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Unmasking Dark Triads in the leadership of tech startups

  • Author: Luis Sanchez
  • Published On: July 30, 2023

After reading this post, and specially if you are a technical employee, you will have the tools to discover an overlooked skill that's essential for success in any tech startup: detecting and avoiding Dark Triad personalities. In this insightful article by Xander Dunn and re-printed with his permission, Xander explores the world of narcissism, Machiavellianism, and psychopathy/sociopathy, and why these traits are prevalent in the tech industry (estimated about 20% of the leadership positions in tech), but also in other industries such as finance and insurance as well.

With my many decades of experience in finance, insurance and tech, my advice is: avoid Dark Triads leadership at all cost.

🚀 Key Insights:

  • Unveiling Dark Triad traits and their prevalence in tech.
  • Clarifying misconceptions and understanding their deceptive charm.
  • Strategies for early detection and effective avoidance.

On Dark Triads in Silicon Valley

The most overlooked skill for technical people in Silicon Valley is the ability to detect and avoid Dark Triad personalities. Why do our humanities and social sciences courses fail to impart this obviously beneficial skill?

Xander Dunn, 19 Feb 2023

Hell is empty and all the devils are here. - William Shakespeare

Evil is not an ethereal force from hell, it is just Psychopaths.

The Dark Triad

The Dark Triad refers to narcissism, Machiavellianism, and psychopathy/sociopathy. Narcissism is an outsized sense of self-importance. Machiavellianism, named after the author of The Prince, is the belief that the only thing that matters is power. Finally, we have sociopathy and psychopathy, which are defined by an inability to feel empathy for other people.

There is a common misconception that sociopaths are white-collar criminals while psychopaths are serial killers. The sensational hit book Bad Blood about Elizabeth Holmes specifically calls her a sociopath in its conclusion. This may be the pop culture usage of these terms, but it bears no relation to the technical use of the terms in clinical psychology. As a starting point, read this article. Sociopathy is defined as a lack of empathy resulting from environmental factors, such as a challenging childhood. Psychopathy is defined as a lack of empathy resulting from genetic factors. It turns out that serial killers are more likely to be sociopaths than psychopaths. Many serial killers had extremely challenging childhoods, for example physical and sexual abuse at the hands of their parents. Environmental extremes like parental abuse causing a destruction of empathy would be designated sociopathy rather than psychopathy. But, it's not hard to believe that lack of empathy can be genetic: Elizabeth Holmes' father was a Vice President at Enron where he perpetrated one of the largest frauds in US history. Furthermore, Elizabeth had an extremely privileged childhood with very little hardship. With little environmental hardship and a history of wrong-doers, Holmes probably came by her lack of empathy genetically, not environmentally. My goal here is to reveal complications in how these terms are used popularly, but ultimately we don't care whether someone is a psychopath or a sociopath. If someone lacks empathy, we don't care why, we just want to identify and avoid.

Another common misconception is that people with any of the above personalities have stunted social skills, and come across as aggressive or otherwise bad or off-putting. On the contrary, these personality types tend to have above-average pro-social skills. They tend to be very charming and very good at convincing others. See here for evidence that psychopaths can appear above average genuine when they choose. Pop culture imagines that sociopaths and psychopaths are bad at understanding others' emotions, but actually, they are above average at identifying the emotions of others. Their ability to identify others' emotions is what empowers them to use those emotions in manipulative ways to achieve their goals at the expense of other people's goals. Identifying and understanding emotions is wholly separate from feeling any kind of empathy, values, or remorse. Indeed, on the other end of the spectrum, there are highly empathetic people who are strongly affected by the emotions of others but are very bad at identifying what those emotions are.

How Prevalent Are Dark Triads?

One lens for looking at Dark Triad personality types is as an evolutionary advantage. I see these personalities as something that adversarially evolved. If your genes are attempting to get an advantage over others so that they can propagate better than other people's genes, developing a better-than-average ability to manipulate others to do your bidding is clearly an advantage. Of course, it would be bad for your genes and the genes of your entire species if everyone evolved into a psychopath, narcissist, or Machiavellian, so it's going to be an uncommon trait. I'll estimate that around 5% of the general population is Dark Triad, and I would roughly estimate that about 20% of Silicon Valley leaders are Dark Triads. If you pore over the literature estimating the common population and executive prevalences, you could come up with sums across the Dark Triad personalities that are both much lower and much higher than these numbers. Most people are decent people. Never confuse incompetence, burnout, stress, or other issues with Dark Triad.

It's particularly important for people in Silicon Valley to be aware of these personality types because they are particularly prevalent in Silicon Valley. Anywhere there is money and power to be had, you will find Dark Triad personalities in higher-than-average abundance. See various sources for the higher prevalence of Dark Triad personalities in executives, including here , here and here

What To Do?

Avoid. Simply avoid them at all costs. Identify these personalities as early as possible and just leave. Block them. Move on. It's not normal, it's not healthy, and it's not productive. You can get paid even more than you are paid now somewhere you don't have to deal with these personalities. There are all sorts of strategies for dealing with these people, such as "grey rocking," trying to be as uninteresting as possible when they've got you in their crosshairs. Forget all of these strategies. The Dark Triads are evolutionarily hardwired to withstand infinitely more emotional crap than you are. You will lose. Other than perhaps a helpless child who doesn't know better, I can think of few to no circumstances where it is truly impossible for you to just leave the situation. "It's my cofounder" doesn't count as a truly impossible situation. Trust me, you can quit and start again and everything will be fine.

One failure mode I see good people in Silicon Valley fall into after discovering these personality traits is an attempt to "use them," to align with Dark Triad people professionally in the hopes of getting the good while avoiding the bad. This is a terrible idea. You can be professionally successful without associating with any of these personalities, and you will be wholly unable to mitigate the negative effects in your vicinity even if you can name them. Knowing that arsenic is poisonous doesn't allow you to live in the vicinity of arsenic with impunity.


You should have litmus tests, principles, or "razors" in your back pocket that you continuously pull out when you meet new people. Some that I've found useful over time:

  • Avoid people who have a disregard for the truth.In its most extreme form, I know a CEO who explicitly said, "The truth doesn't matter." Given extreme statements like this, the typical response is to laugh it off, "Surely they must be joking." But in my experience, such insane statements are completely honest and should be taken at face value.

  • Has this person ever said, "I'm sorry," "I don't know," "I was wrong about that," or "You were right"?These are phrases that will necessarily come out of every sane human's mouth at various points in their life due to the simple fact that we are all highly limited in our capabilities, flawed, and imperfect. It doesn't need to be anything big. This could be as simple as a quick, "Sorry I'm late" to a meeting, or the realization that some code they wrote wasn't the right way to approach the problem. Dark Triads are typically completely incapable of uttering these sounds with their mouths. Narcissists in particular. Note that Dark Triads will expect and demand apologies from others, they just won't ever apologize themselves.

  • Avoid anyone who attempts to intertwine your personal values with your professional life, or who demands loyalty above all else.Becoming friends with your coworkers and going on outings with them is great, but that's not what I'm referring to. I'm referring to a CEO who tries to tell you who you should be friends with. A simple razor here is to ask yourself: Do I feel like I would ruin my whole life and disappoint everyone around me if I were to quit my job / quit my relationship? If the answer feels like a "yes," then you've probably got a Dark Triad warping your sense of reality. Emotionally stable leaders can handle the fact that people change, needs change, situations change, and no one stays in one place forever. If leaving the company/relationship makes you an enemy, then you've got a Dark Triad.

  • Ask them.If you ask the right questions and really pay attention and accept their answers at face value, most bad people will tell you that they are bad people. Asking if someone is a narcissist turns out to be surprisingly effective. Ask how they think about truth and what's important to them. Ask them to describe a time they were wrong about something. I once went on a first date and I asked if he'd had any relationships since moving to the Bay. He said, "I dated someone for a year but I always knew I didn't really want them." What sort of immoral person strings someone along so deeply for a whole year? Why would I expect to be any different? I once knew a CEO who told me that he ripped off his employees and he was bemused that they hadn't even fought for what was rightfully theirs. Ask and take the answers at face value. Bad people are usually happy to tell the world that they are bad people, and there's a very important realization here that the best way to predict how someone will behave in the future is to look at how they've behaved in the past.

  • Did you ever get a sense of unease shortly after meeting this person? This is likely evidence that they are NOT Dark Triad! Recall that the Dark Triads have evolved specifically to pass your trustworthiness filters.An immediate sense of unease around someone is more likely about Aspergers than it is about Dark Triad. If a Dark Triad is willing to be honest and upfront about their worst qualities: "I'm the best in the world at ____," "I am a narcissist," "Truth doesn't matter," etc, then they have no need to trip up your dishonesty detector. Different people will have differently calibrated manipulation detectors, so maybe yours is different, but I've seen this play out many times in many very smart people in tech. The people whose honesty you're immediately focused on are probably not the people whose honesty you should be worried about. Dark Triad personalities typically give an upfront sense of familiarity, not of unease. The smooth talker who has everyone in the room at ease is more likely the Dark Triad than the shifty character who twitches every time they say something about themselves.

  • Beware of the perpetual promisers. "We will do something," or "We can talk about that if you want."This is a manipulation tactic to avoid the topic. If they actually wanted to do it or if they were actually going to talk about it, then they would simply do it now, they wouldn't indefinitely delay it.

  • When you met this person, did your interactions start with a lot of idealizations? Praise on you or idealizations of what you're going to achieve?This is likely the idealize → devalue → discard treadmill. Reasonable people can cite positives and negatives, strengths and weaknesses, opportunities and risks. But if it sounds too good to be true, then it probably is.

  • Look out for false compliments,or back-handed compliments. An example would be saying, "You're cooler than I thought you were." There's no need to make such a statement back-handed and manipulative. Any sane person would've just said, "You're cool." Positives should never be conditional. If a "compliment" raises questions in your mind, then it is definitionally not a compliment, it's called negging.

  • Become good at identifying facial expressions of disgust and contemptI've found that Dark Triads often let slip micro-expressions of contempt. Not all of them, of course, but some of them view most people as contemptible.

  • Does this person default to distrust of others?In my experience, people who are quick to assume that others are lying are themselves liars. Assuming dishonesty is often an indicator of one's own dishonesty. A dishonest person rightly assumes others are dishonest because they have a lot of personal experience with being dishonest! The more brazen someone is with this distrust, the more likely we've got a Dark Triad. For example, telling someone point blank that they're lying even when there's no evidence that they're lying, or openly stating that other people are liars, again without evidence.

There are various batteries and questionnaires, including in the books I've listed below. If you read through them and it sounds familiar, you've got a Dark Triad. One example is this list from the Mayo Clinic.