Ilana

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.

He also co-founded Hotwire, which was sold to Expedia for $685 million.

You did allude a little bit to the 2008 crisis. How did you maneuver that?

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?

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?

So you were an overachiever from a very early age. You showed it in school, student body, president, all of that. Am I right? You were always kind of pushing yourself.

So when you went to college, did you already have in mind that it's going to be entrepreneurship? Because you went to investment banking and that route. Was it by definition? Did you just roll into it? How was it, Spencer?

So you left a very lucrative, well-paying roles, right? In Goldman Sachs and the private equity, very safe in order to parachute into starting Hotwire. So how did that happen? Why did that happen?

Every startup is, but I want to take you through that moment because I think people, they probably can't really understand what you went through, but they can start relating to it because that feels like a disaster. When you run a company and you know that you have some piece in this disaster, how do you wake up? How do you take care of yourself, Spencer?

Because I think that scares a lot of people and that's really hard too.

I think you're right because, Spencer, one of the things that we see all the time is that when people are going through these near-death experiences, they quit. You didn't quit on Hotwire. You continued. But I think there's some areas where you're like, I'm suffocating. So how do you go through this?

That makes sense. I don't know if that makes it a lot less scary, but maybe a little less lonely.

So you recover from 9-11, you sell it to Expedia and you spend some time in Expedia. Why then start Zillow? How did that form? And I think there's also some people that also left Zillow. Can you share a little bit of that story?

Did you realize that what you're creating will go so viral or was it an experiment and feels more like you created your own luck to some extent?

I definitely want to go there. I want to go into two things that I think are fascinating for our listeners, because first of all, there's this notion, at least in the Silicon Valley world, get out as fast as you can, get out scrappy, et cetera. But when you get out very scrappy, there needs to be a little bit more baking in order to get to the millions that you've seen.

So first of all, how do you balance between the MVP or the minimal viable product versus going with something that is good enough for it to really go viral?

Got it. So now you are literally jumping on the wagon of mobile, which I think is something really, really interesting, because as we know, some companies completely missed the boat. First of all, how did you realize that you need to be mobile first? And you changed everything. You changed Zillow completely to be mobile.

So if I'm hearing you correctly, it sounds like you're basically relentless on understanding your audience avatar. You understand that they're not going to be on desktop. They will be roaming around. They will be driving. And you're relentless on trying to understand what do they need when they are driving around. They are looking for homes. And together with being very attentive to what's coming.

So it sounds like it's that... constantly being relentless about what is really needed versus what I'm building.