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

This episode explores the entrepreneurial journey and philosophies of Rich Barton, co-founder of Zillow and Expedia. Against the backdrop of his early career at Microsoft, Barton recounts his first major project, a bundled software-book package that failed, highlighting the importance of taking calculated risks and fostering a culture that embraces innovation, even in failure. More significantly, the conversation delves into the creation of Expedia, detailing the strategic decision to spin it off from Microsoft as both a financial and human resources maneuver to unlock value and retain talent. For instance, Barton describes the challenges of pitching the idea to various stakeholders, from employees and their spouses to Bill Gates himself. As the discussion pivoted to Zillow, Barton shares the initial struggles and pivots before achieving success, emphasizing the importance of identifying large market opportunities and employing "provocation marketing" to generate buzz and overcome industry resistance. Ultimately, the episode underscores Barton's approach to building successful companies, emphasizing the selection of talented individuals, the cultivation of a collaborative environment, and the strategic importance of understanding and adapting to market dynamics. This means for aspiring entrepreneurs a focus on identifying large problems, building strong teams, and embracing calculated risks, even if it means facing regulatory challenges.