In partnership with

Hey, I’m Tim! ☕

Nobody’s quite sure where Friday the 13th came from.

Some say it’s from Norse mythology, where twelve gods were having a dinner party and Loki, who was not invited, arrived as the thirteenth guest and unleashed chaos.

Others point to Jesus's Last Supper, where thirteen people gathered in the Upper Room on the thirteenth of Nisan Maundy Thursday.

Whatever the origin, here are 4 unlucky ways to ruin your cofoundership.

The ‘Four Lacks’

When the dynamic is fractured by these "four lacks," you’re building on quicksand.

Nearly all the cofounder breakups I’ve seen can be attributed to one or more of these.

1. Lack of Commitment

The committed cofounder feels the weight of carrying the company. The uncommitted cofounder feels guilty yet unable or unwilling to share the load.

Resentment from both sides.

• Different levels of sacrifice: One of you works 16-hour days, while the other takes side gigs or prioritizes other work. Read about that here.

• Missed milestones: The less committed cofounder leaves tasks half-done. The committed cofounder is forced to pick up the slack.

• Lack of accountability: One of you always tries to steer the ship while the other remains detached. The more committed one ends up feeling abandoned.

2. Lack of Competency

This introduces an insidious form of strain.

Not because they can’t learn (they often can) but because incompetence amplifies dependency.

• Constant reliance: One of you has to step in to clean up after the other’s mistakes. It signals that the cofoundership isn’t operating symmetrically.

• Failure to learn from mistakes: It stems from a refusal to adapt. A cofounder who doesn’t take feedback well will inevitably cause friction.

• Loss of confidence in judgment: If one of you keeps making costly errors, even if they're well-intentioned, the other will doubt their judgment.

3. Lack of Coordination

Coordination isn’t just operational; it’s psychological.

• Conflicting decision-making: When your priorities aren’t aligned, you make contradictory decisions, even on routine matters.

• Failure to communicate in real-time: If one of you doesn’t share important information, the other feels left out and frustrated about being sidelined.

• Timing mismatches: If one of you pushes hard and the other drags their feet, you’ll be stuck in a constant tug-of-war.

4. Lack of Compassion

This is the sleeper issue, but perhaps the most damaging.

• Dismissal of personal struggles: If one of you goes through a personal crisis and the other brushes it off as a distraction, that’ll definitely damage the bond.

• Lack of support in failure: Reacting with impatience or criticism when things don’t go according to plan causes the struggling cofounder to feel isolated.

• Inability to show vulnerability: You’ll operate at an emotional distance if it’s more about who’s “right” rather than who’s in it together.

These "lacks" don’t exist in isolation; they compound on each other.

• The lack of commitment erodes trust, which leads to a lack of coordination.

• The lack of coordination further exacerbates any incompetency.

• The lack of competency triggers frustration and a breakdown of compassion.

• The lack of compassion leads to a toxic cofoundership.

But here’s the good news: the reverse is just as true.

A small improvement in any one area positively impacts all the others.

Enjoyed this? Copy your custom referral link and share Cherrytree with a friend.
^{Top referrers every month win a cash prize.}

Thanks y’all,

Tim He