#806: How Rich Barton Built Expedia and Zillow from $0 to $35B — Audacious Goals, Provocation Marketing, Scrabble for Naming, and Powerful Daily Rituals
Episode
145 min
Read time
2 min
Topics
Career Growth, Productivity, Health & Wellness
AI-Generated Summary
Key Takeaways
- ✓Intrapreneurship Strategy: Barton pitched Expedia as an HR experiment to retain entrepreneurial talent at Microsoft, spinning out 150 employees who would have left otherwise. He secured $100 million in advertising budget by arguing public markets would fund it essentially free during the 1999 bubble, demonstrating how to leverage market conditions for internal ventures.
- ✓Provocation Marketing Framework: Build features around emotionally charged topics (seven deadly sins zone) that address taboos or sacred cows, but ensure they make people feel good rather than scared. Examples include Zillow's home value estimates, Glassdoor's salary transparency, and Avvo's attorney ratings—all designed to generate organic conversation and media coverage without traditional advertising spend.
- ✓Company Naming System: Use high-point Scrabble letters (Z, X, Q worth 10 points) for distinctiveness, limit to two syllables maximum, ensure it works as a dog name and verb, include double letters or palindromes. This creates memorable, ownable brand equity versus generic descriptive names like hotels.com which lack defensible positioning.
- ✓Strategic Defense Against Google: Avoid dependency on Google traffic by building direct brand recognition and embedding into industry workflow. Create tools that become integral to transactions rather than just lead generation middlemen. This prevents disintermediation when platforms like Google move vertically into your business model, as happened with travel and review sites.
- ✓Failure Recovery Culture: After Barton's $10-20 million MS-DOS book bundle failure at Microsoft, his boss Brad Chase asked what his next big idea was instead of punishing him. This approach—protecting innovators from corporate immune system rejection while maintaining accountability—became Barton's hiring and retention philosophy for identifying intrapreneurs who drive company growth.
What It Covers
Rich Barton shares how he built Expedia and Zillow from zero to $35 billion combined valuation, detailing his provocation marketing strategy, naming methodology using high-value Scrabble letters, internal Microsoft venture funding approach, and daily rituals including morning routines and fitness habits.
Key Questions Answered
- •Intrapreneurship Strategy: Barton pitched Expedia as an HR experiment to retain entrepreneurial talent at Microsoft, spinning out 150 employees who would have left otherwise. He secured $100 million in advertising budget by arguing public markets would fund it essentially free during the 1999 bubble, demonstrating how to leverage market conditions for internal ventures.
- •Provocation Marketing Framework: Build features around emotionally charged topics (seven deadly sins zone) that address taboos or sacred cows, but ensure they make people feel good rather than scared. Examples include Zillow's home value estimates, Glassdoor's salary transparency, and Avvo's attorney ratings—all designed to generate organic conversation and media coverage without traditional advertising spend.
- •Company Naming System: Use high-point Scrabble letters (Z, X, Q worth 10 points) for distinctiveness, limit to two syllables maximum, ensure it works as a dog name and verb, include double letters or palindromes. This creates memorable, ownable brand equity versus generic descriptive names like hotels.com which lack defensible positioning.
- •Strategic Defense Against Google: Avoid dependency on Google traffic by building direct brand recognition and embedding into industry workflow. Create tools that become integral to transactions rather than just lead generation middlemen. This prevents disintermediation when platforms like Google move vertically into your business model, as happened with travel and review sites.
- •Failure Recovery Culture: After Barton's $10-20 million MS-DOS book bundle failure at Microsoft, his boss Brad Chase asked what his next big idea was instead of punishing him. This approach—protecting innovators from corporate immune system rejection while maintaining accountability—became Barton's hiring and retention philosophy for identifying intrapreneurs who drive company growth.
Notable Moment
Barton's son was born on the exact day Expedia went public in November 1999. His wife, an OBGYN who understood labor timing, woke him at 3 AM asking if she really had to name their baby Expedia as he had jokingly promised the team, creating a memorable intersection of professional triumph and personal milestone.
Episode Transcript
Hey, folks. Tim here. My best selling card game, Coyote, which I made with the amazing team at Exploding Kittens, just won the Pop Insider best geeky game of 2025 and also best stocking filler in the made for moms toy awards '20 twenty '5. It is on sale everywhere. It's cheap. It's fast to learn. It has 4.8 stars out of five. People are loving it. Coyotegame.com will take you to all the retailers, but you can find it everywhere. It is a game of thinking fast and laughing faster. Think charades meets hot potato meets a bunch of brain fun. It's good for your head. It's perfect for families with kids age 10 or adults who are kids at heart or don't take themselves too seriously. A lot of adults love this game. And as I said, it's available everywhere. Amazon, Walmart, Target, 8,000 plus retail locations, you name it. So please check it out. I loved making it. People are really enjoying it. It has 300 or 400,000,000 plus social views of gameplay online. And try it, enjoy it this holiday season. Check it out, coyotegame.com one more time. That's coyotegame.com or anywhere you buy your games. Now back to the episode. Hello, boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode of the Tim Ferriss Show, where it is my job to deconstruct world class performers, people who are arguably the best at what they do. How do they do it? What are their influences? Favorite books, frameworks, lessons learned, things that you can apply to your own life. And I have someone you may not have heard speak before on the podcast today. Rich Barton, close friend of Chris Sacca and some other guests we've had. He is the cofounder and co executive chairman of Zillow, a company transforming how people buy, sell, rent, and finance homes. Before Zillow, Rich founded Expedia within Microsoft in 1994 and successfully spun the company off as a public company in 1999. He served as president, CEO, and board director of Expedia, and later co founded and served as non executive chairman of Glassdoor. He has done so many different companies, and he has a lot of stories from the trenches, a lot that you can use that is tactical and practical. He's also super fit, super active. I would say a great father and husband. He is an incredible human being, sort of full stack. And that's part of the reason I really wanted to have him on the show. We did it in person. We covered a lot of ground, and I think you're gonna enjoy it. I loved it. So with just a few words from the people who make this podcast possible, we'll get straight to the meat and potatoes and a wide ranging conversation with none other than Rich Martin. My first book, The Four Hour Workweek, which made everything else possible, is built around the acronym and framework …
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