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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 to 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 Paranoid!

This is part three 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! → This Post

• Edition 4: Help! My Cofounder is an Asshole!

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

Trusts no one. Always on edge. Interprets silence as hostility and feedback as an attack. Hidden agendas. Grudges. Sabotage. Suspicious. “I told you so.”

Sound familiar?

Paranoia thrives in uncertainty. Startups are nothing but uncertainty.

It’s subtle at first. A healthy amount is necessary, even. But your startup requires trust and a belief that everyone’s on the same team. A paranoid cofounder disrupts that.

They see threats where none exist, question loyalties, and second-guess motives until you can no longer collaborate with them. Worst of all, they create a culture of suspicion.

If your cofounder is paranoid, you can’t just tell them to “relax” or “trust more.” Instead, you have to engineer an environment where paranoia has fewer places to grow.

Clarity in Predictability

Paranoid people fixate on what they don’t know. The more gaps there are, the more they’ll fill them with worst-case scenarios. Reduce uncertainty wherever you can.

Make decisions transparent. Walk through your thought process so they don’t assume hidden or ulterior motives.

Example: Your cofounder keeps questioning why you’re making certain decisions, suspecting hidden motives. Instead of dismissing them, think out loud with them:

"Here’s why I think this is the best move. If you see a flaw, let’s work through it together."

This does two things:

1. Prevents worst-case assumptions from filling in the blanks.

2. Builds trust by making them feel included rather than excluded.

If they know exactly what’s going on, there’s less room for suspicion to grow.

Aftercare can help you with that from a user standpoint. It’s perfect for gathering product feedback, measuring satisfaction at an event, conducting market research, etc.

Defuse, Don’t Dismiss

Telling a paranoid cofounder "that’s ridiculous" will only make them dig in harder. Instead, acknowledge their concerns while subtly reframing them.

People cling to fears because admitting they’re wrong feels too painful. The trick is guiding them to their own conclusion rather than forcing one.

Example: Your cofounder insists an investor is secretly working against you. Instead of arguing, redirect their thinking:

"I see why that might seem off. Let’s double-check together." "What would have to be true for that to be a real risk?"

This does two things:

1. Moves them from an emotional state to problem-solving mode.

2. Helps them poke holes in their own paranoia instead of you doing it for them.

By meeting their fear with logic instead of dismissal, you help them dismantle it without making them feel foolish.

Limit Emotional Contagion

Paranoia spreads. If they’re constantly making you question every decision, vendor, or investor, you’ll start seeing ghosts too.

One person’s anxiety infects everyone around them. Set mental and conversational boundaries.

Example: Your cofounder fixates on every possible negative outcome. Instead of getting sucked in, you set limits:

"Let’s focus on problems we actually have evidence for. If something real comes up, we’ll handle it."

This does two things:

1. Keeps their paranoia from infecting your own judgment.

2. Forces them to differentiate real risks from imagined ones.

However, be careful not to overcompensate.

Address the Root Fear

Paranoia often isn’t about this decision or this betrayal. It’s deeper. Are they afraid of losing control? Being blindsided? Getting abandoned?

If you identify what’s really driving their paranoia, you can reassure them in ways that matter. It tends to be associated with being unfairly overpowered or humiliated before.

Example: Your cofounder panics about minor equity adjustments, convinced they’ll be cheated. Instead of arguing about this deal, go deeper:

"I get the sense that you’ve been in a situation where someone screwed you over before. Let’s make sure we’re structuring this so you feel protected."

This does two things:

1. Signals that you understand their fear, rather than dismissing it.

2. Gives them a sense of control, which reduces their need for hyper-vigilance.

Tug on those threads, lightly. If you push too hard, they’ll just become more defensive.

Know When to Cut the Cord

Some levels of paranoia can be managed. Others will poison the entire company.

If your cofounder is convinced everyone is out to get them, refuses to trust anyone, or sabotages key relationships, the reality is simple: they’re not built for the startup world.

If you can’t redirect the paranoia, you might need to walk away before it takes the whole company down with it.

Example: Your cofounder refuses to trust anyone, sabotages key relationships, and makes decision-making impossible. Prepare to exit instead of waiting for them.

Start documenting decisions so others see the pattern. Position yourself as the rational one in investor and board conversations.

This does two things:

1. Protects the company from their spiraling distrust.

2. Ensures that when the breaking point comes, you’re ready, not scrambling.

Paranoia is like quicksand. The more you struggle with it, the deeper it pulls you in.

At the end of the day, if your cofounder is paranoid, they need to learn how to be able to laugh at themselves and realize that consequences may not be as dire as they expected.

That’s all for now,

Tim He

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