April 16, 2025
#806: How Rich Barton Built Expedia and Zillow from $0 to $35B — Audacious Goals, Provocation Marketing, Scrabble for Naming, and Powerful Daily Rituals
The Tim Ferriss ShowAbout this episode
Rich Barton is the co-founder 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. Sponsors: Ramp easy-to-use corporate cards, bill payments, accounting, and more: https://ramp.com/tim (Get $250 when you join Ramp) Cresset prestigious family office for CEOs, founders, and entrepreneurs: https://cressetcapital.com/tim (book a call today) Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business: https://shopify.com/tim (one-dollar-per-month trial period) Timestamps: [00:00:00] Start. [00:05:30] Eddy Cue magic. [00:06:14] Rich’s morning routine and workout philosophy. [00:13:38] How Brad Chase at Microsoft taught Rich to swing big. [00:15:46] The failed DOS for Dummies book bundle project. [00:18:52] Steering a company toward a culture of innovation. [00:20:26] Rich’s journey from management consulting to Microsoft. [00:24:34] How Expedia came to be. [00:32:32] Pitching and recruiting team talent. [00:37:18] Degree design at Stanford. [00:39:45] Realizing the value of real work as a youth. [00:41:44] A fascination with Italy. [00:43:01] Selling Expedia to Barry Diller/IAC. [00:43:51] Dara Khosrowshahi’s role in Expedia’s acquisition. [00:45:23] From a post-Expedia sale sabbatical in Italy to the birth of Zillow with Lloyd Frink. [00:55:41] “Big pond, good fishermen” as business criteria. [00:56:50] Early Zillow mistakes. [01:00:05] The Zestimate: Zillow’s killer feature. [01:01:29] Making lemonade from the lemons of Zillow’s launch day server crash. [01:03:49] Rich’s provocation marketing playbook. [01:05:30] Regulatory battles and resistance to industry disruption. [01:10:44] Founding Glassdoor and its “give to get” data collection model. [01:12:58] Avvo and rating attorneys — legal challenges as marketing. [01:16:11] Digital marketplaces and Google disintermediation concerns. [01:19:52] How Rich names companies to be memorable. [01:25:28] Why Rich recommends leaving fear out of the provocation marketing equation. [01:26:48] Working with Benchmark Capital. [01:30:37] What serving on a board looks like and Rich’s membership criteria: “Is it local? Is it fun? Is it lucrative?” [01:39:00] Rich’s motivation and regimen for staying healthy in his 50s. [01:47:13] Cultivating leadership through absence — the two-week disconnected trip. [01:49:34] Building a good company by keeping good company. [01:51:42] Developing the skill to fire people as a win/win proposition. [01:54:41] Rich’s family tattoo design and symbolism. [01:57:29] Advice for balancing family and professional life. [02:01:08] The benefits of distributed workforces post-pandemic. [02:03:23] Recommended reading. [02:12:17] Rich’s billboard. [02:14:25] The importance of sabbaticals and disconnecting from digital devices. [02:17:41] Taking up Procreate digital art during COVID. [02:19:05] Parting thoughts. * For show notes and past guests on The Tim Ferriss Show , please visit tim.blog/podcast . For deals from sponsors of The Tim Ferriss Show , please visit tim.blog/podcast-sponsors Sign up for Tim’s email newsletter ( 5-Bullet Friday ) at tim.blog/friday . For transcripts of episodes, go to tim.blog/transcripts . Discover Tim’s books: tim.blog/books . 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