Sept. 1, 2022

Zillow CEO Rich Barton on the Future of Real Estate and Home-Buying

Is the housing market finally cooling down?

Nora chats with Rich Barton, the cofounder and CEO of Zillow. He offers potential solutions to the housing crisis, and his view on the future of real estate and home-buying. We’ll also hear about why Zillow has adopted what it calls a “Cloud-HQ” model, where employees are all able to work remotely. For more info on our presenting sponsor, check out


Host: Nora Ali

Producer: Olivia Meade   

Video Editor: Sebastian Vega

Production, Mixing & Sound Design: Daniel Markus, Griffin Jennings

Music: Daniel Markus & Breakmaster Cylinder

Fact Checker: Kate Brandt 

Senior Producer: Katherine Milsop

VP, Head of Multimedia: Sarah Singer 


Full transcripts for all Business Casual episodes available at


Nora Ali: For Morning Brew, this is Business Casual, bringing you conversations with people you know, and some you may not know yet, to make business less intimidating. Because money talks, but it does not have to be dull. I'm your host, Nora Ali. Now let's get down to business.

The housing market is confusing and has felt kind of bonkers lately. We saw two years of skyrocketing prices, where it has felt nearly impossible to buy your first home, or any home, unless you're super rich. But where do we stand now? And are things getting back to normal? According to Zillow's Chief Economist, Skylar Olson, "The housing market is still far from a return to normal conditions. And the current slowdown is prompted by the collision of extreme price growth during the early and mid-pandemic, with the sudden increase in mortgage rates since December."

Well, that doesn't help us feel any better. So what does this mean for you if you're a prospective home buyer? Will you ever be able to buy a home? We got the scoop from Rich Barton, the cofounder and CEO of Zillow. He offered what he thinks are some solutions to the housing crisis, and his view on what the future of real estate and home buying will look like. And he knows a thing or two about getting ahead of and setting trends. The way he sees it, Zillow turned on the lights in the room in the real estate business, allowing the home-buying process to become digital for really the first time when it launched its site in 2006.

Another thing that impacts how and where people live: the future of work. Zillow is adopting what it calls a Cloud HQ model, where employees are all able to work remotely. And Rich knows a thing or two about work and workplaces. He cofounded the job review and recruiting site Glassdoor, and is also the founder of travel site Expedia. So basically he knows things, and he shared a bunch of that knowledge with us on this truly enlightening episode. That's next, after the break. Rich, hello. Welcome to Business Casual.

Rich Barton: Hey Nora, how you doing?

Nora Ali: I'm doing so well. I'm in a great mood. So Rich, we're very excited to have you on Business Casual. A lot of topics to get to: the future of work, the future of the home. But let's start with a little icebreaker. It's called Professional Pet Peeves. So Rich, you've worked in a lot of different office environments, interacted with a lot of people in your career. Don't get nervous. So if you could just wave a magic wand and get rid of something that people do at work (or don't do at work) that you find annoying, that you could get rid of, what would that be? What is your professional pet peeve?

Rich Barton: I'm kind of a word person; grammar stuff bugs me. Here's kind of a verbal tic pet peeve. "Am I making sense, Nora? Am I making sense?" That one. When people say, "Does that make sense?"

Nora Ali: Yes.

Rich Barton: I'm like, "You're worried about me understanding what you're trying to say?" If it doesn't make sense, I will tell you it doesn't make sense and ask you to say it again, maybe in another way that will make sense to poor little me. Anyway, that is something that bugs me a little bit. I realize that's not a big thing. Work has not been work for the last few years, has it? So I'm actually struggling for real-world examples. I have some digital ones, but anyway.

Nora Ali: Yeah. No, digital ones are good too. We had someone say that they just really dislike after-hours Slacks, because we see that a lot, obviously, right? I think there might be even more workplace pet peeves in the digital, the hybrid world. There's just so many more ways to communicate with each other.

Rich Barton: I think a lot of things that people might say are pet peeves, like a pet dog or cat or a child wandering through the screen or whatever, I think might annoy a lot of people. In my case, I kind of love that.

Nora Ali: Yes.

Rich Barton: I love getting a little window into people's real lives.

Nora Ali: Me too. All right. Well Rich, like I said, you have an incredible career. You founded Expedia. You cofounded Glassdoor. You cofounded Zillow, which you're currently CEO. Do you ever think you'll reach a point where you're going to stop? Aren't you tired, Rich? You're still chugging along. How? How?

Rich Barton: Nora, I'm so hurt right now. "Oh, you've been around so long. How could you possibly have any more energy?" Here's the thing, I love what I do. I love building cool stuff for people, with teams of people and using technology and ideas to change the world. I really, really love that. I hope there's never a time when I don't want to be doing that stuff. I'll tell you one thing that's got me super duper energized right now, which I know we're going to talk about though, is the workplace itself is being reinvented right now post-Covid. It's kind of like the Big Bang, and we're trying to figure out what 9.8 meters per second squared, which is gravity, gravity acceleration. We're trying to figure all out the early physics right after the Big Bang. We're all inventing that together. So I'm super excited about that.

Nora Ali: That's a great analogy, because it really does feel like such a fundamental shift. It's not like incremental changes. We're all totally reimagining what work can look like. So Zillow is being described as a cloud headquartered company. What does that mean exactly? And what excites you about it?

Rich Barton: I call it Cloud HQ. Everybody wants to say "remote work," or...I actually hate the term remote work. I mean, who really wants to be remote all the time? We're social creatures. And it also kind of implies we're never going to get together, which is completely wrong. I prefer, I coined the term Cloud HQ. We coined it. I don't know who came up with it, but shortly after Covid hit. The reason I like it is that because it implies a kind of new office space, a new workspace, the norms of which, the tools of which, the ways which we work are going to be reinvented in the cloud. And it's not like we're just going to take the stuff from physical world and put it into the cloud. It's actually, we're going to invent things new. And it also implies that, hey, convention, what we call Z retreats, Zillow retreats, like getting together and being with people and team building, and just getting to know your compatriots, absolutely still happens, but then we kind of go back to the cloud and we get things done way more efficiently.

Nora Ali: What does this mean in practice? Does that mean just more choice for the workers, for employees to decide when they want to get together, when they want to be in the office and when they want to work from home?

Rich Barton: It does imply a lot more choice. If we can all rewind our brains a little bit back to spring of 2020, when everybody was really scared and trying to figure out what was going on and were we ever going to come back to the office or whatever, you may remember a lot of companies doing what I called the hokey pokey. You put your left foot in. You put your left foot out. Anyway, it's been...Turn it all about. Anyway, the hokey pokey is kind of changing your mind and zigzagging on people all the time. And that's what was going on. Hey, we're going to be back by the end of the spring. We're going to be back in the summer. And what this ended up doing was taking employees and basically making them not be able to plan their lives. "But my lease in New York City is coming up in September. Can I let that lapse and go move back near my sick mom in Cincinnati?" And the company would say, "I don't know, you gotta be on call. You got to be ready to come back to the office." So anyway, we made a really smart decision. It was controversial at the time, but a really smart decision in hindsight. Kind of got lucky, just say, "No, look, let your lease expire. Go live your life. Move where you need to move. We're obviously working well together here in Cloud HQ, we will make it work no matter what on the other end." That's what it means to me.

Nora Ali: Yeah. And uncertainty is the enemy. If you don't know what decision your employer's going to make next week, a month from now, a few months from now, then that just upends your life. Why was it controversial at the time? Obviously everyone's opinions have fluctuated a lot during the pandemic, but at the time that you first made this decision, what was the pushback?

Rich Barton: Culture decisions are really hard, but what was controversial was a major wholesale change in culture and the way we work, and this base assumption pre-Covid that you needed to fly out for the interview to Seattle, have the interview, you're going to move to Seattle if you take the job or one of our other offices, and "work" meant you were going to be at work. And what seems like a small decision was a major cultural decision to say, "No, look, this flexible thing, this Cloud HQ, it has some drawbacks, but it feels like the future of work." All my spidey sense was tingling. It was kind of accelerating preexisting trends like Covid did to so many different things. And so we kind of held hands and we jumped and we said, "All right, go ahead and move. We'll make it work on the other end." We were very thoughtful, very quickly about some basic norms, the basic kind of rules of engagement in the cloud world, which were fun, too.

Nora Ali: What are some of those basic rules of engagement?

Rich Barton: I won't take credit for inventing it because I don't think I did. It may have been Matt Mullenweg over at Automattic, which is WordPress. His company has always been, actually he calls it remote. They've never had any offices and it's all over the world. So he kind of wrote a bunch of the rules ahead of time and was really terrific in giving us a bunch of advice. I remember having him on an all company Zoom really early in the pandemic, and everybody was like, "Oh my god, this guy's the Oracle." Anyway, one of those little mnemonics was, I call OZAZ, OZAZ, one Zoom all Zoom.

Nora Ali: What does that mean?

Rich Barton: Okay. "One Zoom all Zoom" means if even one person in the meeting that has more than three or four people in it, if even one person is not present and together, everybody scatters and Zooms in. So that everybody's on a level playing field. Everybody gets a rectangle. Everybody gets a name tag. It's not a two-class system. The people in the room who are the decision-makers and get all the air time, and the people out of the room who feel like, "Hey, hello, I'm here. Can I make a point?" Anyway, that's kind of the history of having people on the phone outside of headquarters. And so OZAZ was a very controversial rule as well. My friends at Microsoft would rather I say OTAT, "one Teams all Teams," but that was a pretty controversial one that I had to push pretty hard on.

Nora Ali: Yeah, and it puts everyone on an equal playing field. So you don't feel like if you're the one who happens to be able to be in the room, then you have a louder voice. And I think that also translates to the hiring process too. If you allow people to work from anywhere, then I imagine you're getting more representative candidates. You're being more inclusive in the hiring process. Can you sort of talk to how this Cloud HQ model creates more access for different kinds of employees?

Rich Barton: I mean, it just dramatically widens the net that we can throw to cast for talent, right? We used to be able to only get people within N miles of where we had an office, or someone who was willing to move to Seattle. This actually casts a much wider net. So way more inclusive. It makes the recruiting process super duper easy, as I was saying before. Because of that wider net, of course, we were able to embrace all kinds of new geographies, which naturally made us more diverse. We dramatically moved the needle on all of our diversity metrics, which you can say, oh, is a good thing, because it's just a good thing and the right thing to do. Well, yes, there's some of that, but it's good business, like having a more diverse workforce in what we do...and I think everything, by the way, is just good business. Well, first our customers are everyone, and everyone is diverse. Okay? And so we need to design products for and service those customers with a diverse workforce. We're going to do a better job, but beyond that, a fundamental tenet of capitalism and success in capitalism is inclusivity. The more people you can include in the market, the better and healthier the market gets. And so being able to cast a wider net and be much more inclusive is just a strong business proposition.

Nora Ali: Even the little things, to your point about making it easier to interview for a job, not having to travel there. I remember having to take days off of work to go interview for other jobs. And then you end up having to lie to your current employer. It just feels wrong. And you as an employee should feel empowered to find the job that's right for you, and make a switch when you want to make that switch. So you have written about this larger untethering of your location, where you live, from where you work, and how it's so important to the future of work and life. And by implication, this impacts the housing market. So what is the impact so far that you've seen on the housing market, where people can choose to live, and it's not necessarily exactly where they work?

Rich Barton: I mean, I think we have seen an acceleration and a trend towards what I would call labor dispersion. We're just going to see more dispersion in where people call home, because as more companies offer more flexible work like Zillow and Cloud HQ, we're going to see more people actually taking the option to live somewhere that is not necessarily in or near an urban center.

We coined the term early in the pandemic when just the housing market started to go crazy. Just crazy, crazy, in terms of numbers of transactions and people shopping and using Zillow and going to houses and transacting houses,'d think, oh, that market should stop because people were worried about getting sick. No, it actually went crazy because everybody was looking for a new home. Everybody was completely reassessing what home meant, and home was serving as a gym and an office and not just a place to sleep and to have your dog or your family or what have you. And so people were becoming dissatisfied with their homes and were anxiously looking elsewhere. Everybody started to lift up their eyes and look around and see what other ways and places they might live. That is absolutely continuing today.

Nora Ali: A lot more flexibility, a lot more freedom. A lot to discuss on the housing market, the future of housing, but we're going to take a very quick break. More with Rich when we come back. So Rich, I want to back up a little bit. We all know Zillow, but I want to provide a little bit of context for our listeners who may not have used it before. You've said that the Zillow brand has become synonymous with real estate empowerment, but "the fundamental transaction continued to be painfully stuck in the 1950s, resisting the gravity of digitization. So our expanded dream is to re-engineer, streamline and digitize the moving process."

Rich Barton: Wow.

Nora Ali: Beautiful. You wrote that, Rich.

Rich Barton: I did, actually. I did. I did. Maybe Christy did. I don't know. Anyway, yeah, I love that. I love that.

Nora Ali: Being wowed by your own words. That's great. So for people who haven't actually used Zillow through the home-buying process, how has Zillow changed home buying since you founded it?

Rich Barton: We turned on the lights in the room. We let there be light. That might be a little grand. Many of your listeners won't even remember what life in the real estate shopping industry was like before Zillow came along and turned on the lights, but it was a dark, scary place full of creepy crawlies and people hiding things.

Nora Ali: What was it like? Can you actually explain to our listeners who, you're right, probably haven't experienced the housing market pre-Zillow?

Rich Barton: Literally there were no listings on the web. You couldn't search for what's for sale. You couldn't get addresses. You couldn't get prices. I don't want to be too hard on the industry, but the industry had a good thing going, where they protected all this information. And if you needed any information about how many bedrooms, what was for sale, what the price was, you either had to walk by it on the street and see a sign. I'm not kidding. And there used to be these little containers that had flyers under the For Sale signs in a house neighborhood and that's where you could get the details on what it was for sale for. Other than that, you had to call somebody. 

Anyway, my cofounder Lloyd Frank and I had just done Expedia, which we turned on the lights in travel, by the way. It's same idea. There's nothing new under the sun. We turned on the lights in the travel industry, which was exciting and empowering. We were having kids and shopping for homes and we couldn't believe how hard it was to get basic information. And this was in like 2005, 2006, which sounds like a long time ago. I mean, it was before the iPhone, put it that way. There was no mobile web.

Anyway, we were building spreadsheets and trying to grab data to figure out what homes were worth. Because we were having babies and we needed a new house, and we were like, "Oh my God, we have to do this in real estate too. We have to turn on the lights." So Zillow's fundamental thing was to basically democratize access to information. We say "power to the people" a lot. And in empowering the people, to figure out how to end up building a marketplace that worked much more efficiently and fairly. And that was our project that we began 16 years ago. And we've only just begun. We have everybody come to Zillow. You were saying, we have a trusted brand that everybody knows, which is true. We make fun of it on Saturday Night Live. I don't know if you saw that Saturday Night Live spoof that we had, which was so fantastic.

Speaker 1: You need something new.

Speaker 2: Something exciting.

Speaker 3: I need a new fantasy.

Speaker 2: Then you need—

Speaker 1: Zillow.

Speaker 3: Zillow.

Rich Barton: That's the pinnacle for anybody who builds a product, is to be spoofed on Saturday Night Live. Anyway, we were spoofed, which was fantastic. And we had 200 million people a month come to our sites and apps. And yet we only have 3% transaction share is what we've monetized so far.

Nora Ali: Oh.

Rich Barton: We get everybody. We only monetize 3%. So what keeps me really excited is we have all this immense growth opportunity to fundamentally really now begin to change the guts of the industry and really digitize it and make it way simpler for everybody out there who's listening, who's gone through this process or maybe going through this process in the future. Our job is to be your digital quarterback. It's going to be a long-term thing, but we want to be able to make it easy for you and your partner and your professional partners as well to monitor and take step by step as you walk over that bridge to that new place to live. That's what we're building.

Nora Ali: That stat, you're only monetizing 3% of transactions on Zillow, or in the housing market?

Rich Barton: 3% of housing transactions. That's the revenues we have and we're a pretty good-sized public company. We're a big company, but it's a huge industry. And so our whole schtick from a business model perspective was, hey, turn on the lights, get the audience, do what's right for the customer. Get a massive audience and then figure out how to create a business model around having that audience. It turns out we're only kind of 3% down the road on that journey of figuring it out, which makes it fun.

Nora Ali: So what does growth mean then? Because the opportunity is clearly there. I know you have a partnership with Opendoor, which is perhaps Zillow's re-entry into iBuying. So let's talk about Opendoor a little bit. First, just explain in very basic terms what iBuying is and then what this partnership with Opendoor now allows you to do.

Rich Barton: iBuying is a relatively new thing. There's been an industry of local cash buyers for your house for a long time, but historically it had a little bit of a predatory feel to it, okay? Like take advantage of somebody in a bad position. That industry, before Opendoor came along, really didn't have a fantastic reputation, but Opendoor came along and said, look, if we can do this at scale, we can do it in a way that really just offers a cash offer as a service and isn't trying to be predatory.

We played around at Zillow for a couple of years, trying to be a primary in that business ourselves, which meant we were buying and selling homes, but it just turned out our business and risk profile and the size of the opportunity we had outside of iBuying just wasn't set up well to have us owning a bunch of homes and keeping them on our balance sheet. So we exited that business and we recently did a great deal with Opendoor, where all of the millions of sellers that we know are coming to Zillow app, many of them may be interested in getting a cash offer for the markets where Opendoor operates. And so now through this partnership, we offer a really deep integration for an Opendoor cash offer as an option for sellers. And then Zillow has an option to provide for the ones who don't...most people will not take a cash offer. And so they'll sell traditionally. And so we can offer a whole bunch of our partner services for those movers. So it's kind of a peanut butter and chocolate partnership opportunity for us.

Nora Ali: So you're clearly trying to make the whole experience a little less painless for both buyers and sellers, but the housing market does, especially now, feel quite painful, especially for Gen Z and millennials. First time home buyers. There's a recent survey from YouGov that found that most members of the Gen Z and millennial generations, that's US adults between the ages of 18 to 25 and 26 to 41, they do want to own a home someday or even right now, but their biggest roadblock is affordability. Nearly three quarters of American adults still view home ownership as a top hallmark of achieving the so-called American dream. People want to buy houses, but it feels a little bit impossible right now. Is there a specific way that Zillow is trying to cater to these younger generations and demographics who are prospective homeowners, who are digital natives and they grew up with technology? They grew up only knowing Zillow. How are you catering to those folks?

Rich Barton: We're really interested in first time buyers and have great empathy for how difficult it has become for the first time buyer in the kind of post-Covid housing market, where we've seen affordability worsen. Mortgage rates have gone up a lot and house prices have gone up a lot, which is a pretty bad combination if you're shopping for your first home. Home ownership has been the greatest source of wealth creation for everyday Americans. North of 60% of American families own a home and a preponderance of household net worth is tied up in the equity of home, which is a fantastic place to actually have that. And so the big step is getting into the first home. And so this is just a matter of life happening, and you taking the leap. There's a point that comes when you have the first kid or the second kid or whatever it is, and you have a dog and maybe you need a yard and you just say, all right, I know it's difficult, but I'm going to do what I can to take the next step. And that involves getting a down payment together. So you have to have saved, you have to have your credit score in good shape. And then something we're really focused on at Zillow right now is helping you get the right financing. Get preapproved and get a mortgage, so that you can go shopping and you can have confidence that you can afford what you're looking for.

So yeah, we have a real interest in helping people do that. We do recognize it's become a little bit more difficult in the near term. However, the great thing about capitalism is that supply and demand end up doing their own thing. And when we have a lot of demand for homes and yet we don't seem to have enough homes on the market, that will correct itself over time.

I would encourage all of you out there to pressure our governmental leaders, mostly on a local basis, to make it easier for more housing to be built, which means we got to have cities go more vertical, and we've got to kind of relax zoning laws.

The final thought I'll have here and then I'll shut up, Nora, is that a wonderful thing about flexible work in Cloud HQ, for the relatively smallish percent of the work population that are information workers that actually can work flexibly, it enables us to look a little bit further out, right? And so when we look a little bit further out from urban cores and suburbs, we're actually able to afford a lot more home. And so we are actually seeing a lot of that going on, which helps with affordability.

Nora Ali: Yeah. I mean, I appreciate your optimism and believing in the supply-demand dynamics will shake out. They do. It might take a while in this case, but there's so many forces right now where, for example, people are looking at homes as an investment. So if you're wealthier, you might buy up more homes as an investment. You might not necessarily need them to live in. So you're reducing the supply. And then there's people who are buying homes to rent out on Airbnb as a source of passive income. What are your thoughts on people buying homes as investments, when they are taking the supply away from those who might need it?

Rich Barton: I mean, I think there's a little bit of a misunderstanding and a little bit of a boogeyman thing going on with this particular narrative, because the really large majority of people who buy homes for investment reasons are renting them out to people, okay? So it's not actually taking homes away from people and families to live in. It's just providing a way to get in via a rental. And the rent versus buy market tends to be pretty darn efficient. And when it becomes more efficient to actually be an owner than a renter, then that begins to really happen. And I think we're in one of those periods now, because rents have actually grown even more quickly than housing prices. And so we're kind of seeing that now. On the Airbnb thing, I think that's got to be just a little bit of noise.

Nora Ali: Just a small sliver. Yeah.

Rich Barton: And by the way, not a bad thing to have people actually traveling around and interacting with the world in different places. I mean, I'm a big fan of travel. I think that of course there are some neighborhood dynamics or building dynamics where too many Airbnbs are in a building and people are loud. I mean, there are those kinds of problems, but in general, I think we are better as a species when we interact with a lot more different people.

Nora Ali: I could not agree more with that. So we're seeing a lot of different entrepreneurs and business people trying to tackle the housing crisis and housing issues. And one of them, of course, is Adam Neumann, the infamous founder of WeWork. He's now building Flow, just got a $350 million investment from A16Z. And that aim is to address housing availability. There's community considerations. It plans to operate more than 3,000 apartments that Neumann acquired, blah, blah, blah. It's a lot of stuff that Adam Neumann is trying to tackle. But availability of housing, as we've been talking about, is clearly a big issue. Maybe Adam Neumann is not going to solve it, but what do you think will fundamentally help ease the housing crisis and make homes more accessible to more people? You mentioned things like zoning and just reaching out to local politicians so that they're working on it, but what do you think is going to really help solve this issue?

Rich Barton: I know Adam, and I think Adam is an extraordinary guy. And interestingly, where I am in Long Island right now, he's actually a neighbor. So I know him a little bit and I see him a little. He's just truly an extraordinarily interesting, thoughtful, and charismatic guy, but controversial. I get it. The idea that Adam is doing with Flow is something that is being done already, though Adam I'm sure will put his new spin on it. The solution is more capacity, Nora, more housing capacity. We need to be able to build more homes and more apartments. And pretty much anything that enables that is a positive.

In pretty much all cases, the locals who are in the areas where that wants to happen, don't want that to happen. They think it will depress the value of their asset. And so they're just defending their asset, generally speaking. So we as a society and through our government, we need to actually say, "Hey, no, this is a social need. Look around."

I live in Seattle, for those who live in San Francisco or LA, we have real homeless issues. Just look around, we need more housing. And so we as a company at Zillow do a whole lot of stuff socially to support the kind of public policy that will build more housing. And I believe so should you, the listeners.

Nora Ali: All right. We went over a lot in that answer. A lot of good nuggets in there. Let's take another very quick break. More with Rich when we return. Okay. Rich, let's get to some of the fun stuff. So you had alluded to Zillow being spoofed on SNL. Zillow surfing became popularized during the pandemic. Taylor Lorenz wrote a piece for The New York Times called "Zillow Surfing Is the Escape We All Need Right Now." There's Zillow Gone Wild. The Twitter account has 300,000 followers. The Instagram account has 1.6 million followers. Is that, at the end of the day, good for Zillow? What do you make of this social phenomenon, the cultural phenomenon of Zillow?

Rich Barton: Oh my lord, I'm tickled. I'm completely tickled. Lloyd and I made up the word and now it's a verb. I mean, it's really, really wonderful when you create something that really catches, okay? And maybe that's happening with you in your podcast right now. I think it is, right? So when you've done something and it really catches, that feeling you get, it's pretty difficult to describe, right? So I'm completely tickled and I've been lucky to be a part of several interesting, fun things like that. But I think Zillow is a particularly big one, which is fun.

Nora Ali: I mean, it's fun to dream. You're not just making it easier for people to buy and sell homes, but you're allowing people to aspire to what they could have in the future. And I personally follow those accounts. I've Zillow surfed before, just to see. You just want to check, in this location, if I happen to move there, can I afford this home?

Rich Barton: I really think it's fantastic. I'll tell you something. The headline in The San Francisco Chronicle in 2006, when we launched, and there really was a San Francisco Chronicle in print then, the headline in the business section—it wasn't the front page—when we launched, a brand new startup, top above the fold, was Zillow Launches: Real Estate Porn. So many people showed up the first day, the site went down for 36 hours. And I remember being curled up in a ball on the couch of our CTO, who's still our CTO, David, saying, "Make the pain stop."

Nora Ali: But that's good, right? Too much traffic is better than not enough.

Rich Barton: That actually is exactly...Amy Bohutinsky was our marketing chief at the time. And she's like, "Don't worry. We're going to make lemonade out of this one. Don't worry." And the headlines the next day were, "So Popular Tips Over." It was good. Yeah.

Nora Ali: Oh my gosh, that's amazing. Okay. Awesome. Well, Rich, we have a fun segment for you. Going to exercise your brain a little bit.

Rich Barton: Okay.

Nora Ali: It's for a segment called Shoot Your Shot.

Rich Barton: Shoot my shot.

Nora Ali: So I would love to know...Yeah, shoot your shot. You've accomplished a lot. Started a bunch of very successful companies, but what, if there still is one, what is your wildest ambition and your biggest dream? What is your moonshot idea? It could be personal. It could be work related. It could be world related. It's your chance, Rich, to shoot your shot. So go ahead.

Rich Barton: I've been lucky that I've actually been on the moon a couple times already. I really have, and I'm super grateful for that. I really am. And I credit the team of people that are with me, being able to have that feeling. What I dream about now, from a moonshot perspective, this kind of digital integration, this kind of housing super app dream that we have at Zillow, which is a really long-term thing that we're dreaming about, is going to be super hard. It's such a snarl of an industry with so many moving parts and so many hungry mouths and so many regulators and so many things to sign. And I call it the chasm of despair. We're building a bridge for people over the chasm of despair, and where they are now is the current place they live. And on the other side, it's sunny and beautiful and a nice garden. And we want to keep them above the snakes and cacti and crocodiles and get them over. And I think if we can do that, that would make me very happy. Yup.

Nora Ali: Well, Rich, is there a personal moonshot you have? Because I mean, it's all been work related so far. Do you want to go physically to the moon? Maybe that's a moonshot—

Rich Barton: No. No. No, I don't. I don't. I don't. I don't. And I have friends who've done the international space station thing and it's—

Nora Ali: Oh my god.

Rich Barton: They're so excited. I have one friend who's gone there twice, Charles Simonyi. It's just wild.

Nora Ali: That's such a funny flex. "I have friends who have gone to space."

Rich Barton: He was one of the first guys. And then he went back on a Russian rocket. And he called me from space, Nora.

Nora Ali: No, no. What?

Rich Barton: Okay. I'm not kidding, but this is a while ago. I had a Nokia phone.

Nora Ali: I don't know you could do that. What?

Rich Barton: This is pre-smartphone, okay. I've got a Nokia.

Nora Ali: Playing Snake on your Nokia?

Rich Barton: Seriously. Seriously. This is a long, I'm dating myself, this is a long time ago, but I'm sitting there. We had started Zillow, I think. So it's early. This must have been like 2006 or seven. And I get a call from an unknown number on my Nokia flip phone. And I normally wouldn't answer an unknown number, but I answered it. And Charles is like, "Rich! It's Charles." I'm like, "What? What? I saw you blast off into space." Like, "Yes, I'm at the International Space Station." I'm like, I grabbed everybody that was in the office and there were only eight of us at that point, and we all huddled around the Nokia phone and chatted with Charles. No, I don't want to do that. I don't need to do that, personally. Here's the thing: I believe that the happiness equation is...are you ready?

Nora Ali: I'm ready.

Rich Barton: Something to do, someone to love, something to hope for.

Nora Ali: Wow.

Rich Barton: And you're happy. As you age and you have a family, and I don't know if you have a family, but I've got grown kids. Something to do, I've got nailed. Someone to love, I've got a lot to love. I'm really lucky. Your hopes actually get transferred from yourself kind of onto your kids as you move through life. And so my hopes and dreams are now for my three fantastic, awesome children, who are very different people who I love a lot. I don't want to put pressure on them or anything, but I have great hopes.

Nora Ali: That's beautiful. You hope through their eyes. That's wonderful. Awesome. Well, Rich, we will leave things there. This was so fun. Thank you for joining us on Business Casual.

Rich Barton: Thanks a lot, Nora. Great to be here.

Nora Ali: This is Business Casual and I'm Nora Ali. You can follow me on Twitter @NoraKAli. And I would love to hear from you. If you have ideas for episodes, comments and thoughts on episodes you loved, fun segment ideas, just shoot me a DM and I will do my very best to respond. You can also reach the BC team by emailing, or call us. That number is (862) 295-1135. If you haven't already, be sure to subscribe to Business Casual on Spotify, Apple Podcasts, or wherever you listen. And if you like the show, please leave us a rating and a review. It really, really helps us. Business Casual is produced by Katherine Milsop and Olivia Meade. Additional production, sound design and mixing by Daniel Markus, with help in this episode from Griffin Jennings. Kate Brandt is our fact checker. Sarah Singer is our VP of multimedia. Music in this episode from Daniel Markus and The Mysterious of Breakmaster Cylinder. Thanks for listening to Business Casual. I'm Nora Ali. Keep it business, and keep it casual.