Starting a company with other people is a Big Deal. Co-founder relationships must be among the most unique and rarely discussed natural phenomena of the business world: different parts colleagues, close friends, spouses, and co-parents, mixed into an exact cocktail whose measures are different for each company.
Not only are co-founder relationships unique, they are also extremely important to get right. Noam Wasserman reviewed 10,000 startups for his book The Founder’s Dilemma and found that 84% had multiple founders. And when high-potential startups failed, co-founder dynamics were to blame nearly two-thirds of the time.
Given how many things could go wrong, I feel truly lucky to have started Shortlist with such great co-founders, Simon and Matt. We’ve been through some crazy times, with each of our roles shifting in significant ways since we started. We have worked together through two funding rounds, team members leaving at critical times, amazing new people joining, major contracts getting won (and sometimes lost), and all of the other ups and downs that make startup years feel like dog years. And now I’ve got all the grey hairs to show for it.
To complicate things further (and I’m not sure I would recommend this to everybody!), Simon and I are flatmates in not one but two different cities as we manage our three offices across two continents — just to up the stakes that much more.
Through it all, the three of us have maintained a pretty darn special relationship. This is what we’ve found works for us to keep things stable, productive, and fun.
Build from the “why”
Before we started the company, we invested significant time journaling and discussing our respective answers to the question, “Why Shortlist?” This of course touches on very big picture “Why” questions like purpose and mission (“unlocking global professional potential!”) but also the more banal but equally honest reasons like trying to stretch personally, making money, and having a great time working with great friends. At our annual co-founder retreats (more on that below), we nearly always start with a “Why” refresh and check-in on if and how the “Why” might be changing.
Make culture and values primary
Early on, we spent a lot of time working to clarify the bedrock ideas on which to build our team on – the Shortlist core values. We’ve written elsewhere about our efforts to document and evolve these values, but it’s important to recognize that we also use these to drive our own interactions and relationships. When we’re giving each other feedback, solving problems, or looking for a tie-breaker, we will often fall back on our values to shed light on the best way forward.
Always get to empty
Another important principle for us is to never leave things unsaid. Particularly when we’re giving feedback, talking about tough topics, or asking each other for help, we have a principle (coined brilliantly by Matt) that we should “get to empty.” That is, nothing should be left in the “tank,” no additional points you wish you had made as you reflect a day or a week later. One of the ways to accomplish this is to simply listen and at the end, pause, repeat back what you heard, and ask “Is there more?” This makes sure there’s never a frustration or resentment hangover, and encourages us to tackle questions and issues head-on.
Disagree and commit
Even when we disagree (and yes, we do sometimes disagree), we try our best to make the decision and then all stand behind it. Jeff Bezos talks about this idea in three words: “Disagree and commit.” We don’t have to always agree on everything, but at some point we need to make a decision and whether or not we all are convinced, we need to commit to the decision and do everything humanly possible to make it succeed. We also need to make sure the team sees us as unified co-founders, to avoid the politics and cultural deterioration that can creep in when the “bosses” don’t seem aligned.
Prioritize fun and adventure
One of the most sacred of our commitments to each other is that at least once a year, we will get away from our everyday mindsets and locales and “retreat” somewhere sufficiently adventurous to suit the co-venture of Shortlist. We’ve been to a beachfront yoga institute in Kerala (pictured), a ranch at the base of Mt. Kenya, and a condo in Cabo San Lucas, Mexico (don’t worry, all done in ways that are free or creatively cheap for the company).
This gives us some space to recharge and also to tackle some of the bigger questions facing us as a company, as friends, as people. We intersperse marathon deep dives on the strategic questions of the day with great meals, intense workouts, and a cocktail or two, and re-enter reality ready to blow the doors off the day.
Have a “keeper of the force”
With Simon and I spending nearly all of our time with our teams in Kenya and India, we often find ourselves deep in the “trees,” making the “forest” a bit hard to see. Matt’s relative distance (he’s based in California) makes it a bit easier to pull us out of the trees, remind us of the bigger picture, and keep us focused on the important (not just urgent) stuff. He’s also there to diffuse any tension when the strain of multi-city flatmating and co-founding gets too much. We’ve often reflected that Matt feels like the “keeper of the force” for the three of us — sans lightsabers. While the typical co-founders are likely all “on the ground,” you may be able to identify another senior team member or advisor who can “keep the force” for you too.
The only constant is change
Yes, startup years are dog years. Things change often and they change fast, with crazy ups and downs – often in the same day. Teams turn over naturally and unnaturally in myriad ways and business strategies and products evolve at hyperspeed. For us co-founders, that change has come in many ways, including significant role evolution for each of us, physical moves across continents (sometimes twice in the same year!), drinking from fire hydrants as we learn new industries, new functions, and new markets. I have been inspired to watch the way Matt and Simon leave ego at the door and give Shortlist whatever it needs, at any given time, to be the best version of itself.
How do other people make these special, unique co-founder relationships work? I’d love to hear from you!
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