I’m incredibly lucky to get to work with so many people that I consider friends. When you enjoy the company of your coworkers and collaborators, it makes going to the office or seeing them at conferences not just work, but a joy. I believe that your success in business depends largely on what other people think of you, so working with a group of friends makes success all that much more likely.

Practically every time I’ve decided to start a company, or join a fledgling startup, it’s been with friends. Partnering with friends can be a real accelerant to your company. You already have trust and common interests — you’re friends for a reason, right? So you can get right to the business of making your company go and skip the early getting-to-know-you phase, which can be awkward when dealing with relative strangers.

Even with those benefits, I’ve sworn off starting companies with friends at least once per startup. If you don’t know your co-founders super well, not just as friends, but also as business-people, then you’re in for surprises. And if you don’t have clearly set and agree-on boundaries for the two relationships (the friendship and the business partnership), you’re in for hurt feelings and worse. Conflict at work can cross over and become conflict at home or among your larger circle of friends, and no one wants that on top of the real stress of starting a business.

The big downside to partnering with friends is that a friendship is an informal relationship, and when combined with the dorm-room-like culture that often surrounds startups and game studios, it’s difficult to have the formal business conversations that your business will require. How do you decide which friend is ultimately the boss? How do you decide how to divide ownership? How do you talk about cashflow problems when you’re emotionally invested in your partners and their families’ well-being?

These types of hard conversations are frankly easier to have in a brand new relationship — one established around a mutual interest in business instead of a several-year-old friendship. If you and a stranger decide to go your separate ways, that’s no big deal. There’s not a friendship hanging in the balance. But if you and a best friend get into a business dispute, it can be a gut-wrenching experience for you, your families, and everyone that surrounds you.

So I strongly recommend you only start a company with someone you’ve previously worked closely with before. Someone that you’ve seen deal with stress and pressure. I know I can have different modes. If you only know me socially, you may be surprised when I switch into let’s-get-shit-done mode. And if you only know me from work, you may be surprised to see me engage chill-all-the-way-out mode. You need to have seen your partners in both modes.

An even better scenario is if you’ve been through crazy work or personal crises together. Like the once a year OMG-the-world-is-on-fire-and-we-have-to-fix-this-shit-right-now type of crises. If you are still friends and still willing to work together, that’s a great sign. This way you won’t be surprised to see each other shift up and down stress gears. Everyone responds to stress differently, and there’s nothing like a startup to push the founders to emotional extremes.

At times you and your partners will have to pause your friendship and have productive business conversations in the midst of these extreme times. Setting and respecting boundaries early on in the new business will make it easier to communicate when the shit is hitting the fan. Long before there’s even a fan, decide on how you want to work, communicate, and disagree with each other. Along the way, at least once a year, check in on those boundaries to make sure that you’re all still on the same page.

When it comes time for difficult work conversations between friends, I try to lead with professional, and say “I need to talk with you as your business partner” or something a little less serious like “I need to talk with you as the boss for a minute.” This sets the tone and lets us talk about serious sensitive stuff in a way that hits less personally, and makes it easier to reach for something other than pure emotion when responding. It’s very sobering to hear “if we don’t [do this thing] we’ll go out of business.” Hopefully you don’t have to have that conversation too often, but it will come up more than once.

On the flip side, one of the benefits of having friends for business partners is that the absolutely hardest conversations still require a strong personal connection. A couple times in my career I’ve been in the difficult position of turning down money for ethical or emotional reasons. All I could say to my partners was “you know me, you know that I’m not personally OK with [this thing], and I really want my life to be about something different.” I was lucky to have partners and friends that cared about me, and we were able to work out solutions that we could all live with.

But no matter what, it’s a challenge. The friendship and the business partnership are disctinct relationships, that need care and tending. I’ve sworn off working with friends, but I’ll keep doing it. You end up spending tons of time with your business partners — at the office, at events, and on the road together. I don’t think I could stand only dealing with coworkers and collaborators in a cold, sterile business-only way. That doesn’t mean we can’t switch into “bizness mode” for real talk. But we get to eat, laugh, cry, high-five, and fist-bump along the way.

When you’re deciding who to partner with, look for friends that you trust, that have helped you triumph in stressful times, and that you’re willing to share every little bump in the road with. If you can’t trust your friends and business partners to lift you up when you get knocked down, then they shouldn’t be your friends or your business partners.

See y’all next week. Play nice!
Patrick

P.S. Sorry for missing a week. I’ve had a couple busy weeks on the road. Thanks to the friends that made it possible & bearable! Also, this is me: