For years, I genuinely believed we ran a flat, non-hierarchical organization at AppSignal. I didn’t see myself or my co-founders as “the bosses” and everyone else as employees. I saw us as one team. I tried to be friendly with everyone.

I was wrong.

While I imagined us all sitting around the same table, the team saw a clear hierarchy. They saw founders, shareholders, and board members. They saw people who could ultimately decide their fate. No amount of casual Slack messages could erase that power dynamic.

“Non-hierarchical” had two different definitions in the same company. Mine was about … read more “You’re Not Their Friend. You Never Were.”

I can’t read every résumé. Whether I read yours is based on the answer to the question that’s our equivalent of a cover letter:

“Why do you want to work at AppSignal?”

That’s the cheat code. It’s the high-leverage moment where 98% of people quietly disqualify themselves.

If you answer this question well, you don’t just move forward: you leapfrog hundreds of other applicants. It’s the first thing I read, and it could be the only thing; if your answer feels generic or half-hearted, I will not even get to your CV. Not because I’m trying to be tough, but … read more “Want to Work With Me? Start Here.”

When raising $22M for AppSignal, we technically had every document we needed. Somewhere.

Revenue spreadsheets? Let me export a P&L from Moneybird and massage it in Excel. Contracts? Some were in PandaDoc, others buried in my inbox. Cap table and dividend distributions? Let me track down those PDFs. CIT returns? Logging into the accountant’s portal.

Truthfully, a lot of what I needed was where it should be, properly stored in Google Drive by our operations manager or me. But not everything. And when you’re under the microscope, being unable to produce a document quickly doesn’t look great.

The … read more “Preparing for Due Diligence from Day One”

As you probably know by now, AppSignal, the company I co-founded, raised $22 million in a Series A not too long ago. Overnight, I was no longer the bootstrapper I had proudly identified as since 1998. Enter cognitive dissonance.

For years, whenever someone asked about AppSignal’s origins, I would share how we built the company without any outside investment. That detail wasn’t just trivia; it was a point of pride. We were one of the few. A rare breed. The realization that we had now joined the ranks of the funded, “just like the others,” hit me harder than … read more “Bootstrapping Was My Identity. Then We Raised a Round.”

A few days ago, I asked if anyone had questions about AppSignal‘s recent funding round. Lahiru Himesh Madusanka responded: “Do you feel more pressure now that you’ve raised capital from external partners? It’s something I’m very keen to know about. I’ve always seen bootstrapping as the way to go if you’re passionate, but at the same time, there are certain limitations when you’re bootstrapping.”

The short answer? Absolutely. For the longer answer, let me expand on the clickbait title above.

On my 18th birthday in August 1998, Thijs and I decided to start “an internet business.” We’d been building … read more “Do I Have a Boss for the First Time Ever? (I’m 44…)”

A few days ago, I asked if anyone had questions about AppSignal‘s recent funding round. Stanislav Katkov responded: “Have you considered raising from EU investors? Did you have to incorporate in the US after raising with US investors?”

We spoke with several potential partners, some based in the US and others in the EU. A few were clearly not the right fit from the beginning, while others stayed in the running much longer. Ultimately, we made our decision based on cultural alignment, market expertise, experience, and deal terms.

Staying within the EU might have made things easier. … read more “Why a Dutch Company Raised $22M in the US Instead of the EU”