Nov 10, 2025 · 50m · how-i-built-this
Backroads: Tom Hale. How a desk worker became a trailblazer in active travel
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In this episode of How I Built This, host Guy Raz interviews Tom Hale, founder of Backroads, detailing how he transformed a midnight epiphany and a solo 5,000-mile cycling reconnaissance trek into one of the world's leading luxury active travel companies without taking outside venture capital.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 41.7% of the talking time here. How this is scored →
Guy as informed peer 2.0 Guest teaching 1.7 Guest disagreement 0.4 Guy pushing back 0.5
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 41:04 Tom Hale refutes tourist-trap assumptions
Hale directly rejects Raz's broad characterization of modern European tourism, asserting that Backroads guests avoid crowded tourist hubs and ride solitary routes through small villages.
Hardest push from Guy ▶ 41:14 Guy Raz challenges Hale on avoiding major destinationsRaz interrupts Hale's defense to argue that travelers inevitably cannot avoid iconic tourist destinations like Florence when traveling to Europe.
Biggest teaching moment ▶ 30:58 Tom Hale details rigorous guide developmentHale refutes Raz's assumption that tour guides simply learned on the fly, breaking down their intensive 10-day training and metric-driven performance evaluations.
Guy holds their own ▶ 40:10 Guy Raz on social media degrading travel cultureRaz delivers a detailed observation contrasting 1990s backpacking with modern Instagram selfie-seeking and disproportionate wait lines for food over art museums.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Las Vegas Planning Job and Mismatched Passions | 1 | 1 | 0 | 0 | Guy Raz gently probes Tom Hale's transition from an uninspiring environmental planning desk job in Las Vegas to a sudden late-night inspiration to start a bike touring company. Hale explains how mismatched his personality was for municipal desk work in a collaborative, reflective tone. | |
| Going All-In Without a Backup Plan | 2 | 2 | 1 | 1 | Hale rejects Raz's framing that he could easily fall back on a desk job, emphasizing that quitting was a total commitment. They briefly banter over the pronunciation and packing of bicycle panniers during Hale's solo 5,000-mile western loop. | |
| Embracing Solitude and National Park Potential | 1 | 2 | 0 | 0 | Hale educates Raz on the rough realities of early commercial trips, such as camping in Death Valley winds and cracking Dutch ovens on charcoal briquettes. Raz marvels at how early customers essentially paid to pitch their own tents and ride 50 miles a day. | |
| Subsidizing the Startup at Fondue Fred | 2 | 1 | 0 | 1 | Raz expresses amusement and minor skepticism over Hale's side job chipping cheese pots at Fondue Fred to fund print ads. Hale details the rapid shift from camping trips to upscale hotel stays after customer demand shifted. | |
| Modest Beginnings in an Oakland Garage | 2 | 1 | 0 | 0 | Hale details operating Backroads out of an Oakland garage shared with Norwegian roommates for $135 monthly rent. Raz tracks the linear logistics of driving vans and bikes across continuous western state circuits. | |
| Partnership and Parting with Linda Petty | 1 | 1 | 0 | 0 | Hale recounts parting ways with early partner Linda Petty and personally confronting a neighborhood burglar to retrieve a dozen stolen bicycles. Raz follows the storytelling with supportive prompts. | |
| Analog Logistics and Welcoming Mixed Abilities | 2 | 2 | 0 | 0 | Hale clarifies that Backroads succeeded by tailoring trips to mixed fitness levels rather than elite cyclists, explaining his analog note-taking logistics before digital systems existed. | |
| Cash Flow Mechanics and Financial Self-Reliance | 3 | 2 | 1 | 0 | Hale outlines the negative cash-conversion cycle ('collect early and pay late') that funded Backroads without venture capital. He also recounts surviving a severe van rollover crash in Nevada and finishing the summer season despite broken ribs. | |
| Venturing Abroad: Hawaii, New Zealand, and Beyond | 2 | 2 | 0 | 0 | Raz inquires about international expansion to offset seasonality. Hale explains shipping proprietary gear and dispatching trained North American trip leaders to early destinations like Hawaii, New Zealand, and Bali. | |
| Establishing Professional Leader Training and Rigorous Surveys | 2 | 3 | 1 | 1 | When Raz assumes leaders were trained simply on the fly, Hale corrects him by outlining Backroads' intensive 10-day training protocol and exhaustive customer satisfaction metric tracking. | |
| Mid-Show Break: Resilience Through Industry Crises | 2 | 2 | 0 | 0 | Hale explains weathering 9/11 and the 2008 financial crisis (a 43% revenue drop) by increasing staffing ratios, upgrading vans, and treating leaders as payroll employees rather than gig contractors. | |
| Navigating COVID-19 Disruptions and Explosive Recovery | 1 | 1 | 0 | 0 | Hale discusses navigating total travel shutdowns during COVID-19 with boxed meals and payroll adjustments, leading into an unprecedented rebound in 2022 across 5,000 annual trips. | |
| Authenticity in Travel Versus Social Media Tourism | 6 | 4 | 3 | 4 | Raz presents an extended critique of modern social media tourism, citing empty European museums alongside two-hour gelato queues. Hale firmly counters Raz's premise, stating Backroads trips intentionally bypass tourist traps to cycle remote backroads at individual paces. | |
| Integrating Technology and Artificial Intelligence | 3 | 2 | 0 | 0 | Raz and Hale discuss utilizing artificial intelligence for travel efficiency while preserving brand voice, followed by Hale reflecting on sustained hard work versus initial luck. | |
| Episode Outro, Credits, and Acknowledgements | 0 | 0 | 0 | 0 | Episode credits followed by a sponsored segment featuring Stephen Davis of Takeoff Luggage describing his removable-wheel suitcase innovation for budget flights. |
Statements from this episode (16)
Hale: Loving the outdoors does not translate to enjoying environmental planning
“I see so many kids Doing exactly what I did, which is I love the environment, ok? I always have. I've been running out in the woods all my life. I love the environment. Well, I love the environment, so why don't I do environmental planning? There was nothing a…”
Hale drafted an eight-page Backroads business plan at 2 a.m.
“Woke up about two in the morning, got out of bed, and took eight pages of notes on what it would take to do this.”
Hale: I rode a 5,000-mile western US solo loop to scout Backroads routes
“I thought the, you know, going around the loop in the western United States, I did about a 5000 mile loop. I started in San Francisco, took BART to the end of the line, and got out of BART, and rode down the coast, and Went counterclockwise around the country,…”
Hale: Active travel tour guests absolutely do not want to pitch tents
“In the very beginning, I believe we felt like it was a good thing to have people participate. I think that could not have been more ill-founded personally, but so they did actually Pitch their tent. And anyway, it didn't take us very long to realize that they …”
Hale worked night shifts chipping cheese from pots to fund early ads
“Well, they didn't cost very much, and I worked on the side at night at Fondue Fred on Telegraph Avenue in Berkeley. I chipped the cheese out of fondue pots.”
Hale: Backroads was burglarized in San Leandro, losing half its bikes
“The bikes were in our warehouse in San Leandro. We got burglarized, and they stole half of our bikes.”
Hale: Backroads remained family-owned without outside investors for 46 years
“Didn't have any investors, never, it's remained a hundred percent closely held family business for 46 years”
Backroads collects deposits 90 days early and pays hotels post-trip
“Our guests first of all are paying their deposit Maybe 90 days in advance or more on average. We are paying the hotel. Sometimes the balance due is paid after we have already finished the trip.”
Hale: Trip leaders finished the summer season despite a vehicle rollover crash
“But they Bill and Kathy went on to lead the next two trips. I went back to get another van to meet them, and we finished it was a pretty rigorous, because we had to keep moving the seats in the van in and out, and they were heavy, and we had to move big, heavy…”
Hale: Early international Backroads tours likely ignored local regulations
“My guess is they probably did have rules and we probably weren't adhering to them.”
Hale: Backroads customer acquisition is one-third repeat, referral, and new
“We have a very high repeat and referral rate That's also about one third, repeat, referral, and new business.”
Hale: Backroads suffered a 43% drop in business during the 2008 crisis
“We had a 43% drop in business that year.”
Hale: Backroads will operate more than 5,000 active travel trips this year
“We'll do about a little over 5000 trips this year.”
Hale: Backroads avoids or drops destinations compromised by overtourism
“We do our best to avoid those kinds of places. Sometimes we're able to go in the morning and miss something that negative aspect of a place. And sometimes we just don't go there anymore.”