If you’re gonna join an early stage¹ startup, there are a few questions that I think you should ask the founders. This is by no means a comprehensive list. In fact most of these questions are obvious, but sometimes the obvious ones are the important ones. Also, I’m not exactly an expert on startups, these are just based off of my limited experience.

What does the company do?

This is a really obvious question and yet it will reveal a lot. It’ll test whether the founders have a set vision or if they’re still figuring that out. You’ll be able to see how a founder pitches. Is it a crisp routine or a lot of “uhh, well, kinda like this”. Are they talking about what they will do in 10 years or are they talking about what they’re doing this week? Some vision is great but also concreteness is important.

Who are you?

Why are these people the people who should solve this problem? A standard adage for venture capital is that the team matters more than the idea. Ideas can change; the team stays. Also as an employee you are putting a lot of trust into these people. Payroll, hiring and HR will likely be a single person. Make sure you mesh well with them. And make sure they’re reasonable, trustworthy people. I would seriously consider getting some character references if the startup is very early stage.

Don’t be fooled by accolades or previous success in non-startup situations. Herbert Hoover was an excellent engineer and a terrible president. Just because someone went to an Ivy League and spent 10 years at Google doesn’t mean they have the ability to do a startup.

What is your fund raising situation and burn rate?

If the company doesn’t have money, it can’t pay you. The founder should know this off the top of their head.

How is the company going to make money?

At the end of the day, a company needs to make money. Too many founders forget that. Especially with developer tool companies, they can focus too much on the cost centers and not on the profit centers. Pay attention close attention to this part. Is it an abstract idea that they’ll get to eventually or something that they’re actively working on?

How have you validated that users want your product?

Many founders think that you just come up with an idea, build the product, and users will automatically like it. That’s not realistic. Startups are about validating the idea and adapting to what users want.

How often do you talk to users?

You can’t validate products without talking to users.

What resources are you using to learn about doing a startup?

Maybe this is a controversial take, but I don’t think it’s a bad idea to learn about doing a startup from reading books and blog posts on the internet. I mean sure, don’t take it as gospel and don’t let it override your lived experience, but it certainly beats willful ignorance. There is something to be said about learning from more experienced people.

Of course, the answer could be that they’ve done a startup before or were an early employee at a different startup. That’s a fantastic answer! What is concerning is a team of people who have never done a startup and are not attempting to learn. Willful ignorance is not a good quality in a founder. Especially if they’re from big tech, where it’s very easy to get used to floating on a bed of money generated by the most efficient economic engines in human history.

Have you shipped something to users?

Shipping is important. Too many companies wait too long to ship. If they’re hiring people and haven’t shipped yet, then that’s a little questionable. Do they have a specific blocker that is preventing them from shipping?

How much equity am I getting? How much is the strike price? How many shares? Are they ISOs? Is there acceleration? Single trigger or double trigger? Can I see a cap table?

There’s a lot of equity questions. I’d recommend reading a guide on startup equity and possibly hiring a lawyer.

What’s your opinion on code quality?

If the answer is that code quality is absolutely critical and everything needs to be done perfectly, then I’d walk away. Code quality is great, but you’re not going to raise another round or get customers because of code quality. It’s immensely frustrating having someone bikeshed your pull request when the company’s burn rate is ticking away.

This isn’t to say that code quality should be abysmal. Some amount of review and discipline is good. But it’s secondary to shipping and getting users.

How comfortable are you with making mistakes in public? What was the last public mistake that you made?

You’re gonna make mistakes at a startup. Nobody gets it right on the first try. And these mistakes are going to be public. You’ll announce a product only for nobody to use it. You’ll make a change that pisses off some users. People on reddit or Hacker News will say you’re stupid.

If the founder is not comfortable making mistakes and being embarassed in public, then they’ll probably be a very frustrating boss. They’ll get analysis paralysis on any public facing decision. They’ll be afraid to ship. They’ll be afraid to delegate. You want someone who’s willing to take risks and own their mistakes. Who’s willing to empower people even if they mess up. Failure must be an option.

Conclusion

There are certainly many founders who probably gave incorrect answers to these questions, learned from their mistakes and succeeded. Or maybe they succeeded because they disagreed with me. I have very little startup experience and am likely wrong in multiple places. This list is just my set of opinions and not any sort of definitive truth.

The point here isn’t that you should ask these precise questions. Instead, you should come up with your own list based on your own views. You should decide what are your dealbreakers for a founder. Because once you join a startup, you are assuming a lot of risk. You will be devoting years of your life to this cause, not to mention a load of opportunity cost. And at the end, if everything goes well, you’ll get a financial reward, but only if everything goes well.

The analogy I always use is that joining a startup is like being in a canoe. It’s a small boat, so one wrong move can capsize it. In a canoe, you should really care about where it’s going and who’s steering the boat. A large company is like a cruise ship. You’re not gonna be able to steer the cruise ship, but also it’s a lot harder to capsize. If it goes in the wrong direction for a bit, it’s not the end of the world.

If you’re going to get in the canoe, you should pick your questions and ask them.