1 Year and 6 Days

As of today, January 12, 2025, that’s how long it’s been since I left Ollama. That day was a bit of a shock. But I’ve been here before - years ago, I left Microsoft when I saw my future there was limited. That leap led me to Amsterdam, then to startups in Boston, and eventually to Datadog.

Let me back up. In 2023, I did something that probably seemed crazy to a lot of people - I left Datadog after being there since the early days. I started the entire community ecosystem there: docs, developer evangelism, training, community teams - watching those grow from nothing into full-fledged organizations. When Datadog went public, it wasn’t just another IPO - it was labeled a unicorn and became one of tech’s biggest success stories. By the end, I was deep into creating Kubernetes training courses, and I got excited when I heard about what this team was working on. These weren’t just any developers - they were the folks behind Kitematic, the first UI frontend for Docker. Anyone who was around in the early container days remembers what a game-changer that was.

Being early at Datadog had set us up well - we’d bought our dream home on Bainbridge Island, Washington. I could’ve just kicked back and enjoyed island life. But after years of building communities and teaching developers, I was itching to build something new.

The company was called InfraHQ back then - a YC-backed startup with big infrastructure dreams. It was tiny - just eight people when I joined as their evangelist, and I was the only non-engineer on the team. We ended up pivoting twice: first to SSH tools, and then to an AI project that really caught fire. That’s when we became Ollama. And holy cow, did it take off - the project was already a rocket ship when I was there, and it’s only accelerated since. 

But here’s the thing - despite being there for those early days and pivots, I’m not part of Ollama anymore. I got let go while we were still that small eight-person team, even as things were starting to explode. That’s startup life for you - sometimes you help plant the seeds but don’t get to stick around to see the garden grow. The day I left became day one of my next chapter - going all in on YouTube. I was making just $18 a month at the time, but I’d always dreamed of doing it full time. Now, a year later, I’m about to hit 50,000 subscribers, my videos regularly pull in 10,000 views within days of posting, and I just landed my first sponsorship. 

Look, I won’t lie - getting let go still stings, and watching Ollama’s success from the outside isn’t always easy. In an ironic twist, my YouTube channel now largely focuses on teaching people how to use Ollama, helping them understand the product and its capabilities. Maybe I’m still doing developer evangelism after all, just from a different angle.

So yeah, that’s the deal. I’m not involved with Ollama now, but it’s been wild watching something I was part of become this huge thing in the dev community.