Startup Founders and Dark Triad Traits: Use Narcissism, Strategy, and Decisiveness to Win

Hey Reader,

Let's not pretend startups are built on empathy and consensus.

Well... the most effective founders understand this is a dual dynamic. Relentlessly empathetic to their users but unapologetically decisive with themselves and their teams.

Under the surface, most startups are built on belief, manipulation, and unreasonable conviction, but without the foul names.

Don't believe me. Read the headlines. Harvey ($5bn). Lovable ($1.8bn). They are not revolutionizing code or legal AI. They are capturing situational value vs margin value. Claiming territory and moving fast matters more than having a fully differentiated product on day one. Unlocking these huge markets via category defining bold claims.

Psych calls them "Dark Triad" traits. Narcissism. Machiavellianism. Psychopathy. Literally the trifecta of red flags to avoid at all costs.

I've written about the ethical boundaries between vision and fraud, when ambition crosses into deception. An insanely thin line. This isn't that.

This is about the traits you already have and are already using, but are tough to admit and even tougher to name. Worse still, you need them.

This isn't about self-awareness of having these traits. You do. It's about permission to deploy them effectively.

This isn't about being toxic. Crossing ethical lines or having a Theranos moment. This isn't about lying to investors or screwing over employees. I wish it was that binary.

This is about recognizing that the traits psychologists label "dark" might just be the traits that make founders effective in the face of an entire market, trying to prevent their success (Porters 5).

What's "too much" for one person is perfect for another. These traits with their nasty names and toxic undertones? They're subjective (How classification shapes strategy). To you. And to everyone around you. Stop trying to calibrate how you lead or what you believe it takes to win to other people's comfort levels.

No one wants to add "I'm an exceptional psychopath" to their LinkedIn headline, but you cannot pretend you don't have these traits.

Scratch that... Some do. This newsletter came from a clip of an interview with Tyler Denk (Beehiiv) on the Social Currency podcast four days ago.

"It takes sacrifice. One of them is being a psychopath and saying I value working over everything else."

Is it psychopathy? Probably not. It's def beast mode. It's def radical clarity. It's def a founder who knows the tradeoffs he is willing to make and isn't lying to himself or to you. That's the point.

This newsletter isn't about what it takes. It's about being honest about it because the trait itself isn't inherently dangerous. Pretending it's not there is.

And now everyone in his orbit knows exactly who he is and gets to decide if that is too toxic, too much, too awful, or too honest for them.

Let's just define the titles... to keep us all on the same page around this awful topic:

Narcissism: Perhaps the core of being a founder. Getting other people to follow you. The belief that your idea matters more than the status quo, that it could actually change the world. That this matters.

How else could you ask people to quit their jobs, take equity on forward-looking promises, and follow a vision no one else can see? A bit delusional but wholly necessary.

Because a founder without narcissism is a founder no one follows. They can't. You can't hire, fundraise, sell, because you won't even fight for your own mission.

Machiavellianism: Is even worse because it's the underlying strategy that drives the outcomes you want. The mayhem of incentives, equity, and messaging that makes people do a thing.

The shitty definition would be manipulative. But we're not looking for that, we're looking for strategic. We are saying, with the right dose of Machiavellian instinct, it's about alignment in a direction that's a win for them and for you.

You have to build systems that win. That close deals. That raise money. You have to design systems that motivate behavior.

Because being your "authentic self" means no FOMO, no urgency, and no extraordinary reason to say yes.

Psychopathy: Is the easiest one to see in the mirror and often the hardest to accept. It's holding two contradictory thoughts and still making a call. Shipping a product and taking money, knowing it's far from perfect. Terminating someone with what feels like no thought or remorse.

You're not deceitful. You're not manipulative. You don't lack empathy. Except... you kinda do. It's the toxic titles of sociopath, cold, heartless.

You can't carry everyone's emotions and still lead or wait for complete information and still move fast. The luxury of consensus doesn't exist.

It's your company, your bank account, your reputation, your vision. You have to be the one who sets the target.

And despite the shitty labels do people really want forward-looking equity in a company run by a truly lovely, clever, deeply empathetic founder that doesn't make hard calls, moves everything to consensus and is on another zoom looking for full alignment and complete data? Prob not.

There are so many waivers in this newsletter, because none of this is about being toxic. None of this means you don't care about your team. It just means you're willing to make the hard calls so they don't have to. In a really uncomfortable way, the magnitude of your success is often tied to your proximity to the line, how safe do you play it.

So why is this even a newsletter? Because this matters. There's a massive cost to denial and pretending you don't have these traits shows up:

• Burn out searching for perfect.
• Outmaneuvered by competitors.
• Lack of urgency and conviction.
• Incapable of running at startup speed.

You have to switch your thinking. You're not broken (ish), you're equipped. We know that what separates effective founders from wannabes isn't just EQ. We hear it over and over again:

• Hold unshakable belief while keeping your eyes and ears open.
• Understand how to pull people in while genuinely caring about them.
• Make hard decisions quickly and take responsibility for the consequences.

You're not a psychopath. You're not toxic. You're not unethical. You're a founder using founder tools. And if you don't your competitor is.

You don't have to be proud of the dark edges and these shitty labels. But you do need to own them. You chose this life. So stop apologizing for having conviction, strategy, and decisiveness. Go get impossible things done.

You can be genuinely caring AND uncompromisingly decisive. You can be kind AND have unshakable conviction. They're not mutually exclusive.

If I can be of service, feel free to grab time.

LFG.

-- James