I write about bikes, brothers, and the annual Ride of Stupidity. I’m the founder of the Windy 500, an unsupported multi day ride now in its 16th year. Two time Gravel Worlds singlespeed champion, 2024 and 2025. Full bio is here.
If you’re an editor and want a sample of my writing, these are the four to read. Same ride, from and back to my driveway, sixteen years running.
2026 – Year 16
Sixteen years in, the ride starts asking different questions. This one looks back at the whole thing without flinching.
2025 – Year 15
The origin story: flat tires, wrong turns, no plan B, chasing the sunset on the very first ride in 2011. Fifteen years later the same ride runs on rails, and that’s its own kind of win.
2024 – Year 14
Old friends, an aging body, and two years of sobriety, all colliding on a bike over four days. The most personal wrap up in the archive.
2023 – Year 13
Seventy plus riders across thirteen years. A look at what actually holds a tradition like this together, and why most people never make it past year one.
Everything else
All sixteen years, start to finish, live here.
jasonkayzar@gmail.com
...Faster than Last 