American Kingpin by Nick Bilton is the story of Ross Ulbricht, the creator Silk Road, arguably the most dangerous website to have existed on the Internet.

Here are some of my notes from the book:

1. Fundamental belief

“It is not the government’s right to tell the people what they can and cannot put in their bodies,” Ross began, going on to explain that drugs—all drugs—should be legalized, as it would make society safer and people have a right to do what they want with their bodies.”

“How can you legalize something that kills tens of thousands of people a year?” The College Democrat agreed.
Ross calmly countered, “So do you think we should outlaw Big Macs from McDonald’s too, because people gain weight and have heart attacks and die as a result of them?”

The fundamental belief which ultimately led Ross Ulbricht to create Silk Road. Shows a lot of what we currently find right or wrong has been made so for benefits of big corps or people in power.

2. Ability to code up a prototype yourself is a superpower

“He spent innumerable hours writing front-end code, back-end code, and code that helped sew those digital dialects together. Ross was teaching himself all of these programming languages on the fly. He was technically doing the equivalent of building eBay and Amazon on his own, without any help and without any knowledge.”

Ross did the majority of the coding work on his site on his own. Only later he asked a friend for help. The fact that he can get a prototype out on his own was very powerful. Also, he couldn't have asked for help - as mostly what he was doing was illegal, and even he understood that.

3. Everyone has their struggle

“And he certainly didn’t tell them that the gaming simulation he had been building for months, which would simulate a seasteading project, had failed, as no one wanted to purchase it. He didn’t mention all those odd jobs he had done off Craigslist to make a few dollars, including editing science papers. He didn’t say that everything he had done had felt like a complete failure to him. One brilliant idea after another that no one else thought was brilliant.”

If you leave aside that what Ross created was illegal, the sheer audacity of his goals was remarkable. And if, even he, has had such periods of doubt, why should the rest of us have it any easier? In a way, the struggle strengthens your muscles to endure things.

4. Intentions, always good?

“René then went on to explain that he had experienced an epiphany of late, that we all work so hard in our jobs, and for what? “There is no level of success that would make me feel happy all the time,” he reflected. “Those little achievements are little fleeting moments.”
Ross scratched his beard, seemingly disagreeing with his friend. “I imagine there is some silver lining to . . . pushing yourself to the limit,” Ross said. “I’ve had similar experiences with my work, where that becomes everything, more important than anything.”

“I want to have had a substantial positive impact on the future of humanity by that time,” Ross remarked.”

In his own mind, Ross was trying to have a good impact on humanity.

5. How things turn bad

“If word got out that it was okay to sing to the cops and steal hundreds of thousands of dollars in cash, the Dread Pirate Roberts wouldn’t be the most feared pirate sailing the Dark Web, but rather a weakling pushover. The Silk Road would be known as a place where you could break the rules without reprisal.
This led to the third option for Green: killing him.”

In an effort to preserve what he was creating at Silk Road, Ross made a very rational decision of killing someone. Shows that there's a very thin line between right and wrong. Morality and immorality. And many times, it justs depends upon the story we tell ourselves.

6. Killing someone, justified?

“Yes, but the use of force is completely justified if you have to defend your own rights or personal property,” young Ross had argued while discussing one of the latest Murray Rothbard books he had devoured. Back then it had just been idealistic, hypothetical banter by a group of college students.”

“Now, as the Dread Pirate Roberts, the more Ross thought about it, the more he wondered if beating Green up would be enough of a punishment to deter others on the site from betrayal. He started to wonder if he might not have a choice but to put his libertarian theories to their ultimate test. Curtis Green had, after all, stolen DPR’s “personal property.” All $350,000 of it.”

So, the ordering of the killing for Ross aka Dread Pirate Roberts was just putting his theories to practice.

This eerily reminds me of Dostoevsky's Crime and Puninshment, where the protagonist Raskolnikov logically argues that killing the old woman was the right thing to do.

7. Repeat. Repeat.

“One of the strangest of these idiosyncrasies was the bizarre fact that he read everything—literally everything—three times. It didn’t matter what it was; if it had text on its pages, Gary would read it once, then again, and then once more. When he received an e-mail, he would read it three times before replying. He would read news articles three times. Books; text messages; research papers; someone’s tax forms. He did this, he told people, to ensure that he remembered more information than those around him. When he was younger, he had heard that the brain retains only a small percentage of words when you read, so he reasoned that if he started consuming every snippet of text at least three times, he would remember more.”

There's a very curious character of Gar Alford, who works at IRS and apparently reads everything 3 times. By going through the same material three times, he is able to catch nuances and details which others tend to miss.
So someone in 2011 was already practising the mantra of going slow which the tech world is slowly adopting now.

Slow
Art of going Slowly

8. Mission and Meaning

“Let me tell you a little parable,” Dread wrote to one employee. “It’s the middle ages in Europe. . . .” He went on with the story: A man “walks onto a construction site and he sees a group of laborers carving stone blocks for a building. Most of the men are working slowly, with long, unhappy faces. “What are you doing?” the man asks the laborers, to which they reply, “What does it look like we’re doing? We’re carving stone blocks.” But then the man sees another worker who has a glint in his eye and a smile across his face. This worker seems to be toiling at twice the speed of the others, and his stone carvings are impeccable. So the man goes over and asks him, “What are you doing?” To which this laborer looks back and answers: “I’m building a cathedral to the glory of God.”

Human beings seek meaning in the work they are doing. You provide them meaning - they can withstand anything. A great book to read on this topic is Man's Search for Meaning by Viktor Frankl in which he talks about how the captives in the Nazi concentration camps survived arduous conditions.

9. What can a single person do?

“ That every single person can have a sweeping and massive impact on the world they live in. Some choose to have a positive effect, others a negative; some don’t know the difference. But most people think their role in this big, big world is meaningless. Just a job.

Here, Jared, one of the homeland security agents who helped catch Ross Ulbricht reminisces how he had set out to end Silk Road based on a single pill he had caught in the customs checking. How these pills were destroying the fabric of American society and how his work has prevented it from debilitating further.


Ross Ulbricht was finally caught and was given a double life sentence. He is serving his term now and will possibly remain in jail for the rest of his life.

For those interested, many believe that Ross Ulbricht was railroaded and there's campaign to get his sentence reduced.