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Spencer Rascoff

๐Ÿ‘ค Speaker
577 total appearances

Appearances Over Time

Podcast Appearances

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

So it seemed like a good time to retire from that role. So that's why I stepped down in 2019. And it was a seamless transition because my co-founder, who had been chairman all that time, just stepped in as CEO. So easy squeezy.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

You know, I stayed on the board for about a year and then started starting new companies at that point. And once I started starting new companies, it didn't really make sense for me to stay on the board of Zillow. The pandemic, I was gone from Zillow by the time that was in full swing. So I can't really speak to how Zillow managed through it.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

You know, I stayed on the board for about a year and then started starting new companies at that point. And once I started starting new companies, it didn't really make sense for me to stay on the board of Zillow. The pandemic, I was gone from Zillow by the time that was in full swing. So I can't really speak to how Zillow managed through it.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

You've heard now 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. So we started Picasso right before the pandemic. And Picasso is co-ownership of luxury vacation homes, like a NetJets for vacation homes.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

You've heard now 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. So we started Picasso right before the pandemic. And Picasso is co-ownership of luxury vacation homes, like a NetJets for vacation homes.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

And the idea for Picasso is that people co-own the home with other families that they don't necessarily know. So when the pandemic happened, I said, oh my God, it's happening again for a third time because are people really going to be willing? I mean, just remember how people were afraid of germs back then. We weren't even accepting packages.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

And the idea for Picasso is that people co-own the home with other families that they don't necessarily know. So when the pandemic happened, I said, oh my God, it's happening again for a third time because are people really going to be willing? I mean, just remember how people were afraid of germs back then. We weren't even accepting packages.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

You'd leave your groceries at your front door or at the garage for six hours or your Amazon packages. in order to let the cooties wash away. So are people really gonna own a house together with strangers? Like, oh my God, you know, people are never gonna accept that health risk. So I was pretty worried about the impact, very worried that it would have on Picasso.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

You'd leave your groceries at your front door or at the garage for six hours or your Amazon packages. in order to let the cooties wash away. So are people really gonna own a house together with strangers? Like, oh my God, you know, people are never gonna accept that health risk. So I was pretty worried about the impact, very worried that it would have on Picasso.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

It turned out that the pandemic and the quarantine was very good for Picasso. Again, silver lining, just like Hotwire had, just like Zillow had. The silver lining was demand for second homes went through the roof when people started working from home and people wanted a place to get away from their primary residence. So Picasso had a rocket ship start.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

It turned out that the pandemic and the quarantine was very good for Picasso. Again, silver lining, just like Hotwire had, just like Zillow had. The silver lining was demand for second homes went through the roof when people started working from home and people wanted a place to get away from their primary residence. So Picasso had a rocket ship start.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

It was the fastest company to become a unicorn. We raised over $200 million of venture capital. We sold tons and tons of these vacation homes. And then the next crisis that we faced was mortgage rates that skyrocketed. So within a six-month period, mortgage rates went from about 2% up to 10%. Nobody's ever seen that type of increase in mortgage rates.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

It was the fastest company to become a unicorn. We raised over $200 million of venture capital. We sold tons and tons of these vacation homes. And then the next crisis that we faced was mortgage rates that skyrocketed. So within a six-month period, mortgage rates went from about 2% up to 10%. Nobody's ever seen that type of increase in mortgage rates.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

And that had a huge chilling effect on interest in second homes. And so here we are again, I kind of made it through the quarantine issue, but facing yet another crisis in my company's history. And Picasso had to manage through that. We closed some markets. We downsized the company. We refocused. We tightened the belt. We did all the things that we did at Hotwire and Zillow.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

And that had a huge chilling effect on interest in second homes. And so here we are again, I kind of made it through the quarantine issue, but facing yet another crisis in my company's history. And Picasso had to manage through that. We closed some markets. We downsized the company. We refocused. We tightened the belt. We did all the things that we did at Hotwire and Zillow.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

And now here we are as we record this in late 2024. Picasso is on the upswing. And we've sold about a billion dollars of these vacation homes. We've got thousands of very happy owners. We're in over 40 markets in four countries. And Picasso is by no means out of the woods entirely, but feels a lot better today than it did a couple years ago.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

And now here we are as we record this in late 2024. Picasso is on the upswing. And we've sold about a billion dollars of these vacation homes. We've got thousands of very happy owners. We're in over 40 markets in four countries. And Picasso is by no means out of the woods entirely, but feels a lot better today than it did a couple years ago.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

That's right. So Picasso is doing something pretty cutting edge right now. We're doing what's called a Reg A offering or a Regulation A offering, which is a round that retail investors, individual people, are able to invest in. And the reason we're doing this is it's very consistent with our mission.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

That's right. So Picasso is doing something pretty cutting edge right now. We're doing what's called a Reg A offering or a Regulation A offering, which is a round that retail investors, individual people, are able to invest in. And the reason we're doing this is it's very consistent with our mission.

Leap Academy with Ilana Golan
Former Zillow CEO, Spencer Rascoff: Leading Billion-Dollar Startups Through Crises | E63

What Picasso tries to do is democratize access to second homes, to something that is typically only available to very wealthy people. And Private venture-funded companies are also typically not available to retail investors. They typically have to wait until these companies go public.