Max Sterling

Stories about how successful people made their money.
The good, the bad and everything in between.

[Max Sterling @MaxSterlindh]

@0x_Squirrel i think she had made up her mind long before that party. once the trust was written, she wasn’t going to change it under pressure

[Max Sterling @MaxSterlindh]

In 1994, Jeff Bezos was still working on Wall Street when he started thinking about one question: what would he regret not doing when he was 80?

He called it his "regret minimization framework." The answer was to leave his job and build something on the internet, even though he had no guarantee it would work.

"I want to have lived my life so that when I'm 80, I've minimized the number of regrets I have."

Bezos had always been unusually precise. At Princeton, he even created a formal system for dating, but every blind date failed.

"I was always a good student. I was nerdy. That hasn't changed."

That same attention to detail showed up in his everyday life. Bezos once joked that his watch updates from the atomic clock 36 times a day.

The difference was where he eventually applied that mindset. The precision that didn't help him find a date became useful when he was deciding whether to leave Wall Street and build Amazon.

If you were 80 today, what decision would you regret not making?

[Reid @reidgrows]

https://t.co/YF5JtEIvDR

[Max Sterling @MaxSterlindh]

@builtinlevi one good night doesn’t mean you found a replacement for your salary. the real question is whether it can do the same thing 200 more times without blowing up the account

[Max Sterling @MaxSterlindh]

In 1995, Archie Karas had turned $50 into more than $40 million. Three weeks later, he had lost almost all of it.

He had $40 million.
He kept gambling.
In the video below, Karas talks about the gambling run that made him one of the most famous gamblers in Las Vegas.

Karas had arrived in Las Vegas with almost nothing. He borrowed $10,000 from a fellow gambler and started playing poker.

He won. Then he moved to pool and craps.

At his peak, Karas had more than $40 million.

Then he lost $11 million at craps. He lost another $2 million playing poker. He moved to baccarat and lost roughly $17 million more.

Within three weeks, the fortune was gone.

Karas described his attitude toward money in four words: “Money means nothing to me.”

He had turned $50 into $40 million.
He could not stop playing.

Was Archie Karas one of the greatest gamblers ever, or did he simply never know when to walk away?

[Max Sterling @MaxSterlindh]

@0x_Squirrel i’d say the casinos beat themselves here. they gave him the rules, he found a way to make them work in his favor, and then did exactly what he was invited there to do

[Max Sterling @MaxSterlindh]

@reidgrows she wasn’t asking for a normal inheritance, she was asking why the gap between her and her sisters was so massive in the first place

[Max Sterling @MaxSterlindh]

@vmrmax the part that stands out is having AI do the night shift while still keeping the final merge under human control. 214 fixes with only 3 rejected is pretty wild

[Max Sterling @MaxSterlindh]

@vmrmax yeah, having the discipline to walk away after a run like that is probably harder than winning in the first place

[Max Sterling @MaxSterlindh]

In 1995, Archie Karas had turned $50 into more than $40 million. Three weeks later, he had lost almost all of it.

He had $40 million.
He kept gambling.
In the video below, Karas talks about the gambling run that made him one of the most famous gamblers in Las Vegas.

Karas had arrived in Las Vegas with almost nothing. He borrowed $10,000 from a fellow gambler and started playing poker.

He won. Then he moved to pool and craps.

At his peak, Karas had more than $40 million.

Then he lost $11 million at craps. He lost another $2 million playing poker. He moved to baccarat and lost roughly $17 million more.

Within three weeks, the fortune was gone.

Karas described his attitude toward money in four words: “Money means nothing to me.”

He had turned $50 into $40 million.
He could not stop playing.

Was Archie Karas one of the greatest gamblers ever, or did he simply never know when to walk away?

[Reid @reidgrows]

https://t.co/YF5JtEIvDR

[Max Sterling @MaxSterlindh]

@0x_Squirrel yeah, that’s what makes his story so wild. once he got that far, walking away would’ve been the hardest bet of all

[Max Sterling @MaxSterlindh]

@Last161eth @QFEX been here since March and still waiting to see what all that activity pays off with, hope Season 0 delivers

[Max Sterling @MaxSterlindh]

@Last161eth Thank you

[Max Sterling @MaxSterlindh]

@Pixel_Neuron yeah, he knew how to win, he just didn’t know when to stop playing

[Max Sterling @MaxSterlindh]

@reidgrows exactly, making the money was one skill, but knowing when to stop was a completely different one

[Max Sterling @MaxSterlindh]

@0x_Squirrel the hardest part of building a fortune might be accepting that your kids should eventually control it themselves

[Max Sterling @MaxSterlindh]

In 2015, 92-year-old billionaire Sumner Redstone cut his longtime companion out of his life and changed his estate plans.

Manuela Herzer said he could no longer make decisions for himself. His daughter, Shari, said Herzer was controlling him.

For years, Herzer had been part of Redstone’s inner circle. She lived with him, helped care for him, and was set to receive roughly $70 million in cash and property.

Then Redstone kicked her out.

Herzer took the billionaire to court, claiming he was no longer capable of making his own decisions.

The court later watched an 18-minute video of Redstone’s deposition.

When asked about Herzer, Redstone said:

“Manuela is a fucking bitch.”

He was 92. His media empire was worth roughly $42 billion.

He could control Viacom and CBS. He could not control who stayed in his life.

Was Redstone protecting himself, or was his family taking control of an aging billionaire?

[Max Sterling @MaxSterlindh]

@Pixel_Neuron the scary part is that Dimon isn’t guessing about AI, JPMorgan is already using it at scale and he still expects headcount to fall

[Max Sterling @MaxSterlindh]

@recketino working 12-hour days at 57 after building something worth billions says a lot about how he got there, whether you agree with his approach or not

[Max Sterling @MaxSterlindh]

@builtinlevi he didn’t just invest $5B, he gave everyone around the company a reason to stop panicking

[Max Sterling @MaxSterlindh]

@reidgrows money can be inherited, but knowing what to do with it is a completely different skill