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Sex, Lies, and Video Games

Oomba was a startup designed to make a lot of money from the games industry — instead, everyone played each other

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When her new boss started hitting on her, Ronnie* wondered if she might be able to take advantage of the situation. She was 23, and by now she’d figured out that when she raised the pitch of her voice and dressed like an anime fantasy girl, switching her hair from purple to green to pink every few weeks, it drove certain guys wild. Guys like the CEO of this startup, a serial entrepreneur named Michael Williams. She examined him from her desk: he was 49 and seemed rich but painfully nerdy and obsessed with Magic: The Gathering. Maybe if she acted all bubbly and let him stare, she could get a raise or a promotion. His crush was her opportunity.      

“I could tell he just wanted to hang out with a cute girl,” she tells me.

It was the summer of 2016, and this was Ronnie’s first office gig. “I called it my big girl job,” she says. Once she saw the perks of working in tech, she didn’t want to go back to retail. After all, Claire’s had never encouraged its mall employees to play beer pong at happy hour. The startup, called Oomba, was even doing something cool: building software that could run tournaments for any game, from Scrabble to soccer to League of Legends. Ronnie liked video games, especially the art, and even a few trading card games, as long as they were fair and the rules stayed consistent. Yu-Gi-Oh, for example, she couldn’t stand. A few rare cards were too powerful, rigging the outcome. And where was the fun in that?  

“I think Mike was delusional, that he literally thought he was going to develop the next Facebook”

Ronnie’s family had fled Mexico for Southern California when she was nine, after a cartel threatened to kill them if her father didn’t move drugs or at least pay a bribe. In the US, her parents worked hard, but she could relax. “My thing was just kind of partying,” she says. “A total scene kid.” At 20, she moved in with a boyfriend who became more and more domineering, until one day it escalated into a physical fight between them, and she says he picked her up by the throat and threw her. She left him, but in retrospect, Ronnie says she thinks Williams noticed she was “a damaged girl” and therefore vulnerable — that this was why he came by her desk, remembered her birthday, asked for her phone number.

Two months after she started at Oomba, Williams invited her out after an office party. 

“Where are we all going?” she asked. 

“Shhh,” he said — he’d meant just the two of them, alone. 

“Okay… yeah, sure,” Ronnie agreed. She tried to be accommodating, she tells me later. “I wanted to be his favorite, so I could stay there the longest and move up.”

Williams took Ronnie to an arcade and filled a card with points for her to play. In the flashing neon, above the clangs and hoots and whistles, he mentioned he also liked to go to strip clubs. You like to spend money on girls, Ronnie thought, so maybe you could spend some money my way

Afterward, in his BMW, Williams confided that being CEO wasn’t as fun as it seemed. He spent most of his time pestering investors, he said, trying to bring in more capital with a desperation that left him feeling like “a money whore.”

Ronnie looked at him and realized this was her opening. She played her card. 

“I’m a money whore, too,” she told him. “I sell nudes online.”  

“No way!” he said and offered her $500. It was more than the $130 she’d been charging guys on Tumblr for her collection, and more than she made in a week at Oomba. They stopped at an ATM, and she emailed him a drive of explicit photos and videos. This felt like a game she’d been playing for years. It was almost too easy. 

“From that point forward, I basically became his sugar baby,” she tells me. “He even said he loved me, and I kind of feel that he did. But not in a healthy way — in a controlling, manipulative kind of way.” She’d thought that Williams would be “just another john,” that Oomba would be an easy win, but the rules kept changing and catching her by surprise. One move led to another, and soon everything got out of hand. 

By the summer of 2018, 18 months after Williams took Ronnie to the arcade, Oomba would be over, with Williams facing internal accusations of financial mismanagement and inappropriate sexual relationships. But first, after squeezing the same investors for years, and though Oomba had zero revenue, it seems the company raised about $35 million from Chicago firm ExWorks Capital and blew through all of it in about a year. Where did the money go? No one is quite sure. There was a seven-figure splurge on a Las Vegas extravaganza featuring Big Bang Theory star Wil Wheaton that was so over budget the company didn’t fully pay the venue, according to a former member of management. There were chic offices, where Williams fell hundreds of thousands of dollars behind in rent. And there were a whole lot of sex workers. 

I reviewed thousands of pages of documents and spoke with over 30 sources about Williams and Oomba, including investors, employees, and business partners. Most described him as narcissistic, a fast-talking salesman with a talent for separating people from their savings. He drank a lot of Red Bull and had a puerile sense of humor, asking an employee who brought her cat into work, “Can I pet your pussy?” again and again. Williams apparently didn’t like rules, couldn’t focus, and seemed unable to accept that he might ever be wrong. He could be volatile, swearing over text message (“if you don’t return my call by 5 PM you are fucking fired you fucking douche”) and chastising employees over the office PA system (“Come to my office now you dumb motherfucker”). 

And he often stretched the truth, especially when doing so enabled access to more funding or let him out of paying for something. 

“It was my feeling that he cheated investors, he cheated employees, and he cheated vendors, and he felt zero guilt about that, I mean zero,” said one C-level executive who worked at Oomba for almost three years.  

(Williams refused repeated requests to speak with me, saying over text, “I hope you get all your facts straight and that you’ll spell my name correctly.”) 

In some ways, the rise and fall of Oomba is so outlandish that it competes with the worst startup horror stories. Williams was allegedly dating three employees at a time. He raised over $250,000 on Kickstarter and never followed through on the project for which the money was meant. He pledged $400,000 in college sponsorships and only gave a quarter of it. He claimed that magician Penn Jillette and Atari founder Nolan Bushnell had invested in Oomba, something both men deny — though Bushnell is a friend who held a formal role at one of Williams’ previous startups, which was called, almost unfathomably, Reality Gap. 

“NBA stars were going to get involved, and Kobe Bryant would put in a million,” one Oomba investor recalls. “I think Mike was delusional, that he literally thought he was going to develop the next Facebook, but at some point, when he realized he wasn’t, he started lying.” 

Bushnell, who has his own history of alleged inappropriate sexual behavior, is more forgiving. He describes Williams as “probably the most optimistic guy I’ve ever met,” and says he has no hard feelings about being falsely named in press releases as Oomba’s chief visionary officer, adding, “A lot of times, the difference between an optimist and a scoundrel is nuance.” 

“He was wearing a suit two sizes too big and had a hole in the bottom of his shoe”

Paychecks came late, if at all. Invoices went unpaid. A $100,000 loan agreement was scanned and emailed without signatures, giving Williams cover to deny the loan had happened at all. And after four years, the company’s core product was never able to do what it said it was supposed to: work with any game. It’s possible this was because many of Oomba’s engineers were college students whom Williams apparently sometimes paid in free food and the promise of stock options. Or maybe, a few employees suggest, he preferred to keep the software unfinished. 

“There’s glitches and glitches and glitches, but he didn’t want it to work. He wanted it to stay almost done, to raise more money from investors,” one senior-level employee believes. “I told people really early, ‘Listen, this is what it is. Just shut up and get paid while we’re getting paid.’”

This was a common attitude at Oomba: grab the money hose and hold on before it all ran out. It’s almost hard to blame them. Why not try to catch some of that $35 million as it fell? I’ve done the same myself with other startups. Maybe you have, too. There’s little order or fairness in what gets funded and, of course, no justice whatsoever in who has the wealth to invest in a startup to begin with. Capitalism is capricious.

But how did Oomba manage to raise so much in the first place? Well, versatile tournament software is apparently a good idea and something that still hasn’t quite been done. When the company was founded in 2013, game-adjacent investments were prescient — before Twitch, the streaming platform, and Discord, the messaging service, got big. Competitive video game play, or esports, was taking off as a spectator sport in Asia. And of course, Williams is a white man who was trying to raise capital in the era of peak startup, a six-year period when the total amount invested by venture capital firms more than tripled: from $41.3 billion in 2012 to $140.2 billion in 2018. 

So the story of Oomba is also the story of the average startup: most fail. At least half go out of business within four years. That’s usually the point for people who fund early-stage software companies: riskier investments in the hopes that a few will pan out spectacularly. And with great risk comes the occasional Oomba. 

Michael Williams started raising money for Oomba in 2012 and 2013. By his side was a blond actress, Dylan Hundley, who starred in the Oscar-nominated 1990 film Metropolitan. The unlikely duo found an audience on the East Coast when a finance guy saw the pitch deck and brought it to his golf club buddies in Connecticut. 

“He presented it as, ‘I get pitched all the time, over a long career, and this is one of the best concepts I’ve been presented with,’” explains one friend. The finance guy said Oomba was a hundred-bagger, or maybe a thousand-bagger, meaning they’d get back a thousand times their investment. To seal the deal, Williams and Hundley came to the golf club — a lush expanse dotted with white birch and sycamores — for cocktails, hors d’oeuvres, and a Powerpoint in a private room. 

“There was a lot of enthusiasm, and everyone fed off each other,” one golf club member tells me. Williams didn’t quite impress — “He was wearing a suit two sizes too big and had a hole in the bottom of his shoe,” — but Hundley made up for it: “She was a very attractive woman, and she had been in the movies.” 

A few years earlier, Hundley had done some consulting for Williams when he was CEO at Reality Gap. Having already spent $7 million in investor funding, he paid her using money meant for payroll taxes; as a result, the board fired him. Now here she was, helping him secure new backers.  

One of the investors, Paul Rotondo, agreed the golfers were smitten with Hundley and therefore with Oomba: “The fellas at the club, they’re kind of all hornbags,” he says. “Your eyes glaze over. It’s a big frickin’ dream, you find something like this.” 

Around 20 members of the golf club invested. Several brought in family and other friends. The finance guy got his ex-wife involved. Some people didn’t have the savings necessary to be accredited investors, but Williams helped “fudge” the paperwork, as one person put it. On an early shareholders’ call, Williams announced Oomba had “tens of thousands of users,” though the real number of accounts was more like 450. Expectations were high. 

Rotondo says one golf buddy “was of the opinion that our group could buy some kind of airplane that we could share” when Oomba hit it big. “He had this money spent.” 

Meanwhile, in California, a college sophomore named Tyler Hogan met Williams at a midnight Magic: The Gathering tournament during the fall of 2013. When Williams saw his University of California, Irvine sweatshirt and learned Hogan was studying computer science, he offered him an internship on the spot. Hogan is pale and towheaded, with soft features and trusting blue eyes. He was intrigued. “What’s the worst that could happen? I’m just getting experience,” he said. That spring, Hogan brought Williams to his video game development club at UCI. At least four additional students got hired. For a while, this was Oomba’s entire engineering team. 

The college kids came in on evenings and weekends, even pulling all-nighters at the office. But Williams seemed determined to distract them. He insisted on adding streaming, stretching resources to form OombaTV. He set up promotional tournaments before the software was ready, announcing after one that over 200,000 people had watched — Google Analytics only showed 1,995 viewers. 

“It was always like, ‘Oh, quickly add this one fix in to make the tournament work for this weekend!’” Hogan says. “We were never taking the time to think through how this would work for hundreds of thousands of people at the same time.”

As simple as digital brackets may sound, not all tournaments look like March Madness. Complications arise around scoring, teams, and elimination. But Oomba apparently ignored the tech dictum to design at scale. The company spent years writing code tailored to whatever kind of tournament it would be running next, without ever achieving a universal solution that could be customized.  

“I never did quite understand what he was trying to do, other than trying to make money off the investors” 

The limits of this strategy became clear by August 2014 when Oomba debuted at Gen Con, the annual 60,000-person gathering focused on “tabletop games,” meaning roleplaying games (like Dungeons and Dragons), collectable card games (like Pokémon), and board games (like Clue). These are the games that Williams loves, but they were not the priority of investors. Tabletop has grown in the past decade — driven by megahits like Cards Against Humanity and Catan — and in 2018, the category brought in $11.95 billion worldwide. But that same year, video games made over ten times more: $138.7 billion. 

At Gen Con 2014, Oomba was supposed to run a Catan tournament and a Guinness World Record-setting tournament of rock, paper, scissors. It was chaos. 

“Everybody was just at the edge of their wits, super stressed, not getting enough sleep,” Hogan recalls. “The software was like half running it, but it was kind of falling over in a lot of places.”

By the end, Oomba was banned from exhibiting at the convention in the future.

Larry Roznai, who was in charge of Catan as the president of Mayfair Games, says that in spite of months of promises, Oomba’s software couldn’t handle a Catan tournament. “At the end of the day, there was nothing functional behind it,” he tells me, adding that Mayfair never paid Williams a cent. “I never did quite understand what he was trying to do, other than trying to make money off the investors.” 

After Gen Con, Williams decided he wanted a place where Oomba could host tournaments, and he chose two storefronts — one for tabletop and one for video games — in the Laguna Hills Mall, a cursed-feeling place that was set to close in a few years. Rent was cheap. Foot traffic was low. 

One afternoon, the team returned to the office to find someone changing the locks. So Oomba’s employees relocated everything to a cinder-brick storage space at the mall. 

For about a year, this was Oomba’s home base. In the winter, it got so cold that Hogan wore his furry snowboarding jacket and kept a space heater under his desk. The demand from heaters and computers sometimes overloaded the circuits, cutting power to the room and sending everyone home. Many of the employees quit. Those who stayed were mostly in college and didn’t need the money — seeing as paychecks rarely came. “It would be like, ‘Hey, it’s Friday, let’s go to Buffalo Wild Wings!’, and we’d know intuitively that means we’re not getting a paycheck today,” Hogan says. 

On the other side of the cinder bricks, Yelp reviewers complained the esports-oriented Oomba Lounge was disorganized, with rude staff and computers that often broke. “Do NOT take your kids here,” wrote Rainbow K. in July 2015. “They only want to take your money.” 

Williams emailed investors that fall, asking for more funding and saying deals with Hasbro, Rock Band, and the South By Southwest festival were in the works. “We are talking about a global RISKⓇ tournament! 12 year-old Mike is loving this!!” he wrote. 

But as the months wore on, the folks in Connecticut grew antsy. Williams and Hundley, who was living in New York, kept calling the golf club members looking for more money each quarter: $20,000 here, $23,000 there. “He knew the people who invested a lot, we were the ones with the most liability, so we would invest more,” one golf club member tells me. 

With all this financing, Williams didn’t seem to care about revenue, let alone profit. “He truly does not have any idea at all about the value of the dollar,” claims one person who has worked with Williams on and off. “He spends money whether he has it or not.” 

Williams called her his “unicorn”

So in early 2016, Williams started looking into buying a chain of restaurant-arcades called GameWorks. GameWorks began in the late ‘90s as a joint venture between DreamWorks, Sega, and Universal Studios, with input from Steven Spielberg. Much had changed since then, including a few bankruptcies and restructurings. At his first meeting with GameWorks’ chairman Howard Brand, over lunch at a Chinese restaurant in Manhattan Beach, Williams wore a black-and-white striped referee’s jacket. 

“I thought he was a little eccentric. Typically when I go to these meetings I’m dressed pretty nice,” Brand says. “From my point of view, I didn’t really care, as long as he paid the price.” 

Howard Brand looks like George Costanza from Seinfeld but has serious business acumen — the kind of guy who flips companies in trucking, health care, and scrap metal recycling. He led the purchase of GameWorks from Sega in 2011 and began learning the complexities of the family entertainment center space. “There’s so many parts to it that you have to know: gaming, party, food and beverage,” Brand explains.

His son, an enterprising gamer named Michael, was finishing college and convinced his father that GameWorks should get in early on esports. Howard was skeptical but allowed the younger Brand to build out dedicated esports lounges in three of GameWorks’ eight locations, where he began hosting video game tournaments that attracted several hundred players and spectators. 

“People would line up in the heat to come in. It was amazing. I didn’t realize how big it was,” Howard says with pride. 

But even though GameWorks had advanced gaming PCs, the tournaments were run on spreadsheets.

This was where Oomba would come in. “If you have software to automate the process, it would improve the experience for the average gamer,” Michael Brand says. Williams put in an offer to buy GameWorks, and he and Howard negotiated a deal. But Williams didn’t deliver the money. 

“We gave Mike Williams four or five months,” Howard says, and he couldn’t come up with anything more than a few nonrefundable deposits. 

“My mentality was, it’s not going to happen,” Michael Brand says. You can’t pay for a company with enthusiasm. Silly costumes aside, if Williams was the kind of guy who had no follow-through, then that wasn’t going to change, no matter how many extensions he got. 

By the time Ronnie started at Oomba, in the late summer of 2016, the company had around two dozen employees spread across a two-story building in a low-slung office park with glass-walled conference rooms, a kitchen, and even a shower. Williams spent thousands on height-adjustable desks but sometimes didn’t pay the company’s health insurance bill; an employee once called a doctor’s office to schedule an appointment only to discover the policy was inactive. 

“I got my first paycheck when I was supposed to get my second, and I got my second when I was supposed to get my third, and from then on after every paycheck was over a month late, so after eight months, I couldn’t financially do it,” one employee tells me. 

People would quit all the time, and new people would get brought in. One executive left after having multiple vertigo spells, including one in the fast lane on the freeway, that he says were from the stress of working at Oomba. Multiple women left after they alleged Williams said something inappropriate or asked them out. 

“He tried to test the water like that with me, being friendly, and I was never receiving of it,” one woman says. “I put up my wall. And then once I did that, he started treating me a little bit differently” — less friendly, more making fun of her. 

But Ronnie was different: eager for cash and comfortable selling access to her body. Williams called her his “unicorn.” Barely a week after she first sent him photos, Williams took her to Las Vegas and bought Ronnie $2,000 worth of lingerie at La Perla.

“And afterwards, as a payment, he’s like, what are you going to do? So I masturbated in front of him,” she says. “He even got me my own room, and it was the nicest room that I’ve ever seen, at the Greek-themed hotel.” 

“I was like, I have a pretty sweet situation here. Why would I want to fuck it up?”

Caesars Palace was interested in partnering with Oomba on turning some of the property’s bars into esports lounges. “Caesars is the leader in live entertainment, but MGM owns sports, so if esports was going to become a battleground on The Strip, we wanted to throw our hat in the ring,” explains a former member of Caesars management. (Caesars Entertainment declined to comment.)

While Williams was in meetings, Ronnie posted about their Vegas getaway on Facebook, where she was friends with a few people in the office. When they got back, the HR manager called Ronnie in.

“Nothing weird ever happened,” Ronnie told her. She didn’t want to lose the job, she tells me. “I was like, I have a pretty sweet situation here. Why would I want to fuck it up?”

She and Williams settled into a routine: dates twice a month for $500 each, shopping sprees, and trips to the Taboo Gentlemen’s Club, about a 15-minute drive from Disneyland. Inside, women slowly got naked on a red-lit stage while Williams and Ronnie watched from leopard-print banquettes. 

“He would give me money to throw on cute girls dancing,” Ronnie says. “Girls would see him with me and therefore that would make them comfortable, and I would even say, ‘He’s so rich! He paid for my shoes.’”

Ronnie soon learned that Williams already had multiple sugar babies, many of whom worked at strip clubs. Dates were prearranged to avoid scheduling conflicts. “All these girls saw me as a threat,” she explains. “The more money he gave me, the less for them.” But because Ronnie refused to actually touch Williams, she was happy to let other women be more hands-on. She herself was still seeing other guys. Ronnie’s lack of interest in having sex with him seemed to only make Williams like her more, just as the investors in Connecticut continued to send Williams check after check, with a desire for success that only deepened as the goal appeared increasingly out of reach.  

“Whatever he promises you, ignore him”

In mid-December, Williams went to New York to raise more money, and he brought along Ronnie, who had never been to the East Coast. “I was so excited,” she says. “We stayed right on the square” — that is, Times Square. Her parents, believing she’d be participating in important work, were delighted. Instead, after his meetings, Williams, Ronnie, and Hundley, the actress, headed to the upscale clothing store Reformation where Williams spent thousands of dollars on clothes. Ronnie and Williams then went alone to a second Reformation across Manhattan to get a certain top that wasn’t available in the first one. There, he bought her even more: a red long-sleeved dress, a printed pantsuit, a pleated skirt, vegan shoes — about 15 items total. Next, the pair headed to a comic book store and a Japanese market for more gifts: fluffy gray sock-slippers, a sweater dress, volumes 1-3 of a Rick and Morty comic. 

The trip culminated, of course, in a visit to a strip club.

“I got super fucking wasted,” Ronnie says. “He wanted to go to a back room, and to get a back room, you need to spend money and pay for champagne.” She and Williams each picked out a dancer they liked and headed for a private room, where Ronnie soon asked the women if they would mind if she got in her underwear as well. They told her to go for it. “I remember being like, ‘I’m really drunk, I need to pee,’ and they let me use the girls’ bathroom, the working girls’ bathroom.” She saw a sign that said something like, “Whatever he promises you, ignore him,” and laughed. She approached the sink and the mirror. “I washed my hands and I look at myself like, ‘Wow, I’m really fucked up.’” She stumbled back to the room and had a little more to drink. Feeling woozy, she announced she was going to lie down and take a nap.

When she woke up, her bra was off. 

She was disoriented because she didn’t remember removing it. “Did I take it off?” she says. Up until this moment, Ronnie had been having fun, amassing free clothes and drinks and new experiences, but now she felt overwhelmed. She turned to find Williams, across the room with both strippers on top of him, making out with one and then the other. “I was like, ‘I need water.’” Ronnie felt like she could no longer tell if she was playing Williams or if Williams was playing her.  

She doesn’t remember how she got back to the hotel. The next day, Williams told her he’d carried her to her room from the taxi. 

As her job at Oomba grew more ambiguous, Ronnie tried to hold her boundaries while still appearing keen to please. She’d welcome office guests with a chipper hospitality, offering coffee or tea. One potential business partner laughed at Williams’ leering joke about her talent for “teabagging,” and later, at an airport bar on the way back to Vegas, he asked for her number. On the plane, she says, Williams asked if she would have sex with the businessman to secure the deal. “He was literally trying to see if he could send me to the hotel room to make the contract go through,” she says. The guy was married, and the whole thing was “gross.” Ronnie said no.

When they got to Vegas, Williams invited her into the room he was sharing with another sugar baby. Later, she heard him telling someone that they’d had a threesome, and she became annoyed. “I’m like, bro, that was not a threesome. That was just me awkwardly masturbating while you’re getting your dick blown.”

Still, over time, she found herself doing more than she’d thought she would. When she first met one of Williams’ favorite strippers, he tried to get them to make out with each other in a back room; when Ronnie didn’t want to, “they kicked me out.” Six weeks later, when she met a different stripper, Williams got a hotel room and Ronnie let the other woman penetrate her with a sex toy. 

At work, their relationship was an open secret, but rather than prompting shame, Ronnie’s proximity to Williams gave her influence. She reveled in her newfound power: “If somebody did something I didn’t like, I would tell him, and he would go off.” She says at least two people got fired because of her. Colleagues would ask advice on how to approach Williams or for help getting paid. If it was someone she liked, Ronnie was happy to help. “I’d be like, ‘So-and-so needs money. They’re really behind on rent. Can you just cut them a check?’ And he would.” 

Williams told Ronnie she should drop out of her part-time associate degree program because if she stayed at Oomba, she could rise through the ranks. He effectively promoted her to executive assistant and showed explicit shots of her on his phone to at least one senior-level employee. 

“I was just like, ‘Yeah, I’m the center of attention, and this is great, because I’m getting paid for it,’” she says. “I felt like a badass.”

“It was very clear how lost she was”

In January 2017, she moved in with him. Not long after, a woman that Williams often described as a stripper was performing at a warehouse rave. Ronnie and Williams went and took LSD. At one point, she told him she’d be back in ten minutes, but she got lost in the music and disappeared for two hours. He was upset. On the way home, sitting in the backseat of his BMW while a friend of hers drove, Williams reached over to hold Ronnie’s hand. She felt repulsed, but she worried about rejecting him: “He’s on acid, and who knows what he’s going to do, so I smiled and pretended I was okay with it.”  

Soon, Williams decided to hire the stripper who had performed at the rave, a white woman with dyed red hair and a penchant for headdresses, to appear on OombaTV. He spent $700 on a backdrop and paid her $500 a week to come in for a few hours, leaving other employees baffled. “No nerds are going to watch a girl pretend to DJ in gamer costumes and jump around,” one employee texted another. 

Ronnie didn’t mind seeing the redheaded stripper every so often at work. But then Williams decided to hire another stripper full time, a woman with a punk-rock look named Jenna*. He gave Jenna a title and a position well above Ronnie’s: chief of staff. “I couldn’t handle her being there and whispering in my ear, and then him whispering in my ear,” Ronnie says. Other people at Oomba were also stressed by Jenna’s presence. (Jenna did not respond to repeated requests for comment.)

“It was very clear how lost she was,” Hogan remembers. “It just kind of felt like she didn’t do anything.” After one employee noticed Jenna was using the office shower, she texted two co-workers, including the HR manager, who responded, “Does she fucking live there after hours?” 

Jenna was more confrontational with Williams, Ronnie says, trying to convince him to go to therapy. The pair once got into a fight at the office and stormed outside, right when a meeting was supposed to start. For half an hour, everyone else in the meeting sat in a conference room overlooking the parking lot, waiting and watching Williams and Jenna yell at each other.

“They were like, ‘Oh, okay, sorry, sorry, let’s go to the strip club.’”

At home, Ronnie started to feel the strain of what she’d taken on. She let Williams go down on her, and then wished she hadn’t. She was doing his laundry and cleaning up after him, but when other sugar babies came by, she didn’t like that Williams treated her like the help. She was supposed to be special, his unicorn, better than the other women. Things were getting serious with another guy she was seeing, and Williams asked, to her disgust, if he could watch them having sex. Finally, one afternoon, Williams and the redheaded stripper tried to surprise her in the building’s garage. They approached dressed as cops: him in a hat and aviator sunglasses and her in a sexy two-piece police costume with high boots. Before Ronnie understood what was happening, Williams turned her around and the redheaded stripper started to handcuff her. 

“I felt one cuff close in, and you hear that cshh noise, and I just started freaking out,” Ronnie says. She felt that this was a clear violation of boundaries: a sexual scene she had never agreed to, with restraints that put her at their mercy. “I was like almost crying, but I didn’t want to seem like the pussy in the situation.” When Williams and the redheaded stripper saw her panic, they gave up. But Ronnie was shaken. “Afterwards, I was like, ‘You really don’t give a shit about me.’ They were like, ‘Oh, okay, sorry, sorry, let’s go to the strip club.’” 

By the end of February, she decided to move out and told the HR manager, who texted two other employees about it. “That’s a tough decision, because he pays her bills,” one responded. “He’s so disrespectful, he humiliated her,” the HR manager wrote back. “She’s young and got manipulated by him. Now she’s realizing it.” 

Ronnie brought her mother and her boyfriend to tell Williams she was leaving and to convince him to take her off the lease. “He said her mom wouldn’t even speak to him,” the HR manager later texted an employee. “He said they canceled date night and he stop [sic] giving her money and she’s probably upset by that.” Williams was disappointed but maintained he didn’t want Ronnie to leave Oomba. 

Within a week, he changed his mind. 

“Now that she’s over him he wants me to drop the hammer 🔨 on her. I can’t do that. That’s a fucking lawsuit waiting to happen,” the HR manager texted an employee. “I want her to leave on her own. This way it’s not on us.”  

At the end of March, Ronnie found another job. In April, Williams hired a new receptionist, a young woman in her early 20s who liked corgis, açai bowls, and One Direction. She had yet to graduate from college. 

Other than gossiping about the CEO’s sugar babies, Oomba’s employees spent 2017 preparing for an epic undertaking called the Unrivaled tournament series: a $4 million attempt to bring the fanfare and showmanship of pro-wrestling to tabletop games, with over $250,000 in prizes. OombaTV planned to stream regional Unrivaled tournaments from about a dozen cities across the country for six games — including Munchkin, Ascension, and Epic Spell Wars II: Rumble at Castle Tentakill — all leading to a grand finale at Bally’s Las Vegas Hotel and Casino, owned by Caesars Entertainment. 

“He did that I’m sure thinking, ‘Hey, I’m going to drop all this cash, of course they’re going to give me their esports business,’ but they were two totally different divisions,” recalls Matt Scott, who was then Oomba’s CTO. And in spite of Williams’ many trips to Vegas, now with Jenna and the new receptionist in tow, Caesars was not impressed. At one point, when he flew in without an improved demo, a key executive wouldn’t make time to meet with him. 

“He sat in the waiting room to see someone senior at Caesars, for hours on end, who would never see him. But he threw a tantrum, essentially, like, ‘I’m not leaving,’” says the former Caesars manager. 

The Connecticut investors were desperate for the Caesars deal to work out — or for any deal to work out, really. By now, Oomba was in settlement negotiations with a different group of over a dozen early investors who were accusing Williams of securities fraud, breach of contract, and solicitation, having allegedly asked two women in the group to bring in new investors by having sex with them. Many of Oomba’s remaining investors were looking for an exit strategy. 

One opportunity seemed to be a complex arrangement called a special purpose acquisition corporation, or a SPAC, put together by the investment arm of a financial services company. The SPAC would allow Oomba to go public without the hassle of an IPO. But first, the company needed to survive an audit. 

“As far as I could tell, the books were all over the place,” one senior-level employee says.

“Time out: ‘Pokémon’!”

As the audit went awry, and Williams realized going public meant giving up equity and therefore control, he searched for an alternative. He found it in ExWorks Capital, a Chicago firm that specializes in financing businesses with high-interest loans. Somehow, Williams convinced the fund to give him over $20 million — including over $17 million to acquire the arcade chain, GameWorks. (The similarity between the names GameWorks and ExWorks was just a coincidence.) 

After a year of Williams blowing deadlines, GameWorks chairman Howard Brand was thrilled. “We got a six and a half X return on capital, so my partners and I made a lot of money on this,” he says. But as GameWorks began to merge with Oomba, in the summer of 2017, the chain’s leadership started to see how Williams ran his company. 

Once, during a presentation, Williams got an alert on his watch and announced, “Time out: Pokémon!” He walked out and grabbed the new receptionist, so the two of them could hunt monsters in the augmented reality game Pokémon Go. Another time, someone from GameWorks saw Williams and the new receptionist leave the office together, holding hands. 

“Never having been closely connected to Silicon Valley companies or something like this, I recognize that culturally, there are some differences out there,” says former GameWorks CEO Greg Stevens, who has worked in the family entertainment business for 21 years. “It’s nothing I would have allowed in my organization.”

By July, Oomba was receiving $850,000 a month from ExWorks, giving Williams more confidence. “He got too big for his boots,” one board member tells me. At a meeting with Red Bull, he asked them to fill his BMW with cans of the energy drink. He used money designated for payroll to buy two Mercedes Benz Sprinter vans, supposedly for the OombaTV team to drive to regional Unrivaled tournaments. He bungled an opportunity to work with the company behind his beloved Magic: The Gathering after asking for many times more in licensing fees than Scott, the CTO, thought was appropriate. 

By the end of the summer, at long last, Oomba managed to demo its software for Caesars. Williams had actually followed through. He left the room before the meeting was over and emailed asking for significantly more money than what had been agreed upon. That evening, Williams and Scott were supposed to have dinner at a tavern with a senior figure at Caesars. “When he gets to the table, he just looks at Mike and starts railing on him,” Scott recalls. “I’d never seen someone turn purple.” 

“You finally deliver something we like, and then the deal terms are completely different?” the man yelled. He left the restaurant without sitting down. 

Eventually, Williams sent threatening emails to Caesars management, and the people who had been working on the deal were told to never speak with him again. 

As the Unrivaled tournament approached, its budget swelled. Fewer game stores than expected participated in regionals, and few people showed up to play. No one was buying tickets to the Vegas finale. Williams grew frustrated, and when he saw that Hundley, the actress, made a mistake on the event’s landing page, he called and berated her for several days in a row. To lock in an audience, he decided to cover airfare for over 800 players and staff and hotel rooms for over a thousand. One employee said Williams even commissioned a company to pay hundreds of additional people to attend.

Then, a few weeks before the Vegas event, something unusual happened. Scott was told that Williams had invited a female employee to his hotel room while they were traveling for work; when she refused, he apparently told her he’d find a way to fire her. This wasn’t the weird part; Williams had been openly behaving this way around female employees for years. But this time, Scott told the HR manager at GameWorks — who actually investigated the complaint. 

Soon, internal investigations revealed that Williams had “sugar daddy” relationships with several employees, including Jenna and the new receptionist. He’d recruited assistants through the sugar daddy website SeekingArrangement, where he called himself SharpCEO and claimed he was worth $50 million. He’d put company money toward buying a car for his brother and motorcycles for himself and another employee. And Williams had transferred around $200,000 out of the company’s bank account to use as he pleased. 

“Mike was handling the cash himself, even though there was a CFO,” says one executive from this era. “He was using it as his personal checkbook.” 

One employee rushed to leave her grandfather’s funeral in San Francisco, so as to keep her job

Even before the HR investigation was complete, a handful of C-suite executives and a board member got together at a coffee shop to figure out what to do. It didn’t take long to decide Williams needed to be fired. “We felt we had no choice but to do so, under California law, and also simply being human,” one board member says. From New York, Hundley urged them on, apparently feeling betrayed after Williams’ outsized response to her website error. 

The plan was to confront Williams on a Wednesday evening, after everyone had gone home. A corporate attorney would review the charges on speakerphone. One board member was present in person, and the other would call in from the East Coast; the two men had already signed a letter to Bank of America removing Williams from the accounts, effective at 5PM. A locksmith would change the keys and the security code. A security guard was even waiting to escort Williams off the premises because a few people had heard Williams boast about having a gun in his office. 

The meeting started off okay. “Mike was confused. We caught him off guard,” Scott recalls. For much of the conversation, he was almost in denial. After a while, Williams begged the group to at least allow him to do the Unrivaled finale in Vegas, which was ten days away. But the board voted and removed him from his position. Then, he grew calm. 

“Well, this is all going to work out fine. I’m going to turn the tables,” Williams said. “You guys can’t fire me.”

He left, promising this wasn’t the end. 

“And here,” explains Scott, “is where he really revealed his sideways genius.” 

The next day, Oomba’s employees were disturbed to find an armed security guard at the office entrance. The executives ushered everyone into the conference room and announced that Williams had been voted out. Hundley was on speakerphone, saying, “You guys are safe now.” 

“This whole Unrivaled nonsense is going to stop,” one executive told the room. “We’re going to cancel it, salvage our losses, and not rack up any more bills.” 

Oomba’s employees stared back at him. Most had spent the past year working on Unrivaled. As they surmised, many were about to be fired. 

One of those immediately laid off was Jenna, whom the executives didn’t think had been contributing anything. But as it turned out, Jenna had administrative access to the company’s servers. And ostensibly at Williams’ direction, she soon locked out Scott and the people who’d fired her and restored access to Williams, who began reading everyone’s emails. 

That Saturday, Williams and Jenna came back to the office, and once again, called a professional to change the locks. Williams emailed many employees to fire them, and then contacted a smaller group that he saw as loyal, asking them to meet up that weekend. One employee rushed to leave her grandfather’s funeral in San Francisco, so as to keep her job.

In the middle of all this, Scott called the police and came down to the office. Williams “poked his head out, waved around some paperwork, and showed the cop this founder’s document, which said he was legally entitled to appoint new board members,” Scott says. “And there wasn’t a lot we could do.” 

As it turned out, Williams, not the people who had initiated the coup, was in charge.  

“No one had really looked at the agreements,” one executive says. “Basically, he enjoyed a majority of common stock, so he couldn’t be fired.” 

The executives scrambled and reached out to the partners at ExWorks Capital, trying to explain that Williams was a liability.

Williams, too, reached out to ExWorks, referring to the other group as “pretenders” and asking for another $1.6 million to finish paying for Unrivaled.

ExWorks sided with Williams. The COO, the CFO, and Hundley were fired. 

“Looking back, I’m like, ‘What a toxic situation!’”

The next week, at the Unrivaled tournament, Williams ran around in a Batman costume with the new receptionist dressed as Batgirl. There was a marching band, there were zombie versions of the cranky old men from The Muppet Show, there were Broadway-level production values, and there was Big Bang Theory and Star Trek actor Wil Wheaton, all for people sitting onstage at a folding table, rolling dice and throwing down cards. The theater was filled with people who were paid to be there. The software struggled. 

Over the next few months, ExWorks sent in a forensic accountant, and the remaining people from GameWorks tried to convince them to stop giving Williams money. 

“They just didn’t seem to take it to heart,” Stevens says. Instead, over the next six months, ExWorks provided Oomba with another $9 million, bringing the total to around $35 million. “The fact that they seemed to have an open spigot allowing him to do whatever he needed to do on the spending side of this? It was beyond shocking.”

In late November, the core team of engineers quit, including Hogan, who by then had graduated college and who estimates that after four years, Williams owed him six figures in backpay. And in May 2018, Oomba officially came to an end, with ExWorks taking over what was left: namely, GameWorks. (“ExWorks foreclosed on the assets and new management was installed,” explains former ExWorks executive chairman Randy Abrahams in an email.)

Hundley decided to sue Williams and Oomba, and she reached out to Ronnie, among others. Ronnie never got back to her: “I’m a sex worker, they’re going to use that against me,” she explains. Ronnie also felt confused about her role in what had happened, and she felt terrible about being complicit in any harm, especially with the people she got fired. 

In a sworn declaration for Hundley’s case, one employee said they’d heard Williams say “something along the lines that ‘Dylan is only good at getting money by sleeping with investors.’” Hundley tells me she’s unable to comment because she signed an NDA. 

During the pandemic, Williams posted on LinkedIn to draw attention to his latest venture, called Glytch. Once again, he appeared to be running the company alongside an attractive woman. This time, instead of Hundley, it was Jenna. 

Williams is also a pawn in a larger system — and according to the rules of that system, finishing the game empty-handed is hardly a victory

Ronnie doesn’t dye her hair anymore; she keeps it black. This spring, she finished her associate degrees and is starting a bachelor’s, hoping to become a translator. She feels estranged from the version of herself that worked at Oomba. “Looking back, I’m like, ‘What a toxic situation!’” she says. A lot of it was fun, but she sees now that it was an empty kind of fun, papering over lies, greed, and exploitation. “With money comes power: to be able to go places and be like, ‘Yeah! We’re the richest bitches here!’ But we weren’t, though. We just made it seem that way, and I helped him portray that.” 

In the past few years, as she watched woman after woman come forward with stories of workplace harassment and abuse, she started to realize she needed to tell the world about what happened at Oomba.

“I know I’m not the first or the last girl, so I have to speak on it. Otherwise, I’m saying ‘Screw you’ to the other survivors,” she says. She’s sorry it took her so long to talk about what happened, but she explains, “I was 23 at the time, and I wasn’t very mature. I’m 26 now.” 

Perhaps most of all, Ronnie regrets that Williams’ tactics inspired her, however briefly, to manipulate anyone. Life shouldn’t be a game, she thinks, with people divided into winners and losers. “Everyone thinks capitalism is so great, but then you get educated and you’re like, ‘No! You’re literally leaving people starving,’” she says.  

Over the course of Oomba’s existence, a lot of people ended up as losers, and though no one is starving, at least one golf club member predicts he’ll need to work longer to build back his retirement savings.  

As for the winners here, well, Williams seems unscathed. But as Ronnie points out, Williams is also a pawn in a larger system — and according to the rules of that system, finishing the game empty-handed is hardly a victory. 

The real winner in the Oomba saga might be the only person who walked away with money to spare: the chairman of GameWorks, Howard Brand. Stevens tells me the $17 million that Williams got ExWorks to pay for GameWorks was more than the company was worth. And after Stevens and Brand spent years painstakingly bringing GameWorks into profitability, Williams fumbled the ball, with ExWorks losing almost $29 million on the chain since 2017. 

When I asked Howard Brand about what happened at GameWorks after Oomba took over, he went over everything Williams had done wrong, point by point. Reviewing the mistakes and misrepresentations of a man who wore a costume to their first meeting, Brand sounded dumbfounded. But in the end, he says, it wasn’t his company anymore. Williams, and whatever destruction he may have caused, wasn’t his problem. “I know a lot of people hate him,” Brand says, but for him, it’s nothing personal. It’s business. Everyone’s out for themselves. This is how the entire economy works. And if you’re playing to win, you can’t get caught up in minor details like what happens to the people who lose.  

“I was just primarily interested in the cash,” Brand says, in a dispassionate yet satisfied tone. “I got paid. I’m done.” 

*Names were changed to protect the identity of those involved.