Dan Gilbert

The Twitter bio paradox: signaling vs countersignaling

Sam contrasts billionaire Dan Gilbert's humble 'retired pizza delivery driver' bio with a striver's 'Forbes 30 Under 30 finalist' bio. The harder you try to look like a baller, the more you signal you're still trying; the rich man counter-signals by acting like a regular guy.

“And so I said, on one side you have a baller trying to act like, like trying to counter signal that he's a regular guy. And on the other side, you have a regular guy trying to signal that he's a baller. And, you know, this is the paradox of Twitter. The harder you try, the more you tell me that you're still trying.”

Steal thisAudit your own bio: if you list awards or titles, you're signaling you still need them.

Dan Gilbert: the 'capitalist Batman' rebuilding Detroit

Andrew profiles Dan Gilbert, who went from a struggling Detroit bar family and pizza delivery to founding Quicken Loans, and whose net worth jumped from ~$7B to $57B even as he survived a major stroke; he pours money into revitalizing Detroit.

“He's like a capitalist Batman in Detroit, and I'll talk about some of the cool stuff he's done. And one of the things I like about him as well is that he. He does a lot of stuff that might not work. He takes big swings, takes big risks that he thinks can make the world better. And he invests in all sorts of crazy ideas.”

Gilbert moved 4,000 employees into bankrupt Detroit and bought up downtown

As Detroit went bankrupt in the financial crisis, Gilbert moved his entire ~4,000-person team from the suburbs into downtown, then bought billions of dollars of derelict buildings, ending up owning 20-30% of downtown and pledging to pay off $300M in residents' property taxes.

“he says, "Fuck it, we're moving back into Detroit," and he moves his entire team into Detroit. So he had 4,000 or so employees. If you actually go to Detroit, it's called Campus Martius or something, and it's right in the center of downtown, this huge building, and he moved everyone there.”

Andrew cold-emailed Dan Gilbert at 1am and got a yes in 5 minutes

Andrew's habit of cold-emailing interesting people paid off: he emailed billionaire Dan Gilbert at 1am, got a reply in 5 minutes, and ended up flying to Detroit for a two-day tour where Gilbert spent two hours saying yes to ideas instead of no.

“I have this habit of just cold emailing people I think are interesting. And like 95% of the time, I just don't hear back. But I wrote him an email at like 1 in the morning and said, hey, I'd love to meet you. And I get an email back like 5 minutes later and he's just like, yeah, sure.”

Steal thisCold-email the people you admire; most won't reply, but the occasional yes changes everything.

Gilbert's barbell: a boring cash-flow business funds the crazy bets

Gilbert pairs a dull, cash-flowing mortgage business with wild venture bets, personally onboards every new hire on culture once a month, and lives by 'isms' like 'yes before no' and 'money follows, it does not lead.'

“he says, there's this great quote. He says, one of our things is that money follows. It does not lead. So we want people that are fired up and passionate about their mission and people that aren't so married to spreadsheets and thinking that kind of voodoo controls the future because it doesn't.”

Steal thisPair a boring cash-flowing business with a portfolio of big bets, and let mission lead money, not the reverse.

Gilbert's barbell: a boring cash-flow business funds the crazy bets

Gilbert pairs a dull, cash-flowing mortgage business with wild venture bets, personally onboards every new hire on culture once a month, and lives by 'isms' like 'yes before no' and 'money follows, it does not lead.'

“he says, there's this great quote. He says, one of our things is that money follows. It does not lead. So we want people that are fired up and passionate about their mission and people that aren't so married to spreadsheets and thinking that kind of voodoo controls the future because it doesn't.”

Steal thisPair a boring cash-flowing business with a portfolio of big bets, and let mission lead money, not the reverse.

Dan Gilbert: the mortgage king who co-founded StockX off his kids' sneakers

Shaan marvels at Dan Gilbert, owner of the Cleveland Cavaliers and Quicken Loans, who noticed his kids were obsessed with sneakers and helped turn a sneaker store into StockX, a stock exchange for shoes that became a billion-dollar company.

“the other company that Dan Gilbert started or helped start was StockX, which is a billion dollar, uh, what do you, uh, eBay for sneakers basically.”

Dan Gilbert sold his mortgage company to Intuit, then bought it back

Sam recounts how Dan Gilbert started Rock Financial in 1985, took it public around $80M in revenue, sold it to Intuit for roughly $600M, then bought it back two years later and grew it into a giant that went public again as Rocket Mortgage.

“in like 1985, he started a mortgage business where they would originate loans for mortgages. And I don't know if that means they're the bank or if they're connecting you with the bank. It was called Rock Financial and he grew it. And I think in year 11 it went public with like $80 million in revenues, like a really good company.”

The pre-mortem: why will this have failed 6 months from now?

Shaan's decision-making habit: imagine fast-forwarding 6-12 months to a future where the project has failed, ask what the most likely reason would be, write it down now, and start working on it immediately, then revisit to see what he was right or wrong about.

“What's the, 6 months from now, if we fast forward to there and it's failed, what's the most likely reason I'd be giving you over a beer when we're like, dude, what happened? That was great. And then I write that down now and I start to work on it now.”

Steal thisRun a pre-mortem on every project: name the most likely failure reason 6 months out, write it down, and start mitigating it today.

Incentive-caused bias: share buybacks line the CEO's own jeans

Wilkinson explains incentive-caused bias using buybacks: CEOs paid in stock options benefit when share price rises, and buybacks shrink the share count to lift price — so a 'return capital to shareholders' move can really be self-enrichment.

“a lot of CEOs are compensated based on share price because they get stock options. So their stock options become more valuable when the share price goes up. And what makes the share price go up but share buybacks? So when you buy back shares, there's fewer shares and each individual share is worth more. So it's actually a way for the CEO to put money in his or her own jeans.”