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. This episode is brought to you by: 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) Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 900 million downloads and been selected for “Best of Apple Podcasts” three years running. Sign up for "5-Bullet Friday" (Tim's free weekly email newsletter): https://go.tim.blog/5-bullet-friday-yt/ Follow the Tim Ferriss Podcast: https://tim.blog/podcast/ Visit the Tim Ferriss Blog: https://tim.blog/ Follow Tim Ferriss on Twitter: https://twitter.com/tferriss/ Follow Tim Ferriss on Instagram: https://www.instagram.com/timferriss/ Like Tim Ferriss on Facebook: https://www.facebook.com/TimFerriss/ [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.