#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 (zillow.com), 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.
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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.
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