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

Bill Gatescontinued to keep ex-girlfriend Ann Winblad in his life after marryingMelinda Gatesin 1984.
Details about the billionaire Microsoft co-founder’sbond with Winbladin the ’80s and ’90s resurfaced in the days after he and Melindaannounced their divorcein ajoint statement on Twitterin May 2021.
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.
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 herLinkedIn. Then, in 1976, she co-founded her first company, Open Systems, Inc., an accounting software business that later for over $15 million, theLos Angeles Timesreported in 1998.
In 1989, she co-foundedHummer 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 fromTIME.
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,TIMEreported. They also went on many trips together, including to Brazil and Africa, according to the outlet.
Ann Winblad in 1987.Ann E. Yow-Dyson/Getty Images

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

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 toTIME, 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.George Frey/The LIFE Images Collection via Getty Images/Getty Images

Ann Winblad.Roger Ressmeyer/CORBIS/VCG via Getty Images


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 toTIMEin the 1997 story.
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Melinda French Gates and Bill Gates.Frederic Stevens/Getty

As for Winblad, she told the outlet that she thought Melinda would “be a good match for him because she had intellectual stamina.”
source: people.com