Unpacking financial mechanisms through real stories.
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OkMan retweeted
Rupert Murdoch tried to strip three of his children of voting power in the family trust that controls his media empire.
He wanted to give total control to his eldest son Lachlan after his death. The other three children (James, Elisabeth and Prudence) would have been left with almost no say.
The family trust was created in 1999 during his divorce from his second wife. It gave the four oldest children equal voting rights.
In the video below the reporter explains that Rupert and Lachlan secretly tried to change the trust in court. The judge called it a “carefully crafted charade” and ruled against them.
The empire includes Fox News, News Corp and The Wall Street Journal.
In the video below you hear how deep the family betrayal went.
Was Rupert right to try to protect his empire from his own children, or did he destroy the family in the process?
Antoine Walker made $108 million in the NBA and spent $4.1 million building his mom a 15,000 square foot house with an indoor pool.
When he filed for bankruptcy he asked her what she wanted to do with it.
She told him to let the house go.
In the video below he sits with Brandon Marshall and walks through the moment he broke down. He had four homes at the time and said he could move into a wing of her house until things got straight. She said no. That house was the one thing he built from the ground up and the one thing she gave up.
One side says he spent it trying to live like the rappers he watched growing up. The other side says the real estate deals he guaranteed personally finished what the lifestyle started.
Was the $4.1 million house the part that hurt the most, or was it the fact that she was the one who told him to walk away from it?
Fat Joe got a $10 million deal and pulled $50,000 in cash from the bank every single day.
Thirty guys in his crew got brand new white Cadillac trucks.
One morning the teller at the Chase on 161st told him there was no money left in the account.
He had done it three times. Each time the money came in the same way. The trucks, the chains, the $30,000 dinners, the private planes. Then the account hit zero and he walked out feeling like he got hit without a punch. The next day he collected from everyone who owed him and came back with $250,000.
In the video below he sits with Shannon Sharpe and walks through how the $10 million disappeared. He talks about the IRS leaving him with $49.50 after they calculated what he still owed. He says he is never safe with any amount of money because a million can vanish in a month or two when the bills keep coming.
One side says he spent it on the people around him and that is why it vanished. The other side says the pattern repeated three times because he never stopped the daily cash withdrawals long enough to see the balance.
Was pulling $50,000 every day the reason the $10 million disappeared, or was the real problem that he kept the same crew on payroll the entire time?
Kanye West refused a second year of art school loans that would have cost another $8,000 to $15,000. By the time Charlie Rose interviewed him in 2005 his album The College Dropout had already sold 2.5 million copies and pulled 10 Grammy nominations.
He walked in with a platinum plaque as a producer and a Columbia deal already on the table. His mother put him on $200 a month rent the day he dropped out. The first big beat he sold brought $8,000. The 2002 car crash that wired his jaw shut became the record that finally made Roc-A-Fella sign him as a rapper instead of just a producer.
In the video below he tells Charlie Rose why he walked away from the loans. He says high school is necessary and college is a choice, and that most people sign the debt before they even know what they want.
One side says he left a cheap degree on the table. The other says the loans would have chained him to payments while the music money was already moving.
Was skipping the extra $15,000 in student loans the move that made him, or just the one that looked smart after the album hit?
Richard Branson sold Virgin Records for one billion dollars to keep Virgin Atlantic alive.
In the video below, he explains what that decision felt like.
British Airways was running a dirty tricks campaign against the airline. The bank got nervous. The day after the first Virgin Atlantic flight, the bank manager came to his house and told him to sell the record company. He pushed the man out the door. That was not smart. The bank owned the house through the mortgage.
He realized they were running out of options. Selling the record company would give the cash to save the airline and protect the Virgin brand. Thorn EMI offered about one billion dollars. Friends and artists, including Peter Gabriel, told him not to do it. He still signed the papers at three in the morning.
The next day the sale was announced. He ran down the street with tears streaming down his face and saw a headline that said Branson sells for a billion. A couple of weeks later they won the biggest libel damages in British history against British Airways. He says he would not be building spaceships today if he had not sold the record company.
Bill Gates told Satya Nadella he was about to burn $1 billion on OpenAI.
Six years later, after committing $13 billion, Microsoft’s stake was valued at $135 billion.
In 2019 OpenAI had no commercial product. Sam Altman came to Microsoft arguing that models trained on more and more text would keep getting smarter. That July Nadella signed the first check.
Microsoft’s own co-founder thought the money was gone. As Nadella told TBPN, Gates even said, “yeah, you’re going to burn this billion dollars.”
Gates doubted that a neural network could learn real knowledge just by reading. Microsoft put in more money anyway.
In mid-2022 the skeptic set OpenAI a test of his own. Train a model to pass the AP Biology exam, he said, expecting the job to take two or three years. OpenAI was done in a few months.
That September he watched it answer 59 of 60 multiple-choice questions correctly and earn a 5, the top score. The next spring he described that moment in an essay.
“I knew I had just seen the most important advance in technology since the graphical user interface.”
In the video below Nadella talks about the moment Gates warned him the money would be wasted.
Have you ever backed an unproven idea with serious money you were prepared to lose?
Elon Musk had about $30 to $40 million left in 2008. He could put it all into one company and the other would die, or split it and risk losing both.
In the video below, he explains the choice.
2008 was brutal. SpaceX had the third consecutive failure of the Falcon rocket. Tesla almost went bankrupt. They closed the financing round at 6 p.m. on Christmas Eve. It was the last hour of the last day that it was possible. They would have gone bankrupt two days after Christmas otherwise. He also got divorced that year.
SpaceX is alive by the skin of its teeth. So is Tesla. If things had just gone a little bit the other way, both companies would be dead. One of the most difficult choices he ever faced in life was in 2008. He had two choices. Put it all into one company and then the other company would definitely die. Or split it between the two companies. But if he split it between the two companies, then both might die.
When you put your blood, sweat, and tears into creating something, building something, it is like a child. Which one was he going to let starve to death? He could not bring himself to do it, so he split the money between the two. Fortunately, they both came through.
Eminem needed the five hundred dollar first prize at the Rap Olympics so badly that losing felt like his manhood was stripped away.
In the video below, he explains what happened the night before.
The day before he flew to Los Angeles, he came home from work and found all their stuff thrown on the lawn. People were already going through it. The guy they paid rent to had not been paying the actual rent.
He had nowhere to stay, so he broke in through the back window, slept on the floor with no heat and no power, and used his cell phone as an alarm so he would not miss the flight. Wendy Day had paid for the plane ticket.
He made it to the final. He beat everybody until the last round and then choked a little. The prize was five hundred dollars and a Rolex. He did not care about the watch. He needed the cash.
When he lost, he was devastated. Then a kid named Dean Geistlinger walked up and asked if he had one of those CDs. He tossed him one without thinking. Dean worked with Jimmy Iovine. Jimmy gave it to Dr. Dre.
A few weeks later he got the call while he was still in Detroit with nothing and nowhere to go.
OkMan retweeted
Steve Jobs was worth over a million dollars at 23, over ten million at 24, and over a hundred million at 25.
In the video below, he explains what that actually felt like.
He said it was not that important because he never did it for the money. The most important thing was the company, the people, and the products they were making. He never sold any stock. He just believed the company would do well over the long term.
OkMan retweeted
Offset said labels gave him a $2 million advance and five albums. Then he explained why most of that money never stayed his.
In the video below, he explains what happened.
He said when he was 20 they handed him the check and he signed. He did not read the terms. The first month the album did $2–3 million. That money did not count toward what he owed them. They still had him in debt while they recouped.
He said the lawyer tells you to take the money. Nobody breaks down the deliverables or how long they own you. The advance was real. The ownership of the records was not.
He found out who controlled the money after the check cleared.
Offset said labels gave him a $2 million advance and five albums. Then he explained why most of that money never stayed his.
In the video below, he explains what happened.
He said when he was 20 they handed him the check and he signed. He did not read the terms. The first month the album did $2–3 million. That money did not count toward what he owed them. They still had him in debt while they recouped.
He said the lawyer tells you to take the money. Nobody breaks down the deliverables or how long they own you. The advance was real. The ownership of the records was not.
He found out who controlled the money after the check cleared.
OkMan retweeted
Fetty Wap took out $100,000 one day. When he went back to the bank there was a hold on the account. He was broke for six months.
In the video below, he explains what happened.
He said he went to the bank again and they told him there was a hold. He called another account and they said they needed to talk to him. It was not taxes. People he did not even know he had to pay had frozen everything. He was spending $150,000 a month in bills. He had four apartments in New Jersey, two in Miami, a couple in Los Angeles, plus houses. He did not like hotels because people could just knock on the door.
He said he was clearing $100,000 every day. The day he woke up and only made $40,000 he knew something was wrong. Bookings dropped to $50,000 and then $30,000. He was traveling with 14, 15, sometimes 30 people. Nobody said anything because they were getting paid. He called them yes men.
He said the most he ever saw in the account was $22 million. It was not from one check. It was shows, features, and pieces of businesses. He still could not touch the money for six months. The same people who helped put it there put the holds on it.
He found out the same way most people do: when he tried to take it out.
A founder sold his company for $1.5 billion. Nestlé bought it. Then they shut it down.
In the video below, he explains what happened.
He said he had $15 in the bank and a $1 million judgment against him when he started. Six years later the company was doing over $500 million in revenue and more than a million meals a week. Nestlé paid $950 million up front plus a $550 million earn-out. He took home roughly $100 million before taxes.
He said if it’s your baby, you don’t sell your kids. About a year after he stepped away, Nestlé closed Freshly. The thing he spent nearly a decade building was gone.
He did not take time off. He put almost all the money into the next company. The sale price was real. The control was not. He found out who owned the outcome after the wire hit.
OkMan retweeted
Ray Dalio had to borrow $4,000 from his dad in 1982.
He had calculated that American banks had lent too much money to emerging countries. Mexico defaulted that August. He thought the stock market and the economy would fall hard.
He was right about the debt crisis. He was wrong about what the market would do. Stocks went up. He lost money for himself and for his clients.
He had a small firm then. He had to let people go. He was so broke he called his father for $4,000 to cover family bills.
In the video below he calls it one of the most painful experiences of his life and also the best thing that ever happened to him.
It changed how he thinks. He went from “I know” to “how do I know.”
Would you rather be right and go broke, or be wrong once and keep the ability to come back?
OkMan retweeted
In 2003 Keanu Reeves gave 75 million dollars to the Matrix crew. His daughter had been dead for 4 years.
In the video below Keanu Reeves in 2003.
Keanu Reeves was born in Beirut in 1964. His Hawaiian-Chinese father abandoned the family when he was 3. His mother raised him and his sister Kim in Toronto. He was dyslexic and dropped out of high school.
In 1999 Keanu earned 10 million dollars for the first Matrix. On December 24 that year his daughter Ava was born stillborn. He and his girlfriend Jennifer Syme broke up weeks later from grief.
In April 2001 Jennifer died in a car crash in Los Angeles. Keanu was in the middle of shooting Matrix Reloaded and Revolutions. He finished both films.
In 2003 after the sequels released Keanu collected his backend share from the films.
Reports said he redirected roughly 75 million dollars to the special effects and costume teams. He bought twelve Harley-Davidsons for his stunt doubles.
His sister Kim had already been fighting leukemia for years. He paid for much of her treatment.
He never confirmed the numbers publicly. The crew members talked.
In 2026 Keanu is worth around 400 million dollars and still lives in a rented apartment.
The man who lost his daughter and his girlfriend in 2 years handed the people who made his movies possible a share of everything that came after.
Would you give away half your fortune to the strangers who built the thing that made you rich?
OkMan retweeted
50 Cent has spent $24 million on legal fees in his career. He does not have a manager. He has general counsel.
In the video below, he explains why.
He said when people agitate him he sends the lawyers. He does it for recreational purposes. He spends a million a year easily on legal fees. He has already done every deal a hundred times. He does not need someone taking a percentage to manage him.
He said they all want to work at a percentage. You want a percentage of me? You did not build this. I built it.
The same structure that lets him control the business also lets him use lawsuits as a tool. The $24 million is the cost of keeping that control.
Fetty Wap took out $100,000 one day. When he went back to the bank there was a hold on the account. He was broke for six months.
In the video below, he explains what happened.
He said he went to the bank again and they told him there was a hold. He called another account and they said they needed to talk to him. It was not taxes. People he did not even know he had to pay had frozen everything. He was spending $150,000 a month in bills. He had four apartments in New Jersey, two in Miami, a couple in Los Angeles, plus houses. He did not like hotels because people could just knock on the door.
He said he was clearing $100,000 every day. The day he woke up and only made $40,000 he knew something was wrong. Bookings dropped to $50,000 and then $30,000. He was traveling with 14, 15, sometimes 30 people. Nobody said anything because they were getting paid. He called them yes men.
He said the most he ever saw in the account was $22 million. It was not from one check. It was shows, features, and pieces of businesses. He still could not touch the money for six months. The same people who helped put it there put the holds on it.
He found out the same way most people do: when he tried to take it out.
Barbara Corcoran borrowed $1,000 to start a real estate company. She sold it for $66 million.
In the video below, she explains how it happened.
She was a waitress at the Fort Lee Diner. A man came in, ordered tea, and became her boyfriend. He loaned her $1,000 and told her to start a real estate business. She had already had 22 jobs. She figured the worst that happens is she goes back to the diner.
He left her for her secretary and told her she would never succeed without him. She said thank God he said that. Every time she was out of money and thought she was going down, she thought of those words. She sold the business for $66 million about 20 years later. He was out of business in three years.
The first offer that came in was $22 million. She was on a chairlift with her brother. He said take the money and run. She said no. She asked for $66 million because it was her lucky number. They paid it.
OkMan retweeted
Thor Bjorgolfsson lost 99% of a $4 billion fortune in 18 months.
In the video below, he says how it felt.
In 2007 he was worth about $3.5 billion. Iceland’s first billionaire. Ranked 249th in the world. Then 2008 hit. His bank, Landsbanki, collapsed. The government seized it. His companies owed billions. He had personally guaranteed about $1 billion of the debt.
He says the years from 2002 to 2008 were too fast. Deals came too easy. His net worth went from $100 million to $3.5 billion. Then the other way. After the collapse he was in the gray area. Somewhere near zero. Or below it.
He did not declare bankruptcy. He spent years negotiating with creditors. Bricks were thrown through his window in Iceland. He was treated like the man who had helped bring down the country.
He is a billionaire again. The 99% did not come back the same way.
Was the loss the price of building a bank in a country too small for the bets he made, or proof that a man who can lose $4 billion and sit there talking about it was never playing with money he could not replace?