A series of “yes or no” questions by Oprah Winfrey. That’s how Lance Armstrong admitted to doping; that’s how he admitted to winning his seven Tour de France titles assisted by PEDs. Did you ever take banned substances to enhance your cycling performance? “Yes.” In all seven of your Tour de France victories, did you ever take banned substances or blood dope? “Yes.” But here’s the kicker, the million-dollar question: Was it humanly possible to win the Tour de France without doping seven times?

Armstrong’s answer? “Not in my opinion. I didn’t invent the culture [of doping], but I didn’t try to stop the culture.” So, what happens when a cyclist known for both his accomplishments and scandals, once worth $125 million, loses everything? That’s the story of Lance Armstrong – of how, at the peak of his career, he won all those Tour de France titles, had endorsement deals, and built significant wealth. But when the doping scandal that had long been whispered about finally exploded, it all came crashing down.

His titles were stripped, his reputation shattered, and his lucrative sponsorships, including Nike, Oakley, and Trek, dropped him like a hot potato. The fallout was massive. Armstrong was once estimated to be worth $125 million, but his fortune fell to $50 million as his sponsors deserted him. Companies wanted their money back for previous years, and Armstrong was being sued by the U.S. government. They were doubly bereft, and for a while, it appeared he had lost even his life. But here’s where the story takes an unexpected turn: Back in 2009, Armstrong had the opportunity to invest at the time; it seemed like a risk, but it proved to turn into the very thing that ‘saved his family.’

Five years ago, Lance Armstrong shared a story on CNBC that revealed how this decision to invest gave him something he could reconstruct when other aspects of his life had become a wreck. Armstrong recalled meeting Chris Sacca, a former Google and Twitter executive, who now has a net worth of more than $1 billion, all because of a chance he took. “You know Sacca’s personality—larger than life,” Armstrong shared. “We were having fun and kept in touch. And then, some years later, probably around ‘08 or ‘09, he left to start his own venture capital fund called Lowercase Capital. And he called me.

“He said, ‘I’m looking for investors. Would you invest?’ I’m thinking to myself, ‘This guy has a huge personality, but he’s also very smart, very well-connected. Why not?’ So, I invested in Chris Sacca.” Here’s the twist: Armstrong’s $100,000 investment in 2009 went into a fund that was backing Uber, which at the time had a valuation of just $3.7 million. “I didn’t even know that he did Uber. I thought he was buying up a bunch of Twitter shares from employees or former employees. The biggest investment in Lowercase Fund I was Uber,” Armstrong admitted.

That investment turned out to be a game-changer for Lance Armstrong, especially after paying over $111 million in legal fees and settlements due to his doping scandal. As Uber’s valuation skyrocketed to $72 billion by 2019, Armstrong was able to recover some of his fortune. When asked how much that $100,000  is worth today, he didn’t give a straightforward answer: “It’s a lot more.” But he did give a hint when the interviewer suggested, “10, 20, 30, 40, or $50 million?”

The former cyclist replied, “It’s one of those.  It’s a lot, it’s a lot. It saved our family.” This came at a time when he was raising three children with his wife, Kristin Richard, whom he married in 1998 but divorced in 2003. Reflecting on the success of his investment, Armstrong described it as “too good to be true.” But at the same time, his life to this point hasn’t been easy!

Lance Armstrong turned his life around after cancer

Lance Armstrong’s journey is honestly wild. He kicked things off in the early 90s, winning the U.S. Amateur championship in 1991 and turning pro the next year. He was the first to win the title of the World Road Race Championship before he made the record in 1993 as the youngest to have achieved the feat. Then, in 1996, the tables were turned—he was diagnosed with testicular cancer that had metastasized to the head, lungs, and abdomen. But guess what? He didn’t give up easily; he struggled instead. Armstrong’s journey included a battle with cancer, and after recovery, he returned to compete in the Tour de France.

Though Armstrong has now retired from cycling, he does not seem to have gone into oblivion. In 2008, he decided that he needed to open a bike shop, and, as everyone knows, if you are going to have a bike shop, it’s got to be called Mellow Johnny’s, and then since there is a cafe next door, why not combine the two along with a beer garden? After overcoming cancer, he continued to develop his business ventures. In 1997, he formed the Lance Armstrong Foundation, now known as Livestrong, to support cancer-fighting and survivors. It isn’t all about race in his life—it is one that has been marked by comebacks, reinvention, and charitable efforts.