Zillow Former CEO & Co-Founder: Spencer Rascoff


Today's guest is Spencer Rascoff. If you're reading this you probably know who Spencer is, but in case you don't, he most known for co-founding Zillow Group and was the CEO for a long time before stepping down in 2019 to focus on his new ventures dot.LA and Pacaso. In his first startup experience, Spencer co-founded an online travel company called Hotwire which later sold to Expedia in 2003. After working at Expedia for some time he felt the need for a change and started Zillow with other ex-Expedia employees. He is the co-author of "Zillow Talk: Rewriting the rules of real estate" and the host of two podcasts "Office Hours" and "Dad I have a question." In this conversation we take you through Spencer's entire career journey including the highs and lows, and learning lessons along the way.

Podcast Transcript

Note:  There may be errors to this transcript (some funny, some confusing - we used an automated transcription software!)

Ash Faraj  00:02

Hey, it's ash here. Now before we get into the show, I had just a quick announcement to make. I recently released my ebook called the five uncovered steps to kick starting your dream career. And it is now available on Amazon Kindle or on our website for purchase. It's based on all the conversations we've had with all the amazing guests on our show. We've had fortune 500 executives, popular startup founders, and well known investors from the VC community. Now the book cost $20 but if you cannot afford it, please please send me an email at ash at exactly talks.com and I am happy to provide you one for free. Today's guest is Spencer rascoff. If you're listening to this right now, you probably know who Spencer is, but just in case you don't. He is most known for co founding Zillow group and was a CEO for a long time before stepping down in 2019 to focus on his new ventures.la and Picasa, which you want to stick around to the end by the way to hear about what those ventures are all about and what prompted the pursuit of those ventures and you are in for a special one today, my friend so settle back on wine and enjoy this conversation. He is the co founder of hotwire which later sold to Expedia in 2003, the co founder and former CEO of Zillow group, the co author of Zillow talk rewriting rules in real estate, the host of two podcasts, office hours and then have a question most recently, the co founder of Daniele Picasso, I met a rental stuff there, how we have one breath, Spencer, welcome to the show.

Spencer Rascoff  01:36

Thank you very excited to be here. Thanks for having me.

Ash Faraj  01:38

To start off. I'm in a high school classroom with you. I'm your friend, who is Spencer,

Spencer Rascoff  01:43

I was pretty academic, in high school, but I guess also relatively social and outgoing newspaper took a lot of my time in high school. So I was editor in chief, the high school paper, I thought I want to be a journalist, I spent a lot of time in the newsroom. And it was a very formative experience for me. And I always tell this to my kids, and I encourage them to do activities in school that provide some exposure to management of your peers. Because the cool thing about newspaper and a couple other activities in high school is it's the rare activity where you're actually in a supervisory role, managing your peers, like on a sports field, you're you're all equals, in a newsroom in high school, or college, you know, you're staffing a peer on a story, you're editing their work, and figuring out how to get the most out of somebody else. And their work, when really you're inherently peers. That's an important management lesson, something that I learned at a young age and that kind of player coach philosophy of management that started in the newsroom in high school continues to this day and how I run my companies

Ash Faraj  02:54

and you play chess to in high school or was that

Spencer Rascoff  02:57

I played chess when I was younger, I played chess from age five to 13 or so. So I was a competitive chess player. I think when I was 12, I was one of the top chess players in the country and played tournaments every weekend and was the captain of my middle school chess team, which went on to win the national championship. So chess was a very important activity for me as a little kid. And it taught me concentration. It taught me competitive drive, it taught me how to plan ahead, the importance of hard work. It was it was great activity, something that I encourage my kids to do as well.

Ash Faraj  03:32

Yeah, I think this is kind of random. But I read somewhere. I don't know exactly what it was. But when you were younger, like your secret ambition was to become a cowboy. Is that is that?

Spencer Rascoff  03:42

Yeah, you know? Yes. So I've said publicly somewhere that I want to be a cowboy when I grew up. And that's still sort of true. But I mean, I think what it means really more generally, is I just like being outdoors. One of the big negatives of a professional sort of white collar career is that typically you're doing it indoors. I always wanted a job that I could do outdoors. And you know, I'm still looking for one.

Ash Faraj  04:06

You know, I hate to bring this up. And sometimes in life, things happen to us. We have bad memories. But I do think the reason I bring it up is because I feel like it played a critical role and how it shaped you that your brother passed away when you're 15

Spencer Rascoff  04:17

Yeah, for sure. And it certainly definitely shaped my my life in many ways. When I was 15. And my brother was seven teen. He died in a car accident the day before graduating from his high school from our high school. And he was the editor of the high school paper as well a couple years before me. And he had stayed up all night in the newsroom putting together the last issue. And that morning, he drove to take it to the printer that was back when you had to actually physically take the paper to the printer for them to print it. And he was in a car accident that morning on the way back from the printer. So, you know when people have these kinds of tragedies it obviously it goes on to him Back to your entire life. I think for me, the main impact for me, I guess professionally was that it caused me to sort of double down and refocus on kicking ass as much as possible. And trying to just accomplish, accomplish, accomplish, because he wouldn't be there to accomplish things. He was very accomplished in a very short period of time. But, you know, who knows what he would have gone on to accomplish? Had he lived. And I'm, in many ways, trying to rectify that

Ash Faraj  05:39

can only imagine how it feels. I know that your father, obviously he instilled that entrepreneurial DNA in you. And he left his corporate job to be a manager for the Rolling Stones, how, what was your, what's your favorite memory with your father,

Spencer Rascoff  05:52

my dad had a really interesting career, as you mentioned, he was an accountant early in his career, and then he left accounting to move into the music business. And he became the business manager and top producer for the Rolling Stones and YouTube and David Bowie and the police, and Paul Simon and Pink Floyd and many, many others. And so it was a very interesting career, and certainly a fun way to grow up going to a lot of concerts. You know, I one, one memory I have of him in that setting was being on the mixing platform, at a Rolling Stones concert, and kind of watching the concert through his eyes. And I was I was a teenager in high school, and, you know, having him walk me through the business aspects, like shouting in my ear, because it was in the middle of a Rolling Stones concert. You know, the revenue for this show is x, you know, he sold 100,000 tickets at these price tiers, you know, the merger is going to be this and the, you know, we got to finish by 11pm. Or else the union goes into time and a half on the breaking down the sets. And, you know, they're 38 trucks backstage that, you know, that are all teamster trucks. And that means that they're going to cost 20% more than blah, blah, blah, you know, like, yeah, this is not, you know, I don't think he was really listening to the music. He was, he was seeing it through a business lens. And it was, you know, it was a fun memory for me, because in a lot of ways, that's how, you know, that's how I experienced rock concerts to some extent as well. It's not very romantic. But, but it is a different perspective.

Ash Faraj  07:33

So after college, you know, you go work on Wall Street, how do you remember that

Spencer Rascoff  07:38

worked out straight at a young age is a very formative experience. I tweeted the other day that I just finished watching the first season of industry on HBO Max, which is about being an investment banking analyst at a fictional investment bank. And, you know, it's a great show, I highly recommended, I tweeted something like, you know, my experience as a financial analyst at an investment bank had a lot more Excel and PowerPoint and a lot less cocaine and sex than, than in that TV show. But um, but the, what the show got right was the intensity, the cutthroat nature of the environment, the adrenalin, of working hard when you're in deal mode, trying to get a deal done. And all of that is a terrific way to start one's career. The other great thing about investment banking, or consulting straight out of college, is that you end up with a lot of responsibility at a very young age. It's one of the only careers where in your early 20s, you can find yourself in the boardroom of a fortune 500 company, discussing and debating a company changing decision, like buying another company or selling off a division are moving into a new business line. You know, these are things that investment banks and consulting firms advise on and as a 21 2023 year old, you know, you're not going to be leading that discussion. But just to be in the room, where boards and management teams are having those discussions is incredibly instructive and illuminating and fascinating and career developing. And that's one of the biggest benefits of starting one's career in investment banking or consulting.

Ash Faraj  09:23

Yeah, so then obviously, you decided to leave and join Texas Pacific group, how do you remember, you know, from what you remember, why did you leave and then in general, if you can generalize it when you do make a career change, or when you do make a career pivot? What generally what generally sparks that

Spencer Rascoff  09:35

the decision to leave Goldman Sachs was prompted by the fact that it was the end of a two year analyst program. A lot of my colleagues left early from that two year commitment that you make when you join straight out of college. It's a little bit different today. But back then it was really a two year a two year gig. I decided to leave investment banking because I although I liked the intellectual stimulation of it, I liked a lot of things that We already discussed, I want it to be a little bit closer to the operations of the business. investment banking is sort of at a 10,000 foot level or sometimes 30,000 foot level, it's providing high level strategic advice to a company around an acquisition, for example, or financial transaction. But I wanted to be closer to the the actual product closer to the company closer to the customers. And so I moved into a private equity role at this firm TPG Capital, which is one of the top private equity firms in the country. And that's closer to the operations of business of a business, because companies like TPG, actually own these companies. So you are a principle, you know, you're not just providing advice, you were actually an owner of the company. And so that was my next career step. And, you know, that was better, but it still wasn't quite close enough. At the end of the day, it was still wasn't quite close enough to the operations of the company. At the end of the day, you were still working at a financial institution that owned other companies. And so I wanted to be closer to where I thought the action was, which was the actual company. So I worked to start one. And you know, my first startup hotwire, we started within TPG. And we built that into a, you know, pretty big company. And we sold it four years later to Expedia for about 700 million.

Ash Faraj  11:21

Yeah, I, you know, one question I had about hotwire, you know, were there any, like, hiring mistakes early on, because your first startup, obviously, you need sometimes when you, when you when you first do something, you tend that's when you tend to make the most mistakes? Were there? Did you make any hiring mistakes early on? Or no?

Spencer Rascoff  11:39

Oh, many? You know, you always do, I think, you know that, that the key challenge at a high growth company with respect to people management, is figuring out if you have the right people in the right roles as the company's needs change. So if you think about hotwire, for example, right? My co founder and I start this company, we have two other co founders joints, they're four co founders. And then you hire three people, five people, 10 people, or 10 employees, 1520 employees. And, you know, you'll hire someone for a particular role. And within three or six months, that role has changed quite a bit. This happens a lot in engineering, for example, maybe you hire somebody, because they're a great software engineer. And they're just a terrific coder. And then all of a sudden, in the blink of an eye, six months later, they've got a 10 person team that they're managing. And maybe they're not a great manager, or maybe they don't want to manage but all of a sudden, they've been sort of put into that position.

Ash Faraj  12:37

Obviously, during your time at hotwire, you know, there was there was a tragedy in a family friend that went down and one of the planes that went down to Pennsylvania.  Yeah.  Gives me just goosebumps thinking about I mean, obviously, was a tragedy for all of us. But just to think that somebody was personally connected to me that was on there. It gives me goosebumps, but how were you? Like, can you take us through some of your emotions that you were feeling?

Spencer Rascoff  12:57

Yeah, I mean, so. So we started our next 99. And in 2001, the company was doing very well. And then September 11 2001 happened. And as you mentioned, a good friend of my parents and of mine was killed in one of the planes. I also was affected by it. I mean, fortunately, obviously, I'm still here. But I was on the plane on September 10, from Newark to SFO. So one of the four planes same tail number, same, you know, same flight number, etc. And I given a speech on September 9 at the Millennium Hilton in New York, which collapsed under one of the one of the World Trade Center buildings. So, I mean, I was 24 hours, saved by a 911, having been there and flown on that same plane. And then it turned out that hotword sold a couple of the tickets to the hijackers, not the September 11th flights, but the September 10 flights that put a team in position from Bangor, Maine to Boston, Logan. And I only started talking about that publicly. A couple years ago, I figured 20 years had passed, it was okay to start. start sharing that it wasn't something that we even told our employees at the time, it was a very closely guarded secret at the at the top top levels of the company. So we have this really weird sense of of guilt and association with the tragedy of 911. And then we had a business crisis on our hands, right? We had 10s of 1000s of stranded customers. We had companies are our main partners were the airlines, and they were the main owners of the company, and they were all struggling and teetering on bankruptcy. And then people were afraid to fly and were afraid to travel. And so for six or 12 months, there was a very, very deep travel recession, very similar to what we're experiencing now with COVID actually, and not a great time to be an online travel company. Just like she was like 2020 was not a great time to be an online travel company. But we at hotwire we we hung in there. We did lay off so went from about 200 employees to I think about 150. We did a down round, which capitalize the company to survive, but also wiped out a lot of the equity in the company. And we, you know, we locked arms. And as a team, we hung together and reprioritized and refocused and managed to turn the company around such that by two years after 911, we were on an IPO path and sold the company successfully two years after 911.

Ash Faraj  15:28

Yeah, so 2003 like you mentioned, Expedia acquires hotwire and the know, you know, you go work for, for dhara, who's now Uber CEO was, yeah, wasn't he? He was a mentor of yours early in your career was that as?

Spencer Rascoff  15:39

Well research to credit here? Yes, so dark Houser, Shah, he was my manager at Allen and Company, which is an investment bank when I was a summer analyst, still in college. And he was, I think, just just out of college himself. So So did you enjoy Expedia. I mean, I enjoyed aspects of it. This is you know, just to just to frame the era here, this is 2003 to 2006. It's the people at Expedia were incredibly high quality. But the company was struggling to remain innovative at the time, the company had become the clear category leader in online travel at the time. Since then, Priceline and booking.com have arguably passed it certainly cost it in terms of market cap, but arguably passed it in other ways as Airbnb. But at the time Expedia was the king of the hill. But it company was, as I say, struggling to struggling to be to maintain its level of innovation. And so I found that somewhat frustrating and ultimately decided to leave to try to do another startup, where I felt that I could have more of an impact. And I felt that the company could be more innovative.

Ash Faraj  16:49

Yeah. And I guess from what I read, it was actually some of your employees, you some of the employees, Zillow, like you guys just kind of got together and decided that you wanted to do this startup and what what's what was going through my head when I was reading that was, how does that conversation even begin? Like? I just say, Hey, we're all gonna leave and start the startup like, What? How does it How did it even start?

Spencer Rascoff  17:08

Yeah, so here's how it began. I came home from work yet again, and complained to my wife about how I was frustrated at work. And she said, Well, then why don't you quit? Stop complaining. And I said, Well, these two other folks who were colleagues of mine had also recently quit kind of frustrated. And she's like, great, why don't you call them and do something. And so I called them and said, hey, let's start a company. And, and then we spent a couple months brainstorming different business ideas, and working through different concepts and Zillow was born.

Ash Faraj  17:46

So early days of Zillow, right? How did you make How did you guys make hiring decisions? So like, if you had 10 applicants for a job? Like what what stood out to certain applicants for you? I'm just kind of curious to get into your mind of like how you decide to hire somebody or not hire somebody like what, what, what stands out to you in a candidate,

Spencer Rascoff  18:05

I've always prioritize what we used to call culture fit. Which nowadays we've kind of rebranded core values fit. And I think that's a good rebrand because culture fit can be code for hiring people just like me. You know, sometimes you say, oh, that person is not a culture fit that sort of code for they didn't go to your college or they don't, you know, they don't look like you are dressed like you. So thinking about whether an employee or candidate is a fit for the core values of the company, rather than the culture of the company, is how I always prioritize my hiring decisions at Zillow and at all my companies. So what does that mean? It means that some of the core values of Zillow were turn on the lights, which meant be transparent. zg is a team sport, which means we're very team oriented on it, which means exhibit a high degree of ownership and sense of responsibility at my companies now, like Picasso, which has similar core values or.la, we look for people that live the core values of the company that is more important than subject matter expertise. So yes, that's right. Let me repeat that core value fit is more important than subject matter expertise. People can learn how to be a great email marketer, people can learn how to be a great you know, PR person, people can learn how to be a great you know, you name it, salesperson, but if but but you can't really learn the core values through there are transparent, team oriented, have a high sense of integrity and responsibility or you're not you've learned that in kindergarten and in grade school, and high school newspaper and playing chess and all the other activities that you did as a kid, and you know, starting in kindergarten and earlier and so that's what we prioritize that's,


that's powerful. So you're in an interview with somebody or like you're deciding whether to hire somebody or not, you know, obviously there's gonna be risk when you hire somebody, but how do you Like how do you know if they are a core value? I mean, you can't really just but

Spencer Rascoff  20:04

it's hard. No, you're right. It's hard. I mean, at Zillow We, on the interview loop, we staffed each a different person. So if say, we have five people interviewing the same candidate, each of the people would be staffed on sussing out a particular core value. So maybe, you know, if I were the only person, then I would have to discuss with the candidate all sorts of general stuff about, you know, your background and your experience level, etc. But in particular, I was responsible, trying to figure out whether that person exhibited that core value. And you're right, it's hard, but it's a discussion of, you know, tell me times in your past, where you've shown a lot of sense of ownership over a product or, you know, or a challenge and, you know, or etc. So, it's, it's, it's difficult, sometimes it can't be fully assessed or properly assessed until the person is already already at the company, but you do your best.


So last, last bad memory for office 2008 happens. Take us through the worst day of that of that. Sure. recession.

Spencer Rascoff  21:09

Sure. I mean, and and these are bad memories, but they're also formative. And this is what, you know, what, what makes people and it wouldn't, it's what makes companies or breaks companies. So starting in 2007, it was pretty clear at Zillow, we could see in the data that housing was a house of cards that the of the bubble was going to burst. I wrote a blog post on Zillow blog, which I should google it and see if it's, it must still be up there somewhere called the tidal wave is coming. And I think I wrote that in summer 2007, when everything was, you know, still looked fine. But we were looking at foreclosure data and, you know, data around how many people were more than two or three months behind on their mortgage payments. And it was pretty clear that we were going to hit this foreclosure wall in late 2007, early 2008. And so so we started ringing that alarm bell, I wish I had, you know, shorted MBs is or the homebuilders or, you know, somehow bet behind my, you know, my instinct, all I did was write a couple blog posts about it, which didn't, those don't pay off quite the same way as putting out a short on housing. But anyway, um, so in 2008 happened and the financial crisis happened and Lehman and AIG and everything else, you know, I certainly wasn't surprised as I say, we we called it. Stan Humphries, who wrote Zillow talk with me with our chief economist, you know, he and I had been out in front in the media predicting this, the impact that it had on Zillow was significant, significantly negative initially. And, you know, negative initially because we, you know, we were a real estate media company that made money by selling advertising to those in the real estate industry. So from a revenue standpoint, it was it was negative. From a strategy standpoint and a business standpoint, it was incredibly positive. Because we were able to go to the real estate brokerage community and the multiple listing service community and say, Hey, houses are not selling right now. So give us your listings. Put your listings on Zillow for free, we will not charge you. You're welcome. Put your listings on Zillow, we'll get them exposure on to one of the top real estate sites in the country. And, you know, you need that exposure for your listings because these houses are selling. And so the recession, the 2008 financial crisis accelerated Zillow is attempts to get listings from the real estate community. It also had another big advantage, which is volatility benefits information providers. So for the same reason that CNBC ratings go up when the stock markets are wild, up or down. Zillow has ratings as Angelus traffic goes up when the housing market is volatile, up or down. So all of a sudden, every day in the news, the media saying you know housing is crashing, housing is crashing. So what do people do? They turn to Zillow to see what's happening to their house. So it drove a lot of traffic and brand awareness and it drove a lot of listings content, but it hurt revenue in the short term. So in a lot of ways, it was similar to the impact that 2001 had on hotwire because hotwire benefited in a perverse way from the travel recession. Because the travel companies the hotels and airlines needed online distribution more than ever, after 911 and so they turned to Expedia and hotwire for distribution of their product. And likewise in 2008 the real estate industry homebuilders, apartment building owners and real estate brokers turned to companies like Zillow for distribution of their product. So it was turned out to be a net positive once we made it through and Fortunately, we avoided a down round. We did have layoffs though, at Zillow in 2008. We went from about, I think, 200 ish people to about 150 people kind of similar size to the hotwire reductions of 2001. But, but ultimately, it probably benefited the company.

Ash Faraj  25:18

It also seems like you know, you talk about how you know Zillow, you know, your first job ever wasn't that you were in media like you were it wasn't Fox or something. It was like your first job ever. And you you said it's actually not that much different from Zillow because Zillow is a real estate media company. And just seems like that experience was also even though it was just like it was your first job. And even you know, people wouldn't think much of it. It was actually played a huge role and kind of like,

Spencer Rascoff  25:41

Yeah, for sure. For sure. So I mean, as a, as I mentioned, I was always interested in journalism. And, you know, before I even did investment banking, when I was in high school and college, I did summers at Bloomberg, as a reporter, summers, NBC News as a junior producer, and a summer at Fox, Fox Broadcasting, not Fox News, Fox Broadcasting, which was like the Fox Television Network, in the research department, analyzing TV ratings and making programming recommendations. So I was always interested in media. And yeah, I mean, Zillow is a media company, less so today than it was in 2008. Because started a couple years ago, I put the company I put Zillow on, of course, to become a real estate transactional business where Zillow now buys and sells houses itself. Rather than just being a media site where consumers can get information. Zillow is now a digital marketplace for homes. So it's still a media business on one half of the business but the other half is really ecommerce now

Ash Faraj  26:40

2019 you stepped down from Zillow. In in your annual review, you mentioned that the reason that you had stepped down from Zillow was because you felt like you needed to change like you wanted a new learning opportunity, you wanted to enter a different space. Is that is that more of like a process, there's more of a feeling like how did you know was the right time to do that?

Spencer Rascoff  26:59

You know, it, it's just kind of, you know, like, when work starts to feel like work, then it's probably time to do something different.

Ash Faraj  27:09

That was succinct.

Spencer Rascoff  27:12

You know, I, I accomplished what I want to accomplish. Zola built a big company had, you know, expanded it into a lot of different directions had built a incredible and sustaining culture. And, you know, that was felt like it was the right time. And, you know, so I have lots of other ideas, and I still have lots of other chapters left to right.


So our audience is made up of 2425 year old new professionals, and when I talk to them, when I communicate with them, they say a lot of them say that they would rather take a job that pays more, but maybe it's like in a city that they don't want to be in or so that they're me.

Spencer Rascoff  27:51

No, no, no terrible. This


is exactly what I want to say what I wanted to ask you was, you know, obviously, when you stepped down from Zillow, it's like, you know, you have the luxury to retire. But you go on and start, you know, you go on and start Donnellan. Why did you start nataline Picasso? Why did you do that?

Spencer Rascoff  28:08

Sure. Okay, well, so So two things there. One, I can I address the please? career decision? Question. Okay. So the compensation differences at that junior level are going to be rounding errors in rip for most people in relatively short order. So if it's 70k, or 60k, or 80k. I know, this sounds a little obnoxious, but like, those may sound like huge deltas today. And I understand why they are for somebody at a particular age. But much more important to the long term. value creation of one's career is putting yourself in a position where you're going to learn and where you're going to surround yourself with great people and where you can be a sponge, you know, that is going to drive much, much more cumulative earnings over a five or 10 year period than any short, short term differences in these different roles. I do not recommend maximizing for comp in the short term. So to the question of what I what I did when I left Zillow, you know, the first thing I did was I taught. So I created a course at Harvard Business School called managing tech ventures, which basically codified my 20 years of CEO ness into a course a class that was a lot of fun to teach, and distilling that into lessons and looking at case studies and writing new case studies, about companies was, was helpful to me to kind of get my story straight to sort of, you know, figure out how to communicate all these different things that I learned so far in my career. So that's the first thing I did was was teach this course at HBS. Then, the reason I started.la was because I've moved back to Los Angeles about four years ago, and I grew up in LA many years ago, and when I came back after 20 years of being away, I was blown away by the LA tech ecosystem. That it was vibrant. There were founders, there were entrepreneurs, there were VCs, there are unicorns, they were big public companies like Snapchat. There are big, you know, Silicon Valley public companies like Google and Facebook that have 1000s and 1000s of employees in LA. And it was just this really robust tech ecosystem. But there was no journalism, there was just there was nobody telling the story of the region. And, you know, Seattle has something called geek wire, which does a great job of covering Seattle tech TechCrunch does a good job of covering the Bay Area tech. And there was nobody covering la tech and so.la. Is is doing that is telling stories of innovation and startups and, and what's happening in the LA tech ecosystem. And we launched about a year ago, and it very rapidly became the most widely read resource covering la tech. I'm very proud of what we've accomplished so far. When I came up with the idea for.la, I went to my high school journalism teacher from my high school in LA and pitched her on this idea. And she said, this is a great idea, you should totally do it. I encourage you, Spencer, you should talk to this guy, Sam Adams, who was the editor in chief of our high school paper, 15 years after you. And so you don't know I'm Spencer, but I was your teacher. And then 15 years later, I was this other guy's teacher. And he was the editor in chief and you should meet him. And I met him and he is the CEO of.la. And the editor in chief and his name is Sam Adams, and he went to my high school 15 years behind me. And he was the editor in chief of the high school paper that I was also editor in chief of and, and we have our high school journalism teacher to thank for that. Anyway, so Picasso. I started with a former Zillow person, a guy named Austin Allison, who's a great founder, he started another company called dot loop that Zillow bought for a for a significant amount of money is a venture funded startup that is a real estate software company that Zillow acquired. And Austin and I have been lucky enough in our lives to own second homes. And having a vacation home is a real blessing. Especially when you have kids It is a place where you can get away where you can be the best version of yourself that you want to be you can be the type of husband you want to be, you can be the type of father you want to be. And, but but owning a second home is not accessible to most people, it's kind of it's kind of only for the 1%. And what we're endeavoring to do at Picasso is to make second homeownership more affordable and accessible and enjoyable to many, many more people through co ownership. So the concept of Picasso is to help people buy a portion of a second home. And by only buying a portion of it, they can afford it. And so we launched a couple months ago, and it is doing awesome. Many, many, many people are using the service to buy a quarter of a home in Palm Springs or an eighth of a home in Napa Valley or half of a home in Tahoe. And they're paired with other co owners of that home. And they use the Picasso app to manage visits to their home and Picasa does the property management for them?


And all the all the operating agreement of the LLC and all that right?

Spencer Rascoff  33:14

Exactly. We put out our handles all that. So it's Pac so and you know, hope your hope your listeners check it out.

Ash Faraj  33:22

I found your your annual review really interesting, what's important for your own self evaluation, because I guess this is the first year that you say that, you know, you're accountable to nobody but yourself. So how you self evaluate is teaching others investing in others creating future opportunities and constantly learning, right? So imagine you were in your mid 20s? Do you feel you would have the same buckets of self evaluation? Or would they be different

Spencer Rascoff  33:42

now they would have been different at that age, I suppose. So the priorities in my early 20s probably would have been make sure that I was intellectually stimulated by the place that I was, make sure that I felt appreciated by the people that I was working with. Make sure that I was learning every day, make sure that I was surrounding myself with people that would teach me and and coach me and mentor me and make sure I was in a place where I thought there was a rapid career progression in front of me, making sure that I had decent comp kind of good enough compensation to make ends meet but not prioritizing it not maximizing for it.

Ash Faraj  34:26

Something I personally look for when I decide to partner with someone or hire someone is

Spencer Rascoff  34:31

grit, grit. You know, it's it's a chip on your shoulder. It's somebody feeling like they have something to prove. You know, I just backed somebody, for example, who got laid off from a company and pissed off about it. And they were just like, you know what, I shouldn't have been cut with that group of people that got laid off, like my manager got it wrong. And I'm going to show him and that's what you know, that's what's motivating me and you know, some But it just feels they've got something improved. That's always something.


The most important quality in a leader is

Spencer Rascoff  35:06

empathy. Meaning being able to put yourself in someone else's shoes and see the world from their perspective,

Ash Faraj  35:15

something I've struggled with as a leader has been

Spencer Rascoff  35:17

micromanaging, it is hard. Man, I usually know how I want something done. And, but being a good leader requires delegation, especially at scale. And so sometimes I have an urge to just do it myself. But if you want to scale yourself, you need to resist that urge, and delegate. And when you delegate, sometimes it doesn't get done the exact way you wanted it to be done. But you have to accept that that's, that comes with territory and delegate,

Ash Faraj  35:48

when I start to feel the urge to be lazy, I

Spencer Rascoff  35:51

run, I drive and I try to run two or three miles a day, every day. I don't quite achieve that goal all the time. But you know, I probably run three miles a day most days. But the best cure for laziness is this exercise.

Ash Faraj  36:05

I feel like it's also connected to mental obviously, for sure. Together one setback or failure in my early 20s, I will never forget his

Spencer Rascoff  36:14

I didn't get a job at a pro I interviewed for and didn't get a job at a private equity firm in Boston that I really wanted. When I was when I was in investment banking, and leaving. And fortunately, I didn't get it. And that caused me to move to San Francisco to work at a different revenue from, but I really wanted that that other job that I didn't get and turned out. Okay,

Ash Faraj  36:39

so the moral of the story is everything happens for a reason.

Spencer Rascoff  36:43

Yeah, it's like, you know, it'll be fine. I mean, that's, I will say that, like, on the startup thing, people dramatically overstate the level of risk associated with startups. In in terms of, like, it'll be, I don't know, I was not worried about starving or hunger, or, you know, like, it's going to be okay. And so, a lot of these these things that seemed like crises at the time, like, I didn't get that job, or, you know, I got laid off or, you know, I'm taking this leap to start, I'm leaving this comfortable job as an accountant to go work in the music business, my dad's case, or I'm leaving this job in private equity to start up in my case, you know, they're not, they're not as risky as they sound in real life. So just kind of keep that in mind. And therefore be fortified. You know, when pursuing that risk,

Ash Faraj  37:51

the sweetest moment I felt in my entire career was when


probably speaking at an all hands meeting at Zillow a couple of years ago, where every year we, we used to not anymore, but every year, we used to fly all employees in to Seattle for a couple days of what we call Zillow week. And, you know, when I would take the stage, and there'll be a couple 1000 employees gathered, that was, that was pretty great. You know, I felt a deep sense of connection to them. And they to me, and felt proud of what I had accomplished and in getting helping them get there and then helping me get


towards the end of my career, just kind of foreseeing the future.

Spencer Rascoff  38:40

Not yet there.

Ash Faraj  38:42

If I could be remembered for just one thing,

Spencer Rascoff  38:44

it would be helping a lot of other people be successful, either by coaching or mentoring or by managing or elevating or enabling them. It would be awesome. Like the most fulfilling thing is, for example, financially, was not that I became financially independent because of the success I had there. It was when an employee would come up to me and say, I just paid off $20,000 in student loans, or I am able to take my family on vacation to Hawaii that I never thought I could afford, or I just bought my first home. You know, having that impact on 1000s of employees was far more rewarding in the aggregate than the impact that it had on me financially. So that's what I want to be remembered for is helping lots of people succeed in their career or succeed financially.


And the last one is if I were stranded on an island and I had access to just one meal, that meal would be

Spencer Rascoff  39:44

grilled cheese and bacon.

Ash Faraj  39:46

Really grilled cheese out of any meal

Spencer Rascoff  39:48

on white. Thanks. Yeah, okay, let's come up with food when you're when you're stranded. Yeah.

Ash Faraj  39:55

Thank you so, so much for listening. If you enjoyed this episode of please Please, please leave us a quick quick rating review can be super quick a few seconds on Apple podcasts. A quick rating review goes so long because we want your feedback. We'll know what you think. We take every rating review very very seriously. And we hope to see you again next week. Take care of my friends

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