Hey y’all — imagine bootstrapping for 13 years… but then raising $22M.

That’s the story of AppSignal, the well-known application performance monitoring startup that grew to over 2,000 customers processing over 100 billion requests per month and built a deep reputation within the Ruby on Rails community for 13+ years.

I had used AppSignal when I was building projects with Rails in college because other options were too bloated so, when I saw that they had raised $22M from Elsewhere Partners years later in 2025, I was interested in the story behind the decision.

Why would the founders of a company that had done millions in revenue while bootstrapping suddenly raise a ton of capital after years of turning down offers?

I sat down with two of AppSignal’s co-founders Thijs Cadier and Roy Tomeij, as well as the company’s new post-investment CEO Brandon Swalve to find out:

For years, Roy was the face of the brand to customers and partners. When the investment happened last year, even though he remained with the company as a board member and brand ambassador, he stepped back from his role as Chief Customer Officer.

What’s interesting about it is that this was initially his idea. When we spoke, he was very candid, saying that “I think my qualities are in taking something from 0 to 10 and not so much from 10 to 1,000.”

He, Thijs, and their co-founder Wes, took the company to millions in ARR despite, as Roy says, “knowing only my high school economics class.”

That type of self-awareness as a founder, even after 13 years, is hard to reach. But admirable. Roy didn’t wait for the company to struggle, he put all ego aside and focused on what was right for AppSignal.

AppSignal stayed bootstrapped for years in part because every funding conversation went down a rabbit hole of trying to turn the business or product into something it wasn’t.

Roy and Thijs knew outside capital comes with expectations that tend to lead to feature bloat, which was the exact thing they built AppSignal to push back against from incumbents in the first place.

So, despite offers, they held onto their bootstrapped identity.

It wasn’t that they were anti-VC. Bootstrapping just allowed them to keep the product easy to use, and raise on their terms.

AppSignal is loved by users and has done millions in revenue in part because the product’s original philosophy of deliberate simplicity in a market where competitors get bloated has stayed true since day one.

Thijs highlighted that their mindset is “always build from simple primitives instead of all these separate flows and bells and whistles everywhere.”

It’s easy to say that when you found the company. It’s much harder for it to still be actually true after nearly 15 years (despite continuous development on the product, improvements, etc).

Bloat is a choice, and one that works against you in many ways.

If you want to make something people not only want, but love, it has to feel like it’s built for them specifically rather than them feeling like they have to navigate menus and tabs to find what they’re looking for.

Roy, Thijs, and Brandon all mentioned AppSignal’s culture as the most important thing that’s let them have success and that they want to preserve in the future.

Put concisely, they always want to make sure AppSignal customers and the broader developer community are treated the way they themselves would want to be treated.

In fact, the “no-asshole company” approach was Roy’s #1 consideration for whoever stepped in to take the reins. And Brandon’s commitment to it made it clear that he was the guy for the job.

This is yet another factor that has led AppSignal to be loved by their users over the years. It made their community outreach (events, conference sponsorships, their involvement with the Rails Foundation, and more) all ring authentic rather than extractive.

And, in the age of LLMs where product is easier to build than ever, customer love is a moat.

When I spoke with Roy he told me bootstrapping wasn’t just a financial strategy, it became part of their identities.

So stepping past that and into a new future meant finding partners who don’t want to do what so many others had wanted to over the years (aka changing AppSignal into something it isn’t).

The team spent a year talking with potential investors, and operators to step in as the new CEO. They went with Elsewhere Partners and Brandon, respectively, because they already understood AppSignal’s market inside and out, their motivation was to amplify what already existed rather than transform it, and they had the GTM experience that the team wanted.

Now their goal a massive US-focused expansion in 2026 and beyond as new opportunities like AI and OpenTelemetry are expanding the market organically, not a radically different product.

AppSignal’s journey proves you can build bootstrapped, stay human, and still reach meaningful scale. If you do that, the opportunity for capital will be there when it’s right for you.

If you’re trying to figure out if you’re still in the 0-to-10 stage or staring at your own “what’s next?” moment, AppSignal’s playbook is one of the most clear-minded recent examples of doing it right.

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