THE RIDE
A 3,500-mile gravel ride from Canada to Mexico. A comedy tour through six states. A documentary about chasing a dream before it becomes a regret.
“Most meaningful things in life begin before you're ready.”
The Ride
A few years ago, if you had told me I'd be preparing to ride a bicycle 3,500 miles across the Great Plains, I'd have laughed.
I wasn't a cyclist. I didn't race bikes in high school. I didn't discover endurance sports in college.
Then somewhere along the way, I found a gravel bike.
What started as short rides around the neighborhood grew into long rides from town to town, and eventually led me to the Great Plains Gravel Route — 3,500 miles of dirt roads, small towns, endless skies, prairie winds, and uncertainty stretching from Canada to Mexico.
The kind of thing a sensible person hears about and immediately forgets. Instead, I couldn't stop thinking about it.
What it’s about…
“The possibility of failure is less frightening than the possibility of regret.”
Why I’m Doing It
Every reason not to do it showed up right on schedule.
I'm 47. I've only been riding for a couple of years. The route is remote. The outcome is uncertain. The whole thing seems just difficult enough to make people tilt their head and ask, "Are you sure that's a good idea?"
I've learned that's usually a sign I'm paying attention to the right thing.
What finally pushed me toward saying yes wasn't confidence. It was the realization that confidence is overrated. Most meaningful things in life begin before you're ready.
You start because the idea won't leave you alone.
You start because the dream keeps showing up, no matter how much you push it away.
You start because one day you realize the possibility of failure is less frightening than the possibility of regret.
I don't want this ride to become a regret.
I want the adventure. I want the uncertainty. I want the stories. I want to spend time beneath those enormous prairie skies and find out what happens when I stop waiting.
The Documentary &
Comedy Tour
After one of my comedy shows in Kansas, I found myself talking with some folks about the ride.
The next day, I got a call asking if I'd be interested in turning the bike adventure into a documentary and comedy tour.
It was one of those moments where life suddenly gets bigger than the plans you've been making for it.
So now this thing has become more than a bike ride. It's a documentary. It's a comedy tour. It's an opportunity to travel through six states collecting stories, meeting strangers, and exploring what happens when an ordinary person commits to something great that also seems a little unattainable.
“It was one of those moments where life suddenly gets bigger than the plans you've been making for it.”
How You Can Join Me
Maybe that's what this ride is really about. Not crossing a finish line. Not proving anything. Just saying yes, and showing up for the dream.
If you'd like to follow along, I'd love to have you.
Come to a show. Ride a few miles with me. Track the journey. Share a story. Support the documentary if you're able. Or simply watch from afar and see what happens when a middle-aged comedian points a bicycle toward the horizon and decides to trust the road.
3500
Miles
6
States
6
Shows
North Dakota | South Dakota | Nebraska | Kansas | Oklahoma | Texas
Follow the Ride
Track the ride, catch a show, or follow along from wherever you are.