David Rubenstein: Why Owners Care About Winning, Not Money

SPEAKER_1 (0:00)

Fall never arrives all at once. First the air, then the light, and slowly the things you love begin to find each other. A jacket meets a dress, a hoodie slips beneath a blazer, an old cap finds a new scarf. Because you don't simply step into the season, you create it layer by layer until it finally feels like fall.

Find fall your way at Ross.

SPEAKER_2 (0:30)

You're listening to this podcast so I know you've got a curious mind. Here's a helpful fact you might not know yet. Drivers who switch and save with Progressive save over $900 on average. Pop over to progressive.com, answer some questions and you'll get a quick quote with discounts that are easy to come by. In fact, 99 percent of their auto customers earn at least one discount. Visit progressive.com and see if you can enjoy a little cash back.

Progressive Casualty Insurance Company and Affiliates. National average 12-month savings of $946 by new customers surveyed who saved with Progressive between June 2024 and May 2025 Potential savings will vary.

SPEAKER_3 (1:08)

Today on The James Altucher Show.

David Rubenstein (1:11)

As a general rule of thumb, when professional sporting teams don't do well, it's easier to remove the coach than to remove the players.

Owners don't tend to remove themselves. At my firm, Carlyle, whenever we had to get rid of somebody, I asked one of my partners to do it because I wasn't very good at firing people. When I was supposed to originally fire people, I would actually wind up promoting them when they come into my office, when they tell me how great they really were. So they got rid of me as a firer, and we had somebody else in our firm fire people. You always have to be prepared to walk away on a deal if you're going to really be a good negotiator. Because if somebody knows that you'll pay any price, bear any burden, do anything to get the deal done, you're probably not going to get the best deal.

SPEAKER_3 (1:53)

This isn't your average business podcast, and he's not your average host. This is The James Altucher Show.

James Altucher (2:11)

So on this show, I'm usually the one asking the questions.

But near the end of this conversation, David Rubenstein kind of turned it around on me.

He asked me, why do I care whether the Mets win? And I didn't really have an answer. I said, I guess when I was a kid, it felt like I was winning when they won. And he said, yeah, that's it. That's the whole thing. And then he said, look, Baltimore has been the stepchild to New York and Boston for like 200 years. So if the Orioles win, some guy in Baltimore who's never going to make a dollar off that team, gets to feel as good as the guys in New York.

So David owns the Orioles now. His new book is Inside the Owner's Box. And there were two things he told me that I just can't shake. One, he was so bad at firing people that they basically talk him into promoting them instead. So his own firm took firing away from him. He didn't get better at it. He just stopped doing it. And two, he's more than doubled what the Orioles pay their players. And the team hasn't gotten better. And I mean, I've spent a lot of money in my life trying to fix things that were never money problems. And honestly, most of my life, I felt like a winner because of things I didn't even own. So I'm asking a guy who owns a baseball team how to stop. And here's David Rubenstein.

First off, just a question unrelated to your book, is there going to be a baseball season next year?

David Rubenstein (3:45)

To be honest, I don't think anybody really knows. I think that the negotiations are going on. But until the season is technically over and the contract is over in December, I don't think the negotiations will be taken that seriously in terms of really getting down to brass tacks. But I don't think anybody honestly knows. No owner knows, no player knows. We just don't know yet.

James Altucher (4:05)

And you're a relatively new owner of a baseball team, the Baltimore Orioles. And obviously, I love your technique of learning and also writing a book at the same time, which is, hey, let's interview all the sports team owners I can find. And I get both book and knowledge out of it.

What are some of the things you've learned? And then I have some specifics on this.

David Rubenstein (4:25)

I've learned that people that buy sports teams are not motivated by money as much as people that buy other kinds of companies are. You care about the community, you care about winning, you care about trying to do something for the area that you kind of represent.