Why I Started Grindsboro Running

I sometimes miss the Atlanta Beltline. But, Greensboro’s trails have so much wildlife.

A note about running, systems, and starting anyway.

By day, I build systems.

My full-time job is in agency operations—designing efficient workflows, automating processes, and removing friction. The goal is to save time, minimize waiting, and let people do more with less. Right now, I spend my days deep in ClickUp, AI, and Zapier, stringing tools together so people can collaborate just enough to get the job done.

And I love parts of that. I love when people come together to solve something. I love creating space for strategy and connection, even if most of my work happens alone, behind a screen, three states away from anyone on my team.

But over the years, it’s started to wear on me. I still love what I do, and don’t dream of quitting. But I need more.

When your whole job is making things happen without interaction, when your whole week happens inside a computer… it’s easy to forget what it feels like to do something real. Something with people. Something you can see and feel and touch at the end of the day.

That’s where Grindsboro Running started.

It wasn’t a big plan. It was a quiet itch. A YouTube video playing in the background. Hank Green talking about how some of the best things he’s done were also the weirdest, riskiest ones—ideas he wouldn’t recommend from a business perspective, but still wouldn’t trade for anything.

And I realized: I’ve been holding back. Not just from Grindsboro, but from all of it—Bellhollow, Wyrdstead, the barter market, the idea of backyards full of strangers learning from someone’s grandma. I’ve had these visions for years, but I also have a business degree and a very practical voice in my head used to say, what if it fails? What if it becomes too much? What if I’m the only one that actually wants this?

But lately, another voice has taken over:
What if it matters? What if it works?

Grindsboro started as a response to something simple. I love running—but most run clubs in town meet at breweries. I don’t dislike breweries, but I rarely drink. I wanted something different. I wanted coffee. I wanted cake. I wanted a place for runners (and maybe-walkers and maybe-talkers) to gather without the pressure to drink or perform.

And I didn’t want to be the center of it. That’s the truth. I’ve always been the type to build things quietly and let them run on their own. But somewhere along the way—leading teams, teaching tools, speaking at off-sites—I stopped being afraid to be seen. Or maybe I just got tired of waiting for someone else to start.

So I did it.

Grindsboro is a weird little running club that meets at coffee shops, dessert bars, and indie spots around Greensboro. There’s no pressure. No paces. No membership forms. Just a chance to move, meet, and support the local businesses we actually want to see thrive.

And yeah—it’s small. It’s early. It might not work forever.
But it’s real. And it’s where this all began.

Sometimes the best place to start building something big is by running a few miles with strangers, then splitting a cinnamon roll and staying for conversation.

That’s how Wyrdstead started.
One run. One donut. One un-automated moment at a time.