Why Jobber's founders say strangers make better co-founders

The typical startup advice is to find a co-founder you know and trust. Jobber co-founders Sam Pillar and Forrest Zeisler found an advantage in doing the opposite: Starting as strangers forced them to build trust intentionally, challenge each other’s ideas, and have difficult conversations early.

The two software developers were freelancing and often workeding out of the same coffee shop in Edmonton, Canada. What started as a casual conversation about their work turned into a deeper discussion about how to solve the same problem: helping businesses operate more efficiently.

Together, they built Jobber, a software platform they launched in 2011 that helps service businesses manage their daily operations.

“A lot of people are fooled by the connections they have outside of the work environment into thinking that that would just automatically apply into the work environment,” Zeisler said.

In a conversation with Founder Brew, Pillar and Zeisler discuss how starting as strangers shaped their partnership, the importance of productive conflict, and what foundations support the strongest co-founder relationships.

This interview has been edited for length and clarity.

You’ve said not being friends before starting Jobber was actually an advantage. What’s something that would have been harder if you’d been close friends first?

Sam Pillar: The huge value for Forrest and me was building our relationship business first. It meant that, very early on, we could have really tough conversations and debate issues in the spirit of productive conflict. If we had been friends, you might think, “I don’t want to have this tough conversation and have the friendship be weird for a couple of weeks while we process it,” and therefore we won’t have the conversation—and therefore the business doesn’t benefit.

Forrest Zeisler: A lot of the reasons that people become friends, in some ways, it short-circuits trust. But those are bad proxies for whether you’re actually going to work well together.

When you’re building with a stranger, there’s no inherited trust. How did you build that trust in the early years?

Pillar: By doing what we said we were going to do, showing up. For the first little while, it wasn’t like we had an office to go to…There was no forced system of accountability…We got up early and worked 12 hours a day, that was the schedule, because we were both really eager, committed, and excited… Going through that first year together offered all kinds of opportunities to prove to one another that we were going to step up and take this seriously…I think it’s just like reps. You need time and cycles to build trust.

What did conflict between the two of you look like early on? Was there a moment you really butted heads, and how did you work through it?

Pillar: The naming was maybe one where there was some passionate and heated debate.

One of the things I’ve learned from Forrest over the years is to temper my ego. Forrest has always been a very low ego person, which really helped in those early debates. He’s always been the first to say, “All right, yeah, that’s a good idea. I like my idea better, but that’s a pretty good idea too. Let’s try it.” I think that’s a really great characteristic.

What has this partnership taught each of you about yourselves as founders? What weaknesses did it expose?

Pillar: I can get a little bit energized, a little bit hot, and lose my anchoring a little. That was certainly a blind spot when we got started, and one I continue to work on.

Zeisler: Sam is particularly strong at people and motivation. As CEO, he has to cover the full company—1,300 people, the range of roles from sales to engineering.

I like to think of myself as empathetic, but that doesn’t automatically make me a great communicator, great at change management, or great at all the things that are important for leadership.

Do you think great co-founder relationships are discovered or built?

Zeisler: There was definitely a huge piece of luck that we ran into each other at the right coffee shop—two people who happened to see a similar problem and had shared motivations.

There needs to be the right foundation, but then it also takes work. You can’t take your marriage for granted; you can’t take a founder relationship for granted either.

Pillar: It’s both. Founder relationships are discovered in some way—the two right people need to meet, or multiple right people, however many founders there are. But there’s got to be a chemistry there.