughnessy?

  and how those things become the operating system he uses today. If you're listening to this, I recommend watching the video of this interview. Ari's energy is constant and visceral, and gives a different dimension to this episode. Please enjoy my conversation with Ari Emanuel.

• 3:26Patrick O'Shaughnessy?

  We're going to UFC tomorrow night. I've never seen it, and I've never been to an event, but it has captured everyone's imagination. It's this amazing business. He bought it in 2016. Can you just explain the magic of this business?

• 3:37Speaker 02

  When I started, I represented the WWE, and I represented the UFC. When I signed the UFC, it was on Spike. We had a whole division inside the company looking at ratings. And all of a sudden, they came and they showed me, here's this thing on Spike, and here's the numbers. And then I realized, wow, this thing's ratings are starting to move. So I figured out, oh, it's Dana White and the Fatidas. And I represented the WWE, and they're close enough. So I called them.

• 4:03Patrick O'Shaughnessy?

  Called Dana.

• 4:04Speaker 02

  Yeah, and eventually I got a meeting, and I completely screwed up the meeting. I was talking about the WWE. It was just bad. It was one of my worst signing meetings. And I just kept at it. Because I knew, based on their ratings and what they were getting as a license fee, a domestic license fee, it wasn't enough money. And I knew if I got my hands on it, I could do some stuff with it, just as a representative. So eventually, after doing a couple of things, he signed with me. The organization signed with me. They were making $15 million a year from Spike. And I think the first deal I made at Spike, I increased it to 75, something like that. And we made a video game deal, which they had never had. And after 20 years, we moved it to Fox for $150 million.

• 4:46Patrick O'Shaughnessy?

  Good growth rate so far.

• 4:47Speaker 02

  We've done well. And then my life changed because Silver Lake came into my life. We started buying companies. We bought IMG and we had started building an infrastructure. Because of IMG, they had sports and events. An infrastructure to whether it be licensing, distribution, production. A lot of things that companies needed on a global basis, not just a domestic basis. And then the fatitas decided they wanted to sell. And a little before that, we had bought PBR, the professional bull writing. Had started turning that thing around. And Silver Lake Egon, my partner Egon Durbin, realized we do more negotiations on the domestic side broadcasting for TV shows and movies than almost anybody else. You could handle, and we'd already done it for other people. You could handle sports if you owned it.

• 5:31Speaker 02

  And I concluded where the world was going. I was talking about it's going to go to streaming. Sports is going to be important. It was on cable. It's going to move there because for AVOD and everything. So we buy it. Now, at the time, when we bought IMG, the closest bidder, I think, was Chernin at 1.9 billion. We paid 2.4. Everybody thought it was the highest price ever paid. When we bought UFC on the current trajectory, it was 20 times. If I made the proper domestic deal, I could take the leverage down. And I thought, I just did the math. Here's how much they need it because of here's how much programming. Because remember at the time, Fox owned these RSNs, the regional players. And they had just the spokes off the library. And I said, they have to pay. Here's a normal increase. Not like the rest of your people that sit in this chair would ask them how they do their

• 6:16Speaker 02

  analysis. Cut to, we buy it. People think we're crazy. And then the world blows up. Rupert decides to sell to Disney. Those two people are not bidding. Comcast didn't want it. Warner's didn't want it. And Paramount had not decided what they were going to be. So now I'm looking at myself. We're fucked. I got no bidders and my contract's coming up in a year. So we go back to Fox, sans what they were going to have remaining and say, you should buy this. Lachlan didn't want to do it for his point of view. I think it was three or four months into our deal coming off. Fox, ESPN fires John Skipper, who was always shining me on that he never won it. And

• 6:58Speaker 02

  Bob Iger and Kevin Mayer say we want it because we're going to go direct on ESPN. And we make a deal for both, you're coming on Saturday to the pay-per-views, which we have stopped now since we're going to Paramount. And we have these just normal fights every weekend, our fight nights. So I did my job. It was emotionally trying, but we got it done. And what then happened, which was incredible and horrible all at once. Covid happens, world shuts down. Dana goes, we're putting the fights on. I said, I got your back. He goes, get me an island. I call my partners in the Middle East, in Abu Dhabi, and Kal Doon, who owns Man City. And I said, we need an island and we need planes and we need testing.

• 7:39Patrick O'Shaughnessy?

  Everything.

• 7:39Speaker 02

  Everything, because they're not going to be honest. We need this. And he says, yes. So we bring fighters in from Europe. We bring fighters in from the United States. We test. Everybody's isolated for two weeks and we spent two months, I think, maybe three months there.

• 7:51Patrick O'Shaughnessy?

  And no one else is doing anything?

• 7:52Speaker 02

  No, no sports on and it blows up.

• 7:55Patrick O'Shaughnessy?

  How much of an inflection was that in audience size?

• 7:57Speaker 02

  Oh, our pay-per-views were getting, I think we were getting like a million views. It was insane because there was no sports on, zero. I don't know if you remember that period. It was nothing.

• 8:07Patrick O'Shaughnessy?

  Yeah, there's literally nothing.

• 8:08Speaker 02

  And we were the first two up, the UFC and PBR. And we had a whole document on our testing. It was crazy.

• 8:14Patrick O'Shaughnessy?

  If I boiled down your whole life, is it make shit happen over and over and over?

• 8:17Speaker 02

  Yeah, relentlessly not taking no. But I think that's most successful people.

• 8:23Patrick O'Shaughnessy?

  You have a very distinctive style of being extremely good at that. How did that develop?

• 8:28Speaker 02

  Well, when you have two older brothers that are really good at their job and a mother and a father that just push you. And there's many good things to dyslexia. And any parent that has a dyslexic child, I will tell you, it does get better if you hang in there. So I don't get embarrassed easily. Somebody saying no, who cares? I just keep on trying to open more doors. So those elements in my life, my mom, my brothers, competition. And I'm competitive with myself, very.

• 8:55Patrick O'Shaughnessy?

  What's that feel like?

• 8:56Speaker 02

  Horrible.

• 9:00Speaker 02

  You know, it's exhausting, but it's gotten better.

• 9:03Patrick O'Shaughnessy?

  Well, what is it like internally? Are you literally waking up like yelling at yourself?

• 9:06Speaker 02

  Oh, yeah, yeah, yeah.

• 9:07Patrick O'Shaughnessy?

  Every day?

• 9:07Speaker 02

  Yeah, oh, yeah. There's that voice ticking off all the things you gotta do and playing the chess match. And one of the things that Jeff Bezos said to me, it was so good, it really did help me. He said, you have to, at your age, Ari, now, know when you're on the field and know when you're off the field. The problem in the past, it was helpful to a point, but you can't get really successful. I was always on the field, always.

• 9:29Patrick O'Shaughnessy?

  Defined as what?

• 9:30Speaker 02

  Meaning I was always playing chess in any conversation, thinking of the angle, working the situation. And sometimes it should just be chill the fuck out. I never realized that. Many things helped me, but that little conversation is actually right. And it actually makes when you're on the field, better. And I wasn't mature enough to realize that until somebody slapped me in the face.

• 9:53Patrick O'Shaughnessy?

  And being off the field for you means what?

• 9:55Speaker 02

  Well, in any conversation, I'm not.

• 9:57Patrick O'Shaughnessy?

  You're not calculating 4 million angles?

• 9:59Speaker 02

  I'm not calculating out all the different things. It can just be a good conversation. Now, I'm curious, so I read a ton, I read a ton of articles, I tell my office, I want to talk to that person, I want to talk to that person. I'm on the field a lot, but there's sometimes chill the fuck out. You know, you don't have to be on the field.

• 10:16Patrick O'Shaughnessy?

  What about wrestling? How good were you at wrestling? What made you good?

• 10:18Speaker 02

  I was pretty good.

• 10:19Patrick O'Shaughnessy?

  What was your style? What did they teach you?

• 10:21Speaker 02

  I was fast, I was quick, takedowns. You know what it does do, wrestling? And I think MMA and when you're in high school and you have to go from my size now to 132 pounds, easier when you're younger, and you have to starve yourself, plus work out and go to school. And the mental fortitude of that just keeps on going in your life, that you can handle that emotional pain. And that's also in business. I can handle a lot of emotional pain. And I think one of the hardest things now for kids, which I hope I teach my kids, is that emotional endurance that you need in life right now is even more challenging. I think business, just because business is no longer binary. It's multi-layered. And you have to realize sometimes you have to have a relationship to somebody, even though there's things in that relationship you don't like. And I don't think that was in the past in business, you

• 11:06Speaker 02

  had to think through all those things. And it's just emotionally draining right now because there's so many things going on.

• 11:12Patrick O'Shaughnessy?

  What was the most extreme emotional pain you ever felt in business?

• 11:15Speaker 02

  The situation.

• 11:16Patrick O'Shaughnessy?

  The contract thing?

• 11:18Speaker 02

  With the UFC, because I put all the chips in the middle, $4.2 billion in the middle. Clients were investing, my biggest investors investing. I had done the calculation. I didn't see that Rupert was going to sell and we're coming to the end. Contract's four months away. Because of that, my thyroid went on the fritz with so much pressure. I'd never had that physical action. I went down to 142 pounds.

• 11:40Patrick O'Shaughnessy?

  Bullshit.

• 11:41Speaker 02

  Dana talks about this gray hair and emaciated sweating. I mean, it was horrible. And finally, I went to the doctor and he goes, you know, your thyroid's going at a rate. So that was hard. But once it got done, everything came back and calmed down. No longer was on the field all the time.

• 11:57Patrick O'Shaughnessy?

  What does the power dynamic feel like today around content, those that own it? And the places that it could be distributed versus the past of that same power structure? Like, how's it evolved?

• 12:08Speaker 02

  In the past, you had the FinCEN rule where the owners of distribution couldn't own the whole thing. Now with cable gone and broadcast, not gone, but in decline. We just talked about, is it going to be Warner Brothers with Netflix? Or is it going to be Paramount? There's not a lot of supply chain. These guys are doing it and they're doing it within each other's boundaries. Sony's one of the suppliers. There's some. Before, there was a lot. Even before, when I was in the business, you had tax incentives for production. There's a company called Whit Thomas and all these independents used to supply. They used to get tax benefits and supply great programming. It was an unbelievable business. You had syndication and that's how at the beginning of my career, we made all this money. Television was a great business.

• 12:51Speaker 02

  You put a show on, if you were an independent, you'd own the show. Carson Warner, Tom Warner, who owns the Boston Red Sox. And I think he still owns Liverpool and he owns some foreign company. So you put the 70's show on or the Cosby show on or Roseanne or you do 150 episodes. You sell to a station group for $5 million an episode, 150. You can do the math.

• 13:10Patrick O'Shaughnessy?

  Yeah, I can.

• 13:11Speaker 02

  And then you do a second window into cable. And then a third window happened when Netflix came around. And then you do that multiple after they've run its course. The second window of syndication, the third window of syndication, the fourth one. Now, it's really just, which we just did for The Office, and you can do for The Simpsons, and you can do for Family Guy, and Curb, and Seinfeld. They're paying a lot of money. For The Office, you're doing it at Comcast. That's the window. It's $500 million for the new window. It's a very good deal. But then, I think about four years ago, three years ago, the Writers Guild took away our packages. But it used to be you had all these independents supplying all this content. Now, it's the majors supplying the majors. So, it's a lot different. And I do think that has not been beneficial.

• 13:56Speaker 02

  I do think what's going to happen now, though, AI is definitely going to reduce costs. So, I had a client who's a writer-director. I'm not going to say who. He's got to do an outline for a project. He gave, I think, Grok or Perplexity an incredible prompt, based on a piece of IP. The outline for the project.

• 14:16Patrick O'Shaughnessy?

  Pretty close.

• 14:17Speaker 02

  Now, remember, AI, as people say, is the greatest average, which it is. He said it was unbelievable. Now, he's going to have to do work on it. But that would have taken months.

• 14:26Patrick O'Shaughnessy?

  Is your take on AI that it basically supercharges the very best people disproportionately?

• 14:29Speaker 02

  Yes.

• 14:30Patrick O'Shaughnessy?

  Have you seen that elsewhere?

• 14:32Speaker 02

  I'm not in other businesses, but my son works at Apple. I mean, I think programmers are feeling that. I think they're feeling that in probably finance.

• 14:39Patrick O'Shaughnessy?

  When you saw Sora 2, what'd you think?

• 14:41Speaker 02

  Oh, I wanted to sue him because he stole a bunch of stuff. He put the UFC up there. They put the WWE, they put bull riding and really bad stuff. But what it's going to do, whether it be Sora, Grok, it's just going to make production costs, filming, DPs. And then you're going to be able to either bring Betty Davis back or Elizabeth Taylor. It's going to happen. So, you're going to see, in a good way, like in the music business, you can do an album in your bed. I think the same thing's true

• 15:08Patrick O'Shaughnessy?

  Do a movie in your bed.

• 15:09Speaker 02

  in the movie business. I don't know where it's going, but it's going to be cheaper, and there's going to be a lot of it. And I think the walls around creating content for the first time because of the cost, because it used to cost $100.

• 15:19Patrick O'Shaughnessy?

  $100 a month.

• 15:20Speaker 02

  It's no longer going to be that. So, that's going to come down.

• 15:23Patrick O'Shaughnessy?

  In a world where the marginal cost of content creation is getting close to zero, where does the value accrue?

• 15:29Speaker 02

  Well, if we have four great bidders and maybe with six wifi, maybe everybody with their social platforms is a distributor through social. Let's just say we're right. The marginal cost becomes zero and you're Dwayne Johnson. And you have, I don't know how many people he has on social.

• 15:46Patrick O'Shaughnessy?

  A lot.

• 15:47Speaker 02

  A lot, or Kim Kardashian, or you name the person. Are you not a distributor? Those are the questions that are going to arise pretty soon. And then I say to people at William Morris, for the first time, taste matters a lot.

• 16:01Patrick O'Shaughnessy?

  Say a little bit more about that.

• 16:02Speaker 02

  I don't know about you, but I get called all the time. This is a great script. Shut the fuck up. Knowing what is good and what is commercial and what sells.

• 16:11Patrick O'Shaughnessy?

  Yeah.

• 16:11Speaker 02

  Now, I'm not always right. I'm probably batting 300. I'm in the Hall of Fame, so 60% of the time I'm screwed. But people with taste that know this business, that know kind of what an audience, a mass audience likes is hard. So if you have taste and you're seeing a lot of programming, you can say, there's talent there. That actually has value. So you're Dwayne Johnson. Let's just take it out to this. Let's just say my conclusion's right. And you take it out to its farthest limit where Dwayne Johnson has a development team and they're looking for stuff and they're picking it and they're putting on their service. For Dwayne, and Dwayne's paying that person. I don't know if they're paying him a million dollars or $10,000 because the thing costs nothing. There's a value proposition there and you're getting a sponsor, you're getting subs. I don't know. In some capacity, that's going to happen.

• 16:56Speaker 02

  Brands are going to be really important. All IP is going to be really important. I think the value of sports is going to be even more valuable.

• 17:03Patrick O'Shaughnessy?

  What about the content side of this? The use of IP.

• 17:08Speaker 02

  Yeah, that's going to be a huge business. I do believe, I think it's David Ellison's bet that there's going to be more need for content than there's ever been and there's going to be more consumption. I agree with that and it's going to be cheaper.

• 17:19Patrick O'Shaughnessy?

  What about the use of content by labs where maybe they shouldn't have used it to train models, for example?

• 17:25Speaker 02

  Yeah, they should all get sued.

• 17:27Patrick O'Shaughnessy?

  How do you think that'll play out?

• 17:28Speaker 02

  We sent the bad letter to Sam, stop using the UFC and the WWE and SOA. So they're gonna have to pay, I think, unless the Supreme Court says something. When Larry David creates Curb and Seinfeld and you're taking it to train your model and you're gonna make a lot of zeros, you don't think Larry David deserves to get paid? I think that's crazy.

• 17:48Patrick O'Shaughnessy?

  Let's talk about IRL stuff in this context. Obviously, you've created a portfolio of some of the marquee live events. And I know you believe very deeply in this. Is there a way to think about this almost like the anti-AI bet or the AI proof bet?

• 18:02Speaker 02

  AI is going to be

• 18:03Patrick O'Shaughnessy?

  Big.

• 18:03Speaker 02

  Big. Which I think is a proper conclusion. There's a really lot of smart people spending a lot of money at it and they're smarter than me. So Netherlands just said four day work weeks. Drive times now are 11 to 4 across America. Hotel bookings, Thursday's way up. And there's a lot of more data points to this. So the weekend starts Thursday now and we're 2025, maybe 2027. They start Wednesday. So we're social animals. You're coming to a UFC fight. You're a social guy. What are you gonna do? You're gonna watch a lot of content. David Ellison's conclusion. You're gonna watch a lot of content. There's gonna be more content than ever, costs zero on his service, on four big services. You're gonna be going to concerts, going to stand up, going to live events, sports,

• 18:46Speaker 02

  or my live events that I've just bought. So the value of that, because there's only so much. And yeah, people are creating new ones, but so that's my whole bet. I don't know how to write an algorithm for AI. I don't know how to build a data center. I'm not in a chip business. I just know how to create really great live events, monetize them, have a great user experience. And it's the opposite, because data centers aren't the opposite bet. Live is the opposite bet.

• 19:11Patrick O'Shaughnessy?

  What makes a great live event? What are the ingredients?

• 19:14Speaker 02

  Well, there has to be a specific audience. So in art, there's a very specific audience. There's a culture around art. It's global. There's really good conversation about it. Cars, anti-cars, another one of my businesses. Very specific. Sports, UFC, bull riding, WWE, very specific. Taste, food festivals. So I'm in the areas that I know there is great cultural stickiness.

• 19:39Patrick O'Shaughnessy?

  Affinity.

• 19:40Speaker 02

  Affinity. It's global. So one of the things that we know, why did we do Freeze? It was only in two places. It was in UK and New York. We knew there were art festivals all over the place run poorly. We knew we could take it globally. We could spread the sponsorship. We could determine that city needs them and they would pay us to bring events. So we'd get site fees. So, hey, bring Freeze, great brand, knows how to do this properly. The food around it, lectures, et cetera. We're going to pay you to come here for 10 years to put on the event. We just closed that deal in Abu Dhabi. So when you start doing those things properly, in our Madrid Open, which is our tennis tournament. It's one of the nine 1000s. We're going to build another stadium to build another food festival. We're going to do concerts after the tennis tournament. We just know how to do it.

• 20:24Speaker 02

  So when we look at these things, we look at them in a way that, what are they missing? Because we're one of the only companies on a global basis that do live events. Sometimes you have companies that do great live events, but they're local. There are guys that are in Arizona. There are guys that are in just the UK. When they come into our organization, we're in 32 coming. We know, oh, you know something? There's an affinity here.

• 20:45Patrick O'Shaughnessy?

  You said two other things, monetization and user experience. I'm going to say monetization because I have a specific question about it. What is great user experience?

• 20:51Speaker 02

  So when they go around, there's food, there's lectures, there's surrounding events that make the event itself and inside the event really special. And it's a great way. I can't stress enough the need for people to get community. Cause we're all sitting staring. I remember one of the things that made me think about this also, about why live events were so important and sports were so important. Tiger talked about at one point, I saw a documentary, I think it was, when he first won, the people were clapping. Second time, uh-uh. Phones were up and people were screaming. And that's because that thing, you want to show how great your life is. And that also thing detaches you and you want a place where you can have with other people a great experience. And that just bodes well for music, live sports, live events.

• 21:36Patrick O'Shaughnessy?

  And you're selling status to some degree, like you're selling the video they're taking.

• 21:39Speaker 02

  This is status.

• 21:41Patrick O'Shaughnessy?

  Monetization is the one that intrigues me the most based on a conversation you and I've had before, which is we're still figuring out the demand curve inside of one of these events.

• 21:50Speaker 02

  You know, we bought this company On Location. Do you know about that?

• 21:53Patrick O'Shaughnessy?

  A little bit, but it reminded me.

• 21:54Speaker 02

  So On Location, Jerry Cardinal first owned it with the NFL, and they were doing the premium hospitality for the Super Bowl. And we thought, wow, that's incredible because people are asking for premiums now and rich people are asking for more and more because they can get everything. So they won't even splurge for it. And that there was tiered market, not in a bad way. Some people are going to pay a hundred dollars and some people are going to pay three hundred dollars. And then some people are going to pay crazy. So in the Super Bowl, go to Tiffany's and get a blue football and have 10 people with you and get a lecture from Peyton Manning and walk on the field pregame and come out with the team and be on the stage for weigh-ins at the UFC and sit at the table with Dana

• 22:37Speaker 02

  White. And for that, I'm going to pay $50,000 a ticket. I'm going to pay $300,000 for the Super Bowl or XYZ for the Olympics. It's crazy.

• 22:44Patrick O'Shaughnessy?

  And you still haven't found the...

• 22:46Speaker 02

  Oh, no, no, we're adding. So the Olympics, FIFA, UFC, WWE, in every category, there's premiums and people pay...

• 22:55Patrick O'Shaughnessy?

  Crazy.

• 22:56Speaker 02

  Crazy.

• 22:56Patrick O'Shaughnessy?

  How much of it do you think is them paying for the video that they get on that versus the actual experience?

• 23:01Speaker 02

  I don't know. I think it has...

• 23:02Patrick O'Shaughnessy?

  Pretty high.

• 23:02Speaker 02

  Yeah, pretty high. But I think that's fantastic.

• 23:04Patrick O'Shaughnessy?

  That's fine.

• 23:04Speaker 02

  You work your ass off. You love this thing, whether it be music, events, sports. I want a different experience in my life. Yes, for that, but just life. And I think COVID made that happen too. And people are doing it. Where it ends, I don't know, but it is a huge premium business.

• 23:22Patrick O'Shaughnessy?

  How far can you push this? It feels like you've collected lots of the marquee assets and things that you love. What's the runway feel like to you for this thesis?

• 23:30Speaker 02

  So here's one thing that we're doing in the live events business that I started.

• 23:33Patrick O'Shaughnessy?

  This is Freeze and this is-

• 23:35Speaker 02

  Yeah, this is, it's called Mari.

• 23:36Patrick O'Shaughnessy?

  Inside of Mari.

• 23:37Speaker 02

  This is Freeze, Barrett-Jackson, our tennis tournaments, our participatory sports like Escape from Malcatraz and Melbourne Marathon and our Taste Festivals, Winter Wonderland, that business. So we bought a ticketing business inside that, this thing called TodayTix. The ticketing business, mainly they do, mainly, almost all they do is theater business. When COVID happened, unlike other ticketing business, which had to keep on operating, they shut the whole thing down and rewrote the operating system and it's incredible. So we'll create a destination with an incredible ticketing asset. Where I think it's going is hopefully we create a platform that has events, because we operate events pretty well, plus a destination, you white label ticketing, then we can create a sponsorship layer,

• 24:21Speaker 02

  site fee layer, and maybe white label some stuff and go from there. So that's the dream, that's the wish.

• 24:26Patrick O'Shaughnessy?

  What is the most surprising thing about the landscape of sports and live events today?

• 24:30Speaker 02

  Well, when you think about sports, so you have the beast of all beasts, NFL, NBA, global, baseball, hockey, English Premier League, Spanish League, French, they're all owned by federations and there's very few independent and very few people that know how to run them. When we were buying the UFC and we were having this argument internally, Egon would say, well, the people that can pay the most are the broadcast. Well, they would ruin the sport. There's so many things that happen to run one of these things. You have to make really hard decisions. First of all, so there's a limited amount that is available to buy in the wrong hands, the ones that are independent. Unless Adam Silver's there, unless Roger Goodell's there, those things don't run the way they're supposed to. Those things are hard and the same thing with our sport.

• 25:14Speaker 02

  We're about to start our boxing business.

• 25:16Patrick O'Shaughnessy?

  So if you approach boxing-

• 25:17Speaker 02

  We have announced the boxing league with Paramount and we do the big, huge, super fights.

• 25:22Patrick O'Shaughnessy?

  As you approach that opportunity, tell me the story of how you build this.

• 25:25Speaker 02

  Let's go back. Don King screws over Ali, the Ali act gets passed. It changes the sport. Now, first of all, to create a league in a combat sport, the only person that could have ever done it is Dana White, ever. He did it at the UFC. And the other only person that could have done it, it's sports entertainment, is Vince McMahon. It's incredible. So, we now look at that. The Ali act's gonna exist. We're gonna put it, hopefully, we can get this passed, add an element to it, that we could create another opportunity for fighters. We're gonna have, like we have in the UFC, the best fighters fight the best fighters. And we think we can create like a UFC, but with boxing, in Zuffa boxing. And if we do that, I think fighters are gonna make more money. Because right now, you don't know any great fighters. It's not like-

• 26:09Patrick O'Shaughnessy?

  I literally can't name one.

• 26:10Speaker 02

  You can't name one. We think we can do that, and then boxers will make more money. It will be a business for them. And it's a great sport. I was more jazzed than ever about that. We put a great fight on at Allegiant Stadium, is where the Raiders play. And Mark Davis was unbelievable, my partner, Egon Durbin, who is part of that, was unbelievable helping us with that. And when you put a great fight and a great card on, how many people showed up? Because it's so ingrained, boxing into our world. Seventy thousand people. And they did not leave. It was spectacular. So, if we do that now, I think it can be as big or bigger than the UFC and the WWE, and they're big. And we're gonna do our best to do it, because I think the audience wants it, and I think it'd be great for fighters.

• 26:51Patrick O'Shaughnessy?

  What makes Dana so incredible as an entrepreneur? What is his superpower?

• 26:55Speaker 02

  One, he loves it.

• 26:56Patrick O'Shaughnessy?

  Good place to start.

• 26:58Speaker 02

  He really does love combat sports. Two is, he's not scared. He's just not. When you look at him, his poker play, I don't know how he does it, because if I'm betting five dollars, I can't play poker. But, you know, he makes fun of me when we do this, right? I'll tell you a story. We're celebrating the deal at ESPN. He's, "Fly, come to Vegas, we're going out for dinner, we're celebrating." I'm like, "Okay, what does that mean?" "We're gonna go gamble." "What?" "I don't gamble." I said, "Okay, how much do you want on your line?" I think I said twenty-five thousand. And we're in the car and we're driving. He goes, you're the biggest gambler I know to me. I'm like, no, I'm not. He goes, you just bet on me $4.2 billion. He took a million dollars. I think he got me up to $50,000 on the line.

• 27:43Speaker 02

  And I said, well, that's not a gamble because I did my version in my head, my calculation. So he is just a unique individual that he's not partisan. He's loyal and he has a vision. He backs your play. He's just that guy and he's not afraid to take on a challenge and do the work. I mean, he works constantly. So in this space, he just knows the space so well and he's relentless.

• 28:08Patrick O'Shaughnessy?

  How did you learn to become not afraid?

• 28:11Speaker 02

  Well, when you're dyslexic and people are making fun of you.

• 28:13Patrick O'Shaughnessy?

  Just power through.

• 28:15Speaker 02

  You can't be embarrassed. There's nothing more embarrassing when you're 13 years old. They put me in, in.

• 28:21Patrick O'Shaughnessy?

  Like a remedial class or something?

• 28:23Speaker 02

  Well, it wasn't remedial. It was.

• 28:24Patrick O'Shaughnessy?

  Worse than that?

• 28:25Speaker 02

  Yeah. And you're in school and you know, you're not stupid. I was in special ed. Well, there can't be more embarrassing than that. So anything now, I don't give a shit. You can't embarrass me. And it was actually that simple. When you're in special ed and you're 15 years old and you're in high school and your two brothers are some of the smartest kids from that high school and you have to walk home, you're really good at math. You just can't read just because of how your brain's wired. And they put you in special ed, you're like, what the fuck?

• 28:50Patrick O'Shaughnessy?

  So what was the first experience though of clicking out of that to the opposite of, oh shit, I could be really good at something?

• 28:56Speaker 02

  I don't know what it was. My three boys were dyslexic because it does get passed on. My father was dyslexic. And when my boys were dyslexic, I put them into this class, this school in the summer called Lyndon Moot Bell. They run a marathon on their brains to teach their left back lobe how to read. It's four hours a day relentless. My mom did that to me. There was no Lyndon Moot Bell. People call tiger moms. I don't know what you call a Jewish tiger mom, but it's brutal.

• 29:24Speaker 02

  So I don't care what anybody else is saying. You're going to college, because I wasn't going to go to college. You're reading, you're getting good grades. Tiger mom, a degree of 10.

• 29:34Patrick O'Shaughnessy?

  And then what was the first early 20s, post-college, big hit of success?

• 29:38Speaker 02

  Well, I screwed around in Europe for a year. I came back to New York and a friend of mine at the time, what was this guy by the name of? Michael Mendelson. And he was working for this company. I used to wake up at 5:00 in the morning, just watch TV. And I used to watch The Crusher and The Bruiser and the regional wrestling and TV shows. And never knew how it was made, but watched everything. So I said, what are you doing? And he said to me, oh, I'm working at William Morris. Now, how the fuck am I supposed to know William Morris? Because I'm from Chicago, my father's a doctor, he's an immigrant. William Morris, what the fuck's William Morris? So he tells me. And for whatever reason, bang, the light went on. And I didn't have a job. I didn't know what I was going to go to business school, back to Northwestern, night school, business school. And I was going to work at the Merc, because I used to do summer jobs at the Merc in the pits. 220, 220, I used to do all that. I thought I was going to do that.

• 30:23Speaker 02

  It was good math. And for whatever reason, the minute he told me that, I said, that's a gig for me. Got a job working for this guy by the name of Robbie Lance. I was working for Bob Duvall, who went to work for Robbie Lance. And it just started. I helped with the Tennessee Williams, London Helmet and National Helmet Estates, making rights deals for them and organized it properly. He was, I think at the time, 86. And he turns to me, and I was doing a really good job. And he says, I'm not promoting anybody. You should go out to LA and you can make a lot of money. And he set up two interviews for me. One at CAA and one at this company called Leading Artists. And got the job in the mailroom at CAA, making 15 cents a mile.

• 31:03Patrick O'Shaughnessy?

  Where'd you learn in the mailroom?

• 31:04Speaker 02

  That I hated it. I learned how to actually drive around LA. And I learned the hierarchy of the business. Business affairs people, studio heads, at the time where movie stars played. The movie business, how important it was, but the television business made a lot of money. And I realized I could never be in the movie business.

• 31:23Patrick O'Shaughnessy?

  Why?

• 31:24Speaker 02

  Because you would have to do coverage while you're in the mailroom. I'm dyslexic. Movie script, 130 pages, 120 pages. TV script, 30 pages. I'm not spending all weekend. Now, that little thing, because the money was in television.

• 31:39Patrick O'Shaughnessy?

  That little change, two doors.

• 31:41Speaker 02

  Bang. And then, when we started Endeavor with George Gilder's book, and I'm reading it, and Life After Television, I'm like, there's going to be a lot more distribution. There's only so much content creators at the time. Content was going to change and expand, but there's limited supply and demand. Prices are going up for creators. And television, where you could make, I went on Bill Haber's desk that had a television at the time, it was Michael Ovitz, Ron Meyer, Bill Haber. The huge money, huge money was coming in because of television. Not that the movie business wasn't, because you had the DVD business at the time, and gross participation and everything else. But you had a hit television show, like Alf. I remember sitting on the desk, listening to all the calls, and there was a fight between Michael Ovitz and Bernie Pearlstein on Alf, what they were paying

• 32:26Speaker 02

  out. That thing paid out a fortune. And then it paid out syndication one, syndication two. And I'm like, that baby's for me.

• 32:33Patrick O'Shaughnessy?

  What was the key to being an exceptional agent?

• 32:36Speaker 02

  Being relentless. When you're trying to get somebody staffed, one of the greatest things Robbie Lance ever taught me, you know why people call me back, Robbie, you say in this Austrian accent? Because I represent Milos Forman, who did Amadeus, and I represent Peter Schaffer. I represent Al Pacino. They'll call you back. So having a great client meant you had access. So you had to have taste, and you had to get great clients. And once you did that, and they continued to grow, you became more and more powerful. So that's what I did.

• 33:03Patrick O'Shaughnessy?

  How did you get your first great client? Who was it?

• 33:05Speaker 02

  I'm at CAA, and I go to this company, Intertalent. And Mark Rosen, I'm not sure it was my first client, it might have been my second client, because Greg Daniels, who created The Office, and King of the Hill, and Parks and Rec, he might have been my first client. But Amy Littman, who created Party at Five, also might have been, I'm too old.

• 33:21Patrick O'Shaughnessy?

  Yeah.

• 33:22Speaker 02

  But they had created a show, I thought the shows were great, took over those clients, they led to other clients. And then, back then, there was no YouTube, there was no Instagram, there was none of that. People weren't creating that way. The great shows were, they would go from, at the time, Saturday Night Live, to The Simpsons, this whole Harvard Lampoon group. And all those, a lot of them, not all, SNL guys, the writers, because I was in the writer business, came from the Lampoon, Harvard, going to Harvard.

• 33:48Patrick O'Shaughnessy?

  I'll go there.

• 33:49Speaker 02

  So, signed a bunch of people up for that, put them on SNL, SNL, they went to The Simpsons, or they had the pedigree, and then you moved them around.

• 33:55Patrick O'Shaughnessy?

  I have like a bizarrely specific question. I've been on the receiving end of what it's like to communicate with you and your team. It's unlike anything that I've experienced in terms of the speed, the minute.

• 34:06Speaker 02

  The velocity of it?

• 34:07Patrick O'Shaughnessy?

  Yeah, the velocity, like you get engaged and then it's just, you feel like you got plugged into the matrix or something. What is that?

• 34:12Speaker 02

  I don't know. I have no idea.

• 34:13Patrick O'Shaughnessy?

  Can you describe how it works?

• 34:15Speaker 02

  I use the phone. I say this all the time. I use it as a weapon.

• 34:21Speaker 02

  And I have two people working for me and I do now a lot of stuff on AI with regard to conference calls and follow up.

• 34:28Patrick O'Shaughnessy?

  What is your system?

• 34:29Speaker 02

  I have no idea. I just.

• 34:31Patrick O'Shaughnessy?

  You must know.

• 34:32Speaker 02

  I've grown it over years that it's its own animal.

• 34:35Patrick O'Shaughnessy?

  What's the principle behind it?

• 34:37Speaker 02

  Relentless follow up and communication, over communication. I hate it. Like my brother Zeke is horrible at it. He's my eldest brother. I say to him, I just sent you this to call this person because you asked me and I've connected you. And the next call is not that person. What are you doing? I don't understand. And it drives me crazy with my kids too. My middle kid is very good at it, who's in the business, who's in the entertainment because he's seen me do it. But one is you gotta communicate, you gotta over communicate. If they're not getting back to you, you gotta keep on calling them. What are you doing? That's the job.

• 35:09Patrick O'Shaughnessy?

  How do you make people love you for it versus be annoyed by it?

• 35:12Speaker 02

  I don't know if people love me for it, but I try and make it.

• 35:15Patrick O'Shaughnessy?

  At least they respect it.

• 35:16Speaker 02

  I know you want to kill me. You know, you have to bring levity to it, but it is a force. I understand that.

• 35:22Patrick O'Shaughnessy?

  How many calls do you think you do a day?

• 35:23Speaker 02

  A lot. A lot. My friend Pete Berg was in the car with me once. We were coming back. I don't remember. We're coming back from a golf match. And he's sitting in the car and the system starts, the phone calls. And the phone calls can be from President of the United States to a young actor, a writer, an idea I want. And he turns to me in the middle of it and he goes, I'm too anxious right now. I can't breathe. And I'm like, what's the problem? He goes, do you realize what's going on on that thing? And yeah, I know. I'm sorry about it.

• 35:51Patrick O'Shaughnessy?

  It just works. No, I love it. I think it's fantastic.

• 35:54Speaker 02

  Did I come at you pretty hard, my system?

• 35:56Patrick O'Shaughnessy?

  No, it just feels different. It feels like the thing matters. That's nice. Too few things feel like they matter.

• 36:03Speaker 02

  If I'm gonna be involved in something, it matters to me. So therefore I'm gonna take it to the point where I can get it done.

• 36:10Patrick O'Shaughnessy?

  What have you learned from Egon?

• 36:11Speaker 02

  You know, the great thing about him is he continues to want to learn. He's a guy that's made a lot of money. He takes a lot of big risks, but he's smart about them, his calculation. Unlike me, Eminem writes all the time, songs. He writes, writes, writes, writes, writes beforehand. And then when he gets in there, he pulls his. Jay-Z, this is what Rick Rubin told me. He doesn't write any of his lyrics. They're about to start. He comes back in, tune hits, he does the rap. He's instinctual, but incredible. Egon does unbelievable analysis. And I saw it in our take private. I see it when he goes after a company. He's relentless when he wants something. And he takes criticism. For a guy at his level, P E guy, as good as he is, taking criticism and listening to it and absorbing it and then adapting with it. Incredible. I've never seen that.

• 36:55Speaker 02

  Most of these guys, they're alone. Go fuck yourself.

• 36:59Speaker 02

  But he does all those. It's really incredible. And then he learns from it, adapts. I don't know anybody, there are probably people on par with him. I don't know a lot of them. He has a point of view on industries. Like he came after me, he was a tech guy. Here's where I think the business is going, which matched up with mine, content, et cetera. But then the superpower, probably one of the best financial engineers I've ever seen of all these guys. It's not even close.

• 37:25Patrick O'Shaughnessy?

  Defined as knowing what he wants and then building a custom structure.

• 37:28Speaker 02

  When he looks at a balance sheet, he sees a different language than most dudes and sees the value proposition and has been.

• 37:36Patrick O'Shaughnessy?

  Right.

• 37:38Speaker 02

  Not 30% right, 70% right. That's fucking rare.

• 37:42Patrick O'Shaughnessy?

  How do you think about your own investing? That's not one of these massive, major platforms. It's just like a normal investment. How do you do that?

• 37:49Speaker 02

  I got some big investments called TKO. I'm betting on myself. I'm not smart enough now, I have bonds. I'm not smart enough to know, I believe in Elon Musk.

• 37:59Patrick O'Shaughnessy?

  Talk about him a little bit. I know you recently saw some of the robotic stuff. Tell me what your impression was.

• 38:04Speaker 02

  Well, I saw the three or four generations of the hand. I came up to him, I said, I want to do UFC fights with the robots. That's one of the things we started talking about. We just had a fight in China. I sent him to see some of the robots there to see if we could then do a fight.

• 38:15Patrick O'Shaughnessy?

  Chinese versus American?

• 38:16Speaker 02

  Yeah, it was really good.

• 38:17Patrick O'Shaughnessy?

  Wow, everyone in the world would watch that.

• 38:18Speaker 02

  Right? So I went up to see him. The three or four iterations of the hand.

• 38:23Patrick O'Shaughnessy?

  The optimist hand. What did you see?

• 38:26Speaker 02

  Just how much technology was from one to four or one to three, I don't remember, was unbelievable. And what the hand could do, it does what you and I do. And then he showed me a couple of them that could fight and throw punches and kicks and the balance and the pushing, unbelievable. So if I'm a betting man, first of all, if I'm a betting man, I'm betting on that dude. I bet on him on SpaceX, X, XAI, Twitter.

• 38:49Patrick O'Shaughnessy?

  I almost hesitate to ask because everyone knows Elon's awesome and has been awesome and is great at what he does. But how would you describe his greatness? What's your interpretation of it?

• 38:57Speaker 02

  There's nobody like him. I remember it was oh eight. I'm having Thanksgiving at my house with my brother Ram, who's in the Obama administration, who's the chief of staff. Elon's a friend. And we were falling off a cliff. So we're in California. I said, hey, can we come down to see SpaceX and Tesla? Yeah. Now, the president's bailing out car companies. Elon, because I know it, Tesla's in trouble because there's cars backed up that have to be fixed. He's starting a new car company. He's sleeping there like he did at Twitter, SpaceX. He just will not stop, just will not stop until it's fixed. And so, you know, we get in there. He walks with my brother, shows him SpaceX. This is at the beginning, oh eight.

• 39:38Patrick O'Shaughnessy?

  Yeah, nothing.

• 39:39Speaker 02

  Nothing SpaceX. He's building it. But he was sleeping there on two hours sleep. He needs that in his life, even though he hates it at times. Because I remember him calling me and he was so upset with Tesla and what should he do with it? And we would have conversations. But he wills things with sheer brains and power and guts and endurance to make them, right? And that's his superpower. Because it gives, in a weird way, even though it's, I think, emotionally brutal on him, taking all the punches and feeling that, it also does give him a huge amount of energy and emotion satisfaction.

• 40:14Patrick O'Shaughnessy?

  You've got this show called Rushmore, which is about greatness. What is it about greatness?

• 40:18Speaker 02

  I don't believe in legacy. You know, I don't believe that business people have legacies. I think Elon will have a legacy. I think Jeff Bezos will have a legacy. I think Steve Jobs has a legacy. Probably mostly it's presidents, leaders, maybe some actors. But if you asked a person on the street, Lucille Ball. You wouldn't know. But I do think there's characteristics of those four people that are important to know about. Like, how did they get there? And are there patterns? And as we just said, we just did a Rushmore on the 90s of music with Jimmy Iovine and Rick Rubin, who are two guys that should be as producers on Rushmore, in my opinion. And Rick Rubin talks about how Eminem, he constantly writes his lyrics. He's writing all the time.

• 40:57Patrick O'Shaughnessy?

  Yeah, two different kinds.

• 40:58Speaker 02

  And Jay-Z doesn't. No, there's a lot of ways to get to the top. And I think one of the things I always talk about, we as humans, we can at least see greatness in how they do it and then adapt it or learn something there and take that learning and keep on evolving. But I think it's always important to learn from history, as it rhymes, and then take things and use them in your own life, and that's why I'm doing it.

• 41:22Patrick O'Shaughnessy?

  What have you learned about, with a life like the one you've led, it's not lacking adventure, how to talk to your kids about it? And not create a circumstance where there's a expectation?

• 41:33Speaker 02

  I got a daughter that works at the WWE. I got a son that's working for Rick Caruso, hopefully not, he runs for governor. And then my son is in the business. He's a producer. And the other one works at Apple. And they have had unbelievable luxury. I think if you ask people, I hope if you ask people, they're pretty normal kids. Because, one, they weren't overprogrammed. I wasn't a helicopter father. Their mother wasn't a helicopter mother. The summers, they ran around in Rhode Island and played golf and played tennis. And if they did stupid shit, they got punished. And they didn't run our lives. So they're pretty normal kids. And I'm not sitting there trying to always help them. I make an introduction and then it's their job. Even though they hate, they would tell you. My eldest son, Noah, it's one of my favorite moments.

• 42:17Speaker 02

  We're flying somewhere and he goes, "I just want to be normal." I said, "Who the fuck wants to be normal? Normal sucks." And I said, "What the fuck is normal? Normal, what is that? I don't even know what that is."

• 42:29Patrick O'Shaughnessy?

  People say a lot of things, mostly amazing about you. One of the things everyone says is that you're one of the consummate dealmakers. What is a great deal? In your mind, some of you agree, you've made a lot of great deals. What is a great deal? What is a great process of deal making?

• 42:43Speaker 02

  You know, when you're making a deal, and they're all different, people have said this, both sides have to feel good. Your job is to make sure the other side, whether it's true or not, feels good.

• 42:54Patrick O'Shaughnessy?

  Simple.

• 42:55Speaker 02

  That's not easy.

• 42:56Patrick O'Shaughnessy?

  How do you do that? What's the art of that?

• 42:58Speaker 02

  There's so much nuance to that. Sometimes, certain people, it's just a fight. You're just aggressive. Like, okay, we're in a battle. Certain people and certain negotiations, and everybody feels as you're in a dance. And you're trying to get them, and you just have to hang in there and do the dance till we get to the end of the song. And it's not a battle. I mean, I've been in screaming matches, like, okay, fuck you. I know you need it. You know I need it. We're firing guns. We're shooting. So I like the second one better. And that's just about charm. And that's just about how you have to play. Sometimes you gotta get mad. It takes time. Somebody was asking me, what's the art? It is so complicated.

• 43:32Patrick O'Shaughnessy?

  Yeah, it can't be reduced.

• 43:34Speaker 02

  I don't know if it can be reduced. That's when I was constantly on the field. I was always the first one. I was always shooting. I was always in a fight. As I've gotten bigger, there's a lot more dancing. I was a pretty ugly fighter, though. I mean, I was just constantly angry, pissed off. And you're standing in the way of where, because I've already played the chess match out. If I get this, this, and this, then here's what happens. You're standing in the way of my chess match. And so I'd be pissed.

• 44:01Patrick O'Shaughnessy?

  Seemed to work, though. I like the extremes. What's the fastest money you've ever made? And what's the longest game you've ever had to play?

• 44:09Speaker 02

  The greatest deal I ever made was quote unquote merging with William Morris. Forty-four million dollars. Paid out the CFO and Jim Wyatt. They never thought we were gonna write a check for twenty million dollars and have the votes to fire them. Patrick Weitzel and I did that, got the deal done and the merger done, I think in a year. And they had a horrible culture, so everybody hated each other. And we just played the chess match on their side. And then took over the company and brought in Silver Lake.

• 44:34Patrick O'Shaughnessy?

  Rest is history.

• 44:35Speaker 02

  And that then led to everything.

• 44:37Patrick O'Shaughnessy?

  So just to zoom in on that negotiation a little bit.

• 44:40Speaker 02

  So here's what happened. They were in trouble.

• 44:42Patrick O'Shaughnessy?

  Financially?

• 44:43Speaker 02

  They just were losing clients and financially in trouble, and they all hated each other, and they knew they didn't have good leadership. And we could just keep on putting out bad press on them and taking agents and taking clients. It took seven years to do that. And then we just pitted board members against them and brought them on our side. Because we actually treated them well. We actually did. And then when the vote came, before the merger, you guys now have to get rid of Jim Wyatt because he's a disaster. And the CFO, all their hands went up because they realized, wait a second, these guys are good guys. And we were. So even before the merger closed, they got rid of them, and then it just all happened. And then that led to Egon coming into my life. Teddy had gotten sick and passed away. Teddy Forstmann going after IMG. And it was the best deal I've ever made.

• 45:26Patrick O'Shaughnessy?

  What was that flip like from agent to owner?

• 45:29Speaker 02

  This is where Egon was a great teacher. He helped us think through because we knew we were going after IMG. And then, once we had IMG, I knew instinctually, Patrick took over the college football business that they had. And I moved to the UK and I took over IMG. And that's how we split the baby. And nobody was telling me I had to move to the UK. I just realized, basically, and I just spent 2.4 billion dollars. You better fucking get your ass to the UK and understand that business. And none of those people wanted to stay because they didn't want us to win. IMG didn't want us to win. They wanted somebody else to win. They wanted Chernin's group to win. And this is where I learned a lot from Egon in this conversation. He says, I think that Chernin, they were going to pay, I think it was 1.9 billion. And he said, we're paying 2.4. I said, 2.4? Why don't we pay 2.1? He goes, we're going to make it so they can't say no and they can't go back.

• 46:14Speaker 02

  Because they don't want us. And he was 100% right. Pay 2.4, we get it. And then I realized, this is my money. Time to move. Family stayed in Rhode Island and LA. I moved for, I think it was four or five months.

• 46:27Patrick O'Shaughnessy?

  To the UK.

• 46:28Speaker 02

  And all over Europe. I went to Spain for our tennis business. All over, learned all the players. That's another place. When I got done, I was physically

• 46:36Patrick O'Shaughnessy?

  Fried.

• 46:36Speaker 02

  Fried. Because I was then flying back on weekends and it was crazy. And then I represented writers, directors, actors. Plus, I had to do that. So that was when it all happened.

• 46:45Patrick O'Shaughnessy?

  Do you care about money anymore? Are you motivated by money?

• 46:48Speaker 02

  I didn't really care about money since my first show went into syndication. When King of Hill went into syndication.

• 46:53Patrick O'Shaughnessy?

  What happened then?

• 46:54Speaker 02

  I was making 15 cents a mile. When you're making 15 cents a mile and then all of a sudden, you can go look at the math. It was $6 million an episode and they did 14 seasons. You're okay.

• 47:04Patrick O'Shaughnessy?

  So then, if money sunsetted, what became the thing?

• 47:07Speaker 02

  I want to be right. My ideas, I want to make sure that they're right.

• 47:10Patrick O'Shaughnessy?

  Because that feels good? Simple as that?

• 47:12Speaker 02

  I'm not the stupidest Emmanuel. I still have competition with those two.

• 47:18Patrick O'Shaughnessy?

  What have you learned from Ram?

• 47:19Speaker 02

  When you talk to my brother Ram about politics, and you can talk to him about a lot of other things, but when it comes to his metier, and we're not talking about just domestic politics. We're talking about global politics, how to handle allies in Asia to combat China, or what to do on Israel, or any subtext. I'm going to boast about my brother Ram. When you look at the potential field of potential candidates for presidents, and there's Gretchen Whitmore I know. I know Josh. I know a lot of these guys, and they're all very qualified on a global basis. And he is as relentless and as driven as I am in what I do. Was in two White Houses, was the whip in Congress, was a mayor of a big city, and understands everything going on in one of the biggest, most important areas

• 48:04Speaker 02

  in the world for us, Asia, and had galvanized, and his responsibility as ambassador, galvanized that region to combat China. There's nobody more qualified. Whether that makes him a future candidate, I have no idea. But my brother understands. It used to be when you were CEO is just bilateral. Now it's multilateral. I don't think anybody looks at that board better than him in politics and in global issues. And he learned from incredible people. Bill Clinton was incredible. Obama was incredible. Worked out their agenda. At details, you can ask him about the Supreme Court in Pennsylvania issues and how they handle that. He's at an inch. I'm at an inch in my business. He's at an inch. And he understands then what that means for the congressional races, what that means for the Senate, the messaging that you have to do and how to stay on message.

• 48:49Speaker 02

  And Zeke, he is just hysterical. I mean, I love him. He's a bioethicist. I think he's incredible thinking about medicine, and he loves it. So I just love him.

• 48:59Patrick O'Shaughnessy?

  What happens when you're no longer at the one-inch level? When you are no longer deep in the flow?

• 49:05Speaker 02

  Well, I'm not now at William Morris.

• 49:07Patrick O'Shaughnessy?

  Has that been easy?

• 49:08Speaker 02

  I just said this to one of the companies that I run, Barrett-Jackson, and Craig Jackson wants to step back. And I said to him, you know, you're never stepping back. He goes, what are you talking about? I said, well, here's what I did. Let's go private. Richard White and Christian Mayer are going to take over the business. And they're going to do some really great things. And they're going to fuck shit up. And you know, the only way they're going to learn?

• 49:28Patrick O'Shaughnessy?

  By doing those two things.

• 49:30Speaker 02

  By fucking shit up. You don't really learn that much for doing good things. And I said, and you've got to permit the fuck ups. And the problem is, I said, I started my business 31 years ago. It's my name. Your father started your business and now it's your name. You just won't let anybody fuck up. What's the worst thing that could happen if it fucks up? Is the business going away? No, so let them fuck up. That thought process, not a lot of people have that run companies.

• 49:52Patrick O'Shaughnessy?

  What was your most formative fuck up? The thing you fucked up that taught you the most?

• 49:56Speaker 02

  Well, I fuck up all the time. Thank God Mark Shapiro's in my life and Egon's in my life. I think the biggest fuck up, truly, because we're building the business and you pick bad people. But we had a bad meeting, Patrick and I, Weitzel, with Irv Weintraub, Jim Wyatt, and Dave Warshafter. And I went nuts. I was playing the chess match out and they didn't let me get to the end. And I actually went talking about the negotiation. I screamed at them. We're sitting at a table like this at the Beverly Hills Hotel. I went nuts. I said, you don't know what the fuck you're talking about. We could buy you. We're two inches big and it's William Morris. Because we were more profitable. And I said, you know, nothing about business. And I go fucking nuts. And Patrick, to his credit, he knows when I hit the DEFCON four or five, he just get the fuck out of the way. Meeting ends, it's over. And we're walking down Wilshire. And he goes, well, that's over.

• 50:40Speaker 02

  I said, no, it's not over. This is happening. A year and a half later, two years later, it was back on the table. But that was a fuck up because it just pushed us way, way back. But I just, I thought DEFCON, I was so pissed.

• 50:51Patrick O'Shaughnessy?

  What do you think the future of TV and movies are?

• 50:53Speaker 02

  There's going to be a lot more of them. And I actually think what I said to you. I think that you're seeing it now. Marketing companies are going to podcasters and streamers and marketing with them or giving them brands and giving them ownership to sponsor them and market them. And sometimes they sponsor them and sometimes they ask them to take equity. And same thing is going to happen with content. We talked about this. I think the cost is going to go down to zero or very close. And Dwayne Johnson, Mark Wahlberg, Dana White, Pat McAfee, they're all going to become their own channels. I do believe actually, I don't know if that's in two years or in seven years. So then, representation has to change its infrastructure, like we changed when we took over sports, to be able to handle that conversation with regard to licensing, marketing, all that stuff.

• 51:37Patrick O'Shaughnessy?

  Give me advice. I have a channel. I have a lot of people.

• 51:41Speaker 02

  I think the podcasting business is going to become like the cable business. It's going to become like Oprah.

• 51:45Patrick O'Shaughnessy?

  What does that mean?

• 51:46Speaker 02

  Oprah had Dr. Phil, she sponsored people and then she took them out into syndication on the station groups. You're going to find a young you and maybe it's in medicine or maybe it's in something that interests you and you're going to bring them into the fold with your sponsors, your distribution and everything. You're going to take a piece of it and maybe there's a product that comes off of it and you're going to own a piece and he's going to own a piece. And then you're going to figure out, maybe I need my own sponsorship marketing team internally. So you're going to become, you're Oprah. You've become Oprah.

• 52:15Patrick O'Shaughnessy?

  Great.

• 52:16Speaker 02

  That will be the first iteration of this. You never know. You might find a movie that you like or a document or you like and you send it out to your subs. And then there's multiple ways you can monetize that. Maybe you turn that into a book.

• 52:29Patrick O'Shaughnessy?

  Play the game.

• 52:30Speaker 02

  That's my opinion.

• 52:31Patrick O'Shaughnessy?

  What's your craziest view on the future of sports? We'll finish where we started.

• 52:34Speaker 02

  Prices are going way up.

• 52:36Patrick O'Shaughnessy?

  Prices for everything?

• 52:37Speaker 02

  Prices for teams.

• 52:39Patrick O'Shaughnessy?

  Okay, talk about that because like in the NFL, everyone's like, there's no more rich guys to buy the teams.

• 52:43Speaker 02

  Well, they'll just change. They'll go from P firms owning 10%.

• 52:47Patrick O'Shaughnessy?

  To own 50 or?

• 52:48Speaker 02

  35. And instead of they can only take a billion dollars a debt out, they can take $2 billion.

• 52:53Patrick O'Shaughnessy?

  It'll just go up.

• 52:53Speaker 02

  That shit will change. But the price of sports for the end user is going to be more. Therefore then, there's going to be tiers at Netflix, which the sports tier, you pay $15 and they're going to have to make a decision, when do they go direct? It depends.

• 53:07Patrick O'Shaughnessy?

  The leagues.

• 53:08Speaker 02

  Yeah. It depends on when this thing caps out. We just saw a big input of money, which is betting. That market will increase and the amount of money they pay will increase. Premium ticket will go up and ticketing will go up.

• 53:20Patrick O'Shaughnessy?

  Prices are going up.

• 53:21Speaker 02

  Price going up.

• 53:22Patrick O'Shaughnessy?

  What do you think of gambling? What do you think of betting?

• 53:24Speaker 02

  Well, I think it's good actually in the following way. For us, I'm just talking about our businesses. The more data, the more you can't cheat. And I think what's going to happen, you'll have an AI company come in and look at all the data and you're going to understand, you're going to triangulate and understand there's something happening over here with this picture and you're going to look at video and it's going to be like, So it'll be harder to cheat. Not that people won't try. I think it helps actually the engagement. Now, do I think gambling is good is a different conversation.

• 53:55Patrick O'Shaughnessy?

  Do you?

• 53:56Speaker 02

  I don't gamble. Do I think gambling is good? You know how I come at you hard? Imagine what I do to my kids on gambling, health, smoking and drinking. I feel bad for my children. Unrelenting articles, conversation. It's horrible, but that's the job of being a parent.

• 54:15Patrick O'Shaughnessy?

  When you see the layer of massive technology companies, you talk to all these guys all the time. I'm sure. What's your impression of what's going on in big tech at large?

• 54:23Speaker 02

  So here's my understanding with Sam. Sam has made a trillion, two in obligations.

• 54:29Patrick O'Shaughnessy?

  It's a big number, whatever it is.

• 54:31Speaker 02

  He has 800 million subs. Let's just say he does 14 billion in revenue, probably lose 5 billion. Do you understand it? I'm definitely not as smart as you or any of these investors. They must see something. And the only way it pays off, unless I'm wrong. Now, George Gilder would scream at me. He goes, every technology has created more jobs. This is the only technology at this level of spend, you have to be taking jobs and jobs have to go away. And then the government's going to have to pick them up and we're going to be more efficient. And I don't understand the math. I'm not smart enough to understand the math. You know what I do know? How to put on a fight and put on an event. That's what I know.

• 55:04Patrick O'Shaughnessy?

  Who is the person that you represent or have represented? That's the most innovative in this landscape right now. You mentioned Dwayne The Rock Johnson. He seems pretty damn innovative.

• 55:11Speaker 02

  They're all testing new. Kim Kardashian is, Mark Wahlberg is, Dwayne Johnson is. They're all looking at it and figuring out how to play in it. Not all of them. Aaron Sorkin isn't, Larry David isn't, but they're just great creators. Marty Scorsese isn't. He's just a great creator, but there's some actors, writers, directors that are looking at it and trying to figure out where they sit in it. And I think the first thing they all have to do, they have to start playing with it and they're all starting to play with it.

• 55:38Patrick O'Shaughnessy?

  What has you most worried about the future and most excited?

• 55:41Speaker 02

  Do you have kids?

• 55:42Patrick O'Shaughnessy?

  Yeah.

• 55:43Speaker 02

  I'm worried for my kids.

• 55:44Patrick O'Shaughnessy?

  Why?

• 55:45Speaker 02

  I didn't tell you this. So I'm sitting there, I'm having my normal every six month meeting, lunch, dinner with Elon. And we're talking about AI. He said this to me, he goes, life cannot be disrupted. I said, okay.

• 55:58Speaker 02

  I have two ears. So we're talking about AI and he goes to me, all right, do you have a dog? I said, yeah, well, here's AI. AI is you and you're the dog. I said, I don't like that. He goes, that's what's happening. That's gonna happen. Well, you and I have kids. I haven't figured out, which, you know, as a parent, we have to think about where my kids sit. That makes me nervous because I'm like, I'm over the hill. In four months, I'm 65. Who gives a shit about me? I have 30 year olds. I have a 23 year old that works at Apple. I've heard him speak about his kids. That's hard. What are we telling them? What are they supposed to be doing?

• 56:33Patrick O'Shaughnessy?

  What do you think the answer to that is?

• 56:34Speaker 02

  I don't know. I actually don't know.

• 56:36Patrick O'Shaughnessy?

  Do you have a guess?

• 56:37Speaker 02

  No, I don't. Do you? You talk to a lot of people. What are they saying to you?

• 56:41Patrick O'Shaughnessy?

  Create things, make things.

• 56:43Speaker 02

  Ideas.

• 56:44Patrick O'Shaughnessy?

  Use the tools, make new things.

• 56:45Speaker 02

  Yeah.

• 56:46Patrick O'Shaughnessy?

  So far, these things are gonna make everything.

• 56:48Speaker 02

  And I'm not sure. I know everybody's saying it's coming very fast. There's a numerator and a denominator here in the United States. I think it's just us in China, really. But I don't know if it's the numerator or the denominator. But there's this thing called energy and energy delivery that I'm not sure yet is there for it to be in the next, at full AGI capacity.

• 57:12Patrick O'Shaughnessy?

  Meaning literally the power?

• 57:13Speaker 02

  The power.

• 57:14Patrick O'Shaughnessy?

  Yeah.

• 57:14Speaker 02

  And also how we deliver the power.

• 57:17Patrick O'Shaughnessy?

  So a big problem to solve. Could take a while.

• 57:19Speaker 02

  It's gonna take a while. So we have a little bit of time, but we have to still be thinking, what the fuck are we telling our kids?

• 57:26Patrick O'Shaughnessy?

  What about what's most exciting?

• 57:27Speaker 02

  Most exciting for me? I've started this new business called Mari, trying to make that into the next Live Nation there in music or build this new company, having learned, because I'm not a PE firm, but I'm a company, but I've learned all these different skillsets.

• 57:44Patrick O'Shaughnessy?

  Why do that one separately than the original company with UFC?

• 57:48Speaker 02

  Because Silver Lake just wanted Endeavor to be an agency. So he was, one, selling down the events and a bunch of other assets that we wanted to buy at TKO to pay down the debt. And live is where I wanted to be. So I was like, fuck it, I'll just raise a bunch of money. And the good thing is, which I felt really good about, I actually did feel really good, this crazy idea I had, people like saying, yeah, you're right. So now I want to make them a lot of money, which I've done for a lot of people. Now I'll make myself a lot more money. Not that I care, but.

• 58:14Patrick O'Shaughnessy?

  But you want to be right.

• 58:15Speaker 02

  No, but I want to be right. It is a benchmark and these people should make a lot of money because I want them to. That's the most exciting thing.

• 58:22Patrick O'Shaughnessy?

  I know you love art. What has the world of art taught you?

• 58:25Speaker 02

  Well, you know, I have a very specific area of art I collect.

• 58:28Patrick O'Shaughnessy?

  Which is what?

• 58:30Speaker 02

  I collect African-American artists, mainly American, but now Africa and other places. From about 1940 to now.

• 58:40Patrick O'Shaughnessy?

  Why that?

• 58:41Speaker 02

  I don't know, it just spoke to me. I have no idea why. So it was from Sam Gilliam, Bob Thompson, to Kair Walker, Mark Bradford, to Noah Davis, he passed away, incredible artist. And I just, I love it. And I've been doing it now for 17 years, 18 years, in this specific area. And so I'm just deep and unrelenting.

• 59:03Patrick O'Shaughnessy?

  Shocked, shocking.

• 59:04Speaker 02

  Yeah.

• 59:06Patrick O'Shaughnessy?

  Long live. My favorite question is my last one that I ask everybody. What is the kindest thing that anyone's ever done for you?

• 59:12Speaker 02

  The kindest thing anybody's ever given me is trust. Clients trust me with their biggest dreams. Crazy. When Tyler Perry comes to me and says, here's what I want to do, or Marty, or Larry David, or... That's an incredible gift of kindness. And then same thing with Egon backing my play multiple times. And then I would just say to you, I have now in my life, a great life. I never realized it before. I was just on the field. And I have a great second wife, Sarah Stoudamire, who's got a great fashion business, Stod. And I think I have great brothers, but I have four incredible kids. And that, I'm a lucky guy. I love them and they love me. And as your kids get older, it's crazy to

• 59:55Speaker 02

  have these conversations with these things that are now adults. And they say to you and do things that are just beyond your imagination. And it is the nicest thing to see that happen in your life. From a kid, from me, that they didn't think I was supposed to go to college. And that this life has happened for me. And my parents were incredible. All those things collectively are the kindness that has happened. And there's plenty of times I was not deserving of it. I definitely was not, because I didn't realize how you're supposed to act and get off the field.

• 1:00:32Patrick O'Shaughnessy?

  I absolutely love talking to you. I love your energy.

• 1:00:35Speaker 02

  Thank you.

• 1:00:35Patrick O'Shaughnessy?

  I love how you approach the world. You're so distinct and interesting. Thank you so much for your time.

• 1:00:41Speaker 02

  I really appreciate you.

• 1:00:43Patrick O'Shaughnessy?

  If you enjoyed this episode, visit joincolossus.com where you'll find every episode of this podcast complete with hand-edited transcripts. You can also subscribe to Colossus Review, our quarterly print, digital, and private audio publication featuring in-depth profiles of the founders, investors, and companies that we admire most. Learn more at joincolossus.com/subscribe.