The mistakes first-time founders make

I spent the first two years of building my first company aggressively pretending to be a businessman. Fredrik Bage and I had started Mediapilot in Stockholm, and if you had looked at us from the outside, we were doing everything right. We had whiteboards covered in marker pen. We had long meetings about our brand values and company culture. We drank an obscene amount of filter coffee in cafes around Södermalm. The only thing we were missing was actual revenue.

When I talk to first-time founders today, usually over a bad game of tennis or a coffee down here in Marbella, I see the exact same panic masked as productivity. I try to be gentle about it, because I remember exactly how it feels. You are terrified of failing, so you fill your days with things that look like work. It is much easier to play house than to actually build a business.

The comfort of motion

This is the easiest trap to fall into. You confuse activity with progress. Designing a slide deck feels like progress. Organising your inbox into colour-coded folders feels like progress. Getting a lawyer to draft a forty-page terms of service agreement for a product nobody uses yet feels incredibly professional. None of it matters. When I look back at my own early days, I cringe at how much time I spent worrying about business cards.

At Mediapilot, it took us roughly seven years to grow to a point where we had created over a hundred jobs. But those early days were largely spent hiding from the one thing that actually drove the business forward: finding strangers and convincing them to pay us. We would spend three days tweaking a proposal document, convincing ourselves that the exact shade of blue in the logo was the reason a prospect was hesitating. It is a defence mechanism.

You can survive a lot of bad decisions if you have cash flow, but you cannot survive a perfect business plan if nobody buys what you are selling.

The polite sales meeting

That brings me to the second mistake, and it is one that hurts to admit because my background is literally in sales. Years before Mediapilot, I took a job at a PR agency on commission only. Everyone around me told me it was a terrible idea, but Fredrik told me I would be good at sales, and I eventually figured it out. I learned how to close. Later on, when I worked on the commercial side at Happeo, I knew exactly how to drive enterprise software deals. But when you start your very first company, something shifts in your brain. Suddenly, it is your baby on the line. You become desperate to be liked.

I see young founders go into sales meetings and do everything except ask for money. They give a brilliant presentation. They answer every technical question. They nod, they smile, they build excellent rapport with the client. Then the hour is up, everyone shakes hands, and the founder walks out onto the street thinking it went incredibly well. They send an email a week later and hear absolutely nothing back.

I did this repeatedly in Stockholm. I would have wonderful, friendly chats with potential clients, terrified that if I actually named a price and asked for a signature, the warm atmosphere would evaporate. I wanted a friend, but the company needed a customer. Let me explain how this actually needs to work: you have to ask for the money. You have to look them in the eye, state your price, and then shut up and wait for their answer. The silence will feel awful. It will feel like it lasts an eternity. Learn to sit in it anyway.

What I still get wrong

I wish I could tell you that I eventually grew out of all this and became a perfectly rational operator. I did not. Even now, building Anchor to help alienated fathers, or working on Substrat for AI builders, I still catch myself doing it. I will spend an hour rearranging my desk instead of making the hard phone call. Since around 2010, I have kept a written life plan that I update every year, rating things like family, health, finances, and work out of ten. Sometimes I will look at that plan, see that my rating for work is slipping, and try to fix it by tweaking a spreadsheet instead of doing the actual, uncomfortable work that matters.

The difference is that I catch myself much faster now. I know the symptoms. When I feel that familiar urge to overhaul my client database on a Tuesday morning, I force myself to stop, pick up the phone, and ask someone for money instead. I'll be honest with you: usually, I still hate the feeling. It still makes me sweat. But the only thing worse than a slightly uncomfortable sales conversation is having to shut down your company because you were too polite to ask for the sale. I haven't got this entirely figured out, but I know that much.