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HOUSEKEEPING 📨

Today’s piece took me a while. But at the end of the day, I’m pretty happy with it. When Donald Trump pardoned Ross Ulbricht recently upon returning to office, my need to understand the Ross story really spiked. I have buddies that can’t believe he went to jail, they say the whole murder for hire story was a scam. Some even say he was not the man behind the wheel in the end.

Who really knows the truth of it. I have my conclusions, which I won’t spoil for you now. Other than that, things are well. I have a cracking post I am working on for you for next week. A new unicorn zero to one story. And a bunch of new bangers in the works. Anywho, I present to you today, the story of Ross Ulbricht, the Dread Pirate Roberts.

PIRATE DEEP DIVE 🕵🏻

THE DREAD PIRATE ROBERTS

In the Dune universe, the Lisan al Gaib is a legendary messianic figure, with a cult-like following, who is prophesied to wreak havoc across the galaxy. But the Lisan al Gaib did not start with evil intentions, he started as Paul Atreides, a young man, with a good upbringing, who set out to leave the world better than when he found it.

Depend on whom you ask—the story of The Dread Pirate Roberts shares similarities with the story of the Kwisatz Haderach, Paul Atreides. This is the story of a bright, charismatic, Libertarian idealist, Ross Ulbricht. And his desire to create a better way for people to express their individual freedoms, and a safer way to buy drugs online.

Before I continue praising the pirate captain of the internet-drug-superhighway, I need to also tell you that this was also a man, who—again, depending on who you ask—became obsessed with power, and had a ruthless desire to see his vision through.

The Silk Road was Ross’ magnum opus, and he wouldn’t let law, life or love get in the way of slowing it down. This is the story of Ross Ulbricht, the Dread Pirate Roberts.

A young Ross

Ross William Ulbricht (/ˈʊlbrɪkt/; born March 27, 1984) was born and raised in Austin, Texas. A lover of the outdoors, Ross was a proud Boy Scout, reaching the Eagle Scout ranking during his time in the outdoors. All things point to Ross having a regular, happy childhood, with loving parents, white picket fence and all the elements to set ones self up for success.

Following on from his early years, Ulbricht would attend the University of Texas at Dallas on a full academic scholarship, graduating in 2006 with a bachelor's degree in physics. Ross would also receive an additional scholarship to attend Penn State, where he was in a master's degree program in materials science and engineering and studied crystallography (yes, that type of crystal: krústallos; "clear ice, rock-crystal").

It was during his studies that Ross began to take a keen interest in libertarian economic theories. Ludwig von Mises, Ron Paul, and the whole conservative economically, uber-liberal personally kinda way of thinking. The thought that if you’re not hurting anyone else, you should be free to make your own choices.

That means less government telling you what you can and can’t do, and more trust in people to decide for themselves. This libertarian lens in which Ross viewed the world was the spark that started everything for Ross and what would become him in the future.

The history of the Dark Web

First, to understand the Dark Web, we need to understand how the internet works in general. And really, there are three levels to it that you need to understand today. They are the Surface Web, the Deep Web, and the dark, dangerous world of the Dark Web.

If you picture it like an iceberg, The Surface Web is the part floating above the water—the stuff search engines like Google can easily find. Think your favourite news sites, blogs, online stores, and social media. It’s what most of us use day-to-day. The Deep Web is the element of the web that is below the surface. This area is bigger—much bigger—than the Surface Web. It’s any content not indexed by search engines. Things like private databases, password-protected sites, your email inbox, Netflix, internal company sites, all live in the Deep Web. It’s not necessarily secret or illegal; it’s just not publicly searchable.

And then we have the Dark Web. Way down in the murky depths is the Dark Web, which you can only reach with specialised tools like the Tor browser, we have the sketchy part of the internet. It’s a subset of the Deep Web—small in comparison, but infamous because it’s often (though not always) home to illicit markets, hacks, and, ironically, some whistleblower communities. Essentially, it’s where you’ll find the under-the-radar stuff that folks don’t want in plain sight. For simplicity, sake I created a simple table explaining the internet for you.

The Dark Web really began to gain steam in the early 2000s, around the time our young protagonist Ross was just finishing high school. The release of the Tor (The One Router) browser in particular, made it possible for a number of journalists, activists, and whistleblowers to remain anonymous on the internet. But it didn’t long for the opportunity to exploit internet anonymity to shift to drugs.

That is when the Dark Web really took root in media and pop culture. People realised there was an entire hidden layer of the internet, and it fascinated them.

We’re skipping ahead here, so let’s rewind to the very beginning of the Silk Road story, back to the idealistic young founder who believed he could rewrite the rules of online commerce—and in doing so ended up remaking internet history as we know it.

A budding Web 2.0 founder

In political debate clubs, on campus and between his inner circle, Ross would often talk passionately about what was and was not deemed to be legal. The contradiction that cigarettes and alcohol were legal, but weed and mushrooms were not prodded at his libertarian roots on a daily basis.

Ross had already dipped his toe in the water entrepreneurially (word of the day) with his own online bookstore. Now in 2011, following on from his discovery of the Tor browser, the stage was set for him to undertake a much bigger project, the anonymous, Dark Web, market place, the Silk Road. Being that Ross was relatively useful at writing code, he put together a simple, elegant marketplace site, threw together a little green camel as a logo, and went into the business of moving drugs online.

The name ‘Silk Road’ was a choice Ross made in relation to Asia’s historic, thousands year trade network that linked Asia, with Europe, Africa, and the greater world. The original Silk Road was named after the highly lucrative silk trade that originated during the Chinese Han Dynasty a couple of thousand years ago.

During the early days of launching the site, there was only really one person who knew the inner workings of it, the love of Ross’ early life, his girlfriend, Julia. They were a typical young, and happy couple. They hung out, went camping on the weekends, and they just more than anything adored each others company. But there was always friction in their relationship.

Julia, like any normal person, just wanted to be in love with Ross. For Ross though, the idea of the Silk Road was not just a project, or a way to become financially secure, it was a movement.

He would go on to preach the philosophy of this movement to his budding disciples by saying; “Silk Road was founded on libertarian principles and continues to be operated on them. It is a great idea and a great practical system...It is not a utopia. It is regulated by market forces, not a central power (even I am subject to market forces by my competition. No one is forced to be here). The same principles that have allowed Silk Road to flourish can and do work anywhere human beings come together. The only difference is that the State is unable to get its thieving murderous mitts on it.”

The fire had been lit under him now. And the unfortunate truth was that anything that came between him and his vision, was likely to be discarded, including his former identity. The young, idealistic libertarian, Ross William Ulbricht was beginning to fade away. And in his place, his alter ego, the Dread Pirate Roberts was beginning to take hold. 

‘It’s Amazon—if Amazon sold mind-altering chemicals’

One of the most consequential thing to happen to Silk Road in the early days was what is simply referred to as; The Gawker Article, a piece by a young report, Arian Chen, that catapulted the Silk Road into the public consciousness.

So much so that it prompted Senator Chuck Schumer to demand that the Department of Justice take down the site. This type of notoriety was a double-edged sword for Ross and the team.

The next Zuckerberg

Founders that were coming up through the same time the Silk Road was taking shape were names you would know today like; Uber’s Travis Kalanick, Mark Zuckerberg from Facebook, and Brian Chesky from Airbnb. If you were able to take a trip backwards in time to around the year 2009, and convince a young Ross to out his energy into a project that didn’t need to reside in the dark underbelly of the internet, Ross’ name may be in that vaulted list of celebrity founders.

Sure we know Ross’ name today, but not for his fame and success, but for his infamy (you could argue Kalanick is the same to a degree here), when it should be because of both. Come 2011, the Silk Road was growing, and growing fast. Vendors were now selling weed, prescription meds, benzos, books on how to be a hacker, LSD, and even guns.

But not only was the SKUs inside of the Silk Road expanding rapidly, it’s revenue was going gangbusters. In 2011 the site took in ~$15M in revenue, by 2012 it had ballooned to $92M, and in 2013 it was a whopping $1.2B in total transactions, with ~$80M in bottom line commissions back to Ross and the team. To put that into perspective, let’s look at the rough revenue growth of two of the Web 2.0 superstars of this era.

This is why Ross Ulbricht should be remembered for his excellence as much as his malevolence. He was a revolutionary. And his story lead to one of the ultimate conversation starters across a dinner table; ‘What could Ross have been if he had chosen a legal pathway into business?’

I guess we will never know. But I, for one, would harbour a guess that he would have gone down in history as one of the great founders of our time.

Zenith

By 2013, Silk Road wasn’t just another black-market operation—it was an institution. If the Dark Web had a Wall Street, Silk Road was its New York Stock Exchange. Transactions flowed in torrents, Bitcoin soared in value, and the Dread Pirate Roberts etched his name in history for being at the helm of what had become the largest decentralised black market in history.

By 2013 one single, solitary, website was attributed to a ~20% share of the total worldwide movement of Bitcoin. That website was the Silk Road.

Why was the Silk Road so successful?

_{*Note: I make no apology to the use of Big Lebowski GIFs through this section. Not everything in life needs to make sense. Some things are awesome just because.}

Up until now I bet you are wondering how on God’s green earth did the Dread Pirate Roberts pull this off. It’s not as if you can spin up a few great Meta Ads campaigns, or grey hat some amazing SEO strategies as the leader of an underground drug market.

You also can’t really rely on hiring the best and the brightest. The most recent batch of Stanford grads aren’t rushing out the door to get an internship at the Silk Road. So what was it about the Silk Road that led it to being so successful.

Throughout this section, I am going to breakdown the success of the Silk Road across three different levels; (1) tactical, execution-level moves, (2) strategic longer-term positioning and defensibility, and finally (3) conceptually, the philosophical and business foundations of the company.

Tactics (execution-level moves)

• Escrow system: Implementing a smart trust mechanism where funds were held until the buyer confirmed receipt, reduced fraud and increasing transaction confidence.

• Reputation & review system: Borrowing from eBay/Amazon, vendor ratings meant a meritocratic marketplace where reliable sellers thrived.

• Fast customer / founder support: Dread Pirate Roberts engaged with users directly via forums, creating a founder-led community model that made users feel heard.

• Community-driven virality: Early growth came from word-of-mouth in libertarian and hacker forums (think Hacker News for the dark web), building organic adoption.

• Referral growth loops: Power users brought in more buyers/sellers because network effects increased transaction liquidity, the same playbook Uber and Airbnb used in the early days.

• Smart shipping SOPs: Vendors refined packaging, tracking codes, and shipping methods to lower detection risk. Getting packages safely delivered was the difference between 5-star reviews and jail time after all.

• Automated money laundering: Bitcoin was anonymised through ‘mixers’ before withdrawals, ensuring untraceable cash-outs for vendors.

Strategies (long-term positioning + defensibility)

• Building a lean, remote, fully distributed team: Silk Road with minimal headcount, outsourced key tasks—like moderation—and relied on community-driven content reviews, vendor policing and more. A classic Web 2.0 marketplace strategy.

• Regulatory arbitrage: The combination of Tor + Bitcoin + escrow transactions made it hard for traditional law enforcement to apply legal frameworks. Similar to how Uber operated in cities before regulations caught up.

• Platform stickiness via repeat purchases: Drug buyers are quite literally the stickiest recurring customers, not one-time purchasers. This would create a high lifetime value per user, making Silk Road more retention-heavy than typical black markets.

• Demand aggregation: Instead of fragmented street dealers, Silk Road aggregated global supply & demand, unlocking scale efficiencies like Amazon or eBay.

• Trust layer as a product feature: Unlike Craigslist (where deals are high-risk), Silk Road de-risked transactions through escrow, reputation scoring, and refund policies, creating a consumer-friendly UX.

• Dark Web distribution strategy: Instead of using traditional paid ads, Silk Road relied on growth via dark-web forums, Tor-only SEO, and underground influencers—hackers, cypherpunks, drug forums and the like.

Concepts (foundational principles)

• First-mover advantage: There was no prior mainstream darknet marketplace, so the Silk Road effectively became the Amazon of illicit goods, and built a moat around that via word-of-mouth and brand dominance.

• Leaning into founder mythos: By choosing the Dread Pirate Roberts identity, Ross not only implied that leadership was transferable, he built himself into a messianic internet figure, that would be followed into battle by his disciples.

• Platform liquidity flywheel: More vendors means better selection, means more buyers, which means more vendors, and so on. This self-reinforcing network effect was, again, taking inspiration from Amazon’s marketplace flywheel.

• Libertarian brand alignment: Positioning themselves as a revolution in free trade appealed to folks who see government oversight as Big Brother.

All said, the Silk Road leveraged anonymity, economic incentives, and Web 2.0 UX mechanics to create the most trustworthy, liquid, and scalable illicit marketplace in history. Replace drugs with legal commerce, and Silk Road could have been a billion-dollar Web 2.0 startup. But for all the successes of the Silk Road, it was beginning to get crushed under the weight of its own illegality.

“I WOULD HAVE NO PROBLEM WASTING THIS GUY”

It all began to unravel for the Dread Pirate Roberts in early 2013, after he allegedly ordered a murder-for-hire targeting Curtis Green, a Silk Road administrator. This decision was influenced by suspicions that Green had stolen around $350,000 in Bitcoin from the site.

In February 2013, Ulbricht was said to have paid an undercover DEA agent $80,000 to carry out the hit. To convince Ulbricht that the murder had taken place, agents staged Green's death. They photographed the supposed victim lying face down, appearing lifeless, with his body smeared in Campbell's Chicken & Stars soup to simulate the aftermath of asphyxiation.

Ross was never charged for attempting this murder, but this event marked a point in time when the Dread Pirate Roberts began to look a whole lot less like underground, libertarian, idealist, and a whole lot more like an alleged, evil-doer who will happily murder people when he sees fit. I understand that humans are innocent until proven guilty, but there were four more alleged cases in which Dread ordered hits on people who had done him and the Silk Road wrong.

Below, you can find a transcription from the Silk Road forums in which on the 26th of March, Ross is working some enterprise sales with a user known as “redandwhite," who claimed affiliation with the Hells Angels motorcycle club. And in this next chat, four short days later, you can find Ross haggling over the price of a hit with this same user.

The final day before the arrest of the Dread Pirate Roberts was the definition of life imitating art. On October 1, 2013, in scifi section of the Glen Park Branch Library in San Francisco, the Silk Road founder was finally arrested by federal law enforcement. At the time of his arrest, he was said to have been downloading an interview with Vince Gilligan, the creator of Breaking Bad, from the previous night's episode of The Colbert Report.

_{*I doubt there is truth to this claim, but you do see the Breaking Bad narrative in most versions of the story.}

Simultaneously and most importantly, he was logged into Silk Road's administrative interface under the username of his famous pseudonym, Dread Pirate Roberts, at the time. FBI agents orchestrated a perfect diversion to snatch his laptop before it could be encrypted, making sure to capture critical evidence of his involvement in the illicit marketplace.

Sentencing, and eventual pardon

During Ross’ trial, he begged the judge to; “leave a light at the end of the tunnel” ahead of his sentence. “I know you must take away my middle years, but please leave me my old age.” But in 2015, Ross Ulbricht, was sentenced to two life terms plus 40 years without the possibility of parole. A sentence that to some seemed harsh for a first-time, non-violent offender.

Since then, of course, things have changed. Ross tweeted in March of 2024; “Today I turn 40. I pray I’ll get a second chance at freedom before this decade ends.” To some surprise, his prayers would be answered less than 12 months later when incoming Present Donald Trump officially pardoned Ross for his crimes.

The murky legacy of Ross Ulbricht

How to interpret all of this is really in the eye of the beholder, and how much of it is true, we’ll never really know. I really love this powerful passage by the author Nick Bilton, who told the story in his book, American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road.

But did Ross set out to be the God like figure of his own universe? Did he envision that his libertarian values of freedom to choose would lead him to (allegedly) choose to put people to death? The funny thing is, I think Ross did order these hits. But I think he did it because he believed the juice (death to few) was worth the squeeze (freedom for many). The Silk Road was his pièce de résistance, his ultimate triumph.

It was to him, a place where people could truly be free, without governmental oversight as to what they could put into their body, or what experiences their consciousness could achieve. In time we may actually find that Ross was right. Many early studies have shown that Ross’ marketplace is safer. One study went as far as to call the Silk Road a “transformative criminal innovation.”

The study would go on to say; “Our observations of exceptionally positive feedback found for listings that often even included the ostensible results of lab tests for strength/purity suggests that buyers were convinced they were getting what they paid for.” In other words, seller were selling higher quality drugs. And buyers were buying that high quality product, safely.

And with that, it brings us to the end of our story. The story of the internet’s original anti-hero, Ross William Ulbricht, the Lisan al Gaib of the dark marketplace, the Silk Road, and the Dread Pirate Roberts.

Dread pirate philosophy

For some bonus material, here are a few of the thoughts of the Dread Pirate Roberts over the years, shared in the chat rooms of his own Silk Road marketplace.

Fun facts

• ‘Dread Pirate Roberts’ inspiration: The founder cribbed his pseudonym from The Princess Bride, evoking the idea of a legendary pirate identity that could be passed along to new ‘captains’ in the future.

• Dark Web copycats: The Silk Road was so successful, that many copycats markets popped up in the wake of the shutdown. Silk Road 2, in fact, operated for nearly 12 months shortly after the original sites takedown.

• More than just drugs: For period of time on the Silk Road (and sister site The Armory) you could buy rocket launches, uranium ore, NSA contact lists and more.

• Bitcoin’s big break: Many credit Silk Road for giving Bitcoin its first real adoption wave, turning a then-nerdy crypto experiment into a legitimate—albeit illicit—currency for online commerce.

• Massive FBI seizure haul: When the Feds finally shut it down, they confiscated a staggering amount of Bitcoin—tens of thousands of coins—making the government (temporarily) one of the biggest Bitcoin whales on the planet.

Extra reading

• Read the Transcript of Silk Road's Boss Ordering 5 Assassinations - February, 2015

• Silicon Valley Murder Mystery: How Drugs and Paranoia Doomed Silk Road - May, 2017

• He Helped Create Silk Road—But Ross Ulbricht Should Be Freed - May, 2024

And that's it! You can find Ross on X under @RealRossU and also on his Medium where he occasionally shares his thoughts.

BRAIN FOOD 🧠

If you want to understand the insane grift of the $TRUMP and $MELANIA coins this is a great listen by This Week in Startups. It's particularly poignant hot on the heels of the new rug pull from Javier Milei. The fact that Trump shifted the Overton Window for acceptable behaviour as a President tells me we will likely see more political figures robbing their supporters blind like this.

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