00:00

So, yeah, my guy is,

So, yeah, my guy is,

00:03

Dan Gilbert.

Dan Gilbert.

00:04

And the reason I thought he was super interesting. I've talked about him a little bit in the past, but This guy has had a freaking

And the reason I thought he was super interesting. I've talked about him a little bit in the past, but This guy has had a freaking

00:11

massive year. So,

massive year. So,

00:13

you know, two years ago or something,

you know, two years ago or something,

00:15

he was worth, like, six seven, eight billion dollars,

he was worth, like, six seven, eight billion dollars,

00:19

baby billionaire.

baby billionaire.

00:20

Now he's worth fifty seven billion. Wait five and seven.

Now he's worth fifty seven billion. Wait five and seven.

00:25

Five seven fifty seven. He's number twenty one, one of the wealthiest people in the United States.

Five seven fifty seven. He's number twenty one, one of the wealthiest people in the United States.

00:30

And this is he's had a crazy couple years. So I think it was about two years ago. He had a massive stroke. So he was on the golf course with a friend,

And this is he's had a crazy couple years. So I think it was about two years ago. He had a massive stroke. So he was on the golf course with a friend,

00:40

And, the the friend just happened to be a doctor, and he said, oh, that's weird. I'm having these symptoms. So his doctor got him to the hospital,

And, the the friend just happened to be a doctor, and he said, oh, that's weird. I'm having these symptoms. So his doctor got him to the hospital,

00:48

And they he had a stroke in the hospital,

And they he had a stroke in the hospital,

00:51

and in the hospital, they were able to do this special procedure that if he hadn't been in the hospital, might have died or it might have been way worse. Right? So we got super lucky.

and in the hospital, they were able to do this special procedure that if he hadn't been in the hospital, might have died or it might have been way worse. Right? So we got super lucky.

01:00

Yeah. And, you know, as lucky as one can be having a stroke, horrible thing, And,

Yeah. And, you know, as lucky as one can be having a stroke, horrible thing, And,

01:05

now he's been basically rehabilitating himself and getting back on his feet for the last two years. And so he's had this horrible personal tragedy But at the same time, he's become worth, you know, six x, you know, as much. And I bet he would give it all away to not have had the stroke or whatever. So it's super fascinating.

now he's been basically rehabilitating himself and getting back on his feet for the last two years. And so he's had this horrible personal tragedy But at the same time, he's become worth, you know, six x, you know, as much. And I bet he would give it all away to not have had the stroke or whatever. So it's super fascinating.

01:22

This guy,

This guy,

01:23

he described it really well. When they IPO, they just IPO ed his mortgage business. He said, this is a thirty year

he described it really well. When they IPO, they just IPO ed his mortgage business. He said, this is a thirty year

01:31

are starting overnight success, thirty years in the making.

are starting overnight success, thirty years in the making.

01:35

So this guy's been at it for a really long time.

So this guy's been at it for a really long time.

01:38

I think he's super interesting because he started with nothing.

I think he's super interesting because he started with nothing.

01:42

His dad owned a struggling Detroit bar. He worked in pizza delivery.

His dad owned a struggling Detroit bar. He worked in pizza delivery.

01:47

He just kinda stumbled into hustling and was a good salesperson, and he started a business, and that business was a company called,

He just kinda stumbled into hustling and was a good salesperson, and he started a business, and that business was a company called,

01:55

Rock Financial, which became Quicken Loans, which I'll talk about in a second.

Rock Financial, which became Quicken Loans, which I'll talk about in a second.

01:59

One of the reasons I think he's really interested interesting is that he's invested into revitalizing his home city. So his mission is to revitalize

One of the reasons I think he's really interested interesting is that he's invested into revitalizing his home city. So his mission is to revitalize

02:07

Detroit and get it back on its feet because it struggled a lot.

Detroit and get it back on its feet because it struggled a lot.

02:12

He's like a capitalist Batman in Detroit and I'll talk about some of the cool stuff he's done.

He's like a capitalist Batman in Detroit and I'll talk about some of the cool stuff he's done.

02:17

And one of the things I like about him as well is that he,

And one of the things I like about him as well is that he,

02:20

he does a lot of stuff that might not work, He takes big swings, takes big risks that he think can make the world better,

he does a lot of stuff that might not work, He takes big swings, takes big risks that he think can make the world better,

02:28

and he invests in all sorts of crazy ideas. He also has five kids, which I think is pretty freaking cool. I love to see that with these, you know, billionaires. They're not just, like, miserable by themselves and they care about kids and stuff and seems pretty family focused.

and he invests in all sorts of crazy ideas. He also has five kids, which I think is pretty freaking cool. I love to see that with these, you know, billionaires. They're not just, like, miserable by themselves and they care about kids and stuff and seems pretty family focused.

02:42

And then, you know, he's been through these personal challenges, the stroke, and then also his eldest son was born with this disease called neurofibromatosis,

And then, you know, he's been through these personal challenges, the stroke, and then also his eldest son was born with this disease called neurofibromatosis,

02:50

which is, like, super rare. And he's poured a bunch of money,

which is, like, super rare. And he's poured a bunch of money,

02:53

his own money into funding research around that disease. So it's been

his own money into funding research around that disease. So it's been

02:57

fascinating.

fascinating.

02:59

So he said, there's a quote. He said, when I when we grew up, all I wanted to do,

So he said, there's a quote. He said, when I when we grew up, all I wanted to do,

03:04

was do two things, own a sports team and a casino.

was do two things, own a sports team and a casino.

03:08

And now he owns both. So this is kinda like a childhood dream.

And now he owns both. So this is kinda like a childhood dream.

03:12

And his companies are Quicken Loans, which is the largest home mortgage lender in the United States. They're bigger than Wells Fargo, which is freaking crazy.

And his companies are Quicken Loans, which is the largest home mortgage lender in the United States. They're bigger than Wells Fargo, which is freaking crazy.

03:20

He owns the Cleveland cavaliers, the basketball team, and a few other sports franchises.

He owns the Cleveland cavaliers, the basketball team, and a few other sports franchises.

03:25

Until recently he owned a casino.

Until recently he owned a casino.

03:27

I think it was called Jack, which owned a whole bunch of casinos, but I think he sold it. And then he also owns rock ventures. And rock ventures is where all the big swings happen and all the philanthropic stuff happens. So

I think it was called Jack, which owned a whole bunch of casinos, but I think he sold it. And then he also owns rock ventures. And rock ventures is where all the big swings happen and all the philanthropic stuff happens. So

03:39

They own a ton of real estate, almost all in Detroit,

They own a ton of real estate, almost all in Detroit,

03:43

and then they do venture capital. And they've invested in everything from

and then they do venture capital. And they've invested in everything from

03:48

restaurants,

restaurants,

03:49

to, you know, real estate businesses,

to, you know, real estate businesses,

03:52

hotels,

hotels,

03:52

crazy tech companies, and all sorts of other stuff. He owns Rob report, which is Can I tell you one more thing that he can I tell you a few more things that he owns? That's interesting.

crazy tech companies, and all sorts of other stuff. He owns Rob report, which is Can I tell you one more thing that he can I tell you a few more things that he owns? That's interesting.

04:02

So he owns I think he owns fat head. Do you know fat head? Yeah. Yeah. I believe in sports. It's, like, those, like, big hands and stuff. And, like, you get weird blow up to your face. Kid and you wanna put, like, like, of the face of Michael Jordan on your wall. It's like a decal that you put on your wall. I think he owns the whole thing. He just bought dictionary dot com and thesaurus dot com.

So he owns I think he owns fat head. Do you know fat head? Yeah. Yeah. I believe in sports. It's, like, those, like, big hands and stuff. And, like, you get weird blow up to your face. Kid and you wanna put, like, like, of the face of Michael Jordan on your wall. It's like a decal that you put on your wall. I think he owns the whole thing. He just bought dictionary dot com and thesaurus dot com.

04:25

Totally random. We were actually we helped him. I I know him. I'll I'll talk about that a little bit, but, we helped him with that acquisition a little bit. Oh, no way. So you know about it. It was like a it's like a twenty million dollar revenue thing or more, maybe.

Totally random. We were actually we helped him. I I know him. I'll I'll talk about that a little bit, but, we helped him with that acquisition a little bit. Oh, no way. So you know about it. It was like a it's like a twenty million dollar revenue thing or more, maybe.

04:39

It's been doing that for, like, ten years I I mean, I don't have any insider information. These are guesses.

It's been doing that for, like, ten years I I mean, I don't have any insider information. These are guesses.

04:45

And am I right?

And am I right?

04:47

Yeah. Yeah. He owns dictionary dot com and thesaurus dot com.

Yeah. Yeah. He owns dictionary dot com and thesaurus dot com.

04:51

And, like, when you talk to him about why he bought it, he's just like, you know, I think this is cool. Like, he's just like, I had all these ideas of things I could do with it. He's not, like, going, oh, I bought it for x times EBITDA, and I'm gonna make a twenty percent return. And this is what I find so cool about this guy is he'll just say yes. So he owns, like, Rob Report, which is like a magazine for rich people dictionary dot com.

And, like, when you talk to him about why he bought it, he's just like, you know, I think this is cool. Like, he's just like, I had all these ideas of things I could do with it. He's not, like, going, oh, I bought it for x times EBITDA, and I'm gonna make a twenty percent return. And this is what I find so cool about this guy is he'll just say yes. So he owns, like, Rob Report, which is like a magazine for rich people dictionary dot com.

05:13

He owns or has a very large stake in Shayanola. So Shayanola has this, like, insane hotel in Detroit. They make watches,

He owns or has a very large stake in Shayanola. So Shayanola has this, like, insane hotel in Detroit. They make watches,

05:22

he owns

he owns

05:23

stock x, which is like a it's basically like a stock market for sneakers and watches, which is awesome.

stock x, which is like a it's basically like a stock market for sneakers and watches, which is awesome.

05:29

Because, like, he he co founded it. He's like

Because, like, he he co founded it. He's like

05:35

fifty fifty something, fifty six, I think. Oh, he's that young. Wow. Okay.

fifty fifty something, fifty six, I think. Oh, he's that young. Wow. Okay.

05:39

A little bit older than, like, a sneaker head.

A little bit older than, like, a sneaker head.

05:43

And he Totally. I he's a co founder. I know that. So he was a he

And he Totally. I he's a co founder. I know that. So he was a he

05:47

He he's got investments in e sports, like, just all sorts of stuff. And then he's also a large LP and a lot of venture funds. Kinda quietly. Like, he's the largest LP in Ludlow ventures. He's got his own venture fund. And so you you look at it, and he's got this barbell. Right? He's got a really kind of dull boring, you know, mortgage business, which is really innovative in and of itself. Just what he's done is kinda like Brad. What he's done is, like, basically taken this fragmented crappy industry run by banks and small lenders and, like, built out this massive structure and been very innovative around culture and other stuff.

He he's got investments in e sports, like, just all sorts of stuff. And then he's also a large LP and a lot of venture funds. Kinda quietly. Like, he's the largest LP in Ludlow ventures. He's got his own venture fund. And so you you look at it, and he's got this barbell. Right? He's got a really kind of dull boring, you know, mortgage business, which is really innovative in and of itself. Just what he's done is kinda like Brad. What he's done is, like, basically taken this fragmented crappy industry run by banks and small lenders and, like, built out this massive structure and been very innovative around culture and other stuff.

06:23

So let me let me just give the history of what happened though. So, basically, in nine eighty five, him and his little brother,

So let me let me just give the history of what happened though. So, basically, in nine eighty five, him and his little brother,

06:30

start Rock Financial,

start Rock Financial,

06:32

which is basically a independent mortgage lender. So when someone you know, needs a house or whatever it is. They go to them.

which is basically a independent mortgage lender. So when someone you know, needs a house or whatever it is. They go to them.

06:40

They figure out, they basically make them an offer,

They figure out, they basically make them an offer,

06:43

to lend them the money. And then I think they go sell the risk. So they would lend them the money, and then they would sell it off to a bank over time.

to lend them the money. And then I think they go sell the risk. So they would lend them the money, and then they would sell it off to a bank over time.

06:51

And basically in the late nineteen nineties, company grew into a huge business, one of the largest,

And basically in the late nineteen nineties, company grew into a huge business, one of the largest,

06:57

independent in the United States. And with the dot com boom, they launched an internet strategy

independent in the United States. And with the dot com boom, they launched an internet strategy

07:03

where they just made,

where they just made,

07:05

rock financial. I think it was rock financial dot com or digital mortgage dot com or something like that. And

rock financial. I think it was rock financial dot com or digital mortgage dot com or something like that. And

07:11

in,

in,

07:13

And in two thousand, what was it?

And in two thousand, what was it?

07:16

No. Nineteen ninety seven or something,

No. Nineteen ninety seven or something,

07:19

Intuit acquired

Intuit acquired

07:20

their business because they were like, oh my god, this is like, you know, this huge disruptive digital finance thing. And so,

their business because they were like, oh my god, this is like, you know, this huge disruptive digital finance thing. And so,

07:27

what ended up happening is the doc comboom blew up. And in two thousand two, he came back and he bought his business back. So we sold it for a ton of money into it. I think that her sale was ninety million.

what ended up happening is the doc comboom blew up. And in two thousand two, he came back and he bought his business back. So we sold it for a ton of money into it. I think that her sale was ninety million.

07:39

Okay.

Okay.

07:40

Is that right? He he basically I I don't know. I don't have the exact number here, but, something like that. So, you know, the guy made a lot of money especially for the nineties, but he wasn't like a crazy billionaire yet. Then he raised money from investors.

Is that right? He he basically I I don't know. I don't have the exact number here, but, something like that. So, you know, the guy made a lot of money especially for the nineties, but he wasn't like a crazy billionaire yet. Then he raised money from investors.

07:54

So himself and some friends

So himself and some friends

07:56

went back to Intuit bought it back. I don't know what the number was. And what's interesting is they kept the Quicken Loans name. So Intuit owns Quicken, the financial personal finance software and they branded it Quicken. And so now there's this weird other business they own called Quicken Loans, even though that's an Intuit brand. So it's kind of a funny

went back to Intuit bought it back. I don't know what the number was. And what's interesting is they kept the Quicken Loans name. So Intuit owns Quicken, the financial personal finance software and they branded it Quicken. And so now there's this weird other business they own called Quicken Loans, even though that's an Intuit brand. So it's kind of a funny

08:16

thing.

thing.

08:17

And it just kept he basically took it took it back, got rid of all the crap, the Intuit that it added, and started growing it again.

And it just kept he basically took it took it back, got rid of all the crap, the Intuit that it added, and started growing it again.

08:25

And

And

08:26

this whole time, he's living in Detroit and watching his own city totally fall apart. So in the financial crisis,

this whole time, he's living in Detroit and watching his own city totally fall apart. So in the financial crisis,

08:34

you know, Detroit, I think went bankrupt.

you know, Detroit, I think went bankrupt.

08:36

And he, meanwhile, is, like, super rich and living out in the suburbs. And he says, fuck it. We're moving back into Detroit, and he moves his entire team,

And he, meanwhile, is, like, super rich and living out in the suburbs. And he says, fuck it. We're moving back into Detroit, and he moves his entire team,

08:46

into Detroit. So he had four thousand or so

into Detroit. So he had four thousand or so

08:49

employees.

employees.

08:51

They literally bought if you actually go to Detroit, there's this,

They literally bought if you actually go to Detroit, there's this,

08:54

it's called campus Martias or something, and it's right in the center of downtown, this huge building,

it's called campus Martias or something, and it's right in the center of downtown, this huge building,

08:59

and he moved everyone there. And he basically said,

and he moved everyone there. And he basically said,

09:02

for my own employees and for the city, we're just gonna fix it. And so he built

for my own employees and for the city, we're just gonna fix it. And so he built

09:08

casinos. He built, like, a private security,

casinos. He built, like, a private security,

09:11

firm. So if you walk around, there's, like, there's, like, normal police and then there's, like, Dan's police.

firm. So if you walk around, there's, like, there's, like, normal police and then there's, like, Dan's police.

09:18

He bought billions of dollars of derelict buildings,

He bought billions of dollars of derelict buildings,

09:21

you know, literally like you go there and there's like skyscrapers.

you know, literally like you go there and there's like skyscrapers.

09:25

And he's just it's like going to Chicago. And he's like, oh, yeah. I own the Series Tower and this and this and, like, basically all of downtown Detroit. He owns, like, twenty, thirty percent of. And,

And he's just it's like going to Chicago. And he's like, oh, yeah. I own the Series Tower and this and this and, like, basically all of downtown Detroit. He owns, like, twenty, thirty percent of. And,

09:36

he also just announced that he's gonna pay off three hundred million dollars of property taxes

he also just announced that he's gonna pay off three hundred million dollars of property taxes

09:41

for Detroit residences. So this guy really, really cares about Detroit.

for Detroit residences. So this guy really, really cares about Detroit.

09:45

And since since he started it, it's now become

And since since he started it, it's now become

09:49

the largest, independent

the largest, independent

09:52

mortgage business in in the United States.

mortgage business in in the United States.

09:55

You know, they've gone public. They had this huge IPO,

You know, they've gone public. They had this huge IPO,

09:58

and it's been it's been a crazy story. He But what I what I what I love about this guy is just he's got such a crazy collection of businesses.

and it's been it's been a crazy story. He But what I what I what I love about this guy is just he's got such a crazy collection of businesses.

10:07

I think if I remember correctly, I think I'm probably I think I'm right, but I believe he sold it for ninety.

I think if I remember correctly, I think I'm probably I think I'm right, but I believe he sold it for ninety.

10:14

He bought it back for, like, twenty.

He bought it back for, like, twenty.

10:16

And I think he took it public. Did he take it public, like, either recently or right away?

And I think he took it public. Did he take it public, like, either recently or right away?

10:22

Quite recently. Like, it was, like, like, six months ago. And he owned most of it when it went public? He owned, like, eighty five or ninety percent of it. And it went public. It's totally crazy. What's the market cap now?

Quite recently. Like, it was, like, like, six months ago. And he owned most of it when it went public? He owned, like, eighty five or ninety percent of it. And it went public. It's totally crazy. What's the market cap now?

10:34

The market cap is

The market cap is

10:36

let's see here. Market cap's forty six billion dollars. Wow. So, yeah, Where's the other ten billion come from? Just his other just his

let's see here. Market cap's forty six billion dollars. Wow. So, yeah, Where's the other ten billion come from? Just his other just his

10:45

other stuff? A lot. Yeah. A lot of real estate. You think the cap years are probably worth, you know, five hundred million to a billion. Oh, we forgot about that whole part. He knows.

other stuff? A lot. Yeah. A lot of real estate. You think the cap years are probably worth, you know, five hundred million to a billion. Oh, we forgot about that whole part. He knows.

10:54

You know, all these stock x is worth, I think a couple billion dollars now now.

You know, all these stock x is worth, I think a couple billion dollars now now.

10:59

So he's just got this crazy collection of stuff. And and so Chris and I got to meet him.

So he's just got this crazy collection of stuff. And and so Chris and I got to meet him.

11:05

The other cool thing about this guy is, like, He's just a wild card. Like, I so I read about him in the New York Times. They did this profile of him, and I I have this habit of just cold emailing people I think are interesting. And, like, ninety five percent of the time, I just don't hear back. But I wrote him an email at, like, one in the morning, and said, hey, you, you know, I'd love to meet you. And I get an email back, like, five minutes later, and he's just like, yeah, sure. And then I got a follow-up from his assistant, and we ended up flying to Detroit. And it, you know, sometimes when you go and meet these billionaires, they're like, whatever, you know, you walk in, you get twenty minutes with them. That's that. He was, like, incredible. They, like, planned this whole tour of Detroit. It was, like, this two day thing, like, every they set us up in their hotel.

The other cool thing about this guy is, like, He's just a wild card. Like, I so I read about him in the New York Times. They did this profile of him, and I I have this habit of just cold emailing people I think are interesting. And, like, ninety five percent of the time, I just don't hear back. But I wrote him an email at, like, one in the morning, and said, hey, you, you know, I'd love to meet you. And I get an email back, like, five minutes later, and he's just like, yeah, sure. And then I got a follow-up from his assistant, and we ended up flying to Detroit. And it, you know, sometimes when you go and meet these billionaires, they're like, whatever, you know, you walk in, you get twenty minutes with them. That's that. He was, like, incredible. They, like, planned this whole tour of Detroit. It was, like, this two day thing, like, every they set us up in their hotel.

11:52

And then Dan spent, like, two hours with us, and he's just this super nice guy. He's, like, deeply interested in what we're doing.

And then Dan spent, like, two hours with us, and he's just this super nice guy. He's, like, deeply interested in what we're doing.

12:00

And super engaged. And, like, every business I mentioned to him, he'd be like, how does that work? How can we get involved? What can we do? How could we do it? Like, he wants to say yes to ideas, which I always find really inspiring. Right? Cause I think some of these people have gotten really rich they've gotten rich by being, like, hyper disciplined and just saying no to everything, but he says yes before no.

And super engaged. And, like, every business I mentioned to him, he'd be like, how does that work? How can we get involved? What can we do? How could we do it? Like, he wants to say yes to ideas, which I always find really inspiring. Right? Cause I think some of these people have gotten really rich they've gotten rich by being, like, hyper disciplined and just saying no to everything, but he says yes before no.

12:21

That's really interesting. That's what Sean acts like. And I use I usually say no everything. Sean says yes to everything. And my joke is that, like, I'm, like, my success is probably gonna be quite predictable, and it will be really good. Sean's success is he's gonna go go completely broke and die, like, but die young, or he's gonna become a billionaire super fat, like, you know, it's like a It's a high risk, hydrocarbon. That's not the reality, but that's my joke.

That's really interesting. That's what Sean acts like. And I use I usually say no everything. Sean says yes to everything. And my joke is that, like, I'm, like, my success is probably gonna be quite predictable, and it will be really good. Sean's success is he's gonna go go completely broke and die, like, but die young, or he's gonna become a billionaire super fat, like, you know, it's like a It's a high risk, hydrocarbon. That's not the reality, but that's my joke.

12:51

I feel like I could root a word. I know I could be what I want to.

I feel like I could root a word. I know I could be what I want to.

12:56

I put my all in it like a day's all on a road. Let's travel never looking life.

I put my all in it like a day's all on a road. Let's travel never looking life.

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