American Kingpin: Silk Road Makes Theranos Look Like A Disney Movie

A short summary of the unbelievable Silk Road story as captured in Nick Bilton’s American Kingpin

Can I make a confession?

Seriously, can I come clean about something?

For all of the reading I do, I don’t think that I’ve ever, honest-to-God, read an entire book from the very first page all the way through the very last.

I read non-fiction, so by page 200 I usually get the idea and can move on with my life. I skip around, quit boring books, and just never quite finish stuff. Sue me.

But that all changed this weekend…

I picked up Nick Bilton’s American Kingpin and quite literally could not put it down.

American Kingpin is the true story behind The Silk Road — you remember: the website on the “Dark Web” where you used to be able to buy any drug imaginable?

Oh, and not just drugs. You could buy weapons, hitmen, cyanide, human organs…

The Silk Road started as a libertarian “side hustle”

As you can imagine, the backstory of how the site came to be is nutty.

An idealistic 20-something, Ross Ulbricht, builds a website — a completely unregulated black market “Amazon.com” — to express his libertarian values and sets out to unseat what he believes is a cruel, unjust government (the U.S. government).

Ulbricht starts to build his Dark Web drug marketplace while running his friend’s bookstore. The site was a side hustle of sorts.

But before long, it takes off and starts to occupy more and more of his time.

Soon, he’s processing millions of dollars each month through his site (people love drugs!) and has built something that history’s most esteemed drug lords and startup founders alike would envy.

From hacker to kingpin

Ulbricht quickly transforms from an idealist into a cold, pragmatic, Walter White-type character who relishes the challenge of building his billion-dollar drug empire.

Ulbricht ditches his day job to go full-time on The Silk Road and begins sliding deeper and deeper into “evil” territory as his power and wealth skyrocket.

For example, here’s an ethical fork in the road he faced:

“Question for you,” one of his employees had asked at the time. “Do we allow selling kidneys and livers?”

Would you like to guess his answer?

Mhmmm…

None of Ulbricht’s friends realize what he’s up to

In true Breaking Bad fashion, the Silk Road founder carries on a normal-ish existence to the outside world for most of the story.

He lives in San Francisco with some roommates, goes camping on the weekends, works from coffee shops, and generally lives a life indistinguishable from a solo startup founder in SF (which I guess he technically was…).

Indeed, Ross Ulbricht, the leader of one of the largest drug empires in history, was indistinguishable from an SF “tech bro”:

After breakfast each morning, while René and Selena sauntered off to work, their new roommate, Ross, would wave good-bye and wander town the street to a nearby coffee shop to oversee his drug empire.

The government begins hunting for him

Before long, every three-letter agency in the government starts to hunt the person or people running The Silk Road.

They hit nothing but dead ends for roughly two years, until a semi-rogue DEA agent befriends “Dread Pirate Roberts” (Ulbricht’s online persona), chatting and emailing him frequently, weaving a fabricated backstory about being an experienced large-scale drug smuggler.

Ulbricht hires the cop to carry out a hit on a former Silk Road employee, which he “does,” successfully convincing Ulbricht that he’s loyal and reliable.

But then the cop crosses an unimaginable ethical line and… well… you know what, sorry. You’re just going to have to read this thing if you want to know.

This story, which, again, is true, rivals some of the best crime novels. There are dirty cops. Hitmen. Drug dealers. And almost as many ethical gray areas as there are characters.

But as compelling as the story is, the storytelling is worth its own mention. The book is written as narrative non-fiction and the details that that the author chose to include are brilliant.

Anyway, if you’re into these sorts of nonfiction narrative stories, here’s the link: American Kingpin.

If you’re not in the market for a page-turner, at least add the Silk Road founder on Linkedin.

… but don’t be surprised if it takes a little while to get a response. He’s in prison for the rest of his life.

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