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Kevin O'Leary's mother invested 20% of her pay every week and held that portfolio for 55 years.
When she died, a lawyer had to tell her son she was rich.
She worked in her father's business, in billing, and got paid in cash.
Every week, 20% went into two things: big dividend stocks and seven-year telco bonds paying about 6.5 to 8%.
She never touched the principal. The dividends and interest paid for college for her two sons and helped her sisters through hard times.
Her rules: no more than 5% in any one stock or bond. No more than 20% in any one sector. Ever.
In the video below, O'Leary says it plainly: "This is not genius. This is just diversification."
When the lawyer called him in as executor, he told him his mother was middle class. "No, you've got to come down here."
She had kept the account secret from both of her husbands. She wanted money no man could control.
Over 55 years, he says, her results beat "any hedge fund guy."
Her son built a career on big deals. Now he invests almost exactly like his mother.
Boring rules you actually follow beat brilliant bets you don't survive. My worst loss came from ignoring the 5% rule.
What percent of your money is in your single biggest position?
Steve Wozniak gave away about $10 million of his own Apple stock.
Steve Jobs offered one of Apple's first engineers zero.
Before Apple went public in 1980, five people ran the company and held almost all the stock.
In the video below, Woz explains: "When we went public, I didn't feel right about it. I felt that everybody who'd been around us was a part of helping."
He came from Hewlett-Packard. There, part of the profit went to employees as stock every quarter.
"You, as an employee, should feel like an owner of your company."
So he gave his own shares to almost everyone in marketing and engineering above a certain level.
He gave huge amounts to a few kids who were still in high school when they helped him write code.
"They shouldn't be treated like they aren't worth anything."
One of the people Jobs refused was Daniel Kottke, employee number 12 and Jobs's old college friend. Woz gave Kottke shares out of his own pocket.
Jobs built the richer fortune. Woz built the better reputation.
If your company took off, how much would you give the people who helped you early?
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Spotify paid Alex Cooper $60 MILLION for Call Her Daddy. Her co-host Sofia Franklyn got $0 of it.
Today her memoir tells her side.
By Barstool boss Dave Portnoy's account, he started both women at $70,000 a year to talk about sex on a podcast. The show exploded, and Sofia recalls how small the hosts' cut of the store was:
"I know we were getting paid 2.5% each off merchandise"
One hoodie with a line she claims as hers sold over a million dollars. Then she did the math on Barstool:
"They were making over 11 million a year."
In 2020 both hosts wanted out. Barstool offered them ownership, a shorter contract and more money. Alex took the deal. Sofia refused and said Alex went behind her back.
Portnoy blames Sofia's boyfriend, an HBO Sports executive who wanted to manage the pair. He says Alex came to him with a warning:
"Sofia is never going to take it. She's moving the goalposts on you."
Alex kept the show. A year later Spotify signed her for more than $60 million, and Portnoy called Sofia's refusal one of the worst decisions ever made by a human.
In the memoir, Sofia writes that a lawyer they shared let slip that Alex was earning more. What she felt was pure hatred.
Did Sofia lose Call Her Daddy to her boyfriend, or to her best friend?
Howard Schultz had 60 to 90 days to raise $3.8 million and buy Starbucks.
Weeks in, one of his own investors went behind his back with an all-cash offer.
It was 1987. Starbucks had six stores and was in trouble. The founder offered to sell it to Schultz.
"The good news is the opportunity. The bad news, no money."
About 30 days in, he had raised a third. He told the founder he was confident.
In the video below, he admits: "But I wasn't confident. I didn't know where the money was coming from."
Then the call. An all-cash offer. "From who?" "One of your investors."
A friend from his basketball league worked at a Seattle law firm. He got Schultz a meeting with his boss, Bill Gates Sr.
Gates asked two questions. "Is everything you told me true?" "Have you left anything out?" Then: "We're going to take a walk."
They walked across the street into the rival's office. Gates stood over his desk and told him to stand down.
Outside, he told Schultz: "You're going to own Starbucks Coffee Company, and my son and I are going to help you."
Gates Sr. never told anyone. Years later, Schultz told the story at a Microsoft summit. Bill Gates hadn't known his own father did it.
Your network is part of your net worth. Most of my best chances came from people, not applications.
Who would you call if your biggest deal was falling apart?
Airbnb's cofounder says Paul Graham hated their business idea.
Y Combinator took them anyway because of cereal they sold for $40 a box.
In 2008, AirBed & Breakfast was running out of money. Investors showed little interest and the founders were carrying credit card debt.
In the video below, one founder remembers how the idea started: "Maybe we should do more with the breakfast."
So they made Obama O's and Cap'n McCain's for the election. Cartoon candidates on the box, supermarket cereal inside.
They mailed dozens to journalists, and suddenly they were a story again. They sold $30,000 worth.
The money bought time, but not investors. The founders talked about calling it quits and applied to Y Combinator as one last shot.
Graham was not sold. Before they left, Joe Gebbia pulled out a box of Obama O's. Graham remembered the stunt and changed his mind.
Cofounder Nathan Blecharczyk recalled him saying: "The cereal showed me how resourceful you guys are."
12 years later, Airbnb closed its first day as a public company worth about $86.5 billion.
Did Paul Graham back the founders, or just a clever stunt?
Netflix offered to sell itself to Blockbuster for $50 million in 2000.
10 years later, Blockbuster filed for bankruptcy.
Netflix was two and a half years old. Under 100 employees. On track for $3 million in revenue and $50 million in total losses.
Blockbuster was on track for $6 billion. 60,000 employees. 9,000 stores.
At first, Blockbuster wouldn't even take their calls. Then finally: "We will see you now."
In the video below, co-founder Marc Randolph describes the room. Expensive suits on one side. "Silicon Valley T-shirts and jeans" on the other.
They pitched it: Netflix runs online, Blockbuster runs the stores. The suits nodded.
Then came the question. "How much should we pay for you?" Reed Hastings answered: "50 million dollars."
Randolph says the reaction was laughter. The meeting went downhill fast.
On the quiet flight home, he had one thought: "Now we're going to have to kick their ass."
Blockbuster had $6 billion and 9,000 stores. What it didn't have was a reason to change.
Today Netflix is worth hundreds of billions.
The biggest risk isn't the competitor you fear. It's the one you laugh at. I've laughed at a stock or two I later wished I'd bought.
Which big company today is making Blockbuster's mistake?
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George Lucas signed with 20th Century Fox over $150,000 to make Star Wars.
Fox gave him the merchandising rights instead of a raise. 35 years after Star Wars opened, he sold Lucasfilm for $4.05 billion.
In the video below, Lucas explains why he skipped the money: "I want to change everything to be in my favor."
He says he could have asked for $1 million. Instead he asked for the sequel rights and the licensing.
Lucas says the studio told him: "If the film's not going to be successful, we don't care about the sequel rights."
Alan Ladd Jr., the Fox executive behind the deal, later told The Hollywood Reporter: "At the time, merchandising meant nothing at all."
Star Wars opened in 1977. Fox kept the film. Lucas kept the sequels and the merchandise.
In 2012, Disney bought Lucasfilm from him. About half of the price was cash, the rest Disney stock.
Did Fox protect its money, or did Lucas outsmart it?
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Ashton Kutcher reportedly turned a $30 million fund into $250 million.
He doesn't plan to hand it down to his kids.
He started out investing his own money in startups.
In the video below, he admits the first problem: "I was running out of money really quickly, because these things take a while to actually turn over and pay out."
So he teamed up with Guy Oseary and Ron Burkle and started a fund, A-Grade. Early bets included Uber and Airbnb.
Here's how he decides who gets the money.
"Do you have an assumption about the world, or an insight about the world, that other people don't necessarily share?"
Because if it works, everyone will copy it. "A lot of other people are going to try to do it as well."
Most actors put their money into houses and cars. He put his into companies that hadn't proven anything yet.
And the money isn't for his family. "Handing money down generationally inside your family doesn't necessarily behoove your kids."
He says his philanthropy drives his business choices, starting with Thorn, his foundation that builds tech to protect kids.
My takeaway: startup money is a long wait with no paycheck. Only put in what you can forget about for ten years. I keep my risky bets small for exactly that reason.
Would you leave your kids a fortune or make them earn it?
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Never Gonna Give You Up was played 154 million times on YouTube in one year. The man who wrote it got $16
In the video below, Rick Astley on what it's like when the biggest song of your life becomes the internet's favorite prank
In 1987 the song went to number one in 25 countries. Astley was 21
Twenty years later, the internet turned it into a joke. You click a link, you get Rick. They called it rickrolling
By 2008 the video had more than 154 million plays
Co-writer Pete Waterman opened his royalty statement for that year. £11, about $16
"I rang my publisher and they said 'You'll be all right', until I saw the royalty statement"
Astley did even worse. By 2010 he said he'd made about $12 from it
Here's why. Astley didn't write the song, so he only gets a performer's share. The label owns the recording. And YouTube's early deals with music companies paid almost nothing per view
The video passed 1 billion views in 2021. Millions of people still get rickrolled every year
Astley says he finds it bizarre and funny, and that his main worry was his daughter being embarrassed
The joke made the song immortal. The money went almost everywhere except the people who made it
Did rickrolling give Rick Astley a second career, or did the internet steal his song for free?
Magic Johnson made about $40 million in 13 NBA seasons.
In 2023, Forbes named him a billionaire. Not from basketball.
Coming out of college in 1979, every shoe company wanted him.
He says a young Nike couldn't offer much cash. So Phil Knight offered him stock instead.
In the video below, he tells Ellen why he passed: "I didn't know nothing about stocks. I'm from the inner city."
He took the money from Converse.
"It still haunts me today. Every time I'm in a Nike store, I get mad."
Most people would have stopped at the regret. Magic went the other way.
After basketball, he went after ownership. Movie theaters. Around 100 Starbucks locations. An insurance company.
Then pieces of the teams themselves. The Dodgers. The Sparks. The Commanders.
The guy who didn't understand stock ended up owning parts of the teams that pay the players.
My takeaway: one missed deal is a lesson, not a life sentence. What you do after the mistake matters more. I sold my first stock way too early and still remember the price.
What's the deal you still kick yourself for passing on?
Steve Harvey had $35 and was sleeping in his car in hotel parking lots.
Within days, he had almost $1,000 and his first TV appearance.
He was ready to quit. He went to a pay phone to call his dad.
First he checked his answering machine. Showtime at the Apollo wanted him on TV that Sunday.
In the video below, he explains why that felt like bad news: "I've got $35. How am I gonna get to New York?"
Then a second message. A gig in Jacksonville, Friday night, $150. He drove three and a half hours.
He killed. The guy who hired him offered another $150 for Saturday. Now he had $300.
He found a $99 round trip to New York, parked his car at the airport and flew with everything he owned in two bags.
At the Apollo that night, he got a standing ovation. They paid him $750.
"I'd never made $750 telling jokes in one night."
Weeks later they asked him to host the show. He says he did it for eight years.
The $750 night only happened because he didn't skip the $150 one.
My takeaway: small money isn't small when it's the bridge to bigger money. I've turned down $100 jobs I should have taken.
Would you have driven 3.5 hours for $150 with $35 to your name?
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Charlie Munger was a lawyer with 8 kids to feed and no family money. He became a billionaire anyway.
In the video below, he explains exactly how. He spent less than he earned, every single year, and invested the rest. After 13 years, his investments were worth more than everything he had made as a lawyer, before taxes.
He did it in his spare time, with what he called "little tiny sums."
And his very first investment almost wiped him out. "It was hell on earth."
He kept going anyway, became Warren Buffett's partner, and died at 99 worth about $2.6 billion.
What's harder for you, earning more or spending less?
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Elon Musk lost a $56 billion pay package to a man who owned 9 Tesla shares. A judge voided the deal, then ordered Tesla to pay that man's lawyers $345 million, after they asked for $5.6 billion.
Then Delaware's Supreme Court gave it all back. By then the package was worth $139 billion. The man with 9 shares got $1.
In the video below, Musk walks on stage right after shareholders voted for his pay a second time: "Hot damn, I love you guys."
In 2018 Tesla's board offered Musk options on 304 million shares, about 9% of the company, if Tesla hit a set of huge targets. It hit every one.
Richard Tornetta, a former heavy metal drummer with 9 shares, sued that same year.
In January 2024 a Delaware judge struck the deal down and called it "unfathomable."
His lawyers asked for $5.6 billion in fees. The judge called that a windfall and gave them $345 million.
In June 2024 shareholders voted for the package again. In December the judge rejected it again.
Musk moved Tesla's legal home from Delaware to Texas.
On December 19, 2025, the Delaware Supreme Court reversed it, unanimously. Throwing the deal out, it said, left Musk "uncompensated for his time and efforts over a period of six years." The lawyers' fee was cut by about 80%. Damages: $1.
Musk said he was "vindicated."
9 shares froze the biggest paycheck in history for 7 years. The final bill for the man who started it: $1.
Did the system protect shareholders, or did 9 shares nearly cost Musk $139 billion?
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Aaron Hernandez had security cameras all over his own house. On the night of 17 June 2013, the night Odin Lloyd died, his own cameras recorded him walking through the house holding what prosecutors said was a gun. A few minutes later the same cameras recorded him picking up his baby daughter. Two hours after that, Lloyd was shot dead in an industrial park down the road.
Nobody put those cameras there but him.
In the video below it is all on his own footage, one beat after another: the cigarette in the driveway, the two men arriving at midnight, the shape in his hand, and then his daughter. Watch how little time passes between the last two.
Prosecutors froze the stills and brought in Kyle Aspinwall, a former police chief who now works for Glock. He told the court the back strap, the magazine well and the trigger guard all matched. In his opinion it was a Glock pistol. The ballistics in the case pointed to a Glock 21.
The defence said it could have been a TV remote.
The weapon was never found.
His nanny was asked to sign a confidentiality agreement. She agreed to it and never actually signed it, so when the trial came she was free to talk. She told the court about a night he offered her a lift to her car and got on the highway instead. Odin Lloyd was in the back seat.
In April 2015 a jury convicted him of first-degree murder. Life without parole.
On 19 April 2017, days after being acquitted in a separate double-murder case, he was found dead in his cell. He was 27.
That November, Boston University announced what they had found in his brain. The most severe case of CTE they had ever seen in anyone his age.
Prosecutors said his own cameras were the case. The defence said you cannot convict a man on a blurry shape in his own hallway. Which side would you have been on?
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Cory Chase's real name is Audrey Wirtzberger. She was born in New Jersey in 1981 to a couple named Olga and Larry. At 19 she joined the United States Army. After the Army she worked in food service. By her mid-twenties she was filming amateur porn for a company called Southern Charms. By 2007 she was shooting for Reality Kings in Florida. Two years later she and her husband Robert Leon quit their day jobs and went into porn full-time. They have been married since 2005. He still works alongside her.
She became the face of the most searched porn genre in America. The genre is called fauxcest. Stepmom scenes. In 2018 "stepmom" was the fourth most popular search term on Pornhub. In 2019, 2021, and 2022 it was seventh. She didn't create the category. She is just the woman the algorithm chose to represent it.
In September 2017, United States Senator Ted Cruz's official Twitter account liked a two-minute clip of hers. The video was called Dicks for Two. She played a stepmother who walks in on her stepdaughter having sex and decides to join in. Cruz blamed a staffer. The clip became the fastest porn video to reach one million views. His Republican Party had called porn "a public health crisis" in its platform months earlier. As Texas solicitor general, Cruz had once defended a state law banning the sale of sex toys.
She found out about the whole thing while sitting in the dark during Hurricane Irma with no power and almost no internet access. She tweeted: "So I hear I am trending with Ted Cruz. I am literally in the dark."
When reporters asked her about it she said she did not like that he watched it for free. He pirated that video. He should have paid Reality Kings for a subscription.
She is 45 years old. She has been in the industry for almost two decades. She won Best MILF Performer at the AVN Awards. She is still active. She is still married to the same man she married before any of this started. They built the business together.
Most people who have heard the name Cory Chase will never know her real name is Audrey Wirtzberger, that she served in the U.S. Army, or that a sitting United States senator publicly liked her work and then called it a staffing issue.
Did Ted Cruz's staffer accidentally like a porn video, or did a senator who built his career on family values get caught watching the most popular genre in America and blame the nearest intern?
Jack Whittaker won $315 million in the Powerball on Christmas 2002.
A few years later, he said he wished he had torn up the ticket.
He gave his 17-year-old granddaughter Brandi about $2,000 a week. And four cars.
In the video below, the interviewer pushes back. Whittaker doesn't: "To a young kid, cars mean a lot. And I'm very proud that she had four cars."
The money brought new friends. Then drugs.
He checked her into three treatment programs. None of them worked.
In December 2004, Brandi was found dead. She was 17.
"My granddaughter's dead, probably because of the money."
Then he says the line I can't stop thinking about. Before the lottery, he had his arms around her. After it, "there wasn't enough of me to get my arms around everything."
He had more money than he could ever spend. What he ran out of was himself.
By then his marriage was ending too. "My wife said she wished she'd torn the ticket up. Well, I wish we had torn the ticket up too."
My takeaway: giving money is easy. Giving it with limits is the hard part, especially to the people you love most. I think about this every time I want to fix someone's problem with cash.
How much would you give a 17-year-old if you suddenly had millions?
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Sasha Grey left porn, starred in a Steven Soderbergh film, landed a role on HBO’s Entourage, and was trying to start a new life. Then she spent one morning reading a children’s book to first graders in Compton. Parents went to war, and the school district publicly denied she had ever been there. There were photos.
She grew up Catholic in Sacramento and graduated high school a year early. She says she carried a lot of guilt about her own fantasies and wanted to show other people they didn’t have to feel that shame. Right after she turned 18 she sent her photos and a written mission statement to adult agencies. Nobody answered. She was already driving home when one agent finally called back. A week later she moved to LA, rented a pool house in North Hollywood because she had no credit history, and shot her first scene.
She became one of the biggest names in the industry. In 2009 Soderbergh cast her as the lead in The Girlfriend Experience. At the end of that year, at 21, she quietly stopped shooting. No announcement. She was writing, making music, acting, and refusing to pick a side when both worlds demanded she did. She didn’t make it official for two more years.
In November 2011 she volunteered for Read Across America and spent a morning at Emerson Elementary in Compton. She read Dog Breath, a silly children’s book about a dog with bad breath, to first and third graders and tweeted about how sweet the kids were.
Then TMZ got the photos. Parents flooded the school with complaints. One asked why the school couldn’t find a firefighter or a police officer instead. Another said people like her shouldn’t be around children at all. The district told reporters she had never been in the building, even though the pictures were all over the internet.
She didn’t hide. She said she had a past some people disagreed with, but it didn’t define who she was. She has never said she regrets it.
Today she’s a streamer, a DJ and a published novelist. A song she wrote about her late father ended up in Mission: Impossible – Fallout. She left porn 16 years ago. Some people will never let her.
Should a former porn star be allowed to volunteer with children, or were the parents right to be furious?
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Al Capone reportedly earned about $105 million a year, roughly $2 billion today. in 1928 he paid $40,000 ($700,000 today) for a Miami Beach mansion. in 1931 he went to prison for something other than racketeering or murder.
it was unpaid taxes. in 1929 seven of his rivals were killed in the St. Valentine's Day Massacre, and the case that put him away had nothing to do with it.
the mansion stood on Palm Island and covered about 6,000 square feet. it sold in 2021 for $15.5 million and was torn down in 2023.
prosecutors later listed how he spent. $8,000 on diamond belt buckles. $116,000 lost on horse races. $6,500 on meat for guests at a poker party.
a Treasury team led by agent Frank Wilson spent more than two years going through about 2 million documents. they found three ledgers recording cash, marked only with first initials, and traced cash through cashier's checks.
prosecutors said he owed $215,080 in taxes on about $1 million of income from 1924 to 1929. reports say the jury was replaced at the last minute after bribery claims.
on October 17, 1931 the jury found him guilty on 5 of 23 counts. he got 11 years, a $50,000 fine and about $7,700 in court costs.
in 1934 he was moved to Alcatraz. in 1936 another inmate stabbed him. in 1938 he was diagnosed with syphilis. he was released in November 1939 because of failing health and died on January 25, 1947 at 48, at his Palm Island home.
$215,080 in unpaid taxes put him away: justice or a loophole?
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In 2007, Kanye West's mother died the day after three plastic surgeries by Dr. Jan Adams. Eight years later, the surgeon said Kanye's family was to blame.
In the video below, Adams tells his side and asks Kanye to clear his name. "Kanye West can end this by telling the truth."
Donda West was 58 when Adams did all three surgeries in one day. She went home to recover, and her nephew, a nurse, was to look after her.
She died the next day, and the coroner linked her death to heart disease and the surgery. Critics accused Adams of doing too many procedures at once.
In 2015, Kanye blamed himself. "If I had never moved to LA, she'd be alive," he told Q magazine.
That September, Adams said the nephew had gone to a baby shower. Donda was left lying flat on her back, he says: "All you had to do is sit her up."
The nephew denied Adams's claims. No one was officially blamed, and California passed the "Donda West Law": a medical exam before any cosmetic surgery.
Do you think a medical exam before surgery could have saved Donda, or better care after it?
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At his sentencing in a Kansas courtroom in 2005, Dennis Rader stood up and spoke for twenty-seven minutes. He went through the ten people he had murdered one at a time, and for each of them he had found something they had in common with him. One had spent summers on her grandparents' farm. So had he. One had walked the halls of his old high school. One had worked where he worked.
In the video below he talks about some of them.
Kathryn Bright was 21. He said she had spent time on her grandparents' farm, and that he had too, and that he had many fond memories of it. He said she had gone to his old high school and had probably walked the same hallways. He said she had worked at the Coleman plant, like he had, just trying to keep her head above water.
Then he said: and I took that from her.
Dolores Davis was 62. He said she loved animals, and that he had worked in animal control, and that people in Park City would tell you he was always good with animals. He said he had read that she spent her last Christmas with her family, and that he had done that too, and that it was a wonderful time.
Then he said: and I took that from her.
Nancy Fox was 25. He said she was a wonderful young lady, well organised, a hard worker. He also said he had tracked her just like a predator.
Marine Hedge was 53 and lived on his street. He said he used to walk past her place. That she was a gardener and he loves to garden. That she went to a church he had been to with the Boy Scouts.
Joseph Otero was 38, a retired Air Force master sergeant. He said he had been in the Air Force as well. That Otero was a husband and he was a husband. That Otero had been a pilot and he had always been fascinated by aerodynamics. He said their threads were close.
Julie Otero was 34. She had worked at Coleman too. He said she was a lot like his wife. A loving mother who raised kids.
Josephine Otero was 11. He said she would have been a lot like his own daughter at that age. That she played with Barbie dolls. That she liked to draw, and he likes to draw.
Joseph Otero II was 9. He said the boy had been just like him once. A boy and a dog. He said a boy and a dog is a thing you have to have when you are a kid.
Shirley Vian was 24. He said she was probably a very beloved mother.
Vicki Wegerle was 28. He said she played the piano, and that the piano was one thing he had always wanted to learn.
When the list was finished he said: I hope I haven't left somebody out.
Then he asked the court for some things. He said a lien had been put on his house and that his wife was the final victim. He corrected the prosecution on two details he felt they had got wrong, because he wanted the record to be accurate.
And he asked for his wallet back, so that he could take the family photographs out of it before they took him away.
He got 175 years.