Was Ann Winblad’s relationship with Bill Gates partially to blame for the billionaire couple’s split? It’s not yet clear. But what is clear is the Microsoft founder was close with a number of women during his marriage to Melinda.

Bill Gates’ ex-girlfriend, Ann, reportedly took Bill on annual wild getaways throughout his marriage to Melinda Gates. The billionaire philanthropist supposedly had an arrangement with his wife, spelling out intentions to fly around the world with Winblad on weekend getaways.

Ann and Bill were lovers from 1984 to 1987, before Microsoft truly took off as one of the world’s leading tech companies. The two shared great memories during their relationship, as two young entrepreneurs trying to make their way in the tech industry.

“Bill and I went for a walk on a beach,” Ann recalled one memorable moment of their time together. “Bill tells me, ‘I can see my way, if I really squint, to $500 million in revenue. 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?'”

Ann Winblad was very intelligent, and Bill had great respect for her. He’d often go to her for support and counsel. In his first leg on his race to the top spot on Forbes, he’d discuss his strategies with Ann. “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.’”

Ann Winblad with Bill Gates
Ann Winblad with Bill Gates. Photo Credit: HitC and Ann E. Yow-Dyson/Getty Images

Despite ending their relationship after three years, Ann and Bill stayed close. The Microsoft founder was keen on keeping Ann’s bright mind nearby and he continued to pick at it, even after meeting and courting Melinda French.

“When I was off on my own thinking about marrying Melinda, I called Ann and asked for her approval,” Bill told Time Magazine. Winblad added that she believed Melinda was a good match for Bill, because of her “intellectual stamina.”

Before Bill and Melinda tied the knot an agreement was reportedly put in place, that Bill and Ann could still go on their weekend adventures once a year, so he could reset, recall, and pave a way forward. Walter Isaacson wrote in the Times back in 1997 that “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.”

The excursions were a way for Bill to unwind and engage in intellectual conversations with his ex-girlfriend. They 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.”

Ann Winblad has her own identity away from Bill, with an impressive list of high-profile positions at Silicon Valley throughout the years. She started a venture capitalist firm that invests in innovations in the tech industry. Together, Bill and Ann were ahead of their time. They were “kindred spirits,” according to the Times piece, and would study together.

Bill Gates and Ann Winblad would discuss biotechnology while playing mini-golf and even studied a 1,100-page molecular biology textbook during a trip to Brazil. They had wild adventures together, even through Bill’s 27 years with his wife, Melinda.

There is no telling whether Bill and Ann will continue to see each other now that Bill and Melinda Gates are splitting. The ending of the nearly three-decades-long marriage was announced on Monday when Bill and Melinda took to Twitter. They explained that “After a great deal of thought and a lot of work on our relationship, we have made the decision to end our marriage.”

The billionaire pair will have to divide a $130 billion fortune, but they have announced that their $51 billion foundation, The Bill and Melinda Gates Foundation, will continue after their separation.