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 business at scale—listen to this.

What you’ll learn:

How a 5,000 mile solo bike trip laid the groundwork for Backroads
The first guided trip in Death Valley: four people, high winds, 50 miles/day
How to get your stolen bikes back: confront the thief yourself
The “collect early, pay late” flywheel that powered growth without investors
How Backroads survived 9/11, 2008, and COVID—and what changed after each shock
Avoiding the Instagram trap and delivering peak, uncrowded experiences

TImestamps:

7:24 – Tom’s epiphany and the eight pages of notes that started Backroads
10:15 – From cubicle to road bike: the solo trip that shaped the company’s DNA
12:46 – Trip #1: Making mistakes in Death Valley—and learning fast
24:47 – Tom’s DIY recovery operation after a warehouse burglary
29:21 – Cash without capital: spend your deposits, pay hotels later
30:55 – The Nevada rollover: walking out of the ER…and running the next trips
40:06 – Recovering after 9/11 and the financial crisis—and rebuilding the company’s value prop
45:46 – Post-COVID surge, and avoiding the tyranny of the travel selfie

This episode was produced by Casey Herman with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineers were Patrick Murray and Jimmy Keeley.

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What We Learned This Weekend