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Cofounder-ish

I recently joined Twill as their founding growth lead. They do referral recruiting. As such, I’ve spent a lot of time thinking about hiring.

The first hire at a startup is rarely treated like the first builder. They’re treated like the first helper. That’s a mistake.

Most founders don’t realize it, but they’re unintentionally setting up a triangle where two sides are welded together and the third is just glued on. That third person might be cracked, motivated, and deeply aligned with the mission. But they’re stepping into something that already existed before them: a cofounder bond.

And cofounder bonds run deep.

You’ve been through hell together. You’ve pitched investors half-asleep and coded through weekends. You’ve fought, cried, recovered. You’ve argued about whether to move a button on the homepage for six hours. You’ve walked out of meetings where no one else believed in you. You’ve turned to each other with nothing but conviction.

That’s not just working together. That’s history.

So when you bring in your first hire, you’re changing the social physics of your company. And almost no one prepares for that.

Most founders don’t even see it happening.

• You’re in a meeting. Riffing on a new idea.

• You turn to your cofounder. The one you’ve always riffed with.

• The new hire watches. You don’t mean to exclude them.

• You’re just moving fast. You’ve always talked this way.

But over time, the pattern becomes visible: decisions happen in pairs. Debates happen off-camera. Priorities shift without context. Hence, the third wheel.

The damage compounds once that happens.

Because third wheels don’t push. They don’t lead. They don’t challenge the direction. They do what’s asked. They nod. They wait. They execute.

And if they’re smart, they eventually leave.

Why This Happens

Cofounders confuse inclusion with context.

Just because someone’s invited to the meeting doesn’t mean they’re in the loop. Just because someone’s told what’s happening doesn’t mean they get why.

Your first hire wasn’t there when you pivoted the product.
They weren’t on the 2 a.m. call with your first customer.
They didn’t sit through the silent car ride home after your demo bombed.

They joined a story already in progress. And they don’t know how to write themselves into it.

They might think:

But that’s wrong. And dangerous.

Because in early-stage startups, your first hire is the company.

If they don’t feel real ownership, the culture calcifies into something where no one except the cofounders feels real ownership.

The Unspoken Hierarchy

The third wheel effect is really just a symptom of an unspoken hierarchy:

The cofounders are the “real” company. Everyone else is there to help.

Cofounders don’t say this out loud. Most don’t even think it consciously. But it’s baked into how decisions are made, how feedback is handled, how conflict is resolved.

And people feel it. Instantly.

Even subtle cues give it away:

Who gets to say “no”?
Whose priorities always win?
Who talks the most in meetings?
Who do you instinctively turn to when something goes wrong?

Your first hire is watching. Not just what you say but who you trust.

If that trust is locked between cofounders, everyone else will check out. They’re not lazy. They simply don’t feel like the company is theirs to shape.

And they’re right.

How to Fix It

The solution is simple but not easy: you have to rewire the relationship.

You can’t treat your first hire like a helper. You have to treat them like a co-creator. Change your behavior, not just your org chart.

1. Redefine the center of gravity.

If every key decision still runs through the cofounders, then nothing has changed. Shift gravity. Give your first hire a domain they own end to end. No founder override. If you can’t trust them with it, you hired the wrong person.

2. Share the backstory.

They don’t have the context you do. So give it to them. Walk them through old decisions. Share the messy debates. Explain why certain things are the way they are. Invite them into the narrative.

3. Let them break things.

Ownership isn’t real until someone is allowed to screw up. If you jump in to fix everything before it hits the market, they’re only shadowing. Let them make bets. Let some fail. That’s how belief forms.

It’s Not a Role, It’s a Relationship

Founders often obsess over hiring the “right” person. But even the perfect hire will fall flat if the relationship doesn’t evolve to include them.

You can’t bolt someone onto a two-person dynamic and expect them to thrive.

You have to make space.

That’s all for now,

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

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