When I announced that Stripe had acquired Lemon Squeezy, I said I'd write more once I'd digested what had just happened. That was over two years ago. To be honest, I'm not sure I've fully digested it yet.
But leaving feels like a good opportunity to stop for a moment and try.
Taking stock
It's surprisingly difficult to put the last few years into perspective when you've been in the middle of them.
In 2023, Lemon Squeezy grew incredibly quickly. We were shipping features, growing the team, trying to keep up with demand, and figuring things out as we went. Then came the acquisition process, months of due diligence, trips to San Francisco, and suddenly a job at Stripe. There wasn't much of a gap between any of it.
Looking back, I tend to remember the work. The code, the bugs, the decisions, the calls. At the time, there was always something else that needed doing. It didn't really feel like we were living through some big career milestone. We were just trying to get through the week.
But when I step back, it is a bit crazy. We built Lemon Squeezy from scratch and grew it into something that helped people make a living online. Eventually, Stripe decided the company and technology we'd built were valuable enough that they wanted to acquire it.
For anyone outside the tech world, Stripe is one of the biggest and most respected private technology companies in the world. Having them want to buy something we'd built was pretty surreal. Then I spent two years leading an engineering team there and getting to see how a company like that works from the inside.
I think part of what I'm still processing is how far that is from where I started. I've spent years making things for the web, launching products, and trying to build businesses. Some worked. Plenty didn't. Lemon Squeezy grew out of that same desire to build something useful, but took us somewhere I couldn't have predicted.
I'm proud of what we achieved. I'm also very aware that "we" is doing a lot of work in that sentence. My co-founders, our team, and the people who trusted us with their businesses all played a part. So did timing and opportunities we couldn't have manufactured ourselves.
The acquisition changed life for our family in ways I'm still getting used to. But something I want to remember, beyond the financial outcome, is that we made something people wanted and built a team capable of delivering it. That's pretty special.
Two years at Stripe
Going from an 18-person startup to a company with thousands of employees was a huge adjustment. So was going from a CTO role that was mostly hands-on engineering and technical leadership to being an Engineering Manager.
I wrote about this in my 2025 review, but it took me a while to understand just how different those jobs were.
At Lemon Squeezy, if something needed building or fixing, I'd often get stuck in and do it. As an EM, much more of my time went into planning, hiring, coaching, performance reviews, and helping the team execute. I had to get more comfortable with contributing through other people, and with the fact that a useful day's work might involve very little code.
I've learned a lot about what it takes to make a team effective. Clear priorities, realistic plans, and making sure people have the context and support to do good work. These things sound fairly obvious written down, but doing them consistently is a different matter.
I've also gained a much better appreciation for how engineering works at a larger scale. The expectations around reliability, security and risk are high, and the number of teams involved changes how decisions get made. Some of that was frustrating when I was used to moving quickly. But seeing it from the inside gave me a perspective I wouldn't have gained running a small business.
The people have been a real highlight. I've worked with some incredibly talented, thoughtful people at Stripe, and I'm thankful for the time I've had with them. Being able to help build Managed Payments alongside continuing to look after Lemon Squeezy has been a valuable experience.
I went into Stripe hoping to learn how a much larger technology company works. I certainly got that opportunity.
Getting back to building
The experience has also helped me understand what I want to spend my time doing.
I miss small teams. I miss being close to the product and the customers. I miss having an idea, building it, and getting it into someone's hands without quite so many steps in between.
And, honestly, I miss building things myself.
There are parts of engineering management I've enjoyed, and important lessons I'll take into whatever I do next. But I've come to realise that I want hands-on product work to be a much bigger part of my day again. The corporate environment and the amount of coordination that comes with it haven't been the best fit for me.
So I've decided to leave and put my time back into startups.
AI is a big part of what I'm excited about next. I've been spending more and more time experimenting with it, both as a tool for building software and as something to build products around. There's a tonne of hype, but there are also real opportunities to make useful things that would have been difficult or impractical a few years ago.
I'm particularly interested in what a small team can do with these tools. How much more can we build? Which problems can we now tackle? And how do we turn something impressive in a demo into something people can actually depend on?
I don't have specific projects to announce here yet. For now, I'm looking forward to having more time to explore ideas, build things, and see what sticks.
I've spent the last three weeks taking some time off to recharge. The last few years have been intense, and it's been good to have some space to appreciate what's happened before filling my days with the next thing.
Lots learned. Lots still to learn. I'm looking forward to getting stuck in again.