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Hey, I’m Tim! ☕

Every Mon and Fri, I help you become the cofounder your startup deserves.

• Actionable advice: Practical tips you can put into use today.

• Relatable stories: Real-life experiences from people just like you.

• Unique insights: Fresh perspectives that you won’t find anywhere else.

Cherrytree is the blueprint for building your dream cofoundership.

PS — If you really want to answer the unGoogleable questions, book time with me for free. I’ve coached dozens of pre-seed/seed stage cofounders.

Help! My Cofounder is a Diva!

This is part five 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!

• Edition 5: Help! My Cofounder is a Diva! → This Post

High-maintenance. Temperamental, drama queen. Entitled. Flaky. Self-important, uncoachable, unmanageable. "I don’t do grunt work."

Sound familiar?

If your cofounder is a diva, they’re difficult to please and behave as if they’re super special or important. More focused on how things look rather than how they work.

The best startup teams, like Aftercare (AI-powered survey builder with follow-ups), have a ‘get shit done’ mindset. A high-maintenance cofounder is the opposite of that.

Reframe Their Ego as a Resource

Most people try to suppress a diva cofounder’s ego, but that’s a mistake. Instead, harness it—make their success dependent on the startup’s success.

Social psychologists know that people with fragile high self-esteem need external validation. If they see the company as an extension of themselves, they’ll fight for it. If they see it as a threat to their personal brand, they’ll sabotage it.

Example: Your cofounder craves public recognition and dismisses unglamorous work. Instead of fighting this, frame key decisions around their status:

"You should take the lead on this pitch. Investors will see you as a visionary if you set the direction."

This does two things:

1. Aligns their ego with the company’s best interests instead of against them.

2. Reduces their resistance to necessary decisions by making them feel like the protagonist.

When they believe their status is tied to the startup’s success, they become a motivated ally instead of a liability.

Force Hard Trade-Offs

Divas thrive in ambiguity, where they can demand everything without consequences. Instead of arguing over behavior, create moments where they must choose between personal status and company survival.

Behavioral economists call this "forced commitment" — when people have to make binary choices, their real priorities emerge.

Example: Your cofounder demands full hiring control but won’t delegate anything. Instead of debating, ask:

"Would you rather control every hire or build the best possible team?"

This does two things:

1. Forces them to confront the trade-offs they avoid.

2. Shifts the conversation from personal preference to what actually works.

By making them own their choices, you break the illusion that they can have everything without sacrifice.

Weaponize Their Fear of Looking Weak

Divas hate one thing more than anything else: appearing weak or incompetent. Use this to make them want to behave better.

People with narcissistic tendencies care more about how they are perceived than what’s actually right. If collaboration looks strong and stubbornness looks weak, they’ll adjust their behavior accordingly.

Example: Your cofounder refuses to delegate because they want control. Instead of arguing, frame delegation as a sign of strength:

"The best founders surround themselves with great people. If you focus on strategy, it’ll show investors you’re a true leader."

This does two things:

1. Turns good behavior into a status symbol.

2. Creates peer pressure—if they think successful founders act a certain way, they’ll follow.

Instead of fighting their nature, you redirect it in a way that benefits the company.

Exploit Their Addiction to Winning

Some founders want to be right more than they want to win. The trick is making them see adaptability as the ultimate victory.

Competitive people are wired to optimize for external success. If you frame every decision as a competition against an external enemy, you make their ego work for you.

Example: Your cofounder insists on their product vision despite clear market feedback. Instead of challenging them directly, reframe the situation:

"If we stick to this, [competitor] wins. If we pivot, we dominate the market."

This does two things:

1. Redirects their competitive drive toward external success instead of internal conflict.

2. Makes them emotionally invested in smart decisions instead of stubbornly clinging to bad ones.

When winning the market becomes the real victory, they stop trying to “win” arguments.

Set Up a Soft Exit Before You Need It

Some cofounders can be redirected. Some can’t. Either way, you need an exit strategy before things explode.

People with high entitlement rarely think they’ll be held accountable—until they are. The moment they realize they’re replaceable, they either adjust or leave.

Example: You sense that your cofounder might not be salvageable. Instead of waiting for disaster, you start preparing:

• Quietly identifying potential replacements.

• Ensuring legal agreements protect the company.

• Making it clear (subtly or directly) that they are not indispensable.

This does two things:

1. Gives you leverage—if they think you can replace them, they behave better.

2. Ensures you’re ready to move on if they won’t change.

By the time they realize what’s happening, you’ve already secured the company’s future.

That’s it for now,

Tim He

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