By now, many know the legend of Eric Schmidt—how, back in 2001, Google’s young co-founders, Larry Page and Sergey Brin, brought him into the company in its critical early years to be “the adult in the room” and instill discipline in their unruly, fast-growing start-up.

The boys—28 and 27 years old at the time—had first hoped Steve Jobs might take the gig. Not to be. Later they were introduced to Schmidt, a seemingly mild-mannered 46-year-old in a baggy suit who was C.E.O. of Novell, a software company that was losing ground to Microsoft. On the surface the three didn’t seem to have much in common. Until, that is, the conversation turned to Burning Man, the quasi-apocalyptic, sometimes druggy, often free-swinging sex-fest in the Nevada desert, of which Sergey and Larry were big, big fans.

“So am I!,” Schmidt said.

Well now.

Schmidt was the third candidate to be offered the job, and the first one to say yes. His compensation that first year was $250,000, plus a bonus of $300,000, but that all paled in comparison to the 14.4 million Google shares—6 percent of the company—he also received.

By many metrics, Schmidt succeeded wildly. Marissa Mayer, an early Google employee who later was C.E.O. of Yahoo, tells me, “Eric was able to see around corners in ways that nobody else could. Including the founders.” He got the company focused on a mission, and in doing so helped it to become the behemoth it is—mostly by convincing Page and Brin to turn the search engine into a gigantic advertising machine.

“Eric kept us laser-focused on how to build the best in what actually mattered,” Mayer says.

Schmidt with (from left) Arianna Huffington, Frances Beinecke, and his wife, Wendy Schmidt, in 2011.

He also guided it to its landmark I.P.O., in 2004, which raised $1.9 billion. It was a deal that made the founders spectacularly wealthy, as it did Schmidt. (Since then, the stock is up some 4,400 percent. Google’s ad revenue in the first quarter of 2021 was nearly $45 billion, and the company is now the fifth most valuable in the world.)

Still, in Silicon Valley, Schmidt is a bit of an outlier. Always has been. And unlike many of the top names on the Bloomberg Billionaires Index—Bezos ($195 billion); Musk ($171 billion); Gates ($146 billion); Zuckerberg ($112 billion); Page and Brin ($105 billion), all of whom built businesses from their own ideas—Schmidt (No. 74, with a worth of $24 billion) has created exactly … nothing.

In other words, Schmidt got rich the old-fashioned way. He is one of the few people on the Bloomberg list who became hyper-wealthy not by what he made but by the moves he made—specifically, by latching onto the right people at the right time and then making what they made better.

Schmidt was the third candidate to be offered the job, and the first one to say yes. His compensation that first year was $250,000.

Yet while Brin and Page hired Schmidt to be the adult in the room, across the years he has gained a reputation for being just about anything but—at least when it comes to social mores and women who are not his wife. These days, thanks to Jeff Bezos’s and Bill Gates’s dramatic busts from their respective first wives, MacKenzie and Melinda, it might appear that tech dudes are going through something of a market re-alignment, at least with their significant others.

But for all the drama surrounding Bill and Jeff, these two seem positively, well, adult next to Schmidt. Technically, the wayward former Google C.E.O. is still married to Wendy Schmidt—but he enjoys the benefits of a marriage that is, as it were, a very open and, at times, a very awkward secret.

Wendy Schmidt in 2013.

As one person who has spent time with Brin and Page tells me, “Eric was a serial, very evident philanderer.... And I know that it drove a lot of people crazy around Google, not just Larry and Sergey. They just basically didn’t like him.” Which makes you wonder why Brin and Page turned a blind eye to Schmidt’s behavior for so long, and if his antics ultimately made him a corporate liability they had to defease. (Google did not respond to requests for comment.)

A Ship in Every Port

Wendy Susan Boyle—“tall, blond and whippet thin,” as The New York Times once described her—married Eric Schmidt 41 years ago this month. She was born in Short Hills, New Jersey, and met Schmidt at the University of California, Berkeley, where she was studying for a master’s degree in journalism and he was a doctoral student in computer science. (She edited his thesis; hers was about nuns.)

Together they had two daughters (one died in 2017), and although they finally physically, if not legally, separated in 2011, they had an open relationship long before that—an openness that Eric Schmidt appears to have wanted, and that Wendy addressed (sort of) to a New York Times reporter in 2012: “I think [the rumors] are nonsense and, between us, if we know what is going on in our lives and we are happy, that kind of stuff is part of his being in the public eye,” she said. “You know, people will write things. You just have to ignore them.”

Schmidt got rich the old-fashioned way. He is one of the few people on the Bloomberg list who became hyper-wealthy not by what he made but by the moves he made.

One of Schmidt’s first extramarital relationships was with Marcy Simon, a well-known New York public-relations executive, which reportedly began in 2006. At the time, Simon didn’t hide her relationship with Schmidt and would often casually tell reporters about her new “boyfriend.” Schmidt made no efforts to keep the relationship on the DL, either. Certainly not professionally: some people think he hired Simon to do public relations for Google.

This arrangement “became a source of anger” at the Mountain View campus, says one longtime Google observer, “that Eric would have them hire one of his girlfriends to do P.R.” Now, this person continues, Simon was a “competent P.R. person, no question,” but “Eric [was] making Google hire a P.R. person who he’s having an affair with. I mean it really became an issue among some at Google, that it was really bad judgment.” (Schmidt declined to comment for this story. A person close to him says that “a different Google executive, not Eric, discussed bringing Simon on board to do work for the company, but that never actually happened,” and conceded that Schmidt’s relationship with Simon was “an exercise in poor judgment, for sure.”)

“No, you see, Eric, Fatal Attraction was fiction. I only played a character.” Schmidt with Michael Douglas at a party.

According to another well-informed person, Simon also acted as the “go-between” for Schmidt and former president Bill Clinton. At least once a year while Schmidt was C.E.O., Clinton’s office would arrange for Clinton and his entourage to use the Boeing 757 that Page, Brin, and Schmidt had outfitted for their personal use. Clinton and company would wangle it for a 10-day-or-so philanthropic trip to Africa, or some other exotic location. Simon would arrange for the use of the plane with Schmidt, who gave the O.K.—as long as the trip was for philanthropic reasons, which were not hard to supply, given Clinton’s involvement. (Simon did not respond to requests for comment.)

“Use of the plane means we don’t pay for anything, not the food, not the fuel, not the landing rights, all that stuff,” someone in Clinton World tells me. “So that was a big deal,” worth millions of dollars in avoided costs. “That was standard operating procedure,” this person continues. “The excuse was we were out there doing philanthropic projects. By asking to use this, we were using it for good. It’s not like Clinton was taking the plane to go give a speech and make money. They were careful not to do that.”

What Schmidt and Google got out of the deal was harder to discern, other than to be in the Clintons’ good graces. And yet. “Do you ever hear Bill Clinton be critical of Google in any of these public debates about Google or Facebook or any of these other things?” the Clinton insider continues. (Jon Davidson, a staffer in Clinton’s office, did not respond to a request for comment.)

After Simon came Kate Bohner. “Simon made Bohner’s life miserable,” says someone who knows them both. Bohner, who co-wrote The Art of the Comeback for Donald Trump and was also briefly married to best-selling author Michael Lewis, first met Schmidt in the mid-1990s, when he was still at Novell. She was a columnist at Forbes at the time and part of the team writing a piece about Schmidt. (Before Forbes, Bohner worked briefly with me at Lazard, where she was a financial analyst, after which she was off to the Graduate School of Journalism at Columbia University.) She also had on-air stints at CNBC and at E-Trade, during the online brokerage’s ill-fated run as a financial-news broadcaster.

One of Schmidt’s first extramarital relationships was with Marcy Simon, a well-known New York public-relations executive.

Early in Schmidt’s tenure as the Google C.E.O., the two reconnected and were supposed to have dinner. But that didn’t happen. A few years later, in late 2006, Schmidt reached out again to Bohner, who had moved to Florida. He asked if she wanted to make videos for YouTube, which Google had just bought for $1.65 billion. Her YouTube show was called The Watercooler Diaries. Eventually, she fell in love with Schmidt and moved part-time to Atherton to be with him, even though she hated California.

They were very compatible. They had similar interests. They’d meet up for the weekend in New Orleans or in Chicago, where they’d go on boat rides to look at the architecture. They would occasionally fly together on Schmidt’s private jet. But usually she would fly commercial to meet him for the weekend, if they weren’t already together. Schmidt was cheap. They would buy shoes for him at Cole Haan. She once bought him two Loro Piana cashmere sweaters. He couldn’t believe the price.

She met Schmidt’s daughters but never met his wife. Bohner was always under the impression that the Schmidts were in the process of getting a divorce and that she might well be the new Mrs. Schmidt. Bohner “was able to somehow justify it, because Wendy was never around,” says a person who knows both Bohner and the Schmidts. “She was never in California.”

Bohner had keys to Schmidt’s house and to his car. She and Schmidt had dinner occasionally with Page and Brin and their wives. They took the 757 on a three-week trip to South America to celebrate her 40th birthday.

Marcy Simon; Lisa Shields; Wendi Deng

When they were apart, Schmidt texted her when he woke up to wish her a good morning and called her every night before she went to bed as he was driving home from Google. He adored her and treated her well.

But after nearly five years with him, Bohner got tired of the press attention, which described her as Schmidt’s “mistress,” and it was becoming clear that Eric and Wendy weren’t getting divorced. The relationship ended.

Schmidt was cheap. They would buy shoes for him at Cole Haan.

After Bohner and Schmidt broke up, Schmidt dated a lot of women. According to Vanity Fair, Schmidt dated Lisa Shields, a vice president for media relations at the Council on Foreign Relations, and Wendi Deng, the former wife of Rupert Murdoch.

In a note to herself that Vanity Fair obtained, Deng was clearly jealous of Schmidt and Shields. “Lisa will never have my style, grace,” Deng wrote. “I achieved my purpose of Eric saw me looking so gorgeous and so fantastic and so young, so cool, so chic, so stylish, so funny and he cannot have me. I’m not ever feel sad … about losing Eric … Plus he is really really ugly. Unattractive … and fat. Not stylish at all try to wear hip clothes.... I’m so so soo soooo happy I’m not with him.”

In July 2013, the New York Post reported that Schmidt had bought a penthouse in the Flatiron District of Manhattan for $15 million—other publications referred to it less charitably as his “sex palace”—and that he had been linked to Danya Perry, the deputy general counsel to Revlon owner Ronald Perelman, and Ulla Parker, a former Wilhelmina model. He reportedly gave Alexandra Duisberg a 10-carat pink-sapphire ring on a 2019 trip to Greenland—merely a “friendship ring,” a spokesman for Schmidt said—and that she froze her eggs in hopes that they would have children together. “He likes to have a ship in every port,” one of the women told “Page Six.”


Near the end of December 2017, Schmidt announced he was leaving Alphabet, Google’s parent company. “The time is right,” he said. But others believe the timing was intentional, especially as the #MeToo movement was becoming an international phenomenon in the wake of the stunning revelations about Hollywood mogul Harvey Weinstein. The two Google founders were said to be worried that Schmidt’s well-publicized extramarital affairs would come back to bite him and then Alphabet. (Google didn’t respond to requests for comment.)

“He was scared,” says someone who talked with Schmidt regularly during this period. “He was really fucking scared. And I don’t blame him, because reporters were just going after anybody—he had a bull’s-eye on him. I mean anybody that had that kind of stature.” This person says that while Schmidt’s “personal life is a mess,” he was a potential target for the #MeToo crosshairs because he was the former C.E.O. of Google and was very wealthy. “But I just never got the feeling it went into his professional realm,” the source continues about Schmidt’s extramarital affairs, “but that definitely made him more targeted, there’s no question.” In any event, there have never been any #MeToo stories about Schmidt. (A friend of Schmidt’s says he has a “complicated personal life” but not a “messy” one.)

The funny thing about Schmidt and all this swordsman stuff is that his closest friends claim not to know anything about his personal life and use the same word to describe him as many do: “nerd.” Jared Cohen, a former State Department official whom Schmidt recruited to be the C.E.O. of Google Ideas (now the independent company Jigsaw), recalls how traveling around the world with Schmidt was always a bit of an odd adventure.

Hello, ladies.

“He does things that people in his position wouldn’t do,” Cohen says. “He talks to people who people in his position wouldn’t talk to. He explores things people in his position wouldn’t explore.” In Turkistan, Schmidt would spend hours with the hotel staff debugging its I.T. infrastructure. “He was having fun doing it,” Cohen says.

They’d fly together, to some 50 countries all told, including North Korea. “We went there before Dennis Rodman,” Cohen says—on a combination of Schmidt’s private jet and commercial airplanes. Schmidt loved flying on A380s.

“It’s one of the most annoying things you could imagine because he doesn’t let you go to sleep, because he spends an hour talking to you about how the engine on the A380 works,” Cohen says.

His one criticism of Schmidt, he says, is that he doesn’t do relaxation. “You’re never going to find Eric on a beach or hanging out at a resort or doing leisurely things,” he continues. “That’s just not what he does.” Rather, Schmidt wakes up every day, asks himself what he’s curious about, and then lets that curiosity—about people, or trends, or things—define what he does. “He is probably the most ‘in the present’ person that I know,” Cohen says. “He’s kind of long-term about where the world is going. The way that he lives really is as simple as: ‘I think this is really interesting. I want to learn more about it. What’s the best way to learn more about it? Who should I talk to? Where should I go? What context should I put myself in?,’ and he just does it.”

These days, Schmidt is focused on his philanthropy. There’s the Schmidt Family Foundation, founded by Eric and Wendy in 2006. In 2019, the couple announced a new $1 billion philanthropic commitment. They also started Schmidt Futures in 2017, which makes bets on exceptional people for them to pursue their dreams.

For her part, Wendy Schmidt can be found pursuing her dreams on Nantucket, where she’s been a summer resident since she fell in love with the place in 1999 and bought a house there overlooking the harbor. Since then she has used her great wealth to fund various arts and preservation initiatives, including the creation of Dreamland, a high-end movie theater and performance space.

But others believe Schmidt misses the power and influence he had when he was leading Google and, later, while he was at Alphabet. One former close friend remembers how quickly he used to answer every single e-mail, usually within 24 hours, and how “super-depressed” he would get on Thanksgiving, on Christmas, and on the Fourth of July—holidays where people would be with their families and not focused on work.

“He tried to be polite about it, but there were days when his BlackBerry wasn’t firing, and I could see that it depressed him,” the former friend says. “Where is everybody?” he wondered. The answer: “They’re celebrating with their families. That’s what they’re doing.”

This former friend has not talked to Schmidt in years but was speaking with a mutual friend of theirs about six months ago. “The word that this guy chose was ‘rudderless,’” the former friend concludes. “That Eric seemed sort of rudderless right now. I know he’s the kind of person who needs to have something to do.” (A person close to Schmidt disputes the “rudderless” characterization and says that Schmidt is as busy and active as ever and “wishes he had left Google sooner.”)

William D. Cohan is a Writer at Large for AIR MAIL and the author of numerous books, most recently Four Friends: Promising Lives Cut Short