How to build a founding team for your company

This post was written in collaboration with our friends at Next Play.

In the early days of Dropbox, co-founder Drew Houston asked one of his early investors for advice about building a startup. In response, the investor sent a 10-item list:

1. Hire the best people
2. Hire the best people
3. Hire the best people
4. Hire the best people

[...]

It’s great advice that is exponentially more important if you haven’t actually hired anyone yet. Brian Chesky (co-founder of Airbnb) described hiring the company’s first engineer like bringing DNA into their company: “If we hire this person, there [are] going to be a thousand people just like him or her in the company.”

Building a founding team is hard because company-building, including hiring, is hard. And partly it’s hard because there are things that are true about hiring for a founding team that may not apply across the rest of hiring. So perhaps the most useful way to begin thinking about how to hire your founding team is by establishing some general framing.

Fundamentally, hiring people for your founding team should be a win-win. In theory, this is true across all hiring, but it’s especially important when you’re hiring a founding team. You should be honest — you need to find people who actually want to do this crazy thing you’re pitching them, not people you are tricking into joining your risky startup as opposed to getting a well-paid job at a stable company.

And you should know what you’re looking for:

• You’re looking for persistent people with high risk tolerance. 
• You may want T-shaped people. 
• You need to have an unbelievably high level of trust in them. 

To identify whether someone might be a fit for all of these things, I find that the most useful category of information is about past experiences: what have they done already? Even a 21-year old college student who’s never held a full-time job, if they are great, will have some interesting past experiences. Here are some things to look for.

• Have they owned projects from 0 to 1? And did they actually do the work?
• Have they worked with ambiguity? (3 years as PM at Google is not that ambiguous.)
• Have they had to define their own roles in the past?
• Have they founded a startup before?
• Have they worked on a founding team at a startup before?
• If so, why did/didn’t it work out?
• Have they experienced the ups and downs of a startup?
• Are they T-shaped: great at one thing but also broadly competent?
• Have they had founding team-level ownership of anything in the past?
• Have they ever produced truly great work?

You can try to answer most of these questions without even talking to the person; a sufficiently thorough search of their LinkedIn profile, personal website, and online footprint can sometimes get you most of the way there. And vetting past experiences can get you some, or most, of the way there. But you should also be interested in somebody’s mentality. The mentality you should be looking for in someone on your founding team is rarer — and more specific — than the mentality you might look for in your 500th employee. 

On this subject, people often tell you that you should hire folks with a “startup mindset.” What does that really mean, though?

• Are they at least a little bit naive? Meaning, are they optimistic and high conviction people who can see things with fresh eyes? Or are they cynical and jaded?
• Are they a complainer? Are they generally negative?
• Are they honest?
• How do they define “great”? Do they care about producing great work?
• Do they have a strong ability to learn?
• Do they actually have a passion for your customer or opportunity?
• Are they mentally tough and persistent?
• Can they be an entrepreneur (the criteria Zynga’s founder used)?

You may only be able to decide the answers to some of these questions after you’ve spent some time talking with the person. But it’s always good to have criteria before you start your search. 

Once you’ve gotten clear on what you’re looking for, you need to actually find those potentially great people who might be a fit for your team. And that’s probably going to take some looking. Some places to start:

Your network and extended network. The default path for many (and possibly most) founders is to hire people they know. Drew Houston of Dropbox said that you “start by getting your most talented friends.” Lenny Rachitsky wrote a piece on this topic and interviewed dozens of founders, many of whom basically said the same thing. Probably this is because you should have high conviction and high trust in your founding team, and it’s easier to have those things when your founding team is made up of friends you’ve had for years.

The downside though is that your friend group is nothing close to representative of the entire pool you could be hiring from. Be careful of overrating people just because you know them personally, or because someone you trust recommended them. While it’s possible that some of the best options for your founding team are in your immediate social circles, it’s unlikely that you should stop the search there before you’ve figured out if someone else is a better fit.

Next Play (and similar communities). Find places where ambitious, curious, smart people in your potential hiring pool might hang out. Next Play is a good example — multiple startups have hired founding team members they found in the community. There are a few ways you can chop this up: (1) you can join the communities (i.e., if they have a Slack or Discord) and reach out to interesting people, and/or (2) you can figure out a way to publicize your founding team search within the community, like getting featured on Next Play. You can email Next Play at [email protected].

Search in other smart places. Start from first principles (an overused phrase, but true here!) and reverse engineer where your founding team members might be hanging out. If you’re looking for a Founding Engineer, what college(s) could they have gone to? What projects would they have participated in? What forums would they be on? How would you find them? Tools like Scout can help make it easier to find interesting people and get their emails. You can also consider finding people whose equity at their current company is about to vest, who have startup experience at top companies, those who have built their own projects… There are 100s of ideas like this!

Finally, you may as well post a job. While this isn’t usually how founding teams are built, it’s not impossible that your perfect founding team members apply to a job you post somewhere, like on LinkedIn. It doesn’t hurt to expand your surface area.

What should you do once you’ve got that person in conversation? Reach out, pitch them on your idea, get to know them (founding team members often spend a lot of time together), and earnestly assess fit. I talk through that and much more in the guide, “On Building a Founding Team.” (Sign up for the Next Play newsletter to give it a read.) 

Keep in mind, there’s a reasonable chance you will make some hiring mistakes. but your real goal is to increase the probability of hiring the right person as much as you can — because hiring a great founding team will help shape your startup’s path to success.

Next Play is a community of thoughtful introductions and curated gatherings for world-class operators and founders looking for what’s next. Apply here to join the community.