How to choose which startup to join

A framework and system for making a better decision

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You are probably familiar with Sheryl Sandberg’s now popular advice to job-seekers: “If you are offered a seat on a rocket ship, don’t ask what seat!”

I think this advice is problematic in that it misses probably the most important point. It’s really hard to figure out what startup is actually a rocket ship! And, oftentimes, the companies claiming to be “rocket ships” are actually total duds in the long-term.

I do agree with some of the advice. When you join an early stage startup, it’s probably not worth fixating too much on your specific title or role. The reality is that, especially if the company is moving quickly, things are bound to change.

What’s most important, however, is putting yourself in the right opportunity. And more specifically, the right opportunity for you.

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As someone thinking about what’s next, it is easy to get swept up by the headlines. Nowadays especially, it feels like every week there’s a new promising startup poised to (or at least claiming to) change the world.

How should you choose?

That’s the question we receive every week from people as they search for their next job opportunity.

There are lots of options (you can find many here!). But they would like help filtering out the signal from the noise. They want to find the best company, and perhaps even more importantly, they want to find the best company for them.

While I don’t have a crystal ball, in this essay I hope to give you some useful frameworks and ideas you can use to help you choose your next opportunity. I’ll try to focus on surfacing more of the unique and underrated things—things you maybe have not heard before—that I would explore doing to increase your odds of landing the right fit.

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When you are searching for a job opportunity, I find it helpful to get into the mindset of an investor.

You are in a very similar position to a venture capitalist. In a sea of options, you want to attract and choose the right opportunity.

There are some differences, though. One is that you have different success criteria. An investor may just want to make money. You perhaps want to make money but also have considerations like: impact, fun, learning, etc.

Another distinction is that you are investing your time, not just money. This leads to an important difference: investors are able to diversify their money across lots of investments. Because you can only really work at one company at a time, you won’t be able to do the same. You have to “concentrate” your bet.

That’s even more of a reason for you to take this search at least as seriously as an investor would. To do that, I suggest increasing the amount of rigor you are using to figure out the right opportunity (importantly, for you).

So many job-seekers simply read headlines and assume companies are doing really great and a good fit. It’s easy to be fooled by headlines with big numbers.

A simple way to avoid that is to get more organized and make your thoughts more explicit. Getting more organized means creating a simple tracker to aid your search.

I recommend something lightweight: an Apple notes page or a Google sheet or document. You could try something more rigid but it’s hard to make it sufficiently flexible. I would put at least two sections in your notes.

The first is a running list of all of the opportunities you are looking at. There, I’d simply write the name of an opportunity and add any notes next to it that you find relevant. Particularly try to answer the question of “What makes this opportunity interesting?” Imagine you’re doing due diligence on a startup investment, because in many ways that’s what you are doing, what would you think to put in the strengths/weaknesses/risks section for each opportunity.

The second section I’d put in my notes is a running description of what I’m interested in and looking for. I would answer questions for myself like: “What is important to me about joining a company?” “What type of compensation am I looking for?” “What types of people do I want to work with?”

You may think you know the answers to these questions but you may be surprised. Writing things out explicitly helps you see your answers for what they really are, and helps you look at them more objectively.

Both sections of your notes can (and probably should!) evolve over time as you learn more. What you’ll find, or at least what lots of people find when they do this, is a few things:

• One is that they are not casting wide enough of a net. They are only really seriously looking at a few opportunities and somehow expecting to find gold. I suggest you expand your search further than you think. (If you are looking for inspiration or lists of companies, be sure to check out Next Play, where we share loads of interesting new roles)

• Another is that the depth of their answers, across both sections, is really lacking. For example, if the reason you find a company exciting is simply “because they have good investors” what that means is you’re outsourcing the vetting to VCs. There’s a problem with this approach: investors are only expecting a small fraction of their investments to actually pan out. That expectation is baked into their investment methodology. Their fund only returns profit because it’s a portfolio composed of risk-adjusted bets. Because you’re not building a portfolio, and can only really make one bet at a time, you’ll likely need a different set of criteria for things to pan out.

To improve the depth of your logic, I would encourage you to collect more information. You can do this by Googling around and talking to people (at or around the companies you are looking at). You can talk to the company’s investors. You can talk to the company’s customers. You can talk to current employees. You can also talk to former employees.

It’s common for startups to ask you for references. I would encourage you to do the same.

Remember that you are vetting them just as much as they are vetting you. You are about to dedicate your life to this thing! It’s worth collecting information to inform your decision.

You can try to get a better understanding of where the company may be going. I would ask yourself, do you actually understand what’s going on with this company? What is the equation of their business? What does success actually look like? Where are they on that journey today? And, importantly, what’s stopping them from getting there? What are the biggest risks to the company’s success? What needs to go right? And how likely is that?

You can try to better understand the product. You can actually use the product. You can sign up for it, try to break it, and try to understand how it fits into the life of their customers. You can talk to their customers. Ask them what they like. What they don’t like. You can get a feeling to see if the company has product-market fit, or not. Would the customers be upset if the product no longer existed? Or would it not really make a difference? What are the alternatives to the product? You can also sign up for those and try to compare them.

You could also try to get a better understanding of the people. Are these the types of people you trust? Are they people you’d like to spend time with and work with? Can you learn from them? Are they good at their jobs? What makes them good? Has anyone left the company by choice? Why did they leave? What are the types of people that are a good fit for the company and what are the types of people that are a bad fit? If they were not working at this company, what would they be doing with their lives?

I would spend extra time trying to understand the CEO and/or your hiring manager. These people will be particularly influential in your job experience.

You can ask for a reverse-sell. Get them to tell you why you shouldn’t join the company. What types of people are not the right fit? If you were going to imagine this not working out, what is the most likely reason? What are all of the most likely reasons the company may fail? What are all of the reasons you may fail? If there are no good reasons, well you may have struck gold…or you may be misunderstanding the situation greatly.

With all of this, it is important to not lose sight of your feelings. Many of the above questions are quite rigid in nature. They may come across a bit machine-like. That’s not to say these details are more important than how you simply emotionally feel about the company. They are just meant to be additional information. Information that can sometimes ground your feelings in reality. Because it’s often the case that your feelings can be heavily influenced by momentum. And momentum, as we know, rarely lasts forever.

That being said, I’d also spend time sitting with your feelings. I know that sounds a bit fluffy. But sit with them. When you wake up in the morning, and you envision yourself actually working at a particular company or with these particular people, how do you feel? Are you excited? Does something feel off and too good to be true? How you feel and the emerging vibes can tell a big story.

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You may be wondering how you can practically answer all of these questions (not to mention questions about things like compensation which can also be quite complicated!). Investors have armies of analysts helping them get answers. What are you supposed to do?

It’s a reasonable question but I don’t think it’s actually as hard as it sounds. I think you can get these answers in just a few conversations with the company. I think you can be direct with them that while you’re potentially very excited by the opportunity, you’re just trying to understand how they see the world and collect information so you can make a long-term decision.

I think companies appreciate thoughtful candidates more than you may think. Would you rather hire someone who is about to be fully invested in the company or hire someone who maintains lots of skepticism? So many startup employees hop around without ever really planting roots at a single company. I think one reason for this is that people never really take the time to understand what they’re betting on when they join a company. They just sign up thinking that it’ll work out. Sometimes it does. Sometimes things are just up and to the right. Sometimes…it’s just a rocketship and you can hop on.

But I find that situation to be quite rare. Startups are rollercoaster-like journeys. There are ups and downs. You are not always sure things are going to work out.

In those moments, you’ll be very very happy you took the extra time to make a wise decision.

And if you need any help making that decision,

• Feel free to send us an email: hi@nextplay.so.

• Check out Friends of Next Play. When you join, you’ll be invited to a private slack community of like-minded people who can give you feedback on your job search.