Hey, I’m Tim! ☕

Being a cofounder = “moving fast,” “breaking things,” “scaling quickly.”

There's an infinite list of things to prioritize: product, users, funding, shipping.

It’s natural to delay what doesn't feel urgent, like a moment of tension with your cofounder. You tell yourself you’ll deal with it later when the fires are out.

The catch? Technical debt slows your product; relationship debt sinks your company.

The 3rd Level

Relationship debt is the emotional baggage that builds up over time if left unaddressed.

• One cofounder makes a quick decision to pivot the product without consulting the team. The other feels excluded and undervalued.

• Two cofounders avoid addressing a growing tension about equity splits. One starts to question the other’s commitment.

• One cofounder feels stressed but never vocalizes it. When the burden becomes too much, they lash out or shut down.

It’s a plague.

YC’s first Batch Director and in-house founder coach, Amy Buechler, outlines the 3 levels of conversation.

1. The first level communicates information. Metrics, deadlines, numbers.

2. The second level communicates thoughts. Opinions, visions, strategy.

3. The third level communicates feelings. Fears, excitement, resentment.

You probably spend most of your time in Level 2 conversations, using Level 1 as quick transitions.

However, only Level 3 conversations can resolve relationship debt.

Cofounders must step into the uncomfortable but transformative territory of feelings.

• I feel like we’re growing apart on this vision. Can we get aligned?

• I need more support when we’re making tough decisions.

• I’m scared we’re not going to make it if we don’t solve this tension now.

Why’s It So Hard?

They’re intimidating.

Level 3 conversations cut through the fluff, which is why they can feel like a gut punch. They often require you to be much more direct than you’ve been socialized to be.

Avoiding them is a response rooted in self-preservation. You think this potential emotional mess can wait until things are “less crazy.”

But the cost of indirectness is more emotional baggage.

Here’s a pattern I’ve heard about a dozen times this month:

• Year 1 of cofoundership was like the honeymoon phase. Smooth sailing.

• Halfway into year 2, some tension creeps in but no big deal, right?

• Within weeks or even days, things spiral and escalate out of hand.

• Cofounders wonder where that all came from. Things were going well.

This is what happens when only Level 2 conversations go well. You’ve built your MVP, maybe you’ve gotten some early users or investors.

Your company is growing but your cofoundership hasn’t kept up.

How to Make it Easier

As with all debt, compound interest is what kills you. Don’t let it accumulate.

Think of tough conversations as a subscription service: something you renew regularly, not a catastrophic intervention you reserve for emergencies.

If you’re paying for a gym membership, you don’t wait until your health is in crisis to go for the first time.

If there’s something you feel but haven’t said, you’re in Level 2 territory. The goal isn’t to “win” the conversation or even to resolve it in one go.

It’s to create a space where feelings can surface without judgment.

Without cringing.

You can even have these outside the office so they don’t feel so proper and professional.

Over time, you’ll find these conversations to be less awkward, less forced.

Just remember that if your cofoundership isn’t strong, no amount of product-market fit or funding will save your company.

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Thanks y’all,

Tim He