Bitcoin Billionaires

by Ben Mezrich

  Howard Winklevoss Sr., the twins’ grandfather, hadn’t been a miner his whole life, but he had started out as one. A self-taught mechanic, he had helped a wealthy man whose car had serendipitously broken down on a road nearby his family’s homestead in Mercer, Pennsylvania, where he lived with his parents and eleven siblings: six brothers and five sisters. This wealthy man paid him so handsomely for fixing his car that day that Howard Sr. was inspired to leave the coal mines behind and start fixing cars full-time. Eventually, with the man’s help, he put together just enough money from his mining days to open a makeshift garage with his brothers, earning themselves the nickname “Barnyard Garagemen.” Howard Sr.’s father, the twins’ great-grandfather, was very upset at the time, because he thought horses were far superior to the auto—you could rely on them, they didn’t break down, and cars couldn’t work in the field. But eventually Howard Sr. would go on to start multiple businesses, including a general store.

  Howard Jr., the twins’ father, had picked up a love for automobiles and an entrepreneurial spirit from his father, and had nearly flunked out of high school because he’d spent all his free time building a Model A Ford from scratch. He would work at his father’s general store each day after school, then, after dinner, would work on the homemade car until late in the evening. Everyone around him had told him he was crazy and that it would never pass the Pennsylvania inspection requirements. He scrounged parts and pieces from junkyards, garage sales, and mail order catalogs, obsessed with getting the Model A perfect, down to the very last nut and bolt.

  He’d finished the car in two years and managed to pass state inspection, making it road legal. But he barely survived his high school exams. Nonetheless, he drove his chopped and channeled hot rod down to Penn State and rolled into the admissions office, looking for a spot. The older lady behind the desk took one glance at his transcript and sent him packing. Undeterred, he headed to Grove City College, where he managed to impress their admissions director with what he had built.

  At Grove City College two important things happened: he continued to develop the entrepreneurial skills that he had learned from his father, and he met his future wife, Carol Leonard.

  During freshman week in 1961, Howard and his parents were in line for registration in front of Carol and her parents. Carol’s mother, Mildred, playfully pointed out the handsome guy in front of them to Carol. Unknown to Carol at the time, Howard’s parents had pointed out the attractive blond girl behind them to Howard. A month later, when Howard and Carol phoned home, they both had “you’ll never guess” conversations with their parents.

  From then on, Howard and Carol were a picture-perfect match in a 1960s, collegiate, postwar kind of way. Carol, the daughter of a New York Police Department detective and a schoolteacher from New Hyde Park, Long Island, was a reserved prom queen who was more comfortable following the rules than breaking them. She was a quick study and possessed a wisdom of universal truths that you’d find in the Book of Proverbs, a book that along with the Bible, her mother often quoted. Howard was a handsome, athletic, and confident—bordering on cocky—upstart who was comfortable taking risks and getting creative about the rules. Together they were the perfect team.

  When he wasn’t spending time with Carol or his fraternity brothers, Howard was spending time on his entrepreneurial endeavors. He paid his way through Grove City selling pots and pans door-to-door. Soon he was hiring his fraternity brothers and running a mini cookware empire. Upon graduation, Howard decided he wanted to study business and better himself. Learning that San Jose State in California charged only $49.50 per credit and had few, if any, entry requirements, he headed west. At San Jose, the master’s degree in business administration (MBA) program was already full, so Howard settled on studying for a master’s degree in insurance, with the intention of working his way into the MBA program the following year.

  At San Jose, and then even more so as he continued his studies, chasing a PhD at the University of Oregon, his love for building mechanical things transferred over to the new science of early computing. It was in Oregon that a summer course in pensions—a mathematically complex area of business so obscure at the time that he was the only student that registered for the class—would change the direction of his life. An innovative computer simulation he created to compare different ways to calculate pensions led to a professorship at the Wharton School, as well as a groundbreaking book: Pension Mathematics: With Numerical Illustrations. Meanwhile, Carol earned a master’s degree and doctorate degree in education at the University of Pennsylvania, in between continuing to teach elementary school.

  Eventually Howard would leave Wharton to start a consulting firm. He hired a number of his brightest students to join him—the ones who didn’t spend their time building cars and selling pots and pans.

  Even though Howard’s consulting firm, Winklevoss Consultants, had its office in Philadelphia, he was on the road so much making sales pitches and interacting with clients that he could have lived just about anywhere in the United States as long as it was close enough to a major airport. After living in Philadelphia for over thirteen years, he and Carol, looking for a change, decided on raising their young family in Palo Alto, California.

  Back then, Palo Alto wasn’t widely referred to as Silicon Valley. It’s gorgeous weather and the fact that many of Howard’s relatives had moved from dreary Pennsylvania to settle there and start their own families made it an ideal place. As a young family, they enjoyed the beautiful town, the wonderful parks, and the excitement of nearby Stanford University. Cameron and Tyler were so devoted to the playground at the end of the street where they lived that every day, rain or shine, they piled their toys into wagons and hauled them down the street to the playground.

  While Howard worked in the home office above the garage, or was on the road starting to build his empire, Carol focused on raising young children and volunteering in the local community. Howard often remarked to his children that he owed all of his success in life to his wife. This was especially true in terms of raising his family.

  A few years later, Howard sold his company to Johnson & Higgins, one of the largest insurance companies in the world and located in New York, and he and Carol moved their family to Greenwich, Connecticut, a nearby suburb. Howard worked for Johnson & Higgins as a senior vice president for two years, commuting between New York and Greenwich, but ultimately decided he was an entrepreneur at heart. So in 1987, at the age of forty-four, he decided to start all over again and found a new company called Winklevoss Technologies.

  This company would be different from that last one. Instead of being hired as a consultant by a company to conduct a complex pension study and then deliver the finished product, Howard and his team would build the software necessary to run such studies and then sell it to companies so they could conduct the studies themselves. Winklevoss Technologies would be a software provider instead of a consultant shackled to the billable hour. At the time, the desktop personal computer was a brand-new idea. Howard’s new company would bet on the nascent technology of personal computing rapidly growing, improving, and exploding with adoption. It was the kind of risk that he couldn’t have taken without Carol’s unwavering encouragement and support.

  After school, the twins would often go to their father’s office and do their homework. In between schoolwork, they would explore the office, talk with the software engineers, read the computer magazines lying around, play on the computers, and watch from the inside how a technology company worked. Cameron and Tyler literally grew up inside of a startup, before startups were even a thing.

  The Winklevoss household was not a jock household in the traditional sense. While everyone was active and played sports, the dinner table conversations were not dominated by discussions of topics like the score of the Yankees game. Instead Howard enjoyed talking about the things that he was passionate about most—business, technology, computers, math, financial markets—while Carol rounded out the conversation with topics like li
terature, film, human interest, culture, and the arts. Howard and Carol were both intellectual heavyweights in their own unique way, and together they covered a huge swatch of knowledge and wisdom. Cameron and Tyler’s role models growing up were not sports figures; they were startup founders like Steve Jobs and Bill Gates, the people who were in the business magazines they read in their father’s office and who, like their father, were trying to change the world through technology.

  While Howard taught his children everything he knew about business, Carol ensured that they got a much broader education in life. She was determined to provide them with the opportunity to find their passion, wherever it might lie.

  Although Tyler and his brother had been raised in a family that now had money, their parents never let them lose touch with their family history, and not just their father’s coal mining ancestry. Carol’s forebearers were also German immigrants who came to the United States in the nineteenth century with nothing but their dreams. Carol’s grandfather was a fireman and hotelier in Rockaway Beach, her uncle served in the U.S. Army during World War II and fought in the Pacific Ocean theater, and her father was a homicide detective. Like Howard’s family, Carol’s family embodied good Christian morals and believed that a person’s word meant something. Howard and Carol had grown up believing that the world was a place where honesty and the ability to work hard were respected above all else. Winning was not what mattered: what mattered was that you gave your best effort and conducted yourself with the highest integrity and character. As Howard Sr. had always told his son: “I don’t care how many follow in my tracks, I just want to be the first person making footprints in the snow.”

  “I remember when you and Cameron first started out,” Tyler’s dad said. “Everyone looked at you cross-eyed. Leaving campus and disappearing off into the woods to row.”

  Tyler laughed. He and his brother hadn’t grown up in coal country—far from it—but that didn’t keep them from cutting their own path—or trying to create those first footprints in the metaphorical snow. Two overly tall, identical kids stood out in the Lord of the Flies atmosphere of high school, and not always in a good way. Being obsessed with Latin, computers, and building web pages didn’t exactly help. Nor did studying classical piano for twelve years, or teaching themselves how to code in HTML. The twins of this era were a far cry from the final clubs jock stereotype Mark Zuckerberg would later peg them as being at Harvard. But a quirk of geography had led to the passion that had eventually dominated their early life and changed their standing in the local, athletically centered community.

  It had all started with their next-door neighbor, a kid named Ethan Ayer, who was six foot nine and ten years older than the twins. He had gone to boarding school at Andover, which had one of the best rowing programs in the country. He would later go on to row at Harvard and then Cambridge University. When he’d come home to visit, he’d told these great stories about rowing, about being out on the water, competing with other rowers from all over the world. Tyler and Cameron had been intrigued. Their mother had started checking the local yellow pages and realized that there were no rowing programs in Greenwich. Even though there was water everywhere, and adults in the town who had rowed back in boarding school and college, there weren’t any local rowing programs for Tyler and Cameron to join. Calling marina after marina, their mother was told that the only rowing they did was when a motorboat ran out of gas.

  Still, she’d persisted and eventually found a rowing club in Westport, Connecticut, thirty miles north. One summer day in August of 1996, she packed up the twins in the car and drove them to what turned out to be an abandoned wooden building—the original Westport Train Station—with a rowing club squatting inside. This humble club, sitting on the banks of the Saugatuck River, had been founded by an Irishman named James Mangan a few years earlier.

  The twins entered the long wooden boathouse and, not finding anyone inside, made their way down the overgrown path to the water; there, in the middle of the path, they first ran into Mangan. When his eyes locked onto the two of them—fifteen-year-old mirror identical twins, already well over six feet tall and still growing—he’d broken out in an ear-to-ear grin. He’d made some comment in his thick Irish brogue about God dropping them on his front porch: a righty and a lefty who were exactly the same, growing every day. He immediately agreed to train them.

  When they’d first started, they weren’t really sure what the hell they had gotten themselves into. The old train station had no running water, no electricity, no heat, and you had to be careful where you stepped or you’d fall right through the floor; the nearest locker room was the restroom in the Mobile station across the street.

  On their first day on the water, in an old, rickety practice shell that was partly held together with duct tape, Tyler and his brother managed to take a total of eleven strokes. Mangan, grinning the whole time, told them that one day they would take hundreds, sometimes more than a thousand, in a single practice. And never mind the duct tape or the condition of the hull: this sport wasn’t about the chariot, it was about the horse. Most importantly, the boat didn’t care who you were, where you were from, the size of your wallet—it cared only about what you did.

  “We thought you were nuts when you said you weren’t going out for any varsity teams,” Howard said. “I thought your mom was nuts when she made me put an ergometer in the attic.”

  Tyler winced, remembering the brutal training device, more akin to a medieval torture machine, and how many winters he had spent up in that attic, pulling the chain on that mechanical monster. But it was the ergometer that had pointed them toward the Olympics. Every month, teenagers from across the country would submit their twenty-minute erg test results to US Rowing, which would post them to the US Rowing website. When Tyler and Cameron discovered that their own scores were in the top ten in the country for their age, they realized that there was a possibility they could compete on an entirely different level.

  They then decided to lobby their private school’s headmaster to create a varsity rowing program, the first ever in Greenwich. With the help of their father, they’d found a slip at a nearby dock in Long Island Sound and convinced a few of their classmates to sign up. The twins were two kids who had known nothing about the sport, who had trained and sweated (partially in their attic) until they were good enough to compete at the national level, making the US Junior National rowing team and competing at the 1999 Junior World Championships in Bulgaria. Then they’d built their first startup—a high school varsity rowing team—from scratch. That startup had helped get them into Harvard via early admission—because the twins weren’t simply athletes; they were the definition of “scholar athletes,” polymaths who had proven their mettle in both the classroom and on the water—and building their startup would put them on the strange path into another world where they were also starting from scratch.

  To them, the art of crew really was a microcosm of startup life; it had taught them how to work on a team and succeed under pressure, where the difference between winning and losing could be razor-thin. Cameron had often remarked that some of the best lessons in his life he had learned at the boathouse—and they had very little, if anything, to do with the sport of rowing.

  * * *

  Tyler pivoted the conversation to the reason he and his brother had invited their father to Tod’s Point. “We know more about Bitcoin right now than we knew at fifteen, when we took the leap into rowing. That was a big decision then, and this feels like a big decision now.”

  Tyler had always relied on his father for business advice and mentorship, not only because his father was a legitimate mathematical genius who had built a successful consulting company the same way he’d built a Model A Ford in high school, from the ground up, but also because he still considered his father to be the most ethical, high-integrity person he’d ever known. Maybe it was the coal country in the man, but Howard Winklevoss Jr. was the one who had taught them that right and wrong mattered, that a handshake wa
s more important than any contract a lawyer could draw up. When the situation with Zuckerberg had first gone down, their father had been the most shocked of any of them about how the young Facebook CEO had acted. He wasn’t a naive man, but he couldn’t process how someone could behave so deceitfully, and with such disrespect. He’d supported Tyler and Cameron in their efforts to make things right, even when they’d turned down the cash settlement in favor of Facebook stock. And to them, it didn’t matter how many lawyers had told them they were being fools; the fact that their father had stood behind them gave them the confidence to realize they were making the right decision.

  “Cameron said it first—‘this is either complete bullshit or the next big thing,’ ” Tyler said.

  His father nodded, looking out at the water. They’d already discussed Bitcoin at length on the phone and during breakfast that morning. His father had immediately seen the mathematical beauty behind the now three-year-old cryptocurrency. The elegance of the blockchain—the open, decentralized ledger where transactions were permanently recorded—immediately made sense to him, and the brilliance of Bitcoin itself, of a currency backed by math and cryptography, with a fixed supply mined by computers running complex equations, certainly thrilled his mathematical mind. But he shared Tyler and Cameron’s concerns about Silk Road, and the shady side of the Bitcoin world.