Eight minutes into our interview, I asked behavioral scientist Jason Halbert what goes into building a psychological profile on someone.

As an interrogator, he naturally turned the tables on me.

“If you had me profile you — you have a tremendous digital signature, right? You’ve published a lot, you’ve written a lot, you’ve commented a lot, so that gives us a good insight,” Halbert said.

Normally, Halbert would assess the person’s digital signature (a large sampling of tweets, comments, and posts). Then, Halbert himself would conduct a two- to three-hour semi-structured interview with the subject. And finally, if needed, his team would interview other people in their orbit.

For this piece, Halbert and his team built an abbreviated version of the psychological profile. He calls it an “indirect assessment,” or a psychoanalysis that relies on available, open source data they collected on me.

Some of the key traits his team identified include, “pleasing nature,” “reliance on mentorship,” “intrinsic motivation,” and “an intellectual attraction to disputatiousness.” Along with a brief explanation of how these traits manifest, there’s also a gray box that denotes “a risk.”

Below is an example of how a cautious approach to risk can be a double-edged sword:

A psychoanalysis like this can be valuable for an investor when evaluating a founder or for a company hiring an executive. Halbert has experience with both, having served as the Vice President of People at Snap during the company’s hyper-growth phase.

Today, he’s the founder of 3Back, a behavioral science consulting agency and a partner at an early-stage investment firm named Era.

But prior to his work in the tech industry, Halbert spent a notable amount of time interrogating terrorists as an officer serving the U.S. Army Special Operations Command, interviewing more than 150 murderers, and working as a legal and crisis consultant for several Fortune 50 companies.

Has his experience interrogating psychopaths helped him in his current role interviewing startup founders?

“There are psychopaths who rule governments [and] who rule businesses,” he says. “And look, there’s a fine line between being highly influential and highly manipulative for your gain in a destructive way. I think, too often, when we’re recruiting executives, the individuals interviewing them haven’t actually touched or seen the extremes of human behavior.”

In this conversation, Halbert explores the complexities of the human mind, the commonalities between serial killers and startup founders, and the fine line between ambition and delusion.

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This Q&A has been lightly edited for clarity and length.

(Below is an excerpt, but I encourage you to listen and watch to the full interview below.)

🎧 LISTEN.

Meet the Behavioral Scientist Who’s Interviewed Serial Killers, Terrorists, Spies, and … Startup Founders Polina Marinova Pompliano Episode

🎬 WATCH.

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I wrote a deep-dive on FBI agent John Douglas, who explains that most murders are relatively easy for law enforcement to understand, but that’s not the case for serial killers. What can you tell us about the psyche of serial killers and how they differ emotionally from other criminals?

HALBERT: There are individuals who, many of them, just robbed a gas station or they killed someone in a bar fight. There’s nothing very interesting about their story. It’s horrific and has a lot of victimology in it, but the individuals who have cyclical maladaptive patterns are a little different.

Because [their crimes] are often random, right? It’s someone targeting the underprivileged, it’s someone targeting a sex worker, or someone involved in prostitution. So that’s harder to catch. With DNA now, it’s a lot easier to catch them with technology.

I spent so much time with violent criminals in my doctorate, and my clinical director said, ‘You need to speak to white-collar criminals.’ And I said, ‘Oh, that’s so boring.’

I spent almost a year and a half [working on] nothing but white-collar crime, and I will tell you it was incredible because I began to have this deep, profound [realization]: ‘Wait a minute, Bernie Madoff is as detrimental to society and as psychopathic as Ted Bundy because he destroyed thousands of lives, he destroyed marriages, and people committed suicide.’

[Madoff] is as destructive as a serial killer.

Do you believe that anyone is born destined to be a murderer thanks to some “killer gene,” or does it hinge more on what happened during their formative years that would lead to this type of behavior?

I think it’s both.

If you’re predisposed for sensation-seeking and having less anxiety, okay well, those are great for successful criminals.

However, they’re also great for successful military operators. They’re great for successful business people. So the traits are there. Now, sprinkle on a really horrific childhood, some substance abuse, and maybe a head injury, and you have a recipe.

Those [experiences] don’t culminate with psychopathy, but most psychopaths have everything I just described.

So if we’re inclined to be more risk-taking, more hedonistic, and more sensation-seeking, then yeah, that kind of lends toward crime, but also [toward] founding a company or serving your country or being a racecar driver.

So those traits don’t necessarily portend unfavorable for for a person.

When you’re evaluating a founder, how can you distinguish the line between ambition and delusion?

I jokingly say, “If you’re evaluating a founder, you should be a clinician, too.”

You should be a clinician who has interrogated, who has interviewed, who has worked with some of the best disruptive technologists in the world.

Sometimes people are just delusional. Sometimes that delusion road runs very, very close to technology that’s going to change the complexion. And there’s a fine line between hubris and confidence.

When I look at someone with a great idea that’s unbelievable, I often don’t look at the content, I look specifically at the audience who doesn’t believe it and why.

You may not believe it because you were recently burned. You may not believe it because this person reminds you of your son. So I like to look at the most thoughtful, ‘no’s.’

If I’m a VC or CEO and I need to quickly profile the person I am interviewing, what are some good questions I should ask or what are some cues I should look for?

I tell VCs, ‘Give me time to interview them two to three times,’ because it takes a while to get through what I call ‘high-impression management.’

If you interviewed me tomorrow, and I’ve already said all this, now, what do I say? I would actually go deeper, and I would feel this compulsion to add more because I feel like I didn’t satiate your curiosity, or I feel like I didn’t do well. I wouldn’t just repeat the same thing. I would also feel more comfortable telling you more. That’s why I think great interviews or great profiles are done over time and not in a hurry.

One of the things I’ll ask is, ‘Polina, you’ve been here for eight hours of interviews with everyone. Is there anything you wish you could re-answer?”

I don’t want to see a life ruined or an interview panel dismantled because you answered a question [one way] because you didn’t understand it, and then it shoots your credibility.

So I encourage every company to ask that question.

John Douglas once said that he has a formula for identity, which is “Why + How = Who.” In essence, he says that our identity is a reflection of the things we do and the way we do them. What are your thoughts on identity, and how much can we evolve it over time?

When I sit with a really, really bad guy, I don’t feel like I’m osmotically becoming bad, right? I don’t, and I don’t have to judge them in order to feel safe.

I also have a tremendous amount of empathy for what created that. He did not wake up at 1 day old as a terrorist. He didn’t wake up at 1 day old as a serial killer. I get that. And so for me, there’s a story there, and everybody has a story. Depending on when I met him, we might have been BFFs. I really believe that, right? This guy was not full of hate at five years old. He was a misunderstood, unattended to kid.

Many people think, ‘Unfortunately, if people only really knew who I actually was, no one would love me.’ So [they] create this ideal self. This ideal self is what I put out there. I put it on Instagram, I put it out there all the time. It’s exhausting. You start liking this ideal self. Now, I’m more exhausted because I have to imitate this, but God, if you knew the bad people I dated, the drugs that I’ve done, the money I’ve stolen. And this is why we conflate affection with attention.

So you really want to know when you feel great, it’s when you put this ‘actual self’ out and people reciprocate. Now you’re like, ‘Wow, this is what real connective tissue feels like because you know my demons, and you still love me?’

I think we are struggling because we have this dual identity because of technology, but try to surround yourself with people and things that help you close the gap between ‘actual’ and ‘ideal.’

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