“Billy always had something going on, even in middle school,” explained childhood friend Eric Rubenstein. 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. But some of his friends-a number of whom would later work for him-were that kind of rich. Sure, his parents had money, but his family wasn’t the flashy kind of New Jersey wealthy. McFarland made wanting more than what he had his entire personality. 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. “So every time the AlphaSmart was turned on, it would say ‘For your broken crayons, basically come and find me.’” I changed the password and, like, locked all the teachers out,” he continued. “I figured out the school’s administrator password, and I started messing with them. Then, for good measure, he claimed, he hacked his teachers. I said, ‘If you give me a dollar, I’ll fix your crayon.’” “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. 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.Īccording 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. 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.īut 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. They had the requisite shore house, annual vacations to resorts in places like Aruba, and nice cars to drive around town. McFarland’s parents, Irene and Steve, made their money in the loosely defined arena of real-estate development. 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. 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.

He was tall, stocky, and, one might say, sort of handsome-adjacent. In the beginning, Billy McFarland seemed average in every way.

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