Billionaire Tyler Perry gave his own family 60 days to find jobs or lose his financial support. Despite being worth an estimated $1.4 billion, he refused to keep supporting relatives who weren't working. In the video below, Perry explains why he fired his own aunt and later gave other family members an ultimatum after his mother's death. He wanted them to become financially independent instead of relying on his fortune. One aunt regularly called asking for money, and Perry kept sending it until he offered her a job. But she repeatedly called in and failed to show up for work, so he eventually fired her. His mother had also asked him to support other relatives, and he continued helping them while she was alive. After she died in 2009, Perry sent them letters giving them 60 days to find employment or lose his financial support. According to Perry, every relative eventually found a job. He didn't care whether the jobs paid well because he wanted them to earn their own money and have something to feel proud of. Perry also recalled a relative getting angry when he refused to hand over $1 million. He believed that continually giving money to people who refused to work was making their dependence worse. A billionaire who could afford to support his entire family chose to make them earn their own living. If you had $1.4 billion, would you keep supporting unemployed relatives or give them the same 60-day ultimatum?

50 Cent says he was paying his son's mother $500,000 a year, but she kept demanding more. So he took himself to child support court and ended up paying just $6,700 a month. In the video below, 50 Cent explains why he went to court voluntarily and how the money dispute damaged his relationship with his oldest son, Marquise. He questions why his son went to TMZ instead of contacting him privately. According to the rapper, he was voluntarily giving Shaniqua Tompkins half a million dollars annually to support their son. When she continued asking for more, he decided to let the court determine how much he was legally required to pay. The amount dropped to $6,700 a month, roughly $80,000 a year. But the conflict continued long after the payments were settled, and father and son eventually became estranged. In 2022, Marquise publicly complained that $6,700 a month wasn't enough to maintain his lifestyle in New York. After being criticized, he offered his father that same $6,700 for just 24 hours together. Instead of reaching out privately, Marquise took his story to TMZ, saying he wanted to rebuild their relationship. 50 Cent questioned why his son chose a public interview over a phone call and accused him of seeking attention, while Marquise insisted he simply wanted his father back in his life. A father who once provided $500,000 a year and a son willing to pay $6,700 for one day together ended up arguing about money in public. Was 50 Cent right to take the dispute to court, or should a wealthy father be expected to provide more for his child?

Steve Jobs refused to give Apple stock to the friend who helped build its first computers. In the video below, Daniel Kottke describes trying to get Jobs to sit down for lunch and discuss a stake in the company he had been part of from day one. They had met in college, traveled through India together and shared a house. Kottke worked on the first Apple computers, but his title was technician, which made him ineligible for stock options. He says he wanted Jobs to explain what he needed to do to earn a stake someday. He repeatedly asked to meet over lunch, but Jobs would not have the conversation. Five years after Apple’s IPO, Kottke finally received shares from the other Steve, Wozniak, who felt the early employees left out deserved a stake. Kottke says the gift was worth only about 10% of what a typical early engineer had received, but he held onto the shares until they were worth millions. Does this show what kind of person Jobs was, or was he simply keeping friendship out of business and shouldn’t be judged for it?

Bill Gates is worth over $100 billion. He said his three children will receive less than 1% of it. In the video below, he explains why. “It’s not a favor to kids to have them have huge sums of wealth because it distorts anything they might do.” He said they will get a great education and some money so they are never poor. The rest goes to the foundation. He wants them to build their own careers, not live off what he already built. Less than 1% of $100 billion is still a large number. But it is not the fortune. It is the small slice he decided they should have. He built the company. He made the money. He decided how much of it his children get to keep. Was he protecting them from something that would ruin them, or was he simply choosing not to hand over what he earned?

Steve Wynn was the chairman and CEO of Mirage Resorts. He owned The Mirage, Treasure Island, the Bellagio and the Golden Nugget. His fortune was already in the hundreds of millions. In 1993 his daughter called from his car phone and said she had been kidnapped. In the video below, he tells what happened next. He was getting out of his car when the phone rang. She said, “Daddy, I’ve been kidnapped.” A man took the phone and told him if he did exactly what they said they would not kill her. If he did not, he would never see her alive again. They ordered him back to the casino. Go to the cashier’s cage. Do not tell anyone. He was being watched. When the call came at the cage they demanded a million and a half. He told them he did not know if the vault had that much. The man said do not let anyone know what you are doing. Wynn answered that if he emptied the drawers in front of the cashiers there would be bedlam. He was chairman and CEO, but he still could not walk up on a Monday night and empty the cage without security running. The vault had $1.4 million in $100 bills. He put it in a shopping bag. It was so heavy the bag would break, so he carried it like a baby. The money went into a car with the doors unlocked and the windows down. In 1973 the richest man in the world, J. Paul Getty, refused to pay the ransom for his kidnapped grandson. He said he had 14 other grandchildren, and if he paid for one they would take the rest. The kidnappers cut off the boy’s ear before the family paid. Wynn had only two daughters. He took the money from his own casino vault the same night. Hours later they told him where to find her. Airport parking. She was tied up in the back seat of her own car. He paid the ransom from his own casino without calling the police first. She was alive. Getty treated it like a business decision. Wynn emptied the cage. Was it just that he had fewer children, or did he simply care more?

Whole Foods founder John Mackey fired his 72-year-old father from the board after 15 years of helping him build the company. In the video below, Mackey explains why he removed his own father and how badly the decision hurt him. John was 40. He wanted to keep expanding, but his father had become increasingly cautious about risking the wealth they had built. Their arguments were damaging their relationship. Mackey urged him to sell half his shares for financial security and let him grow the business with the rest. There was something John didn’t know. His father would be diagnosed with Alzheimer’s a couple of years later. Looking back, Mackey believes it was already affecting him. He describes removing his father as the hardest thing he ever did. For years, he had argued with him, then given in out of love and respect. According to Mackey, the shares doubled in value within a year. His father later told him he had made the right decision and that he was proud of him. They reconciled. Would you remove the parent who helped build your company if you believed they were holding it back?

The British monarchy’s assets were estimated at $28 billion. Prince Harry said his family stopped funding him after he and Meghan left royal duties. In the video below, he complains that the family cut him off financially, even though he had already received roughly £10 million from his mother’s inheritance. Harry was 36 when he gave the interview in 2021. He had stepped back as a working royal the year before, but leaving the role also meant losing the security arrangements that came with it. He said he was told on short notice, while staying in Canada with Meghan and their son, that their royal protection would be withdrawn. They would have to find a way to pay for security themselves. Diana left an estate of £21 million. After more than £8 million in tax, £12.9 million remained. It was split between William and Harry. Advisers invested it, and by the time the brothers could access it, the total had grown to around £20 million, roughly £10 million each. He received that money for being her son. Nothing else. According to Harry, the Netflix and Spotify deals were never part of the original plan. They became a way to fund their new life and keep his family safe. He still had the inheritance Diana left him. He said he believed she would have been angry about how things turned out, but would ultimately have wanted him to be happy. He wanted independence from the royal family. His complaint was that the financial support stopped as he was trying to make that move. Was his family abandoning a son for going against their rules, or was a wealthy man in his thirties finally being asked to pay his own bills?

Tony Robbins built an estimated $600 million fortune. At 17, his mother chased him out of the house with a knife. In the video below, he describes growing up with an abusive mother and explains why he still gives her credit for the person he became. His mother struggled with alcohol and prescription drugs. Robbins says she beat him and once poured liquid dishwashing detergent down his throat until he vomited. While still a child himself, he bought groceries, cooked meals and looked after his younger brother and sister, trying to protect them from their mother. He left home as a teenager and worked as a janitor. Years later, he built a business teaching people how to change their lives, advising executives, athletes and some of the wealthiest people in the world. He remembers his mother’s violence, but also sees a connection between that childhood and his ability to endure difficult situations. Looking back, he says that if she had been the mother he wanted, he would not have become the man he is proud to be. That is how he makes sense of what happened to him. The money came later. At 17, he was a teenager whose own home had become a place he needed to escape. Would you forgive a parent who treated you this way just because your life turned out well?

Home Alone star Macaulay Culkin was reportedly worth $17 million by 15, but wasn’t even allowed to have his own bed. In the video below, he explains how and why he removed his parents from control of his money. He says he had made 14 movies in six years. He wanted a break, but felt nobody was listening while other people were making money from his work. His parents separated and fought over custody. As their legal bills mounted, his mother could no longer afford the rent. The family faced eviction while his earnings sat in the bank. Culkin says most of that money was locked away until he turned 18. He replaced his parents with an accountant to oversee the portion they controlled. The story became that he had “divorced” his parents. He has repeatedly explained that he removed their names from his finances, while remaining close to his mother. He stopped speaking to his father. Asked whether that was sad, he described a controlling parent he had no desire to see again. If your child earns millions, when does protecting their money become using them?

Spider-Man star Tobey Maguire swore on his mother’s life just to win a hand of poker. Once his opponent folded, he showed him he’d been bluffing. In the video below, Molly Bloom, whose life inspired Aaron Sorkin’s film Molly’s Game, recalls how he talked another player into folding. The other player had a decision to make. Maguire gave him something extra to think about by putting his mother’s life behind a claim about his cards. The bluff worked. His opponent folded, and Maguire could have collected the pot without revealing what he held. Instead, he showed him. The other player now knew he had been talked out of a hand by someone willing to swear on his mother’s life to sell the lie. Bloom describes his approach to poker: “It’s not really about money, it’s more about crushing souls.” That reveal is what makes Bloom’s description stick. Winning the money was already settled. Showing the bluff made sure his opponent knew exactly how he had lost it. Does poker reveal who someone really is, or do people play a character at the table that says nothing about who they are outside the game?

Before Chris Gardner became a millionaire, his ex handed him their toddler and said: “I don’t want the baby anymore. Here. It’s your turn.” The next day, they were homeless. In the video below, the man Will Smith played in The Pursuit of Happyness recalls hiding in public bathrooms with his son and teaching him to stay quiet so nobody would find them. The boy was about 20 months old. Gardner’s boarding house didn’t allow children, so taking his son meant losing his room. For nearly a year, they slept in shelters, cheap hotels and wherever else they could. Sometimes that meant a locked bathroom at a train station, where Gardner washed his son in the sink. He was training at a brokerage firm, earning roughly $1,000 a month. Most went toward childcare so he could keep working. His colleagues didn’t know he had nowhere to take his son at night. He eventually became a stockbroker, opened his own firm and made millions. Hollywood turned their life into a film. But when his ex brought the boy to his door, none of that was waiting for him. He had a job that barely paid enough to cover childcare and a room he couldn’t keep. Could you ever forgive a mother who walked away like that, or should they thank her for making them stronger?