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.&nbsp;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:<ul><li>How a 5,000 mile solo bike trip laid the groundwork for Backroads&nbsp;</li><li>The first guided trip in Death Valley: four people, high winds, 50 miles/day&nbsp;</li><li>How to get your stolen bikes back: confront the thief yourself&nbsp;</li><li>The “collect early, pay late” flywheel that powered growth without investors</li><li>How Backroads survived 9/11, 2008, and COVID—and what changed after each shock</li><li>Avoiding the Instagram trap and delivering peak, uncrowded experiences</li></ul>TImestamps:<ul><li>7:24 – Tom’s epiphany and the eight pages of notes that started Backroads</li><li>10:15 – From cubicle to road bike: the solo trip that shaped the company’s DNA</li><li>12:46 – Trip #1:&nbsp;Making mistakes in Death Valley—and learning fast</li><li>24:47 – Tom’s DIY recovery operation after a warehouse burglary</li><li>29:21 – Cash without capital: spend your deposits, pay hotels later&nbsp;</li><li>30:55 – The Nevada rollover: walking out of the ER…and running the next trips</li><li>40:06 – Recovering after 9/11 and the financial crisis—and rebuilding the company’s value prop</li><li>45:46 – Post-COVID surge, and avoiding the tyranny of the travel selfie&nbsp;</li></ul>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.Follow How I Built This:Instagram → <a href="https://www.instagram.com/howibuiltthis/" rel="noopener noreferrer" target="_blank">@howibuiltthis</a>X → <a href="https://x.com/howibuiltthis" rel="noopener noreferrer" target="_blank">@HowIBuiltThis</a>Facebook → <a href="https://www.facebook.com/howibuiltthis" rel="noopener noreferrer" target="_blank">How I Built This</a>Follow Guy Raz:Instagram → <a href="https://www.instagram.com/guy.raz/" rel="noopener noreferrer" target="_blank">@guy.raz</a>Youtube →<a href="https://www.youtube.com/channel/UCNSfrxNEmCruNtjIzxCBHjg" rel="noopener noreferrer" target="_blank"> guy_raz</a>X → <a href="https://x.com/guyraz" rel="noopener noreferrer" target="_blank">@guyraz</a>Substack →<a href="https://urldefense.com/v3/__http:/guyraz.substack.com__;!!Iwwt!RZoD751oWzUzoqqdJiqaoL6HdJfRHDUO1TKvYJ424d3Udn7-Pw9Nj6nEsauh9zcgEvLjUEc$" rel="noopener noreferrer" target="_blank"> </a><a href="http://guyraz.substack.com" rel="noopener noreferrer" target="_blank">guyraz.substack.com</a>Website →<a href="https://urldefense.com/v3/__http:/guyraz.substack.com__;!!Iwwt!RZoD751oWzUzoqqdJiqaoL6HdJfRHDUO1TKvYJ424d3Udn7-Pw9Nj6nEsauh9zcgEvLjUEc$" rel="noopener noreferrer" target="_blank"> </a><a href="http://guyraz.com" rel="noopener noreferrer" target="_blank">guyraz.com</a>See Privacy Policy at <a href="https://art19.com/privacy" rel="noopener noreferrer" target="_blank">https://art19.com/privacy</a> and California Privacy Notice at <a href="https://art19.com/privacy#do-not-sell-my-info" rel="noopener noreferrer" target="_blank">https://art19.com/privacy#do-not-sell-my-info</a>.

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