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Who Is Ann Winblad? What to Know About Bill Gates' Ex Who Called Melinda a 'Good Match for Him'

Ann Winblad, Bill Gates
Ann Winblad, Bill Gates

Roger Ressmeyer/CORBIS/VCG via Getty; Inset: Jamie McCarthy/Getty Ann Winblad, Bill Gates

Bill Gates continued to keep ex-girlfriend Ann Winblad in his life after marrying Melinda Gates in 1984.

Details about the billionaire Microsoft co-founder's bond with Winblad in the '80s and '90s resurfaced in the days after he and Melinda announced their divorce in a joint statement on Twitter in May 2021.

After 27 years of marriage, Bill and Melinda said they no longer believed they could grow together as a couple in the next phase of their lives but vowed to continue working at the Bill & Melinda Gates Foundation. Court documents obtained by PEOPLE showed that Melinda filed for divorce and stated in the petition that their marriage was "irretrievably broken."

As the news spread, so did Bill and Winblad's years-old quotes about their connection and former relationship. Here's what to know about Winblad.

RELATED: The Surprising Parts of Bill & Melinda Gates' Marriage — Including His Vacations with an Ex

Ann Winblad
Ann Winblad

Roger Ressmeyer/Corbis/VCG via Getty Images

Winblad Has an Extensive Background in Business

Winblad has over 40 years of experience in the software industry.

She began her career working as a systems analyst at Minneapolis' Federal Reserve Bank, according to her LinkedIn. Then, in 1976, she co-founded her first company, Open Systems, Inc., an accounting software business that later for over $15 million, the Los Angeles Times reported in 1998.

In 1989, she co-founded Hummer Winblad Venture Partners, the first venture firm focused entirely on software, per the company's website. Over the years, the firm has launched over 160 companies, according to her company bio. She has also worked as a consultant for several companies, including IBM and Microsoft.

Bill and Winblad Began Dating in the 1980s — Before He Met Melinda

The pair began dating in 1984 after meeting at a computer conference, according to a 1997 story from TIME.

Bill and Winblad then began going on "virtual dates," watching movies at the same time from whatever cities they were in, and then calling each other on the phone to discuss what they saw, TIME reported. They also went on many trips together, including to Brazil and Africa, according to the outlet.

Ann Winblad
Ann Winblad

Ann E. Yow-Dyson/Getty Images Ann Winblad in 1987

Ann Winblad
Ann Winblad

Ann E. Yow-Dyson/Getty Images Ann Winblad in 1991

Bill and Winblad Stayed Close After Their 1987 Split, Even Vacationing Together

Bill and Winblad split in 1987, the same year Melinda joined Microsoft as a product manager. According to TIME, part of the reason for the split was that Winblad, who is five years older than Gates, was more ready for marriage.

However, Bill developed such a strong bond with Winblad that Bill made sure to keep her in his life after their 1987 split.

"Even now, Gates has an arrangement with his wife that he and Winblad can keep one vacation tradition alive," Walter Isaacson reported in the resurfaced story. "Every spring, as they have for more than a decade, Gates spends a long weekend with Winblad at her beach cottage on the Outer Banks of North Carolina, where they ride dune buggies, hang-glide and walk on the beach."

Bill added at the time, "We can play putt-putt while discussing biotechnology."

Winblad continued: "We share our thoughts about the world and ourselves. And we marvel about how, as two young overachievers, we began a great adventure on the fringes of a little-known industry, and it landed us at the center of an amazing universe."

Winblad did not immediately respond to PEOPLE's request for comment.

Ann Winblad
Ann Winblad

George Frey/The LIFE Images Collection via Getty Images/Getty Images Ann Winblad

Ann Winblad
Ann Winblad

Roger Ressmeyer/CORBIS/VCG via Getty Images Ann Winblad

Ann Winblad
Ann Winblad

Roger Ressmeyer/CORBIS/VCG via Getty Images Ann Winblad

RELATED VIDEO: Melinda Gates Calls Marriage to Bill 'Irretrievably Broken,' Declines Spousal Support Despite No Prenup

Bill Sought Approval from His Ex-Girlfriend Before Proposing to Melinda

When it came time for Bill to propose to Melinda, he asked Winblad for her permission.

"When I was off on my own thinking about marrying Melinda, I called Ann and asked for her approval," he recalled to TIME in the 1997 story.

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bill and melinda gates
bill and melinda gates

Frederic Stevens/Getty Melinda French Gates and Bill Gates

RELATED: Bill and Melinda Gates File for Divorce — What's Now at Stake for the Billionaires

As for Winblad, she told the outlet that she thought Melinda would "be a good match for him because she had intellectual stamina."