Who is Ann Winblad: Bill Gates' ex-girlfriend who Melinda allowed him to jet off annually

Bill Gates' marriage to his estranged wife Melinda Gates certainly featured many undulations on its way to their pending divorce after 27 years.

In fact, in the Gates’ relationship, the tech honcho was allowed by his wife to spend time with an ex-girlfriend thanks to a built-in arrangement Bill had with Melinda French prior to the now-former pair exchanging nuptials in Hawaii in 1994.

The negotiated consideration said that he and software entrepreneur and venture capitalist Ann Winblad would be able to jet off on annual weekend getaways with each other to pick each other’s brains and bask in the old times they shared while creating new memories of their own, this according to a 1997 Time magazine profile on the Microsoft co-founder.

Gates said at the time that he had actually sought approval from Winblad before he made the plunge and proposed to Melinda.

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"When I was off on my own thinking about marrying Melinda, I called Ann and asked for her approval," he said of the woman he bonded fondly with over their mutual love of all things science, adding that Winblad, whom he often played "putt-putt while discussing biotechnology" had given Melinda a favorable evaluation.

"I said she’d be a good match for him because she had intellectual stamina," Winblad – who dated Gates exclusively from 1984 until their split in 1987 – recalled in the piece.

According to her LinkedIn profile, Winblad carries an impressive jacket and has held several posts within Silicon Valley, including runs as Director at companies such as Central Point Software, Hyperion, Net Perceptions, Intrinsa, Liquid Audio, The Knot, Marketwire, Krillion, Inc., Star Analytics, SVForum, Karmasphere, Voltage Security, MuleSoft, Sonatype, Ace Metrix and her current position of nearly 32 years at Hummer Winblad Venture Partners.

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"Even now, Gates has an arrangement with his wife that he and Winblad can keep one vacation tradition alive," Walter Isaacson wrote in the 1997 feature. "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."

Also among their intellectual conversations, the pair would "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."

What’s more, is Gates and Winblad were ahead of their time in the idea that their initial "dates" were virtual as the par weren’t physically together, thus the close-knit connection would be fostered through their discussions of modern films that they each would watch at the same time in whatever city theater was playing the title.

In the Times piece, Isaacson even referred to Gates and Winblad as "kindred spirits."

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In a 2005 interview with the San Francisco Chronicle, Winblad recalled how Gates "wasn’t such a big deal" when she started dating him.

"And there was a period of time when my net worth was higher than his, and I had to pay for everything. It was a very short period of time, but it was memorable," she quipped.

Winblad later told the Silicon Valley Business Journal in 2013 that Gate oozed confidence and she grew fond of his drive to be best.

"Bill and I went for a walk on a beach, and Bill tells me, ‘I can see my way, if I really squint, to $500 million in revenue," she recalled. "Bill was a great influence on me, and I was thinking, ‘Wow, you can actually build a company that big in the software industry? Are you kidding me?'"

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The philanthropist and wealth coach added of Gates: "I remember making him take a stick or a rock and drawing the numbers out on the sand for me. How was he going to get there? He then said, ‘What troubles me is I can’t see how I am going to get past $500 million.’"

"I thought, ‘You’re troubled about that?’" Winblad maintained. "I was jazzed that someone could think their way through to $500 million. There was a lot of inspiration from each other back then because there was so little collective wisdom."

Gates and Winlad’s escapades read like your run-of-the-mill romantic comedy.

In 1996, Winblad told the story of a trip the pair took to Cabo San Lucas for a spontaneous weekend, explaining to Wired magazine that once the two arrived in Mexico, "it was hard to get a rental car, so when we finally got one, it was like this beat-up old Volkswagen, and it was Spring Break."

"So we get a hotel. It’s a sh--ty hotel, but that’s fine because we’re doing this on a whim, and it’s part of the adventure. I leave Bill outside while I check-in," she recalled at the time.

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"Well, I go outside and I say, ‘Where’s the car?’ He goes, ‘I sublet it.’ He rented the car to some teenagers for five dollars a day!" Winblad exuded. "He gave them the car keys and says, ‘We’re in room whatever. Just knock on the door and give us the keys back.’"

"Sort of like ‘I’m Bill Gates; here’s the rental car; here are the keys to our room.’ I’m going, ‘We’re never going to see that car again. These are teenage boys.’"

"He says, ‘You’re probably right.’ … We finally got it back at about two in the morning, and it was all in one piece."

Other stories of the ex-pair that do not involve Melinda was a trip to Brazil in which Gates, the science nerd brought along a 1,100-page textbook on molecular biology — and the duo studied it together, Time magazine said in their 90s feature piece.

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Another included a trip to a ranch in Santa Barbara, Calif., and Winblad supplied tapes of famed physicist Richard Feynman so the couple could listen and digest.

Gates would go on to admit in the same piece that Winblad "brings a sense of enjoyment and humor to even the most serious situations.

"Her professional approach reminds me a lot of Warren Buffett. She is incredibly smart," said Gates, a longtime friend of billionaire Berkshire Hathaway founder Buffett.

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Gates broke the news to the world on Monday that he and Melinda were calling it quits after being married nearly three decades.

The couple said the reason for their dissolution rests on the fact that "we no longer believe we can grow together as a couple in the next phase of our lives."

"Over the last 27 years, we have raised three incredible children and built a foundation that works all over the world to enable all people to lead healthy, productive lives," a tweet from the former pair reads and adds, "We continue to share a belief in that mission and will continue our work together at the foundation."

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Throughout their 27 years as man and wife, the Gates would welcome three children: Jennifer, Rory and Phoebe and would also start their widely philanthropic Bill and Melinda Gates Foundation in 2000.

The pair currently share a net worth of more than $130 billion.

Winblad did not immediately respond to Fox News' request for comment.