#806: How Rich Barton Built Expedia and Zillow from $0 to $35B — Audacious Goals, Provocation Marketing, Scrabble for Naming, and Powerful Daily Rituals

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 Glas