Startup lessons

People deciding which startup to join often underestimate how much the founder^[1] should matter in their decision.

To start, you should reframe your perspective. It's true that startups are interviewing you, but really you are interviewing them. I think this is common advice, but I find it rare that people truly internalize what this means. As an employee, you are signing yourself up for years of toil and pain, with the dream of a large payoff in the end.^[2] A huge factor in this coming true is how good the founder is. The earlier stage the company, the better signal you can collect, either directly from the founder themself or from people who work with them all day.

There are a few things I look for:

First, what you and the founder wants out of the company needs to be roughly the same thing. A founder-employee dynamic is not an even playing field and incentives don't just naturally line up. Let's say you're joining a newly minted Series B unicorn. Many people in the founder's position would already feel like they've achieved success. They could start planning for an exit. Or they could let their foot off the gas a bit and be content with cashing out some equity in private liquidity events or future fundraising rounds. Meanwhile, you'd be joining to work on a different goal -- grinding super hard for a 10-100x payoff that won't happen if the founder is not locked in with you for the same thing.

I'm not saying that you shouldn't join a startup at that size. But you do need to make sure that the founder is still hungry. Startups die if a founder gets bored.

A related quality a founder should have is grit. Being a founder is excruciatingly hard. They need to be mentally stronger and more resilient than everybody at the company. This is hard to discern before joining a startup, because it's only when times are truly tough that you can see this in action. When you're interviewing for a startup, even the most candid people will not fully peel back the curtain on past crises.

What you can do is ask people directly how they feel about the founder. Do they talk about how much they trust the founder to always figure things out? Is there a general feeling of reverence and belief in the founder and company's future? A focused and promising startup should come across a bit like a cult. Startups die if a founder gets tired.

Lastly, the founder should have integrity. Joining a startup is willingly putting yourself in a situation with extreme information assymetry. Of course, things like early exercise and founders sharing the same vesting schedule can give some reassurance.

But at the end of the day, there will always be some way that you could get screwed. It wouldn't be with strictly evil intentions either -- it could be as simple as the founder choosing an option that benefits them at the expense of others. Good founders should recognize this power dynamic and go out of their way to earn your trust. Your dream dies if the founder screws you.