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”