I’m Chris Tomshack

Cleveland born and raised. Spent a few years living in Australia (Gold Coast) and London before landing in Chicago about a year and a half ago.

I played collegiate baseball on a scholarship, went back to school for software engineering, and co-founded two companies — both of which I’ve since exited. Along the way I built a YouTube channel past 60K subscribers, worked with brands like Insta360, Garmin, and Coca-Cola, earned my USPA skydiving coach and videographer ratings, finished three Ironmans, and became a sponsored cyclist riding for Dragonspine Cycling on Factor bikes.

In August 2026 I’m riding from Chicago to New York City. Rapha is one of the sponsors, which still hasn’t fully sunk in.

This is where I put everything worth sharing — guides, gear, and whatever I pick up along the way.