Details About Ann Winblad, Bill Gates' Ex-Girlfriend Melinda Let Him Vacation With Every Year

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Bill Gates and Ann Winblad

Amid Bill and Melinda Gates’ divorce, more is being revealed about Gates’s ex-girlfriend, Ann Winblad, with whom he has maintained a close relationship over the years.

Speculation about Gates’ close relationship with his ex resurfaced after the shocking revelation that he and Melinda would be separating after 27 years of marriage.

The couple released a joint statement saying they, "no longer believe we can grow together as a couple in this next phase of our lives.”

Court documents showed that Melinda filed for divorce and stated in the petition that their marriage was "irretrievably broken."

Now, as people try to make sense of the couple’s surprising split, old quotes and interviews from the Microsoft founder have resurfaced. His comments reveal a close relationship with former girlfriend Winblad, who he vacationed with throughout his marriage to Melinda.

Who is Bill Gates' ex-girlfriend, Ann Winblad?

Ann Winblad, the ex-girlfriend with whom Bill Gates reportedly remained close — maybe a little too close — decades after their breakup is a tech entrepreneur and venture capitalist from Minnesota who once described herself as a "5-foot 2.75-inch, 105-pound package of north country friendliness."

Photo: Frederic Legrand, COMEO / Shutterstock.com

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Here’s everything you need to know about Winblad, her relationship with Bill Gates, and the arrangement between them Melinda Gates is said to have approved.

Winblad, grew up in the small town of Red Wing, MN, 25 miles south of the Twin Cities.

The oldest of five kids, she earned a scholarship to attend the College of St. Catherine in St. Paul, where she studied math and business administration before earning her master's degree in international economics and education from the University of St. Thomas.

Bill Gates and Ann Winblad dated in the 1980s.

Gates and Winblad dated from 1984 to 1987, after meeting at a computer conference just before Microsoft went public.

In a 1997 interview with Time Magazine, Gates revealed that, when they were dating, the jet-setting pair used to go on virtual dates over their cell phones, and that they loved traveling together to spots as near as Santa Barbara and as far as Brazil and Africa.

In 1987, the pair split because Winblad, now 70 and five years older than Gates, was ready for marriage and children before he was.

Melinda had joined Microsoft as a product manager that same year.

The former couple's breakup and subsequent marriages didn’t stop them from remaining friends.

Gates even called up his ex-girlfriend to ask for her approval before he proposed to Melinda, which Winblad granted.

"I said she'd be a good match for him because she had intellectual stamina," Winblad said.

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Gates and Winblad vacationed together, even after Bill and Melinda married.

The tech-mogul also revealed that made a deal with his then-new wife Melinda that he would be able to maintain his vacation tradition with Winblad.

"Every spring," the article explains, "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.

Winblad expanded, saying, "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."

Like Bill and Melinda Gates, Winblad works in the software industry.

Winblad is a successful figure in the technology world in her own right.

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She has held several impressive posts in the Silicon Valley, including stints as the director at companies such as Central Point Software, Hyperion, Net Perceptions, The Knot and Marketwire.

In 1976, the software entrepreneur co-founded accounting software firm Open Systems Inc. with nothing more than a $500 investment. She went on to sell the company in for over $15 million in 1998.

Winblad can frequently be seen offering her financial analysis on CNBC, and she has given multiple Ted Talks, such as this one from 2012 titled, "Talent in the post-internet age."

It’s no wonder she and Gates have bonded so closely over the decades.

Some sources estimate Winblad’s net worth to be $15 million based on the sale of her company alone, but as she is such a private figure this number is difficult to confirm.

She is currently listed as the Managing Director and Founding Partner of Hummer Winblad Venture Partners, the first venture firm focused entirely on software.

Who is Ann Winblad’s husband?

Winblad is married to Edward Alex Kline, who goes by Alex. Kline is the younger brother of actor Kevin Kline.

Winblad and Kline married in 2015 and don’t share any biological children. Kline, however, has adult children from a previous relationship.

Kline is a private investigator who runs his own company, Alex Kline Investigation and Research Service.

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Alice Kelly is a writer living in Brooklyn, New York. Catch her covering all things social justice, news, and entertainment. Keep up with her on Twitter for more.