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Steve Jobs was worth over $200 million at 25. He paid his daughter $385 a month.
Her mother cleaned houses and went on welfare. The county had to sue him to pay it back.
In the video below, his daughter Lisa talks about growing up with him.
Jobs was 23 when she was born. He helped pick her name. Then he denied she was his.
A DNA test said he was the father. He told Time magazine that 28% of men in America could be.
The same year, Apple went public. He became one of the richest young men in the country.
He named a computer after her: the Apple Lisa. For years, he refused to admit it.
One day her mother was on the phone with him, sobbing, begging for money. Lisa, a little girl, took the phone and said: “Just give her some money.” Then she hung up.
Another time, her mother asked him for a house. He said yes. Then he bought one for himself.
At 14 she moved in with him. His condition: she couldn’t see her mother for six months.
Years later, he was dying of cancer. She sat by his bed.
“The thing he kept on saying is, ‘I owe you one, and I’m so sorry.’”
Did she forgive him?
“I think not at the time.”
“In many ways, yes.”
When her memoir came out, his widow and his sister released a statement: her story “differs dramatically from our memories.”
The case for Jobs: he was young, he came back, and he tried to make it right before he died.
The case for Lisa: a billionaire’s daughter shouldn’t have grown up on welfare.
He named a computer after her. He wouldn’t say she was his. On his deathbed, he said, “I owe you one.”
Was “I’m sorry” enough, or did it come 30 years too late?
Steve Jobs was worth over $200 million at 25. He paid his daughter $385 a month.
Her mother cleaned houses and went on welfare. The county had to sue him to pay it back.
In the video below, his daughter Lisa talks about growing up with him.
Jobs was 23 when she was born. He helped pick her name. Then he denied she was his.
A DNA test said he was the father. He told Time magazine that 28% of men in America could be.
The same year, Apple went public. He became one of the richest young men in the country.
He named a computer after her: the Apple Lisa. For years, he refused to admit it.
One day her mother was on the phone with him, sobbing, begging for money. Lisa, a little girl, took the phone and said: “Just give her some money.” Then she hung up.
Another time, her mother asked him for a house. He said yes. Then he bought one for himself.
At 14 she moved in with him. His condition: she couldn’t see her mother for six months.
Years later, he was dying of cancer. She sat by his bed.
“The thing he kept on saying is, ‘I owe you one, and I’m so sorry.’”
Did she forgive him?
“I think not at the time.”
“In many ways, yes.”
When her memoir came out, his widow and his sister released a statement: her story “differs dramatically from our memories.”
The case for Jobs: he was young, he came back, and he tried to make it right before he died.
The case for Lisa: a billionaire’s daughter shouldn’t have grown up on welfare.
He named a computer after her. He wouldn’t say she was his. On his deathbed, he said, “I owe you one.”
Was “I’m sorry” enough, or did it come 30 years too late?
Numex retweeted
Dave Chappelle walked away from a $50 million contract. Years later, he said he never got paid for the show that made him famous.
He says the money was never the point.
In the video below, David Letterman asks him if he regrets it.
In 2003, Comedy Central gave him his own sketch show. It became one of the most quoted shows on TV.
In 2004, he signed a two-year deal for seasons three and four. $50 million.
In 2005, in the middle of shooting, he walked off the set and flew to Africa. Almost no one knew where he was.
Letterman asks what happened.
“Technically, I never quit. I’m seven years late for work.”
The trip that started all the rumors? “I was there for two weeks.”
Then Letterman asks the real question: does he regret saying no to that money?
He answers with a story. He is at a nice restaurant with his wife. Across the room sits a man with $100 million.
“We’re eating the same entree.”
“The only difference between having $10 million and $50 million is an astounding $40 million.”
He admits he would like to have it. “Money is the fuel for choices.”
In 2016, Netflix reportedly paid him up to $60 million for a run of stand-up specials.
In 2020, Chappelle’s Show appeared on Netflix. He later said Comedy Central licensed it without paying him. He had signed that contract at 28, broke, with a baby on the way.
He asked fans to stop watching his own show. Netflix pulled it. A few months later, he said Comedy Central had made it right.
The case for Comedy Central: he signed the contract. They offered him $50 million to keep going. He was the one who left in the middle of a season.
He left $50 million on the table. Netflix reportedly paid him $60 million. And he still fought for the show with his name on it.
So was walking away from $50 million the worst decision of his career, or the best one?
Dave Chappelle walked away from a $50 million contract. Years later, he said he never got paid for the show that made him famous.
He says the money was never the point.
In the video below, David Letterman asks him if he regrets it.
In 2003, Comedy Central gave him his own sketch show. It became one of the most quoted shows on TV.
In 2004, he signed a two-year deal for seasons three and four. $50 million.
In 2005, in the middle of shooting, he walked off the set and flew to Africa. Almost no one knew where he was.
Letterman asks what happened.
“Technically, I never quit. I’m seven years late for work.”
The trip that started all the rumors? “I was there for two weeks.”
Then Letterman asks the real question: does he regret saying no to that money?
He answers with a story. He is at a nice restaurant with his wife. Across the room sits a man with $100 million.
“We’re eating the same entree.”
“The only difference between having $10 million and $50 million is an astounding $40 million.”
He admits he would like to have it. “Money is the fuel for choices.”
In 2016, Netflix reportedly paid him up to $60 million for a run of stand-up specials.
In 2020, Chappelle’s Show appeared on Netflix. He later said Comedy Central licensed it without paying him. He had signed that contract at 28, broke, with a baby on the way.
He asked fans to stop watching his own show. Netflix pulled it. A few months later, he said Comedy Central had made it right.
The case for Comedy Central: he signed the contract. They offered him $50 million to keep going. He was the one who left in the middle of a season.
He left $50 million on the table. Netflix reportedly paid him $60 million. And he still fought for the show with his name on it.
So was walking away from $50 million the worst decision of his career, or the best one?
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Martha Stewart was worth over $1 billion. She went to prison over $40,000.
She told Barbara Walters it was “about 0.006% of my net worth.” Then she said: “I don’t think I will be going to prison.”
In the video below, she tells it herself.
She grew up in New Jersey, one of 6 kids in a house with 1 bathroom. She modeled at 13, worked as a stockbroker, then built an empire out of cookbooks, TV, magazines and Kmart. In 1999 she took her company public. “Well over a billion dollars,” she says. America’s first self-made female billionaire.
On December 27, 2001, on her way to Mexico, she got a message from her broker, Peter Bacanovic. ImClone was about to drop. Its CEO, Sam Waksal, who had dated her daughter, was secretly dumping his shares before the government rejected his cancer drug.
She sold that day. “I sold 3,900 shares.” It saved her “approximately $40,000.”
Waksal got 7 years. Then prosecutors came for her, not for the trade, but for lying about it. She stepped down from her own company and watched her stock crash. “My net worth has been cut at least in half.” Barbara put it at $400 to $700 million.
“Of course I’m scared,” she said. “The last place I would ever want to go is to prison.”
In March 2004 she was found guilty on all four counts. In October she reported to a federal prison camp in West Virginia.
The case for Martha: more than 7 million ImClone shares traded that day, and she became the face of it.
The case against her: she wasn’t convicted for selling. She was convicted for lying.
Today she’s 85, rich again, and still says the prosecutors “should have been put in a Cuisinart and turned on high.”
She saved $40,000. She lost up to $700 million. She swore she’d never see prison.
Was she punished for lying, or for being Martha Stewart?
Martha Stewart was worth over $1 billion. She went to prison over $40,000.
She told Barbara Walters it was “about 0.006% of my net worth.” Then she said: “I don’t think I will be going to prison.”
In the video below, she tells it herself.
She grew up in New Jersey, one of 6 kids in a house with 1 bathroom. She modeled at 13, worked as a stockbroker, then built an empire out of cookbooks, TV, magazines and Kmart. In 1999 she took her company public. “Well over a billion dollars,” she says. America’s first self-made female billionaire.
On December 27, 2001, on her way to Mexico, she got a message from her broker, Peter Bacanovic. ImClone was about to drop. Its CEO, Sam Waksal, who had dated her daughter, was secretly dumping his shares before the government rejected his cancer drug.
She sold that day. “I sold 3,900 shares.” It saved her “approximately $40,000.”
Waksal got 7 years. Then prosecutors came for her, not for the trade, but for lying about it. She stepped down from her own company and watched her stock crash. “My net worth has been cut at least in half.” Barbara put it at $400 to $700 million.
“Of course I’m scared,” she said. “The last place I would ever want to go is to prison.”
In March 2004 she was found guilty on all four counts. In October she reported to a federal prison camp in West Virginia.
The case for Martha: more than 7 million ImClone shares traded that day, and she became the face of it.
The case against her: she wasn’t convicted for selling. She was convicted for lying.
Today she’s 85, rich again, and still says the prosecutors “should have been put in a Cuisinart and turned on high.”
She saved $40,000. She lost up to $700 million. She swore she’d never see prison.
Was she punished for lying, or for being Martha Stewart?
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He made $110 million in the NBA. Two years after he retired, he was bankrupt.
His filing showed $4.3 million in assets and $12.7 million in debt. He says nobody stole it from him.
In the video below, he tells it himself.
Antoine Walker grew up in Chicago with nothing. At 20, the Boston Celtics drafted him 6th overall.
3 All-Star games. An NBA title with Miami. 13 seasons.
While he was still playing, he put his name on real estate loans with 7 to 8 banks.
Then 2008 hit. The banks wanted their money back. All at once.
But that wasn’t the only hole.
Private flights. The best hotels. Everywhere he went, his crew went too.
Stephen A. asked how many people he was paying for.
“10 to 15 people. On a consistent basis.”
Not family. Friends.
“How much did they cost you?”
“A couple million dollars.”
“When I made it, I wanted to make sure my guys got to enjoy it too.”
Then Skip Bayless gave him an easy way out. Did he blame his financial advisers?
“No. I blame myself.”
After the bankruptcy, the former All-Star went back to the minor leagues, playing for a fraction of his old salary to pay off what he owed.
Today he talks to young players about money, so they don’t end up like him.
He made $110 million. He owed $12.7 million. He still says it was his fault.
Was he a loyal friend, or did his friends cost him everything?
He made $110 million in the NBA. Two years after he retired, he was bankrupt.
His filing showed $4.3 million in assets and $12.7 million in debt. He says nobody stole it from him.
In the video below, he tells it himself.
Antoine Walker grew up in Chicago with nothing. At 20, the Boston Celtics drafted him 6th overall.
3 All-Star games. An NBA title with Miami. 13 seasons.
While he was still playing, he put his name on real estate loans with 7 to 8 banks.
Then 2008 hit. The banks wanted their money back. All at once.
But that wasn’t the only hole.
Private flights. The best hotels. Everywhere he went, his crew went too.
Stephen A. asked how many people he was paying for.
“10 to 15 people. On a consistent basis.”
Not family. Friends.
“How much did they cost you?”
“A couple million dollars.”
“When I made it, I wanted to make sure my guys got to enjoy it too.”
Then Skip Bayless gave him an easy way out. Did he blame his financial advisers?
“No. I blame myself.”
After the bankruptcy, the former All-Star went back to the minor leagues, playing for a fraction of his old salary to pay off what he owed.
Today he talks to young players about money, so they don’t end up like him.
He made $110 million. He owed $12.7 million. He still says it was his fault.
Was he a loyal friend, or did his friends cost him everything?
Numex retweeted
At 13, she was a meme on Dr. Phil. At 18, she made $1 million on OnlyFans in six hours.
Now the number people ask her about is $75 million.
In the video below, she’s asked if it’s true. She doesn’t argue. She explains how the money arrives.
In 2016, Danielle Bregoli went on Dr. Phil as a “troubled teen.” She told the audience to “cash me outside.”
The clip went viral. She became one of the biggest memes on the internet, and the joke was on her.
She didn’t disappear. She turned the meme into a rap career as Bhad Bhabie.
Then, in April 2021, just over a week after her 18th birthday, she opened an OnlyFans account.
By her own account, she made about $1 million in the first six hours. And about $4 million by the end of the first day.
In 2024, she posted a screenshot: $57 million in net earnings.
So how does that kind of money show up?
“I’m signed to an agency, and they pay me bi-weekly.”
“Every other week.” Direct deposit.
What does she do with it?
“I bought a lot of cars. I bought a lot of houses. I have three houses. I have like seven cars.”
“I don’t really go too crazy.”
The case for the critics: she became famous as a child crying on daytime TV, and the internet never let her forget it. The day she turned 18, the same internet was ready to pay.
The case for Bhabie: everyone made money off her at 13. At 18, she made sure the money finally went to her.
Dr. Phil got the ratings. The internet got the meme. She got the $75 million.
So who really profited from the “cash me outside” girl?
She told them no to porn. Two weeks later, her parents were watching her on Pornhub.
The company behind it reportedly made $17 million. She says she never saw a dime.
In the video below, she tells it herself.
She was 22. A yoga instructor, paying her own way through college with clothed fitness modeling.
The ad on Craigslist said: “Female fitness models wanted, age 18 to 22.”
The website looked professional. She talked to the photographer. She did FaceTime calls with two “reference models” who swore the guys were great.
After about 10 calls, they mentioned they also made adult films. $10,000, instead of “just a couple thousand” for yoga clothing.
“Absolutely not.”
“It’s always an option,” they said.
She flew to San Diego. Her parents had her flight and hotel details.
A black Escalade picked her up at the airport. The doors locked.
They took her purse with her phone in it. In the hotel room, they unplugged the phone and put papers in front of her.
“Sign here. Initial here.”
She asked to read them. “No, no, we have to hurry.”
She says she was raped through the night. When she tried to stop it, they told her:
“We’ll put everything on the internet with your full name, or we’ll send it to your parents. Do you want them to find out?”
Two weeks later, it was online. With her full name.
A boy from high school sent it to her first. Her parents got it from family friends that same night. The link everyone was passing around was on Pornhub.
The company was GirlsDoPorn. Performer Ruben Andre Garcia got 20 years. Prosecutors said owner Michael Pratt made about $17 million before he fled the country.
The women won millions in court. She says she has never seen a dime. She has changed her phone number six times.
“I’ve never done any of this for money.”
They promised her $10,000. They made $17 million. She’s still trying to get the video taken down.
Should the sites that hosted her video pay too, or is a prison sentence enough?
At 13, she was a meme on Dr. Phil. At 18, she made $1 million on OnlyFans in six hours.
Now the number people ask her about is $75 million.
In the video below, she’s asked if it’s true. She doesn’t argue. She explains how the money arrives.
In 2016, Danielle Bregoli went on Dr. Phil as a “troubled teen.” She told the audience to “cash me outside.”
The clip went viral. She became one of the biggest memes on the internet, and the joke was on her.
She didn’t disappear. She turned the meme into a rap career as Bhad Bhabie.
Then, in April 2021, just over a week after her 18th birthday, she opened an OnlyFans account.
By her own account, she made about $1 million in the first six hours. And about $4 million by the end of the first day.
In 2024, she posted a screenshot: $57 million in net earnings.
So how does that kind of money show up?
“I’m signed to an agency, and they pay me bi-weekly.”
“Every other week.” Direct deposit.
What does she do with it?
“I bought a lot of cars. I bought a lot of houses. I have three houses. I have like seven cars.”
“I don’t really go too crazy.”
The case for the critics: she became famous as a child crying on daytime TV, and the internet never let her forget it. The day she turned 18, the same internet was ready to pay.
The case for Bhabie: everyone made money off her at 13. At 18, she made sure the money finally went to her.
Dr. Phil got the ratings. The internet got the meme. She got the $75 million.
So who really profited from the “cash me outside” girl?
Numex retweeted
Ashley Revell sold everything he owned, down to his clothes. Then he put all $135,300 on a single spin of roulette.
The casino said it would never knowingly accept someone’s life savings. Then it took his bet.
In the video below, he stands at the table at the Plaza in Las Vegas.
It was 2004. He was a guy from London with no system, no trick and no edge.
Just one spin. Red or black. Odds a little under 50/50, with the house edge working against him like on every spin.
Before he bets, the casino manager stops him.
“Are you sure you want to make this bet with your life savings?”
He says yes.
The casino makes its position clear: it would never “knowingly condone or accept someone taking a wager of their entire life savings.”
It lets him do it anyway.
Then he freezes.
“What color, then?”
“I don’t know.”
“Oh man, too many decisions.”
He picks red. “Can I kiss it?”
The ball drops. It bounces. It lands on 7.
Red.
$135,300 became $270,600 in a few seconds. He used part of it to start an online poker company.
The case for the casino: he was an adult, he was asked twice, and he signed up for it. A casino’s job is to take bets.
The case against: a casino that says it would never accept someone’s entire life savings still took them. If the ball had landed on black, it would have kept all of it.
The casino said it wouldn’t. He said he was sure. Only one of them meant it.
So was it the dumbest bet in Las Vegas history, or the smartest marketing stunt anyone ever pulled with their life savings?
Chris Tucker was paid about $10,000 to play Smokey in “Friday.” The movie made nearly $28 million.
A few years later, he was reportedly getting $20 million a movie.
In the video below, Shannon Sharpe asks him about it on Club Shay Shay.
“It was just a small movie. We filmed it in 20 days.”
“I got about ten thousand dollars for it or whatever. I didn’t care. I wanted the opportunity.”
The whole movie, he says, cost “either two million or three million.”
There was no money for mistakes.
“We only had two takes. If I mess up one time, you get one more time, and that’s it. We’re gonna cut you out.”
They shot on one street almost the entire time. A few small scenes in a studio. That was it.
“It was just a camera and me and Cube on the porch.”
“And magic came out of it.”
Smokey became one of the most quoted characters in movie history. “Friday” turned into a franchise with two sequels.
Tucker wasn’t in either of them.
Instead, “Rush Hour” made him a global star. For “Rush Hour 2,” he was reportedly paid $20 million.
From $10,000 to $20 million in six years.
The case for the studio: he was an unknown comedian in a tiny movie with a $3 million budget. $10,000 was a normal deal, and he says himself he didn’t care about the money.
The case for Tucker: Smokey is the reason people still quote “Friday” 30 years later. The franchise kept going. His check didn’t.
So was $10,000 fair for Smokey, or did “Friday” owe Chris Tucker a lot more?
Numex retweeted
She told them no to porn. Two weeks later, her parents were watching her on Pornhub.
The company behind it reportedly made $17 million. She says she never saw a dime.
In the video below, she tells it herself.
She was 22. A yoga instructor, paying her own way through college with clothed fitness modeling.
The ad on Craigslist said: “Female fitness models wanted, age 18 to 22.”
The website looked professional. She talked to the photographer. She did FaceTime calls with two “reference models” who swore the guys were great.
After about 10 calls, they mentioned they also made adult films. $10,000, instead of “just a couple thousand” for yoga clothing.
“Absolutely not.”
“It’s always an option,” they said.
She flew to San Diego. Her parents had her flight and hotel details.
A black Escalade picked her up at the airport. The doors locked.
They took her purse with her phone in it. In the hotel room, they unplugged the phone and put papers in front of her.
“Sign here. Initial here.”
She asked to read them. “No, no, we have to hurry.”
She says she was raped through the night. When she tried to stop it, they told her:
“We’ll put everything on the internet with your full name, or we’ll send it to your parents. Do you want them to find out?”
Two weeks later, it was online. With her full name.
A boy from high school sent it to her first. Her parents got it from family friends that same night. The link everyone was passing around was on Pornhub.
The company was GirlsDoPorn. Performer Ruben Andre Garcia got 20 years. Prosecutors said owner Michael Pratt made about $17 million before he fled the country.
The women won millions in court. She says she has never seen a dime. She has changed her phone number six times.
“I’ve never done any of this for money.”
They promised her $10,000. They made $17 million. She’s still trying to get the video taken down.
Should the sites that hosted her video pay too, or is a prison sentence enough?
Bob Arum offered Floyd Mayweather $8 million for his next fight. Mayweather paid Arum $750,000 to let him go.
His next big fight paid him $25 million.
In the video below, he explains why he bought his way out.
It was 2006. Mayweather was signed to Top Rank, Bob Arum’s company. Arum offered him $8 million to fight Antonio Margarito, reportedly double his biggest purse at the time.
Mayweather wanted $20 million to fight Oscar De La Hoya instead. Arum said no.
So Floyd made a move most fighters never make.
“I bet on myself. I bought myself out my contract for 750,000.”
Why pay to leave?
“When I was with a certain promoter, I was in a chokehold. I couldn’t say the things that I wanted to say. I couldn’t be the person that I wanted to be.”
“Then I was able to become my own boss. Promote my fights where I wanted to promote my fights.”
A year later, he fought De La Hoya. He reportedly made $25 million.
Then it kept going. A reported $250 million against Manny Pacquiao. A reported $300 million against Conor McGregor. By most estimates, more than $1 billion over his career.
“You got to make certain sacrifices to get to a certain point.”
The case for Arum: $8 million was a huge offer, and he didn’t think a De La Hoya fight was worth $20 million to Mayweather yet. Promoters take the risk, so they take a cut.
The case for Mayweather: he knew his value before his promoter did. And he was right by about a billion dollars.
One man offered $8 million. The other paid $750,000 to turn it down.
So was Bob Arum wrong about Floyd, or did Floyd just bet bigger than anyone in boxing?
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Chris Tucker was paid about $10,000 to play Smokey in “Friday.” The movie made nearly $28 million.
A few years later, he was reportedly getting $20 million a movie.
In the video below, Shannon Sharpe asks him about it on Club Shay Shay.
“It was just a small movie. We filmed it in 20 days.”
“I got about ten thousand dollars for it or whatever. I didn’t care. I wanted the opportunity.”
The whole movie, he says, cost “either two million or three million.”
There was no money for mistakes.
“We only had two takes. If I mess up one time, you get one more time, and that’s it. We’re gonna cut you out.”
They shot on one street almost the entire time. A few small scenes in a studio. That was it.
“It was just a camera and me and Cube on the porch.”
“And magic came out of it.”
Smokey became one of the most quoted characters in movie history. “Friday” turned into a franchise with two sequels.
Tucker wasn’t in either of them.
Instead, “Rush Hour” made him a global star. For “Rush Hour 2,” he was reportedly paid $20 million.
From $10,000 to $20 million in six years.
The case for the studio: he was an unknown comedian in a tiny movie with a $3 million budget. $10,000 was a normal deal, and he says himself he didn’t care about the money.
The case for Tucker: Smokey is the reason people still quote “Friday” 30 years later. The franchise kept going. His check didn’t.
So was $10,000 fair for Smokey, or did “Friday” owe Chris Tucker a lot more?
Michael Douglas was paid $14 million for “Basic Instinct.” Sharon Stone was paid $500,000.
She says the movie made her a star, and the paycheck couldn’t even cover what came with it.
The video below breaks down what she told an audience in New York.
In 1992, Douglas was already one of the biggest stars in Hollywood, with two Oscars to his name.
Stone was new. “I was new, and he was a very big star.”
The movie became a blockbuster, and overnight, she was famous.
That’s where the money ran out.
“Michael could afford the car, driver, bodyguard,” she said. “I had to move because people were on my roof and breaking my door down.”
Her $500,000 wasn’t enough for the security that her new fame required.
Years later, she says, the film cost her something else. During her divorce, she lost custody of her son, and she says that one scene in the film was used against her.
She says the trauma sent her to the Mayo Clinic with a heart condition.
The case for the studio: Douglas was a proven star with two Oscars. Stone was an unknown. Paying the bankable name more is how Hollywood has always worked.
The case for Stone: the movie made her a household name too, and she carried the consequences for decades. The paycheck stayed the same.
One got $14 million and a bodyguard. The other got $500,000 and people on her roof.
So was $500,000 fair for a newcomer, or did “Basic Instinct” owe Sharon Stone a lot more?