WS2000 Episode 2000 with Spencer Rascoff

Looking for insights on real estate technology, navigating a demanding career, and achieving work-life balance? In this milestone 2000th episode of the Real Estate Syndication Show, we were honored to host real estate tech icon Spencer Rascoff.  Rascoff, the co-founder and former CEO of Zillow, shared invaluable knowledge from his entrepreneurial journey, offering insights for anyone looking to build a successful business and a fulfilling life.

.Spencer reflects on his journey with Zillow, discussing the company's expansion to more than 4,500 employees and its notable market capitalization. He emphasizes the importance of balancing his professional accomplishments with his family life, even amidst a demanding career. Additionally, Spencer highlights his commitment to continuous learning, especially with emerging technologies like AI, stressing the value of surrounding oneself with experts and embracing experimentation with new tools.


Here are 3 key takeaways from this episode:

1. The Power of a "Career Mirror":  Find someone who will challenge you and help you reassess your professional path.
2. Found Your Passion? Build a Culture Around It: Align your company mission with your values and prioritize servant leadership to cultivate a thriving work environment.
3. Continuous Learning is Key: Stay ahead of the curve by embracing new technologies like AI and surrounding yourself with knowledgeable people.

This episode is a must-listen for anyone in real estate, tech, or anyone seeking to achieve a fulfilling and successful life. Don't miss Spencer's insights and inspiration!

P.S. We've moved from daily to weekly episodes to deliver higher-quality content with prominent guests like Spencer. Stay tuned for more!

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Transcript

Whitney Sewell: This is your real estate syndication show. I'm your host, Whitney Sewell. Today, I have a very special guest for you. And before we jump into the guest, I have a special announcement as well. You may have already heard, we're changing the cadence of the podcast from daily to weekly, really in an effort to serve you better. We want to have bigger name guests on more often and to be able to produce higher quality content for you, which we are starting with today. Our guest today is a co-founder and CEO of 75 and Sunny Ventures. He's also co-founder and chairman of Picasso and a number of other very successful startups. He's also the founder of Zillow and was CEO of Zillow for 15 years. You're going to hear him talk about a number of things around Zillow and his time there today. During this interview, his name is Spencer Raskoff. During his time as CEO of Zillow, he won dozens of best in places to work awards and grew to over 4,500 employees, $3 billion in revenue, and $10 billion in market capitalization. And you're going to hear a number of things come from those experiences today. And while he has just an amazing bio and achievements, and he's been on CNBC and New York Times and bestselling author, all these things, You know, one thing I really enjoyed about the interview with Spencer is his focus on family. And we talked about that a lot. And we jumped into how he manages that dynamic and how he did when things were so busy. And what is that filter to say no? And you're going to hear his focus on family, which I really appreciated, which you all know. And I hope that you are doing that as well. You're going to hear also his view on the economy and what he expects through the end of this year and what he's doing and even how passive investors should be navigating the economy today. You're going to hear that and even some things that he's invested in and things he's not invested in as well, which may surprise you today on the Real Estate Syndication Show. Spencer, welcome to the show. I'm honored to have you on and to meet you and really for you to be our 2000th guest. So thank you again.

Spencer Rascoff: Thank you. Thanks for having me. And congratulations on the longevity of this podcast. I've, I've done a couple podcasts of my own. Uh, I think I got to about a hundred something episodes in one and 75 at another 2000 is, is next level. So congratulations and, and to the listeners, thank you for, you know, for, for sticking around and, and, uh, you know, congrats on, on 2000 episodes. It's really quite an accomplishment.

Whitney Sewell: I appreciate that in a big way. And, and, you know, Spencer, I want to begin with a really a different topic, I think, than most I've listened to many interviews that you've done over the last few days, or actually that you've recorded over the last few years, probably learned a lot about you. And something that resonates deep with our audience and with me personally, is really this balancing this dynamic between the being that CEO and pushing this professional success, right? But also, man, being famous at home, right, as well. And so I just wonder how you have managed that well, because it's often not done well. And I speak at conferences and I hear people talk about, man, just going and conquering and doing all these things in business, but there's not much talked about about how they still are famous at home and do that well. So how have you done that or balanced that well?

Spencer Rascoff: Well, so I've been with my wife since we were 17. Um, we, we started dating right before college and, uh, and dated all through college and, you know, we're now 40, 49. So we've been together a long time. So when you're with somebody from the beginning, um, there's a certain humility. So, I mean, by, by which I mean, um, you know, I can win business awards, or I can be on TV, or I can achieve business accolades. And at the end of the day, my wife still sort of, and I mean this in a loving great way, she still treats me like the idiot 17 year old that she fell in love with. So Um, you know, there's really no impressing her with, with any great business accomplishments. And the result of that is it keeps me humble. You know, I'm, it's like, whenever I think I might have achieved any great business success, it's like, no, no, no. You know, you're just, you're just, you're just Spencer.

SPEAKER_00: So, um, so I, I think the, you know, the.

Spencer Rascoff: The way I behave at home is to try to be a great dad and a great husband. And I'm really, you know, it can be a bit of adjustment, of an adjustment, especially when I was managing very large teams at Zillow. So I would have you know, teams of handlers and PR people and, uh, you know, multiple assistants. And then the, uh, you know, the sort of home life is, is very different than that. But, uh, I, to me, I, that sort of keeps me grounded and I think it's been a recipe for great. home life happiness and a successful marriage and a successful home life. You know, the only other thing I'd flag on this is how things have changed now that most of us are working from home. You know, it looks like you're probably that looks like kind of a residential background. I'm guessing you work. I'm guessing you work from home. I work from home now. I do. And that's quite different. You know, on the one hand, it's nice. I've got kids at home still and they get to see me work and they get to understand my work ethic. It's no longer sort of out of sight, out of mind, where when I used to go to an office and they wouldn't really think about it. I think now they've got a better conception of what it is that I do, and I think it's valuable for them to see literally out of the corner of their eye me working. But it can also be hard to create boundaries. It can be hard to turn off work. It used to be a lot easier when I went to an office. At the end of the day, I'd come home, and I would leave my cell phone with my car keys and not look at it for a couple of hours, and work was done. and now I was home. Well, nowadays, obviously, we don't have those clear boundaries. So that can be that can be difficult. And I encourage people to try to find ways to create those boundaries for their own mental health and also for the success of their family life.

Whitney Sewell: Yeah, you know, are there are there filters maybe that you have, you know, where, you know, you know, when to say no to something, because oftentimes, you know, maybe there's I was even invited recently to speak at a very large conference. And I've been there many times. But most people say you're crazy not to go take advantage of this opportunity. But there's some things in the family side that, hey, I knew that I wanted to be there for those things. So I just said, you know, I'm going to I have to say no to that thing, you know, but, you know, it's difficult or there's a tension there, but is there filters that, you know, you've used to say, you know, what is amazing as this opportunity may seem, I'm just going to say no to it this time. It allows you to say yes to something else, right?

Spencer Rascoff: I do it all the time. And, you know, I mean, what I'm doing today, today in 2024 is investing in startups and starting new companies and coaching and advising and counseling. And so there are a number of Jobs that I have today where I charge rates for my time so I think that's been a very helpful construct because it helps people it helps me make decisions about about certain things, you know, it's like Do I want to, like, how much is that thing, even if I'm not getting paid for something, how much is that worth it to me? I think actually I would encourage everybody to start thinking about an hourly rate for their time. you know, even if you're not, even if you don't get compensated that way, just as a benchmark to assess certain things. And then the second thing I would suggest is once you've created that, then you want to be careful not to fall into that trap. Because let's say your hourly benchmark is $1,000 an hour, that's kind of what you what you get compensated for 500 an hour, or whatever, you know, whatever the number is. Now, you're like, okay, do I wanna go to that kid's volleyball game or should I work for those two hours? Well, that's two hours, $500 an hour, that's 1,000 bucks. Okay, would I pay $1,000 to go to the volleyball game or would I work for that? And the problem with that construct, even though I do think it's helpful to have kind of on the proverbial whiteboard, The problem is that time is fleeting, and I've observed this as my kids are older now, my kids are 18, 15, and 12, and a volleyball game or a soccer game or a kid's performance that I perhaps might have missed five years ago I would absolutely pay that thousand dollars today to go back in time and experience that. Especially now that kids are older and they need me less, want me less, and I can now work more. Time is money, but also the exchange rate of the currency is changing over time. If, if you're a great parent and as kids get older, that exchange rate changes as your kids need you less and want you less. So that's another important thing to keep in mind.

Whitney Sewell: I love that thought process. Not so much, would I pay $1,000 to be there today, but would I pay that 10 years from now to be there today ultimately at that game and build that relationship?

Spencer Rascoff: There's a great book, Whitney, that I recommend called Die With Zero, which has a very provocative title, but what it argues is that we delay gratification too much. We, we aspire to accumulate wealth too much. And we, you know, that like, for example, the, Oh, I'll get that ski house later when I have more time and money. It's like, okay, well, what, you're going to wait until you're fifties or sixties or seventies, and you can't really ski anymore because your knees don't work. or, you know, I'll wait to go on that safari with my family until I have more money. It's like, okay, but if you wait too long, your kids don't want to go on that safari with you anymore because they have their own lives and they don't think you're cool anymore. So like you, the book argues, and I subscribe to this, this philosophy that you want to, maximize life experiences and be really cognizant and intentional about how to achieve those experiences at the right times. Because if you just wait, wait, wait, it'll be too late. You know, you'll have plenty of money, but you'll be 80 and not no longer able to enjoy your experience the the fruits of those labors.

Whitney Sewell: Yeah, I think it's a great point. That book prompted me to take my mother on a trip.

Spencer Rascoff: Oh, you read it? Yeah. Oh, cool. I don't usually encounter people that read it. Oh, that's amazing. I've read it.

Whitney Sewell: Yeah. We took my mother on a trip and my sister and her family as well. And that prompted that because it made me think about, well, wait a minute, you know, 10 years from now, she's not going to be able to go on a trip like that either.

SPEAKER_02: That's awesome. That's exactly. Yes. Good. That's amazing. That is exactly what the book argues. And I'm so glad that it's had an impact on you as well.

Whitney Sewell: Yeah, one other question on this topic. Any family rhythms that you found just to help you to cultivate those relationships? You know whether you know as a husband or Anna as a father or anything, maybe you know what I I made sure that I had this on the calendar every month or maybe it's a date night or something like that.

Spencer Rascoff: The thing that comes to mind is kid trips alone. So I have three kids. We have a very close-knit family. But a trip with the five of us is very different than a trip with me with one of my kids. So my wife and I try very hard, and we usually achieve it, to each of us do at least one trip with just one kid each year. And I'm planning the ones right now. I'm taking my older daughter to Europe for a couple of days. I'm going to go to Colorado with my middle, and I'm going to go to, I think, Wyoming with my youngest. So just even, you know, two, three, four days alone, parent-child, I think, is really important.

Whitney Sewell: Yeah, love that. Well, you know, I've heard you mention in some other interviews about this career mirror, right? And, you know, someone that reflects back to you the reality, you know, right, of your growth and journey. Could you just, I guess, share a little bit about what that is for our listeners and maybe how this has helped shape your decisions?

Spencer Rascoff: Absolutely, absolutely. Um, every major career decision that I've made has been impacted really, really catalyzed by my wife, who I think of as a career mirror, meaning that she's close enough to me to see things that I wouldn't see, but she also has a little bit of distance from my day to day work. So. Telling me that I'm unhappy at a job or even before I realized that I am or telling me that I want to be doing something different professionally even before I realized that that I Should be you know thinking about new challenges like that's the role that she has played and I think it's very important for people to have somebody like that in their life it can be a spouse a friend a parent a a coach, a priest, it can be anyone in your life, but I think that is invaluable. And, um, uh, you know, when I left Goldman Sachs to go to private equity, she, she catalyzed that when I left private equity to do a startup, she catalyzed that when I sold my first startup and she said, I was unhappy at the big company that we had sold our, our startup to, she catalyzed that. So, um, you know, that's been, it's been really invaluable in my career. And I, I wish everybody would have something like that in their life.

Whitney Sewell: Can you speak to how does that, I guess, occur? Or is it like when there's a big event that happens and then you all kind of come together to reflect about the situation?

Spencer Rascoff: No, it's more it's a little bit it's more organic, at least in my in my case, it's been more organic. And again, it could be because she's. Assertive, you know, she she's uh, she'll just tell me like hey, you know you I don't know I'm not sure if you if you're aware of this, but you don't seem as motivated or fired up as you were a year ago When you were doing something slightly different like let's talk about What you should be doing going forward. So it can be It could be introduced by a particular life event, but at least in my cases It was just her own assertiveness. And the problem is that people are busy. And you know, you if you have your head down, and you're just sort of plotting ahead, getting to the next performance review, getting to the next vesting date, getting to the next hundredth episode of a podcast, you know, you, you may not pick your head up and say, hold on, wait a minute. Like, does this still make sense? Do I still want to be doing this? Is this still the best use of my time? Um, and so that's where a third party can be really valuable to stick their nose in and say, hold on, wait a minute, time out.

Whitney Sewell: Love that. And is that, say, different, this career mirror, is that, you know, and it's your wife, is that different, say, than or how you would treat other mentors, you know, the people that influence you like that?

Spencer Rascoff: Well, most of those other folks you're trying to impress either intentionally or subconsciously. So it can be difficult for a mentor to play that role. Um, it's not impossible, but frequently a mentor is at your own company or they're in your professional orbit. So in my experience, it's, it's been, um, advantageous for the person to be. Kind of you know halfway in halfway out and you know in my case a spouse So so I mean she's in my life obviously, but she's not in my day-to-day professional life I think it would be harder if it were somebody that were in your day-to-day professional life, but you know again the most important thing is just that there's somebody there to you know to press the pause button and prompt you to evaluate where you're going and where you've been and

Whitney Sewell: Yeah, no, that's very helpful to think about the difference in your, your spouse. Hopefully you're able to receive feedback from your spouse, right? Mine has also been, uh, just, uh, I mean, so crucial in so many decisions made, even in business, even though she's not in business, she has said things that have just been helped me to change the, or pivot, uh, that's been so instrumental that I wouldn't have expected even. Right. And I've grown to like, expect it, like ask her questions, knowing that she's going to speak into, uh, these decisions that are so important. Um, so. Changing gears again, Spencer, a little bit, and even thinking about how you have a desire to continually learn, right? And this continuous learning, and it's something that I've grown in over the last number of years. Wasn't taught that really young, unfortunately, but I've grown to know just, hey, I want to read, want to read, want to learn, want to learn. Just wondered, as busy as you are in your schedule and over the last many years, do you have a method for that? How do you take in content or good quality content so you're continuously learning and growing in personal development?

Spencer Rascoff: Well, this is a great question. And I think AI is the perfect litmus test for this because we've all heard about AI over the last 6, 12, 18 months. it can be pretty intimidating, right? You're like, okay, I know I need to figure all this stuff out, but you know, am I, am I too old? Or like, where do I start? And like, I was talking recently to a startup CEO tech exec in his mid fifties, who's had incredible success. He started companies, he's taking companies public. He's, you know, he's a really great tech executive. And he confided to me, he said, you know, I'm just like, on this whole AI thing, I'm kind of throwing my hands up. Like, I know it's important. I know it's going to change the world. But I just don't really want to jump in and figure it all out the way 5, 10, 20 years ago, I did jump in and figure out cloud, or mobile, or search engine optimization, or whatever another arising tech change was at the time. And, uh, you know, and, and I was like, okay, you know, again, life is short, you know, die with zero, that's totally fine. Then, then don't. Um, and I'm sure there will be a time when I feel that way about some other future tech development, maybe it'll be five years from now, maybe it'll be 25 years from now. I don't know. Um, but for now I'm still motivated and interested and curious. The way to answer your question, the ways that I learn, um, I like to learn by talking with people. I learn by listening. And so for AI, for example, I try to surround myself with great people that understand these issues better than I do. And I ask a lot of questions of them almost in a Socratic way where, you know, and, and An ancient Greek pupil would ask questions of his tutor to learn a topic. And you're supplementing that with book learning, with reading. But the ancient Greek way of education was very much more of a one-on-one tutelage, verbal method of education. So, uh, so talking with lots of people and then tinkering myself. So, uh, you know, I'll ask some of my AI friends, like, you know, what are a couple of great tools that I should play with? Okay. Um, you know, Hey, Jen is a very cool tool that helps create AI generated videos. So I checked it out. I downloaded, I got a subscription for a month. I created a bunch of videos of myself using AI and then my kids using AI and I got it. And then I, I, cancel the subscription, like I get it, I can move on and go try to tinker with and play with the next, you know, the next set of tools that are that are recommended to me by experts. So that's how I learned.

Whitney Sewell: Yeah, a lot of that. You talked about the one-on-one and asking questions sounds like a good podcast, actually.

Spencer Rascoff: Yeah. I mentioned I had two podcasts. One of my podcasts was Dad, I Have a Question, which is how I taught my son. So my son was, I guess he's 15 now, but we did the podcast from about age 10 to age 13. And he would ask me a question. Dad, what is crypto? What is blockchain? What is inflation? How do banks make money? What's private equity? What's venture capital, et cetera? And I would teach him the answers to those questions, and then we would discuss it, and then he would play it back to me as he would teach it to a peer of his, to a kid. So it's a great podcast for kids to learn these issues, and also for adults to learn about these topics. But that's an instance of me in the teacher role, teaching a younger person. But in the case of these emerging technologies, I'm usually the student, not the teacher.

Whitney Sewell: Yeah, I like that. And I've listened to a few of those. And I love it that it's that it is, you know, it's it's taught in a way that a child can understand, right? So I can understand it, too.

Spencer Rascoff: Yeah, I get a lot of feedback from from parents that way that are like, Oh, yeah, I started listening to it with my kid.

Whitney Sewell: But actually, you know, I think I heard you say one time that there's oftentimes those are conversations that come up around the dinner table.

Spencer Rascoff: Yeah, I mean, the way the whole podcast started was it was organic. I mean, my father-in-law would listen to these conversations and he was learning and he would say to my son and me, he'd say, wow, this would make a great podcast. So that's where it came from.

Whitney Sewell: Awesome. You know, another thing you talk a lot about is the founder product fit, you know, and just the importance of that. And, you know, I think it speaks volumes, different things I've heard you talk about around that and, you know, the way people can be motivated about a product because they are just so ingrained in what it is. And, and, but, you know, could you just elaborate on that a little bit and maybe how you assess that, that fit?

Spencer Rascoff: Um, so there's no such thing as just a great founder. In my opinion, there's only a great founder for a particular idea. You know, if you asked me to go start a biotech startup, I would be terrible at that. I'm just not interested in it. I'm not motivated by it. But if you ask me to create a two-sided marketplace that uses information transparency to democratize access to some asset or information that was previously inaccessible to most people, that's my jam. I've done that in real estate. I've done that in travel. I'm doing it in real estate again right now. Those are the types of things that I'm motivated by. So that's what I'm looking for. I'm looking for a founder who deeply connects with a product or mission or strategy. And the example I like to use is this guy Garrett Rothstein, who is my co-founder of a startup called Q, Q-U-E-U-E. You know, Q is a streaming discovery app. So it lets you figure out what to watch on TV or what movies to watch based on what your friends are watching. And I remember when he and I were first getting to know each other and we were talking about whether to start this company together. I said to him, I said, Garrett, what would happen if I told you, you couldn't do this startup, you know, for whatever reason, you just couldn't pursue this idea. And he just looked at me kind of wide eyed. And he's like, Spencer, like, you don't understand. I was put on earth to solve this problem. I wake up every morning trying to figure out how to help people figure out what to watch. I go to sleep every night trying to figure that out. Like, this is what I was meant to do. I have to do this. I would do this for free. And that to me is founder product fit. That's a founder that connects deeply with the challenge and mission, the problem that that company is trying to solve. And, you know, there are plenty of other people that would not be motivated by that, but Garrett uniquely is. So that's what I'm looking for when investing or when starting companies with people.

Whitney Sewell: What about when the, you know, and I'll use myself as an example, you know, our mission really at life bridge capital is, is helping families be able to bring their children home to adoption. And so we have a foundation that helps families with financial grants and whatnot, but, but we fund that through the commercial real estate business. Uh, and so obviously we have four children through adoption. And so that's a big passion of ours is helping these families. Uh, but, but it's, it's, uh, so it became the mission behind life bridge capital. right in the commercial real estate business. But it's kind of, you know, it's not, I guess, directly commercial real estate, but it's, that's how we do it. Does that make sense?

Spencer Rascoff: Yeah. Amazing. I mean, good for you. That's fantastic. You found a way to, to, um, you know, harmonize your, your business with your, with your civic and philanthropic and, and, um, uh, you know, mission driven goals. So that's awesome.

Whitney Sewell: Have you ever passed on a project maybe that you thought later, Hey, I should have been a part of that, but, you know, because it wasn't a good founder. Um,

Spencer Rascoff: I've passed on a million or not a million on many, many, many hundreds of companies that I think are good ideas. The founder seems good. The company will probably succeed, but I'm not personally connected to it. I just don't really care very much about that, about that particular topic. Um, and so I'm not the right collaborator or investor for, for that particular person. Um, uh, you know, I can't, uh, um, A lot of VCs keep a good track of what they call their anti-portfolio, kind of the ones that got away. Because I'm not a real VC, I'm an angel investor, I haven't really done that because the way I approach investing is much more like coaching. I mean, what I did for 20-something years was I was on the field playing at a professional, at a very high level. And I'm on the sidelines now, and I'm comfortable with that. That's where I want to be. Because playing on the field professionally, you get a lot of bruises, and it is all-consuming, and there are a lot of injuries, and it's a lot. And coaching is still intense, but it's a different level of intensity. I do that coaching and teaching and mentorship in a lot of different ways. I do it by investing in startups. I do it by starting companies with other co-founders. And I do it by teaching in college and in business schools and doing podcasts. And I get compensated in different ways. for that teaching, coaching mentorship. And sometimes I don't get compensated at all. I just do it, you know, out of, out of interest. Um, so, uh, anyway, to, to answer your question, like I am the, the, the framework that I use when thinking about investing isn't always monetary. It's frequently, do I think I can be a good coach or mentor to this founder? And would I learn from doing that and spending my time doing that? So it's a little different than a traditional venture capitalist that's just maximizing return.

Whitney Sewell: Yeah, I don't think I've heard anybody phrase it like that before, like approaching investing, like coaching. So I love that you're investing in this founder and their business and, and hopefully their growth, uh, but yours as well. And you're going to learn from that. I love that. Uh, you know, and, and speaking of, uh, just investing, you know, I get questions, but I'm sure you get this question a lot more than I do, but like, what's going to happen, what's going to happen, you know, over the next six, 12, 18 months. And, and I want us to go there a little bit, but, uh, but. But, you know, often I say what we none of us know exactly, of course, but what we believe is going to happen affects what we're going to do, what we're doing now. Right. And and so I just wonder your thoughts of the economy over the next six, 12, 18 months, anything you're bullish, bearish on trends, anything like that.

Spencer Rascoff: Uh, well a lot of my companies are in the real estate tech space or the prop tech space and as as is yours and That's deeply impacted by mortgage rates. And so I you know, I like most people in the real estate industry have been Holding our breath waiting for the fed to cut rates this year and as inflation has stayed stubbornly high the fed has been very Cautious to start lowering rates and they haven't started lowering rates So I I think there will still probably be two rate cuts in 2024 Going into 2024. Most of the experts thought there would be up to six rate cuts and that clearly is not going to happen so what I think will happen is there will be Two rate cuts this year probably in the summer in the beginning of the fall Then we'll have the presidential election. I hope for a It's crazy to say this, I can't believe I'm about to say this, but I hope for a peaceful election. Whatever the outcome may be, I have plenty of personal opinions about what I hope the outcome will be. I tend to keep those mostly to myself. But mostly, I hope it is a peaceful and uncontested outcome on both sides. And we won't know that until probably late November, uh, maybe even into the first quarter, depending upon what, what happens. So that to me is the wild card. And I think I, like many executives are going to be kind of in a, in a hold your breath mode from October through January. And remember the elections in early November. Um, but it's going to be a couple months, you know, a month or two before, and a couple months after, before we, we know that it's sort of settled.

Whitney Sewell: Yeah. Yeah. Any, you know, it's a good thought. So holding your breath from October, uh, you know, maybe through what? No, uh, November through inauguration, I guess, at least, at least through January 6th, not to get too political, but, but, you know, that, that will be an important date, I think, uh, to, to get past any, any advice you would give to passive investors today, just navigating the current climate in the, in the things that you've mentioned.

Spencer Rascoff: I was lucky enough to be on the board of trustees of my high school and my kids' high school with Charlie Munger for many years. Charlie was on the board for 55 years, I think. I've been on that board for maybe seven or eight. And so we overlapped for the last seven or eight until he passed away. So I learned a lot from Charlie. And I think the most important thing I learned from Charlie was the importance of patience in investing. and the power of compounding and the importance of buying great businesses at good prices. But when I say buying, that includes investing in. And the world that we live in today is very minute to minute, itchy, you know, like a like a itchy trigger finger. I think that's the expression. But, you know, the media, the social media, but also business TV encourages this kind of fast twitch reaction to everything, everything political, everything business, everything economic. And that's a terrible way to invest. There's a great, I remember a friend of mine at Goldman Sachs once showed me a really interesting analysis, which looked at stock price appreciation over the last 30 or 40 years. across different indices. And the point that the slide made was that it is impossible to time anything. If you're like, oh, the market's hot, I'm going to pull, I'm going to sell, and then I'll come back in when it cools down. I forget exactly what the data said, but it was something to the effect of, if you were out of the market on just, I think it was like 12 days over the last 30 years, your rate of return would have been, I don't know, 30% lower or something than if you had just stayed in it and buckled your seatbelt. In other words, none of us have any idea. Timing things is impossible. Just, you know, try to keep fees low and enjoy the benefits of compounding and buy good businesses at decent prices and then try not to overly obsess about it day to day.

Whitney Sewell: Yeah, love the focus on patience, for sure. If I heard correctly, I think that you don't own any real estate directly, right? I don't.

Spencer Rascoff: I mean, I have a couple of personal homes, and I own a Picasso, which is a portion of a home in Malibu, but I do not own any real estate investments.

Whitney Sewell: Is there any, I guess, what are your thoughts behind, let's say, not owning real estate directly or, you know, investing in real estate directly?

Spencer Rascoff: around the complexity and the sort of inaccessibility of the asset class. This is one reason I love Picasso when I started the company. And one reason I invested in another startup called Arrived Homes, which I'm an advisor to. And Arrived Homes lets, I do own some real estate through Arrived. So I created an account with Arrived and I buy, you know, I've bought, I don't know, tens of thousands of dollars of single family rental properties just through Arrive, through their platform. So I don't even remember where they are, or all I know is I own tiny little pieces of it, and then Arrive does all the property management, and they just send me the dividend check. And Picasso is something sort of similar for co-owned vacation homes, but you get to enjoy the home instead of just using it as an investment. So trying to create accessibility for those asset classes is something I'm very interested in, and that's why I've invested in and started those two companies. It just feels sort of daunting. Like where would I even start if I wanted to go buy what, like a mini mall or a apartment building or an office complex? Like I wouldn't even know, I guess I could call a commercial real estate broker. Uh, but, um, uh, you know, it's illiquid, it's, it seems complex. Um, uh, so those are the reasons why I haven't done it. It's, it's not because of any asset allocation, uh, strategy. It's more just the, the inaccessibility.

Whitney Sewell: Yeah. It sounds like, uh, I mean, you're, you're harnessing what, you know, right. What you're familiar with and startups and businesses and, and, and really focusing there versus pivoting into something that maybe you, you don't feel as comfortable with as, as that.

Spencer Rascoff: That's exactly right. That's exactly right. I mean, I'm an investor in over a hundred or around a hundred startups. Uh, Um, and I probably, you know, it's an interesting question. I try not to ask, ask myself this question too much, but if instead of investing in those hundred startups over the last couple of years, I had just put it, I put all that money in the S and P 500, uh, or if I had put it into a couple of commercial real estate projects or residential real estate projects, What will be the best financial outcome of those three different scenarios? My guess is investing in the startups, which is what I did. It probably is the worst of those possible scenarios. I know this is strange to say, but I'm not necessarily trying to maximize, uh, you know, return on my investment. I'm, I'm also doing it out of interest because that's kind of, that's what I want to do is I want to spend time with founders that are trying to build cool companies and try to help them any way I can. And that to me is the business model of, of coaching the business model of mentoring, the types of, of. Executives and founders that I want to spend time with is angel investing. So that's why I pursue that business model.

Whitney Sewell: I think it speaks volumes to you and where you're placing the value, right? You're investing in these people and in a big way and not just even the founder, but their whole team, right? By getting behind them. I think that speaks as well to how you, I think I heard you mention numerous times that one of your greatest achievements was the culture at Zillow. uh, that was created. Uh, you know, could you elaborate? I feel like, and even before you do, I like, I just feel like that's so important. Is it something that we all kind of think we're doing or trying to do and can't do really well? And, uh, uh, what was that culture and how did you all create such a good culture there?

Spencer Rascoff: So great people properly motivated, build great products, which attract huge audience that generate revenue and profit and shareholder value. So it starts with people and Uh, and you know, we did this very, very well at Zillow the 15 years that I ran it. And, um. I think the most important thing to do is to articulate a mission and make sure that people understand how their work connects to that mission. So the mission of Zillow was to turn on the lights, to empower people with access to information, to create information transparency, um, and help people make smarter decisions. And that's a, that's a cool lofty mission that will get people out of bed in the morning and going to work. The mission of PICASO is to make the dreams of second home ownership more accessible and affordable to more people. That also is a really cool mission, because owning a second home is awesome. And I want that to be accessible to many, many, many tens of millions of more people around the world than it would otherwise be accessible to. And the people of PICASO and the people at Zillow feel really deeply connected to that mission. It's always communicated to them, they understand why they're there and how their work levels up and ladders up to achieving that mission. People also want to feel fairly compensated and then have autonomy provided to them. And this is one reason why I hate the word boss. I never use the word boss. To me, boss is a verb. It means to boss someone around, to tell them what to do. And that's not what a manager should be doing. A manager really shouldn't I don't even like the word manager, but I haven't found a good replacement. But I know what they shouldn't be doing, which is bossing their direct report around. So a good manager is somebody that practices servant leadership, somebody that inverts the pyramid where the more senior person essentially works for the more junior person. And the more senior person says to the more junior person, how can I help you? How can I clear your roadblocks? What can I do for you to make you more successful at your job? And the junior person says, oh, what I really need is I need feedback on that thing that I sent you three days ago. I need you to clear this roadblock by telling your peer that he needs to run his organization differently. Or, you know, I need you to help me close this candidate. And a good one-on-one is one where the senior person is taking notes, and the senior person is receiving the to-dos from the junior person. Okay, so I ask you, who works for whom? Well, to me, the more senior person works for the more junior person, because the junior person is staffing the senior person with the to-dos. So that is servant leadership, and that's very different from the traditional hierarchical boss culture. So those are the types of things that we try to do well at Zillow and I think as measured by Third parties and as measured by our employee engagement studies, you know we did a really great job and it that company culture is absolutely what made the company so successful and and allowed us to build great products and then achieve a lot of shareholder value

Whitney Sewell: Love that. There's a couple of great books on servant leadership as well. I could not agree with you more. And is there, is there like one or two tips that you would leave with the founder, the CEO that's listening right now that wants to strive to be that servant leader some way they can implement something even today?

Spencer Rascoff: Praise in public and criticize in private.

SPEAKER_00: Uh.

Spencer Rascoff: And make sure that the mission of the company is well known. And I mean, at Zillow and Picasso, we started every company meeting by reciting the mission in unison. At Picasso, because we're a hybrid company, home-based, every employee has the mission. It's just over my shoulder here. So we send physical copies to everyone to their home offices. So make sure the mission is well communicated. Make sure that you lead by example by practicing servant leadership.

Whitney Sewell: Spencer, just a few final questions as we just have a few minutes left. Unfortunately, I could talk about a number of these things all day with you, but a lot of people wonder, you know, somebody like yourself, what are some daily habits that you are disciplined about that have produced the highest return for you?

Spencer Rascoff: Uh, I stay very caught up on email. I don't understand the people that are, that are, you know, let their email inbox get to hundreds or thousands of emails. I basically managed each of my email accounts to inbox zero. And that's an important way I stay organized. Uh, I don't have a to-do list instead. I use my calendar as my to-do list. So, uh, you know, if I need to write a blog post about something, I'll create a calendar invite to myself for half hour for this afternoon. saying, write this blog post, and then I'll have the notes in the notes section of the calendar invite. If this afternoon comes and I don't get around to it, I'll take that calendar invite and send it to tomorrow or next week or next month. So I manage my whole to-do list through my calendar. I'm pretty hardcore about flipping my phone to airplane mode when I need to concentrate or when I'm with my family or certainly when I'm asleep. To me, if messages are still coming into the phone, even if it's turned, you know, even if it's on vibrate or silent or do not disturb, it's still as distracting to me. I still know that life is piling up. And so to me, switch, I switch it to airplane mode as, as the, the way to just put the big stop sign and make sure that nothing else comes into it. Um, uh, I exercise regularly. Uh, it's very important for mental health and also for longevity. And, um, you know, I don't know, those are some personal habits that I have.

Whitney Sewell: Number one thing that's contributed to your success. Just one, my wife. And how do you like to give back?

Spencer Rascoff: Uh, I give back by, by coaching and, and mentoring younger versions of me. So people in their twenties and thirties who are building their companies and who I can think who I can, I can help, uh, I can help them succeed through my advice and, and, um, and connections. The nonprofits that I'm interested in that I focus my philanthropy on are educational nonprofits and also homelessness here in Los Angeles where I live. So those are my nonprofit focuses.

Whitney Sewell: Awesome. Spencer, uh, grateful for your time, getting to meet you, have you on the show? Uh, very thankful for your transparency and just sharing your experiences. I know there's a number of things that I would love to have gotten to today, but we didn't have time. Uh, just, you know, as you have done so many things, uh, successfully and, and learn so many things to, uh, just, I wanted to get to the hotwire stuff and even, uh, you know, how you scaled so quickly and 200 hiring 200.

Spencer Rascoff: You can have me back for your $3,000. Hey, I would love that.

Whitney Sewell: I would love that. Thank you for having me. Thank you so much. Well, I hope you enjoyed the interview with Spencer Raskopf. I know I did. I learned a lot from him. I've learned a lot from him already just researching about him. And I hope that you are encouraged that even someone operating at that level can focus on family, can be dedicated in investing as well, and as a CEO, and you can do the same. I know, hopefully you heard in the beginning of the podcast that the Real Estate Syndication Show is transitioning to weekly versus daily and in an effort to produce higher quality content and to have more consistent, bigger name guests on just like Spencer today. So I hope you enjoyed the show. I hope that you will also share it and subscribe as well. Have a blessed day.