It was the summer of 2013, and Laurie Segall, a 27-year-old tech correspondent for CNN, was being given a tour of a sex dungeon designed specifically for Silicon Valley tech geeks.
Madame Rose, a dominatrix from Oakland, Calif., took Segall on a tour of the private club — adorned with sex swings, leather restraints, silver chains and at least one device designed to give low-grade electric shocks.
But these contraptions, despite appearances, weren’t typical BDSM toys.
“Everything in here is high-tech,” explained Rose, as Segall recalls in her new memoir, “Special Characters: My Adventures with Tech’s Titans and Misfits” (Dey Street Books).
The gas masks, for instance, came with Apple earbuds, designed by one of her “tech clients.” A large iron cage was “constructed in perfect proportion to the jail cells in Alcatraz by an MIT engineer,” Rose added.
Segall couldn’t help but wonder if any of the engineers she’d interviewed or met at various tech conferences had spent any time in that cage. As if reading her mind, Rose told her: “Where do you think all the Apple engineers get their creative inspiration? I lock them up for the weekend.”
For Segall, who’d been covering the tech industry for CNN since 2008 — back when scrappy young pioneers promising to change the world with apps were still widely ignored by mainstream media — the meeting with Madame Rose gave her a new perspective.
“Perhaps a part of me felt a certain delight, imagining the over-confident bros of Silicon Valley getting locked up,” Segall writes. The tech world was increasingly driven by “excess and possibility, defying norms, power and control — I could feel it all hanging in the air, alongside whips and chains. I wondered out loud about the connection between power, control and sex.”
Madame Rose just laughed and crossed her legs. “Oh, honey,” she said. “If you only knew.”
When Segall first joined the cable news giant — the Atlanta native moved to New York City by way of the University of Michigan — she hoped to make her mark by covering the same tech entrepreneurs “I was meeting in dive bars and tech meetups,” she writes. “I wanted to write about the people no one else was paying attention to, the ones the world had yet to notice.”
She ended up landing exclusive interviews with many of the biggest innovators in tech before they became household names, everyone from Mark Zuckerberg (Facebook) and Jack Dorsey (Twitter) to Kevin Systrom (Instagram) and Travis Kalanick (Uber).
She was given access not just because she was among the first to take them seriously — Segall was regularly briefing CNN anchors on emerging tech trends, prepping them with tips like, “Yes, ‘tweeting’ is the correct term” — but because she ran in their same circles, drinking and socializing with the future tech titans, and in some cases, dating them.
The parties were her “secret weapon,” Segall writes, because the “gossip flowed as freely as the drinks.” At one fancy gathering overlooking Central Park, she overheard a drunken venture capitalist mumbling, “Tweetdeck is selling to Twitter for $40 million.” By drinking till dawn with the dealmakers themselves. she often ended being the first to report on such deals.
But as she got deeper into the tech revolution, Segall discovered that it wasn’t all about reinventing culture and bringing people closer together. Much of modern tech was about sex and experimentation and pushing the boundaries of what’s considered healthy sexuality.
Or, as Madame Rose asked Segall: “Want to see the nipple clamps?”
In late 2013, the author traveled to San Francisco for a story about sex workers who considered themselves Silicon Valley’s “other entrepreneurs” — a group from “the world’s oldest profession taking advantage of the new money pouring into the world’s newest profession,” she writes.
Kitty Stryker, a social media marketer by day and prostitute by night, told Segall that when a new startup in the Bay Area was doing especially well, she’d be visited regularly by their employees — many of whom weren’t shy about sharing how they got their riches.
“And then they might falter,” Stryker said, “and then you’ll see a bunch of people from a different startup.”
The escorts weren’t just taking advantage of the influx of big spenders—they were going out of their way to target them.
Another madam told Segall that she made sure her stable of prostitutes wore “Game
of Thrones underwear” and lingerie adorned with phrases like “Winter is Coming” and “Geeks Make Better Lovers,” especially when advertising their services on sites like MyRedBook and Craigslist, because it “appealed to nerdy guys flush with startup green,” she told Segall.
Many sex workers took advantage of the inventions created by their clientele.
Segall met one prostitute who regularly used Square, a mobile payment app designed by Twitter CEO Jack Dorsey, for more discreet compensation from her johns.
“This probably wasn’t what Jack had in mind,” Segall thought, recalling a coffee-shop interview where Dorsey first told her about his ambitions for Square.
“I file it under a different business name,” the unnamed prostitute explained to Segall. “As far as Square knows, it’s a consulting business.”
Not all of the intimacy in Silicon Valley was being charged by the hour. In 2015, Segall learned of a new app called Secret, built by a former Square engineer, that let users anonymously “share secrets.” With a little snooping, Segall learned that many prominent Silicon Valley entrepreneurs were polyamorous — meaning, they had multiple romantic relationships with both men and women.
Thanks to friends who vouched for her, Segall was soon meeting people like Sydney, an engineer at a major tech company who was in four relationships : with two women, a man (her fiancé), and an open slot for anybody who happened to catch her attention.
Sydney explained how love could be “hacked” in the “same way traditional industries were upended by people who thought outside the lines,” writes Segall. “If entrepreneurs could hack transportation, i.e. Uber, why not hack the concept of traditional relationships?”
People in tech “have higher appetites for risk,” Sydney explained to justify her behavior. “Opening up your relationship is really risky in a similar way that starting a company is really risky.”
Segall also stumbled upon an active swingers’ community, with weekly sex parties where little was left to the imagination. She managed to secure an invite from Ralph, the pseudonym of a former tech entrepreneur who sold his first company for $5 million, to “Silicon Valley’s premier sex party.”
“I’d learned that 4,000 people around Silicon Valley were on his mailing list,” writes Segall. “Many were startup employees, software engineers and venture capitalists.”
Guests checked into the party with an iPad, using software that Ralph bragged was
designed by “the same guy who built Oracle.”
Upon arriving at the party, she made small talk with couples she recognized from their tech careers — there was a woman who worked at Google, and an engineer who built supercomputers — and discovered how easily they agreed to talk about the swinging lifestyle.
“I remember when we slept with another couple and high-fived after,” shared a woman dressed in a Catholic schoolgirl outfit, while her husband, an employee at Square, blushed.
Upstairs at the part was the “Magic Carpet F–k Space,” a room carpeted in mattresses with red sheets and blue pillows.
“That’s where I saw him — well, the back of him,” Segall writes. A venture capitalist she’d had a cordial but unmemorable conversation earlier in the evening was now “on his knees, naked, a giant multicolored tattoo on his lower back, thrusting back and forth.”