I rode a lot as a kid, and even worked in a bike shop in my late teens. Then life happened. Four kids later, I realized I didn’t want to end up like Uncle Rico, talking about the good old days all the time.

So I got back on the bike. That was the whole plan: ride as much as I can without sacrificing time with my family. Most times that means I’m riding while you’re sleeping.

I wanted to ride across the United States for my 40th birthday. My wife looked at our young kids and said, “once you reach the end, just keep going…” So I decided a 4 day trip was a very reasonable compromise. In 2011, a few of us rolled out of my driveway on what became the Windy 500, the annual Ride of Stupidity.

Sixteen editions later, we run our own support vehicle. No outfitter, no contracted service, just us. And I’ll be riding in it until I’m dead. Sixteen years and 70+ riders later, every single Windy has started and ended at the end of my driveway. The full history lives here.

Along the way I’ve been run over by a van, put back together, and spent most of my life fighting invisible demons. The bike is where all of that gets turned into fuel.

In 2024, I won the singlespeed 75-mile route at Gravel Worlds in Lincoln, Nebraska. In 2025, I went back and won it again. Two starts, two wins. One gear.

By day I’m National Director of Sales at Advantage+ Financing. Before that I ran MC2, Inc. in Milwaukee for 15 years. Sales is sales whether you’re closing a deal or closing a gap on a climb. Show up, do the work, don’t blink.

I got sober in September 2022. It’s part of the story, not the whole story. It shows up in how I train and how I show up for people, so it’s here.

The name of this site is the whole goal. Faster than last. Last year, last ride, last version of me.

If you’re an editor and want a sample of the writing before assigning anything, start here.

Follow the miles on Strava.

jasonkayzar@gmail.com