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Funny, when you go to these NBA meetings, there's 30 billionaires sitting around a table and they've got their heads down like they'd be in a classroom. Yeah, and they're all worried about the commissioner picking on them.
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Today I'm speaking with Dan Gilbert. He's a self made billionaire and NBA team owner. He's also the story of how when you think you have it all, it's no guarantee. In the last decade Dan suffered a significant stroke as well as family tragedy. We're going to talk about all of that and what he learned. But first I'm going to troll him wearing orange and blue. And I realized I'm not fully ready. Dan.
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I'm not going anywhere. Dan.
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I brought this.
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Oh, very cool.
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Are you gonna be okay if I wear this the whole time?
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Semi. Okay.
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Come on, Dan.
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I'm kidding you. Come on.
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This is what I do on the show. I invite NBA owners and then I troll them by wearing Nick's stuff.
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Who else did you have besides Mark?
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Just Mark and you so far. Who should I have next?
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Those are the only two good ones
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you don't think I should have on Matt Ishbia?
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Probably not.
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Smart girl Dumb questions. I'm Nae Ma Raza. This is Smart girl dumb. And today my guest and very good sport is the owner of the Cleveland Cavaliers, who in case you missed it, were swept by the New York Knicks
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after we gave away game one.
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That was what happened in the Eastern Conference finals. Did it soften the blow to see how well the Knicks played in the finals?
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Never softens the blow when you get swept. So. But I was, I was sort of rooting for them because I like the east over the west because we're from the East.
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Yeah. So you were.
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Oh, you're rooting for the next again, San Antonio?
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Yes, it's a very qualified Rutin, but I heard that Jim Dolan threatened to ban you or relegate you to the cheap seats. Did you hear this?
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I heard something like that, but I don't. I think it's just a bunch of nonsense.
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Can I show you the clip of it?
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Sure.
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I love NBA owner drama. So this is Fat Joe. Do you know who Fat Joe is?
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Yeah, I know who he is.
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Yeah. Okay, so he's out here.
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I was in Cleveland and I bought courtside and this is a real story.
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And they took it away when they
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knew it was fat Joe Gates. Ms. Do is so busy sitting. There we go, game five, putting the
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owner up the deck.
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Well, what really happened was it wasn't just him. So we put in a policy that our front row seats could not sell their seats. I mean, that was even from earlier in the season.
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So anybody who owns courtside seats for Cleveland Cavalier games in Cleveland could not sell their seats to anyone else in Fat Joe bought them, presumably on the market. And you denied him the seat?
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Well, I don't think we denied him. I think they probably weren't able to sell it to him.
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Jim Dolan said that he would send you to the deck.
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Yeah.
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Do you buy that?
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He could, but, you know, we could do the same thing.
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Do NBA owners do that to each other?
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Not that I know of.
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Yeah. Would you have sold the ticket to Travis Kelce and Taylor Swift now that you know that Taylor Swift is a Knicks fan.
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Do we know she's a Knicks fan?
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She wore that Knicks outfit. She sat courtside in New York.
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She did in New York because she came to the Cavs games. I think she was wearing Cav stuff.
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I think she said she claims she's a Knicks fan. Okay, well, while he owns the Cavs, Dan is really a Detroit man, not a Cleveland man. Correct. You are extremely successful as an entrepreneur. You made billions building rocket companies. Rocket mortgages, Rocket loans. It was called Rock before, right?
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It was in the old days, yes. Rock Financial, actually. Rock Financial built at Quicken Intuit, actually. Oh, Intuit owns the Quicken products.
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Okay. And then it became Quicken Loans.
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Correct.
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How much did it sell for originally?
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Yeah, I think it was. This is. We're going back to year 2000. It might have been before you were born. No, I wish it was all stock for stock deal. But I think it turned out when you did the numbers, it'd be about 500 million. But then we bought it back two years later for a lot less. So that was good.
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And then you've built it into businesses on top of businesses, and you've made billions doing this.
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I didn't know how to bring my financial statement here.
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You didn't have to, Dan. But then you poured billions into developing Detroit, right? Something like 7.5 billion, something like that, Yep. Why?
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Well, first of all, I was born there. I was raised there the first five years. Then I moved to a close by suburb. But you know, when you lived through Detroit, it was 50 or 60 years of a kind of a downswing, if you will. And I witnessed it all, or most of it anyway. And I just always said to myself, if I could do something about it and help bring the city back, I would.
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Today we're going to Talk about the role that billionaires can play in rebuilding cities if we should really rely on the rich to do that. I want to talk to you about what the USA might learn from the MBA and what it's like to be an owner. But really, we're just going to talk about a lot of things because I'm
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here, I'm not going anywhere. Whatever you want to talk about.
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One of the things I like about a couple years ago at Masters of Scale, I was interviewing Dan and the
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mayor of Detroit, Mike Duggan.
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Mike Duggan, the other mayor.
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Yeah.
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And before, they were like, there are all these things that you can't ask Dan. Do you know this?
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No, I don't know that.
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I wanted to play a clip of Donald Trump trolling Detroit because remember what he said about Detroit?
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Yeah, yeah. That was in Detroit. I think Kamala. It's not gonna be high on her list. I don't think anything that we're talking about today is high on her list. The whole country's gonna be like, you wanna know the truth? It'll be like Detroit. Our whole country will end up being like Detroit. If she's your president, you're gonna have a mess on your handshakes.
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And I wanted to play that tape for you on stage. And they were like, you can't. Dan doesn't wanna talk about politics or whatever. And then I saw Dan. I remember. I said, your team doesn't want me to ask you about Trump. And you said, I'm a big boy. You can ask me anything.
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Yep.
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Which is the way. Which. I like that.
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Good. But only you.
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Only me. Thank you. You also were very nice and told me that I could be like Oprah.
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Yeah. Can people cry? I guess. Huh?
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Oh, I'm not. Hopefully I don't do that.
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Yeah, don't do that today. Good.
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And the compliment meant a lot to me because I learned that you had had your own podcast.
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I do, but it stopped a few years ago.
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But we had the first. We had the same first guest, Mark Cuban.
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Mark Cuban, correct.
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He popped both our podcast cherries.
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Yeah, he's. People do that with him.
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Yeah, he's a good first guest.
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Yes.
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And I wanted to play the tape of that. We have a little tape.
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Done your research.
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And this is in 2019. He has just signed the one that would later get away. Luka.
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I mean, I'm looking around. Everybody's jaw is, like, dropping. Because it's not that he's just scoring a lot, it's that he does everything.
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Yeah.
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He's confident he's just confident player. But I mean, he can drop dimes, he can shoot the three, he can shoot mid range, he finishes well, he plays some defense when he wants to.
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But I have a dumb question. What is dropping dimes?
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That's an assist, an assistant.
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Okay. What other terms do you think? I don't know. From the NBA and other performative Knicks fans? Don't know.
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You know, it's funny, cause I've asked people for many years, why isn't a CIS called a dime?
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Yeah, why is that?
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I can't get an answer for that.
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Dropping dimes. Did you see our guy, Jalen Brunson? He started, you know, they were covering him so hard, he just started dropping dimes.
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Yeah, he did. That's what he did. You're already using it.
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I'm using it in a sentence. You were a really good podcaster.
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You think so?
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I think you were good.
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Can I be a guest host for you one day?
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Sure. Billionaires are just like us. They also want to host podcasts. Why did you do it?
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I don't know. Just. I always liked the mic, I guess. And we had a lot of good people coming through Detroit these days.
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And you had Karlie Kloss on. That was one of your episodes. And then you stopped it in spring of 2019.
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Yeah, I had the stroke in the spring of 19.
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Totally unexpected, right?
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Yes.
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What happened?
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Oh, they really don't know. Totally. They think it's genetic. There was some clot that got cut into, if you think of like a fork in the road. So my arteries had a fork in the road they called a tortious artery. And some maybe skin peels off the inside of an artery and it just blocked the blood flow.
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Did you know what was happening when it was happening?
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Yeah, it really didn't even happen, technically, until I got to the hospital.
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Really.
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I was in an apartment, downtown Detroit. There was only two physical signs I had which aren't the normal signs of a stroke. My left hand became very cramped up and then I had like double vision. That's not the normal. Like, there's an acronym called fast. I forget what it stands for. Arms, speech, and time, meaning get your butt to the hospital. The first three are.
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Okay, so face, arms, speech, and time is what you'll see. Your face, your arms, and your speech get disrupted.
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If you think someone's having a stroke, that's very important for everybody to remember that.
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Yeah, that's actually very useful.
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So if their face starts drooping, if their arms. You hold your arms out, they start Falling. If their speech is hard, then you gotta get to the hospital. Time, beat the clock. I mean, 30% of the people who have a stroke like I do die on the spot. And after five years, only 30% are alive. And I didn't die two years ago, so I'm still here.
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So I don't think you're going anywhere anytime soon.
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I hope not.
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I hope not.
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I hope not. So, you know, you start learning when you have things like this, you actually feel lucky because of how much worse things could be.
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Yeah.
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I mean, a stroke on the other side. My stroke was on the right side of my brain, so it affected my left side, and I'm a righty, but if you had it on the other side, I would have taken out the right side and I was righty. And also when you have it on that side of your brain, it affects your speech. So my speech never got affected from it. Can you understand me still?
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I can understand you very well. I understood when you were saying you love the Knicks. That's what you're saying, right?
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You know, you're too nice to pull things like that off.
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No, I wouldn't do that. How is it moving through the world being as powerful as you are and also having this condition, which is limiting.
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It is limiting and it's sobering. And it's. You know, it's still shocking to me. You wake up days and I go, I can't believe I'm doing this. But all you can do when you have a condition like this is put one foot in front of the other and just keep going. And I'm fortunate enough to have. I put people around me that are helping me.
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Yeah. So I think for people in life, it's also like, I felt this with my dad when he was getting older as well, and he passed away a few years ago. But it's like, it's actually a privilege to help to take care of people in life. It's like we forget that. And I think so much of our conversation around caretaking is like, oh, it's a burden, and it's this. But actually, it's like a great gift to.
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For some people, it is a burden, but for others, they understand they get a lot out of it.
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And it makes you feel lucky also, everyone around. But you certainly put one foot in front of the other. Cause you had the stroke Memorial Day. And by early the next year, by like Q1 of 2020, you were back at work.
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Yes.
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Was that important to you, just like, getting back? Yeah.
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I mean, I would go Two to three days. And then the other days. I'm rehabbing still now. Oh, yes.
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You're rehabbing three days a week now?
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Yes.
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And what, is there gonna be a cure, you think, or.
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Well, I'm actually in a trial this summer. There's a company that has had some success with a peptide for people who've had spinal cord injury, and they want to try it on stroke victims. So I'm going to be in their trial, so I'm excited about that.
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That's great. But speaking of getting back to it, I want to talk about the NBA for a minute, and we'll come back to that. You and Mark, obviously, Mark Cuban, really get along.
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Love, Mark. We always kidding around. We wanted to have the all AVS finals.
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Oh, you did?
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Cavs versus Mavs. Never happened, but maybe one day, who knows?
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What percentage of league owners do you actually like?
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Great question. I would say more now than I used to. When you're the new guy. I mean, you know, they. They aren't as nice as they are to the older guys. Now I'm becoming one of the older guys.
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So when did you buy the Cavs?
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2005.
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And last year you had it, like, evaluated for a potential sale, right? Like you were gonna sell 15% potentially.
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And we still worked. I think we're actually in the process of selling 5 or 10% right now.
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Who are you sell.
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I can't remember. I really can't.
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You really can't remember who you're selling?
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It was. I think it's a.
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How much money do you have, dad? You can't remember?
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It's a private equity firm.
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I think it's a private equity firm.
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You know, they're getting into sports a lot, some of these private equity firms.
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What's that going to do? Is that just going to drive up the value of all these teams?
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Well, it sort of has done that to. To the. To a degree already, both in the NFL and the NBA and in Premier
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League, I think also in, like, soccer and everything as well.
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Yeah. Are you going to the games here?
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I did. I went this past weekend to Brazil, Morocco. It was a bit of. They let it tie.
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Well, that's what soccer is. I think that's one of the reasons that soccer hasn't boomed in the United States like people thought it would, because I think Americans like scoring.
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What percentage of NBA owners do you not like? Maybe that's an easier one to answer.
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Well, I'd say I like the majority of them. There really are very few that I would say that I don't like. Most of them are pretty good guys, nice people.
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Are there rivalries? It seems like, you know Jim Dolan saying, oh, you know, I'm gonna move him to the dad.
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That sounds like. That's the first time I really heard that. I think he's just doing a little. Your guy there was doing a little grandstanding.
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My guy? Fat Joe?
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Yeah.
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Not my guy.
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He's not your guy.
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Not my guy. You famously, like, had a less than perfect relationship with the previous Commissioner of the NBA, Mr. David Stern.
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I think it was pretty good relate. It was an average relationship. David was a phenomenal commissioner for 30 years. I mean, he built that league.
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Yeah.
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But he also too. He used to pick on Mark. He used to pick on me. He picked on the new guys.
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He picked on you?
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Oh, yeah.
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How'd he pick on you?
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You know, it's funny, when you go to these NBA meetings, owner's meetings, there's 30 billionaires sitting around a table, and they've got their heads down like they'd be in a classroom.
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Yeah.
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And they're all worried about the commissioner picking on them.
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That's how I. This is what I think it's like. Adam Silver has the most epic job in the world, but is he technically your boss? Because you and Mark actually talked about this. And I'm gonna play you. Cause you're not gonna remember this conversation from 2019.
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I told our boss, I think. Is he our boss?
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Kinda.
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Yeah, actually, he works for us.
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But that.
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Yeah, but that doesn't really. That's a patient. Right. So Adam Silver, I said to, you know, I said, adam, put the lottery. Put that out publicly in live tub so people don't have doubts. Cause it's. There's no.
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So you're talking about Adam Silver here. What kind of grade would you give him?
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I give him an A minus. I think he's really good.
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Why the minus?
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Cause you always gotta have something to go for.
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Okay, so better grade than David's turn?
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I think similar.
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Really?
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I mean, they're very different. Very different styles.
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What's the difference in their styles?
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I mean, David Stern's more of a rough and tough kind of guy. Curmudgeoning. Is that a word?
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Yeah. Curmudgeonly. Yeah, for sure.
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And Adam's more of a. Like a statesman. Yeah, he's a diplomat, but they're both great.
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What's the relationship between these billionaire boys sitting. Mostly boys sitting around a table, looking a little scared.
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Employee of the owners.
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Exactly. But it doesn't feel that way.
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Huh? No. But he's still the boss. Yes.
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What are the characteristics of someone that's good at getting billionaires to do what they want or need?
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Well, I think you've got to stand up to them when you need to, which they both do. I mean, you saw what Adam did to the former Clippers owner, made him sell the team based on those kind of racist like remarks.
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Oh, yeah. Oh yeah. That was ages ago.
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Not that long. Probably 10, 12 years.
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Yeah, 10 years. Yeah, I remember that.
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Yeah. I mean, it was actually on tape somewhere. It wasn't like he went out and made him. But. But you can't make racist remarks when you're an owner in an NBA league. That's.
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So you thought it was the right decision?
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85% African American. I mean, it was. Yes. I mean, the players weren't gonna play for him, which I don't blame him.
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Yeah.
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Based on what remarks came up. So Adam led the vote that made him actually sell his team. So that was a big statement for him to make. And that's not easy to do.
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You gotta push em when they need it. So these billionaire boys around the table respect someone who pushes them.
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They do. And you gotta make the tough decisions like he made. And there's other ones he's made too that are very tough.
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Such as?
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Well, some of the labor negotiations with the players union. He had to make some tough decisions there, which I think were fair but tough.
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On the China stuff he's had to answer for, engage with. You think he's doing a good job there?
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Yes.
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When I look at the NBA, I see a model for something that is very much about fairness. You know, there's basically, there's salary caps, there's some revenue sharing, there's a lottery, and then the rest of the draft goes according to like the team that did worst gets the best player.
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Yes.
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So there's a lot of leveling of the playing field and making things fair.
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There is.
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And some owners, like I asked Mark this question too. It's like, can the USA learn from the NBA? And Mark said, well, that's socialism. And he was joking. He said that's what Jim Dolan, daddy Jim Dolan, not the son, would say that the NBA was socialist. Do you think the NBA is socialist?
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No, I don't think it's socialist. But you have. Since it's one league, I mean, everybody considers themselves partners with each other and that's what keeps it together. Because if one guy goes off the reservation like the guy in LA did, it really makes the whole League look really, really bad. So the owners themselves kind of clamp down on that when that happens because they know it affects them. So there's a built in, kind of like behave yourself connotation, if you will.
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Yeah. So everyone can disagree. But when it comes down to it, the league is more important than anyone.
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You gotta behave yourself.
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Which is like wild because these are people who have been extremely successful, who have not small egos and they are falling in line with.
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They do with his greater. As long as you have that strong commissioner.
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Yeah. Do you think that the USA like our approach to the world of like.
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I think the problem there is the equivalent for a government to do it. You'd have to almost own all the big companies in America.
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Yeah.
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Or you'd have some form of an alliance. Because the NBA works. Because if everybody was completely independent, let's say you had these independent teams that just joined a league, that would be a different story.
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Seems to be highly coordinated and as Mark pointed out, exclusionary too. It's like not everybody gets a team, not everybody gets to be at the table. But do you think there's a lot we could learn in terms of leveling the playing field a bit?
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I think that the collective bargaining agreement, which, if you can imagine it's not just so you have NBA billionaire owners, but you also have extremely wealthy players now. I mean, and they get over 50% of all revenue, top line revenue, it gets split between the players. And so that's. They're the biggest partner of all.
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Do you think they're more powerful than the owners?
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I think it's gotten that way, yes. And that's recent, I'd say in the last 10, 15 years. Yes.
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Is that a good thing?
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Well, it. It makes sense. I mean, they're the talent, they're the league. But some people would say you can't have too much because it's hard to corral it all in when there's 450 players and 30 owners.
B
Yeah. There's also like all of these. Like, there's all these rules around what you can and cannot. You know, like, I would love to ask you if LeBron James is going to come home to the Cleveland Cavs, but you can't comment on that until after June 30th.
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Correct. Because you've done your work.
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Yeah.
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Yep.
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You don't want to give me anything, I presume.
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I can't. I wish I could, you know, for you I would, but I can't.
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On June 30, you're going to call me and give me something.
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Of course.
B
Okay. That would be good. There's all these rules of things you can and can't do, but there's all these questions around people trying to get around, like the salary caps. There's a big conversation with Steve Ballmer right now.
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That's right.
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There's an allegation that they got around a salary cap for Kawhi Leonard by offering a sponsorship package from a company that Steve had invested in.
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Right. Obviously, once you start going down that road, then it really comes off. The wheels start coming off, so you can't do that.
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Do you have thoughts on that particular.
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Well, I don't know a lot of detail about that, but you can't. You can't. If any of that is. Is true or close to true. It's. Yeah, it's got to be dealt with. Because once one team starts doing it, then all the teams start doing it, then you don't really have a collective bargaining agreement anymore.
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And what does dealing with it mean?
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There's gotta be penalty. There's gonna be penalties for him and his team.
B
Yeah.
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Whether or not they void that contract, whether or not he loses draft picks. It's happened before.
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When did it happen?
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It happened with Minnesota's owner several years later. Ago, before I even got joined the league.
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What happened?
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He lost three draft picks for something that I can't even remember exactly.
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Oh, that's. Yeah, that's one of the penalties. They lose the draft picks. Have you ever been fined, like Mark Cuban likes to get fined?
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Oh, yes, I've been fined.
B
Yeah. What did you do to get fined?
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We got fined recently. The franchise got fined for. We didn't play two or three of our star players during a national game towards the end of the season because, you know, that's the other thing. Teams start resting their players as they get near the playoffs.
B
Oh. And you have to play them so that it's there certain rules.
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Right.
B
Wow. Do you know all the rules we have?
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You know, each team has, they hire what they call a capologist.
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A capologist.
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Can you believe it?
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Is that like the Moneyball guy in the movie?
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It kind of is. It's like. Cause it is very complex.
B
Yeah.
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And the Klecker bargain agreement, it hasn't been over just. It's been built up over 25 years, probably. So there always gets new negotiations and new rules. And there's rules on trading. There's rules on everything.
B
You famously wrote a letter to LeBron James. Can we talk about it?
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Do I have to?
B
You have to.
A
Okay. Sure.
B
Do you need more water, by the way?
A
No, I'm good.
B
Okay.
A
Better take a sip, though.
B
Yeah, you definitely want a sip now. So LeBron James had played with you guys for a long time?
A
Yeah, seven years at that point. Yep.
B
And then he went off. He was a free agent.
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Yes.
B
Went off to the Miami Heat.
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Correct.
B
You wrote a very strongly worded letter.
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Yes.
B
I'm not gonna make you read it. No, but it had, you know, talked about betrayal, and it was.
A
Well, what happened was, remember he went on national television, did a show about it, about where he was gonna go play next.
B
Yeah. Is that where you found out, though?
A
Yes.
B
You found out when he announced it?
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Yes. They never told us in advance.
B
And so you were pissed.
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Yeah, we were not happy with it. And I thought it kind of trolled the Cleveland fans, who I loved. My letter wasn't to him. My letter was to the Cleveland fans.
B
It was a letter to the fans.
A
Yeah, it was stupid. Overall, if I had another shot at doing it, I would have toned it way down.
B
What would you have said instead?
A
I don't know. I just said some things in there that I shouldn't have said. I can't remember the specifics, but I can.
B
But I'm not gonna make it.
A
You can tell me later.
B
I'll tell you later. But you were tough on LeBron. You called him the self named King.
A
Yeah.
B
You know, you gave him some heat. What were you thinking? Was that you doing it? Did some intern draft that letter? That was it.
A
Actually, Drew, you should have seen the first version on.
B
Really?
A
No, I'm kidding.
B
Wait, did you have other people read this letter?
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No, I had one or two people, but they didn't tell me what they should have told me.
B
Who were one or two people? Your brother?
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No, one of the PR people, really. But I can't. I think maybe my ex wife read it.
B
Okay, so two people read it. And did they? Were you counseled not to put this letter out?
A
I mean, they brought it up. You may want to consider not doing it, but I was in a state.
B
Who do you think is more scary? A Swiftie fan? Cause I noticed you didn't want to really comment on Taylor. Taylor Swift there. You was more scared of swifties or of LeBron Stans?
A
Probably Swifties. People in Cleveland loved the letter. Everywhere outside of Cleveland, they hated the letter, which I guess I understand.
B
So your fans liked it. Four years later, you take it down. I think it went down from the website.
A
Right. And we were negotiating with LeBron to come back, which he Did.
B
And he did come back. And then he won the playoff championship.
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Sorry, 2016.
B
Yes, 2016.
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Yep. Which was the first time in 52 years that Cleveland won anything.
B
So it was like this moment for the Knicks.
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Yes.
B
It's the first championship in 52 years,
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except it was for all teams, not just basketball.
B
Wow. For all teams in Cleveland.
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Yes.
B
How did two such strong personalities as Dan Gilbert, owner of the Cleveland Cavs, mega billionaire, business owner, operator, and LeBron James have that kind of fallen out and then make it work again?
A
Well, I flew to Miami, where he was with two or three of his advisors, and we had a couple hour meeting. And I think it was. At the end of the day, it was in both of our interests to do this because he wanted to come back. He wanted to come back home, and we're the only place he can do that. And we definitely wanted him. We felt that it would work well.
B
Yeah.
A
So I think if you're both mutually on the same mission, it can work out.
B
Did you have, like a. Did you prep for going into that meeting? Did you have a sense of what you were gonna say, or do you just, like, play it?
A
I'm sure I prepped it a little bit.
B
Did you apologize early on or before
A
the meeting about the letter?
B
Yeah, yeah.
A
I mean, I admitted that the letter was a stupid thing. And for me personally, it was like, at that time, people who just. If you googled my name, I mean, I think I've done some other stuff in my career and that'd be the only thing that comes up. I mean, that was embarrassing for me. So.
B
Yeah, it was also the whole conversation around. It was around the font choice of the letter.
A
Yeah, yeah. That was another thing.
B
Comic Sans.
A
What was weird is I had somebody on my team, just as a joke, I think the week or two before, changed my font to Comic Sans.
B
What was your original font going to be?
A
It was probably Times New Roman or something. So it happened. It wasn't changed just for that letter. It was changed weeks ahead of that.
B
So everything was changed and was a yes. Okay. So you're not a Comic Sans enthusiast?
A
No, I got as much heat for that than the whole letter.
B
I know.
A
Next time I'm calling you.
B
Yeah, tell me. I mean, you gotta make a public apology for the use of Comic Sans, it turns out even more than.
A
Why do people hate it so much, by the way? They just. They do. There's like a visceral hate for it.
B
It's so funny. I was thinking about it. I think it's because it was like the font we used in elementary school. It was one of my favorite fonts. I liked Comic Sans. But it's not a font to be taken seriously. No, it's so if you. I mean, it almost is. Like, if someone had put out that letter in the year of 2026, I think it would have. It's the kind of thing that would have gone on Twitter and everyone would be like, is this real? Cause it's such a joke.
A
Yeah. What's your favorite font?
B
I like Montserrat.
A
I gotta look at that.
B
This is what it looks like.
A
Let's see.
B
It's like. It's this. See, you're gonna see my questions, Dan, this is what you're doing. Let's see. That's what it looks like.
A
Good font. I'm not answering that question.
B
How's your relationship now with LeBron? You guys still.
A
I think it's fine. I mean, we don't see each other that much. I mean, he works in California. I work in Detroit and Cleveland. Yeah, he came to a game or two last year.
B
Yeah. Was it hard for you to watch, like, so in the game before the Eastern Conference finals.
A
It was game seven.
B
It was game seven, and it was the Cleveland Cavaliers and the Detroit Pistons.
A
Right.
B
And you're a Detroit guy.
A
That's right.
B
Was it a hard game for you?
A
I mean, it's like if you had two kids playing each other in a basketball game or something.
B
Yeah.
A
I mean, I would say the Pistons are my second favorite team.
B
Okay. Who's your least favorite team?
A
I don't. I don't know if I have a least favorite one.
B
Oh, you must. You can choose by owner.
A
Well, after the Knicks swept us, I'd have to put them up there.
B
Oh, really?
A
Maybe that's just sour grapes on my purpose.
B
That might be sour grapes. I would think you put Phoenix, maybe.
A
No, No. I don't pay attention to them.
B
They're not even in your league. Okay. Can we watch some game tape?
A
Sure.
B
Okay, here's some tape of this Game seven.
A
Yep.
B
This is Cavs.
A
Pistons, Pistons. Two seconds. One second.
B
Mitchell banks it in
A
a spider bite
B
at the end of the quarter. Great.
A
Of any of the matchups. Oh, Mobley, big finish. And this topsy turvy series belongs to Cleveland. Well, that was the peak.
B
That was peak.
A
Everything from there kind of went downhill as we started playing the Knicks.
B
And this is what happened next. I think this is game three with the Knicks banks at home.
A
And this is the largest lead of the game. Cavs still have plenty of time with five and a half remaining. And that's what I'm doing right there. If I'm the Cavs, get the ball out of his hands at all costs. Look, you're going to give something up. Johnson gets free fakes, goes inside, lays it up and in. The Cavs just stopped playing on that possession. They stopped playing the possession before that.
B
They stopped playing the possession before that. How are you feeling when you're watching this?
A
Well, you know, you watch it, you're. You're just a fan, really. Even though you own the team, you're just a fan. And it's. I mean, the Knicks were a steamroller when we. When we caught them.
B
Yeah.
A
So you got to give them credit. They really put. They had their best year in 53 years. Bronson's just a. He's a beast.
B
And it's so sweet to see him and his dad. Yeah, he must like that.
A
I do like it, but he's a special player. I mean, he always has been. But this year especially, he's so smart. Yeah.
B
Like how he uses his eyes to distract people. You never know where he's going. It's like, it's a wonder to watch him.
A
I mean, he does almost everything on the court.
B
Yeah, he's really.
A
And he's a good leader, too.
B
Yeah. Why do you think he's a good leader?
A
I mean, you could just. Just his body language when he's talking to other players. You could just see the other guys respect him, at least from my view.
B
Yeah. And so when you're watching, like, you know, your guys are getting swept. We were talking and I was like, oh, I wonder if there's gonna be a game five. You said there's definitely gonna be a game five.
A
Yeah.
B
No Game five.
A
No Game five.
B
Who are you most mad at? Cause as a fan, you're mad.
A
Well, what hurt us in that specific series was game one in New York. And here you are, Game one in New York. That sets the whole tone. It's an away game, and we had a 22 point lead, seven minutes and lost it. That was the series right there. You're not coming back from that. And we didn't really.
B
That's a series.
A
Yeah.
B
So you think if they had played first in Cavs territory in Cleveland.
A
I'm just saying if we had won that game on the road, Game one, it would have been a whole different series? I'm not saying we would have won it, but it would have been a much different series.
B
So what happens? Like, the energy of the team the motivation, like what, actually having watched this so closely.
A
Well, I think it was more the Knicks than us. I mean, Knicks just were hitting every shot they were taking. They were playing together. They were coached really well. Which is also former coach of ours, Mike Brown.
B
I know.
A
In fact, we were the first team to hire him as a head coach.
B
Do you want to hire him again?
A
Well, we can't do that now.
B
Can't do that now. You were not mad. What's the emotion that's happening?
A
Yeah, you get mad, you get frustrated, you go through it all.
B
But not mad enough to draw a technical.
A
No, I don't think they're giving me one.
B
No, that's because they like you. I think you're well liked in the league is what I sometimes is what I can understand. Do you think of the team as a business?
A
Yes.
B
And is it a good money making business?
A
Well, it's funny because pro sports teams are like art pieces. There's only so many of them in the world.
B
Yeah.
A
And they tend to keep going up in value. They're not so great as a cash flow business.
B
They're kind of like a vanity investment. Right.
A
I would say that like buying into a restaurant. I call it my biggest hobby.
B
Your biggest hobby?
A
It's a hobby.
B
Is it your favorite hobby?
A
Yes, most of the time.
B
And it's really bonding for you and your kids. Yes. They love the Cavs too.
A
Oh, they do, yes,
B
but it's not. But it's a business. I mean, you're gonna sell. If you sell 5 to 10% stake to a private equity company, that's probably gonna be valued at a good chunk of change, right?
A
It'll be valued pretty good. Yep.
B
How much did you buy the Cavs for?
A
$375 million in 2005.
B
$375 million. And how much are they worth right now? Do you have any sense of.
A
Well, I mean, Forest comes out with a report every year.
B
I think it was around 5 billion.
A
Close to that, yeah.
B
Okay.
A
That's over 21 or 22 years. 21 years.
B
Is that a good ROI?
A
Probably, yeah.
B
So it's a good business.
A
Yeah. Well, it's valuable.
B
It's a great hobby.
A
Yes.
B
None of my hobbies are making me, you know, 10x plus. We'll take a quick break and be right back. I want to move on from basketball.
A
Good.
B
Let's go and talk to you on June 30th when you can say more. I think he's coming back. You can't say anything, but I think he's coming back home.
A
You do?
B
Yeah. Everyone wants to go home at the end. Yeah, right. There's no better place to be. But I want to talk about Detroit. Sure, let's talk your other love. So two and a half hours bus ride the other way.
A
Correct.
B
When you were growing up in Detroit, what was it like? Were you in the city property?
A
Well, the first five years I was. I was born there, but I lived just a couple miles outside the border. Remember the movie 8 mile?
B
Yeah.
A
So I was like at 10 mile, an 11 mile.
B
You know Eminem?
A
Yes, he came. Eminem just performed at our all company meeting.
B
Oh, really? How was he?
A
He was great.
B
Yeah? Yeah, he's great. I love that movie, 8 mile.
A
Yep. It's the border of Detroit and the suburbs for the most part. Three. Yeah.
B
And did you come from like, I'm just gonna ask very directly, did you come from like a rich family?
A
My dad owned a bar in Detroit.
B
Yeah. So no.
A
So no.
B
And did you have any imagination that your life would end up where it has ended up?
A
I mean, I always wanted to be in business, even growing up. I love business. But you never know where you're gonna be. Business is such an open canvas. Anything can happen, right?
B
Yeah. So you grew up in Detroit. 10th mile, you end up going to Michigan State.
A
Yes.
B
Go green.
A
Yes.
B
And what point did you. How many companies did you try before you built rock?
A
I delivered pizzas for a while in college and right after. But that's not a business that counts.
B
The business.
A
I think I have a record, though.
B
You have a record?
A
People don't know about it, but what's your record? 78 deliveries in one evening.
B
78 deliveries in one evening.
A
Like when pizza guy comes to my house now.
B
Yeah.
A
I always ask him, what's your record? And they're like, they're like in the 40s, low 50s, like 45, 52. I go, I used to do what you do. 78. And they'll look at me and they go, oh, you're him.
B
Really? What's the pizza place?
A
It was called Papa Romanos.
B
It still exists?
A
Yes.
B
And you still deliver from them? I still do order from them. I mean.
A
Yes.
B
I always think of the TV series HBO Succession, which I think most smart girl, dumb questions people would think of. You haven't seen that? You haven't seen Succession?
A
I saw a couple episodes. The guy was so mean that I couldn't watch it.
B
The father was so mean.
A
Yep.
B
And you're not like that. You have a really good relationship with your children?
A
Yes, I Do.
B
Why do you think we see the world like that? We want to see billionaires like that.
A
Well, billionaires and corporations are the only two, I guess, things you're allowed to hate these days, right?
B
I think you can like hate religion, wokeism. Well, I don't know. I think there's so many things that we, I think, but we are in the business of hating everything. But I do think there's, there is a galvanization, particularly what everything we saw with the killing of the United Healthcare CEO Ryan Thomas in New York City and the kind of fervor for his alleged killer, Luigi Mancioni. People hate health insurance. I think you're very much allowed to hate your health insurance. I think that there is a sense that like billionaires are like there's a real wealth division in this country and around the world that we haven't seen as much recently. And like we're seeing it. Do you think it's dangerous right now?
A
Well, I think if it keeps going in the same direction, it's probably not healthy overall. But that doesn't mean that, I mean, does it mean that the billionaires have too much or does it mean that we need to figure out a way that the middle class can have more wealth?
B
What do you think?
A
Yeah, I think it's the latter.
B
You don't think the billionaires have too much?
A
I mean, how can you say what's too much? Somebody's a painter. What if they make great paintings and they're all over their house? Can we walk in there and say they've got too many great paintings?
B
What about Elon Musk becoming a trillionaire? Do you think that's too much?
A
I think the question's a weird question. Not again, I don't want to say
B
dumb question, but I think that it's simplified. But I think in that case it's a really interesting one because Tesla had so many government grants that were given and then obviously Elon has created, I think Elon has created a great company in Tesla and that company's obviously been extremely successful. He obviously is a very clear vision for the world and for humans becoming a multi planetary space faring civilization. But I do think there's a question of whether people should be taxed at higher rates or like when the government makes such grants. American taxpayers should have some ownership. I mean Trump is doing this now
A
with some of these companies. I agree with you like that. I do like that.
B
So you think taxpayers, when governments get subsidies or.
A
Yeah. They shouldn't just give away.
B
Yeah.
A
Who does that Right. If you're a government, if you're gonna give. That's what the Chinese and the Russians do, I think.
B
Yeah. I mean, even there, they've got capitalism too. I think it's very. It's capitalism. Well branded. But you, like, you are not, I don't think, hated as a billionaire. I think you're very beloved, especially in Detroit, right?
A
Well, in Detroit, yes.
B
Are you. I mean, everybody else, they have their Comic Sans problems. And these days there's a lot of rift sometimes between government and billionaires. Sometimes you'd say there's not enough rift. Like Andrew Ross Sorkin said that after everything that went down in Minnesota. Minnesota. And he gave a kind of talking to, saying it's time for business leaders to stand up to the president when it comes to certain policies. But you and. You and the Detroit government have had a very good relationship.
A
Yes, we have. I mean, since we got there, we. We really met with everybody. The city, the state, the county, community groups, the police. We met with everybody. We all wanted to get everybody in the same boat, rowing the same way. That's really the only way you can really bring back a city. I mean, everybody's gotta be in the same boat, rowing the same way.
B
And when I interviewed you and Mayor Mike Duggan, previous mayor of Detroit in California. In California two years ago, you guys had like a great rapport. Yeah, he was like, this guy doesn't stop texting me with ideas of what to do with my city, basically. Right?
A
Yes.
B
And you're still friends?
A
Yes. You know, he just dropped out of the governor race, unfortunately. Yeah, I saw that he was running as an independent. This was gonna be the. The big thing for American politics. Cause if he won as an independent, as the governor, maybe other people would do the same thing, but you can't. It was tough.
B
I really liked you guys report. I wanna play, actually a minute of it, which is I asked you guys about a Politico piece that was written about America's top mayors. In 2017, Politico published this piece on America's 11 most interesting mayors. Mayor Pete, now secretary Mayor Pete Buttigieg was on the list. Eric Garcetti from Los Angeles was on the list. And you, Dan Gilbert, were on the list. They called you the shadow mayor.
A
Well, that's because I walked behind him every day.
B
Is it a fair characterization?
A
Well, not with the great mayor that we have, it's not.
B
Yeah, I mean, they mentioned, of course, Mike Duggan as well.
A
But what number was he? Not the top 11.
B
Number 11, but is it A fair characterization. I mean, look, we talk about billionaires owning things like the media, Twitter, et cetera. So that conversation, I mean, it was really interesting how you guys reacted to that. You had a good sense of humor about it. Mike Duggan was not on the list. He was mentioned. He was mentioned in the paragraph about you. But do you think of yourself as like a mayor of Detroit?
A
No, not really.
B
Not really means something. Not really means something.
A
I mean, he was. And what I said there, he was such a good mayor for so many reasons. First of all, he became the mayor. I don't know if you know this, when he ran, he made a mistake and didn't file the signatures in time. So he had to run as a write in candidate.
B
Oh, yeah, I did know that.
A
So this is a 85% African American city. Here's a white guy named Mike Duggan running on a write in ballot. And what the other Democrats did is they found another Mike Duggan who's a barber, and they got him to run as well to confuse everybody. And he still won.
B
And he still won, which I think
A
is really a feather in the cap of America that you don't. We're not all black and white, if
B
you will, you know, and then you guys had a great rapport. You worked together very collaboratively for a long time. Detroit has a new mayor now.
A
Yes. Mary Sheffield.
B
Yes. You shadowing her too?
A
Well, I interviewed her in front of my whole company the same time that Eminem did the concert.
B
Okay. How was that?
A
It was nice. I mean, I like her. Her heart's in the right place and we're trying to support her as best we can. I think she's gonna do good stuff
B
in New York City. Right now. We have our mayor.
A
What's his name again?
B
Zoran Mamdani. You know his name?
A
I really don't.
B
How do you not know Zora Memdani's name?
A
I've heard the name. I don't know how to pronounce it.
B
I feel like everyone in America knows this guy's name. How do you like how he's. Have you seen how he's. How Trump. Have you seen Donald Trump's bromance with Zoramdani?
A
See his what?
B
Bromance between Zoran and Donald Trump.
A
I've not seen that. I saw the Ken Griffin thing.
B
Yes. So Zahra Ahdani and Ken Griffin.
A
Yeah. They don't like each other, right?
B
They do not. Mehrmadani did a video where he was outside at Ken Griffin's house. It looks like he's looking through his peephole, and it was to announce a pied a terre tax outside of the most expensive apartment in New York, which happens to belong to.
A
Wait, what was he announcing? Say it again.
B
A pied a terre tax.
A
What does that mean?
B
You should have many pied a terres.
A
I don't know what that means.
B
It's like, it's French for a place you stay on the weekends, basically. So a home you don't primarily live in.
A
Oh, so it's higher property tax for those.
B
Yeah. So he wanted to introduce a higher property tax for all the people who kind of keep up real estate in New York, but do not, are not in New York full time and are not living in that. So he wanted to announce that Kevin Griffin was pissed. I mean, Ken Griffin really hasn't engaged in this conversation directly with the mayor. And the mayor has, I think, made some indications that he would want to talk to Ken Griffin. But I think he's kind of burnt a bridge is what it looks like from the outside. What do you think? Smart move is a dumb move.
A
I think that what politicians sometimes forget tax is a price. I mean, when you raise the price of something, you get less of it. So when you try to say that you're gonna have rent controls or things like that, that means you're gonna get less houses or less apartments. So you really should be promoting policies that creates. If you need supply, let's have policies that create supply. That's ultimately gonna bring the price down.
B
Right, but you're not anti tax.
A
No, I'm not anti tax, but I would rather see strategic policies that promote the solution versus just like it's punitive.
B
Yeah. I think the critique that was leveled against the mayor was kind of. Ken Griffin is a billionaire who contributes to New York City. He may not live here, but Citadel is still incorporated here. He donates to a number of philanthropic organizations.
A
I mean, we would doing an $8 billion, and we'd love to move him to downtown Detroit.
B
So, you know, you reached out to Ken and ask him?
A
No, I have not yet.
B
Have you spoken to him about this at all?
A
No, I haven't. I met him once about three years ago, maybe four years ago.
B
Yeah. But there is this, like, tension. I think there's also an incentive for people to irk each other and for that to become content.
A
Right.
B
Because it's like, you know, it cuts both ways. I think extremely successful business people can talk all about the incompetence of government as a way to ingratiate themselves More with the public talk about how successful they are, how inept government is. And then on the other side, you can have government kind of pointing fingers at these people who don't pay enough taxes or whatever they would say, and don't contribute enough to society or live in average life.
A
I think with billionaires and people who are like. When you talk about trillionaires like Elon, I think you gotta wait till the end of the day to make a judgment. I mean, look at Bill Gates. I mean, remember years and years ago, people. Cause he was so wealthy relative at the time. For not just the US but for the world.
B
Yeah.
A
Probably the most charitable person that's ever walked the face of the planet.
B
Do you think that that charity, though, could like. Do you really buy the argument? That's always better when it's done by the private sector, having worked so closely with the public sector.
A
Now when anything's done by the.
B
Yeah.
A
Well, there's obviously certain things that you have to have the public do. The police, the military, roads. I mean, there are things that are definite roles for government. But. And I'm not. What happens is you get a broad brush on both sides, people. One thing happens on the other side of something they don't like, and they take a broad brush on and go, see, look at all those billionaires.
B
I think.
A
Or the opposite. The mayor does one thing you don't like. See, look at all these politicians. That's the problem as Americans, we take out the broad brush way too much and we use it for everything.
B
Yeah. I agree with that. I think what's happening in America right now is people don't understand why their lives are tough.
A
Yeah.
B
And there's a lot of scapegoats out there and a lot of people who would like you to blame one person or another, be it the wealthy, et cetera. I do think. And Andrew Ross Sorkin made this point to me too, like that it's when you look at, like Mike Bloomberg or Bill Gates, they're all in their older years of life. And so maybe these Mark Zuckerbergs and, you know, I mean, Elon's kind of. He's not. Elon's no spring chicken, but like, maybe they're.
A
He's in his 50s. Right.
B
He's in his 50s. But I think this idea that, like, okay, you're gonna put everything into the Zuckerberg Chan foundation or Elon Musk foundation or whatever it is, and then the money will just trickle back into the system through the initiatives of these individuals. It means that A lot of things don't actually get done or people can pick their favorite causes and there's other stuff that doesn't get addressed.
A
I wish you could say that about anything, though. You know, it's Buffett and Gates came out with the Giving Pledge, which I signed. I think it's 110 or 115 billionaires have signed that now, but what a great idea that was. So that means you're making a pledge that upon your death, at least 50% of your wealth, at least most people are higher than that. I'm higher than that.
B
Would you ever sign such a pledge? This is a dumb question. Would you ever sign such a pledge to give 50% of your wealth to the US government?
A
No, definitely not.
B
Because.
A
Because I don't know. I wouldn't. I would think private foundations, like you said earlier, or answer your question earlier, are going to get way more done than a large bureaucracy.
B
Do you think that if government had more resources, it would get more done? Like, I mean, in Detroit, you've kind of proven that to some extent.
A
Yeah, but that, that took getting everybody, as I was saying earlier, in the same boat. I think that smaller is better when it comes to government.
B
Yeah. Those are your politics.
A
Yes.
B
It's really hard because for me, it's a little chicken and egg thing where I've spent a lot of my life also living in places like Europe where if you keep on neutering government, government will never be effective. So it kind of like, it's a fait accompli. It's like, okay, government's so incompetent. And then worse people go into government like it just, it's a sinking ship. And I think your experience in Detroit has shown like, it's like if you can make people proud of the work that they're doing in government, you get better people. Government can do better. And it's like a rising tide lifts all boats, right?
A
And somebody's gotta lead. So sometimes you will get a dynamic, charismatic guy leading, like I think Mike Duggan was.
B
And you think this next mayor will be.
A
I think she is. I think she's very good.
B
Do you think there should be a path to become a billionaire in government? Lil Cliffhanger. We'll be right back.
A
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Your call has been forwarded to voicemail.
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B
Do you think there should be a path to become a billionaire in government? Like, if you're really good at your job in government office, you should be able to make a lot more money.
A
I think there's certain jobs that we should probably pay more in government. I don't know how you do a path to a billionaire in government.
B
Yeah, well, right now what happens? Like people don't get paid enough, then they go out and they post their government life. They're basically trying to make money by working at all these companies that they supposedly regulated when they were in government. And that revolving doors.
A
Wealth is created. People forget that wealth is created by human beings. It's not just a pie every year that's produced and you split it.
B
Yeah, certainly not. You create wealth, but government is doing a lot that creates wealth too, right?
A
Well, yes, and I think you said you touched on one important point. How do we attract the best and brightest to government jobs? Because it's even for people that run for president. I mean, look, does that look like an attractive job for anybody?
B
Well, Donald Trump seemed to have wanted it over and over and he could have just been a billionaire. Yeah, but I think it is an attractive.
A
He's the rare case.
B
I think it's a vanity job. Like owning a sports team is a vanity investment. Yeah, I mean, it could be a public service job, but I think for some people it's a vanity play.
A
I mean, can you imagine if there was Naima deranged syndrome? I mean, that's a pretty big deterrent.
B
What's your relationship like with the president right now?
A
I mean, I know him well, not real well, but I know him over
B
the course of time.
A
Yes.
B
You're not investing, you're not donating to the ballroom.
A
No, I don't really comment on political things.
B
I know you don't comment on that. But he likes his name on things.
A
He does.
B
He likes Trump rx, he likes Michael Dell's doing these Trump accounts. A lot of business leaders right now are not enthused about a lot of the policies when it comes to, like, tariffs or this war. There's a lot of economic policy that is challenging. Does it affect your businesses?
A
Well, our StockX business, the tariffs really affected it.
B
And StockX is.
A
StockX is what we call the stock market of things. Sneakers has been our big product, but we basically. It's like the NASDAQ of things, and we authenticate and verify the products.
B
Okay.
A
Our position on it. This is a typical thing with bureaucracy. Right. So when the shoes were made originally, if they were made in China, they'd be a tariff when they come in. So if I sell them to you next, should there be another tariff paid?
B
Should there be? What did you think?
A
Of course not.
B
Yeah.
A
That's what we're trying to fight.
B
And so are you up? Are you in a conversation or are you involved in.
A
I mean, we've got some people working on it yet.
B
Yeah. And do you find that the president is receptive to feedback from the private sector?
A
I think he is.
B
It seems like right now. I mean, a lot of. You've seen this with Jamie Dimon and Davos, You've seen this with Tim Cook at Apple, Andrew Ross Sorkin called this out on cnbc. That a lot of business leaders feel like right now they can't say much when it comes to politics. They can say less than they used to. Do you think that feels right?
A
It doesn't feel right if you can't in America say what you want to say. But I understand it. I mean, we're so divisive right now that you say one thing, one side hates you, the other side doesn't.
B
Yeah. Yeah. I'm sure there's a backlash of the public. And then there's also the concern of offending this president in particular, who has a. Who has a desire for not liking that.
A
Yeah.
B
But I know you don't like to talk about politics. Does that predate Donald Trump or do you always not like to talk politics outside of local politics?
A
Outside of local politics, I don't really think it's my place.
B
Yeah. Although you would never run for actual mayor.
A
Maybe the mayor. That'd be about it.
B
Would you actually run for mayor?
A
Just because I think you could get a lot done locally.
B
Mm. But would you like that job, like the day to day of taking those meetings?
A
I don't know if I'd like it. I got a lot of meetings I don't like to take now, too.
B
So I hope this isn't one of them.
A
No, this is. I'm loving this meeting.
B
Okay, good. Are you. You would actually run for mayor?
A
I used to kid around with my family that that would be the ultimate job.
B
Yeah. And why didn't you?
A
Because we were getting a lot done without me being mayor and we had such a great mayor. I didn't need to.
B
Now you gotta get that, like, you know, from the 8th to the 10th mile. Dan, maybe you gotta take the seat.
A
We'll see.
B
Would they want you to do.
A
Only if you're my campaign manager.
B
I don't think you want a journalist as a campaign manager. That's so interesting that you would not rule out running for mayor. What about president?
A
No, that's not. These days.
B
That's a terrible. I don't know if it's a job that you'd want. What about governor?
A
It's say that I couldn't see it
B
right now if the.
A
I mean, the only ones you could feel like you could get stuff done is probably mayor, governor, or president. Right. If you're part of a big body.
B
Oh, God. Being a senator or congress person, I mean, that just seems like a lot of.
A
That's a horrible job.
B
It's a tough job. But we do have to get better people. I think we have to get better and better people. And I think also there's like a push towards getting more young people into government, which is probably a good thing. Would you be. What are your kids gonna do?
A
Well, two of them work with me right now. My daughter's a psychologist and my other son is. He's in Miami in a startup business.
B
And you don't have a succession plan like the TV show succession?
A
No. And I'm nicer than the main guy there.
B
Yeah. Brian Cox. He does a fantastic job. I think your kids are also more competent than the kids that are played there. I sure hope one of them at the end, I'll ruin it for you, says he would like the whole company and he says I'm the eldest boy and it's like a total temper tantrum. That, of course, is modeled, I think, to some extent off the movie.
A
Does he end up passing it on by the end of the series?
B
Oh, it's a really fucked up ending.
A
Is it? Should I really watch it?
B
You should actually watch it. You should do a Dan Gilbert watch party where you have 78 pizzas delivered an hour. Hang tight for a second. We'll be right back, guys. Today's sponsor, Dumb Question is from me. I'm going to take the next minute to Tell you a little bit about smart girl, dumb questions and to ask you for your help in continuing to make independent, fact based and curious journalism. No, I'm not going to ask you for money. Here's what I need. I would love you to tell 10 of your friends about the show or 100, I don't know. Blast that reunion group that you muted. And definitely tell your mom and tell your mom to tell her friends too, even if you don't like the show and you're just like hate watching it or listening to it. Tell 10 of your friends to hate watch it too. Numbers are numbers, people. Good sleep is everything. That's why Ollie's science back support is made with a blend of melatonin and L theanine for both kiddos and grownups. So when your mind won't switch off, you've got something that can help your racing thoughts and restless nights won't stand a chance. Find Ollie Sleep solutions for the whole family@ollie.com, that's O L L Y dot com. In 2019, you had a stroke and a few years later you had something probably even worse that felt even worse happen to you.
A
Yes.
B
Which is that you lost your son.
A
Correct.
B
Nick. Nick had a rare disease.
A
Yeah. Neurofibromatosis called NF. So that's one out of 2,500 people in the world are born with a genetic condition. But when there's 8 billion people, that's still 2 million people in the world who have this.
B
Yeah. And you have five kids.
A
Correct.
B
And Nick is what birth order?
A
He was the oldest.
B
He was the oldest. And you found that diagnosis out?
A
He was 15 months old because he
B
had these spots, you said they're called
A
cafe au lait spots, which are like coffee with cream on your skin. And that's a sign of it. Pediatrician found it, and when she told us, we never heard of it. And when I talked to any NF family, nobody's ever heard of it. Plenty of other rare diseases are just even rarer than that.
B
And Nick became a huge personality in everything that you did.
A
He did.
B
What was his prognosis like when they told you the diagnosis? What was the expectation with that?
A
First of all, the word neurofibromatosis means tumors on the nerve. So tumors can grow on the nerves anytime, anywhere.
B
Okay.
A
And sometimes people are covered in these things. Sometimes people just have one or two. Some people are walking around the world, they don't even know they have it.
B
They don't even know they have it.
A
Right. So it's very Very wide manifestations. And his were in his brain, unfortunately.
B
And his were in his brain.
A
So he had multiple brain surgeries and chemo and radiation over the years. Now, they were not malignant. They were benign tumors, but they kept coming. Yeah. And they can grow and cause a huge damage. And the one that got away from us at the end of his life was the one in brain is in the wrong place. It was in his brain stem, so that ultimately we couldn't. We lost control of it.
B
And how old was he?
A
27. Just turned. Well, he's just a couple months from his 27th birthday.
B
So young.
A
Yeah.
B
So young. I'll show you.
A
But he did more in those 27 years than most of us do in 100.
B
Can we play some tape of Nick?
A
Sure.
B
I'll take this. Nick's jacket. Awful talking about Nick.
A
Okay. Different Nick. Right.
B
Only one Nick in the house.
A
Let's do it. You cannot tell the Cavaliers story, the history of the Cavaliers, and not include Nick Gilbert.
B
Nick, you're the ambassador for the National Children's Tumor foundation, and you've been dealing with a nerve disorder since you were born. Your dad called you his own personal hero. How's that make you feel? Well, I mean, what's that to.
A
Like the luck of the Knick.
B
That's you taking him to a.
A
To a draft, to the lottery. That was 2011, I think.
B
Yeah.
A
And he was 14 years old. You know, sometimes they throw the GM out, sometimes. An ex player.
B
Yeah.
A
He got. He couldn't do so many things because of what he had. He couldn't get his driver's license. He couldn't play sports like other kids. So I thought up this idea. Let's send him out for this. This will make him feel good.
B
And did it?
A
It did.
B
It made everyone around him feel good.
A
It did. That's what he always did.
B
Yeah. Cause he was so funny.
A
He was funny.
B
I like his. What's not to like?
A
Yeah. I mean, he just comes up with that on the spot. And so that became. I mean, the headline of the Cleveland Plain Dealer the next day was, what's not to like?
B
So he. That was just like a. That was the first time he said it. I love that video because for people who are listening and not watching, like, the way you're looking at Nick when he's asked this question, he's by himself, standing up there, and the way you're looking at him is just such a look of love.
A
Yeah.
B
Seemed like. Yeah. Favorite person kind of love. So I think it's unimaginable. I've had friends, I've lost friends and seen their parents after.
A
Yes.
B
I think that's just like. I mean, I've lost my dad, but I think the most unnatural, unimaginable kind of loss that you had.
A
And it's been two and a half years now, almost three, but it never goes away. I don't think it ever will.
B
Have you? I mean, I feel so trite, but, like, what have you learned from that? From having raised Nick to be the person that he was and then having lost him?
A
Well, you do learn that there's some of the biggest things in life you just can't control. I mean, my stroke, his disease. And so no matter what you do, good or bad, there's things that are gonna happen that you have to deal with in life.
B
Yeah.
A
And sometimes the only choice is to play the cards you've been dealt and also try to have gratitude for the good things that you have.
B
I imagine the 27 years that Nick was there, you guys put. You put a lot of money into trying to research.
A
We did, and we still are now.
B
And do you think that you will?
A
I think so. Our foundation has two missions. One is to cure nf, the other is Detroit related stuff.
B
Okay. How much have you invested in the cure for nf?
A
I mean, hundreds of millions, but there's others that put in money too, so.
B
And why is it so hard?
A
It's just a very tough disease. It's genetic. And it's not just one gene. These diseases, there's like, without getting into the big science discussion, something like 30 or 60 different genes have to be dealt with to cure the disease or something. Some of the most promising research we're doing. There's something. You ever hear of organoids?
B
Organoids.
A
Organoids. So they. They grow organs in the lab in a dish. I mean, you grow a liver in a dish and then you somehow try to grow tumors on the liver. And you can even make those tumors very similar to the patients you're trying to cure. And then you could try thousands of different agents and see which ones work. I mean, I don't know if I'm saying it exactly.
B
No. But it's basically like you're setting up like a model liver to test everything on so that you're not putting a human body through all of that before you.
A
And you can test more things on it. Yep.
B
Yeah. And that's the most promising, I think,
A
with AI and all the.
B
There's some more creative.
A
Yeah, I do.
B
How do you guys remember him?
A
We do A lot of things. Between two of the bigger buildings we built in Detroit, we created an outdoor plaza called Nick Gilbert Way, which is named after him, which is an outdoor kind of meeting place. He was working on a sports bar in Detroit before he died himself, and we picked it up and did it. We called it Gillies, which is the nickname his friends used to call him. And of course, the best thing we can do is cure this disease in his name.
B
Yeah. That's what you hope to get done?
A
That's what we hope to get done, yes.
B
You've also retired. Didn't you retire a jersey?
A
Yes, the Cavs, we did retire with a bow tie on it.
B
What number? Because he would always wear his bow tie.
A
Yeah, the bow tie. No number, just a bow tie.
B
I don't know where to go from that. It's such a shitty thing.
A
I know.
B
It's the worst thing. We'll be right back after the break. Do you think the NBA is the most fair thing in America?
A
Fair thing in America?
B
Yeah, the most fair thing in America.
A
Well, we run it. I think it's great that the union, the owners have come to a great agreement over the last 10 years. It really allows the MBA to flourish and their check on each other. It's almost like 50, 50 of the revenue. Of course, the owners have all the costs.
B
So you like this idea of giving more money to taxpayers, like having taxpayers participate more in wealth creation? When the government is making subsidies or.
A
Yeah, if the government's going to give a subsidy or something, why shouldn't they get equity?
B
Yeah.
A
Yeah. Why not?
B
What are other ways that, like, the US could learn from this MBA model? It's the last thing I'll ask you before we move on. What are the other things that the US could learn from this NBA model about being fair, about some level of redistribution? I mean, that's really what the NBA is doing. Right? Redistributing talent so that the game is still worth watching.
A
Yeah. Keep in mind they're forced to do that because they're going to lose fans. If you don't have a competitive league, but all the leagues do that. Baseball does that, football does that, hockey does that.
B
I think the United States is also losing fans right now within the country.
A
Yes.
B
Because they don't have a system that's kind of figuring out, even with these Trump accounts that Michael Dahl is doing. And I mean, I think it's a big problem that they're trying to get ahead of. Of how do you get people to believe in anything? Like, how do you get anyone in America to believe in anything anymore.
A
I think from my standpoint, what we've done as a business, I'd like to encourage other companies to take an activist role in one big issue. Because when you're a company, you've got an army of people that are working in the business, and we have 15,000 in Detroit. That's a lot of people. And all of them participate in something. So that's a lot of people get a lot of things done. You have access to capital, you have relationships you've built up over decades.
B
Yeah.
A
So we've come up with this concept. You know, there's for profit, there's not for profit. We want to start calling our business a more than profit, which means, yes, we care about profits, but we'll do more than that. Okay, so maybe we'll write a book on that. What do you think?
B
I think that would be good.
A
Maybe you can write it.
B
I don't know if I can write it, but I think it'd be good. I mean, I think that what you've done for Detroit is obviously remarkable. I also don't think we can just rest on people who create wealth to grow up and learn that they can contribute. I mean, you did it early, and you and your ex wife were very invested in Detroit and given a lot to it. You recently broke up.
A
Yes.
B
Can you call it that when it's a long marriage?
A
30 years.
B
30 years. What is it like to date as a billionaire?
A
It's not fun.
B
Because you can't use the apps.
A
No.
B
You don't want to. They're terrible. I don't think you do. It's not fun.
A
I generally date journalists.
B
All right, we'll end it there. By the way, I end every episode of Smart Girl. Dumb questions. Asking my guest a question that they have that they're not smart about. A dumb question they have that they wouldn't want to ask out loud if they've asked their phone.
A
Well, I set it up when I sat down here earlier, which was, well, you have a SGDQ on your microphone.
B
Yeah. And you asked me.
A
I asked. I go, what does that stand for?
B
That's true. It's okay. That's very. Yeah.
A
I was looking at the dq, thinking, dairy Queen, Dairy Queen.
B
Do you have any other questions that you think you don't know the answer to?
A
I'm sure there's a lot of questions I don't know. Where did we come from? Why are we here?
B
That's why. You watch all that universe.
A
Yeah.
B
All right, Dan, Gilbert, thank you so much for being here.
A
Thank you, Naeem. It's my pleasure.
B
And thank you for being a good sport. When I wore my Knicks gear, of course, I'm not even like, a deep, deep. I mean, I don't want to say this, Bill. I. I feel like I'm like this wave of New Yorkers who have, like, become excited about the Knicks. Front runner, frontrunner. You gave us a big win.
A
Okay, well, there's always next year.
B
There's always next year. We'll see with LeBron, maybe the king. All right, thank you so much, Dan.
A
Thank you.
B
Bye. I'm so glad Dan made time for that conversation. One of the ways that he remembers his son Nick is this tattoo on his right arm that you. You could probably see if you're watching this episode on Spotify or on YouTube. But I love how he talks about Nick, and I actually wish I had the opportunity to interview Nick Gilbert, too, because he sounds like such a funny, happy person, and I can't imagine going through life with that knowledge that it might end so clearly. I guess we all have that, but at such a young age and having the kind of joie de vivre and extroversion that he seemed to have. That's something I so admire about people. The ability to make the most out of what they have and be grateful. And Dan is certainly that, too, for his surviving the stroke. I also admire people saying what they don't know, as you can tell by the show title. And Dan did that a few times in the conversation, not just asking what SGDQ meant, but also when it came to other items, and particularly the etymology of dropping dimes, which, in case you were wondering, I did go look it up afterwards. And there are three theories on this. The first is a perfect 10 theory. Like, oh, my gosh, it was a 10 out of 10 dropping dimes. The second is a payphone theory, which is, like, back in the day, you would ask for a dime to make a call, and that's kind of like an assist. And then the third is a snitch theory, which I kind of like the most, which is the idea that, you know, you're assisting the police and you're dropping dimes. After taping, I asked Dan about that idea that wealth is created and not a pie out there. And I asked him, like, don't you think all the time about luck, especially given what happened with Nick and. And your own stroke? And he told me that he, of course, believes in luck, but you know what they say, And I didn't know what they say and he said the harder you work, the luckier you get. I think that is true, but we also can't rely on the charity and the willingness of people who make wealth to then give it back to society. We have to have a better way of capturing that. It just feel like building up government and Dan has helped do that in places like Detroit can empower them to do a lot more for everybody and not just for those who have a seat at the table. For everything else though, as Nick Gilbert would say, what's not to like? That's it for this episode of Smart Girl Dumb Questions. I want to know what you think. What do you think about the NBA, the USA? Billionaires? Write in tell us. I'm anemaraza101mail.com you can find us on Social Smart Girl Dumb Questions and obviously you should like share, subscribe the show and also please leave a review. We love reviews. We want your review. Ideally it's 5 stars. This episode was produced by Dusta Wonrad, Melissa Lee Gibson, Santana Nigam and Aisha Jordan, mixed and engineered by the great Kam Schenken. I'm your host Naeem Araza and I'll see you next week for an all new Smart Girl Dumb Questions. Until then, drop us some dimes with ideas for the show.
A
Sam. Ryan Reynolds here from Mint Mobile. I don't know if you knew this,
B
but anyone can get the same Premium
A
Wireless for $15 a month plan that I've been enjoying.
B
It's not just for celebrities. So do like I did and have one of your assistant's assistants switch you to Mint Mobile today. I'm told it's super easy to do@mintmobile.com Switch upfront payment of $45 for three month plan equivalent to $15 per month required intro rate first three months only, then full price plan options available, taxes and fees extra. See full terms@mintmobile.com.
Episode: Can the NBA Fix the USA?
Host: Nayeema Raza
Guest: Dan Gilbert (Cleveland Cavaliers owner, entrepreneur, Detroit booster)
Release Date: June 23, 2026
Nayeema Raza sits down with Dan Gilbert, billionaire owner of the Cleveland Cavaliers and major Detroit investor, to tackle the “dumb question”: Can lessons from the NBA’s way of doing business make American society fairer? They explore everything from NBA owner drama to Detroit’s revival, how wealth is created (and shared), the ethics of billionaire philanthropy, and Gilbert’s own journey through tragedy, family, and business. The conversation is candid, humorous, at times deeply personal, and full of practical insights and real talk about power, community, and what makes a life meaningful.
Collective Model:
Players’ Power:
Limits to Applying NBA Model to the US:
Detroit Rebuilding:
Power, Charity & Critique of Billionaire Philanthropy:
Role of Government:
| Timestamp | Segment/Topic | |-----------|------------------------------------------------------------| | 00:00 | NBA owner drama—commissioner’s authority | | 07:16 | Dan’s stroke: causes, rehabilitation, and perspective | | 16:14 | Is the NBA “socialist” and can the USA learn from it? | | 21:00 | LeBron James “Comic Sans” letter—regret and redemption | | 31:46 | NBA as business: value, ROI, teams as art and hobby | | 34:55 | Class division, are billionaires “too rich”? | | 37:16 | Detroit revitalization; working with mayors, community | | 45:34 | Should billionaires give away 50% to the US government? | | 54:44 | Losing his son Nick—living with loss, foundation, legacy | | 58:47 | Lessons from tragedy—gratitude and control | | 62:06 | Should government get equity for subsidies? | | 63:29 | “More than profit”—business activism, doing good | | 64:38 | Dan’s “dumb question”: cosmic curiosity |
For more on this episode or to share your own “dumb questions,” reach out to Nayeema at nayeema.raza101@gmail.com or follow “Smart Girl Dumb Questions” on social platforms.