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What If It’s Me?

ICYMI, catch up on the 5-part series: “Help! My Cofounder is _____!”

1. Help! My Cofounder is Lazy!

2. Help! My Cofounder is a Narcissist!

3. Help! My Cofounder is Paranoid!

4. Help! My Cofounder is an Asshole!

5. Help! My Cofounder is a Diva!

You love pattern recognition until the pattern is you.

You’re fast to spot flaws in others:

• “My cofounder doesn’t follow through.”

• “They’re emotionally reactive.”

• “They don’t think strategically.”

But what if you’re the problem??

The irony is that the very traits that get celebrated early:

• bias to action

• strong opinions

• high standards

quietly metastasize into dysfunction if left unchecked. Especially when projected outward, never examined inward.

Character ≠ Competence

Startups select for skills, not self-awareness.

You tell yourself:

• “I’m the visionary. They just don’t get it.”

• “I’m pushing us forward. They’re slowing us down.”

• “I’m clear. They’re difficult.”

But often:

• “Visionary” means I bulldozed.

• “Pushing forward” means I refused to listen.

• “Clear” means I didn’t leave space for dissent.

Startups don’t die because someone was wrong once. They die because two people stopped being able to hear each other.

You can be technically right AND relationally unbearable.

Cofounderships Are Emotional Algorithms

Every relationship is a loop.

One person gets anxious → becomes controlling.
The other feels controlled → withdraws.
The withdrawal makes the first more anxious → and more controlling.

Repeat.

The best cofounders interrupt these loops. They’ve learned that the cost of ego is exponential.

Power Without Reflection = Distortion

The more equity you hold, the more distorted your mirror becomes.

Your team is less likely to challenge you.
Your investors often want a smooth board call.
Your cofounder stops pushing back if it never seems to land.

Some of the best cofounders I know block out time every month to audit their own behavior.

This is how you build companies that scale without warping.

4 Questions That Change Everything

You don’t need a coach (though it helps).

You need the courage to sit with discomfort and ask:

1. What do I hate about my cofounder and what’s its shadow in me?
   “They never take feedback” → Do I?

2. If I fired myself today, what behavior would the team feel relieved about disappearing?
   You can’t ask them this but you can infer.

3. What’s the conflict I keep reliving across teams or startups?
   If it keeps happening, it’s not just them.

4. Where am I right and still doing damage?
   Being correct is not the same as being constructive.

Patterns Matter

How you behave today becomes the company’s muscle memory tomorrow.

If there’s tension, politics, silence, it didn’t start in the org chart. It started between two people who didn’t know how to be honest with each other. Or themselves.

Start with the hardest and most liberating question in a cofounder’s toolkit:

That’s all for now,

BTW — The Cherrytree cofounder community is now open. Join here →

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