How Rich Barton Built Expedia and Zillow — Audacious Goals, Provocation Marketing, and More

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.

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[00:00] Start
[00:48] Eddy Cue magic.
[01:32] Rich's morning routine and workout philosophy.
[05:44] The Breakfast Club
[09:10] How Brad Chase at Microsoft taught Rich to swing big.
[11:21] The failed DOS for Dummies book bundle project.
[14:31] Steering a company toward a culture of innovation.
[16:09] Rich's journey from management consulting to Microsoft.
[20:22] How Expedia came to be.
[28:36] Pitching and recruiting team talent.
[32:01] Degree design at Stanford.
[34:34] Realizing the value of real work as a youth.
[36:37] A fascination with Italy.
[38:00] Selling Expedia to Barry Diller/IAC.
[38:42] Dara Khosrowshahi's role in Expedia's acquisition.*
[44:06] From a post-Expedia sale sabbatical in Italy to the birth of Zillow with Lloyd Frink.
[51:03] “Big pond, good fishermen" as business criteria.
[52:12] Early Zillow mistakes.
[55:18] The Zestimate: Zillow's killer feature.
[56:41] Making lemonade from the lemons of Zillow's launch day server crash.
[58:56] Rich's provocation marketing playbook.
[01:00:39] Regulatory battles and resistance to industry disruption.
[01:05:48] Founding Glassdoor and its "give to get" data collection model.
[01:07:27] Avvo and rating attorneys — legal challenges as marketing.
[01:10:12] Digital marketplaces and Google disintermediation concerns.
[01:14:57] How Rich names companies to be memorable.
[01:22:04] Working with Benchmark Capital.
[01:25:55] What serving on a board looks like and Rich's membership criteria: "Is it local? Is it fun? Is it lucrative?"
[01:34:05] Rich's motivation and regimen for staying healthy in his 50s.
[01:42:03] Cultivating leadership through absence — the two-week disconnected trip.
[01:44:17] Building a good company by keeping good company.
[01:46:05] Developing the skill to fire people as a win/win proposition.
[01:48:55] Rich's family tattoo design and symbolism.
[01:51:36] Advice for balancing family and professional life.
[01:54:56] The benefits of distributed workforces post-pandemic.
[01:57:14] Recommended reading.
[02:06:09] Rich's billboard.
[02:09:58] The importance of sabbaticals and disconnecting from digital devices.
[02:11:42] Taking up Procreate digital art during COVID.
[02:13:09] Parting thoughts.