Choose Your Co-Founder Wisely
Decisions, decisions
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My co-founder Tom and I have been working on Upside for about a year and a half now. That being said, we’ve known each other for over fourteen years. In an interesting twist of fate, my wife found this post buried deep within my Facebook feed:
(We were a few years off, but it still trips me out that it actually happened!)
Fast-forward to today. In the last year, we’ve started a company, raised a F&F round, joined a fintech accelerator, moved to St. Louis, opened an office in San Francisco and pivoted to a new enterprise strategy. We’ve also had huge ups and downs as any early-stage startup experiences, and have the scars to prove it. My scars are due to bad knife skills in the kitchen, but whatever.
In any case, as any entrepreneur would attest to, having the right co-founder is probably the most important thing in starting a company. This has been absolutely true for me personally, and I’d thought I’d share my own reasons why:
Disagreements are not personal. Disagreements happen all the time in startups, particularly between co-founders. Whether it’s the color of a button, marketing budgets or equity stakes, there are plenty of things to argue over.
Since Tom and I have known each other for a while, we tend to give each other the benefit of the doubt and try to make sure it’s never personal. Even if things get heated and people need to cool off, we try really hard to talk it through and “hug it out” so that there’s no pent-up or buried anger or resentment that could fester or explode later on.
I’ve heard so many stories about co-founders “breaking up” due to any number of reasons that I’m really thankful that I can have a healthy debate about something and not worry that tomorrow things between my co-founder are totally FUBARed.
Establishing a trust baseline. I’m lucky to have started a company with someone I’ve known for a long time and can really trust. I have faith that when Tom is in a meeting representing both of us, that he will make a decision that we can both stand behind, or trust that he’ll wait to speak with me before committing to anything binding if he’s unsure.
More importantly, because we’ve built this friendship over a longer period of time, mistakes or bad decisions that could really hurt a new co-founder relationship tend to bounce off of us pretty easily. Whenever something happens that gives me pause or I start to question whether there were ulterior motives involved, I just step back and remember that this is someone I trust almost anything with!
Circadian rhythms. Startups are hard. Really, really, super hard. Every success or failure is amplified, and the whole “roller coaster” ride analogy is spot-on. There isn’t a day where something is either awesome or fucked, sometimes literally within minutes of each other.
You feel like you’re on top of the world because you just signed an important distribution deal!
You just got donkey-kicked in the nuts because you just found out that your critical regulatory filing is going to be delayed, again! FOR THE THIRD TIME! (True story.)
It’s important to know your co-founder’s mental state so that you can bring him down to earth (“Yes, that deal is awesome, but we still have a ton of work to do.”) or offer words of encouragement when he feels like the world is closing in on him (“Don’t worry man, we still have options, and we can keep working on the product while we wait for approval.”)
The thing is, the longer you work with someone, the more your highs and lows are synchronized. In our case, whenever I’m down, Tom is there to pick up my spirits, or vice versa. We’ve never been in a situation where we’re both hardcore in the doldrums, and that’s been the trick for us to push through when things are tough, or not spiral out of control when we receive some awesome news.
Matching style. As you can probably tell by the photo, Tom and I have hilariously similar style when it comes to dressing up, and it’s only gotten worse over time. When we go to important meetings, we have to check with each other to make sure we’re not planning on wearing the same electric blue or Nantucket red pants. Seriously.
But, more importantly, our management and leadership styles work really well together. Tom is the hard-charging, results-oriented one while I am more consensus-driven and people-oriented, but we are both about getting shit done and pushing forward, and that yin-and-yang dynamic has definitely shaped the culture of our company and how we make decisions as a team.
It’s no joke that co-founder relationships are like marriages. You have to work at it, little things end up driving you insane, and inevitably there can be some epic fights—but picking the wrong person is a thousand times worse: you’re ultimately doomed to fail.
In my case, I found someone that I had a pre-existing friendship with, and that became a foundation that weathered the storms of starting a company together. It’s not necessarily a must-have that you’re close friends, but having someone you know, who is a known quantity, will really go a long way in trusting one another and being productive as a founding team.
