After Hotwire recovered, the company was acquired by IAC/InterActiveCorp, the parent company of Expedia at the time, for $665 million in cash plus $20 million in options and warrants in 2003.
"Every start-up, every company has challenges. The most important thing is to try to build a team that you work well with, one that can rally behind the same mission together," the 40-year-old CEO said.
Rascoff went on to join real-estate website Zillow in 2005 and served as chief operations officer, chief financial officer and vice president of marketing before getting tapped as CEO in 2010. Rascoff helped lead the company to its initial public offering in which the company opened at $60 a share, up 200 percent from its $20 pricing.
In the fourth quarter of 2015, Zillow Group brands saw approximately 124 million average monthly unique users, up 61 percent from the same period last year. The company has a $3 billion market cap.