All of us are prone to overconfidence regarding all manner of skills and characteristics, including ethicality. (See our video:  When that overconfidence approaches grandiosity, danger lurks. We just read Nick Bilton’s engaging and moderately terrifying American Kingpinthe story of  “Silk Road” founder Ross Ulbricht, who’s website became the Amazon for drugs, guns, explosives and all manner of illegal items.

We are particularly drawn to the story because Ulbricht launched Silk Road while living in our own Austin, Texas.  Growing up, he was a “joy to raise” according to his mother. He was an Eagle Scout. He had many friends and was universally considered kind, compassionate, and peaceful. After college, he owned and operated a nonprofit. He was uninterested in owning “stuff.”  Women found him lovable.

Ulbricht also had extreme libertarian views, harbored a strong desire to change the world, and wished to be a billionaire by age 30. Put all that together, along with the fact that Ulbricht was very bright and very driven to make his parents proud, and you have an explosive combination.

In 2011, at age 26, Ulbricht used Tor, a software that enables anonymous communication, and Bitcoin, the cryptocurrency, to build Silk Road. Buyers and sellers of drugs could meet online and do deals that law enforcement could not penetrate. This degree of secrecy enabled Ulbricht, who took a commission on each transaction, to build Silk Road into a $1.2 billion business that made him tens of millions of dollars before he reached the age of 30, by which time he had been arrested and was on his way to serving a federal sentence of life plus 40 years. But for a time, Ulbricht flew very high.

In many ways, Ulbricht reminds us of Elizabeth Holmes of Theranos infamy. (See our blog post: Both were the fortunate children of well-to-do Texas parents. Both were very bright and quite attractive. Both were driven. Importantly, both felt they were destined to change the world for the better. Holmes was determined to reinvent medical testing and thereby revolutionize health care. Ulbricht was determined to defeat the various governmental “wars on drugs.” His libertarian beliefs viewed any attempts by the government to prevent people from buying any drug they wanted and putting it into their bodies as impermissible infringements on liberty that could not be countenanced. The Silk Road was going to end any war on drugs because it would be futile for any governmental agency to attempt to defeat the Silk Road’s secure electronic market.

How did kind, compassionate, lovable Ross Ulbricht become the Dread Pirate Roberts (the name he borrowed from the movie The Princess Bride in order to provide a layer of cover from the authorities)? Many of the impediments to ethical living that we address in our Ethics Unwrapped videos appear to have played a role.


Because of the slippery slope, people often find that cutting a small corner can lead to cutting other corners that grow larger and larger over time. And they may not even notice. One physician who had done horrible things in service of Hitler’s “final solution,” explained: “In the beginning it was impossible. Afterward, it became routine. That’s the only way to put it.” (Lifton)

As the business done on the website and his income from those activities grew by leaps and bounds, Ulbricht found himself taking measures that slowly grew more and more extreme to protect it from law enforcement, hackers, potential competitors, and even his own employees. With so much at stake, he felt that he had to make an example of one of his employees who had stolen from him. Ulbricht ultimately ordered the employee’s murder (which thankfully did not actually occur, because undercover cops intervened to fake the target’s death). In Bilton’s words:

Ross was obviously torn up by what he had done. Killing someone wasn’t an easy decision, but he also knew that this was something he might have to do again in order to inoculate his empire against those who threatened it. There was no fate worse to him than losing control of what he had built.

It was, after all, his legacy, the thing people would remember him for two hundred years from now.

As with the soldiers of Reserve Police Battalion 101 who initially found murdering Jews at Hitler’s direction to be gut-wrenching, but soon got used to it (Browning), Ross got used to it and soon had ordered and paid for a total of five murders to protect his empire. As Bilton put it, “It seemed that murder…was becoming easier to execute with practice.”

(Lack of) Transparency

Moral emotions are probably the strongest force keeping most people doing the right thing most of the time. If we do wrong, we feel guilty. If others find out, we also feel embarrassment and shame because others will feel anger and disgust because of our breach of moral norms. “Watched people are nice people,” says primatologist Frans de Waal. Studies show that people are much more likely to do the right thing if they feel they are being observed than if not. Children wearing Halloween masks are more likely to breach instructions not to take too much candy than children without such masks. (Diener et al.)

The Silk Road was a completely anonymous exchange system where transactions were unobservable to law enforcement. Ulbricht also hid his name from discovery. And, eventually, he adopted the Dread Pirate Roberts sobriquet, giving him a third layer of anonymity. As Berman and Hanuka write: “The thing about taking on a new identity is that it is fundamentally a lie. To the world at first. And then to yourself.”

Would sweet, kind, peaceful Ross Ulbricht have ordered murders? Unlikely. But once he gave himself a second identity—that of a pirate, he did. Probably not a coincidence.

Moral Disengagement

Like most of us, Ross Ulbricht thought of himself as an extremely moral person. Therefore, in order to do things that were blatantly illegal and would, obviously, normally be immoral, he had to confabulate reasons why it was morally permissible for him to violate drug laws and order people to be killed. Bandura points out that people often disengage their acts from their moral standards.  One way they do so is through the use of euphemisms, which make the bad acts seem not so bad. The Nazis dehumanized the Jews, for example, by calling them “vermin” and similar terms. Ulbricht routinely used negative euphemisms regarding his enemies—government agencies and employees. He universally called governments “thieves” and FBI agents “feebs.” In Ulbricht’s mind, the government was the enemy so whatever he did, including breaking untold numbers of laws, to defeat that enemy was permitted. He paved the way for this, in part, by using euphemisms.

Another form of moral disengagement is the rationalization, and a famous type of rationalization is “denial of victim.” When people hear themselves say, “I know I shouldn’t have done that, but that guy deserved to be screwed,” they are using a denial of victim rationalization.  You don’t need to feel bad about yourself when you’ve injured someone if they deserved it. And Ulbricht’s hatred of the government made him feel that anything he did to flout laws and regulations was well-justified. Indeed, he hoped to put all governments out of business.

Role Morality

Role morality occurs when people adopt different moral codes for the different roles they play in their lives. They may be pillars of civic virtue while playing the role of parent and neighbor in the community, but jettison their personal ethical code to play the role of “loyal employee” who will do anything to advance their employer’s profit goals. Ulbricht explicitly stated: “I’ve got this separation between personal and business morality.” He would “be there for a friend to help him break a drug dependency, and encourage him not to start,” but when running Silk Road he believed that it wasn’t his place to say what people could or could not put into their bodies.” Furthermore, it was his goal to ensure that the government could not tell them either.

Self-serving Bias

Obviously, the more money Ulbricht made, the more of a hero he became to libertarians and drug dealers around the world for espousing their views that the government was the evil party in attempting to stop drug use, the harder it would be for him to conclude that the things he was doing to preserve his empire were immoral.

Moral Reasoning

As he reasoned through the propriety of his actions, it seems that Ulbricht applied a utilitarian approach. Selling illegal drugs and ordering murders would not typically pass deontological muster.  While utilitarianism is a legitimate (and probably our preferred) means of calculating whether or not a particular action is moral, it has its weaknesses. Accurately calculating whether a particular action will create more good than harm–will bring about the greatest good for the greatest number—is often fraught with difficulty. The harm caused by having someone killed is fairly obvious. As is the harm of facilitating the sale of heroin that causes one buyer to be addicted and another to die by overdose.  What can you put on the other side of the scale to justify those harms? Well, if you are grandiose enough, you can manage. Elizabeth Holmes was, in her own mind, going to revolutionize health care as we know it. That grand result could certainly justify committing a few frauds to keep the project going until her equipment could actually begin producing the promised results.

Ulbricht envisioned himself as a libertarian hero who would bring down all the governments fighting their unjust wars on drugs. “I want to have a substantial positive impact on the future of humanity by the time I die…. I think I might.” He predicted: “What we are doing will have rippling effects for generations to come.” Well, if you’re going to change the course of Western civilization, that’s a pretty heavy weight to put in the scales across from the mere harm of taking one life (or five). In the eyes of the grandiose, there may be nothing that can possibly be put on one side of the utilitarian scales to outweigh all the good they are going to do the world by reforming healthcare or ending pointless wars against drugs.

Grandiosity is dangerous indeed.



Albert Bandura, Moral Disengagement (2015).

Joshua Berman & Tomer Hanuka, “The Rise and Fall of Silk Road: Part One,” Wired, at

Joshua Berman & Tomer Hanuka, “The Rise and Fall of Silk Road: Part Two,” Wired, at

Nick Bilton, American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road (2017).

Cara Biasucci & Robert Prentice, Behavioral Ethics in Practice: Why We Sometimes Make the Wrong Decisions (Routledge, forthcoming 2021).

Christopher Browning, Ordinary Men: Reserve Police Battalion 101 and the Final Solution in Poland (1993).

Frans De Waal, The Bonobo and the Atheist: In Search of Humanism Among the Primates (2013).

Ed Diener et al., “Effects of Deindividuation Variables on Stealing among Halloween Trick-or-Treaters,” Journal of Personality and Social Psychology 33(2): 178-183 (1976).

Robert Jay Lifton, The Nazi Doctors: Medical Killing and the Psychology of Genocide (1986)

Lyn Ulbricht, “Trump’s Visit to Phoenix Gives People Hope. Mine is He Commutes My Son’s Life Sentence,” AZ Central, Feb. 19, 2020, at





Moral Emotions:

Moral Reasoning:

Overconfidence Bias:


Role Morality:

Self-serving Bias: