Today we’re talking about something founders love to complain about and quietly avoid:

Hiring.

Not in the “how to interview better” way, or the “here’s a checklist you’ll never use” way.

Specifically, why it feels so hard, why it breaks so many early teams, and why the problem usually isn’t what founders think it is.

Because despite what LinkedIn posts might suggest, startup hiring is not about perks, comp, or “finding rockstars.” It’s about finding people who don’t panic when there’s no playbook.

Let’s get into it →

When early founders talk about hiring, they almost always start with money.

“We can’t pay what big companies pay.”“We lose candidates to FAANG.”“We’d hire faster if we had more budget.”

It makes sense. Salary is concrete. It’s easy to point to. It feels like the obvious bottleneck.

But in practice, compensation is rarely the real reason early-stage hiring fails.

The people who actually do well in startups aren’t shopping for the highest paycheck. They’re shopping for something else entirely, even if they don’t articulate it that way.

They’re looking for:

If someone is optimizing for stability, predictability, and clarity, a startup is going to feel uncomfortable no matter how much you pay them. Conversely, if someone is wired to seek growth and ownership, a startup can feel like an upgrade even with a pay cut.

This is why some founders are shocked when a candidate turns down a bigger company to join a messy early team. It looks irrational from the outside. It isn’t.

It’s a different optimization function.

Here’s the uncomfortable truth most founders only realize after the hire:

You’re not hiring for the role you wrote down.You’re hiring for the role that doesn’t exist yet.

Early on, job descriptions are mostly fiction. They’re aspirational. They’re guesses.

What you’re actually asking someone to do is:

That’s a very different ask than “run paid ads” or “own backend services” or “manage partnerships.”

This is where hiring gets tricky. Because most people are very good at operating within a system, and far fewer are comfortable creating one from scratch.

Neither is better in general. But only one works early.

Every founder has a version of this story.

They hire someone impressive. Great resume. Big brand names. Confident in interviews. Knows all the right words.

And then… it just doesn’t work.

They need more direction than expected.They hesitate when priorities shift.They ask for clarity that doesn’t exist yet.They wait for decisions instead of making them.

From the outside, it looks like underperformance. From the inside, it’s often something simpler: altitude mismatch.

Some people do their best work when there’s:

Early startups don’t have those things. Not because founders are lazy, but because the company is still figuring out what it even is.

Put someone who thrives on clarity into ambiguity, and they don’t magically become entrepreneurial. They become anxious or frustrated.

Again: not a skill issue. A context issue.

Founders often say they’re looking for “initiative” or an “entrepreneurial mindset,” but those words are vague to the point of uselessness.

What they’re usually trying to describe is something much more specific:

The ability to act without permission and recover quickly when wrong.

That’s it.

People who do well early:

This is also why interviews are such a poor proxy for success. Interviews reward articulation, confidence, and retrospective storytelling. Startups reward judgment in real time.

Someone can sound brilliant explaining how they solved a problem six months ago and still freeze when faced with a new one today.

A lot of founders roll their eyes at “culture” early on. It feels premature. You’re just trying to ship.

But culture isn’t something you add later. It’s something you accidentally create immediately.

In a three-person company, culture shows up as:

One hire who operates differently can change the entire dynamic. Suddenly things take longer. Conversations feel heavier. Decisions get escalated instead of made.

That’s why culture fit matters so much early, and why it gets misinterpreted.

It’s not about whether you’d get a beer together. It’s about whether you share the same instincts under pressure.

There’s a moment in every startup where the founder realizes something uncomfortable: their leverage no longer comes from doing the work themselves.

It comes from who they bring in.

At that point, hiring stops being a task and becomes the job. Not because founders love recruiting, but because every hire has second-order effects.

A good hire:

A bad hire does the opposite. Quietly.

This is why experienced founders take so long to hire and say no so often. They’re not being precious. They’re protecting momentum.

Interviews reward storytelling. Startups reward judgment.

This is where trial projects come in.

Not homework. Not unpaid spec work. Real, scoped, paid projects that resemble actual work.

They show you:

It’s better for candidates too. Both sides find out quickly if the relationship works.

Most hiring mistakes don’t come from lack of skill. They come from misaligned expectations.

Trial work surfaces that early.

The biggest hiring risk is not hiring someone bad.

It’s hiring someone good at the wrong altitude.

People who want to manage before they’ve built. People who need structure before they can move. People who optimize before there’s anything to optimize.

Early-stage companies need builders first. Systems come later.

If someone hasn’t shipped the thing themselves, they shouldn’t be managing the people shipping it.

When hiring works, it doesn’t feel dramatic.

Things just:

The company starts scaling beyond the founder’s personal output. That’s the real milestone.

Hiring isn’t about filling seats. It’s about reducing entropy.

And in a startup, that’s everything.

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