#165 Former CEO & Co-Founder of Zillow, Spencer Rascoff: Real Estate Voyeurism

I always looked at people 10 years or maybe 15 years my senior and said, "Do I want that life?" Not just the job. Do I want their compensation, their title, the respect they have in the community, the type of work they do, the lifestyle, the relationship they have with their friends and family? Look at your company or at your career path and look 5, 10, 15 years ahead and be really intentional about it. Because otherwise you'll wake up in the blink of an eye and you'll have that guy's job or that guy's job 5 or 10 years from now and do you want that? Hi, I'm Juben, operating partner at Cliner Perkins and I'm excited that you're tuning into grip. The goal of this is not for it to be a highlight reel of how successful my guests are, rather a candid exploration of how art it is both personally and professionally to create, build and scale world-class organizations. If you're a fan of the show, please subscribe, leave a review and make sure to follow us on LinkedIn or Twitter. I probably did find it on Zilla, I can't remember for sure. I did buy another house that we bid X for and they countered it Y and then we bid X and they countered it Z and Z was a really weird number, like 7, 8, 2, 4, 3, 5, whatever. And I remember asking my agent, like, what is that weird number? And he's like, that's the estimate. So the seller, the seller actually countered it exactly the estimate and I didn't realize it. Yeah, so I have been, have sometimes had to be on the receiving end of real estate irony. When you walk around now in LA or neighborhoods after Zillow, do you have a different appreciation for just like homes, neighborhoods, generally like communities that people live in? Definitely. I love real estate and I walk around all sorts of places with the Zillow app. But on my phone, looking at home values, I just did that the other day, gosh, where was I? Well, I did this when I was in South Carolina for the first time this summer. You know, it was there on vacation and pulled out the Zillow app to see what houses were worth and I just did it in Newport the other day. So yeah, I love real estate and I love real estate voyeurism. Do you miss it? You're keeping yourself busy, but in very different ways. Your version of busy today, which by the way, may even be more busy than you've ever been based on what I could tell. But it's very different than running a whatever 3000 plus person organization. Different miss that? It is very different. Today I am very involved in but don't run five companies and then I'm an investor in almost a hundred more. So I spend all day today context switching between different startups and providing advice and counsel and mentorship to other founders who are trying to create their own Zillow. Do I miss the Zillow experience at all? I miss leading large groups of people. I enjoyed that a lot and I also miss having access to much more resources. The nice thing about running a company like Zillow is you're playing poker with a very big stack of chips and when we saw an opportunity, it was very easy at Zillow to say, hey, let's throw 20 bodies at that. Let's throw 5 million bucks at that or we saw a company want to buy. We would go buy it and being able to make big bets, big bold bets is fun and almost every company I'm involved in now is incredibly resource constraint where it's the opposite. It's instead of, hey, let's place big bets. It's, hey, how can we run leaner? How can we place fewer bets? How can we be more focused? And so that's a very different position to be in. It's playing poker with a small stack, not the big stack. And how long has it been since Zillow for years? I left about four years ago. I joined KP about four years ago, meaning I left full time operating in the traditional sense and went into more of a, it's different, right? It's kind of similar to what you're doing. And I definitely, after four years, get the feeling that, okay, like they're doing the hard thing and sometimes I miss the hard thing. This feeling of being in it, rather than on the outside looking in, giving a limited set of advice that may or may not be helpful, sometimes I almost feel guilty. Well, I had one operator turned VC described this feeling to me in the following way. He said, you know how when you're watching like the Super Bowl or the World Series or something. And you imagine the Super Bowl, the team wins and on the field, they're going crazy and you know, my God. And then they flash to the owner's box and there's some old guy in a tie with cufflinks and he's kind of awkwardly high-fiving his grandson. Like that's the VC and on the field, those are the operators. And so the highs are not as high, the lows are not as low when you're up in the owner's box. It's a different perspective. I would describe it a little bit differently maybe because maybe I think I am not really in the owner's box. I'm kind of on the sideline. And I would describe it as I'm a former player who had a really great career on the field, won a bunch of championships and performed really well with great teams. And now I'm a coach and I'm trying to have a great next chapter as a great coach. And there are a lot of former players that became great coaches and ended up having even more success coaching and more leverage coaching because you frankly can coach for an extra 30 or 40 years after you're done playing. But playing is exhausting. You get injuries. You know, it's all consuming and coaching is also intense but is a slightly different proposition. How old are you? You're still pretty young. Like you started hotwire at 23. 23. Yes. Zillow started, I think I started Zillow at 30, frankly. 30, yeah. My point is like, let's take this analogy to the logical extreme of the player coach thing. Yeah. It's like if Brady retired after five knowing that he left a couple more potentially on the field and he's young, when Brady talked about the end of his career, the way that he reflected on it was like, look, it's like, going into a test and knowing all the answers. Now, I think that business is much different and I think each business is its own unique thing. But there is some level of confidence in knowing what to do and who to do it with in a lot of different degrees. Do you feel like you're going to do one last dance? Do you ever get that feeling? It's possible. It's possible. I mean, I get calls about CEO roles all the time. Of course. And I've turned a lot of them down over the last four years. I don't have any regrets about the ones that I've turned down. I'm always happy to hear opportunities and I tell recruiters they call me when I turn the roles down. Keep them coming. Yeah. So, yeah, it's possible. But it's a very, very high bar when you've had the good fortune that I've had. I can be really selective. So yeah, it's possible that I have another chapter as an operator. But you're not afraid of the work. No, because I'm not retired. I work as you said. I work as long hours today. I travel less, but I work as long hours today across a hundred companies as I did when I was working on one company. Yeah. That makes sense. And then when you think about if you were to ever do one, and again, we're living in like hypothetical law law land here, like I could come back to your crib in ten years and you're still at HQ right here and still advising companies, but you're an entrepreneur. Do you not want to do the zero to one? I feel like I am doing the zero to one. I'm just doing it as a co-founder. So what I'm mostly doing today is I'm running my own startup studio. Yeah. And I've founded five companies in the last four years that I'm chair and founder of. So I am very much doing the zero to one, but I like the role that I'm in whereby I'll spend a couple hours on a startup frequently. It was my idea. Sometimes it's my co-founder's idea and I'll give it a ton of advice and then I can step back for two or three days while my co-founder and CEO goes and executes. And meanwhile, I'm off to the next one. So I'm coaching on five different fields. Sometimes there's slightly different sports and each game is a slightly different stage. Some are in the zero to one stage, some are kind of, you know, in the second or third quarter and later stage. I get to experience and enjoy the thrill of the zero to one stage, but I don't have to be quite as in the muck as a true 100% CEO founder. Totally. What struck me when I was preparing for this is there's a lot of podcasts and videos of you and each one of them has a different title for what you are or who you are. Okay. In some cases, it's the.LA co-founder. In some cases, it's the 75 in Sonny co-founder, which is your venture studio in LA. In some cases, it's the Picasso co-founder, which is your second home sharing company. In some cases, it's the Zillow founder. And in some cases, it's the hot wire founder. Yeah. And sometimes it's the Harvard professor, which is another person. That's right. I mean, I like to, somebody described me the other day as I'm the forest gump of technology. I wasn't quite sure what to make of that, but it's not wrong. So I'll tell you, like, some of the people that I am most inspired by, not necessarily just in business, are those that have the ability to reinvent themselves. I'll give you a really weird example. I think Shaq is the man. Shaq went from this unbelievable basketball player to an incredible investor to, he was shit on TNT when he first started, to now an incredible TNT announcer to a DJ. Like he has this ability to continue to reinvent himself, where almost the basketball player is a footnote of what his career could be. That's how I thought about you when everyone has all these different titles for it. I think it's pretty cool. Yeah. I mean, I'm not -- I do like -- Does that make sense? Yeah, and I'm embracing it. I'm not dead yet. I'm not done yet. have more to do and more to give. I'm at a high level, if you kind of take it up to 10,000 feet, I'm in the coaching mentoring stage where I'm trying to help others achieve their full success. But as I say, I'm doing that across a couple different fields simultaneously, fields in the metaphorical sense, like athletics, but also fields in the professional sense of like different industries. And it's rewarding. The context switching can be hard, but it's an exciting chapter to be in. Yeah, for sure. It's inspiring. It really does inspire me because I aspire to do that. I think it's really cool that there is a potential world where people may not even remember you for Zillow. And that's like pretty amazing because everybody knows that company. That would be amazing. If I'm fortunate enough to be half as successful in any of the things I'm doing now as what Zillow was, and I could be known as in some other way, that would be cool. Isn't it interesting because it's kind of what your father did? Yes. So my dad was an entrepreneur, was an accountant, turned entrepreneur, and he also had several chapters in his career. And I studied that closely and was at his knee and at his hip and at his shoulder during all of that. So just to tell listeners quickly, my father's entrepreneurial journey, he started out as an accountant. He was a partner at a big aid accounting firm. And in the late 60s or early 70s through complete randomness, he was in the restroom at his New York accounting firm. And standing next to him was a British guy who was grumbling. I'm so mad at this stupid accounting firm blah, blah, blah. My dad said, what's the problem? And he says, yeah, your fancy white shoe accounting firm won't take on my client as an accounting client. And because you're too good for us and my dad said, well, who's your client? And he said, the Rolling Stones. And my dad ended up taking a leave of absence from the firm to be the tour accountant on what I think was the 1972 European Stones tour. And that started a 40 something year career in music, where he became a tour producer and business manager for the Rolling Stones, you too, David Bowie, Paul Simon Pink Floyd, the police, Shakira, 38 Special, Leonard Skinner, and on and on. And then music changed so much over those 40 years, you know, not just the format, which went obviously from records to eight tracks to cassettes to CDs to streaming, but also the touring industry changed radically through the next couple decades. And musical tastes changed also radically. And my dad was able to change his business model and reinvent himself and his firm through several different iterations as technological changes occurred in music and tastes changed and society changed. And a lot of the innovations that we experienced today as concert goers came from him and his team, things like resonances, which we take for granted now, where you've got the YouTube residency in Las Vegas, or the different people's resonances at different places. He helped pioneer that with Simon and Garfunkel, that was one of his clients, or 360 touring, where companies like Live Nation buy tours outright, and they spend hundreds of million dollars to basically buy a tour. And they make the tour be like a movie where the actors and actresses in movies are basically the work for the producers. And that's the way touring really works today, where a 360 touring company buys the tour and then the talent essentially acts for the producers. He helped pioneer that with the Rolling Stones and I could go on and on, but I watched all of that. And those many chapters of his career, including just briefly the final chapter of his career, which was focused on electronic music, where he helped roll up and try to professionalize the EDM industry, the electronic dance music industry, in the 2010s, very much like he helped professionalize the rock and roll industry in the 80s and 90s. Yes, those many chapters of his career in a very different industry from tech were inspiring to me and formative for me. It's pretty badass. And he was a good accountant. He wasn't like a shitty accountant that was desperate to get out of that place. No, he was the youngest partner ever in the history of his firm. He was a good accountant. You know, the interesting thing about him was actually wasn't that passionate about music. He viewed the talents. He viewed these bands as product, maybe like the way I view engineers at software companies. They're the ones that create the product and they're brilliant in their own way, but I'm not an engineer. I'm not a, I don't write code and my dad never played any music. But he had other business skills that helped those who created product, in this case, music and entertainment, create great businesses through his intellect. And so growing up, well, one of the questions that I generally ask is what conversation was like at the dinner table. Were you in hotel rooms? Yes, I was at like a lot of summers we toured. So we toured with the Rolling Stones or U2, or sometimes David Bowie, but yeah, usually the Stones or U2 most summers, or many summers. And what was that like? I would go to, you would be in Europe and I'd go to museums with my mom during the day while my dad was at the venue and then at night we'd go to the concert. And then the next day we'd go to a different city and my mom and I would go to other different museums and castles and, and then in the evening night we'd go see a different concert. How old were you? 6, 7, 8 through 15. And this was you, your mom? My brother some years, yeah. Okay, that's insane. And then how do you live a normal life like that? Like how do you like keep in touch with like these people? You as a kid. Don't do what the resume says. Well, because you have to understand my dad was a business person. He was basically the CEO of the company. Sure. That was the tour. And so he he's not partying with, you know, he's not doing drugs and drinking and staying out all night with the band and they're and they're all just like, how good it was. Like, yeah. Well, so okay, so I mean this gets to the title of your podcast, right? Yeah. Great. And how do you teach grit to kids? And this is something that my wife and I talk a lot about because we have three kids and my kids are growing up affluent. I grew up affluent and I somehow found grit and my siblings somehow found grit. And I hope my kids find grit. They're off to a good start. But one of the ways that you do that is you teach kids that despite their good fortune, they're not entitled to anything and that they're going to have to earn it themselves. And my parents always made that very clear to my siblings and me that we were going to have to make it on our own despite whatever advantages were gifted to us through education and through our upbringing. Can I ask what's the expectation with your kids that they achieve their full potential, whatever that might be? So, you know, if that's academic, if it's athletic, if it's social, they have to perform and excel and achieve their full potential. And if that potential is straight A is great. If there's a class that they don't have the potential to get an A in because it's beyond them, then that's fine too. But it's that they have to treat others as they would want to be treated and they have to achieve their potential. And did you and your brother growing up, like, was there an implicit assumption as there generally is of like, we'll just take the family business? No. On the contrary, there was always a very clear communication that we would not receive any inheritance, any financial advantage. We talked about this a lot as a family that my parents said, they will pay for our education, we'll graduate from whatever the best colleges that we're able to get into debt free. And I'm grateful for that. And that's it. There'll be not one penny given. I can never want to graduate school. So, I guess, I never tested that. What happens if I want to go to graduate school? I'm sure they would have paid for that too. But the answer is your education will be taken care of and then you're on your own. And to this day, I'm now in my late 40s, I've never received a penny from my parents, you know, other than the tuition that they paid for me. And so I won't inherit the family business. I won't inherit any money. It's you're on your own. And my wife and I tell the same thing to our kids as well. And that's a strategy. You know, I mean, there are different families have different approaches to this question. That's the approach that my parents took and they approach that my wife and her taking with our kids. You're doing the same. We are. And then you go to Harvard. Was the transition from that life to going to school, leaving the nest abrupt? No, no. I mean, my high school in L.A. was a really competitive, academic, challenging high school. And I felt like my college experience was just a continuation of that. So I felt very well prepared. And I also had traveled extensively and lived away from home and also traveled with my parents. So I was well prepared for the college experience. Can I ask about your brother? Sure. You mind? No. What happened? Sure. In high school. Yeah, I was 15 and my brother was 17 or 18. And it was the week of his high school graduation. And he died in a car accident just a straight up accident. No drugs or alcohol or anything like that. And he was going to Princeton and it was two days before his graduation from high school. And he was my only sibling at the time. And that was obviously heartbreaking for me and for my parents. We were all very, very close. And about a year later, my parents decided to have more kids. And so my brother and sister, same parents, same marriage and all that, are now about 18 years younger than I am. So I have a much, much younger brother and sister there in the early 30s. And they were born out of the grief of my brother's passing. I'd actually sort of side note, my sister has gone into my dad's industry and has charting her own path in music. She was at YouTube in Spotify and now she's in a music management company. Now she's at Riot Games and helping Riot with their music strategy inside and outside of gaming. And so she's following in his path. And my brother said a totally different path working on the Capitol Hill and now in environmental policy. You know, the impact on me of my older brothers passing was intense and profound. I think as it relates to this conversation about professional achievements and all that, for me, it was a kick in the butt to go and kick ass. And that definitely added and created grit for me. It was, how do I go and achieve double go whatever he was going to go to in the achievement and like everything I'm going to go basically beat this pain through achievement. Yes. And try to achieve whatever I was capable of achieving and also whatever he was going to go off and achieve after he, whatever life he was going to go live, I was like, shit, okay, I guess I got to go do double and that drove me, probably still drives me a little bit, but it drove me a lot for the first couple of decades. It's been almost a couple of decades. It's been, I guess it's been 30 something years now. And maybe relating it back to teaching your kids grit, that feeling, you can't teach that feeling. Well, you can model it. I'm not sure you can teach it, maybe that's a distinction without a difference, but like my wife is a doctor and my kids have seen my older daughter saw her go through med school and just how challenging that was and residency and fellowship and the younger kids have seen just how hard she works in medicine and how hard I work. So I'm not sure we're, you know, you don't teach grit, you just model grit. And so yeah, my kids have learned it through that. Yeah. Thank you for sharing that. When you were trying to compensate through achievement, was that always going to be the mechanism with which you channeled your pain? That is the almost healthiest way to push that grief kind of out into the world. I don't know. Um, I'm not sure how it's to ask that. Probably. Um, well, I don't, I've never like studied this or read books or thought that much about the different ways to demonstrate grief. I suppose you could let it all out and be really emotive. You can probably tell that's not me. You can keep it all in and not be not where it on your sleeve. You could that probably describes me more. Yeah, I don't know. I'm not sure how else. I guess that another way some people deal with grief is by sort of spiraling on their own, their drugs and alcohol and just kind of like moping and feeling a victim. That's not me. My parents decided to channel their grief by having more kids. And the research says that usually or frequently when parents lose a kid, they get divorced. Like it causes such marital pressure and strife that, um, you know, they don't stick together. My parents fortunately chose the opposite extreme. They decided to double down and have more kids. Um, you know, and I'm glad they did and that kept them happy and together for a couple decades more. You graduate a couple years later, you go to Harvard, then, um, you end up at, I just had this flash to the Jeremy McGuire scene when the Roy Firestone interview came at the end. It's like, you're not going to make me cry. You're not going to make me cry. Great. Great. Great. I just make a smooth transition. Okay, yes, I graduate. And it's, so like, it still sticks with you like this. Yes. Yes. Yes. This thing just keeps driving you there. Like it, it keeps you there. Again, I go back to like, you know, beautiful home, like you have all these things, but like, you can't be more busy right now. And that, this isn't by accident. This is just, there's something in you that burns these logs and I suspect it's this feeling that you had when you were 15 years old, that lives right there. Because you can't manufacture people that work this way. You still push yourself. And by the way, you're like the founder of four companies right now, five companies. You don't have to do that. Right. You know, yes, you're right. It is common among people like that to have been kicked in the nuts somewhere, somewhere in their life, the loss of a parent or the loss of a sibling or, you know, some, some huge adversity or trauma that they had to overcome. And, you know, obviously, I wish my brother hadn't died, but it also helped make me who I am. Yeah. For sure. Are your parents still together? My dad passed away a couple of years ago, but they were married for almost 50 years. Incredible. When I was reading about you, I couldn't believe that you were at a private equity shop that rolled up a bunch of different airlines and tell me if this is an incorrect story. And at 23, 24, they were like, all right, go spin this thing out, which eventually became hot wire. Like, that's in fucking, that is insane. Well, yeah, I mean, I spent two years at Goldman Sachs after college and I'm glad I did. I learned a lot. Investment banking was formative for me, but I wanted to be closer to the operations of a business. And investment banking is all about the deal. And I felt like I was always listening to a joke and I never heard the punch line like I would advise on M&A and we talk about all the synergies that buying some division or emerging two companies together would create. But then we were never there three years later when it came to fruition or not. And so I moved to San Francisco in 1999 to work at TPG, this private equity firm. And TPG, as you point out, had bought or had rolled up a couple airlines. They bought America West out of bankruptcy. They bought continental airlines out of bankruptcy. They had sold much of their continents to Northwest, so they controlled a lot of Northwest airlines. They bought Ryan Air in the UK and Europe, which was sort of the Southwest Airlines was the largest carrier in Europe. In 1999, a lot of the private equity firms, including TPG, were trying to figure out how to play the internet. The internet was pretty new. There was this huge boom. All these companies were going public all over the place. And frankly, the captains of private equity were no longer the captains. It was all of a sudden it was now John Doerr, a client of Perkins, not David Bonnerman at TPG that had all the attention and headlines. What some private equity firms try to do is leverage their portfolio companies into the internet. And TPG strategy was to put a couple of these airlines, or bring a couple of these airlines together and create a consortium company in the discount travel space. And I got staffed on this. This was not my idea. I got staffed on it as a, or a young associate. And I got named Carl Peterson, who was a couple years ahead of me at TPG. He got staffed on it with me. And David Bonnerman, the founder of TPG, was his idea and he was the chairman and basically the founder. And we spent about six months riding the business plan, getting these six airlines together, bringing the seed funding, the seed round was a $75 million seed check from TPG, which was a pretty big seed check, hang. And that's like 20 to 21 vibes. Exactly, exactly. So it was, it was a huge round. And then we kind of all looked at each other and said, you know, maybe we can do this. And so Carl and I went to Bonnerman and to TPG and said, hey, we want to leave the firm and go run the company. And very fortunately, TPG led us. So Carl became the CEO. I became, I think my, I think originally I was COO or maybe a CFO, I think eventually I kind of settled on a VP corp and co founder and co founder, yes. And we brought on two other very early folks who became co founders with us, a guy named Greg Brockway, who went on to found Tripit later and then Cherish and a bunch of other startups. So he was our third co founder and then a fourth co founder was Eric Groza, Eric went on to become president of Expedia and then now he's running in Sparato, KP company. I keep it. Oh, I didn't know that. Yeah. So yeah, that was 1999 when we started Hotwire and the first couple of years were great. The company was growing up to about 200 employees, things were going really well. And then 9/11 happened. And September 11th, 2001 was a tragedy, obviously, for the country and the world, 3,000 Americans died. Four planes were hijacked and Hotwire had sold tickets to the hijackers. And we sold not the September 11 flights, but the September 10th flight from Bangor main to Boston Logan that put the Boston cell in position. And the company didn't know that at the time. Well, the company still didn't know it. Just to clarify, the senior team, Carl and I, and I think Eric and Greg found out about it that afternoon when the FBI contacted us and said, what do you know about these customers of yours and who bought tickets from you? So I just mentioned that detail, which is something I only started sharing a year or two ago after 20 years had passed. I thought it was safe to start sharing that detail. To give you a sense of just how palpable our sense of guilt and our eerie connection to this tragedy was, from a business standpoint, it was terrible. We had tens of thousands of customers stranded around the world, who flights were grounded for, I think, it was 12 days. Everyone was afraid to travel. So they were very. Forget about that. Yeah. I mean, there was basically no travel for six months because people were afraid to get on planes. And then there were a couple of wars started in Afghanistan and then Iraq, you know, after this. It was a pretty hard time to be running a travel company. We did our layoff. We went from 200 employees to about 150. I remember as a 25-year-old having to lay people off as a first-time manager and that was intense and traumatic and I was on charter territory for me. And we did our down-round, which at the time I didn't. I don't think I really understood fully the implications of a down-round, but we didn't have much choice. So we kind of had to get it down. I think we raised a $20 million down-round from TPG, who basically bailed out the company. My two years later, by 2003, so two years after 9/11, four years after founding, the company was doing well again. And we hired Goldman Sachs, where I had worked and where my co-founder Carl had worked, to take us public. And we were on an IPO. trajectory at that point, which was amazing that we had somehow managed through the downturn after 9/11, and then Expedia medicine offer and Expedia ended up buying the company from a 700 million, which was a great exit considering just how low the company was after 9/11 just years earlier. Why'd you wait so long to talk about it? The 9/11 detail. We never told the company at the time. Oh wow. It was sorry, yeah, just to clarify, it was only something that three or four of the top people knew our general counsel, Kathleen Phillips, I'm sure she knew and one or two other people. I don't know. It felt almost exploitative also to share. Yeah. Did you feel guilt? Yes, absolutely. Yes, I did. I've never talked with my co-founders about whether they felt guilt, but yes, I felt guilt. Like obviously, we were selling tens of thousands of airlines tickets today. We couldn't certainly know who our customers were, but it's probably a little bit like the Israel tragedy that we're witnessing right now, where if you have friends in Israel, because it's such a small country, everyone there has one degree of separation away from one of the thousand or so people that were murdered or the couple hundred people that were kidnapped on October 7th. If you have a truly personal connection to something, it like I felt we did through hardware 9/11, it just becomes even more palpable and traumatic. I mean, I also, I guess I had two other personal connections to it. I had, first of all, a family friend was on one of the flights that died, and I knew her very well. She was one of my parents' closest friends. And then I was on the flight on September 10th, the Newark to SFO, the same exact flight number. I think it was Flight 77, the one that was ended up in Shanksville, Pennsylvania, that heroically was, you know, the hijackers were wrestled to the ground by the passengers. And then that plane, I think, was headed to the White House or the Capitol. I think we're still not sure where it was going. But anyway, I was on that flight a day before. And I had spoken at the Millennium Hilton in New York on September 9th. I gave a speech at a hotel conference there. And the Millennium Hilton was demolished on September 11th, you know, when the Twin Towers fell on the Millennium Hilton in the World Trade Center. So I also had this personal connection was saved by 24 hours. I mean, if the conference had been on September 10th and I flight home in September 11th, I would have, I obviously would have died. So I felt that personal connection, the company felt the personal connection. I don't know, it just felt sort of exploitative to, yeah, that makes sense. To share all this until, until recently, did it fuel you again? Or did this one paralyze you a little bit? It was pretty similar to my brother's death, I guess, paralyzed for a couple of hours and then sort of spring into action. I mean, I remember that day on September 11th, it was also the day that my wife moved from San Francisco to med school. So she was moving into med school in Seattle. I was in San Francisco in my apartment, in our apartment, watching the news. And San Francisco was shut down. There were threats all over the place. You weren't able to leave your apartment, nobody was in offices downtown. But by that afternoon, we had to do something. We had thousands of customers, tens of thousands of customers that were all over the world and wanted to know what the hell hot wire there travel agency was going to do about it. So we had a couple of hours of trauma, grief and paralyzation and then by that afternoon, we were building out phone trees. I mean, there was no internet, there was no slack, there was no, I don't think there was even texting. I mean, obviously there was internet because how I was an internet company. But just to give you a sense, we were building out phone trees to call employees and tell them, like, don't go to the office and it was, you know, and then by that afternoon and by that evening, we were trying to figure out the big question, and there's actually a Harvard Business School case study on this question, is what do we do about refunds? We had tens of millions of dollars that customers had bought tickets and hotel rooms for the next couple of weeks and they wanted their money back. But we sold a non-refundable product. And the airlines and hotels weren't going to give us the money back. And the credit card processor wanted a line of credit for us to keep being able to process credit cards because they thought we were probably going to go out of business and they were right. And so the HBS case study is about exactly this. It's, oh shit, what do we do? Do you do the refund? Yeah. And that's just a small part of it. It's like, in general, what the hell do you do when you're running a company? And by the way, this isn't abstract. What do you do when you're running a company and all of a sudden a pandemic happens and all of a sudden, you know, your employees can't go to work and your customers will ask you about your money back? Yeah, our SVBs. That's better. Right. So like, you know, these so-called black swans, they happen more often than you think. So it's a very good case study that they wrote about it and I teach it at HBS now. It's bad. Is you refunded in the first person? And yes, we refunded and we renegotiated with the credit card processor and we did our down-round and we did our layoff and we sort of somehow pulled a rabbit out of the hat, but it was hard. In these situations, isn't the right answer pretty much always to make your customer whole? If you can afford it, but it's like, well, what if you have, I don't remember the details of the case, but you know, if you have nine months of cash left and refunding, it takes you down to three months. Yeah. Yeah. What do you do? Yeah. Again, like a lot of companies were dealing with very similar stuff through the last couple years of challenges. Yeah. When TPG came in, did they wipe out the cap table? Yes. So they recapitalized the whole company. They recap the company again. And you were 25. Yeah, and you had no idea. Advice I give to founders is all that stuff that you hear, lick preff and ratchet and preferred and common all these words that you kind of fake your way through. And you sort of know what a safe with cap is, like go learn it or get a lawyer that knows it well or figure out how to talk to chat GPT about it because it's important stuff. Like all of that stuff is about what happens when things go sideways or go south. And you don't think early on that any of that's going to happen, but it might and it's lessons learned the hard way. Now again, we didn't have much choice at the time. It was kind of a take or leave it type situation. And I'm very, very fortunate, we're very fortunate that TPG build out the company the way it did and that we had a great exit, which returned a lot of capital to the preferred shareholders and a little bit of capital to the common equity. But downrouts can be punitive and there are a lot of companies going through them right now. Yeah, this great euphemism of quote, unquote structure, which founders are hearing all the time and VCs are saying all the time, oh, that round has structure, that round has structure. Like, well, okay, figure out what that really means. Make sure that you understand it as well as the investors. So you didn't, you didn't make as much as everyone in the outside. I made a, I made a million bucks. I think I've shared that. I'll share it again. We sold the company for six hundred eighty five million, which was the highest, I was a co-founder. It was the highest ever cash sale of an internet company to up to that date of time in 2003. And I made a million dollars and I bought a house in Seattle about my first house. I bought a seven hundred thousand dollar house for whatever five hundred thousand down I think and I put three hundred and fifty thousand dollars into my next startup, which was Zillow and that three hundred fifty thousand dollars would make up for that would work out of misgivings. Yes. Were you like, what the fuck? There's all these headlines about biggest cash acquisition in a tech company. You're the co-founder, you're young, like everyone thinks you're the man, but you're like, wait a second. I just did all this work. Yeah. Somehow I didn't come out. It's fine. I just watched a documentary about Jewel, the vaping company. It's called Big Vape on Netflix and this was one of the big things that their employees focused on that all their friends and family were like, oh, you know, you must have made so much money, so much money and they made very, very little money and just how that dissonance was really stressful for them. So yeah, I mean, look, but I have no complaints and no regrets. I was 27. I had an incredible exit. I learned more in those four years than I ever possibly would have learned in business school or doing anything else. I made incredible relationships and friends that last to this day and that experience enabled me to do everything that I've done since then. So I have a really positive outlook on it, even though I didn't make as much money as I would have liked. And you rolled the rest of that money, the 350 into Expedia instead of raising money? Sorry. Yeah. So what happened was we sold HotWire on my honeymoon in 2003 or your wife must have loved. So I was like calling in from my honeymoon and, you know, to call my co-founder like the deal close. The deal close. And so anyway, we closed the deal, we got back and then I immediately moved to Seattle because that's where my wife had moved from San Francisco to Seattle. And so I worked at Expedia, the new parent company of HotWire. And I was at Expedia for about a year and I had the entrepreneurial bug again. I wanted to do a startup. I wasn't that happy at a big company that I thought wasn't moving fast enough. And so when I left Expedia, I joined up with two other early folks from Expedia and we started Zillow and we raised, I'm trying to remember here, I think we raised six million in that pre-seed round. I put in 350, one of my co-founders did 2.5 million, the other did 2.5 million. And then the other couple early employees did the other 600 something thousand bucks. And so that was the first six million dollar pre-seed that we did just from the employees to start selling. Wow. You don't see that very often anymore. No. And then the series A was benchmark in TCV and that was I think a twenty-five million dollar series A. But you're happy you guys did it on your own now. Yeah, for sure. And I mean, that bootstrap round, which is basically, that's basically the model I'm following now when I'm starting new companies that can make a lot of the difference in the returns. And it was a bet on ourselves. And by the way, we had no idea what we were doing at the time. It was like, let's start something in real estate, digital real estate. And we had no idea. And I'm happy to get into detail in that if you want. And even after Hotwire, you still felt unequipped as a founder in the. travel, be the sea space? Yes, I was still learning a lot about startups and at 27, yes, I had had the hot wire experience and then just a short-stinted expedient, but I was still a 27-year-old co-founder. My first role was COO and then CMO and then I was CFO for a while at Zillow and then when we did the series A, I became CEO and so I was a first-time CEO. I was still only 27 and it was a brand-new industry and it was, yeah, I guess I feel like I'm still learning but it was really still learning back then. At the series A, when you became the CEO, was Zillow still just basically the zestimate? Yes, we raised the series A if I remember correctly, pre-launched. Nobody knows that. Yeah, it is kind of surprising to me. I sort of take that for granted. We launched in 2006. Let me back up, actually. We knew we wanted to start a company and we weren't sure what we were gonna do and we spent about three months in a conference room trying to figure out what to do. And like most great startup ideas, we started solving problems that we were having ourselves and we were editing family photos on hard drives. It was one of the things that we were all doing because we had all been working so hard for the last 10 or so years and we had all these digital photos that were taken on digital cameras. Remember, there are no smartphones yet. And all of those photos were on these hard drives and we were editing them and we're like, "Oh, there's something here around file swapping, file sharing." And basically, behind door A, startup idea letter A was Dropbox. And Dropbox didn't exist. The cloud didn't exist. There was no box, no Dropbox, no Azure, no AWS. And so the first idea was let's do a file sharing, file swapping storage thing. And the other thing we were doing is we were all buying homes. As I mentioned, I bought my first home at that point with my hot wire money. And so I was shopping for a home and my two co-founders were shopping for homes. And so we were building mashups of King County, which is the county in Seattle, King County website data, Google Maps data, MLS data kind of piecing together what would a home shopping experience look like for us personally. And so those are the two startup ideas that we had when we weren't sure what to do. We decided not to do the file sharing thing because we thought cloud would be a race to the bottom on price. We thought that eventually the internet giants would give cloud storage cloud services away for free to get you into their ecosystem. Now we never predicted it would be Amazon. - Relatively prudent. - Super prudent. We were totally right strategically, but totally wrong about who it was. We never thought it would be Amazon. They sold books and DVDs at the time. We never thought it would be Google. They were search engine at the time. We never thought it would be Microsoft. They sold Outlook and Office at the time. We thought it would be like Yahoo or eBay or PayPal or whatever. So that's why we didn't do that idea. And we did decide to do the real estate idea. And so then we were like, okay, let's build a real estate website. How do we get traffic? And the idea was we observed that every real estate site answered one question, which was what's for sale. And we said, well, that's kind of interesting, but the more it's the question is what's your home worth? And so we spent the next six months building models to try to value as many homes as we could. When we launched in February of 2006, we had zest mitts on 40 million homes. So a price on about half the rooftops in America and publicly available data, bed, bath, square footage, and prior sale data. And that was it. No listings, nothing for sale, no rentals, no reviews of real estate agents, no lending, no mortgage, no anything else. And we got about a million visitors on the first day. We got about four million visitors in the first month. I think even to this day, that's faster than anything. It was faster than Snap or Instagram. It was faster than ChatGPT. And I don't think they had a million users on the first day. So it was on. Yeah, I mean, there was huge traffic because of the voyeurism of, oh, I can zillow my ex-girlfriend's house or my boss's house or see what my parents' house is worth. And so we had huge traffic initially. But then it took about two years to get back to that same traffic level. So this huge burst of traffic, everyone checked his estimate and then everyone went away. And then we had to grind and find grit. And by two years later, we find ourselves in 2008 during the financial crisis. And at that point, we went to brokerages and said, hey, give us your listings. Put listings on our website. We were at top five website at the time. Top five real estate website. We had 10 million visitors. And we said, put your listings, it's free. And at that point, we added listings. Only once zillow is a couple of years old. How often are founders that are in your portfolio looking for their version of his estimate? Okay, every day. Gosh, I hear that all the time. I hear that all the time. I bet. Yeah. And like, how do you, can you like get a good, I usually say, I wish I knew. You know, I mean, we do our best. Like, you know, Q, which is a startup right now, has a startup that a founder of, which is a streaming discovery service. It has a pretty viral feature, kind of a swipe left swipe right on movie and TV titles. And we hope that becomes its estimate because it has a lot of K factor and a lot of virality built in where it's like a fun game and it helps it ties directly to the product the same way the Zestimate ties directly to the home shopping. But yeah, I hear it all the time from founders if, you know, hey, how do I come up with this estimate? You run or ran, is this podcast that you were running when you interviewed, like, Cheryl and Satya and that, is that still like, it's still around? It's called Office Hours. We've done about a hundred episodes. Oh, yes. But it's not like you're not pumping him a week. I'm on a hiatus right now. So I started Zillow almost 10 years ago. And yes, I've had, you know, Satya Nadella and Charles Sandberg and lots of great guests. And then when I left Zillow, I took the podcast over and it's produced by.LA now, which is my company that covers the LA tech ecosystem. And so, yes, it's Office Hours is still very much alive. It's just, I'm not doing episodes right now. I'll probably start up again in Q1. - Okay. The reason I ask is because you do these podcasts, you get to meet all these successful people, right? You now are a Spencer. You get to meet successful people because of just what you've done, right? You invest in a lot of companies. So you have to say, you see all these things, right? Do you ever have this thing where, again, going back to my Zestimate question and people ask you, people ask me about this podcast all the time, I'm 160 episodes in. We've had all of these incredible guests do it weekly and they always ask me for patterns. Always, like what are the common threads? And I get really frustrated 'cause I've spent enormous amounts of time trying to pull common threads amongst all of these journeys, rides, companies, entrepreneurs, and it's really hard. Because in my experience, I have found, it's hard to tell someone why Zestimate worked. It just worked, you know? And the reason the show is called great is because I'm quite convinced that that is definitely the one thing that has to be there. The only other thing that I have pretty consistently and surprisingly found is a really strong partner at home, husband or wife. And like what I really wanna be able to say is, oh, they hired this person and this profile early. They had a problem that they felt in their own life. Like all the canonical and conventional wisdom, I find it very difficult to wrap it neatly in a way that I would argue most venture capitalists do and then spit that advice back out to other entrepreneurs. Do you have an easy time drawing through lines between all of these success cases that you've had the opportunity to study? - I would add two through lines that I've seen consistently. One is the founder product fit, so personal connection from the founder to the problem. And the second is their ability to recruit, retain and motivate teams of people. That's probably the most important thing is one's ability to grow a team and attract great people, especially the first couple dozen people that then build the early product and create the culture for the company. - Yeah, the problem is there's, actually on the recruiting and retaining talent, I can't think of many counter-examples, but on the founder product fit as an example. How do you reconcile when companies pivot? - Meaning with your steward from Slack. - Yeah, that's an example I was thinking of, who has been on my podcast also, talking about that topic. I mean, I think that founder product fit can grow. You know, I'm not sure he grew up, his whole childhood, saying God, I really wanna build workplace productivity software. But, yeah, and I know he started a gaming company that failed and then pivoted to the Slack product. But I think he learned and developed that founder product fit to the workplace productivity product. I mean, I also, I'm not sure I grew up my whole childhood thinking about how can I help people by discount travel products. But I love travel and I believe in the mission of Hotwire and kind of got on board, you know, as we, again, as I mentioned, I was staffed on that. It was not my idea. - Yeah. - I was just, yeah, yeah, I could've been some other associate that TPG grabbed and threw into that and I could've worked on some other LBO instead. - Yeah. - But I developed that founder product fit. - Yeah, it's almost like there's this greatness there and that you happen to stumble on this greatness and apply it toward a specific problem. In your case, it happens to be in the B to C space that's continued over time. In your dad's case, he didn't know anything about music. - The conventional wisdom that everybody tells me is that the people that are most successful, and by the way, I believe there's an overwhelming amount of examples to your case. Like Brian Chesky at Airbnb, the list goes on of folks that have felt a problem and then felt like there's nobody else to solve this and if I don't do it, nobody else is going to. - I'll give you two quick stories on this. - So I remember when I first met Garrett, my co-founder, at CU, I asked him this question. I said, "What would happen if I told you you couldn't do this startup?" You're not allowed to, you can't work on it. And he just looked at me like I don't know what to tell you like I was put on earth to solve this problem I wake up every morning trying to figure out how can people do a better job of figuring out what to watch and I go to sleep every night Obsessing about that like that's all I care about and I was like, okay, you clearly have a positive signal And then another friend of mine started a company that had a good I think a hundred plus million dollar exit That was a B2B SaaS company for Scheduling of fast food workers shifts. So it was like an enterprise software company that would tell a fast food worker Went to show up at work and I was like wow that's boring like who cares It was kind of what I said to him. He's like no, no, you don't understand Spencer. This is the greatest thing ever This is so on mission imagine your single parents and you're trying to figure out like how to get the kid to the bus And how to deal with this and care for their sick grandparents and you know, and like your ability to use this software Changes lives it changes their ability to have more time and control and the passion with which he was talking about this software that I found so boring Yeah, it was so clear that he had a founder connectivity to this problem and maybe he's faking it or maybe he gained it over time I'm not sure but he had passion for that in a way that I certainly don't if you asked me to go around that company Even though I'm a good founder and a good tech exec. I'm not sure I'd be great at it. He was great at it So that example always comes to mind when I think about this issue of founder product fit I am definitely taking the not like the contrarian point of view on this one like all of my colleagues would agree with you Everybody in the venture community agrees with you even you brought out Travis earlier to start up before Uber for Travis was nothing to do with ride sharing And maybe like if I were to again now we're just like I'm just riffing with you because I think about this a lot And if you were to maybe like layer it up one there needs to be an obsession and the reason there needs to be an obsession Is because you cannot be gritty unless you have an obsession. So again if I go back to my point And maybe I'm just trying to fit my own narrative here of grit is definitely the thing Great is the ability to overcome hard things if you're not obsessed about the problem that you're solving You're gonna give up easier than others are going to now obsession in its most obvious form is someone that felt a Problem that they need to go solve but obsession I think can also be cultivated over time by diving into a problem Realizing the opportunity of that problem then realizing that there might be a really big company that you can go Build that creates a bunch of enterprise value that solves a problem for a bunch of customers that hires thousands of people that you can go make rich Whatever it is right. I think sometimes the founder product fit is a little more abstract I'm not sure Travis initially was obsessed with disrupting the taxi industry I think he was obsessed with trying to make people feel like ballers and Press a button and have a black town car arrive and make you feel like the shit I mean we're now putting a founder on the psychotherapy couch that you know He's not even someone that I know well, but I guess then over time one can Build a connectivity to the problem that they're solving so like I feel totally connected to the Picasso mission Second home ownership is something really important to me. I think it can lead I think it can change lives I am personally connected to that mission, but I think sometimes it's like a hop or a skip away from It's not necessarily about doing something in the industry. Maybe it's about trying to help people feel a certain way Yeah, I completely agree. Anyway, like probably we're not going to solve this here And if we did we'd be like the greatest investors of all time the Picasso thing is super interesting to me because it is such an obviously good idea and I think the product is pretty good. How do you balance this thing where it's almost the worst if there is an obvious idea with a great problem that nobody knows about or that you can't bring to market Do you think about those two? I think about a lot my co-founder Austin and I talk about this a lot where I mean what I usually say is I think that the idea for Picasso has one of the highest net promoter scores as an idea like when you just hear the idea Like which is go ahead what is it? Okay? It lets you buy a portion of a second home So you buy a quarter or an a three hits of a second home and you co on that second home with other folks that you don't know and Picasso does the Property management for it. So it lets you supercharge your buying power if you're thinking about owning a second home and you right-size your Ownership because you're not going to use that second home all the time anyway, so it's sort of like carpooling for second homes and Then you start doing the math and you're like holy cow. Maybe I could have a Quarter of a four million dollar home that would be on the beach instead of buying all of a second home That's kind of crappy. It makes a ton of sense and the house wouldn't be wasted and just sit there empty all the time The hard part is the operational complexity like ideas are easy execution is hard and Picasso is a very complicated business to operate It is not just digital. It's not just bits. There are a lot of atoms Scheduling is complicated mortgage finance is complicated property management is complicated Navigating the real estate industry is complicated people psychology of how they own homes is complicated Absolutely, and it's also an expensive discretionary purchase, which means people can always come up with a reason to put it off And so it has potentially to be pretty cyclical based on people's perception of their net worth We have to fight that because actually we think it should be counter-cyclical because people should trade down from buying a whole second home To only buying a Picasso or you know an eighth or a quarter per second home when they're feeling strapped But that's a bit of a mind shift also, so yeah, it's hard to pull off now like many of the best ideas Like Airbnb, for example We didn't invent this concept so Airbnb didn't invent the idea of renting out your spare room or renting out your house Right people were always doing that on a do-it-yourself basis and Picasso didn't invent the idea of a couple people buying a house together People have always bought three families buy a ski house together parents and their kids buy a beach house together like this has always happened But trying to operationalize that and solve some of the challenges with it the reason that that's not a big thing is Because of scheduling of mortgage of resale of governance of the house of furnishings Like those are all deal breakers or things that cause you if you were to do this on your own with a couple of friends It usually doesn't work out and so Picasso's trying to solve all those problems at scale and that's very complicated Yeah, it's super complicated, but very exciting. So we're at series C now We raised about 250 million of equity. We're in 40 markets 250 million. Yep It is capital intensive all it's kept on sense are you guys buying the houses up front not always so ideally We're not buying the houses up front right ideally we put the home under contract to close in say eight weeks And then we pre-aggregate the demand and have it all spoken for and we sell it as soon as we buy it Yeah, it doesn't always work out that way Otherwise you get in a bit of a we work situation Sometimes we sometimes we do own sort of stubs of houses Yeah, which we then have to sell down there whereas like a company like wander is buying all of its properties and then fitting them all out Yes, right. Yes. Yeah, so I mean we just passed a billion of sales in our third year It's amazing. We've got thousands of owners So the product's working really really well, but we got a long way to go still you have some really great Career thoughts that I was hoping to chat with you about the first is this notion of a career mirror Can you talk about that is in my case? It's my wife, but more generally a career mirror is somebody That's in your life. It can be a friend family member. It can be a psychologist a priest It can be anyone in your life that's close enough to you to Hold up a mirror to you But is not like so in the weeds that they are too close to it So every major career decision that I've made in my life from Leaving investment bank to go to private equity from leaving private equity to start hotwire from leaving hot Where to go to expedia from leaving speedy to start zilo and on and on my wife has played a huge role has usually said to me Months before I realized hey, you know you're unhappy. You know you're not learning anymore at that role or you know that you were more Excited back when you were doing this or doing that and so that's a career mirror It's somebody that can help tell you that and that's critical. I think for people that makes sense to me right now Is has she held the mirror up to your face she has and she likes so far what she sees although I will point out that What you were pushing me on earlier in the conversation of you know, do you have one more in you? You sure you don't want to come out of retirement and get back on you know suit up and get back on the field She says that from time to time and And she knows what that means for you and the family she does and she's Okay with the sacrifices that well, otherwise what's the alternative like you drive yourself into misery? You know like you you feel like you left something out on the field. Yes. She would say that She believes that I am very happy with this chapter and I am But she also thinks that there may still be something out there too. Yeah, that makes sense And then the other thing that I love that you talk about is how people can evaluate In their career rather they should stay at a company or in a specific career track can you talk about that? I get this question a lot from people that I'm mentoring or friends of you know, hey Should I leave should I stay et cetera? So my general rubric is do you feel fairly compensated and appreciated at work Are you still learning and having fun and if you're not if those things aren't the case Then it's probably time to leave and the only other thing I'd add is that when you're leaving a big company You can really only do that once you make that leap once and so you have to choose that very strategically I had a call yesterday for example with a pretty senior executive is a friend of mine at a big tech company One of the biggest tech companies in the world and he called me is like I'm just not motivated I'm not excited. I'm not fired up But I make a lot of money and my current role like what should I do? And I'm like well clearly you should leave. I mean, there's no question But you got to choose your spot really carefully because I use this Amazon one-way door two-way door thing Or which is the Amazon rubric for making decisions whenever they're making a decision Amazon They discuss is this a two-way door decision meaning you can go backwards. Yep that door or one-way door decision meaning it's permanent decision leaving a. senior role at a Google, at a Meta, at a Microsoft, or whatever, and Amazon, like that's kind of a one way door decision pretty much because I mean, yeah, I guess you could go back, but it's a little bit hard. So it's just, it's a really high bar for a decision like that. That's kind of the framework that I applied to that question of when is it time to leave or not. - Yeah, and then you have this idea of like, look at your boss or look at your boss's boss, like the people that are senior to you. - Yeah, I wish people did this more. This is something that I learned in investment banking. I always looked at people 10 years or maybe 15 years my senior and said, do I want that life? The whole package, do I want just the job? - Not just the job, do I want their compensation, their title, the respect they have in the community, the type of work they do, the lifestyle, the relationship they have with their friends and family. Do I want that? 'Cause chances are that's what my future holds. And that's one of the reasons I left investment banking. I liked certain aspects of that life, but not all aspects of it. Notably the lifestyle is very, very difficult and to be in a services business. If you're in a services business, whether you're a lawyer, an accountant, an investment banker, you're always at someone's back in call and that can be really hard. So I encourage people to do that. Look at your company or at your career path and look five, 10, 15 years ahead and be really intentional about it. 'Cause otherwise you'll wake up in the blink of an eye and you'll have that guy's job or that guy's job five or 10 years from now and do you want that? - Going back to your one way versus two way door. By the way, I love this concept. Do you feel like people aren't actually good at recognizing one in two way doors? - Let me be specific. My belief is that I think generally people, especially in career decisions, overestimate the idea of risk. I think that in their head, things are much riskier than if they look backwards, what they're perceived risk. Like they didn't calculate that very well. - I totally, totally agree. - And just people think that two way doors are one way doors. - I totally agree. People overstate risk. I just had this conversation with someone yesterday. I 100% agree. People have more of a backstop than they might realize. They typically have some savings. They typically can go get a job. I encounter this a lot with people that have been two or three or four years at Zillow, at Google, at Microsoft, whatever. And they're kind of in their mid to late 20s and they're like, they really want to do a startup and they're trying to side should I go? Should I do it or not? That is a pretty risk-free opportunity for me to leave to go do that. They're not leaving at a super senior level. They can probably go back to some big tech company and rebuild the nest egg if necessary. It's not as risky as they think. Real risk is running into a battle, running into a burning building or a hospital which is overflowing with COVID patients or the battlefield in Ukraine or Gaza. Like that's real risk. Doing a startup is not real risk. - I think really well said. You also have another podcast with your son called Dad, I have a question. That's so cool. Why did you start that? - How old is he? - My son is 15 now. We started this when he was, oh gosh, probably 10 or 11. - Oh, is he becoming too cool for it? - He's becoming too knowledgeable for it. He doesn't have as many questions anymore. It's time to rebrand and say, Luke, I have a question and let him teach me. But yeah, we've done almost a hundred episodes and it started, actually I'll credit my late father-in-law who passed away a couple weeks ago. It was his idea because he would be around the dinner table and Luke would ask me, what's blockchain? What's inflation? What's crypto? How do banks make money? What's the electoral college? And I would answer and my father-in-law said, this would make a great podcast. And so my son and I just started throwing episodes out there. We used my phone and recorded them on anchor, which I guess is now part of Spotify. And we've had, I think tens of thousands, probably hundreds of thousands of listens now. And it's been super fun. I mean, if you can teach a 10 or 12 year old about a topic, then you probably understand it well. And that's a good litmus test for your own knowledge. And so the best episodes are the ones where I'm teaching him something that adults think they know, but not really. Like what's Web 3? How do mortgage rates get set? These things that you kind of think you could sort of fake your way through, but you don't really-- I'm not sure I could explain the electoral college or really have an answer. I don't think I could really get it. I got a lot of adults kind of sheepishly admitting to me. I love that podcast because actually I learned a lot from it. It's good for kids and also for adults. When you do all these things, you've said the word context switching, which struck me even from the beginning right now. When we were setting up, you're going back to email. I have a feeling you're doing a bunch of emails with a bunch of different people, with a bunch of different companies and a bunch of different ideas. You're feeling a bunch of stuff. Do you do anything tactically to organize? I do a couple of sort of obvious things. I use Slack and I've got seven or eight different slacks. So one for 75 in sunny, one for Q, one for recon, one for Picasso, one for dot LA, et cetera. So they're all in different slacks. And then I have different email addresses for every company that I'm involved in. And so my email inbox kind of keeps it all straight because everything is according to whichever company I'm working on and my Slack keeps it straight. I don't do anything on my calendar to keep things organized like that. I don't do a day on Picasso, a day on Libby or anything like that. My calendar is I mostly play defense on. That makes sense. And then do you block out times? Are you able to go from Picasso to all of these different companies? And then can you just go straight through like that? Yeah, I do just go straight through all day long. All day long, it's 20 minutes on this company, 100 an hour on that, half an hour on this. So the earlier part of the conversation about how does this compare with when I was running Zillow? In a lot of ways, it's more exhausting. It's more mentally taxing. At the end of the day, at 6 p.m., 6.30, I need to exhale. It's a lot because of the context switching has an additional tax, a mental tax, that it's probably like being an ER doctor, where you walk into the room and is it a kid with a broken ankle or is it a gunshot wound? And it's like, OK, now I'm in the next room. And it's like, oh, it's a flu or whatever. It's very different than being focused on a single specialty. But it keeps it interesting. And I bet that problem is worse because most of it is over Zoom. And so you're actually doing way more meetings because you're not walking around. You have bathroom breaks. Like at Zillow, you're kind of like roaming the halls. You're right. And actually, I did use to block a lot of time at Zillow MBWA on my calendar. Management by walking around. And I would block half hour, hour, two hours. What is that? I mean, I would put on my calendar MBWA, which stands for management by walking around. And it would just be time where I would just walk the halls. And it was probably the best time I spent every week. What? A couple hours a week of I would just sit down with my iPhone. I plopped down at a desk. There were no offices. Everyone was open space. I plopped down at a desk and just do email on my phone. And then people would come up to me or I would overhear things. And I would go talk to people or I'd walk on the sales floor and grab someone's headset and phone jack in to listen to them talking to customers for a while. I'd walk up to an engineer and ask them what bug they're fixing or what they're working on or I just crash a meeting. And that was invaluable. And obviously, you can't do that on Zoom. Yeah. You mentioned dinner with your family now. I asked about your dinner table when you were growing up. But are you intentional about dinner with your family now? I am. We do our best. It's not 100% hit rate, but at least half the time we do a family dinner. I print a lot of articles. Tons of things that I see on Twitter or things that people send me or things that I read. I print and I always have a stack of papers of articles that I think are relevant or interesting to my kids. So you give it to them? I read them. I read it or I make a kid read it and report back to the rest. Or you see a reading comprehension. So it's like, you know, tech news or science news or whatever, you know, what I'll show you after this. I'll show you what my current pile is. And that generally happens at the dinner table. Yeah. That conversation. I ask because, first of all, that's actually really cool. I've never heard that kind of hard, but really cool. And second, I ask this question. It's my favorite question just because I think values are instilled and shared with the family at the dinner table. Yeah. It's important. It's important. Do I appreciate you doing this? Can I ask you, like, take away all this work stuff. What's something you're excited about personally? What are you jazzed up about without anything to do with work? Gosh, I mean, really just my kids. I don't know. I mean, my daughter's a first year in college. And I'm so excited about that and excited for her and excited about the chapter that she's just embarking on. And I'm not playing as big a role in her life as I was when she was here at home, but I'm excited about helping support her through this next chapter. And I'm teaching at Harvard a class on that's where she is. So in the spring semester, I'll be teaching a course there. Not to her. She's not taking it, but she won't take it. No, I don't think so. But I'm excited to teach. I've taught at Harvard now three. This will be my third year that I'm teaching there at the college and the business school. And so I love teaching, but I guess, I don't know, when you ask-- - I'll accept that as not work. - Yeah, it's work-ish, but I mean, honestly, but it's mostly, and I guess I'm boring like that, it's mostly work and kids, that's kind of the stage of life that I'm at. - I'll give you a hiring shout out for any of the companies that you're involved in right now or any of them hiring. - Almost all of them are, very selectively in sort of limited ways. You can reach me on my socials on Twitter, on LinkedIn, on any of my socials. My website is 75andsunny.vc, but you can find me on social and feel free to reach out. - Last one, when you hear the word grit, what or who do you think of? - Maybe it's 'cause you mentioned it earlier, but Tom Brady definitely comes to mind. I'm looking at a picture of Russell Wilson here in my office. I guess that comes to mind. Can I say me? (laughing) - You can definitely say you. You know what? You would be one of two guests that has said you, and it's badass. - And it sounds so arrogant. - You know what I know, you know what else was? Have you heard of Carl Eschenbach? - I have not. Carlushenbach was the COO of VMware. Then went, this guy is a machine, okay? He travels with a jump rope in his bag at all times. And went to Sequoia as a GP for the last six years. Talk about people reinventing themselves. Became like one of the most gangster investors in the Valley. Did all of these incredible growth fields. And now his wife was like Carl, every day, you feel like you're not doing the hard thing. You need to go back. His mirror, his careermate, is also his wife. And he is now the CEO of Workday. He left Sequoia to go be the CEO of Workday. And so I am not surprised to bring it full circle. And I do believe that you are an incredible personification of grit. So thank you. Thank you for having me. That's it. Thanks for tuning in. Feel free to come back every Monday morning to listen to a new guest or go back into the archives when we've done more than a hundred episodes. This podcast is a Clienter Perkins production. And the episode was edited by Eric Johnson from LightningPod. Thank you all.