What it’s like to attend Silicon Valley’s ultimate swingers party, where VCs, startup employees, and engineers swap sex partners for the night

In her new memoir, “Special Characters: My Adventures with Tech’s Titans and Misfits,” Segall reflects on her years covering the likes of Uber’s Travis Kalanick and Facebook’s Mark Zuckerberg. She also gives the backstory behind some of her more memorable adventures.

The edited excerpt below focuses on Segall’s reporting for a CNN series titled “Sex, Drugs, & Silicon Valley.” As the tech world boomed, Segall discovered that a growing number of the Bay Area’s newly rich entrepreneurs and engineers were opening their marriages and exploring concepts like sex parties and polyamorous relationships through the lens of technology—applying the concept of “disruption” to their own personal lives. In chasing the story, Segall got a close-up look at a hidden side of Silicon Valley. 

When the cab dropped me off in front of a tidy little building in Oakland, it was hard to imagine that it housed a dominatrix dungeon. As I walked into the beige lobby, it occurred to me that there was nothing particularly notable, other than how quiet it was inside. I scanned the nondescript space for any traces of BDSM, but only found signs for the Woman’s Voters League. I went up the stairs and through a side door that led to a secret dungeon. 

A woman with long dark hair and jade eyes wearing an ankle-length black dress greeted me. It was Madame Rose.

“Welcome,” she said, smiling. She led me into the dungeon, full of contraptions, hanging sex swings, and a large cage in the corner. The wall held black leather masks, gas masks, long silver chains and leather restraints, and what she would later inform me was a device used for low-grade electric shocks. In an attempt to come off as professional and not prudish, I willed myself to act natural. 

“Take a seat.” 

I obeyed, looking around uncomfortably. I found myself propped against what I soon learned was a bench reserved for spanking.

“Everything in here is high-tech,” she explained, as I glanced at one of the gas masks that had iPod earbuds attached. “My tech clients helped me create much of this.”

She pointed to a large contraption above us. 

“That crane can hold up to 900 pounds. It was built by one of my engineer clients.” 

I looked up in awe. 

The wall held black leather masks, gas masks, long silver chains and leather restraints, and what the dominatrix would later inform me was a device used for low-grade electric shocks.

Then she led me over to the large iron cage in the corner. 

“Want to get in?” she asked, lifting an eyebrow.

“I’m good,” I said quickly, wondering how I’d explain getting locked in a sex dungeon. 

She gestured at the cage. “This jail cell here was constructed in perfect proportion to the jail cells in Alcatraz by an MIT engineer.”

“Will he go on camera to talk about it?” I asked.

“Definitely not.”

We paused for a moment as I studied the perfectly proportioned cage, gleaming against the red walls. I wondered whether any of the engineers I’d encountered at dozens of tech conferences had been inside of it. 

Madame Rose read my mind.

“Where do you think all the Apple engineers get their creative inspiration? I lock them up for the weekend.” 

We laughed. 

“These guys get off on it, they love being controlled,” she told me. “Why shouldn’t I be able to make money off the boom? I have a respectful relationship with my clients. We have rules, boundaries. No one gets hurt—without consent, of course.” She winked. “Want to see the nipple clamps?”

Increasingly, in 2013, Silicon Valley was the center of power. The deals, the money, the ego, the people here who were “changing the world”—it all happened in her backyard. A crane didn’t need to hold 900 pounds, but because it was built by one of her engineering clients, it could. And maybe that was the point of this. 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. 

“Oh, honey,” she said, crossing her legs. “If you only knew.” 

“Disrupting” the monogamous relationship

“What do you mean, there are sex parties, and everyone is polyamorous?” I asked the VC sitting across from me, who was also a former Twitter lieutenant. We were having dinner at a fancy restaurant in the Ferry Building.  

It was 2015 and disruption was the word in Silicon Valley. Over half a dozen oysters, I was learning that the concept was also being applied to the personal lives of the people coding our future. I knew there was an uptick in experimentation with micro-dosing and smart drugs for productivity, and now, it seemed, there was experimentation with relationships, too. A new app called “Secret,” built by a former Square engineer, allowed anyone to post anonymously on the app and “share secrets” with their friend group and acquaintances (a ticking time bomb in the Internet age). It was funded by major investors in Silicon Valley, and while it hadn’t quite become mainstream, the app was serving as a distracting source of Silicon Valley gossip. People were posting everything from VC inter-fighting to rumblings of swingers’ parties and startup acquisitions that had yet to take place. It was catnip for journalists, and after three postings referencing a particular sex party, I’d decided to do some digging. 

Eyes gleaming, the VC broke it down: “From what I understand, people fall into two camps: the swingers and the polyamorous.”

“From what you understand…or what you know?” I joked.

He laughed. “Listen, I know people in both camps. Everyone is experimenting.”

“Would they talk to me?”

“I’d love to see that,” he challenged. 

He went on to describe the philosophy and the principles. Polyamorous couples may have multiple romantic relationships. Sometimes, people have a primary partner and other arrangements, meaning both partners have relationships that are secondary; but the configurations vary. The swinger community, he went on, is less about relationships and emotions. Swinger couples go to events together, have a good time, and often have sex with different partners for the evening; but that’s where things end. 

I picked up another oyster. My partner Ethan and I had been dating long-distance for almost a year. I was happy with him, and relatively secure, and on a cerebral level, I understood that he or I could be attracted to different people at different times, even if we were in a committed relationship. But the idea of having multiple partners—could I relate to it? Sure. Could I do it? Hard no. If Ethan asked me to be polyamorous, I would throw him off a cliff. But I was curious about why other people found it so appealing. 

There was something interesting about the “don’t play by the rules” entrepreneur mentality when applied to relationships—even if polyamory and swinging weren’t exactly groundbreaking. I started reading about various alternative communities, and learned that in the 19^th century, in upstate New York, a minister named Jon Noyes conducted an experiment offering a way around traditional monogamous relationships, called “complex marriage.” Three hundred people lived in a commune, and all of them were considered to be married to each other. There was also plenty of material from the sixties, when non-monogamy was popularized in an era of “free love.”  But I was curious to see Silicon Valley’s take on it.                    

I pitched an idea for a long-form digital series about the “other side” of Silicon Valley to the newly anointed head of digital at CNN. 

“What do you think?” I asked, after he’d studied a pitch I’d typed up with descriptions of all the titillating stories we would cover as a part of the “special: polyamory, swingers, the rise of smart drugs and LSD… We’d titled it “Down in the Valley.” 

I saw his brow furrow. It had taken me weeks to get a meeting. Oh no. He hates it.  

“I like it. But let’s call it Sex, Drugs, & Silicon Valley,” he said. 

I nodded eagerly.

The following month, my producer, Erica, and I began to shoot “Sex, Drugs, & Silicon Valley.” Through a source, I learned that a major founder of a software company who’d sold his company for millions was polyamorous. I asked if he would meet me to chat about a story, and prepared for a graceful pivot to “Are you polyamorous?” We met at a popular spot in the Flatiron District. Walking into the noisy bar, I cursed myself for choosing a place with so many people around. This wasn’t the best location to ask a newly minted millionaire whether he had multiple partners, especially when he thought we were there to discuss software. 

“So, this is a bit awkward,” I began, “But I’m doing a special on different types of relationships in Silicon Valley. You know, people who are opening up more and living by a different set of rules.” Barely able to make eye contact, I took a sip of my gin and tonic and willed myself to keep speaking. “Do you have any knowledge of people experimenting with open relationships? Polyamory, perhaps?” 

His body language shifted perceptibly. We both knew what I knew. I waited for him to walk out, but instead we had an in-depth conversation about his polyamorous relationships. And then, a surprise victory: he offered to introduce me to his (second) girlfriend, who turned out to be lovely, charming, and ended up introducing us to her girlfriend, who appeared in our series. 

Monogamy or marriage wasn’t inherently flawed, but “it may not be the right product for everybody,” explained one prominent Silicon Valley technologist.

A month later, Erica and I traveled to San Francisco to begin shooting our series. On a beautiful day in San Francisco’s Dolores Park we set up our cameras for the interview. I sat across from a woman named Sydney, an engineer at a major tech company who had short blonde hair and a calm demeaner as she described her relationship status(es). Sydney was in four relationships. She’d been seeing a woman for two years. “We say ‘I love you’ to each other,” she said, smiling as we sat on the grass. She also saw a man once a month, and kept a slot open for what she called her “distraction spot” for anyone catching her attention. Her primary relationship was with her fiancé, who was a man. It sounded both intriguing and exhausting. 

“Polyamory is a form of optimization in the sense that you make trade-offs, and you take risks,” she explained. She was a woman speaking openly about alternative relationships, and an engineer speaking in tech lingo. “In technology, people have higher appetites for risk. Opening up your relationship is really risky in a similar way that starting a company is really risky.” 

A part of me understood the logic. But opening up your relationship was very different than building a startup to revolutionize laundry. Again, I thought of Ethan. I couldn’t stomach the idea. Perhaps I was a uniquely jealous creature, but I didn’t think I could ever be okay with sharing in the relationship department. 

“Love is irrational. Love is crazy. We do things we would never do when it comes to love,” I said to Sydney. “How can you be so analytical about it?”

“I feel completely irrationally in love with my fiancé.” She smiled, “I also have that irrational love with other people.”

Later that afternoon, I strolled down Pier 14 in San Francisco with Chris Messina, a blond engineer with dark-rimmed glasses and a thoughtful gaze. In a sense, Chris had invented part of internet culture, as he was the engineer responsible for Twitter’s use of the hashtag. He also described his own relationship status, at the time, as polyamorous. As we walked along the water, he echoed Sydney’s statement, describing his own non-monogamous relationship, and emphasizing that traditional relationships were ripe for disruption.

“If you’re trying to build a product—let’s say, to draw an analogy—and it’s failing 50% of the time, you might want to consider the design and think about ways of improving that,” he said. 

Monogamy or marriage wasn’t inherently flawed, he added, “but it may not be the right product for everybody.” Chris went on to explain that online communities were growing, in which people were talking about opening up their relationships. 

Francesca Tamse—The New York Times/Redux

If the Internet was enabling everyone’s weird to be a little less so, it was also amplifying everyone’s weird, thus opening up a new era of experimentation. As Chris and I walked by the Ferry building, I thought about dating apps beginning to take off and the fundamental behavior changes that were happening as a result. Tinder had launched two years before, and already had become a game-changer in the dating world; Bumble had followed suit a year ago. I’d found myself mindlessly swiping through options, and increasingly, at tech parties, people preferred to huddle in corners, shopping for dates online rather than put themselves out there in person.  Options that had once seemed finite were now infinite. 

I didn’t know what to make of it. Analytically, I could wrap my head around it, but a part of me wondered about a data-driven approach to something as personal and unstable as our own hearts.  

As I built up my contacts, I learned about a monthly party that a bunch of tech employees attended to “swing.” It was hosted by a guy named “Ralph,” a former tech entrepreneur who, more than a decade ago, had sold his first company for $5 million. If I could earn his trust, I had a better shot at pulling back the curtain on the Valley. I gave Ralph a call, and he told me that my best way into this world was to show up.

“What do you mean, show up?” I asked. 

“Come to a party,” he said matter-of-factly. “They’re very tasteful. I think you’ll enjoy it.” 

“And bring your boyfriend!” Ralph added enthusiastically. 

Over my dead body, I thought, and managed to squeak out a polite “Ha.”

Acting nonchalant amid the nudity

Weeks later, arriving at a nondescript building, I was greeted by Ralph—fat, bald, and sweaty. I’d learned that 4,000 people around Silicon Valley were on his mailing list. Many were startup employees, software engineers, and venture capitalists. 

Ralph pointed to an iPad where couples were checking in.

As the music blared, people stood awkwardly around a dancefloor illuminated by a green light. I had a polite conversation with a V.C. who wore khakis and a collared shirt. His girlfriend, who worked at Google, was in a sparkling crop top. Everything seemed kosher(ish). 

“I remember when we slept with another couple and high-fived after!” crowed a woman dressed in a Britney Spears-esque schoolgirl outfit. Her husband, a former Square employee, blushed. 

An hour later, feeling more at ease, I met Greg, a dark-haired engineer with prominent features who described his day job as one involving supercomputers, and Stella, an IT specialist, who had long curly hair, an easy-going demeaner, and a nice smile. The couple said they’d be happy to chat on-camera about their open, swinger relationships. Mission accomplished, I made my way to the exit. 

But as I headed for the door, the vibe started to shift. Clothing began to fall to the ground. The nice woman from Google had now taken off her top, revealing fabulous breasts. I did everything in my power to act nonchalant. She stopped me to ask if I was enjoying the evening.

“You have to check out the Magic Carpet Fuck Space!” he shouted over the music. 

Before I could protest, he was dragging me by the arm, up the stairs, to a scene I will never be able to un-see. A bin of towels sat next to a door that led to a room carpeted in mattresses draped in red sheets and framed with blue pillows. That’s where I saw him—well, the back of him. The same V.C. I had spoken to earlier was on his knees, naked, a giant multi-colored tattoo on his lower back, thrusting back and forth. 

“Well, that’s something,” I stuttered to Ralph. “I’ll be in touch!” I managed to say before fleeing down the stairs, and beelining to the door. When I got back to my Airbnb, I sat on the corner of the mattress, unable to erase the tattoo now etched into my brain. Was I a prude? I thought about the cheap mattresses and hungry looks, the Lysol on the staircase. The commoditization of sex made me feel like a virgin again.