The Seven Habits of Highly Effective Drug Dealers

In American Kingpin, Nick Bilton likens Silk Road founder Ross Ulbricht to his Silicon Valley peers.

Just over two years ago, a federal jury convicted Ross Ulbricht, the then-30-year-old creator of the online marketplace Silk Road, of conspiring to distribute narcotics, among other charges. In announcing that Ulbricht had received a life sentence under the so-called kingpin statute, the Department of Justice compared his transgressions to those committed by crime bosses in the offline world. “Make no mistake,” said Preet Bharara, at the time the U.S. attorney for the Southern District of New York, which oversaw the prosecution, “Ulbricht was a drug dealer and criminal profiteer who exploited people’s addictions.”

In American Kingpin (Portfolio, $27), a potboiler recounting of Ulbricht’s exploits and eventual capture, journalist Nick Bilton suggests an alternate archetype for understanding his subject: the Silicon Valley chief executive officer. Bilton, who covers tech for Vanity Fair, writes that Silk Road was “no different from Facebook or Twitter,” in that it was a web-based marketplace that tolerated bad behavior on the part of its users. Except instead of inadvertently facilitating, say, fake news in the case of Facebook or hate speech in the case of Twitter, Silk Road was optimized for the trade of drugs and weapons.

The site was founded in 2011 as a sort of activist project, an mall of illegal goods where the use of bitcoin ensured buyers remained anonymous. It was devious and brazen. Ulbricht, a militant libertarian with limited technical abilities who’d recently flunked out of a materials-science Ph.D. program at Penn State, hoped it would make American drug laws essentially unenforceable. By the time the FBI seized Silk Road’s assets and arrested Ulbricht in 2013, the marketplace had a half-dozen remote employees and almost a million customers—and had sold more than $1 billion in goods.

Bilton portrays Ulbricht as a gentle but radical idealist whose only possessions seem to have been a pair of shorts, a djembe drum, and a copy of The Fountainhead. The “CEO of the Silk Road,” as Bilton calls him, came into his own only after moving to San Francisco, where he rubbed elbows with Bay Area startup founders. “They had all read the same Ayn Rand books,” Bilton writes. “These chief executives shared the same quotes on Facebook as he did: ‘The question isn’t who is going to let me; it’s who is going to stop me.’ ”

In Bilton’s telling, Ulbricht eventually spun out of control, paying an $80,000 bitcoin bounty to wipe out a snitch, then justifying his moral decrepitude by comparing murder for hire to the working conditions at iPhone factories. Thankfully, no one actually died; his would-be assassins were undercover police gathering evidence as part of the investigation that eventually led to his capture. As the FBI closed in, Ulbricht attempted to cheer up his demoralized lieutenants with a cheesy motivational speech adapted from the management theorist Peter Drucker. The moment, which comes just after Bilton’s description of another murder-for-hire attempt, damns not only Ulbricht but also the entire genre of business books.

During the 2015 trial, Ulbricht’s lawyers acknowledged that their client had started Silk Road, but they alleged that he’d subsequently turned the business over to an unknown (and more ruthless) third party who framed him. Bilton’s scrupulous research, drawing on Ulbricht’s diary entries and the chat history found on his laptop, makes this defense seem absurd.

Yet the book’s cinematic approach means there’s little room to explore some of the larger questions the case raises. For instance, if the creator of Silk Road is responsible for illegal trade on the platform, do the supporters of bitcoin, who now include executives from the world’s largest financial institutions, bear responsibility for facilitating that trade? Even more pressing, if it took federal investigators two years to stop a dorm room libertarian, how effective can they possibly be against the professional cybercriminals we now face?

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