Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63
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Startups are hard. Hang in there, everybody.
Spencer Vascoff, co-founder and CEO of Zillow until 2019, which during your time grew to over 4,500 employees, $3 billion in revenue, $10 billion in market capitalization.
As a kid, I watched a lot of entrepreneurship and that was inspiring to me and helped encourage me and my path to entrepreneurship.
He also co-founded Hotwire, which was sold to Expedia for $685 million.
Two of my companies, Hotwire, which had a crisis two years in, and then Zillow that had a crisis two years in with the financial crisis. My next company, Picasso, also had this crisis, which was the pandemic. Founders of startups who are listening to this, if you want a simple, safe, stable job, go do something else. That is not what startups are. Being provocative helps drive virality, and that's certainly one of the ways that Zillow grew.
You did allude a little bit to the 2008 crisis. How did you maneuver that?
I would say...
So today I have a really great episode for you because this person, I've been following him for a long time, Spencer Vascoff, co-founder and we're CEO of Zillow until 2019, which during your time grew to what, over 4,500 employees, 3 billion in revenue, 10 billion in market capitalization, massive. And I think every single person knows Zillow, which is incredible. My daughter uses Zillow for fun. You also co-founded Hotwire, which was sold to Expedia for $685 million in 2003. You've been on boards of TripAdvisor and Palantir and co-founded many ventures recently we'll talk about. But you come from a family of entrepreneurs. So take us back in time to Spencer, like the kid. How did you grow up and how did that shape you?
I was always interested in entrepreneurship and business. I was the kid that would bake cookies and sell them on my street, that would get tracing paper and trace artwork because I wasn't a good artist, but I could trace things and sell those tracings to my parents' friends. So I was always hustling and trying to create businesses and make money. And I saw a lot of entrepreneurship all around me. My grandfather was a really successful entrepreneur in the apparel space. He had started a clothing company. My dad was a very successful entrepreneur. He started out as an accountant, and then he became, through a lot of hard work and also some good luck, ended up starting a business management company and tour production company that...
had clients like the Rolling Stones and U2, David Bowie, Paul Simon, Pink Floyd, Leonard Skinner, and many, many others. And so I watched him pivot his career many times as the technologies of the music industry changed. So when platforms shifted from eight tracks to, I guess, records to eight tracks to tapes to CDs to streaming that had profound implications on how his business had to evolve. As the concert industry changed, he moved more into touring and helped pioneer many aspects of the touring industry that we take for granted today, like the 360 tours where producers and promoters buy tours outright from the acts and flip the story on who works for whom and sell broad sponsorships for these international tours, et cetera.
So as a kid, I watched a lot of entrepreneurship and that was inspiring to me and helped encourage me and my path to entrepreneurship.
When you look at your dad like that, and he's probably worked really, really hard, did that create that hunger from early age or did that scare you? Like, I don't want to work that hard as crazy as my dad. Like, what did that do as a kid?
I've always worked hard. I worked hard when I was a kid. One of my most formative experiences early on was playing chess. And I was basically, well, not quite a professional chess player, but I was a very competitive, serious chess player as a kid, I think, at college. Age 12, I was the fourth best chess player in the country. I was the captain of our chess team that won middle school championships and we're basically the best middle school chess team in the country. Basically, every weekend I was playing chess tournaments around the country. And... You learn a lot from chess as a kid.
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