Objectively, he was set for life. The Microsoft founder had inordinate power in the tech world “attract[ing] admiration and fear in equal measure,” according to a 1995 article from the New York Times. Some thought of the young billionaire as “Thomas Edison of the information age; others see John D. Rockefeller,” noted the author. Gates himself claims to have not thought of himself as much at the time.

“I wouldn’t say that I felt comfortable that we were successful until about 1998 or so,” Gates told CNBC Make It of his company. Microsoft went public years prior, in 1986, raising $61 million from 2.5 million shares sold in the first day—a deal that would catapult Gates into billionaire status the following year. He held the title of the richest person in the world for most of the years from 1995 to 2017, according to Forbes. 

“Not until the late-90s did I feel like, ‘Wow, we can even make a few mistakes and still be okay,’” Gates explained to CNBC of his feelings of instability. “I thought I was one mistake away from death until then. That was just my mentality.” 

Despite his success, Gates was unable to enjoy it for some time 

To get ahead and stay ahead in the early days, Gates felt he needed to deprive himself of sleep and a personal life.

“In my thirties and forties, when there would be a conversation about sleep it would be like ‘Oh, I only sleep six hours,’” Gates said in a 2023 podcast episode of Unconfuse Me with Bill Gates. “And the other guy says, ‘Oh, I only sleep five,’ then ‘Well, sometimes I don’t sleep at all,’” he added, explaining that at the time he felt he had to try harder because sleep is laziness and unnecessary. Gates now says he’s realized the value of rest and the health risks of sleep deprivation.

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Even so, Gates skipped truly celebrating some milestones because of his anxiety. “I was always running scared,” he said. “So whenever Microsoft would [celebrate] anniversaries, I’d be like, ‘I have no time to look backwards.’”

Interestingly enough, it was a tough time that led to him finally feeling like he had made it. In the late ’90s, Microsoft was sued by the government for antitrust violations, alleging that “Microsoft enjoys monopoly power” for its signature software. The company settled in the early 2000s. Microsoft did not immediately respond to requests for comment. 

Gates seemed to see the legal battle regarding a monopoly as a turning point. “That’s the first time I look back and say, ‘Okay, we are in a pretty good position here, and I understand why my competitors are so jealous that they think they need the Justice Department to help them out,’” Gates told CNBC.