Backroads: Tom Hale. How a desk worker became a trailblazer in active travel
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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EP 129: Tom Hale (CEO, Oura) Shares Health Habits That Will Make You a Better Leader
Two weeks after Oura CEO Tom Hale started tracking and improving his sleep, he recalls, “It was like walking out of a black-and-white movie into a 4K technicolor movie… I’ve been missing this for 30 years.” The experience of feeling 20 again every day inspired him to apply for the Oura CEO role. Now, nearly 3 years into the job, he sat down to discuss what all founders and CEOs should consider when it comes to avoiding burnout and maximizing health and productivity. We covered his experiences with tools like continuous glucose monitoring, his thoughts on the future of wearables, and how AI insights will help us take better control of our health.
(00:00) Intro
(00:53) The Journey with Oura Ring
(01:47) Sleep Optimization and Health Trends
(05:06) Behavioral Changes for Better Sleep
(09:33) Tom Hale's Professional Background
(12:47) Challenges and Opportunities at Oura
(22:50) The Importance of Sleep
(26:05) Health Benefits of Quality Sleep
(28:38) Oura's Unique Position in the Market
(36:47) Consumer Choice and Healthcare Disruption
(40:59) Unexpected Insights from HSA and FSA Spending
(41:36) The Future of Insurance and Wearable Data
(44:40) Preventative Care and Employer Incentives
(47:21) The Impact of Small Choices on Health
(48:52) Artificial Intelligence in Healthcare
(54:08) The Role of Continuous Glucose Monitors
(59:50) Expanding Oura's Market and Product Strategy
(01:12:04) Navigating Leadership and Company Culture
(01:19:22) Future Opportunities and Global Expansion
(01:23:43) Closing Remarks and Reflections
Executive Producer: Rashad Assir
Producer: Leah Clapper
Mixing and editing: Justin Hrabovsky
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About the Show
Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.
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How Oura Ring is redefining health tech, with CEO Tom Hale
After using an Oura Ring helped him through a stressful transition, Tom Hale decided he wanted to help the health tracker reach new heights. Tom has led the company in a chapter of impressive growth since becoming CEO in 2022. In this episode, he sits down with host Jeff Berman to reveal how he translated lessons from his time leading software companies to innovate features, build partnerships, and more than double the number of Oura Rings sold.
Read a transcript of this episode: https://mastersofscale.com
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Oura CEO Tom Hale on Hardware-as-a-Service, navigating ZIRP, journey to CEO & more! | E1812
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Today’s show:
Oura CEO Tom Hale joins Jason to discuss his journey to becoming CEO of Oura (3:02), subscription-based business models (7:05), navigating ZIRP (39:37), the challenges of scaling a hardware business (45:00), and so much more!
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Time stamps:
(0:00) Oura CEO Tom Hale joins Jason
(3:02) Tom's journey to becoming CEO
(7:05) The significance of subscription models for business operations & product innovation
(11:28) Embroker - Use code TWIST to get an extra 10% off insurance at https://Embroker.com/twist
(12:57) Oura's subscription-based business model
(23:04) Cultivating positive habits & Oura’s advanced tracking features
(26:26) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
(27:47) Leading a company and instilling core values
(34:51) The impact of pausing marketing & harnessing the power of virality
(38:20) LinkSquares - The go-to for all your legal needs, learn more at https://linksquares.com/twist
(39:37) The ZIRP phenomenon and the challenges of scaling up
(45:00) Finding a strong product-market fit
(53:35) Merging personalization with consumer-focused approaches in healthcare
(1:03:45) Oura’s company culture
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Check out Oura: https://ouraring.com
Follow Tom: https://twitter.com/tomeghale
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#137 CEO Oura, Tom Hale: Business & Backgammon
Guest: Tom Hale, CEO of Oura
When he was growing up, Tom Hale’s family had pretty ordinary dinner-table conversations: What happened today, how was school, etc. But every day after dinner, Tom and his father would play backgammon, an experience that indirectly taught him a lot about business. Now the CEO of wearable health company Oura, he recalls that the game helped him understand risk-taking, strategy, pattern recognition, and more. Tom’s father also insisted they play for money: “If I could win 20 bucks, I could go down to the store and get something. But when I lost, I felt the sting of it. That’s the best teacher, because you’re learning the preciousness of the decisions you make.”
In this episode, Tom and Joubin discuss Tom’s radio voice, games of chance and skill, vacation rentals pre- and post-Airbnb, “irritant” service fees, health tracking, the psychology of rebranding, the consumerization of healthcare, personalized medicine, the myth of the founder-hero, rowing machines, and the meaning of work.
In this episode, we cover:
Returning to the office (00:50)
John Doerr and Macromedia (05:15)
Post-dinner backgammon (08:01)
Tom’s past jobs and HomeAway (11:31)
Competing against private startups (16:09)
How Airbnb captured demand (18:55)
Being acquired by Expedia (24:26)
What Oura’s smart rings do (26:13)
Rebranding SurveyMonkey to Momentive (29:55)
Leaving Momentive for Oura (31:54)
Making the case for himself (34:59)
The future of public health, data, and wearables (37:10)
“Sleep is strategic” (42:32)
Why Oura is an AI company (44:48)
The health impact of a taxing job (47:16)
Being a non-founder CEO (49:39)
Working with people (53:38)
What would be in a “working with Tom” doc? (54:52)
Managing the psychology of a 10-year-old startup (56:48)
Being there for family & colleagues (59:18)
Who Oura is hiring, and what “grit” means to Tom (01:02:54)
Links:
Connect with TomTwitter
LinkedIn
Connect with JoubinTwitter
LinkedIn
Email: grit@kleinerperkins.com
Learn more about Kleiner Perkins
This episode was edited by Eric Johnson from LightningPod.fm