The right time: Leaving Automattic

A little over a month ago, I was sitting in my office after Christmas. Visiting family had all headed home, and my wife had gone back to work for a 24-hour shift at the hospital. I spent the next 16+ hours, interspersed with dog walks and meals, building with Claude Code. Then I did it again. And again. For five straight days.

This wasn’t my first time working with Claude or other AI code-gen tools. I’ve been using them consistently for the past two years. But this was the first time I had a truly uninterrupted stretch of time, and the first time the models, especially Opus 4.5, felt this capable. I was able to build nearly everything I imagined, end to end, at a pace that felt fundamentally different from anything I’d experienced before.

To borrow the quote from Matt Mullenweg‘s recent What a Week post:

There are decades where nothing happens, and there are weeks where decades happen.

When I returned to work, it was clear to me that it was the right time. Time to lean back into entrepreneurship and get building.

So, this past Friday, I wrapped up nearly three years at Automattic, a company like no other. I’m deeply grateful for the people I worked alongside and the opportunity to contribute to products and open-source projects that power a huge portion of the web. The level of talent, care, and thoughtfulness across the company is truly special.

This is a challenging and exciting moment for the tech industry, and I’m genuinely excited to see how Automattic continues to navigate an increasingly AI-first world. I’ll be rooting from the sidelines.

While this chapter has closed, it’s not an ending. I plan to stay involved in the WordPress ecosystem and the broader open-source community. And soon, I’ll be building in public—sharing what I’m working on, what I’m learning, and where things go next.

If you’re interested in following along, keep an eye on this blog and my social channels, notably X and LinkedIn. More to come.