In the summer of 1988, Bill Gates took a helicopter to Les Arcs ski resort in the French Alps for an international sales meeting for Microsoft.
He was already the youngest billionaire in history — a title he had held since 1987 — and the 33-year-old computer magnate was in the mood to let loose. Microsoft had rented the entire resort, which was closed for the season, giving employees free rein of the mountainous retreat.
One night, Gates joined his employees for drinks in a Swiss chalet and partied until the sun came up, recalled Dan Graves, a former Microsoft export manager. At about 5 in the morning, Graves nearly tripped over Gates, who was lying on top of a woman out on the lawn. The pair were “just snuggling,” Graves told Insider.
It’s not the kind of story most people think of when they imagine Gates, with his oversized glasses, boyish haircut, and nerdy persona. Till very recently, he was better known for quirky Reddit AMAs, publicly advocating for COVID-19 vaccines, and pumping billions into philanthropic work, alongside Melinda, his wife of nearly three decades.
So when Bill and Melinda Gates announced their divorce in May, the split was met with disbelief, especially when reports of Gates’ extramarital proclivities were published. In 2019, a Microsoft engineer wrote a letter to the company’s board alleging that she had been in a sexual relationship with Gates, spurring an internal investigation by Microsoft’s board. Gates stepped down from the board several months after.
A Bill Gates spokesperson told Insider that Gates had an affair with a Microsoft employee “almost 20 years ago, which ended amicably” and said any claims Gates mistreated employees are false. The spokesperson said the matter was unrelated to Gates leaving the board.
After news of the affair went viral, the squeaky-clean reputation that he and his PR team had meticulously crafted over the years quickly unraveled. Female employees came forward with stories of Gates asking them out to dinner and details about his visits to strip clubs years ago emerged. Meanwhile, his meetings with Jeffrey Epstein, including a flight to Palm Beach on Epstein’s private plane, came under further scrutiny.
Gates’ spokesperson also said Gates had “absolutely no business partnership or personal friendship” with Epstein, and any meetings between the two were about philanthropy.
“It is extremely disappointing that there have been so many lies published about the cause, the circumstances and the timeline of Bill Gates’s divorce,” the spokesperson said. “The rumors and speculation surrounding Mr. Gates are becoming increasingly absurd and it’s unfortunate that people who have little to no knowledge are being characterized as ‘sources.'”
Many who knew Gates said they weren’t surprised by some of the news. “A person like Bill Gates thinks the usual rules of behavior don’t apply to him,” Maria Klawe, a former Microsoft board member, said.
‘Bill yelled at everyone the same’
It wasn’t long after Gates launched Microsoft with his childhood friend Paul Allen that he became known among some employees as an office bully. Four women who worked with Gates at Microsoft told Insider he was brash and hot-tempered.
“Having a meeting with Bill was just an opportunity to get yelled at, so I tried to avoid that,” a former Microsoft executive who spoke on condition of anonymity said.
Gates was known for swearing and berating underlings. “That’s the stupidest fucking idea I’ve ever heard” became a catchphrase for the CEO. He kept tabs on employees by memorizing their license plates. Gates tried to dilute Microsoft cofounder Paul Allen’s equity in the company because he was “unproductive” while dealing with his first bout of cancer, Allen wrote in his memoir.
(Gates’ spokesperson denied that he mistreated employees.)
Another former Microsoft executive who also spoke on condition of anonymity said Gates was direct and honest. While his management style could intimidate some employees, she appreciated his candor. “Bill yelled at everyone the same,” she said.
Another former executive, who had several solo meetings with Gates, said he could be awkward. “He doesn’t know how to joke really or how to connect with people,” she said. “If he told you he liked your hair, he wasn’t trying to flirt with you. He just actually liked your hair.”
As a current Microsoft employee told Insider, “He’s just an awkward human being as far as social interactions go.”
But not everyone was as understanding, particularly when it came to what some saw as Gates’ insensitivity to women’s workplace issues.
Klawe, a Microsoft board member from 2009 to 2015, said that Gates behaved as if he was the “smartest person in the room” and was unreceptive to suggestions about improving diversity in succession planning, which she said often came from female board members in particular.
It was not something Gates “was interested in hearing about,” she felt, adding that Gates would respond to those suggestions with statements like “‘Are you trying to effing destroy the company?’ The message was, ‘Caring about diversity has nothing to do with the success of Microsoft,'” Klawe said.
A Gates spokesperson called that a “gross mischaracterization to suggest that Mr. Gates lacked interest in speaking about or promoting diversity and inclusion at Microsoft.”
While Gates’ affair shocked many, engaging in clandestine encounters with women was something Gates experimented with early in life. When he was 27, he had an affair with a married woman 13 years his senior, the wife of an Osborne Computer executive who lived abroad, James Wallace reported in his biography “Hard Drive: Bill Gates and the Making of the Microsoft Empire.” Gates’ spokesperson did not provide a comment on information from Wallace.
“Bill had a real fondness for older women then,” an Osborne Computer executive, who knew about the affair, told Wallace.
Adam Osborne — who developed Osborne 1, the first commercially successful portable computer — reportedly told Gates to stop seeing his employee’s wife. In response “Gates told Osborne to mind his own business,” Wallace wrote.
Gates may have long been tunnel-visioned when it came to women. In high school Gates described himself as a shy kid, but it didn’t stop him from manipulating his school’s scheduling software, with Allen’s help, so that he would be the only boy in class, Gates told the BBC.
“I was the one who benefited by being able to have the nice girls at least sit near me. It wasn’t that I could talk to them or anything, but they were there,” Gates said.
By the time he got to Harvard, in 1973, he was more confident. He enjoyed stopping by Boston’s Combat Zone, an area known for strip clubs, porn theaters, and prostitution, nicknamed “Satan’s playground,” Wallace told Insider. “He liked going to strip clubs.”
In a 1994 interview with Playboy, Gates explained that he did go to the Combat Zone, but “just because I went there doesn’t mean I engaged in everything that was going on.” He added, “I ate pizza, read books and watched what was going on. I went to the diners.”
Even after Gates began dating Melinda, in 1987, a propensity for socializing and women remained.
On more than one occasion, during nights he wasn’t working his usual 17-hour days, he invited friends and dancers from local all-nude nightclubs to swim naked at his Laurelhurst bachelor pad overlooking Lake Washington, Wallace said.
“Gates himself rounded up the girls and brought them over there,” Wallace said. “I don’t know if he physically transported them or if he just told them where to show up.”
He was a regular attendee of exclusive after-parties at major computer expo trade conferences like Comdex and Demo, where Gates was often the keynote speaker in the late ’80s and early ’90s. “Bill drank, and he got drunk pretty easily,” said Robert X. Cringely, who wrote a popular computer gossip column for InfoWorld around that time.
“All of us will have been at some affair where Bill was clearly impaired. He was happier” drunk, Cringely said.
Gates preferred to keep his romantic options open while he was dating Melinda, and he struggled to commit to her. “Bill wanted to be married, but he didn’t know whether he could actually commit to it and have Microsoft,” Melinda said in an interview for the Netflix docuseries “Inside Bill’s Brain: Decoding Bill Gates.”
She was aware of his womanizing, and as a result the pair broke up for at least a year early in their relationship, according to Wallace. By 1992 they were back together, tying the knot two years later.
But their marriage wasn’t an entirely traditional one. In a 1997 Time magazine article, Gates said that he still went on annual vacations with an ex-girlfriend, the software entrepreneur Ann Winblad.
Gates and Winblad — who dated from 1984 to 1987 — continued their tradition of spending a long weekend together every spring at Winblad’s beach cottage on the Outer Banks of North Carolina. “We can play putt-putt while discussing biotechnology,” Gates told Time.
The Microsoft founder broke work and personal boundaries, too, The New York Times reported. Once, after attending a presentation given by a female Microsoft employee in 2006, he asked her out to dinner by email. “If this makes you uncomfortable, pretend it never happened,” Gates wrote in the email obtained by The Times.
On another occasion, Gates asked a Gates Foundation employee on a date while they were at a cocktail party in New York. “I want to see you. Will you have dinner with me?” he asked her in a low voice, the woman told The Times.
Melinda herself was an employee at Microsoft when Gates first asked her out. She was hired as a product manager in 1987, and Gates flirted with her at a conference dinner where they first met. A few months later, they ran into each other in a parking lot and he asked her to dinner, Melinda said in an interview.
‘Everything was siloed, always’
At the turn of the millennium, the Gateses announced their titanic vessel for philanthropy, The Bill & Melinda Gates Foundation. The foundation has donated $1.3 billion to fight malaria, $86 million toward eradicating polio, and pledged $1.7 billion to pay for initiatives in public education.
The couple’s personal affairs have been managed by Watermark Estate Management, a single family office, since at least 2001. Watermark deals with everything that doesn’t touch Microsoft or the foundation, from the family’s housekeeping to their helicopters. It planned holiday vacations and hired armed guards to discreetly keep watch over the couple’s $131 million estate in Medina, Washington. It also arranged Gates’ annual beach trips with Winblad.
But while Bill and Melinda presented themselves as a synchronized philanthropic power couple, the operations of their lives had begun to grow apart.
In 2008, Gates launched bgC3, a private office-style entity that focused on the Microsoft cofounder’s interests outside Microsoft and outside his marriage. It was a “third leap into something new,” a former bgC3 employee said.
Early trademark filings for bgC3 — which stands for “Bill Gates Catalyst 3” — described the firm as a think tank aimed at using technology to fight poverty. Gates’ functions included routine travel for non-Microsoft speaking engagements and the management of GatesNotes, the blog where Gates publishes his revered book lists.
In practice, bgC3 represented a private fiefdom for Gates, with its own reporting structure, security team, and budget — distinct from Watermark and far from Melinda’s oversight. Employees at the shared family office had little visibility or control over what happened under bgC3’s jurisdiction, and information rarely moved between the two entities except for when it came to coordinating logistics.
“Everything was siloed, always,” the former employee said.
This arrangement allowed Gates to spend money and pursue independent interests that later factored in the breakdown of the couple’s marriage. In 2014, when Jeffrey Epstein coordinated a $2 million donation from the tech billionaire to MIT, that money came directly from bgC3 — not from the Gates Family Foundation, which normally handled his philanthropic givings.
Gates’ relationship with Epstein dates to 2011, but it became a point of contention for the couple in September 2013, soon after Melinda joined her husband to meet the convicted sex offender at his Upper East Side mansion, The Daily Beast reported. Melinda told friends that she was furious about the two men’s friendship, and wanted nothing to do with Epstein, according to the report.
But her intervention didn’t appear to work. Gates visited Epstein’s house numerous times, according to a source close to Epstein, and the sex offender frequently name-dropped Gates and claimed to be his advisor.
Over the course of their years-long friendship, Gates reportedly vented to Epstein about his “toxic” marriage with Melinda, and in turn Epstein gave Gates advice on ending his marriage, people told the Beast.
In 2015, Melinda formed her own personal office, Pivotal Ventures, which focused its investments and philanthropy on women’s equality. She took a number of Watermark people to work with Pivotal Ventures, a former Watermark employee told Insider, though the family office continued to work closely with Melinda.
Sources from both Watermark and bgC3 spoke positively about the professionalism and culture of the two organizations.
The family office’s operations became a model for other newly minted tech billionaires looking to organize their lives, with the likes of the Zuckerbergs looking to them for guidance on how to manage household affairs, two former Zuckerberg employees said.
Other elements of the Gates’ marital arrangements remain unclear. Despite recent reports that the two didn’t have a prenup, a 1995 article in Upside magazine said that not only did Melinda sign a prenup but Gates sent Steve Ballmer — who later succeeded Gates as Microsoft CEO — to get her to sign it.
“Sure, it seemed crass to have his closest pal deliver the prenuptial agreement to Melinda, but then Ballmer was a terrific negotiator,” the article said. “With him pitching the deal, Melinda signed on the dotted line.”
Asked by Insider about the article, G. Pascal Zachary, the journalist who wrote it, said, “I stand by all of the things I wrote because I took very seriously accuracy and if there were any complaints, I would have corrected them.” After publication, a Gates spokesperson referred Insider to a 1999 CBS article recapping a Gates interview on the “60 Minutes” television program in which the Microsoft founder refuted reports of a prenup.
Microsoft and the press
Microsoft’s publicists have gone to great lengths to protect Gates’ personal life, journalists and Microsoft insiders said.
“Microsoft was spoon-feeding some of the well-known journalists who covered Microsoft really good stories, and in an exchange they were keeping some of these trashy stories in their notebooks,” Wallace said. “There were some big-name journalists who knew about this behavior, and they never reported on it because they knew Microsoft would have taken away their access.”
One former executive added that Microsoft’s PR team was “very controlling of the message” and “overly worried about perception.” Microsoft did not provide a comment to Insider.
Gates stayed close to the press, so much so that he gained a reputation for hitting on female reporters who covered industry conferences such as Comdex, Wallace said. “The journalists said that it was their understanding that they weren’t the only ones either,” he added.
The relationship between Microsoft and Ziff Davis, one of the major tech magazine publishers of the time, came into question publicly in 1992 when columnist Will Zachmann published an article critical of Gates and his job contract wasn’t renewed.
“They’re in bed with Microsoft every which way from Sunday,” Zachmann told Wired.
But once Melinda divorced Gates “the halo broke,” a Microsoft employee told Insider. “Anyone who had stories could bring all those stories out.”