The Silk Road and The Tragic End of Ross Ulbricht

I loved the book

Excellent storytelling and writing. Nick Bilton had done an amazing job here. The extensive research was well worded into a streamlined narration of the events spanning two years, with excellent background information on everyone involved.
This is the story of a young genius who watched Breaking Bad and got seduced by it. It somehow aligned well with his libertarian ideology and his entrepreneurial aspirations, and he skillfully created ‘The Silk Road,’ a one-person startup that created the most lucrative and most dangerous eCommerce business on the dark web.
It can’t be that simple, of course, there are a lot of other factors. I can see how the snowball of events in someone’s life could scoop up enough disappointment and frustration that will lead to the pursuit of outrageous ideas such as creating a global market to trade everything and anything with complete disregard for the ramifications.
The Silk Road wasn’t just a random idea, it was well thought out and had a philosophical foundation based on Libertarianism.
In the first part where Nick Bilton was doing the autobiography of Ross Ulbricht, I couldn’t help but empathize with how he had been lead down that road through luck and circumstance. It’s not easy when you feel like you haven’t found your footing in the world and that every single person you have ever known is doing way better than you. It leaves such a bitter taste on the tip of your tongue that never really goes away.
It’s kind of the same emotional background to Molly Bloom whose life has been documented in a really good book and a great movie by the same name, “Molly’s Game.”
It’s not simply that Ross Ulbricht wasn’t trying to find his success through ethical means, it just wasn’t happening fast enough. It’s always tough but especially when everyone recognizes the potential in you and your mere presence raises very high expectations in everyone you meet. People who find themselves in that precarious situation feel the full weight of their own frustration and the unspoken–and sometimes spoken–frustration of their loved ones and friends.
His ideas about the legalization of drugs are actually being proven today with the slow rollout of drug legislation in the US. It’s not so hard to wrap your head around the fact that laws that create severe market shortages for an in-demand substance consequently and immediately create black markets that will entice criminal entities to exploit the situation. Enterprising ‘criminal’ individuals and organizations will always seek to provide any contraband product to a starving market that will be more than willing to pay any exorbitant profit margins and whose customers will not be so picky about quality control.
But even if you would find some sense in the argument for the legislation of drugs, it’s a whole different situation when untraceable guns get sold anonymously by unscrupulous parties. It’s ridiculously easy to legally get a gun in the US, so much that when you try to anonymously get a weapon from a black market website, there’s no question really about your intentions being of nefarious reasons. Once Ross crossed this moral Rubicon, it wasn’t hard to find justification for more dangerous and questionable products.
Soon after, it was poisons, organ parts, and there was no telling where it would all stop, had it not been ended by the aggregation of resources from multiple US government agencies.
Nothing was happening in Ross’s life for a very long time and then everything started happening all at once. It’s the euphoria of finding success at long last, it’s the vindication of the bruised ego that his genius and hard work are finally paying off, it’s that point where a person could let it all get to their head and start drinking their own Koolaid.
Bitcoin was a major accelerant to Ross’s libertarian ideology, his entrepreneurial spirit, his business, his success, and ultimately, his wealth. There was an obscene amount of money he was raking in from his illicit dark web business in the hundreds of millions of dollars worth. And that was at the current price of Bitcoin back in 2013, which was roughly $100, now it’s $60,000. Had he been still in business today, he would have comfortably held the number one spot for the richest person in the world

So many parallels could be drawn from the Silk Road story with Breaking Bad. There was this Inevitable transformation from the goody two shoes frugal unkempt college student to a person who was the head of a behemoth dark web drug organization that was in every way anti-establishment. So was Mr. White the Chemistry school professor who’s given up on his dreams a long time ago and then was transformed under the influences of his own story into an underground drug lord who held enormous power with a shaking hand. A hand that got a whole lot more firm the longer he held that power until his inescapable demise. But where Walter White had his money hidden in a storage unit and in barrels in the desert, Ross Ulbricht had his millions hanging around the apartment in little unassuming flash drives.
No matter the underlying reason, philosophy, or the underlining of libertanianism involved, it was by the end of the day a criminal organization that cannot revert back to the justice system to settle scores or punish transgressions of any sort.

When a weak person bites off more than he can chew, that’s when they’re forced to compromise and forfeit their ethics and moral high ground. They basically paint themselves into a corner. But the crux of the matter here is that such people have their first sip of the potent cup of power after years of being at the bottom.

There’s just too much personal investment in their new powerful and accomplished identity, ego, and self-esteem, and too much ‘sunk cost‘ to let it go. They turn into a cornered wounded young tiger, and the one thing you don’t ever want to do is to corner a wounded tiger into any corners because that tiger will kill you.

It’s basically the same transformative force that pushes the fictional Walter White deep into his criminal underworld when he was forced to deal with threats and challenges. It’s not like you can take a person to court over any disagreements or transgressions, it’s the wild west, and everyone has to be able to take care of business by any means necessary, which usually involved force and violence.
In that world, a parallel universe that doesn’t play by the same rules of society, but rather vehemently opposes such laws, they must revert back to the laws of small tribes and the laws of the jungle. Leniency in that context will always be interpreted as weakness and in turn, will open the door for more daring disregard for the rules and even could get the leader killed.
No, leniency is not an option when you are dealing with the basic instincts of human nature and the dangers of catering to the desires of weak men. This is why it wasn’t entirely unexpected that The Dread Pirate Roberts, Ross’s moniker on the Silk Road, or DPR for short, sanctioned a hit on an employee who he thought stole from him and other people who he thought were posing a danger to him. The message had to be loud and clear to everyone else, for security and stability purposes.
This is where, I think, Ross Ulbricht finally sealed his fate. IT didn’t even matter to the judge that there was no proof that anyone was actually killed and that what’s happened was that he was duped into paying hundreds of thousands of dollars to gangsters who faked killing people to extort money out of him. What mattered was that he believed it, he made the conscious choice to have people killed and believed it to have happened.
I felt very sad at the end. Seeing those pictures of Ross as the nerdy smart college student who had the potential to turn his life into something different.
In the end I couldn’t help but remember something that Jordan Peterson had said, and I’m paraphrasing here: “If you think strong people are dangerous, you should see what horrors weak people are capable of.”
Order and laws are necessary. Even those who oppose the rules of society and seek to change them from outside by building their own society and their own tribes, soon figure out that they must be governed by laws, and they start making up their own.
Changing an injustice is different from trying to run a for profit business that aims to undermine the laws of government of a huge powerful country such as the United States. There’s so much food for thought here and so many lessons to glean from all this.
One thing is for sure, a very smart person will never be free again.

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