Steve Jobs’s daughter grew up on $385 a month while he said she wasn’t his. On his deathbed he kept telling her: I owe you one. Lisa was born in 1978 on a farm commune in Oregon. Her mother was Chrisann Brennan, Steve’s girlfriend. Steve said the baby wasn’t his. A DNA test put the probability that he was the father at 94.1%. A court ordered him to pay $385 a month and pay back the welfare her mother had been living on. Days later Apple went public. He was suddenly worth more than $200 million. In 1983 he still told Time magazine that 28% of the male population of the United States could be the father. That same year Apple released a computer called the Lisa. When she asked him if it was named after her, he said: nope, sorry, kid. Years later he told Bono it was. At 14 she moved in with him. He had one condition: she could not see her mother for six months. She asked once if she could have his Porsche when he was done with it. You’re not getting anything, he told her. Nothing. And yet, she says, there was love. She remembers a freezing night when he sat through her boyfriend’s school play without a sweater, because he knew how much it meant to her. At the very end, dying of cancer, he kept apologizing for the time they had missed. I owe you one, he kept saying. I’m so sorry. Did she forgive him? Not at the time. Now, in many ways, yes. We did like each other, she said. I wish there had been more time. He built one of the most valuable companies in the world. The one thing he couldn’t buy back was the years he spent saying she wasn’t his. Can success ever make up for the people you failed on the way? Follow me for more stories like this.

Elon Musk went from $180 million to broke in 2008. Then NASA called with a $1.5 billion contract. After PayPal, Elon’s share was $180 million. He bet all of it on two companies everyone said would fail: Tesla and SpaceX. By 2008 he was 37, and everything was going wrong at once. SpaceX had launched three rockets. All three failed to reach orbit. Tesla’s first car, the original Roadster, had quality problems. The factory was full of cars that couldn’t be delivered. Every month cost tens of millions. The economy collapsed into the worst recession since the Great Depression. And, as he put it, he was getting divorced, by the way, to add to that. That was definitely the worst year of my life. His fortune was gone. When Tesla called investors for money, some cursed at them and hung up. Asked if he was broke, he said: more than broke. On the Sunday before Christmas he woke up and thought he was closer to a nervous breakdown than he had ever been. SpaceX had money for one more launch. A fourth failure would have been game over. Flight four worked. The week of Christmas, NASA called with a $1.5 billion contract. Elon blurted out: I love you guys. Two days later, on Christmas Eve, Tesla’s investors agreed to put in more money. Both companies were saved within three days. In the middle of all this he met Talulah Riley. They were engaged after about two weeks. She was 22 and walked into a house with his five young sons. This week Tesla unveiled a new Roadster. The car that almost ended him in 2008 now flips in midair. Would you have bet everything twice? Follow me for more stories like this.

Peter Thiel wanted flying cars and got 140 characters. Elon Musk paid $44 billion for the characters. Then he built the car. We wanted flying cars, instead we got 140 characters. It was the tagline of Thiel’s venture fund, Founders Fund, and it became one of the most quoted lines in Silicon Valley. A jab at the whole industry. Huge breakthroughs were promised. What arrived was Twitter. Thiel and Musk go back a long way. They built PayPal together. In 2000 the board removed Musk as CEO while he was on his honeymoon, and Thiel took over. Musk didn’t fight. He later said the better course was to turn the other cheek. Thiel’s fund went on to invest in SpaceX. In 2018 Thiel sat down for a long interview and said his number one rule was never to compete with Elon. Then the host brought up flying cars. Elon is against them. Thiel agreed. Elon’s objection was that they were too noisy. In 2022 Musk bought Twitter for $44 billion. The 140 characters were now his. This week, at the unveiling of the new Tesla Roadster, he brought up Thiel’s line. Then a Roadster drove up a ramp, left it upside down, flipped in midair on blasts of compressed air and landed on its wheels. Flying cars are real, Musk said. Thiel’s complaint got answered by the one man he said never to bet against. Do you think we’ll see flying cars on real roads in our lifetime? Follow me for more stories like this.

Elon Musk lost PayPal on his honeymoon. 2 years later, eBay paid $1.5 billion for it and he was still one of the biggest shareholders. In January 2000 Elon married Justine. There was no time for a honeymoon. PayPal was growing fast, burning money fast, and needed to raise more. So in September he combined the two. A fundraising trip that would end with a honeymoon in Australia. Two weeks away. While he was gone, his own team went to the board. They had decided he was not the right person to run the company. Peter Thiel would take over. Elon flew back. The vote was already done. He later admitted to his biographer he was pretty angry at first. Justine said it was shocking, but she thought he handled it pretty well. In this interview from 2008 he explains the choice he made. He could have fought hard. Instead, at a critical moment for the company, he conceded. I didn’t agree with their conclusion, he said. But the better course of action is to turn the other cheek and make the relationship good. A few months later he caught malaria and ended up in intensive care. He recovered. He stayed on the board. He kept his shares. In 2002 eBay bought PayPal for $1.5 billion. Elon put most of his money into two companies everyone said would fail: SpaceX and Tesla. Years later Peter Thiel’s fund invested in SpaceX. The man who took his job became one of his investors. Could you forgive the people who took your company while you were on your honeymoon? Follow me for more stories like this.

Jeff Bezos’s grandfather taught him to rebuild a bulldozer and build a crane. The lesson Jeff kept took 1 sentence on the side of the road. Every summer from the age of 3 or 4 until he was 16, Jeff lived with his grandparents on their ranch in South Texas. His grandfather did everything himself. He did his own veterinary work. He made his own needles from a piece of wire, heated with a blowtorch, pounded flat, sharpened, a hole drilled through. Some of the cattle even survived, Jeff jokes. One summer he bought a broken-down D6 Caterpillar bulldozer for about $5,000. They spent the whole summer fixing it. To get the transmission out, they built their own crane. He believed he could solve any problem. Jeff watched and learned. But the lesson that stayed came from somewhere else. It was 1974. Jeff was 10 and very sure he was a smart kid. On the car radio, anti-smoking ads were everywhere. One said every puff on a cigarette takes two minutes off your life. His grandmother was a chain smoker. She smoked the whole drive with the window down. So Jeff did the math. He estimated her puffs, multiplied by two minutes, stood up in the back seat and proudly announced the result. Something like 7 years. He expected to be praised for being clever. She burst into tears. His grandfather pulled the car over. In their entire relationship he never said one harsh word to Jeff. He took him out of the car and walked him to the back, while his grandmother sat crying in the front seat. Jeff had no idea what was coming. Jeff, one day you’ll understand that it’s harder to be kind than it is to be clever. More than 50 years later, he still tells the story on stage. When was the last time you chose clever over kind? Follow me for more stories like this.