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 websites for fun, and figured: why not try to make a living from it? For the first number of years, I worked weekend jobs instead of taking a salary (thanks for not kicking me out, Mom and Dad!). Since 2003, I’ve worked only for myself. No boss. No performance reviews. Just me and my co-founders.

Fast-forward twenty-two more years, to AppSignal’s Series A. We now have a CEO, a board of directors, and an external investor: people who didn’t join us for our good looks. They invested because they believe in our vision AND expect a return. And honestly? I want the same. I’ve poured years of my life into building a sustainable, globally respected product, serving customers in 60+ countries.

With $22M in growth funding comes the responsibility to spend it wisely, and to show that our bets pay off. That means faster growth, more hires, and big strategic swings. That aligns with our goals, but it also introduces a new dynamic.

For the first time in my life, I feel like I kind of have a boss – not in a hierarchical sense, but in terms of accountability. We now have a quarterly board meeting where we show our progress. And while our first one went well, I can already feel that internal whisper: “What if we fall short next time?”

I’m not worried about being reprimanded, as our investors are aligned with our mission. But I still don’t relish the idea of walking into a boardroom and saying, “We missed the mark.”

So yes, there’s pressure. I knew that going in, and I’m still adjusting. But as Lahiru pointed out, bootstrapping has limits. Global expansion, rapid team growth, and broadening language support all become more attainable with the right resources.

Even if it sometimes feels like I’ve traded in my freedom, the truth is: I’ve traded up for the chance to build something bigger, faster, and bolder. And that’s a trade I’m excited to make. 🚀