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Founder Breakups

There is something particularly heartbreaking about the self-inflicted nature of founder breakups.

Two or more smart and ambitious people destroy their own creation in tragic and ugly ways. Sometimes years into their joint journey.

This can sound overdramatized until you watch a few of them up close. No juicy details will be disclosed today, but I will share the lesson I learned from watching a few breakups (and thankfully never experienced one myself).

All founder breakups happen for the same reason: the relationship breaks apart under sustained pressure.

This happens because we underestimate how differently people behave in different situations. Think about how you behave when you’re with your parents vs at work.

Now, how do most founders test their relationship?

  • Going on coffee dates

  • Talking about their goals, values, and aspirations

  • Working on a fun side project together

Coffee, talking, and working on fun stuff don’t bring out the behavior you will see at your startup.

Your startup will compress you under immense pressure over a long period of time. This will bring out a different behavior from you and your co-founders. These behaviors are those you want to be testing.

I call it founder stress-testing. Literally testing the relationship under as much stress as needed to bring those behaviors out.

There is no perfect way of doing this, but there are better ways than coffee dates.

The long way. Every real relationship goes under stressors over time. My co-founder and I have been friends and worked on side projects for years before taking the plunge. The long way takes longer, but it is the most reliable one.

The short way. Do you know that feeling when you go on a trip with friends and then on day 5 everyone’s real personality comes out and you kind of hate them? That’s what you want to do – force the under-stress-personalities to come out. Here are some ideas:

  • Trip - Go on a long trip with just the two of you. Spend as much time together with as few distractions as possible. Do this for a week and see if you ever want to see that person's face again. Bonus points for sharing a room

  • Multi-day hackathon - Work together around the clock and make it your goal to win first place, not just to have a good time

  • Physical challenge - go on a week-long trek. Make sure that it’s a bit too strenuous for both of you. When people are exhausted the masks come off

These ideas are imperfect and a bit crazy, but what’s more crazy is embarking on the hardest challenge of your life with someone you barely know.

Stress-test now. Don’t wait for the crushing force of your startup.


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