In 2006, Spencer Rascoff co-founded the real estate company Zillow, known for their "Zestimate" for figuring out the value of a home. Before that, he co-founded Hotwire that was later acquired by Expedia. He shared with us his management style which includes leading authentically and with transparency and the fact that if he wasn't running Zillow, he'd be a cowboy spending his days outside.