In Episode E781 of How I Built This, host Guy Raz delves into the founding story of Backroads, tracing how Tom Hale transformed from a dissatisfied cubicle-worker into a pioneer in active adventure travel.
Hale recounts a moment of clarity, waking up in the middle of the night with a simple yet bold question: what if I turned my passion for cycling into guiding trips for others?
His first venture was a four-guest bike tour across Death Valley, each day covering 50 miles and camping under the stars - no luxury, no safety net. From this humble and gritty beginning, Backroads scaled into an international operation offering more than five thousand trips annually across 60-plus countries.
But the pathway wasn’t smooth. Hale reveals how the company weathered major setbacks including a van rollover in the desert, stolen bikes, the seizure of travel in the wake of 9/11, the 2008 financial crisis, and of course the pandemic.
Key to Backroads’ growth was an unorthodox but effective financial model: “collect early, pay late.” Hale explains how taking deposits upfront and strategically managing cash flow allowed the business to expand without heavy outside investment. He also emphasizes the importance of giving guests uncrowded, authentic experiences, eschewing Instagram-friendly clichés to preserve the spirit of adventure.
For the adventure travel sector, Hale’s story offers several takeaways: turn passion into purpose, build resilient operations that can survive shocks, and prioritize experience over spectacle. As the industry navigates post-pandemic recovery and evolving traveler expectations, Backroads’ journey underscores how agility and intentional design still matter.
If you’re running tours, developing product offerings, or simply seeking inspiration in travel entrepreneurship, this episode is a compelling case study in building a brand that goes the distance.