Human Interest Who Is Ann Winblad? What to Know About Bill Gates' Ex Who Called Melinda a 'Good Match for Him' Ann Winblad, a software entrepreneur and venture capitalist with over 40 years of experience, took annual vacations with Bill Gates after he married Melinda Gates By Maria Pasquini Maria Pasquini Associate Editor, Human Interest - PEOPLE People Editorial Guidelines Published on May 6, 2021 02:49 PM Share Tweet Pin Email Ann Winblad, Bill Gates. Photo: Roger Ressmeyer/CORBIS/VCG via Getty; Inset: Jamie McCarthy/Getty Bill Gates continued to keep ex-girlfriend Ann Winblad in his life after marrying Melinda Gates. 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 Monday. After 27 years of marriage, Bill and Melinda said they "no longer believe we can grow together as a couple in this next phase of our lives" but "will continue our work together" at the Bill & Melinda Gates Foundation. Court documents obtained by PEOPLE showed that Melinda, 56, filed for divorce and stated in the petition that their marriage was "irretrievably broken." As the news spread, so too did Bill and Winblad's years-old quotes about their connection and former relationship. Here's what to know about Winblad. The Surprising Parts of Bill & Melinda Gates' Marriage — Including His Vacations with an Ex 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 page. Then, in 1976, she co-founded her first company, Open Systems, Inc., an accounting software business that went on to sell for over $15 million, the Los Angeles Times reported in 1998. In 1989, she co-founded Hummer Winblad Venture Partners, which was the first venture firm focused entirely on software, the company's website states. Over the years, the firm has launched over 160 companies, according to her company bio. She has also worked as a consultant for a number of 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, 65, and Winblad, 70, 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 a number of trips together, including to Brazil and central 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 when Melinda joined Microsoft as a product manager. According to Time, part of the reason for the split was that Winblad, who is 5 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." "We can play putt-putt while discussing biotechnology," Gates said at the time. Added Winblad: "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 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 to Time in the 1997 story. Want to get the biggest stories from PEOPLE every weekday? Subscribe to our new podcast, PEOPLE Every Day, to get the essential celebrity, entertainment and human interest news stories Monday through Friday. Melinda French Gates and Bill Gates. Frederic Stevens/Getty 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."