The equity conversation I avoided

Remember agreeing your equity split? It probably felt fair. It was also a guess about the future, made on the day you knew the least.

Then the startup changed. Roles shifted and contributions diverged. One of you started carrying more of the weight, sometimes a lot more.

That was me. In one of my early startups I had 25% and my co-founder had 75%. A few months in, the gap in effort was obvious. They were treating it like a part-time gig with some ops input. I was running marketing, product and investor relations.

I didn’t raise it. I told myself I was keeping the peace, but I was really just storing up resentment. Trust wore away, and it all blew up at the worst possible moment: we were scaling up operations, and I was leading that scale-up.

The conversation I avoided would have taken an hour. The dispute that replaced it came when real value was on the table, which is exactly when everyone digs in hardest.

Misaligned equity is like termites. You don’t notice it at first. It works quietly until there’s structural damage.

If you’ve got that nagging feeling, here’s how to start:

1. Book it. Put a “Roles catch-up” in the diary for next week. Keep the title neutral. It’s a conversation, not an ambush.
2. Prepare the facts. Write down what each of you was originally meant to own and what you actually own now. List specific contributions and how they’ve shifted. Specifics keep it about the business, not about who’s the better person.
3. Share, then pause. Explain what you’ve noticed. Then ask your co-founder to do the same exercise before you next meet. Don’t push for a decision in the first conversation.
4. Follow up. Meet the following week, compare notes and agree next steps.

This won’t fix the split overnight. It might lead to harder talks about vesting, re-cutting shares or changing roles. But you’ll be having them with the facts on the table, and before a valuation makes everything harder.

Raise it now, while it’s cheap.

Keep building.