Losing Your Son to the Prison System - The Silk Road and Ross Ulbricht with Lyn Ulbricht

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You don’t have to be for drugs to be against the drugs war. It’s not really about drugs, it is about government expansion and money, because it feeds this mass incarceration in the United States. More than half are in there for drug offences.
— Lyn Ulbricht

The Silk Road was an anonymous marketplace created by Ross Ulbricht on the dark web. Designed on libertarian principles, Ross hinted on his LinkedIn profile what he was working on:

I want to use economic theory as a means to abolish the use of coercion and agression amongst mankind. Just as slavery has been abolished most everywhere, I believe violence, coercion and all forms of force by one person over another can come to an end. The most widespread and systemic use of force is amongst institutions and governments, so this is my current point of effort. The best way to change a government is to change the minds of the governed, however. To that end, I am creating an economic simulation to give people a first-hand experience of what it would be like to live in a world without the systemic use of force.

Two technologies enabled Ross to achieve his goals with the website:

  • The Tor Browser: enabled the IP address of the server hosting the website to be hidden, while also allowing users to browse and purchase from the website anonymously.

  • Bitcoin: enabled buyers and sellers to transact anonymously with each other without using debit or credit cards.*

While the website allowed for the trade of any goods, it was primarily used for and became synonymous with drugs. with listings for all types of recreational and over the counter drugs in almost any quantity.

One of the key features of the website was the ability to leave reviews of sellers, which led to a fairer system than the street trade. Sellers did not want to risk losing business, so they could set the grade of their products. This also, arguably, protected buyers by reducing the risk of 'bad batches' and sellers cutting their products with other impurities, something is often seen in the street trade to increase profits.

Ross created a pseudonym, Dread Pirate Roberts, to act as the master admin for the site and he claimed he passed this onto another person early on in the project. It was this pseudonym and master admin became the target of multiple law enforcement agencies, across the world.

In October 2013, the FBI was able to access the servers and close down the website. Ross was apprehended in an uncover sting at the San Francisco Library on October 2nd and charged with:

  • Possession with intent to distribute controlled substances (dropped in sentencing)

  • Distribution of narcotics by means of the internet

  • Narcotics trafficking conspiracy (dropped in sentencing)

  • Computer hacking conspiracy

  • Fake ID trafficking conspiracy

  • Money laundering conspiracy

  • Continuing criminal enterprise, aka the kingpin charge

On 4 February 2015, Ross was convicted of seven charges and received a double life sentence + 40 years, condemning Ross to spend the rest of his life in prison.

The case presents many complex issues, from the harshness of the sentence to the role of the state. The subject is highly emotive with valid arguments on both sides of the drugs debate. Some argue that the war on drugs is a failure and the Silk Road enabled buyers and sellers to transact in a safe and non-violent way, while opponents would say that the website made it too easy for vulnerable people to gain access to dangerous and hard drugs.

The case also brings up wider topics for discussion, should we as humans be free to put in our bodies what we choose or do we need protection from the state? Why is alcohol legal when other drugs aren't?

The Silk Road included information for buyers on the safe use of drugs and Meghan Ralston, a former "harm reduction manager" for the Drug Policy Alliance, was quoted as saying that the Silk Road was:

A peaceful alternative to the often deadly violence so commonly associated with the global drug war, and street drug transactions.

Ross' lawyers have petitioned Supreme Court, asking them to review and reconsider the lower court’s decision, based on constitutional violations in the investigation and at sentencing. If the Supreme Court rejects this, he will essentially run out of options and will spend the rest of his life in prison.

In this interview I talk to Lyn Ulbricht, Ross's mother about Ross, his arrest, the case and the US prison system. Lyn raises important questions around the harshness of the sentence and the growth in life sentences for non-violent crimes.

Ross' arrest and incarceration has had a deep impact on Lyn and the rest of the family. Our interview takes place 27th March, Ross' birthday, and it is clear how worried she is about the Supreme Court ruling. Outside of the argument over sentencing, this is a mother who has effectively lost her son to the prison system. Her relationship with him is confined to family rooms at the prison and phone calls. She may never get to watch her son get married or have children and is spending her time fighting the case.

Whatever your opinion, I encourage you to listen to this with an open mind. I also encourage you to read and research the facts of the case as there is so much misinformation out there.


* Note: Bitcoin is not entirely anonymous, the blockchain can be scanned and purchases tracked if a wallet can be associated with an identity.


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  • 00.00.00 Intro

  • 00.04.45 Current prison life for Ross

  • 00.08:44 When Lyn and Kirk first became aware of Ross' arrest

  • 00.10:41 Ross' interest in Bitcoin

  • 00.11:38 The drugs war and freedom of choice

  • 00.16:24 Did Ross commit a crime?

  • 00.20:32 With hindsight, would Ross do it again?

  • 00.25:26 Why Lyn believes this case is about Bitcoin and not drugs

  • 00.29:21 Where they currently are within the legal process

  • 00.36:10 Mass incarceration and the economics of the prison system

  • 00.41:00 Appealing to the Supreme Court

  • 00.45:08 Late release of information for the defence

  • 00.48:44 Discussing items I struggled with when reviewing the evidence

  • 00.55:35 How Lyn's life has changed

  • 01.00:42 Problems with the US prison system

  • 01.04:45 How Ross has changed

  • 01.06:34 What Lyn has learned through the process

  • 01.08:41 NSA involvement in the Silk Road

  • 01.11:58 Financing the legal case and how people can support the case

  • 01.14:19 A tipping point in history

  • 01.17:37 Hope and the spirit of freedom

  • 01.19:30 How to get in touch