Hiring Your First Ten People

Your fourth hire will interview your fortieth. That sentence is the whole argument for taking early hiring more seriously than almost anything else you do in the first two years.

I have built founding teams for my own companies and helped other founders build theirs. The mistakes are remarkably consistent, and they are not the ones people warn you about. Nobody's startup died because a founder hired someone with the wrong framework experience.

Hire for the next twelve months, not the next five years

The most common early mistake is hiring for the company you describe in your deck instead of the company that exists on Monday.

A founder raises a seed round and hires a VP of Engineering to lead a team of one. Eighteen months of runway, and a large part of it goes to someone whose actual skill — running 30 engineers — will not be needed for two years, and who did not join to write code alone at 11pm.

Hire for the twelve months in front of you. If the company works, that person will grow or you will hire above them, and both of those are normal, survivable outcomes you should say out loud during the interview. Buying seniority you cannot use yet is the most expensive way to feel legitimate.

The exception is genuine domain knowledge you cannot acquire. If you are building in a regulated market and nobody on the team has been inside one, that hire is not premature — it is the thing standing between you and an expensive year.

Range beats specialisation

At ten people, everyone does four jobs. Your first marketer will write copy, run paid experiments, do customer research, edit a landing page and probably answer support tickets in month one.

Interview for that reality. The question I lean on: "Tell me about a time you had to do work that was clearly not your job." You are listening for whether they found it energising or degrading. Both answers are legitimate in a mature company. Only one survives at ten people.

Specialists become correct around 30 to 40 people, when there is enough volume in a single function to fill a week. Before that, a brilliant specialist is underused and frustrated, and they will leave — usually after a year of you both quietly knowing it was not working.

Test the actual work

Unstructured conversation is close to useless at this stage, and early-stage founders rely on it more than anyone because there is no process to fall back on.

Give a real, paid, scoped piece of work. Four to six hours, compensated at a fair rate, on a problem adjacent to something you genuinely need. Not a puzzle. Not a take-home that reproduces your product for free.

For every early hire I now run something like:

• A working session, not a presentation. Solve a live problem together for 90 minutes. You learn more about how someone thinks in ninety minutes of collaboration than in five hours of interviews.
• A written artefact. Ask for a short document — a plan, an analysis, a critique of your current approach. Early-stage work is mostly writing and most people cannot do it.
• A reference call you source yourself. Not the three names they gave you. Ask on the call: "Who else worked closely with them?" Then call that person. The second-degree reference is where the truth is.

The paid trial has been the single highest-signal thing I have used. In roughly one in five cases it changed a decision I was already confident about — in both directions. Twice it turned a lukewarm interview into a hire who became indispensable.

Say the hard parts out loud

Early-stage founders oversell, because they are also selling to investors and customers and the muscle carries over. It is a false economy that shows up as attrition in month seven.

Tell candidates the actual runway. Tell them what is broken. Tell them the salary is below market and by how much, and what the equity would have to do to make up for it. Tell them the last two people who left and why.

Two things happen. Some candidates walk away — those were going to leave in six months anyway, at far greater cost. And the ones who stay have decided with real information, which means the first hard quarter does not feel like a betrayal.

I have never regretted being more direct than was comfortable. I have regretted the opposite several times.

The ten percent rule

At ten people, every hire is ten percent of your culture. Not ten percent of your headcount — ten percent of the behaviour that gets normalised.

Hire someone who is brilliant and dismissive, and dismissiveness is now an acceptable price for talent. Everyone learns that in about three weeks, and it is nearly impossible to unlearn. The tolerance you extend to your fifth hire becomes the standard your fiftieth inherits.

This is why the "brilliant jerk" question is not a philosophical debate at this size. It is arithmetic. One in ten is a policy.

Move fast, but not on conviction

Early-stage hiring should be fast — a strong candidate should go from first conversation to offer in under two weeks. You are competing against companies that can pay more, and speed plus honesty is one of the few advantages you actually have.

But fast is not the same as loose. Speed comes from compressing the calendar, not from skipping the evidence. Run the same trial, take the same references, and do them in ten days instead of five weeks.

And keep the standard that has saved me most often: if two people who met the candidate are unsure, do not hire. At ten people you cannot carry a mediocre hire. There is no team to absorb it, no process to contain it, and firing someone in a ten-person company is a company-wide event that costs you two months of momentum.

What I would do first

If you are about to make your first few hires:

1. Write down the four outcomes this person owns in twelve months, before you talk to anyone. If you cannot, you are not ready to hire — you are hoping someone will tell you what you need.
2. Design a paid trial that mirrors the real work.
3. Decide your two non-negotiable behaviours and reject on them without exception, however strong the skills.
4. Write the honest version of the pitch, including the risks, and use it.

The first ten set the ceiling. Everything after is easier or harder because of who you chose here — and unlike almost every other early decision, this one is very hard to reverse.