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How I Built This with Guy Raz

How I Built This with Guy Raz

Backroads: Tom Hale. How a desk worker became a trailblazer in active travel

Nov 3, 2025 · 55m

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About this episode

In his 20’s, working an office job he hated, Tom woke up in the middle of the night with a wild idea: why not take people on bike trips? No playbook. No investors. Just a sense that he could make a living doing what he loved. His first trip? Four guests riding through Death Valley, pitching their own tents. From there, Backroads scaled to hotels, while weathering a bike burglary, a van rollover in the desert, 9/11, the Great Recession, and a pandemic that brought tourism to a halt. Today, Backroads runs 5,000+ trips a year in 60+ countries. This is a masterclass in savvy cash flow, scrupulous quality control, and dogged iteration. If you care about travel, brand, or building a services…