Welcome to Tales from the Server Room

Over 20 years of building software for MSPs, a lot has happened.

Some of it was funny. Some of it was terrifying. Most of it was both at the same time.

I started at ConnectWise in the year 2000 — before MSPs were called MSPs, before the cloud existed, before anyone had heard of AWS. We brought servers onto planes. We accidentally took down a city's internet connection. We ran customer data on a dev machine named HAL for months without knowing it. We discovered S3 on hour three of a 75-day deployment.

And then I left to start Nine Minds, and a whole new set of stories began.

Tales from the Server Room is where I'm collecting the ones worth telling. The real version — not the polished retrospective, but the version where I'm staring out a window wondering how things got this bad, or watching a progress bar that says 70 days remaining suddenly drop to zero.

If you work in tech, or you're building something, I think you'll recognize these moments. The contrast between the world-historical and the mundane. The gap between what you planned and what actually happened.

Stick around. There are more stories where these came from.