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The Tim Ferriss Show #806 · April 15, 2025 · 2h 25m

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

Rich Barton — co-founder of Zillow ($35B), Expedia, and Glassdoor. How he built three major companies by making information free that used to be locked behind gatekeepers. Morning rituals, leadership through absence, and firing people as a win/win.

Highlights

Power of information transparency
All three companies (Expedia, Zillow, Glassdoor) share one thesis: free the information that gatekeepers hoard.
Scrabble tiles for company naming
Barton used Scrabble tiles to brainstorm company names. Zillow came from 'zillions' + 'pillow.'
Leadership through absence — the two-week disconnected trip
Barton takes two weeks fully offline every year. The organization must function without him.
Firing as a win/win skill
Learning to fire people well is a critical leadership skill most people avoid.

Misc

Brad Chase at Microsoft taught Barton to 'swing big'
Board membership criteria: 'Is it local? Is it fun? Is it lucrative?'
Has a family tattoo — design and symbolism discussed
Eddy Cue (Apple) referenced at the top