How to Build the Next Huge Thing

Spencer Rascoff cofounded Hotwire and Zillow. Now he's an investor and serial startup founder. Here's his advice for funding and growing a giant, ambitious idea.

- NICOLE LAPIN

Want to start, fund, and sell a major company? Spencer Rascoff has some advice on that because he's seen it from all sides. 

As a founder, he first cofounded the travel-booking site Hotwire, which he sold to Expedia. He then co-founded Zillow, which helped reshape nothing smaller than the real-estate market, and served as its CEO for nearly a decade. Now he's a serial board member, an investor (including as general partner at the venture fund 75 & Sunny), and a continual startup founder-including building social platforms for sharing intel on food (Recon Food, which he started with his teenage daughter) or what's best to binge-watch (Queue), saving creatives from the endless emails they face as they chase down business leads (heyLibby.ai), and simplifying the market for co-owning a second home (Pacaso).

"I find problems that I have in my life and feel passionate about, and I try to solve them by starting companies," he says. But actually funding, growing, and selling those companies? That's about great ideas-and also cold, hard numbers. Here, he explains.

You've said that Zillow didn't start with the ideait started with the team. Can you tell that story?