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Mark retweeted
Dr. Dre’s wife asked for $1,936,399 a month in spousal support. She ended up receiving about $293,000 a month in temporary support.
They had been married for 24 years. She said the prenup didn’t count.
She said she signed it under duress, and that Dre “tore up multiple copies of the agreement in front of me.”
Her filing said he was worth $1 billion. Forbes put him at $800 million in 2019. Apple had bought Beats for $3 billion.
The court papers described their life: five homes in L.A., a private jet, 12 security guards, seven housekeepers, a private chef. She also asked for $5 million for her lawyers.
In October 2021, a process server came after him at the cemetery where he was burying his grandmother.
Two months later, they settled. $100 million: $50 million right away, $50 million a year later. According to E! News, she also kept a Rolls-Royce, an Escalade limo, a Range Rover, a motorcycle, and her jewelry and furs. He kept the houses, his music and his stock.
In the video below, from 2014, Dre celebrates the reported Apple deal: “The first billionaire in hip hop, right here from the West Coast.”
The case for Nicole: 24 years, and she says she helped name his label, Aftermath.
The case for Dre: she signed a prenup, and still walked away with $100 million.
Was $100 million fair for 24 years, or should she have gotten half?
Dr. Dre’s wife asked for $1,936,399 a month in spousal support. She ended up receiving about $293,000 a month in temporary support.
They had been married for 24 years. She said the prenup didn’t count.
She said she signed it under duress, and that Dre “tore up multiple copies of the agreement in front of me.”
Her filing said he was worth $1 billion. Forbes put him at $800 million in 2019. Apple had bought Beats for $3 billion.
The court papers described their life: five homes in L.A., a private jet, 12 security guards, seven housekeepers, a private chef. She also asked for $5 million for her lawyers.
In October 2021, a process server came after him at the cemetery where he was burying his grandmother.
Two months later, they settled. $100 million: $50 million right away, $50 million a year later. According to E! News, she also kept a Rolls-Royce, an Escalade limo, a Range Rover, a motorcycle, and her jewelry and furs. He kept the houses, his music and his stock.
In the video below, from 2014, Dre celebrates the reported Apple deal: “The first billionaire in hip hop, right here from the West Coast.”
The case for Nicole: 24 years, and she says she helped name his label, Aftermath.
The case for Dre: she signed a prenup, and still walked away with $100 million.
Was $100 million fair for 24 years, or should she have gotten half?
Mark retweeted
SoftBank sold a stake in Nvidia worth about $3.6 billion in 2019. By late 2024, the same 4.9% would have been worth about $178 billion.
Nvidia had just had a bad quarter. SoftBank sold all of it.
Then AI happened.
“The fish that got away was big,” Masayoshi Son said in 2024.
That wasn’t even his biggest miss.
In the video below, Jensen Huang tells a packed room what Son offered him ten years ago. To lend him the money to buy Nvidia. All of it.
“Now I regret not taking it.”
Earlier on the same stage, Huang says Son was once Nvidia’s largest shareholder: “We can cry together.”
In October 2025, SoftBank sold its Nvidia shares again. 32.1 million shares, about $5.8 billion.
The case for Son: he locked in a profit after a bad quarter. That’s what investors are supposed to do.
The case against: he sold the most important company of the AI era. Twice.
Would you have sold after a bad quarter, or held on?
SoftBank sold a stake in Nvidia worth about $3.6 billion in 2019. By late 2024, the same 4.9% would have been worth about $178 billion.
Nvidia had just had a bad quarter. SoftBank sold all of it.
Then AI happened.
“The fish that got away was big,” Masayoshi Son said in 2024.
That wasn’t even his biggest miss.
In the video below, Jensen Huang tells a packed room what Son offered him ten years ago. To lend him the money to buy Nvidia. All of it.
“Now I regret not taking it.”
Earlier on the same stage, Huang says Son was once Nvidia’s largest shareholder: “We can cry together.”
In October 2025, SoftBank sold its Nvidia shares again. 32.1 million shares, about $5.8 billion.
The case for Son: he locked in a profit after a bad quarter. That’s what investors are supposed to do.
The case against: he sold the most important company of the AI era. Twice.
Would you have sold after a bad quarter, or held on?
Mark retweeted
Robert De Niro cut his estranged wife’s credit card limit from $100,000 a month to $50,000. His lawyer told the court the pandemic had hurt his restaurants.
Her lawyer said he was worth $500 million and made $30 million a year.
They first married in 1997, split, got back together in 2004, and signed a prenup. In 2018, he filed for divorce.
The prenup: $1 million a year to her. But only in years he earns $15 million or more.
His lawyer said he’d be “lucky if he makes $7.5 million this year.” The Nobu restaurants he co-owns lost $3 million in April and $1.87 million in May. He borrowed $500,000 from partners to pay investors.
Her lawyer said the story about him tightening his belt didn’t add up.
For now, the judge kept the card at $50,000. And ordered him to pay her $75,000 for a summer home for their kids.
Three years later, at 79, De Niro welcomed his seventh child with his girlfriend, Tiffany Chen.
In the video below, he’s asked how fatherhood feels at his age: “It feels great.”
The case for Grace: two decades together, two kids, and a husband her lawyer valued at $500 million.
The case for Bob: she signed the prenup, and his restaurants were losing millions a month.
Was cutting her card to $50,000 fair, or did he use the pandemic as an excuse?
Robert De Niro cut his estranged wife’s credit card limit from $100,000 a month to $50,000. His lawyer told the court the pandemic had hurt his restaurants.
Her lawyer said he was worth $500 million and made $30 million a year.
They first married in 1997, split, got back together in 2004, and signed a prenup. In 2018, he filed for divorce.
The prenup: $1 million a year to her. But only in years he earns $15 million or more.
His lawyer said he’d be “lucky if he makes $7.5 million this year.” The Nobu restaurants he co-owns lost $3 million in April and $1.87 million in May. He borrowed $500,000 from partners to pay investors.
Her lawyer said the story about him tightening his belt didn’t add up.
For now, the judge kept the card at $50,000. And ordered him to pay her $75,000 for a summer home for their kids.
Three years later, at 79, De Niro welcomed his seventh child with his girlfriend, Tiffany Chen.
In the video below, he’s asked how fatherhood feels at his age: “It feels great.”
The case for Grace: two decades together, two kids, and a husband her lawyer valued at $500 million.
The case for Bob: she signed the prenup, and his restaurants were losing millions a month.
Was cutting her card to $50,000 fair, or did he use the pandemic as an excuse?
Mark retweeted
Steve Jobs told his best friend they got $700 for a job. He gave Steve Wozniak $350.
Atari had also paid a $5,000 bonus. Jobs kept it secret.
The job was Breakout. Jobs promised Atari the game in four days. Woz designed it in four nights while still working his day job at Hewlett-Packard. They barely slept. Both got mononucleosis.
Woz found out about the bonus years later.
In 1980, Apple went public and made Woz a multimillionaire.
Then he did the opposite of Jobs. He offered part of his own Apple shares, at a low price, to early employees who had been left out.
In the video below, Woz tells another story. He says Jobs saw a remote control Woz was building at his new company, threw it against the wall and said: “I own everything you do.”
“What decent human being could ever do something that way?”
The case for Jobs: Woz himself says Jobs would take his inventions and “turn it into money for both of us.” Without him, there might be no Apple.
The case against: he lied to his best friend over a few thousand dollars.
Would you have stayed partners with him after finding out?
Steve Jobs told his best friend they got $700 for a job. He gave Steve Wozniak $350.
Atari had also paid a $5,000 bonus. Jobs kept it secret.
The job was Breakout. Jobs promised Atari the game in four days. Woz designed it in four nights while still working his day job at Hewlett-Packard. They barely slept. Both got mononucleosis.
Woz found out about the bonus years later.
In 1980, Apple went public and made Woz a multimillionaire.
Then he did the opposite of Jobs. He offered part of his own Apple shares, at a low price, to early employees who had been left out.
In the video below, Woz tells another story. He says Jobs saw a remote control Woz was building at his new company, threw it against the wall and said: “I own everything you do.”
“What decent human being could ever do something that way?”
The case for Jobs: Woz himself says Jobs would take his inventions and “turn it into money for both of us.” Without him, there might be no Apple.
The case against: he lied to his best friend over a few thousand dollars.
Would you have stayed partners with him after finding out?
Mark retweeted
Anna Nicole Smith was 26 when she married 89-year-old oil billionaire J. Howard Marshall. He died 403 days later. One court awarded her about $474 million. She ended up with $0.
They married on June 27, 1994. He died on August 4, 1995. His estate, reported at $1.6 billion, went through his trust and will to his son, E. Pierce Marshall.
She said her husband had promised her half. The will left her nothing beyond an estimated $6 million in lifetime gifts.
Table 1 shows how the fight went. In 2000, a California bankruptcy court ruled for her: more than $449 million, plus $25 million in punitive damages.
In 2002, a federal judge cut it to $88,585,534.66.
Watch Fig. 1. The number drops to $0 in 2004, comes back after a 9-0 Supreme Court win in 2006, then drops to $0 again.
Pierce died about a month after that ruling. She died in 2007. Their estates kept fighting.
In 2011, the Supreme Court ruled 5-4 against her. In 2014, a federal judge rejected her estate’s last claim. 19 years. Two Supreme Court cases. Zero dollars.
The math makes it worse. Had the $88.6 million been paid in 2002 and invested in the S&P 500, it would have grown to about $908 million by 2024.
The case for Pierce: a Texas jury upheld his father’s estate plan, and he was a son defending it.
Here’s the lesson: a promise that isn’t in the will is worth exactly what the will says.
If your 89-year-old father married a 26-year-old, would you fight her in court for 19 years?
The $474 Million Zero
Inheritance, Litigation and the Time Value of a Judgment
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Mark retweeted
In 1975, Sylvester Stallone was so broke he sold his dog.
Then a studio offered him $360,000 for his script. One condition: someone else would play the lead.
He said no.
He tells it himself in the video below.
He was working as an usher. “36 dollars a week. That was it.”
The studio wanted bankable names. Burt Reynolds. Robert Redford.
“I said no, no, I don’t think so.”
At home there was no money for food. “One of us doesn’t eat. My wife or the dog.”
He sold the dog.
“If you make the wrong decision, sometimes you regret it forever.”
The studio gave in. Rocky was made for about $1 million. It made more than $225 million and won Best Picture.
When the money came, he went back for his dog. The man who bought it wouldn’t give it back. So Stallone put him in the movie.
He turned down $360,000 to bet on himself.
Would you have taken the money?
In 1975, Sylvester Stallone was so broke he sold his dog.
Then a studio offered him $360,000 for his script. One condition: someone else would play the lead.
He said no.
He tells it himself in the video below.
He was working as an usher. “36 dollars a week. That was it.”
The studio wanted bankable names. Burt Reynolds. Robert Redford.
“I said no, no, I don’t think so.”
At home there was no money for food. “One of us doesn’t eat. My wife or the dog.”
He sold the dog.
“If you make the wrong decision, sometimes you regret it forever.”
The studio gave in. Rocky was made for about $1 million. It made more than $225 million and won Best Picture.
When the money came, he went back for his dog. The man who bought it wouldn’t give it back. So Stallone put him in the movie.
He turned down $360,000 to bet on himself.
Would you have taken the money?
Mark retweeted
Steve Jobs paid $385 a month for the daughter he swore he couldn’t have.
Then Apple went public. He was worth more than $200 million.
The signed court document said he was “sterile and infertile.”
A DNA test put the probability that he was Lisa’s father at 94.1%. He told TIME magazine that “28% of the male population of the United States could be the father.”
While he denied her, her mother cleaned houses and went on welfare.
At the same time, Apple was building a computer called the Lisa. He called the name a coincidence. Decades later: “Obviously, it was named for my daughter.”
In the video below, Lisa remembers the day her mother read what he said about them in TIME. “We had no money.” Then she describes his last weekend.
He cried, apologized, and kept repeating, “I owe you one.” He left her millions.
The case for Steve: he was 23, he came back, and he made it right in the end.
The case against: millions in a will don’t buy back a childhood on welfare.
Did he make it right, or just run out of time?
Steve Jobs paid $385 a month for the daughter he swore he couldn’t have.
Then Apple went public. He was worth more than $200 million.
The signed court document said he was “sterile and infertile.”
A DNA test put the probability that he was Lisa’s father at 94.1%. He told TIME magazine that “28% of the male population of the United States could be the father.”
While he denied her, her mother cleaned houses and went on welfare.
At the same time, Apple was building a computer called the Lisa. He called the name a coincidence. Decades later: “Obviously, it was named for my daughter.”
In the video below, Lisa remembers the day her mother read what he said about them in TIME. “We had no money.” Then she describes his last weekend.
He cried, apologized, and kept repeating, “I owe you one.” He left her millions.
The case for Steve: he was 23, he came back, and he made it right in the end.
The case against: millions in a will don’t buy back a childhood on welfare.
Did he make it right, or just run out of time?
Mark retweeted
Taylor Swift paid a reported $360 million for songs she wrote herself.
At 15, she signed a record deal that let the label own her recordings.
At 29, a man she says bullied her for years bought them all.
At 35, she bought them back.
Six albums. Every hit from “Love Story” to “Shake It Off.”
When her contract ended, she tried to buy them. She says the label offered to let her “earn” one old album back for every new one she made.
She walked away. Months later, Big Machine Records was sold to Scooter Braun’s company for about $300 million. Her masters came with it.
In the video below, she tells a room full of music executives what happened. Listen for the line “he could buy me.”
So she re-recorded her old albums from scratch and asked fans to stream “Taylor’s Version” instead. They did.
The case for Scooter. He bought a company, not a person. Almost every new artist signs away their masters. That’s the business.
Do the math. $360 million for six albums. $60 million for each album she had already written and sung.
Here’s the lesson. If you don’t own what you make, someone else can sell it.
Would you sign a deal at 15 that gives away everything you create, or stay unknown and keep it?
Taylor Swift paid a reported $360 million for songs she wrote herself.
At 15, she signed a record deal that let the label own her recordings.
At 29, a man she says bullied her for years bought them all.
At 35, she bought them back.
Six albums. Every hit from “Love Story” to “Shake It Off.”
When her contract ended, she tried to buy them. She says the label offered to let her “earn” one old album back for every new one she made.
She walked away. Months later, Big Machine Records was sold to Scooter Braun’s company for about $300 million. Her masters came with it.
In the video below, she tells a room full of music executives what happened. Listen for the line “he could buy me.”
So she re-recorded her old albums from scratch and asked fans to stream “Taylor’s Version” instead. They did.
The case for Scooter. He bought a company, not a person. Almost every new artist signs away their masters. That’s the business.
Do the math. $360 million for six albums. $60 million for each album she had already written and sung.
Here’s the lesson. If you don’t own what you make, someone else can sell it.
Would you sign a deal at 15 that gives away everything you create, or stay unknown and keep it?
Mark retweeted
Paul McCartney told Michael Jackson to buy song catalogs. So Michael bought Paul’s. For $47.5 million.
Michael’s estate later sold just half of it for $750 million.
They were friends. They recorded “The Girl Is Mine” and “Say Say Say” together. Paul explained to Michael how much money there was in owning songs.
Michael joked that one day he would own Paul’s.
In 1985 he did. He bought ATV Music, which owned 251 Beatles songs.
In the video below, Paul tells Howard Stern how it felt.
His verdict: “To be someone’s friend, and then buy the rug they’re standing on.”
Years later, Paul wrote to Michael asking for a better royalty deal. Michael’s answer: “Oh Paul, that’s just business.”
The case for Michael. Paul and Yoko Ono were approached before the sale and said they wouldn’t bid. Michael simply paid. As he wrote later: “Paul and I both learned the hard way about business.”
Do the math. A decade later Michael sold half of the catalog to Sony for $95 million. In 2016 his estate sold the other half for $750 million. That’s about $845 million from a $47.5 million deal. Roughly 18 times the money.
Paul’s line on buying his own songs back: “I wrote those songs for nothing and buying them back at these phenomenal sums, I just can’t do it.”
Here’s the lesson. Never teach a friend how to get rich off the thing you own.
If a friend’s advice made you rich, do you owe him anything?
Follow for more money stories from behind the world’s biggest names.
Paul McCartney told Michael Jackson to buy song catalogs. So Michael bought Paul’s. For $47.5 million.
Michael’s estate later sold just half of it for $750 million.
They were friends. They recorded “The Girl Is Mine” and “Say Say Say” together. Paul explained to Michael how much money there was in owning songs.
Michael joked that one day he would own Paul’s.
In 1985 he did. He bought ATV Music, which owned 251 Beatles songs.
In the video below, Paul tells Howard Stern how it felt.
His verdict: “To be someone’s friend, and then buy the rug they’re standing on.”
Years later, Paul wrote to Michael asking for a better royalty deal. Michael’s answer: “Oh Paul, that’s just business.”
The case for Michael. Paul and Yoko Ono were approached before the sale and said they wouldn’t bid. Michael simply paid. As he wrote later: “Paul and I both learned the hard way about business.”
Do the math. A decade later Michael sold half of the catalog to Sony for $95 million. In 2016 his estate sold the other half for $750 million. That’s about $845 million from a $47.5 million deal. Roughly 18 times the money.
Paul’s line on buying his own songs back: “I wrote those songs for nothing and buying them back at these phenomenal sums, I just can’t do it.”
Here’s the lesson. Never teach a friend how to get rich off the thing you own.
If a friend’s advice made you rich, do you owe him anything?
Follow for more money stories from behind the world’s biggest names.
Mark retweeted
Dolly Parton’s fortune was estimated at $450 million. Less than a month after she died, her estate got a restraining order against her own nephew.
He was the man who announced her death to the world.
Bryan Seaver had been her head of security for years. In the family video, he called it “an honor that is mixed with absolute pride and great sadness.”
On September 15, her longtime manager fired him. Then the texts came out. According to the court filing:
“Her money better be bigger than I can make elsewhere or I’m going to f*** everyone.”
“I’m going to set up a podcast dedicated to ruining Dolly’s brand partnerships.”
“I’m not an entertainment person. I’m a killer.”
The filing says staff avoided the office and needed personal security.
The case for Seaver. He says it was “rage talk” between two grieving friends, taken out of context. This week he told the court he was angry over more than $250,000 he says he was owed for work he’d already done. He attached a 2024 letter from Dolly praising him.
In the video below, he gives his side. The judge hears both next week.
Do the math. $250,000 is about 0.06% of Dolly’s estimated fortune. That’s what he says this whole fight is about.
Here’s the lesson. The biggest threat to a fortune is rarely a stranger. It’s family on the payroll.
Was he a grieving nephew who got stiffed, or a man trying to cash in on his aunt’s name?
Dolly Parton’s fortune was estimated at $450 million. Less than a month after she died, her estate got a restraining order against her own nephew.
He was the man who announced her death to the world.
Bryan Seaver had been her head of security for years. In the family video, he called it “an honor that is mixed with absolute pride and great sadness.”
On September 15, her longtime manager fired him. Then the texts came out. According to the court filing:
“Her money better be bigger than I can make elsewhere or I’m going to f*** everyone.”
“I’m going to set up a podcast dedicated to ruining Dolly’s brand partnerships.”
“I’m not an entertainment person. I’m a killer.”
The filing says staff avoided the office and needed personal security.
The case for Seaver. He says it was “rage talk” between two grieving friends, taken out of context. This week he told the court he was angry over more than $250,000 he says he was owed for work he’d already done. He attached a 2024 letter from Dolly praising him.
In the video below, he gives his side. The judge hears both next week.
Do the math. $250,000 is about 0.06% of Dolly’s estimated fortune. That’s what he says this whole fight is about.
Here’s the lesson. The biggest threat to a fortune is rarely a stranger. It’s family on the payroll.
Was he a grieving nephew who got stiffed, or a man trying to cash in on his aunt’s name?
Mark retweeted
Johnny Depp’s ex-managers said he spent $30,000 a month on wine.
Depp said that was insulting. Because it was far more.
He earned about $650 million from his movies. They said he was spending over $2 million a month. By 2018, almost all of it was gone.
According to his ex-managers:
14 homes worth $75 million.
$18 million on a 150-foot yacht.
$10 million supporting friends, family and employees.
Over $3 million to fire Hunter S. Thompson’s ashes out of a cannon.
Depp corrected that one too:
“It was not $3 million to shoot Hunter into the f***ing sky. It was $5 million.”
He sued them for $25 million. He said they took a 5% cut even when he didn’t get paid. They said: “Johnny Depp alone was solely responsible for his extravagant spending.”
In the video below, Depp in court, on the subject of wine.
Here’s the lesson. Making $650 million doesn’t make you rich. Keeping it does.
So who lost Johnny Depp’s fortune: the managers, or Johnny?