Podcast Summary: How I Built This with Guy Raz
Episode: Backroads - Tom Hale. How a desk worker became a trailblazer in active travel
Air Date: November 10, 2025
Episode Overview
In this episode, Guy Raz interviews Tom Hale, founder and CEO of Backroads, the world’s largest active travel company. Tom shares his journey from a disillusioned environmental planner and desk worker in Las Vegas to pioneering the concept of guided group bike tours—eventually expanding Backroads into a global operation. The conversation explores Hale’s moments of doubt, grit, evolution of the company, navigating disasters like 9/11, the 2008 recession, and COVID-19, and the personal philosophies that fuel his ongoing success.
Key Discussion Points & Insights
Early Influences & Inspiration
[02:32 – 07:53]
- Tom grew up loving the outdoors and track running, but injuries shifted him from running to biking.
- His first non-outdoors job (environmental planning in Las Vegas) was uninspiring:
“Tom, you are somebody that needs to be passionate about what you're doing. ... I made the wrong decision.” (Tom Hale, 05:18)
- After six months in a desk job, Tom had a "midnight epiphany" to start bike tours.
- Inspired by “What Color Is Your Parachute?” and personal values around independence, excitement, and control.
The Birth of Backroads
[07:53 – 13:32]
- Tom quit his job outright, with little money or planning:
“I quit my job, had no income coming in. So I was going to make something out of this.” (Tom Hale, 09:12)
- He embarked on a 5,000-mile solo bike trip around the Western US to research and reflect.
- First organized trip: 4 guests, camping in Death Valley. They all pitched tents and cooked but learned quickly guests wanted more comfort (“...that could not have been more ill-founded, personally.” – 13:37)
- Early pricing was trial and error, often too low, financed by Tom’s side job scraping cheese at a fondue restaurant.
Operations in the Early Days
[13:32 – 22:05]
- Trips ran as point-to-point loops across the West: New Mexico, Colorado, Wyoming, etc.
- Bikes were stored in a shared house’s garage with roommate Norwegians.
- Tom’s first partner, Linda Petty, joined after meeting on Tom’s bike trip but left after 2.5 years due to the grind.
Growth, Risk, and Resilience
[27:04 – 35:14]
- Early setback: a burglary at the warehouse (half the bikes stolen—but Tom got most back after confronting the thieves himself).
- Logistics were complex but learned through notepad-tracking and constant iteration.
- Business finances were managed without outside investment, aided by a favorable cash flow model: guests paid deposits well in advance, while hotels were paid post-service.
Close Calls & Pivots
[33:05 – 35:14]
- A major van rollover accident (Nevada desert):
“We rolled the van a couple times...it was all steel tool chests, propane containers... we're Spiderman-ing through the air.” (Tom Hale, 33:05)
Despite injuries, the team pressed on with upcoming trips, demonstrating Hale’s tenacity and resourcefulness.
Expansion & Professionalization
[35:14 – 40:05]
- Shifted from only Western US and camping to Hawaii, Baja, New Zealand, and Bali by the mid-1980s.
- Developed formal staff training and performance management over time.
- Early focus: biking, then added hiking and multi-adventure offerings. Now, the business is split roughly a third each.
Surviving Major Global Crises
[43:07 – 48:15]
- 9/11 (2001): Disrupted travel industry and peak season. Backroads encouraged guests and leaders to continue if they felt safe; “amazingly great trips run that week.”
- Financial Crisis (2008-09): Business dropped 43%. Retooled company by emphasizing unique strengths, increased quality (more leaders per trip, etc.), improved profit margins.
- COVID-19 Pandemic:
“We basically stopped all revenue for about a year... But we came out of COVID faster than anybody... our guests were just so darn happy to be outside and doing something with people that we shot up in business in 2022 like you can't even believe.” (Tom Hale, 46:39; 48:15)
Reflections on Growth, Technology, and Travel Culture
[49:53 – 53:14]
- Tom laments the rise of “Instagram tourism” and crowds but notes Backroads’ focus is different:
“That's not the part of travel we do... we're biking... on little towns... it's not an Instagram-heavy environment.” (Tom Hale, 49:53)
- Embracing technology cautiously (“AI can be an efficiency tool, but our voice has to remain ours” – 52:33).
- Backroads now offers over 5,000 trips annually, employs 1,300+ people, and maintains a high repeat/referral rate.
Final Reflections on Hard Work vs. Luck
[53:41]
- Tom attributes his success partly to “a fortuitous moment,” but mostly to hard, relentless work:
“The grind has been consistent, non-stop, embraced and has meant everything. And I don’t resent it, I embrace it.” (Tom Hale, 53:41)
- Contrasts his experience with hobbyists—full commitment was essential.
Notable Quotes & Memorable Moments
- On quitting his desk job:
“I wasn’t going to make that mistake again.” (Tom Hale, 09:51)
- On the first Death Valley trip:
“We had four people on it... couldn’t have done more things wrong... but we had a good time.” (Tom Hale, 12:57)
- On the van crash:
“We came to a rest... Bill, one of the leaders, said, well, I guess that's it for the summer. And didn't miss a blink. It's like my response: well, I don't think so. We'll figure it out.” (Tom Hale & Guy Raz, 33:05)
- On the power of word-of-mouth:
“Word of mouth is everything in this business. You can't do it without word of mouth.” (Tom Hale, 39:51)
- On resilience after crises:
“We're going to come out of this stronger than when we went into it.” (Tom Hale, 47:07)
- On staff and leadership:
“More than anything else we do, we have the best leaders out there and we treat them well... We just don't subcontract.” (Tom Hale, 45:13)
Key Timestamps for Important Segments
- 02:32 - Tom’s early life, Las Vegas job, and parental influence
- 07:04 - Midnight epiphany, quitting his job, birth of Backroads
- 10:33 - 5,000-mile research bike loop
- 12:57 - First ever guest trip (Death Valley)
- 16:45 - Transition from camping to hotel-based trips
- 19:19 - Early operations and logistics, living with Norwegians
- 27:04 - Bike theft episode and confrontation
- 33:05 - Van rollover accident; resilience in crisis
- 35:40 - International expansion (Hawaii, New Zealand, Bali)
- 43:07 - Impact of 9/11
- 44:13 - Surviving the 2008 financial crisis
- 46:39 - COVID-19 and rebound
- 49:53 - Social media's impact on travel; Backroads’ unique approach
- 52:33 - Technology/AI in travel
- 53:41 - Reflections on what drives business success
Conclusion
This episode offers a riveting look into how Tom Hale turned a “random” 2 a.m. idea into a category-defining company, withstanding the unpredictability of entrepreneurship and global crises, while staying true to the roots of authentic, people-driven adventure. Hale’s story provides rich lessons on grit, finding your path, building something sustainable from scratch, and the value of embracing hard work over shortcut strategies.
Original tone: Warm, candid, humorous, with the practical wisdom and storytelling ease typical of Guy Raz’s interviews.