It was the summer of 2013, and Laurie Segall, a 27-year-old tech correspondent for CNN, was given a tour of a sex dungeon designed specifically for techies in Silicon Valley.
Madame Rose, a dominatrix from Oakland, California, took Segall on a tour of the private club adorned with sex swings, leather cuffs, silver chains, and at least one device designed to administer low-level electric shocks.
But these contraptions, despite appearances, were not typical BDSM toys.
“Everything in here is high-tech,” Rose explained, as Segall recalls in her new memoir, Special Characters: My Adventures with Tech’s Titans and Misfits (Dey Street Books).
The gas masks, for example, came with Apple earbuds designed by one of their “tech customers.” A large iron cage was “constructed by an MIT engineer in perfect proportion to the Alcatraz prison cells,” Rose added.
Segall couldn’t help but wonder if any of the engineers she’d interviewed or met at various tech conferences had spent time in this cage. As if reading her mind, Rose said to her, “Where do you think all the Apple engineers get their creative inspiration from? I lock her up for the weekend.”
For Segall, who has covered the tech industry for CNN since 2008—back when young pioneers promising to change the world with apps were still largely ignored by mainstream media—meeting Madame Rose gave her a new perspective.
“Perhaps a part of me felt a certain joy as I imagined Silicon Valley’s cocky brethren being locked up,” Segall writes. The tech world was increasingly becoming one of “excess and opportunity, defying norms, power and control — I could feel it all hanging in the air alongside whips and chains. I’ve wondered out loud about the connection between power, control and sex.”
Madame Rose just laughed and crossed her legs. “Oh darling,” she said. “If you only knew.”
When Segall first joined the cable news giant — the Atlanta native moved to New York City via the University of Michigan — she hoped to make a name for herself by covering the same tech entrepreneurs “that I meet at pubs and tech meetups.” met,” she writes. “I wanted to write about the people that nobody else was paying attention to, that the world hadn’t noticed.”
She ended up landing exclusive interviews with many of the biggest innovators in technology before they became household names, from Mark Zuckerberg (Facebook) and Jack Dorsey (Twitter) to Kevin Systrom (Instagram) and Travis Kalanick (Uber).
She got access, not just because she was among the first to take it seriously — Segall regularly briefed CNN anchors on emerging technology trends and primed them with tips like, “Yes, ‘tweet’ is the right term” — but because she ran in the same circles, drinking and hanging out with the future tech titans and in some cases dating them.
The parties are her “secret weapon,” Segall writes, because “the gossip flowed as freely as the drinks.” At a fancy gathering overlooking Central Park, she overheard a drunken venture capitalist mutter, “Tweetdeck sold to Twitter for $40 million.” By drinking ’til dawn with the dealmakers themselves. She was often the first to report such deals.
But as she delved deeper into the tech revolution, Segall discovered that it wasn’t just about reinventing culture and bringing people closer together. Much of modern technology has revolved around sex and experimentation and the limits of what is considered healthy sexuality.
Or, as Madame Rose Segall asked, “Do you want to see the nipple clamps?”
In late 2013, the author traveled to San Francisco to write a story about sex workers who viewed themselves as Silicon Valley’s “other entrepreneurs” — a group from “the world’s oldest profession, taking advantage of the new money pouring into the newest profession the world flows,” she writes.
Kitty Stryker, a social media marketer by day and prostitute by night, told Segall that when a new Bay Area startup was doing particularly well, she would be regularly visited by her employees — many of whom weren’t shy about sharing how they got on their wealth.
“And then they might stall,” Stryker said, “and then you see a bunch of people from another startup.”
The escorts didn’t just take advantage of the influx of affluent clients — they went out of their way to target them.
Another woman told Segall that she made sure her prostitute stable “Game
of Thrones underwear” and lingerie adorned with phrases like “Winter is Coming” and “Geeks Make Better Lovers,” especially when promoting their services on sites like MyRedBook and Craigslist because it “appealed to nerds with green startup greenness.” ‘ she said to Segall.
Many sex workers used the inventions of their clientele.
Segall met a prostitute who regularly used Square, a mobile payment app developed by Twitter CEO Jack Dorsey, to receive more discreet compensation from her clients.
“That 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’m filing it under a different company name,” explained the unnamed prostitute Segall. “As far as Square knows, it’s a consulting firm.”
Not all intimacy in Silicon Valley was billed by the hour. In 2015, Segall learned about a new app called Secret, being developed by a former Square engineer, that allowed users to “share secrets” anonymously. 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 soon met people like Sydney, an engineer at a large tech company who was in four relationships: with two women, a man (her fiancé), and a vacancy for anyone who happened to catch her Attention.
Sydney explained how love can be “hacked, in the same way that traditional industries have been turned upside down by people who think outside the box,” Segall writes. “If entrepreneurs could hack transportation, ie Uber, why not hack the concept of traditional relationships?”
People in tech “have a higher risk appetite,” Sydney explained to justify their behavior. “Opening a relationship is really risky, much like starting a business is really risky.”
Segall also stumbled upon an active swinger community, with weekly sex parties that left little to the imagination. She managed to snag an invitation to “Silicon Valley’s first sex party” from Ralph, the alias of a former tech entrepreneur who sold his first company for $5 million.
“I had learned that 4,000 people from Silicon Valley were on his mailing list,” Segall writes. “Many were startup employees, software engineers and venture capitalists.”
Guests checked into the party with an iPad, using software Ralph boasted about
designed by “the same guy who built Oracle”.
Arriving at the party, she made small talk with couples she knew from her tech career—there was a woman who worked at Google and an engineer who built supercomputers—and discovered how easily they agreed to to talk about the swinging lifestyle.
“I remember we slept with another couple and high fives afterwards,” shared one woman in a Catholic schoolgirl outfit, while her husband, a Square employee, blushed.
At the top of the part was the “Magic Carpet Fk Space”, a room laid out with mattresses with red sheets and blue pillows.
“That’s where I saw him — well, from behind,” Segall writes. A venture capitalist with whom she had a heartfelt but unforgettable chat earlier in the evening was now “on his knees, naked, a huge colorful tattoo on his lower back, jerking back and forth.”
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