How to survive co-founding a company with a friend

By Hayden Williams , written on July 14, 2013

From The News Desk

This is the second in a PandoDaily weekly series that chronicles the experiences of a young entrepreneur as he bootstraps his startup. Read part 1,  "The less-than-glamorous life of a young entrepreneur," and come back next Sunday to read the 3rd installment.

My co-founder and I were bickering about an obscure coding issue. The details are unimportant. Nevertheless, it would've been a standard co-founder disagreement if it weren't followed by, “Screw it. I’m sleeping on the couch.”

A “sleep on the couch” threat is typically reserved for spouses, but I can confirm that it’s also effective when delivered by an upset co-founder with whom you share a bedroom. You've heard the old axiom that when you start a business with someone you marry that person. The comparison seems especially apt for our situation. Look no further than our Verizon Wireless family plan bill.

So what caused my pissed off co-founder/CTO Paul Osetinsky to dismount from the top bunk in favor of our grimy pleather couch? The wheels were set in motion months earlier when I had broken the first rule of co-founder fight club: the worst way to deal with an imminent argument is to avoid it.

In our current beta version of Treatings individuals can propose informational meetings over coffee with fellow members whose work interests them. As many problems as our site has, it’s much improved from the alpha we launched last year, which was essentially a Wordpress site listing individuals offering a single informational meeting that other people could request. We learned a lot from that first release, particularly about what people did not want, but it was a pain in the ass to run.

We spent much our time manually listing individuals interested in offering meetings and writing notification emails that appeared to be automated but were anything but. Paul started thinking about a scalable and self-sustaining beta version. When he said he was going to shift his focus, all I heard was that I was going to be left herding cats to our prototype alone. When it appeared as though a confrontation was looming, about where our time was best spent, I stiff-armed it and we retreated to our respective silos.

Of course the conflict didn’t just disappear. Like a volcano, subterranean pressure built, and what happens when there’s no valve to release that pressure?

The eruption:

“Hayden, you don’t understand. We need to focus on the beta. We’ve squeezed all the value out of this shitty prototype and we should shut it down immediately.”

We had fallen into the trap of arguing over positions, losing sight of our true objectives. In my mind there were two options: Paul helps me prop up the prototype or I’m left to do it alone. Neither of us wanted to lose face by conceding to the other. Since I really didn’t want a big confrontation, we muddled on for a time before I understood that there was a third option – unplug the alpha – that Paul actually wanted. We finally did and Paul dove into building the beta while I focused on talking to members about what they’d want in the next iteration. But it cost us a few weeks of time.

What complicates (and, I’d argue, also strengthens) our professional relationship is that we are friends first, business partners second. The tricky part is disentangling these disparate relationships in our daily lives. We used to give each other the standard grief that friends do. Since it can be misinterpreted as passive aggression sprouting from something related to the business, we had to stop.

Case in point: the process of procuring our bunk bed. No Ikea shopping spree for us. Instead, Paul found someone on Craigslist who could build one to fit the dimensions of our room. Into our apartment bounds an energetic woman around our age, running pine trees up our stairs and electric tools I didn’t know existed. Impressed and emasculated, we hunkered down in the living room while she erected this tower of terror. When we walked into the room to check out the finished product, we realized the top bunk bed was a foot away from the ceiling, essentially turning it into an elevated coffin with a permanently closed lid.

This was much to my dismay as I had volunteered to start out on the top bunk. I chided him for not specifying the bed's dimensions (which it turns out he had). In a social context he would have laughed it off or shot back with a retort. This time, though, he got defensive, likely wondering whether I was making a broader comment about a lack of attention to detail. In hindsight, I agree that one of us should have donned our hardhats and acted as foreman during the construction process. After all, there isn’t a Kyoto Protocol equivalent for international adult bunk bed standards. Regardless, this banal story illuminate the changed dynamic in our relationship.

With Treatings and my role as a non-technical CEO, I can be guilty of meddling in Paul’s work. At this stage, as a team of two, the typical build process looks something like this: We agree on site changes we want to make > I draw out relevant wireframes > Paul takes over and codes. When Paul is coding, it’s a bit of a black box for me. I don’t know how long things take, and the prioritization of what I’m working on often depends on his timeline.

My tapping him on the shoulder to ask how code is coming along is like the annoying road trip “Are we there yet?” question. His typical response, “Dude, I can’t get it done if you’re constantly asking me about it. I’ll keep you updated.”

Besides bugging Paul when he’s in the middle of coding, another thing that makes him want to throw an iPad at my head Oddjob-style is when a single meeting or conversation I have with someone makes me want to abruptly change direction, the dreaded mission creep you hear about. I’m easily excitable, and when I get an idea in my head I can get over my skis. For example, last year I met with a company to request feedback on a tool we envisioned to help businesses engage with the outside community. The person I spoke with said that what she’d really be interested in was a tool to build their internal community. Just hearing a company say they wanted something we were technically capable of building whipped me into such a frenzy that by the end of the meeting, you would have thought this was the original idea I’d come in pitching.

Fast forward to me coming back to our office (the NYU Library) to report the exciting news to Paul. As he’s hard at work on what we’d been talking about for weeks, he hears the foreboding heel-to-sandal thunderclaps as I speed-walk over. I whisper that I have great news and we should go out and talk in the hallway. Only the stares from irritated students can contain me, but when we get outside I tell him about this new tool we had to build.

Cue Exorcist head spins.

Paul doesn’t know where to start, the fact that we shouldn’t be building a tailored tool that may only appeal to a few potential customers, or that even if we did it’s not as simple as I’m making it out to be. This is another area where my lack of technical background is a problem. I often underestimate how long it can take to change certain things, especially when it appears to be repurposing existing code. I’ve come to realize it’s like approaching an engineer who’s putting the finishing touches on a bridge and saying, “Just one last thing. I love everything as is, but let’s just make it a drawbridge.”

I’d like to think I’ve gotten better at keeping myself in check, but you’d have to ask Paul whether that’s true. In general, we try to be disciplined about airing concerns as soon as they come up, as smaller disagreements are better now than seismic explosions later.

This has led to many constructive conversations and a much healthier conflict resolution process with my nemesis, er, I mean business partner.