• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
SuccessBill Gates

Bill Gates thought he was “one mistake away from death” with Microsoft until the late 90s

By
Chloe Berger
Chloe Berger
Down Arrow Button Icon
By
Chloe Berger
Chloe Berger
Down Arrow Button Icon
February 4, 2025, 11:48 AM ET
Microsoft founder Bill Gates.
Microsoft founder Bill Gates.John Nacion / Contributor—Getty Images

Standing atop Silicon Valley in the 1990s, Bill Gates still felt his perch to be precarious. 

Recommended Video

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.

Read more from Fortune

  • This entrepreneurial couple cashed out their 401(k)s and sold a $126 million company—now, they run a U.K. soccer team
  • Trump’s 25% tariffs are backfiring and threatening Gen Z’s trade career aspirations—putting car manufacturing jobs in peril
  • Gen Z women are being sold a risky dream: the realities behind ‘investing’ in designer bags like the Hermès Birkin
  • Like Tim Cook and Gen Z, AEG’s top exec eats the same lunch most days and wears the same outfit
  • Warren Buffett reveals the unique education strategy he took in school—and eventually paid off with a $170 billion fortune
  •  

    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.

    At the Fortune Workplace Innovation Summit, Fortune 500 leaders will convene to explore the defining questions shaping the workforce of the future—delivering bold ideas, powerful connections, and actionable insights for building resilient organizations for the decade ahead. Join Fortune May 19–20 in Atlanta. Register now.
    About the Author
    By Chloe Berger
    LinkedIn iconTwitter icon
    See full bioRight Arrow Button Icon

    Latest in Success

    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025

    Most Popular

    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Finance
    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
    By Fortune Editors
    October 20, 2025
    Fortune Secondary Logo
    Rankings
    • 100 Best Companies
    • Fortune 500
    • Global 500
    • Fortune 500 Europe
    • Most Powerful Women
    • World's Most Admired Companies
    • See All Rankings
    • Lists Calendar
    Sections
    • Finance
    • Fortune Crypto
    • Features
    • Leadership
    • Health
    • Commentary
    • Success
    • Retail
    • Mpw
    • Tech
    • Lifestyle
    • CEO Initiative
    • Asia
    • Politics
    • Conferences
    • Europe
    • Newsletters
    • Personal Finance
    • Environment
    • Magazine
    • Education
    Customer Support
    • Frequently Asked Questions
    • Customer Service Portal
    • Privacy Policy
    • Terms Of Use
    • Single Issues For Purchase
    • International Print
    Commercial Services
    • Advertising
    • Fortune Brand Studio
    • Fortune Analytics
    • Fortune Conferences
    • Business Development
    • Group Subscriptions
    About Us
    • About Us
    • Press Center
    • Work At Fortune
    • Terms And Conditions
    • Site Map
    • About Us
    • Press Center
    • Work At Fortune
    • Terms And Conditions
    • Site Map
    • Facebook icon
    • Twitter icon
    • LinkedIn icon
    • Instagram icon
    • Pinterest icon

    Latest in Success

    conway
    North AmericaObituary
    Gerry Conway, comics legend who created the Punisher, dies at 73
    By Claire Rush and The Associated PressMay 2, 2026
    6 hours ago
    shoplift
    EconomyGen Z
    Gen Z is rebelling against the economy with ‘disillusionomics,’ tackling near 6-figure debt by turning life into a giant list of income streams
    By Jacqueline MunisMay 2, 2026
    6 hours ago
    First Watch CEO Chris Tomasso holding his fist up at the New York Stock Exchange
    SuccessView from the C-Suite
    CEO writes hundreds of thank you notes to staff and still eats in the break room—which ‘always, for whatever reason, blows new employees away’
    By Preston ForeMay 2, 2026
    6 hours ago
    Suze Orman once said earning more than $800,000 would make her ‘sick to my stomach’—but that turning down Oprah Winfrey cured her self-doubt
    SuccessHow I made my first million
    Suze Orman once said earning more than $800,000 would make her ‘sick to my stomach’—but that turning down Oprah Winfrey cured her self-doubt
    By Orianna Rosa RoyleMay 2, 2026
    6 hours ago
    mackenzie
    Commentaryphilanthropy
    Stop donating to Harvard and the Ivy League. There’s a better option that MacKenzie Scott already figured out
    By Ed Smith-LewisMay 2, 2026
    12 hours ago
    Young trade worker learning on job
    SuccessHiring
    Forget Big Tech: Small businesses will hire nearly 1 million grads in 2026—and some of the hottest roles are gloriously AI-proof
    By Emma BurleighMay 1, 2026
    1 day ago

    Most Popular

    Scott Bessent on financial literacy: 'it drives me crazy' to see young men in blue-collar construction jobs playing the lottery
    Personal Finance
    Scott Bessent on financial literacy: 'it drives me crazy' to see young men in blue-collar construction jobs playing the lottery
    By Fatima Hussein and The Associated PressMay 1, 2026
    1 day ago
    A Chick-fil-A worker got fired and then showed up behind the register to allegedly refund himself over $80,000 in mac and cheese
    Law
    A Chick-fil-A worker got fired and then showed up behind the register to allegedly refund himself over $80,000 in mac and cheese
    By Catherina GioinoMay 1, 2026
    1 day ago
    Current price of oil as of May 1, 2026
    Personal Finance
    Current price of oil as of May 1, 2026
    By Joseph HostetlerMay 1, 2026
    1 day ago
    China dominates the world's lithium supply. The U.S. just found 328 years' worth in its own backyard
    North America
    China dominates the world's lithium supply. The U.S. just found 328 years' worth in its own backyard
    By Jake AngeloApril 30, 2026
    2 days ago
    Apple cofounder Ronald Wayne—whose stake would be worth up to $400 billion had he not sold it in 1976—says that at 91, he has no regrets
    Success
    Apple cofounder Ronald Wayne—whose stake would be worth up to $400 billion had he not sold it in 1976—says that at 91, he has no regrets
    By Preston ForeApril 27, 2026
    5 days ago
    Current price of gold as of May 1, 2026
    Personal Finance
    Current price of gold as of May 1, 2026
    By Danny BakstMay 1, 2026
    1 day ago

    © 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
    FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.