Ann Winblad is Bill Gates’ ex-girlfriend, with whom Melinda gave him permission to travel annually.


In reality, the Gates’ marriage permitted the software tycoon to spend time with an ex-girlfriend because of a pre-existing agreement Bill made with Melinda French before the now-ex-couple exchanged vows in Hawaii in 1994.

According to a 1997 Time magazine profile on the Microsoft co-founder, the negotiated consideration stated 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.

At the time, Gates said that before popping the question to Melinda, he really got Winblad’s blessing.

He recalled the woman he grew close to through their shared love of science, saying, “When I was off on my own thinking about marrying Melinda, I called Ann and asked for her approval,” adding that Winblad, with whom he frequently played “putt-putt while discussing biotechnology,” had given Melinda a favorable assessment.

Winblad dated Gates exclusively from 1984 until their breakup in 1987. “I felt she’d be an excellent fit for him since she had intellectual stamina,” Winblad remembered in the article.

Winblad has held several positions in Silicon Valley, including runs as Director at businesses like 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, according to her LinkedIn profile. She also sports an impressive jacket

In the 1997 article, Walter Isaacson stated that “Even now, Gates has an agreement with his wife that he and Winblad can keep one vacation ritual alive.” Gates and Winblad spend a long weekend together each spring at Winblad’s beach house on the North Carolina Outer Banks, where they go hang gliding, ride dune buggies, and take beach walks.

The two would “marvel at how, as two young overachievers, we began a fantastic adventure on the edges of a little-known business and it landed us at the heart of an astonishing universe” as part of their philosophical discussions.
Furthermore, Gates and Winblad were ahead of their time in the notion that their first “dates,” since they weren’t physically present, would be virtual and that their close bond would be developed through discussions of contemporary movies that they would both watch at the same time in whichever city theatre the movie was playing.

Winblad said that when she first started dating Gates, “he wasn’t such a huge deal” in a 2005 interview with the San Francisco Chronicle.
Later, in 2013, Winblad told the Silicon Valley Business Journal that Gate exuded confidence and that she had grown to admire his desire to be the greatest.

Bill told her, “I can see my way, if I really squint, to $500 million in income,” while they were strolling down the beach, she recounted. “Bill had a significant impact on me, and I remember thinking, “Wow, you can really grow a firm that big in the software industry? Is this thing on?
Gates was told to create the numbers for me on the beach using a stick or a rock, the philanthropist and wealth coach continued. How would he go there? What concerns me is that I can’t see how I am going to get over $500 million, he continued.

“You’re bothered about that?” I wondered. Winblad affirmed. “I was thrilled that someone had the mental capacity to reach $500 million. Because there was so little accumulated knowledge back then, people often found inspiration from one another.
When the two landed in Mexico, Winblad explained to Wired magazine that “it was hard to acquire a rental car, so when we eventually got one, it was like this beat-up old Volkswagen, and it was Spring Break.” The two had travelled to Cabo San Lucas for an unplanned weekend.

Thus, we book a hotel. It’s a lousy motel, but because we’re doing this on a whim and it’s an adventure, it’s okay. I check in and leave Bill outside,” she recounted at the time.
I venture outside and inquire, “Where’s the car?” Then he says, “I sublet it.” He charged several teens $5 per day to use the automobile! Winblad radiated. He handed them the keys to the car and announced, “We’re in room whatever. Give us back the keys by knocking on the door.

‘I’m Bill Gates; here’s the rental vehicle; here are the keys to our hotel,’ sort of thing. We won’t ever see that automobile again, I’m saying. These are adolescent lads.
“You’re probably correct,” he says. At around two in the morning, we finally received it back, and everything was intact.

Other tales about the former couple that do not involve Melinda include a trip to Brazil when Gates, the scientific nerd, carried a 1,100-page textbook on molecular biology with him. The couple read the book together, according to an article in Time magazine from the 1990s.
Another was a visit to a property in Santa Barbara, California, where Winblad gave the couple cassettes of renowned scientist Richard Feynman so they could listen and take them in.

Gates later acknowledged that Winblad “brings a sense of delight and laughter to even the most severe events” in the same article.
“Her businesslike demeanour makes me think a lot of Warren Buffett. Gates, a longtime friend of Buffett, the billionaire founder of Berkshire Hathaway, said of the woman, “She is really clever.
After nearly three decades of marriage, Gates announced to the world on Monday that he and Melinda were divorcing.

The pair said that “we no longer think we can develop together as a couple in the next part of our life” as the basis for their separation.
The former couple wrote in a tweet that they “continue to share a belief in that mission and will continue our work together at the foundation” and that “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.”
The Gates welcomed three children during the course of their 27 years of marriage—Jennifer, Rory, and Phoebe—and established the well-known Bill and Melinda Gates Foundation in 2000.

They presently have a combined net worth of about $130 billion.

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