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

What It Covers

Rich Barton shares how he built Expedia and Zillow from zero to $35 billion combined valuation, detailing his provocation marketing strategy, naming methodology using high-value Scrabble letters, internal Microsoft venture funding approach, and daily rituals including morning routines and fitness habits.

Key Questions Answered

• •Intrapreneurship Strategy: Barton pitched Expedia as an HR experiment to retain entrepreneurial talent at Microsoft, spinning out 150 employees who would have left otherwise. He secured $100 million in advertising budget by arguing public markets would fund it essentially free during the 1999 bubble, demonstrating how to leverage market conditions for internal ventures.
• •Provocation Marketing Framework: Build features around emotionally charged topics (seven deadly sins zone) that address taboos or sacred cows, but ensure they make people feel good rather than scared. Examples include Zillow's home value estimates, Glassdoor's salary transparency, and Avvo's attorney ratings—all designed to generate organic conversation and media coverage without traditional advertising spend.
• •Company Naming System: Use high-point Scrabble letters (Z, X, Q worth 10 points) for distinctiveness, limit to two syllables maximum, ensure it works as a dog name and verb, include double letters or palindromes. This creates memorable, ownable brand equity versus generic descriptive names like hotels.com which lack defensible positioning.
• •Strategic Defense Against Google: Avoid dependency on Google traffic by building direct brand recognition and embedding into industry workflow. Create tools that become integral to transactions rather than just lead generation middlemen. This prevents disintermediation when platforms like Google move vertically into your business model, as happened with travel and review sites.
• •Failure Recovery Culture: After Barton's $10-20 million MS-DOS book bundle failure at Microsoft, his boss Brad Chase asked what his next big idea was instead of punishing him. This approach—protecting innovators from corporate immune system rejection while maintaining accountability—became Barton's hiring and retention philosophy for identifying intrapreneurs who drive company growth.