Nick Bilton | American Kingpin (Episode 624)

Nick Bilton | American Kingpin (Episode 624)

Nick Bilton | American Kingpin (Episode 624)

Nick Bilton (@nickbilton) is a special correspondent for Vanity Fair, a contributor to CNBC, a former columnist and reporter for The New York Times, and author of Hatching Twitter: A True Story of Money, Power, Friendship, and Betrayal and American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road.

“I don’t believe we have crossed the line. I think we’ve just moved it.” -Ross Ulbricht

The Cheat Sheet:

  • How does a merit badge-bedecked Eagle Scout become the head of a thriving online black market worth a billion dollars?
  • What are the costs of maintaining a double life?
  • What’s the real reason Silk Road mastermind Ross Ulbricht was caught?
  • What is Nick Bilton’s unique research process for covering a story like this?
  • Is everyone susceptible to the level of Ross Ulbricht’s mix of ambition, hubris, and self-deception, or does it require a certain personality type?
  • And so much more…


powered by Sounder

(Download Transcript Here)

In American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road, Vanity Fair special correspondent Nick Bolton tells the story of Ross Ulbricht, a Texas Boy Scout who set out to build a website where anything could anonymously be bought and sold. It soon became a $1.2 billion drug, guns, and hacking tools hub, turning him into the Internet’s public enemy number one.

In an age where technology consumes every moment of our lives, people need to know how their ideas can be used positively and negatively, and this story is the perfect parable for teaching this. Listen, learn, and enjoy!

More About This Show

The story presented in American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road could be the next AMC hit series: a Libertarian Eagle Scout lives a double life and builds Silk Road, an illicit online marketplace where all manner of contraband can be exchanged anonymously — and hires outlaw bikers to eliminate threats to his autonomy. But author Nick Bilton isn’t a fiction writer. He’s a special correspondent for Vanity Fair, a contributor for CNBC, and he spent a decade as a reporter for The New York Times.

The subject of the story, Austin native Ross Ulbricht — currently serving life in prison — may as well be credited as co-author for the sheer volume of incriminating data he left behind when he was arrested in October of 2013.

“The thing with this book that was kind of astounding was the amount of information that Ross had left in his wake as he had built the site and run it,” says Nick. “For the better part of three years, literally every single communication he had with his employees, or with anyone related to the site, was captured on his computer in chat logs and emails and I was able to get access to all the stuff — including photos and videos…[and] social media profiles.

“Working with the research, we kind of built this database which ended up with…literally millions of words…and that stuff all came together and showed this version of this person — and actually showed him changing and morphing over time. Going from this kid who was like, ‘I really, truly believe this thing I’m building is going to make the world a better place,’ and then by the end of it, sanctioning the murders — and paying for the murders — of people that have wronged him on the site or could potentially lead to its demise.”

Directed by a Libertarian ideology that appeals to many, Ross Ulbricht (adopting the nom de guerre of The Dread Pirate Roberts as inspired by Cary Elwes’ character in The Princess Bride) was led to create Silk Road as a place where anyone would have the freedom to buy and sell anything without fear of government intrusion. Initially, it was a place to peddle his own magic mushrooms — something he considered a victimless crime, but could warrant a life behind bars if discovered and persecuted in his home state of Texas.

“I don’t think that he ever thought that he would be caught,” says Nick. “[In a chat log] he has this conversation where he says, ‘I will eventually be able to unmask myself as The Dread Pirate Roberts…because I will eventually prove that legalizing drugs is going to make the world a safer place.'”

Listen to this episode of The Art of Charm in its entirety to learn more about the slow but sure transformation of Ross Ulbricht and the double life he led to build and maintain Silk Road in secret, what Nick believes is the real reason Ross was caught, the stupid mistakes even a genius can make, how Nick walks through the footsteps of his subjects when he’s writing about them, what Nick’s non-chronological research process looks like, who still sticks up for Ross, the parallels between Silk Road and other online empires, and lots more.


If you enjoyed this session with Nick Bilton, let him know by clicking on the link below and sending him a quick shout out at Twitter:

Click here to thank Nick Bilton at Twitter!

Click here to let Jordan know about your number one takeaway from this episode!

Resources from This Episode:

You’ll Also Like:

On your phone? Click here to write us a well-deserved iTunes review and help us outrank the riffraff!

Get the Best of the Best

With over 800 podcast episodes, it’s hard to know where to start.
Let’ us help.

You may also want to listen...