Most angel investors bring the wrong mindset to startup investing.

And it's not their fault. It's how we're all wired.

If you're a dentist, a lawyer, or you work in finance doing debt deals, you've been trained your entire career to avoid mistakes. Get things right. Don't screw up.

Makes sense, right? A brain surgeon can't mess up 90% of the time. A civil engineer can't have 90% of their buildings fall apart.

But here's the thing: VCs are wrong most of the time. And that's completely fine.

The capped vs. uncapped problem

In most professions, your outcomes are binary. The job was done right or wrong. You hit the target or you didn't.

Because of this, you can't afford to mess up often. Your upside is capped.

Angel investing flips this on its head. Your upside is uncapped.

That $5k check into a pre-seed startup? The max you can lose is $5k. But if that company becomes the next breakout - your return has no ceiling.

This is the mindset shift that trips up so many new angels.

The "capped mentality" trap

I see this constantly with investors coming from traditional backgrounds.

They try to de-risk every single investment. They want safer bets. They're hoping for maybe a 3x return.

But that's backwards.

If you're writing $5k checks and hoping for 3x, you're playing the wrong game. A $15k return doesn't move the needle, and it definitely won't offset the investments that go to zero (which, plenty will).

What actually works

The best investors think differently.

Their mentality: "The max I could lose is $5k, but the gain is unlimited."

That's not reckless optimism. It's just math.

Your $5k check going to zero hurts. But it's a known, bounded loss. Your $5k check turning into $500k or more? That's the outcome that returns your entire portfolio.

You don't need to be right most of the time. You need to be really, really right on the few times you are right.

The practical shift

So what does this actually mean for how you invest?

Recognize when your old instincts are kicking in. If you catch yourself hoping for a "safe" 3x return, that's the capped mentality talking.

Shifting that mental model is what separates investors who build real portfolios from those who stay stuck in career-mode thinking.

Your career may have taught you to minimize mistakes. Angel investing rewards you for maximizing wins.

Different game, different rules.