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The Perfect Co-founder Checklist

The Perfect Co-founder Checklist

12 ways to tell if you’ve found The One to work with, from someone who spent 3 years looking.

In a past life, I was lucky enough to be a Director of a chapter of the Founder Institute. I ran the program here in Perth for a little over 2 years, but had to make the hard call to step back from it when I became co-founder of Appbot. Last night I attended the first event run by the new FI Directors.

They had full house of budding entrepreneurs. Over a glass of wine I chatted with about a dozen attendees at the end of the event and one theme came up over and over…

How do you find your perfect co-founder?

Finding the right co-founder is really hard to do, and as one of the few entrepreneurs I know with a really epic co-founder relationship I found myself thinking about it throughout the rest of the evening. As our company, Appbot, has been growing I have been really feeling the true value of working with Stu. We’ve got each others’ backs, and stressful as it all is, it’s amazing fun too.

Last night I was reminded how rare this is… Had I stacked the deck in my favour somehow in order to partner with Stu on Appbot? Was it just amazing luck? Could I figure out any replicable things that other founders could try, in order to improve their own odds of finding the best person to work with? Given that I now have that glorious thing, 20/20 hindsight, how could someone else test whether their co-founder relationship was going to be awesome?

16 hours later and this post is just bubbling out of me.

I have to share it.


So here goes…

Test #1: Do you trust each other?

If the answer is anything other than an unequivocal “yes”, you should be reconsidering working with this person. You should be able to answer this question in a nanosecond. Hesitation is your enemy, gut-instinct is your friend.

Test #2: Do you laugh at each others’ jokes?

Startups are hard, even when they’re easy. There will be days where you feel overwhelmed, exhausted, confused, lost or demoralised, and on those days laughter is your bestie, believe me. Being able to lighten the mood for each other is, IMHO, an invaluable trait.

Test #3: Do you have BIG respect for their previous work?

This isn’t just about the work itself, although that’s important. What did the people that worked with them previously think about working with your co-founder? Try to focus on non-verbal queues here — when your co-founder came up in conversation with people who’ve worked with him or her before, did the commentary feel warm and respectful? There’s a lot of temptation to focus on what the other person can do but HOW they did it, in the interpersonal sense, is probably more important if you’re going to have a really positive co-founder relationship.

Test #4: How do you compare on risk aversion?

If you’re a mid-spectrum kind of person, you probably want to find a co-founder who is similar. If, like me, you’re relatively comfortable with risk, I recommend working with a co-founder who is more conservative and vice versa. Stu and I balance each other really well on risk, and it gives me multiples of confidence that we make better decisions together.

Test #5: Are your personal situations similar?

This test is about empathy; about being able to understand each others’ personal challenges, strengths, priorities. Personally, I reckon having a co-founder whose personal relationship is in good shape is pretty important — happiness at home is contagious, and in my experience the reverse can also be true. If kids are part of the picture for you, having a co-founder who also has those kinds of responsibilities is really awesome (and provides a heap of solid material for point #2 ☺ ).

Test #6: Are your skills complementary?

Being awesome at really diverse stuff is a big advantage — if you each have different strengths your company will thrive on multiple fronts and you’ll be happy working on different aspects of the business simultaneously. That’s not to say you can’t both love some of the same stuff, just not ALL the same stuff. Make sure you know what kinds of things your co-founder procrastinates over, and check that list against your own. Overlaps on the “stuff I put off” list are best avoided.

Test #7: How does your co-founder cope with stress?

Arguably the hardest thing to make a judgement on when you first start to work with someone, but a factor you can’t afford to ignore. In situations where you don’t have first-hand experience of your co-founder under stress, think about whether you know anything about how they’ve handled really stressful stuff in the past — war stories they’ve shared, or personal stories. Past colleagues often give you clues about this too.

Test #8: Are you like-minded on big issues like employee equity, fundraising and exit strategy?

When Stu and I decided to work together we talked about these issues and many others to see if there was any area where we had a major disconnect. These big philosophical points don’t “just work themselves out”, and they have the potential to derail your working relationship and therefore your company if you really, deeply disagree on them. If you’re raising money or negotiating an exit you’ll be stressed, overworked, and not in a position to focus on working these things through, so make it a priority at the beginning.

Test #9: What are the lines of communication like when you disagree?

I think communicating in the face of disagreement is something very personal. Basically, you need to be able to do this without upsetting or offending each other, and my take is that having a similar communication style makes that more likely. I think that the first point about trust also relates to how your disagreements play out; if you have a high level of confidence in the other person it will make it easier to trust in the absolute validity of the other person’s point of view, and go with their preference over your own when you need to. It also means you move on quickly, and trust me, you’ll be too busy to want to dwell on anything too long!

Test #10: How do you each feel about documenting your working relationship?

A willingness to write stuff down is not to be underestimated. After all, if you plan to behave honourably towards the other person, why wouldn’t you be happy to have that documented? Steer clear of “gentlemen’s agreements” (urgh, so sexist!) and “handshake” arrangements. Personally, I’ve found those things to be code for “non-commitments” ☺

Test #11: Are you equally passionate about the product?

Startups exist to solve problems, usually complex ones, in new ways. If you’re going to solve a difficult problem together, you’d best be passionate about the subject matter.

Test #12: What’s the vibe like when you work together?

Deciding to become someone’s co-founder is a massive call. Like getting married, in a lot of (way less romantic) ways. Becoming a co-founder deserves a test-drive, at least. Working together for even just a few days will not only give you insight into the other person’s work ethic and how productive you are together, but it’ll help you get a gut feel for whether you have a good time hanging out. If you feel like you’re making better decisions by working together, consider it a really good sign. If you really look forward to going to grab some lunch and chatting, even better. Enjoying each other’s company is key, you’re gonna be spending a lot of hours together.

What if you’re struggling to find this mythical creature, the Perfect Co-founder?

Clearly, it’s not so easily done. If it were, organisations like Founder Dating just wouldn’t exist. Being a digital marketer, you won’t be surprised to hear that I think finding your ideal co-founder is a numbers game. I’ve got two pieces of advice to offer here…

Firstly, meet as many people as you can, and don’t expect meeting the right co-founder to happen quickly. It took me 3 years, and I know many who have taken longer. Hang out with people who know a lot of people. Go to tech events (and enjoy this bit while it lasts — once you’re head down on your startup you’ll probably be too focussed to maintain the same level of involvement), do some Startup Weekends, and keep half an eye on social media.

Secondly, look for opportunities to lead something, anything, in your local startup ecosystem. Taking a visible lead on a project makes it more likely that smart, motivated, experienced people will seek you out, and that makes the first point a lot easier. For me, running a chapter of The Founder Institute in a city with a small, nascent entrepreneurial community made all the difference. I didn’t meet Stu directly through Founder Institute, but I did meet the person that introduced us that way.

So that’s it — I feel lighter!

Thanks to @stuartkhall for being my co-founding muse, as it were. Thanks also to those Founder Institute attendees last night for the inspiration.

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