Chris Brady was selling advertising for catering companies and wedding venues when the actual business idea found him. A pizza company owner he called on casually mentioned his mobile wood-fired pizza operation, and Brady saw something click into place. He called his coworker Andrew Dana immediately. Neither of them had restaurant experience. Neither had much capital. But both wanted out of the corporate grind badly enough to take the shot.
That conversation led to Timber Pizza Co., which now operates nine locations and five mobile pizza units across the South. It’s a useful reminder that sometimes the best businesses don’t come from exhaustive planning or an MBA playbook. They come from paying attention.
Starting with Scraps and a Baby-Blue Chevy
Brady was 25 when he quit his tech sales job. His dad loaned him $15,000. He walked $5,000 of his own money to the bank. That was the capital pool. By most measures, it should have been nowhere near enough to start a restaurant business.
But a mobile pizza operation changes the math. You’re not building out a brick-and-mortar space. You’re not carrying the overhead that crushes most food startups before they gain traction. Brady and Dana drove around Washington, DC in a 1967 baby-blue Chevy pickup truck with a wood-fired oven hitched behind it, blasting hip-hop and wearing basketball shorts. They looked nothing like serious restaurateurs, which may have actually been their advantage.
“The worst thing that would have happened is that I would have had to move back with my parents and get another sales job if it didn’t work out,” Brady reflected on the early days. That psychological runway matters. When failure isn’t catastrophic, you can actually experiment instead of just executing a rigid plan.
Brady and Dana attended a pizza camp in Colorado for a weekend, bought their first oven, and figured the rest out through trial and error. The mobile model let them test ideas without the weight of a fixed location. They could move to different neighborhoods, try different events, and refine their recipe based on real feedback rather than theory.
Recognition and the COVID Pivot
By 2016, they’d opened their first retail location in Petworth, Washington, DC. The original baby-blue truck still exists, but as Brady puts it, it’s “definitely the show pony now, not the workhorse.” The business was executing well enough that Bon Appétit named them Pizzeria of the Year in 2017. A Michelin Bib Gourmand followed in 2019. They were hitting their stride.
Then COVID arrived and changed everything about how restaurants operated. In 2021, Brady and Dana brought on new partners and outside capital to stabilize the business. That capital infusion also triggered a strategic pivot: franchising. Seven years of doing business one way had to give way to a new model entirely.
“I really had to rewire my brain to go from how we had done business for the first seven years to how we were going to expand,” Brady said. That’s not a small shift. It’s the difference between building something for yourself and building something that can work without you in the room. Systems have to replace intuition. Other people’s judgment has to matter as much as your own.
Scaling Without Losing the Plot
Since 2021, Timber has grown to nine locations across the South. The expansion targets cities like Atlanta, Savannah, Greenville, and Wilmington. The goal is methodical growth, between five and eight new locations per year over the next three to five years. Brady isn’t chasing hype or explosive growth that breaks quality. He’s chasing the kind of expansion that lets each location maintain what made the original work.
That deliberate pacing reflects something you don’t hear enough from founders in growth mode: permission to move slowly. There’s a difference between scaling fast and scaling smart. Brady seems aware of that distinction.
The early years weren’t glamorous. “There were a lot of days in the first few years with some soul-crushing moments and tough times, especially when we looked at our bank account,” Brady acknowledged. Most startup memoirs skip over those parts or soften them. The fact that he’s willing to name them suggests he’s learned something durable from surviving them.
What makes this story legible isn’t the success itself. It’s the path to it: an accidental idea, minimal capital, a willingness to look ridiculous in a baby-blue truck, and enough stubborn faith to keep going when the bank account made you want to quit. The question worth asking isn’t how Brady built Timber. It’s why more people who hate their corporate jobs don’t try something similar.
