Hiring your first ten employees

The first ten people you hire at a startup are not normal employees. They are accomplices. When Fredrik and I were building Mediapilot in Stockholm, we couldn't afford polished CVs. My own background was in PR sales on commission only, a job everyone around me had advised against taking, so I already had a bias toward raw hustle. We didn't have the budget to lure people away from comfortable jobs at established agencies. So we hired for what people in Silicon Valley like to call slope rather than intercept. That is just a mathematical way of saying we looked for steep potential instead of a high starting point. We wanted people who were hungry, adaptable, and willing to figure things out with us. It worked. We found brilliant young people who grew with the company. But I will be honest with you, it only really works for the first ten or fifteen hires. After that, the company needs a different kind of structure, and if you keep playing by the old rules, things start to break. I know, because we broke it a few times.

Buying false comfort

Eventually, a company reaches a size where the founders feel overwhelmed. Let me explain how this usually happens. You look around at the chaos you have created and think you need adult supervision. This leads to the first classic mistake I made: hiring seniority as insurance. We brought in people with impressive titles from larger organisations, assuming their years of experience would magically solve our scaling problems. I thought I was buying a safety net. What I actually bought was a massive salary bill and a cultural mismatch. People who have spent ten years at a multinational are used to infrastructure. They expect a legal department, a dedicated IT person, and a well-defined job description. Put them in a raw startup where the coffee machine is broken and the product roadmap changes on a Tuesday, and they freeze. They try to build committees when you need them to pick up the phone. I learned the hard way that you cannot outsource the messy work of building the machine. You have to hire people who actually want to hold the spanner.

I thought I was buying a safety net. What I actually bought was a massive salary bill and a cultural mismatch.

The cruelty of being nice

The other side of hiring is firing, and I was terrible at it. There is a specific agony in realising you have made a hiring mistake. You see the signs early. They miss targets, they irritate the rest of the team, or they simply cannot do the job they claimed they could. But instead of acting, I would wait. I convinced myself that firing them would be cruel. I told myself they just needed more time, clearer instructions, or a different project. The truth was, I was just avoiding an uncomfortable conversation. I kept a frankly terrible hire on the payroll for nearly a year out of misplaced Swedish politeness. By the time I finally let them go, the rest of the team was completely demoralised. They had been carrying the dead weight while I played the nice guy. The actual cruelty was making the good people suffer because I lacked the spine to fix my own mistake.

How to actually check a reference

You can avoid a lot of this pain if you learn how to do reference checks properly. For years, I treated references as a polite formality at the end of the hiring process. I would call up a former manager, ask if the candidate was a good worker, listen to them say yes, and hang up. It was entirely useless. Nobody will ever tell you a candidate is awful when asked a direct question like that. Eventually, I changed tactics. I stopped asking for general opinions and started asking for specific scenarios. Now, I ask what the person is like when they are under pressure and missing a deadline. I ask what their biggest failure was during their time there, and how they reacted to it. The most revealing question I ask is what role they would hire this person for if they were starting a new company tomorrow. If they hesitate, or if they give a vague answer, you have your warning.

Building Mediapilot to over a hundred people taught me a lot about what not to do. Even today, working on Anchor and Substrat or looking at a small angel investment, I still find hiring incredibly difficult. You are trying to predict human behaviour based on a few hours of conversation and a sheet of paper. It is an inherently flawed process. I use my life plan to track my own progress, rating my work, finances, health, and family time out of ten every year, but you cannot neatly score a human being before you work with them. I still get it wrong. I still occasionally get seduced by a shiny CV or let my gut override my brain. But I no longer expect senior hires to save me, and I no longer wait a year to fix a bad fit. I haven't got this figured out entirely, but I sleep a bit better knowing the mistakes I make today are at least new ones.