The Cult of Flounder
In the beginning, Billy McFarland seemed average in every way. He was tall, stocky, and, one might say, sort of handsome-adjacent. With his squinting, pinched smile, athletic build, and preppy style, he certainly blended in physically with the other primarily white, affluent kids at the Pingry School, the coed prep school in Short Hills, New Jersey, from which he was flung into the unsuspecting world in 2010.
Like most of the families who sent their kids to the then-$30,000-a-year private school, the McFarland family lived in suburban comfort. McFarland’s parents, Irene and Steve, made their money in the loosely defined arena of real-estate development. They had the requisite shore house, annual vacations to resorts in places like Aruba, and nice cars to drive around town. McFarland and his sister grew up secure in the knowledge that they would be able to attend private colleges without having to take out loans, though McFarland wouldn’t end up making it past his freshman year at Bucknell.
But despite his comfortable upbringing, McFarland had a laser focus on making money—and he didn’t seem to care whether any of it was aboveboard. In fact, it was almost like he needed to feel like the smartest person in the room before he could even get started on something.
According to McFarland, his first business venture occurred at the tender age of seven, when he apparently realized he had an opportunity to coax some money out of a girl he had his eye on.
“My first combination of technology and marketing happened in second grade,” McFarland said in an interview featured in Hulu’s Fyre Fraud.32 “I was put next to a girl who I had a crush on, and her crayon broke. I said, ‘If you give me a dollar, I’ll fix your crayon.’”
Then, for good measure, he claimed, he hacked his teachers.
“I figured out the school’s administrator password, and I started messing with them. I changed the password and, like, locked all the teachers out,” he continued. “So every time the AlphaSmart was turned on, it would say ‘For your broken crayons, basically come and find me.’”
Setting aside his inclination to fleece the girl he liked instead of, say, doing her a favor, McFarland’s deep-seated need to start building capital in the second grade set the stage for what was still to come. McFarland made wanting more than what he had his entire personality. Sure, his parents had money, but his family wasn’t the flashy kind of New Jersey wealthy. But some of his friends—a number of whom would later work for him—were that kind of rich. And McFarland, who friends described as talkative, somewhat “scattered” (though “not in an ADD way”), and always “the life of the party,” became a sort of mascot for them.
“Billy always had something going on, even in middle school,” explained childhood friend Eric Rubenstein.
In the seventh grade, for example, jealous that they couldn’t get on Facebook, which was only open to college students at the time, Rubenstein and McFarland ended up creating their own version. They named it “Your Hot Site,” a knockoff of Facebook’s original “Hot or Not” page that Rubenstein says they selected in large part because the domain happened to be open.
“We got together with a few of our friends, and they invested in it, and we built it. Me, Billy, and another person were the admins on the page, and it was cool. It was pretty rudimentary. There was a thing where you could rank your friends and be like, ‘Who do you like more?’” Rubenstein recalled. “It got really popular after the first week, we had a thousand users after the first couple of days. And I know in today’s standards that’s not that much, but we were just kids, just fucking around.”
Unfortunately, they were forced to shut the site down not long after launching, Rubenstein said, when the school found out and called McFarland’s parents in for a meeting.
“I think the worry was that if something bad were to happen as a result of this website, it wouldn’t be a good look for the district. So Billy’s parents asked him if he could just sell it, and that’s what we did. We sold it for $3,000 to a guy in Canada. I want to say his name was Mike, but I can’t remember,” Rubenstein said.
Rubenstein has tons of memories of hijinks with McFarland, including one bat mitzvah party where they sneaked into an adjacent office area and programmed all the computers so that photographs of women’s breasts would pop up every time someone pressed “X.” Another time, he recalled, McFarland burned him a bootleg copy of The 40 Year Old Virgin and labeled it as the animated film Madagascar so that Rubenstein’s mother wouldn’t find out and ground him for watching inappropriate movies. The R-rated comedy, however, was positively tame compared to another one of McFarland’s schemes: a business he built selling passwords to porn sites to his preteen buddies.
“Billy was always looking for ways to monetize things, and it’s completely understandable since he was offering a service that no one else could provide,” Rubenstein said. “Billy was a fun kid and he was very funny.”
That was the thing—it wasn’t just that McFarland had the unique ability to provide special services for his cohort. He also had a way of making it all seem so exciting.
“[Billy] was fun. He was really funny. He was always a big flirt,” says another high-school friend who asked to remain anonymous because she would later become a victim of his schemes. “He was a fast talker, he’d go from one thing to the next, and his mind was always bouncing around.”
McFarland has been referred to on more than one occasion as a “used-car salesman” kind of personality, which made sense because he did always have some sort of fantastic deal queued up for his friends. During his last year at Pingry, for example, he led his friend group in a series of senior pranks, including one where they faked a wild party, buying a keg of root beer and rolling it into the senior lounge. Another time, they took advantage of the school’s honor code and gathered up all the backpacks their classmates had—up to that day, at least—felt comfortable leaving unguarded in the hallways during assemblies. While their unsuspecting classmates sat in the auditorium, Billy and his friends deposited all the bags on the football field, then sprayed the students with water guns when they tried to retrieve them
It was, looking back, not all that different from the Fyre Festival, which marked the end of its first (and last) day with a crowd of desperate millennials tearing through a pile of wet, unmarked luggage.
By that point in Billy’s young life, other patterns were also beginning to form. Though McFarland later claimed to have started and sold three companies before graduating high school, none of his claims were ever exactly “verifiable.” Like the business McFarland says he launched in elementary school, “behind my parents’ back when I was 12 years old, getting my friends’ parents to invest.”
According to McFarland, that business was a web-hosting company he had launched that somehow led him to employ three people working full-time in India.
“When he came to Pingry, he was already running some overseas server operation, renting out server space to various websites, most of which were porn sites,” a high-school friend named Aaron Davis told Death and Taxes. “He always kind of toed that line of whether it was a scheme or legitimate.”
McFarland later called the venture a massive success and often referred to it as evidence of his business acumen, which helped his self-created image as a child genius. “Four days after the website launched, I was forced to sell and subsequently gave each investor a 3x return on their investment,” he wrote in a 2011 investor pitch.
In a 2017 interview with the producers of Fyre Fraud, however, McFarland repeated the story, though this time to highlight how easy it had been for him to deceive his overseas employees.
“I’m talking to people entirely across the world when my friends are playing kickball at recess. I had, like, the worst fake deep voice on the planet. I would pick up the phone and never say how old I was,” McFarland said. “The internet doesn’t have parents, doesn’t have teachers, doesn’t have rules.”
That, in particular, was an important realization for McFarland. If there was ever a through-line to all of McFarland’s schemes, it’s that they occurred primarily over the internet, were valued not by their worth but by his enthusiasm, were targeted at his fellow millennials, and appeared to be designed to acquire as much money and attention in as short of a time period as possible. In that way, Billy was not unlike other start-up founders such as Theranos CEO Elizabeth Holmes or WeWork CEO Adam Neumann, both of whom also rode waves of hype to become rich and famous at the expense of their investors.
But McFarland was a peculiar sort of millennial entrepreneur, one who started out just as Instagram began to gain
attention—and with it, the rise of performative wealth among the underage scions who first sparked the Rich Kids of Instagram Tumblr page and subsequent reality television show. Like many of his eventual customers, McFarland was a fan of the milieu, which had originated as a fan page following the antics of a group of jet-setting millennials with wealthy, largely absentee parents. What made these kids different from the
famous-for-being-famous socialites of yore, however, was that they weren’t just content to be outrageously rich. This new breed was dedicated to documenting it with photos, videos, and comments that showed exactly how they were spending it.
Suddenly, almost overnight, “doing it for the ’gram” had become a viable business model. But there was a catch that’s still active for most people hoping to make money as an influencer, which is that you had to have money already.
As a college dropout still getting his family’s support, McFarland might not have had to worry about paying his credit card bills while he figured things out, but he couldn’t compete with the conspicuous consumption playing out every weekend at New York City clubs like Le Bain and 1 Oak—at least not without using his friends’ wealth to fill in the gaps.
“I don’t think [the McFarlands] were a private-jet family, but there were two other people from our high school who I know were involved in his first company, and they are private-jet families, so I know he was definitely rolling with those kinds of people,” a former Pingry School classmate told me.
More importantly, McFarland had figured out that “those kinds of people” might give him even more than he asked for, if he played his cards right. When he got really enthusiastic about a plan, most of the people around him, he was starting to learn, were happy to go along with him for the ride.
“He definitely was a dreamer and he had big ideas and they were good ideas. I think he just would get wrapped up in the scene, and trying to be this big shot in New York City. And we all thought like, ‘That’s great. We all want to be that,’” the former classmate said. “We all thought if we were part of it, we could probably ride the wave, just like you would do with any start-up or anything like that. I mean it just takes people that you might trust, or they think they know you, and then you ask them for some favors. And if enough people buy into it, then it can get pretty big.”
There, the classmate trailed off. “But yeah, I don’t know what it was that caused him to just lie constantly… I don’t know.”
Rubenstein has his own theory, which he pinpoints squarely to their upbringing.
“Growing up in Short Hills, we were basically raised to think that we were invincible, and it shows with him, and it shows with me and my friends, because we would do some really stupid shit and not face any consequences,” said Rubenstein, who realized the rest of the world lived a bit differently after moving away to Los Angeles. “Short Hills…I don’t know if it’s still that way. I only go back for funerals and Millburn Deli. But the culture, I mean, it’s a very stereotypical rich place. You can only succeed if you’re a doctor, a lawyer, or go to an Ivy league school. There’s no accepting mediocrity, and I think that they raise you to have more materialistic values.”
Despite the town’s values and some of his best efforts, however, Billy had managed to graduate high school without any felony arrests. He matriculated at Pennsylvania’s Bucknell University in the fall of 2010, with the intention of studying computer engineering, but by the spring of 2011, he was no longer a student.
Hype by Gabrielle Bluestone
From former Vice journalist and executive producer of hit Netflix documentary Fyre comes an eye-opening look at the con artists, grifters and snake oil salesmen of the digital age—and why we can’t stop falling for them.
We live in an age where scams are the new normal. A charismatic entrepreneur sells thousands of tickets to a festival that never happened. Respected investors pour millions into a start-up centered around fake blood tests. Reviewers and celebrities flock to London’s top-rated restaurant that’s little more than a backyard shed. These unsettling stories of today’s viral grifters have risen to fame and hit the front-page headlines, yet the curious conundrum remains: Why do these scams happen?