Finding your cofounder
“It takes two to make a thing go right”. — Rob Base & DJ EZ Rock
Whenever I’m on a panel, inevitably I get asked the question “how did you find your cofounder?”.
Given that I just went through this process for the fourth time, I thought I would put my thoughts on paper about how it happened with Brian and Wondermile. #TL;DR- Focus on why you want to build something, not just what you’re building.
First a quick backstory: I’ve had three cofounder relationships before Wondermile. Two of them ended in flames before the companies ever got off the ground (well, not literally- though one did involve a shattered laptop and a dramatic flight to an entirely other time zone, and one a conspiracy theory and national news). However, the third time proved the charm and my cofounder Christine from Fashion Project, was such a supportive, open, talented and incredible partner on what was a remarkable journey. I never could have built and scaled Fashion Project without her (shoutout to Christine Rizk! You’re amazing!).
In reflecting on what made the difference between these three relationships, it was clear to me this time around that Brian was the person I wanted to build with. Now the big question- why?
The first step to choosing a cofounder is really knowing yourself. And not just the good parts, I mean being entirely honest and raw about your strengths and weaknesses as a human and as a leader. As part of this process for me, I went back and talked with my former team and my previous investors and asked for unvarnished feedback. I’ll admit that process isn’t easy; sitting across the table and having someone tell you what you’re terrible at may not be the most fun way to spend a sunny Friday, but if you take it as a learning experience, it’s invaluable. I heard the same things over and over. I’m extremely strong on vision, can sell anyone on just about anything, and am maniacally tenacious and driven. But, what I also heard was that I don’t always know when to switch off the sales pitch, when things get hard I go inward rather than reaching out for help, and that it would be helpful to gain the perspective of someone who scaled successful teams and formed processes on a broader scale, having seen what it takes to get to the hundreds of millions in revenue mark.
With those strengths and weaknesses in mind, I made a list of people in my network or one degree away that could fill in those weaknesses and play up my strengths. I was looking for someone who was radically transparent and open with no filter to balance my sales orientation, who had a high degree of self awareness and who naturally brought people when things got hard, and who has been there and done that at comparable companies that had reached from Series B to public scale to know what it takes. That initial list for me was about 8 people deep.
Brian Kalma was one of the eight. I had known Brian for about a year and a half at this point. We were friends- had grabbed drinks and brunch and hung out a few times over tacos. The first conversation I had with him about Wondermile (at that point just an unnamed crazy idea) was markedly different than all the other conversations I had with other people on my list. We talked for almost two hours, the conversation wasn’t about the exit or the exact solution, it was around the type of company we wanted to build, how we thought about the culture, what the “why” was behind what we would be building and a very open conversation about work styles, strengths and weaknesses, communications, and values. It was magic. That was what made me want to work with Brian above anyone else.
Here’s why- building a company is really hard. There are going to be ups and downs and points of disagreement and sometimes one of you is going to be entirely on empty and the other has to pick you up and emotionally carry the weight of the company until you’re back at full. What I learned from my previous companies is that it’s not just about the experience and skills being a fit, there is also a level of trust, empathy and values alignment that is even more important. If the founders aren’t aligned, it creates tension and chaos in the company and it will never get off the ground.
On a practical level, what does that mean? Before Brian and I decided to do this together, here are some of the topics that we covered over hours and hours of conversation (and lots of drinks and tiny hotdogs).
We talked though work styles, specifically time of day and environment, open and honest discussions of our weaknesses and strengths, communication styles and emotional states, financial situations and what sort of partners and strategies we want to have in regards to raising money (or not), how we think about building a team, how important is it to both of us to always be mentioned as a team, what drives us, peak creative times, things that went wrong in our previous roles, things that went right, what areas of the business we were interested in, the broader mission, other people we would like to work with, ground rules for how we wanted to communicate with each other, ground rules on how we wanted to hire, how we wanted our team to feel, and how above all we wanted to create a place the team and our customers loved.
You’ll notice that almost all of those are related to optimizing how we work together and how we relate to others on the team, not about the specifics of the business. This is vitally important- what you are building is going to change throughout the course of the company, but how you build it and why you’re building stays constant. If you choose a cofounder based on the what only, you run the risk of that relationship falling apart if the business changes, but if you are aligned on how you’re working together to build the company and why you want it to be built, then the foundation stays solid even if what is built on top of it shifts.
From those conversations, it was clear that Brian and I would be an incredible force together and build an extremely solid foundation of something remarkable. We kept talking, and weeks later, after exchanging lots of words and puppy gifs, we made it official.
I’m so excited to be on this journey with him and the rest of the Wondermile team. Great things are to come!
Anna
