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What if the best IT work is the stuff you don’t even notice—no drama, no heroics, just things quietly working the way they should? That’s Gary’s story. He went from fixing his school’s computers as a teenager to running AnyIT, a managed service provider built on reliability, compliance, and actual human support. We talk about the real day-to-day behind IT, why “have you tried turning it off and on again?” is secretly great advice, and how the cloud has raised the stakes when things break.

But Gary’s world isn’t just help desks and servers. Through the Stowmarket Flyer he got plugged into the local business scene, and that same mindset—plan for resilience, cut single points of failure, let small wins add up—took him into property too. Renting out rooms, providing internet, and eventually buying the whole building turned into a kind of “practical pension.” It’s all very Gary: steady, no-fuss, and quietly clever.

This chat is funny, honest, and packed with insights about why reliable systems are the hidden engine behind creativity—and why the quiet path usually comes out on top.

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