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The 5 Fights

You’ve read the title, no intro necessary, let’s jump in.

The “Who Gets What?”

Equity. Salary. Upside.
If it affects your wallet, it affects your relationship.

Most cofounders want to be “fair.” But one founder’s fair is another’s “wtf?”

Handled well, these conversations lead to alignment.
Handled poorly, these lead to lawsuits. Re: Zuckerberg.

This happens for 2 reasons:

1. It feels like putting a price on the friendship.
   Equity splits feel transactional. In reality, a solid agreement protects the relationship, not threatens it.

2. It introduces hierarchy.
   It feels like assigning rank in what was an equal friendship.

This is what I tell my clients to do instead:

• Use vesting cliffs and equity calculators.
  They’re not perfect, but they give you something objective to work from.

• Bring in a neutral third party.
  A fellow founder or advisor can frame these talks as strategy, not drama.

The “I Work More”

It’s mathematically impossible for cofounders to contribute exactly the same amount.

Each cofounder brings different time, energy, and focus based on their situation. How much runway they have, how passionate they feel, what else they’re juggling in life.

Some are sprinting 100-hour weeks.
Others are clocking in at 50.

That difference isn’t the problem.

The problem is when effort gets tied to entitlement.

What often starts as a conversation about time quickly turns into a deeper debate: What’s fair? What’s valuable? What’s worth more?

This happens for 2 reasons:

• Founders don’t agree on what “full-time” means.
  One person’s “all in” is another’s “side project.”

• Not all work is visible.
  The cofounder building decks on Sunday morning may not see the cofounder answering Slack at midnight.

This is what I tell my clients to do instead:

• Talk about work styles and personal constraints.
  One cofounder may be a new parent. Another may have a longer runway. Normalize different capacities and build around them.

• Check in regularly.
  Resentment festers in silence. A 10-minute alignment convo every few weeks can save you months of drama.

The “Who Says”

You're the product person.
They're the GTM machine.
Decision-making feels natural. No drama.

But sooner or later, you hit:
No one owns the decision. Or everyone thinks they do.

Fundraising. Strategy. Brand.
The “gray zones” where roles blur and opinions multiply.

This happens for 2 reasons:

• There’s overlap or a void.
  Conflict pops up when either everyone wants to weigh in. Or no one knows who’s in charge.

• The decision stakes are tied to identity.
  Fundraising isn’t just a tactic (it’s a test of who’s trusted). Brand isn’t just design (it’s someone’s personal taste).

This is what I tell my clients to do instead:

• Use a framework: consult vs. decide.
  It’s okay to have input without control. Clarify the difference between being consulted and being the decider.

• Talk about what you’re optimizing for.
  Control? Speed? Craft? Exit? Your choices in hard moments should align with what you actually care about.

The “They Piss Me Off”

Sometimes, it’s not about equity or effort.
Sometimes, it’s not even about the business.

You just don’t like each other anymore.

Morale tanks.
People pick sides.

The whole team starts doubting if this company is going anywhere.

This conflict is brutal because it’s personal.

This kind of tension can destroy a startup faster than missed revenue targets or a failed product launch.

This happens for 2 reasons:

• Emotions get tangled with business.
  Working closely means personal boundaries blur. It’s easy to forget where “cofounder” starts and ends.

• No one wants to be the “bad guy.”
  Avoiding confrontation lets resentment fester until it’s too late. It’s especially awkward when you have a team to think about.

This is what I tell my clients to do instead:

• Set up a breakup framework from day one.
  Define how to handle exits before anyone needs to leave. Clear processes make endings cleaner.

• Seek neutral help early.
  Therapy, coaching, or an unbiased advisor can help navigate emotional landmines before they explode.

The “We’re Screwed”

Every startup faces near-death moments.

Funding falls through.
A launch flops.
A key customer ghosts.

Some founders stay hopeful and push harder.
Others see the writing on the wall and want to fold.

What feels like grit to one founder can feel like stubbornness to another.

The real tension is in the decision: Do we fight through the fire or cut our losses?

This happens for 2 reasons:

• Different stakes, different reactions.
  One founder might have a safety net. Another is betting their last dollar.

• Optimism vs. realism isn’t black and white.
  Hope can look like denial. Caution can look like giving up.

This is what I tell my clients to do instead:

• Get clear on each other’s runway, financial and emotional.
  Understand what’s realistic for everyone involved.

• Discuss risk tolerance upfront.
  Are you built to fight fires or fold fast? Knowing this helps avoid shock when things go sideways.

Having one or multiple of these fights doesn’t mean you’re a bad cofounder or that your cofoundership is bad. They’re normal.

Just prepare for them and move on.

That’s all for now,

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

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