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Hey, I’m Tim! ☕

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Help! My Cofounder is an Asshole!

This is part four of my 5-part series called “Help! My Cofounder is __________!”

• Edition 1: Help! My Cofounder is Lazy!

• Edition 2: Help! My Cofounder is a Narcissist!

• Edition 3: Help! My Cofounder is Paranoid!

• Edition 4: Help! My Cofounder is an Asshole! → This Post

• Edition 5: Help! My Cofounder is a Diva!

Always thinks they’re right. Steamrolls, bulldozes. Rules through fear. Toxic, ego-driven, zero empathy. Weaponizes criticism. Values control over collaboration.

Sound familiar?

Most toxic dynamics stem from fear: fear of failure, fear of being exposed, fear of losing control. Assholes are different.

Winning isn’t enough. They need others to lose.

The best move is learning how to spot them early and steering clear because they’re really good at hiding it in the beginning.

If you’re stuck with one, it’s usually because they hold the keys to something critical — code, capital, connections. You can’t just cut them loose (yet).

People often put up with bottom 1% behavior because they’re a top 1% performer.

But you can contain the damage. Here’s how.

Behavioral Economics

Cofounders don’t become assholes overnight. They test limits, often unconsciously, to see what they can get away with. The behavior is normalized if no one pushes back.

It’s why toxic cultures emerge slowly, not suddenly.

If you don’t set boundaries early, you’ll find yourself stuck in a cycle where bad behavior escalates. This is the "normalization of deviance.”

Respond immediately and consistently. Know where the line is drawn and don't let them cross it without paying the price.

Example: Your cofounder overrides your decisions in meetings and undermines your authority in front of the team. If you ignore it, they’ll assume it’s acceptable.

"I noticed you contradicted me in front of the team earlier. If you have concerns, let’s talk privately before the next meeting so we present a united front."

This does two things:

• It sets a boundary without escalating the conflict.

• It frames the issue as a collaboration problem, not a personal attack.

If they keep doing it, escalate your response. Don’t let small infractions slide because they compound over time.

Strategic Empathy

When people feel their autonomy is threatened, they push back harder. If your cofounder is being difficult, there’s a good chance they feel cornered in some way.

Example: Your cofounder shuts down your ideas aggressively, often in a dismissive way. Instead of arguing back, try to understand their underlying motivation:

"You seem frustrated with this approach. What’s your concern?"

This does two things:

• It forces them to articulate their resistance rather than just blocking you.

• It gives them a sense of control, lowering their defensiveness.

If you want someone to change their behavior, the worst thing you can do is trigger their identity defense system. Instead, make them feel heard first.

Use Reciprocity

Most asshole behavior is a function of incentives. If your cofounder sees you as an obstacle rather than an asset, they’ll act accordingly. Flip the incentives in your favor.

When you do something for someone, they feel an obligation to return the favor. Use this to make an adversarial cofounder more cooperative.

Example: Your cofounder always pushes their own priorities while ignoring yours. Instead of fighting for space, proactively support one of their initiatives:

"I think your plan for the new product roadmap is strong. How can I help make sure it happens?"

This does two things:

• Fosters goodwill and encourages them to return the favor.

• Creates a collaborative dynamic, from adversarial to mutually supportive.

Once you’ve genuinely done something meaningful for them, they’ll feel a subtle pressure to reciprocate. It won’t change everything overnight, but it shifts the dynamic.

Isolate Their Behavior

Asshole cofounders thrive when they think they have power over you. The simplest way to break that power is to make it clear that others don’t support their behavior.

Humans are wired for social proof. We take cues from the people around us. They think they can get away with treating you poorly because no one else pushes back.

But if they start sensing that the team doesn’t support them, they’ll adjust.

Example: Your cofounder dismisses your ideas in meetings. Instead of confronting them one-on-one (which can be dismissed as personal bias), you subtly rally support:

"I was talking with Sarah and James earlier, and we all thought this approach made sense."

This does two things:

• Publicly isolates toxic behavior and makes them face social consequences.

• Aligns the team behind a common standard of respect and collaboration.

Now, your cofounder isn’t just disagreeing with you, they’re going against the group. This makes it harder for them to act like the smartest person in the room.

Plan Your Exit Before You Need It

The hardest truth about dealing with an asshole cofounder is sometimes, they won’t change. If you’ve tried everything and they’re still toxic, you need a way out.

One of the biggest mistakes cofounders make is waiting too long to prepare an exit strategy. The best time to secure leverage is before you’re in a crisis.

Example: If your cofounder refuses to work collaboratively and actively sabotages the business, you should already have:

• A clear understanding of your equity position and legal rights.

• A strong relationship with key investors or board members.

• A backup plan for what happens if you need to leave or force a split.

Read this post about the Shotgun Clause for buying out shares.

That’s all for now,

Tim He

PS: my friend Aidan built Aftercare (YC W24), an AI-powered survey builder that saves you time and delivers deeper insights through followups. Generate a survey for free.

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