Zillow CEO Rich Barton on branding, building in provocative industries, and more! | E1791

11 Aug 2023 · 1 h 21 min

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Podcast Episode Summary: Zillow CEO Rich Barton on Branding and Innovation | E1791

Podcast Title

This Week in Startups

Host

Jason Calacanis

Episode Overview In this episode, Jason Calacanis interviews Rich Barton, CEO of Zillow and founder of several other successful companies like Expedia and Glassdoor. The discussion revolves around branding, the evolution of technology management, and the innovative strategies that shaped Zillow's growth.

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Key Themes and Discussions

  1. The Evolution of Zillow and Branding
  2. Creation of Zestimate: Rich discusses the inception of the Zestimate, a tool that provides home value estimates, highlighting its role in generating media attention for Zillow.
  3. Provocative Marketing Strategy:
  4. The Zestimate’s provocative nature drew significant consumer engagement.
  5. This approach turned potential criticism into a marketing opportunity, cementing Zillow's brand presence.
  1. Lessons Learned from Bill Gates
  2. Rich shares insights from his time at Microsoft, emphasizing the focus on product quality and the critical nature of consumer engagement.
  3. He reflects on Gates’ reputation for being a tough critic, which shaped his approach to product management.
  1. Navigating Challenges in the Real Estate Industry
  2. Market Dynamics and iBuying:
  3. Discusses the challenges faced by Zillow’s iBuying initiative, particularly in terms of market volatility and operational risks.
  4. Emphasizes the importance of understanding both consumer needs and market conditions.
  5. Impact of COVID-19:
  6. COVID accelerated trends towards remote work and reshaped consumer behavior in real estate.
  7. Rich notes how Zillow adapted to these changes by shifting to a cloud-based operating model.
  1. Cultural Shifts in Tech Management
  2. Rich shares his perspective on evolving company culture, moving from a “pirate ship” mentality to a more inclusive and respectful environment.
  3. Discusses the importance of mentoring young employees and the challenges of maintaining personal connections in a remote work setting.
  1. The Future of Work and Real Estate
  2. Rich predicts a shift in urban living dynamics, with a move towards intermingling work, life, and shopping spaces.
  3. He discusses how high interest rates and market conditions may affect real estate transactions and the necessity for flexibility in company policies regarding remote work.

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Key Takeaways

  • Branding is Crucial: Innovative branding strategies can turn challenges into opportunities, as demonstrated by Zillow’s approach to the Zestimate.
  • Consumer-Centric Philosophy: Prioritizing consumer needs over supplier pressures can drive marketplace success.
  • Adaptation is Key: The ability to adapt to changing market conditions and consumer preferences is critical for growth.
  • Empowering Employees: An inclusive company culture fosters creativity and innovation, which is essential for long-term success.
  • Future Trends: The integration of work, living, and recreational spaces will shape future urban environments, highlighting the need for real estate companies to stay ahead of these trends.

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Conclusion Rich Barton provides a masterclass on branding, innovation, and navigating the complexities of the tech and real estate industries, emphasizing the importance of consumer engagement and adaptability in a rapidly changing market. His experiences at Microsoft and his strategic vision for Zillow offer valuable insights for entrepreneurs and business leaders alike.

For more information, you can follow Rich Barton on [Twitter](https://twitter.com/Rich_Barton) or explore his branding insights on his blog [Hopper and Dropper](https://www.hopperanddropper.com/syllables-scrabble-letters-and-picking-brand-names).

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Transcript

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0:0012 years ago when I started this show, it was, you know, a thousand people listening. Now it's a quarter million. And all in is a million. You know, it's a lot of listeners. and i was getting my blood drawn because i'm on this health kick and the phlebotomist came to the house and he's like halfway through taking 20 pints and he's like i just want to say and i was like fan of the pod he said yeah i said you want to take a selfie he said i really do but i get fired whatever i said let's do it don't tell your boss then i go to dinner the same night and i'm like i gotta eat a chicken parm i saw somebody had tweeted a chicken parm so i go i get a chicken farm find the best one on yelp the waiter's like i hate to do this and i'm like fan of the pod big time i go to berkeley or whatever and i was like okay you want to take a selfie yeah i said let's do it in the parking lot so you don't get fired so he went to the back in the parking lot i take a picture with him it's very weird it is very weird well congratulations you should feel good you've been working out a long time so well done yeah you know i think it's like uh there's also something about like um doing things and i think it's a really good part of our conversation.

1:05Hey, everybody, welcome to This Week in Startups. Rich Barton is here. We're off to the races. This Week in Startups is brought to you by Crowdbotics. Great ideas can change the world. And Crowdbotics is the fastest way to turn those ideas into code. Get a free scoping session for your next big app idea at crowdbotics.com slash twist. OpenPhone brings your team's business calls, texts, and contacts into one delightful app that works anywhere. Get 20 % off your first six months at openphone.com slash twist. And FitBod. Tired of doing the same workouts at the gym? FitBod will build you personalized workouts that help you progress with every set.

1:47Get 25 % off your subscription or try out the app for free when you sign up now at fitbod.me slash twist. So Rich Barton is the, or was the founder of expedia glass door and now the ceo of zillow been trying to get him on the program for a while but he's like one of those quiet assassin executors you're not like super into doing media although you've had media at the core of a lot of your success in terms of strategies yeah yeah yeah we have uh you know i believe that the product should speak for itself and it should be amplified by earned media and word of good old word of mouth i i really believe that's the way the good stuff gets out there so i'm certainly familiar with media but i am relatively bashful that won't be coming through in the pod though jake well i mean we'll have a good time uh you and i have a lot of friends in common and we're you know we're just chopping it up talking shop but i i would like to just double click on this one immediately because i think you're being super humble when i meet with startups and they ask me hey i want to do earned media i want to earn some media i don't want to just hire a pr firm i want to have a strategy and you know what the first thing i i tell them to look at zillow and this estimate because i met your cmo remind me of her name amy butinsky she's on our board now but yeah amy and she spoke at a couple of my conferences i interviewed her on this podcast i don't know five six seven years ago you came up with the ultimate earned media for zillow maybe you could explain because she's explained it to me and i have some broad strokes here but from your perspective as the founder ceo of zillow maybe talk about how you created zestimate and then the local reports which then let you literally take over every quarter on a rolling basis the local news cycle for real estate which is adult um porn basically all right so there's a ton in there and he's just brilliant there's a ton in there and i can reach i could reach back and give a little context about how we got there and then i'll tell you about it if you really want to get the story yeah it goes back to another bestie of the pod bill girly oh bill girly led our a round and is a good friend and i was a uh venture partner a benchmark for 17 years so i'd done a bunch of stuff with bill and those folks and we were early early as ill we didn't even have the the the product quite down yet this is in 2006 and i had just come off selling expedient to barry diller um i had taken expedient public when i was 32 years old back in 1999 even you remember that yeah yep um that was when you know dogfood.com could literally go public we'll get into the expedia story that's a fascinating one but i take an expedia public and i was used to spending advertising money um and as we were getting ready to launch zillow girly said hey rich what if you had a zero dollar ad budget then what would you do and i was like okay what would i do i was like that's impossible of course you can't do that but like all all b hags big hairy audacious goals you think at first it's impossible then you go away and think about it for a little while and you start to shoot the shoot the stuff with your friends have a couple beers and think about well how how might we do that and so we basically ended up taking this project that turned into zillow and pivoted towards the creation of this estimate which most of your listeners and viewers out there everybody knows but it was everybody knows you gave an estimate on the price of a home and you did that through looking at recent sales in the home and then whatever data you had on the home that you had licensed if i understand correctly licensed a bunch of data yeah and it infuriated people because everybody believes that their house is worth 10 % more than whatever the highest priced house that just sold is and so then they all went to you and said how dare you i'm going to sue you i'm upset my house is worth 67 000 more dollars than this and then all of a sudden they know zillow they've logged in and claimed their home yes yes i would say i wouldn't be quite so negative on it and say yeah there was some negativity to it but it was very provocative so we used yes we used ai to create the originals estimate long long ago yeah and we we figured out we dropped this price on every house in the country we updated every night and it would be provocative from uh look up your old girlfriend's you know well you know from high school where she's living now what that house is worth we had a lot of that we had a lot of that's not right just like you said and we had a lot of hey i'm actually looking for a home right now and i want to know what the hell that thing's worth and so it was this interesting intermingling of the the the kind of titillating and the pragmatic which is a wonderful sweet spot to be if you're building consumer product if you can kind of if you can really get emotionally involved with your customer with the product but also be super pragmatic at the same time you're you're you're really digging in the right digging in the right spot in my opinion so there was some tension there just to unpack that because when you talk i mean i've listened to three or four of your interviews in preparation for this and i listen to it candidly i just respect you so much as an entrepreneur anytime i see like you're along with mark knoffler and like some other topics on my youtube you come up often so i see like nine-year-old interviews with you and girly or gerstner or whatever it's always great but i you gotta double click on that one there's some tension there yeah and that tension means attention and importance correct i like that i had never heard it put that way but exactly if there's no tension there's nothing interesting just like when you're telling a story there has to be tension and that tension has to be released and that's what a story is right did you ever study screenplay writing or think of being i didn't i didn't but i really do love you know i love like you do i love i love movies and books so who's your favorite director i think coen brothers coen brothers i'm really dating myself but like raising arizona oh my god i used to drive i used to drive back and forth to college across the country i mean nicholas cage right i mean nick cage and holly hunter and john goodman it was you know it's brilliant every line is brilliant uh anyway and so many of the coen brothers movies are that way big lebowski i mean yeah like how many times can you watch big lebowski you know that's you know repeatability i think is such an important characteristic this is why ridley scott is i think my number one you know scorsese ridley scott yeah you know they always just clog up my top list and i can watch gladiator or goodfellas any moment minute one minute 100 i'm watching till the end i can't get turned off can't change the channel do you know ridley scott do you know ridley scott did the did the original mac ad for steve jobs i didn't know that i feel like i did but in 1984 1984 will not be like 1984 that woman with the hammer throwing it through big brother on the screen it was like that was important to me i was watching it was in the super bowl it ran once that ad i think you're a little older than me you were born 1968 67 67 yeah okay so you're three years older than me so at that time when it came out in 84 you were 17 years old i was 14 yeah i had a pc junior what computer were you rocking at that time i i god i went through the 64 what were you on there it is i went through the trs 80 the commodore 64 at the time i probably had an apple 2e and this this was the moment right uh the rise of ibm was biggest in the personal computer business and this basically was supposed to represent all the mindless drones uh watching big brothers big head on the screen representing ibm and this is apple steve jobs and the mac this woman this athletic woman who is breaking the spell look at that it's so subversive when you think about it you've got all these i mean on a gender basis i didn't even consider the fact just knowing this iconic commercial that it's a woman coming in a you know uh uh you know basically uh running like like an olympian yeah to knowing that she's outnumbered and she's just going to blow up the screen with the man on it and all these drones It was so iconic and made you so enthused about the power of technology.

10:32It was an inspiring call for our generation, I believe. The power to the people is kind of how I've retrofitted my whole company creation philosophy that technology empowers the regular person to take on the man and bust the old ways. And like, this is what this ad did for me. And it has that very, you brought up Ridley Scott. it has that very blade runnery you know yes i be dark apocalyptic you know thing well man against the machine right and then the same thing with gladiator etc so this tension also manifested itself in glass door hey what's it like to work at this place yeah rate your boss and how much you're getting paid uh it's a you know another example of there's going to be some people who are inspired and empowered by this data there's gonna be a lot of tension as some people are gonna want stuff fixed hey this was unfair but you cannot look away you must engage that's right that's right that was that was how and why we launched glass door we had kind of this you show me yours i'll show you mine give to get model for for salary so you can anonymously share your salary and if you do then you can see what everybody else is anonymized salaries are for this job and wow what a wonderful power to the people liberating data thing you know it kind of came from a printer accident i had i was running zillow at the time and i accidentally printed everybody's review and salary and and and raises out in the common printer rather than my printer this is back when we actually had printers yes and i it nightmare luckily i caught it but actually it got me thinking well what if everybody did see it yes well it ought to make sense right like everybody who saw that ought to go yeah well xyz should be making that much money and deserves that raise because of the work that person has been doing and it got me and my co-founder at glass door is bob homan who had worked with me at xpedia uh development manager it got us brainstorming on how we might build a product around that anyway it was the same provocation marketing very interesting data the data coming out of glass door the data coming out of zillow we realized with folks like amy butinski we could actually create a machine that kept pumping that date that data out through local newspapers and local publications on a daily basis and we would we would we found that especially for real estate information but also job information there was kind of an infinite news hole like you know newspapers and and media outlets would publish interesting stuff every day about real estate and jobs if they could and and many of them do so we realized that we built an organization kind of bloomberg like to pump this data out into the world and that is how we earned our media amazing all right we all know the one thing that separates great startups from the good ones is product velocity what does it mean product velocity, fancy term, right?

13:33Here you got your product and your velocity speed, the speed in which your product improves. So can you ship updates? Can you release new features? Can you do bug fixes? Can you iterate on the interface? Can you solve problems for your customers? And can you do it quickly? Because you're not alone, you have competitors and your customers have choices, they may fit solve their problems by writing their own custom code, or they might use your solution. This is what startups are about. How fast can you get that product velocity going? And so, you know, how do you supercharge it? Everybody says, okay, yeah, we want to go faster, but you got to go faster intelligently.

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14:41That's a$4.99 value just for the Twist listeners. You get that for free. That's C-R-O-W-D-B-O-T-I-C-S dot com slash twist for a free build plan. going back to zillow and your experience there the other thing that i think you're a master of is branding expedia zillow glass door all of them just incredibly well done i'm a uh branding aficionado myself i know how hard it is to name stuff take us through the naming of each of those companies and how you got there i know you know this is something you're very passionate about and then you were and had an interview and you talked you said you had a whole theory about branding and the person was like that's great let me go to my next question and i like literally almost threw my phone against the wall because i was like he just told you he has a theory of branding the guys made three of the most iconic web properties or just properties companies and you literally let it go down the river and get lost forever so let's unpack this here okay rich spartans the theories on branding and creating iconic names go okay the title of the blog post is actually out there it's something like you know syllables and high point scrabble letters uh i do it's out there and back when you were already blogging a lot i tried to blog for a little while you know and you know how that goes for guys like me we do a few blog posts and we forget about it and it just sits there forever on the web so there is a there is a blog post that you guys can pull up and put in the show notes uh the website is called hopper and dropper.com that's a fly fishing term and there is a post in there on blogging there we go syllables scrabble scrabble letters and picking brand names here it is those of you on video are seeing it right now 2009 i wrote this love it this is after the great financial crisis so you're probably somewhere just absolutely licking your wounds wondering if it's the end of the world it was that was a big time i was running zillow yeah i was running zillow we we only we had to lay off 35 of the company after the you know it was a it was a financial crisis yeah yeah the gfc happened in the real estate industry with mortgages right and we were like the real estate industry let's be honest right and so we were money losing pre-revenue oh my god that was a were you public at the time no we were private but it was losing money really rough 150 people i think we had to layoff about 60 people it was it was rough that was one of the lower lower points yeah laying off people was that your first major layoff or had you done any of microsoft and xmedia i had you know i'd had experience with small scale ones but nothing like this uh your leg shake did you puke did you uh get the sweats i had to like i actually wrote about it jay cal i i i had to journal on it to dump all the awful awful feelings i had get him out onto paper and talk to people about it because it did rile me up i have to say you know i've had to do it since then and like it or not we do get desensitized to it um i'm very i really really believe you have to treat people with humanity on the way in and the way out and you want to leave the door wide open because a lot of times they come back when you do yeah uh and when we did have a lot of boomerangs you know that's what i call the people that come back those are those are the very best employees of the boomerangs by the way well and it also is indicative of great management i've had a number of them as well and the conversation is always very encouraging which is i've i frequently have people say you know i i really we had our battles but i really enjoyed working with you there was just something about the energy and the dynamic then you know the dynamic nature of it uh would love to work with you again i think that's like people don't know how good they had it you know on both sides you have some employees you don't appreciate when they're working for you and there are employees who don't appreciate you they get some great job offer and then they just come back 18 months later and like you know what this is home this is better right that's sometimes you gotta break up before you know you're in love right and then that that that happens a lot why do you think first-time founders yeah take it so hard that you gotta journal talk to a therapist whatever get some counseling over it just that it just hits you like a ton of bricks what was on that paper that you wrote a because we're human um you know and uh we care and we care about people more than we care about anything else and we care about socializing and our friends and support and giving more than we care about anything else most of us yeah and so it hurts and i and i also think we get this especially when we're young in our careers we get a little bit confused about our jobs and our families, our co-workers and our families.

19:28And it feel a lot of young startups that I've been a part of, that you've been a part of, I'm sure they do, it does feel like a family. Yes. And breaking up with your family is kind of the worst thing you can imagine, right? And so that's what it feels like. As you get later in your career, you come to realize that your work is actually not your family. Uh, that's not to say it doesn't have humanity in society. It does, but it is more like a professional sports team than it is a family or it should be. Okay. And, and we are here to do a job and play a game and win the game. And we want the very best players in each position because if we have a weak point guard, we're not going to be able to score, you know?

20:13And so I don't want to take that too far. If you take that to an extreme, you get to read Hastings at Netflix. you know he really really that's his that's his theory of hr and you know an interesting theory created a high performance culture but uh anybody who's in our industry knows at the end of the year you got netflix people who have to basically reapply for their job in january and if you've got kids if you've got friendship at work if you've got mortgage payments that's rattling and people want safety and i think he created an unsafe environment which is appealing to certain groups of people but it might be a little too cutthroat i wonder if he still holds that opinion now that they're successful at scale i don't know i well he does i've been i've been on that board for 21 years and still am actually so i'll give you a little context oh i didn't realize you were on the board yeah yeah i've been on the board since it was private jason so uh but um incredible company um and i've learned i'm a shareholder learned learned a ton and and you know i love it when people do things in extreme interesting and novel ways because then it begins to make you test all of your theories right and and anyway so reed has done that for me uh i'd say more than any other person um but he is now executive chairman he is no longer ceo the company is a lot bigger and the company operates in a highly creative enterprise where where the the most important thing they're doing is actually creating stories and content with creative people.

21:48Right. And so of course cultures evolve. I would say the foundations of reads performance oriented culture are there. Um, but it is evolved. It is absolutely evolving and evolving. Well, yeah. Yeah. Back to branding. Okay. By the way, I love the, I love, I love the sports team analogy, I think, because I was just, I get one of the things that comes up a lot is I, um, I watched the, what's the movie based on the Michael Lewis book on baseball? Moneyball. Moneyball. So I just got the Moneyball where Philip Seymour Hoffman, rest in peace. I mean, what an actor. Oh my God. He gets into an argument with Brad Pitt.

22:34He's like, yeah, you're not playing him on first base. He's like, oh, I'm playing him. The roster's mine. He's like, nope, you're not playing him tonight. He's like, I am playing him and that's that. and he's like you're not playing him because he doesn't work for our team anymore and he's trading him and he's just like you're killing me and it's just such a great scene but it's very hard sometimes to to make those decisions hey the team started and what got us here is not going to get us there you know this this player you know you see it all the time in product and finance and sales an organization gets to a certain scale that person just can't level up and they don't want to they're zero to one they're not you know one to a thousand in terms of employees right most of those conversations founders dread having that conversation but in my experience it's liberating for the folk the people you're having the conversation with as well it really it really is because everybody wants to you know achieve their highest and best use and really wants to contribute in a way that everybody believes they're contributing as well and getting the right people in the right places and letting them thrive that's just that's that's fantastic um anyway so back to the branding so back to branding yeah back to branding otherwise we risk burying that one again it's a fun it's a it's a fun blog post check it out if you're if you're from the from the from the show notes but basically i believe um first of all fundamentally i believe making up words if you're building a consumer brand especially okay a little bit different for b2b some of the same principles hold though if you're building a consumer brand making up a new word is better than taking a pre-existing word okay okay zappos is better than sneakers.com got it okay and the reason is but those of you out there are saying are saying oh but sneakers.com is going to get seo uh right away yeah so i don't need to work very hard and zappos who the hell knows what zappos means i'm gonna have to like tell people what zappos means okay that's absolutely right so making up a word is harder initially and more expensive initially but when you are successful making up a word you own the word you have defined the word you have filled that word with the emotions that you want to have it filled with that come from your product and then that word if it if you get lucky enough to get something like like zillow uh you get you you you've added to the vocabulary of humanity yes okay uber airbnb so many great examples yeah yeah so many great examples okay so so i really like the harder route which is make up a word and then own word whereas if you were sneakers.com you get really big you know it just there's no connectivity sneaker means something to people already all right amazon is an interesting counter example that existed already and had meaning but bezos took that word and completely redefined it yes i was about to bring that up like calm.com yeah is another example we're investors in that one but it's a meditation app it's an existing word it's a four-letter word it's in the dictionary it's evocative but meditation is not necessarily calm it's an output of calm uber exists as a word you know the top thing yeah but again you know and i think airbnb i remember talking to the founders early on they were considering just calling it air uh and i had this like big branding conversation with them and i love the concept of air uh and i i was like you should maybe do that i don't know you like airbnb or air i like airbnb way better because it's there like airbnb better okay yeah i don't like it syllables let's get to syllables okay syllables so i like making up words then once i once you make you decide you're going to make up a word here are things that i like i like high point scrabble letters okay what are those q z's xq's right they're high point for a reason why are they high point they don't exist there aren't that many words with them they're rare bingo they're rare okay so rare letters are memorable interesting rare letters jump off the page subconsciously if you could look at a screen of text the z's and the q's and the x's you see them you're the back of your the you you see them in your field of vision and you're processing them because they're rare everything else is that's not rare so i like high point scrub letters clearly elon musk does too x.com x x x x x uh i do like x's um uh expedia okay so you like high points high points probably letters okay second thing i learned i made a little bit of a mistake with expedia x b d uh x b d four syllables too many two too many many one too many two too many two too many two too many two is the right number two is the right number i think two is the right number two is the right number i think google yahoo facebook yep you got it b and b too many too many but still a good one because it's not bad yeah amazon amazon one too many one too many though okay though yeah so it doesn't have to take all the boxes i mean it's a framework it's a framework are you still using your personal phone number for your startup it's 2023 it's time to stop it is a huge mistake that founders make.

28:01Why? You're just getting started with your company and you don't think about phone numbers as being an important part of the IP collection of your startup. With open phone, you can totally solve this problem. They've rethought everything about a modern business phone and how it should work. It's super easy. You just download the app on your phone or your desktop and you pick a number and you're done. And you do it for just such a low price. It's so affordable. And think about it. If you have your sales team using their personal phone numbers, a salesperson leaves and goes to a competitor, you don't have any insight into what phone calls occurred, what people's phone numbers are, that's your company's database.

28:39And if you allow the sales team to run them up, or the customer support team, it's just unprofessional, be professional, use open phone. And we use it for things like event communication. So we get one phone number but it can go to multiple people like a round robin thing we have a shared phone number do that for customer support and open phone is rated number one on g2 for customer satisfaction and you know i trust g2's ratings open phone it's ready it's affordable starts at just 13 bucks a month but twist listeners can get 20 off any plan for the first six months at openphone.com twist and if you have existing numbers with another service no problem easy peasy lemon squeezy open phone will port them over at no cost head to openphone.com slash twist to start your free trial and get 20 off and then one other i like maybe it's in the blog post but um i like it if it would make a good dog's name oh uh uh just dogs dogs names are dogs names because they're memorable and people responding dogs respond to them which means something in our brains responds to them fascinating verbs if you can turn the word into a verb you know you've made it as a consumer brand when you become a verb or when you google it when you zillow something yes lawyers the lawyers will tell you oh don't never never let your brand name be used as a verb because you're going to dilute your brand you know defensibility whatever i'm like no don't listen to that go every conversation i have with lawyers about intellectual property fair use trademarks and copyrights is so fear-based yes it's the worst advice collectively the ip industrial complex gives fear-based advice yeah and it has no practicality like they told you probably do not do this estimate you're going to get sued i mean what was the glass door i mean you you ask an attorney to evaluate the zestimate or glass door ratings they're going to give you every reason not to do it yeah don't do it at all yeah don't do it don't do it it's just too risky founding of youtube don't do it founding of uber don't do it don't do it okay so so look i i believe that you can't be a successful start it's very hard to be a successful startup or a company without amazing attorneys i have high high high high respect i do believe that something that lots of organizations especially startups a trap they do fall into is that the attorneys are so well educated so smart so articulate they command the space so well yes people kind of get get get confused about who's working for who exactly this is exactly what happens when i have conversation with david sachs on all in he's an attorney people are like oh wow yeah no trump's not guilty i'm like are you sure are you like really i don't have no attorney but the hard way the woes of like trying to debate a debate champion i that that's what it feels like yeah it does you can't debate you can't it's such a good point you have to be able to say to an attorney what what do you say to an attorney when they're overpowering the room saying hey here's all the reasons that you're bending the rules and here's all the reasons you're going to get legal letters and sued how do you over your career how did you get more confident in managing attorneys who are trying to do the right thing but they don't want to get fired when you get sued so they always take the the most conservative path i guess the advice i'd give is to is to is to find attorneys to work at your company and to work outside your company who really are business people okay they're they're business peoples and attorneys together they're not just attorneys and when you when you when you find one and there are a lot of good ones who are business people you basically partner with the attorney to make a business decision of which the legal advice is one component okay and and trying to really assess the amount of risk and how much risk are you the entrepreneur or the business person willing to take from a legal perspective some of the great companies have been created in that that kind of okay it's not without risk but we're going to plow ahead and do it because you know what it's the right thing to do it's what consumers want and at the end of the day i'm psyched about standing in any courtroom and wrapping myself in the consumer flag saying i did the right thing i let the sun shine in and gave power to the people this is i think such an instructive point because watching what uber and airbnb did close up and investor in one and just you know knowing the other pretty well and even doordash and postmates you know a lot of what they provided to the world was not already defined by the rulebook and when you looked at when they did stuff to your point power to the people if somebody is using an Airbnb, DoorDash, or Uber, that is very empowering.

33:53If you live in Brooklyn and you couldn't get a cab, if you're living in Arizona and you're a retiree and you have no income and you can rent out your guest house, this empowered people in a major way. So when they did get resistance, they had an army of advocates who would say, yeah, we want Airbnb, we want Uber, we want DoorDash, we want Postmates. And so ultimately we'll win, even though the regulations are set up to protect the folks who are doing it the way it's done right now, be it the Taxi Commission in New York City, whatever neighborhood regs versus Airbnb. You know, we had our own with early's estimate.

34:30We had serious problems with the industry didn't want us in and they were trying to use the regulations to get us basically illegalized and kicked out of the industry. And I remember an amazing thing happened in Arizona where it got to the Arizona Congress was debating this. The real estate lobby had brought all this pressure to bear. And we had all these Arizona Congress people get up and say, you've got to be kidding. I love Zillow. Zillow is fantastic. It's helping me go away. And it just went away. But anyway, I'm not encouraging everybody to go break all the rules. You've got to pick the rules.

35:04pick the rules that you want to break based on what is the right thing for the consumer so a noble you know recontextualizing uh i'll use that framing of existing laws noble and i think this is where crypto um you know was so promising at the start but i found so abhorrent you know when all the hucksters came in they pitched it originally as this is going to empower people hey you're not going to be controlled by fiat currency you're not gonna have to pay all these fees and then i was like oh you're just sweeping all this cash off the table selling worthless tokens that don't solve any problem in the world and so this whole moral high ground that they had staked they never delivered on they never empowered anybody to understand the price of their home or get a better deal on a home or get a taxi in brooklyn yeah yeah i think i mean if there's a buck to be made it's going to be made and then there there was there was a lot of that there was a lot of that there i still hold out a lot of optimism around what emerges from the the crypto booyah bays that actually is a value and i think we'll probably begin to see that what do you think is the valuable part of it what intrigues you about it i mean i really do believe that having a digital store of value and a cross-border you know meta currency um that concept is a very powerful and strong one and it clearly is useful and you know because of that i think we're going to continue to see a lot of innovation here i i'm i'm really kind of confused though i mean we're in a little bit of a resurgence of meme stocks and resurgence of of of trash right now and yeah and I'm just like, in what world and what economy is this?

36:59Is this being supported? I, it's confusing to me that we're seeing that in a little bit distressing, but I think I guess I write it off simply as people like to play games, you know? I, you literally finished my thought in my brain. I'm like, I think there's a group of people who find going to a subreddit, debating a meme stock and trying to cause a squeeze or just getting in a battle with some big hedge fund. It's, it's entertainment. And then I think also buying crypto is entertainment for people. So it's like sports betting. And you and I are looking at it as investment and securities and structures and alignment.

37:37And that makes it perplexing. Just like some people will look at a professional poker player and be like, they're playing a game for a living? I don't understand. And it's like, no, they have a strategy here. They're making a million dollars a year playing poker. It's actually, you can do both things, right? Yeah. All right. You know, I've been on a health kick over the past year. And you know, I care about data driven solutions. And if you listen to this podcast, I bet you do too. So let me tell you about FitBot. This is a data driven workout app that blends machine learning with exercise science.

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40:46I've been in the industry now 17 or 18 years with Zillow and I will tell you that our real estate industry here in the US is by far the cleanest, most liquid game in the world. Most real estate markets around the world have almost zero transparency, no clearing house marketplace where you can actually see all the inventory. Not a lot of places have buyer's representation so i guess i would say i you've learned to appreciate it i've learned to appreciate it and understand of course there are there are lots of pockets of information to be liberated and lots of efficiencies to be gained and a lot of ways we can make the interactions between buyer seller and our partners better tons and tons and that is the space we live in but i didn't want to just let you let you throw out the it's a cartel but well here's yeah tell me like how did they try to stop you how to how did you make them you know peace with them or you know and any yeah any industry that's been around for a long time wants to hold on to the marketplace information okay you can pick your industry name your industry and you find a set of of of legacy players who have a control of the marketplace information and and they don't want to release that for for obvious reasons but gravity tech internet smartphone says there's no way you can hold on to that information that information does eventually want to be free and and the opportunity we saw was zillow was being able to kind of tear down that wall liberate that information add a bunch of more information onto it and create a much brighter lit better operating marketplace That is what drew us to it.

42:31I would tell you that because of Expedia, the travel industry really didn't like us. And I have had a lot of experience with the, let's call it the supply side of the marketplaces that I've been building, not wanting me to be there. Okay. And actively disliking it, disliking what I was doing. But I always felt, I'm holding my hands up here. I've got the supply side of the marketplace egg. here's the marketplace the supply side on one side and the demand side on the other so consumers over here on the other side i've always felt that it's most important to engage the demand side and that nobody on the supply side is going to show up unless you have you're doing real magic tricks for the folks on the on the demand side and no one's even going to take your calls and care that you exist unless you have the demand side but if you do in fact show up with the demand side and you have engagement with the demand side of the marketplace, eventually the supply side is going to come around to dealing with you.

43:28That's kind of been my philosophy. Of course, both sides of the marketplace matter hugely to make a marketplace. You can't have it without both sides. But I've always believed that if a product manager is working on features and is trying to decide, should I do the right thing for the consumer or do the right thing for the supplier? Well, number one is the consumer. Number two is the supplier. That's what I thought. Of course, if you don't have happy consumers who like your mousetrap, you have nothing. And I got to see this up close and personal, but some people believe the supply side is the hard part of a marketplace.

44:04So what do they, why do people fall for that fallacy that, oh, if I just had the supply, then everything would work out? You know, I think we could probably pick examples where that has been true, especially for highly concentrated supply side industries, which there are plenty of where you don't have too many competitors. There's there's there's airlines. We fall into that. There you go. High degree of control. Yeah. And so, however, if it is if it is highly fragmented supply side. Hotels. Hotels is perfect. then then um and you have a lot of choice so it's it's to a certain extent somewhat commoditized in that it's replaceable or interchangeable or you're able you'll you're able to steer traffic one way or another then you actually begin to uh focus more on the customer side in any marketplace you have to have both i don't want to say that you know you really have to have both and and by By the way, it could be a fantastic consumer experience to have exclusive supply.

45:10Okay. You can only find Stranger Things on Netflix. That is a really good consumer experience. Okay. Yes. So it's, I, I, I'm nuancing a bit what I said. Yeah. But in general, I believe, I believe at least in the companies that I love and that I've been a part of, uh, that the consumer is your North star. Yeah. that is that is what we should and by the way that's the most fun to me anyway so yeah i mean if you can delight a consumer uh you're going to have them use the product again and using the product again or telling your friend about the product and why you love it are the two most powerful things in consumer land would you say absolutely absolutely yeah we we were working on word of mouth stuff before there was social media before there was smartphone you know yeah um zillow the zestimate predated the smartphone yeah okay and predated social media there was no social media at that point and so word of mouth was like standing on the on the sidelines of the the kids soccer game and talking to each other it was oh we call it over the shoulder uh david sax came up with that one uh two sax references one episode but he was talking about uber and we i had invested in and then he invested in a later round and we were talking about it he said this thing is so viral i'm like how is it viral the the give to get like the 25 she's like no when when i order an uber and i take somebody they ask me if i have a driver and i say no i have uber and then they say what's uber and then i take out my phone and i show them to them and i was like ah it's like over the shoulder and he's like yeah it's like over the shoulder virality yeah i'm like um we've all had that moment where somebody takes out a phone and does something magical on their phone and you're like what did you how did you do perform alchemy and magic wait show me that show me that what is that and it's like apps or spells right just like here's something amazing um be a wizard i love i love that analogy be a wizard yeah well i mean if you can conjure up something that delights a consumer that is magic right and it just it's so rare that you know it when you see it right you just yeah it is you gotta think what does it take to make magic and you really have to find magicians and it's something that i mean i was i was kind of i I grew up at Microsoft in the early 90s, right out of college.

47:31And there weren't many tech people there. What was your first job there? I was product manager of MS-DOS 5. Really? Not many of your listeners. I mean, I was on MS-DOS, but I think I went to Windows Runtime 3.0, and then DOS 5.0 still exists. It was like parallel. We did do it parallel for a while. You had to actually put the Windows on top of DOS. Yeah, exactly. And DOS 5 was the first time we did a retail upgrade of the OS. Until then, you had to basically wipe everything off your computer and then install the new operating system and then rebuild all your apps and all your data and everything, right?

48:10It's crazy. And so the idea with DOS 5, Bill Gates' idea, was, hey, could we write a little program that lifted up all your apps and data, swapped out the OS, and then set them back gently down? and you're like that's insane and now we have over the air updates and they occur without us even knowing what was insane about that was the software was sold in packages then we didn't have the internet right so so it was the most popular software uh skew sold of all time by a factor of 10 das and windows 5 upgrade literally egghead we did a midnight mad egghead did a midnight madness sale we had people camped out to get waiting to get the dash five upgrade and it was like there were like five bullet points on the back of people forget this but the way you um interacted with software was you went to comp usa or fries or whatever store and um there were like vhs tapes at blockbuster package you could you could go buy netscape you would go buy a browser for 99 you go buy a video game you go buy the operating system when the operating systems came amount it was a bfd it was a big deal in nerd land oh yeah so you were going to say about what you learned at microsoft that was an interesting time the 90s was when they were firing on all cylinders and they were about to peak and get their knuckles wrapped by the antitrust department which would be a great jumping off point for a lot of discussion what was what was amazing to me at that i had studied engineering in college but i wasn't practicing engineering at at microsoft but I was dangerous enough that I could hang with those folks.

49:50Right. And it totally felt like we knew magic. We were, we were wizards and the rest of the world was full of muggles and, you know, let's make some spells and change the world. I mean, it was really a magical, a magical time. And honestly, I feel that way today. There are a lot more people that are involved in tech now and a lot more engineers and a lot more product people in design. and marketers that are so fantastic. But in general, it's still a pretty small segment of really special creators of products, okay? Of technology products. And if you can find those people, I'm talking to the folks out there, just find those people and take any job you can get to hang around with those people.

50:43What do those people have in common? If we look at the people who have that alchemy, that ability to cast a spell, what are the attributes you see? Obviously, Gates and Jobs, Elon, Jack doing Square and Twitter. I mean, there's a lot of interesting people in that. I wouldn't put Zuckerberg in there because he just copied everybody's stuff. I would put Evan Spiegel in there for sure. You got to put Reed Hastings in there. What do those people all have in common, the conjurers? you know i was i was just listening to the names as you were throwing them out um because i didn't really i don't really have a pad answer to your question so i was looking for patterns and i guess i would say uh i was i was steeped in that environment on microsoft so i absorbed it by osmosis but i guess listening to that list i would say it's the people who love products and you know the people who love products because as they move through the physical world or the virtual world with you and you watch them they are continually frustrated by bad products and bad design you know like crestron home interfaces for managing your lights and music okay like like equestron oh i hate to say this but these big soft controls in the cars now with these giant screens look god the knob worked better okay it was better my light switch works better than this panel of bull you know and seven clicks to get to something right okay so you know those people in your life and maybe you're one of those people okay but in fact i think those are the people that you want to hang around with yeah those are the people you want to those people are the ones who are going to invent the future breakthrough products i think you know one thing i think with those folks you know investing in them for a living now is they're very um what's the word when i don't say cantankerous but they're very annoyed when things should work better and they don't they're uh what's the word they're not insufferable but they're in they're not they're intolerant of product yep and they're frustrated and they're tenacious and they're tenacious and they're critical and sometimes they're not um um the most tactful in their sharing of feedback gates was the penultimate i mean and and he or the ultimate i mean he was known for savaging people tell me about gates in that period because he was at the height of his powers in the 90s yeah when i started 90 of desktops were microsoft's at the time to give people context yeah when i started at microsoft in 91 we had maybe 3 000 people at the company so not small but certainly not big barely barely medium medium sized and and bill gates at that time was uh the company was still on the scale where he knew everything about every product company and was running product reviews continuously through his conference room.

54:00And so every product team at the company would cycle through every six months, every six to 12 months and present what they were working on, the progress they were making, et cetera. And it was mostly kind of product management, engineering, little program management, not a lot of sales and marketing, but sometimes. And Bill had a kind of earned reputation for being incredibly difficult just steve jobs had the same kind of reputation as well for just being incredibly critical and difficult and hard uh on folks i learned a lot about how great product people think but i also learned a lot at the time about about how how i deliberately tried to create cultures that were able to be critical but also simultaneously respectful and i would say bill has learned that in his in his lifetime as well so why do you think at that period of time the you know let's say no a-hole rule didn't really exist and it was actually a bit more of a pirate ship and you could kind of get away with that or that was the culture which was i don't care if you're gonna cry and if i can make you cry when i give you this feedback great because i need to get you the off the ship because there can be no cry babies here and if you don't want to come in and work this weekend 12 hours to fix this i'm you're walking the plank that was to give people historical culture the 80s and 90s tech was pirate ships fighting in the open ocean and if you were on that ship and you complained you walked the plank period full stop correct it was pretty rough you know it was a culture that you and i probably were well-suited let's say that okay why was it like that and what was it it was it was a bunch of dudes it was a bunch of young dudes yes okay so it's really smart 20 we're all we you know bill was 18 when he started microsoft okay people forget my co-founder at zillow lloyd frank started working for microsoft at the age of 14 years old when there were 22 people because he went to the same high school bill gates went to and his mom his mom and bill gates mom were friends and they they were at some school function at in seattle and and and and you know bill's mom said to lloyd's mom my son's really into computers and lloyd's mom said so is mine like we should get them together anyway it was a bunch of dudes uh and they were young and they were smart and that particular mix of folks created this pirate culture that that you're that you're talking about of course that culture grew up those people grew up and you know we've recognized that to harness the maximum amount of power we can in this space being way more inclusive about the the group of creators that we bring into the space meant that there had to be a different culture and so we have all maybe not all you know there may be some organizations that still operate this way but not mine yeah you know so and do you think the culture got too soft during the google you know we're going to do your dry cleaning and here's your infinity pool and hey 20 of the time do whatever you want or if you want to do nothing and just hang out on the roof and rest invest at hooli you can and then we're now cleaning a bit of that up so do we pendulum go too far the other way and entitle create a little bit of entitlement culture i mean i i think broadly speaking in you You know, in the industry, I think it's a keen observation.

57:34It's not how I've thought about my companies, though, J. Cal. I do believe that that culture is a symptom of simply not having really cool, important stuff to work on. Too much success on the original idea, maybe? Maybe too much success or just like you're not now doing cool things that fire you up. I believe when you're on a mission to build something amazing and you're making progress and you're working with your team, I believe what people really want is to work on cool stuff with great people and win. That's what I think. Winning does change everything. I mean, even if the culture is a little bit off, if you win, people are like, yeah, Draymond punched somebody, but we won, right?

58:25so if they won this year and draymond punched somebody who cares it's only like you know when you don't win and it the things were chaotic that you're like i mean we need to evaluate here how do what is the culture you try to breed knowing what you know about entitlement culture you know on one side and then pirate culture maybe being a little too rough and tumble for you know today's environment where did what culture did you define for your companies I would put a third leg on that triangle and basically say, oh, look, have a real kind of mission-driven company that's building something that matters to people that we can talk to our moms and sisters and brothers about and SOs about and that gets them really fired up.

59:16have it be some have a goal that is a big hairy audacious goal that seems super important you know to to people uh and then assemble a really diverse team of adventurers to go summit that particular mountain you know that's mount rainier in in seattle you know in fact probably it's over my shoulder on my background yeah amazing that's this is my actual office so it's a virtual version because i'm on the i'm on the red uh but uh you know rainier is the destination we want to stand on top of rainier that's what we want to do let's go do that yes and and in order to get there and make it through the storm and the hail and the lightning and the river we got across to get to the base of the mountain and and whatever we have to have a really great team that respects each other and respects every component of it not just not just the leader you know not just the engineer you know not just the storyteller like we need we need everybody we need the whole wheel and all the spokes tightened to make the wheel roll and so yeah the kind of culture that i like is a culture of respect and inclusivity but hardcore adventures you know trying to summit the mountain yeah and the purpose that makes everything kind of lock into place because people understand hey this is the mission and then you know here's our strategies here's our tactics whatever you know you can get granular on it but at least if everybody knows the mission of where you're headed it gets easier yeah it gets easier and you get through the dark times because there are times when you can't see the mountain and you know if you don't really have a clear picture of where of where the mountain is what it's going to feel like to be there then you get lost in the dark, right?

1:01:00You get, you get lost in the storm. So, um, that's what leadership, you know, that's what leadership is. And for the leaders out there, you know, painting a picture of the, the, the wonderful future and the destination and, and communicating that in a compelling way that gets people fired up. That's what serves you in recruiting. That's what serves you in building great products. That's what serves you well in, in signing up, uh, partners and suppliers uh that's what gets you there you know this uh covet thing was quite an interesting catalyst and also um you know headwind for different businesses airbnb i had brian chesky and joe jebbia on recent this year and uh they both said this is like you know crucible moment as ruloff both would say from sequoia crucible moment for the company and there's a bit of a crucible moment for you as well uh at zillow um this covid sorry i got distracted yeah covid yeah it's crazy and that moment in time and then everybody going remote this had massive impact on your running of the business some of the business lines you were in like uh flipping homes or being an ibuyer i think is a term you use for it in your industry yeah and then you know brokers not being able to show houses i mean talk about the chaos of the last three or four years and this work from home trend which impacts your business because everybody wants to buy a bigger home but also impacts your ability to run a company so walk me through like the last couple of years in coming out of this covid shock to the system because i don't think we ever experienced anything like it great financial crisis felt like a cakewalk compared to this in some ways i think it's been the most important and interesting and complicated and fraught and and quite actually wonderful in a way you know it's weird weirdly experience in our in my lifetime you know in my business lifetime our personal lifetime everything it will be the thing that defines our generation i think this is we're gonna be i thought it would be 9-11 but it's like because i think it's covid because 9-11 was you know contained in in some places but so yeah so so all the trends all the trends that you oh yeah all the trends that you talked about you know dead bang on i mean i think it's trite to say at the time but you know it's right to say now but really covid what it did was accelerate by n years five years or more a lot of the kind of pre-existing trends and name your industry name your political movement name your whatever and covid had a way of just breaking through a lot of the legacy crap that was holding back progress on these trends yeah okay uh um and in that That way, it's like one of the most innovative times we've seen, right?

1:03:45You know, we all used, we had Zoom at the company, we had Slack at the company, but they weren't very well used, right? And then all of a sudden, bang, they became the two most important things happening at the company. Everybody's got a podcast studio now in their house or office, right? They got a professional mic and a great camera and lighting. We already were tending towards more hybrid work and much more nomadic work. and boom, this like blasted that one out of the field. Telemedicine. Yeah, we already were moving towards telemedicine. We were already moving towards digital routing of mortgage documents, but we hadn't gotten there, but boom, now we got to because we can't meet.

1:04:24So all of these preexisting things just got blasted forward. It was a huge, initially in the real estate market, it was a huge wind at the back for transactions because everybody wanted to move and so we saw a huge amount of demand pickup to move and so zillow as a business experience this incredible you know it wasn't quite like zoom and peloton but it was kind of you know in that uh in that same vein because so many people wanted to move and and then of course you do you know we we get the rebound from that and we're seeing that interestingly if you looked at the plot of zillow unique users on google trends or something over that time you wouldn't actually see too much um which is sort of interesting but it did change the behavior of moving itself it kind of front-loaded some transactions and now we're dealing we're dealing with the with the echo another aspect of it was you know this well but capital was free i mean you know yeah interest rates were basically zero and you know capital startups were and big companies alike were swimming in capital and so we had yeah we unlike anything we've seen you know we thought we saw it in 99 we thought we saw the the the most euphoria you could possibly see and that was nothing compared to what we saw in the zero interest rate period right people would just offer you they would come to a company like yours and say hey here's money how can you put it to use where you have money to put in your bank account and you can pay us back at two percent or even personally they're just oh you have a bunch of stock here here's some line of credit that is unbelievably low and people are like yeah i should just buy the stock market with this and yeah i mean people got themselves in trouble with leverage but right so it was crazy so a bunch of a bunch of new businesses emerged where capital availability was the the defining competitive characteristic right so you know the ability to raise an infinite amount amount of money at a very cheap price hatched new business ideas as a result.

1:06:37And so we saw a lot of that in the market. And one of those ideas was kind of trying to flip homes at scale and provide a more efficient marketplace, this iBind concept pioneered by Opendoor, who's a partner of ours now. And at Zillow, this was one of the things where we're like, all right, well, we can raise the capital too. This might be super important. Consumers seem to really like it if we can get it to big scale we should give it a shot what the concept of i buying is what was the thing that attracted you to it what was the thing that made it appealing to people just a less hassle and moving like you know it's very it's very hard to coordinate the buy and the sell when you're moving uh from one house to the other if you're a first-time buyer this is not no problem okay other than affordability um but uh if you're selling a house and buying a new house the problem of managing all the logistics between those two things and not being able to carry two mortgages it makes it difficult and so if there is a market maker that sits in the middle that could temporarily own the house fix it up and then sell it and you could you could get your money and then get on to your next house well that that makes a that that that is has some consumer appeal to it um the problem we encountered however was that prices turned in covet especially prices turned out to be way more volatile than we ever anticipated they could be which made the calculation for market making and holding inventory become much more dangerous and risky and so you know we tried it for a while decided yeah we're software people we're not big capital big balance sheet people we're going to stop doing that and we're going to partner with the innovator in the space open door to do it and that's and you gave them your is that what you did you guys did a deal to give your inventory to kind of work it out as it were?

1:08:25No, we didn't, we didn't, we didn't do the inventory deal with them. We simply did a partnership with them on a go forward basis. We, we had no problem. We, we made this call in a November of 2021. So before the interest rate thing happened, I just got nervous. And so before interest rates went up and made everything look horrible in the whole world, we were in, and houses, it was super easy to sell a house we were able to unload all of our inventory before before this i took a lot of crap i took a lot of crap for this at the time you know from my people too and it involved a lot of layoffs and it was rough um but we as a leadership team looked pretty smart pretty shortly after that uh because we had we had gotten out of the business so anyway but owning this is a lesson in learning yeah owning thousands of homes requires you to be able to have unpredictable swings being a publicly traded company that's not great for running a public company if you're some private equity firm or some giant hedge fund it's a lot easier to own a thousand homes two thousand homes if you're only you know if you're looking at it with a longer window and you're not doing public quarterly earnings calls correct correct and especially if you're a software person who's used to you know 93 gross margins which is how i grew up you know and and and dealing with four percent gross margins um you just you just have to be really good uh uh way way better than i am jay cal so so like people say this like i i i don't know if was warren buffett or something he was talking about how hard it is to compete in like uh two three star hotels that you know the holiday inns whatever and it's like there are specific indian families cartels basically who are so good at operating these things that nobody can operate them better than this group and these families that own those hotels and you shouldn't even try operating right like why would you bother like it's just too too hard right when we look at what's happening in the market high interest rates maybe staying high for longer than people think what impact is that having on the markets especially after all of these covid towns bumped and then we'll get into are people going to come back to offices because we were looking at maybe moving to austin i was pretty public about it we're considering it yeah uh and this the house is like tripled in price and i'm like wait how is how are you getting 20 how are you asking 2 ,500 a square foot when that's the price in atherton that doesn't make any sense and right so and there's no you don't record the prices in texas so you can't even do an analysis of what's happening and i was like i'll just wait for this all to calm down now it turns out some those places are collapsing right so maybe you can just tell us like what's happening post all this movement and then is the market frozen with these six seven percent mortgages or is it possible that society can deal with the six or seven percent mortgage rate yeah it's logical that some of those you know zoom zoom towns i guess they were called at the time yeah you know salt lake city bozeman austin um you know the hamptons uh wherever you know they uh are definitely experiencing a a pullback truth be told though none of those places is very big and couldn't absorb that many people anyway and so they were in they made for interesting headlines but that is really not the big story the bigger story in people movement i called it the great reshuffling at the time in people movement catalyzed by covid is um not necessarily people moving completely out of the city to a brand new city in a mountainous state or what have you it's actually people moving into the donuts around cities so the ring the thick the thick ring of places around cities is what has really been enjoying it it has the capacity to absorb a lot of of movers uh and it's like stimulated a real boom in these donuts around cities to the detriment of the downtowns which is you know which is what's been we're trying to recover from right now and and that's interesting and that makes a lot of sense people who are working two or three days a week going into the office that can commute at the times they choose that what they want to they want to move to a place that has a yard maybe a little bit different school where they can walk the dog whatever and that's that's really been the predominant trend so now what we're looking for and a lot of people are watching very carefully especially if you're in the commercial real estate business that has investments in office towers in downtowns you're trying to figure out what the heck's going to happen with all that space um anyway so that's that's kind of the big story what do you think happens do you think people go back to offices what are you doing at your company or are those going to have to get converted oh it doesn't look good for them jacal so it does not look good right it does not look good uh explain uh i think it's way worse than it even looks in the data that you see because you know uh the utilization rates the kind of what's being rented out right now in these offices pick your city is kind of in the 85 percent range right now which is galactically low numbers but if you actually look at usage it's way below that and then you start thinking all right what are employers going to do you're not going to rent space for like the wednesday when everybody's in you're not going to like rent for peak loading you're going to actually figure out how to optimize how much space you use so that you when on the peak days you're not going to be able to take everybody but you're also not going to be empty on friday and monday anyway it's a really really uh tough problem for the hybrid issue is very real because yeah yeah you're you're looking at it i'm assuming you're going hybrid is that your philosophy going forward or do you believe in um or do you believe like you need to get people back to an office to really do your best work and what do you candidly believe i'll come i'll come to that in a sec but i think the answer i think the answer my intuition the answer about what's going to what a new city is going to look like is we have to rethink cities to the point where we are intermingling life, shopping, entertainment, and work.

1:14:52The places that have intermingled those beautifully are thriving. The ones who have hived off high-rise downtowns and that's where your office work happens. And then over here is where the living happens. And then over here is where the shopping happens that is an unsustainable model people what people want is an intermingled live work shop eat play that's what they want anyway so i i think that's how it's going to going to play out with zillow i saw the writing on the wall really early july of june july of 2020 so first year of the pandemic um i was like oh my god we're working really well together in the cloud uh this definitely and obviously feels like the future to me uh let's burn the ships and let's liberate let's liberate people and then if you were living in new york city but your rent was your lease was coming up i said go ahead and move back to ohio be near your parents no problem uh we'll never ask you we'll never make it a job requirement that you move back to new york city and so we basically went to what i call cloud hq early on not without its problems but oh my god i'm so thankful that we didn't have to do this hokey pokey negotiation between management and employees that's going on it's so many companies right now amazon two face one yeah everybody is everybody well i mean there is some amount of abuse that is occurring there is a lack of mentorship for young people and you know there's some amount of collisions i've heard you talk about this before in interviews that occurs by being in person so what have you lost that you lament by having the cloud hq but what have you lost and that you're struggling to recreate i mean i think the early career mentorship thing is a real issue um And our solution may be that we just do less of that.

1:16:51You know, we have more experienced people. It could be that we'll see. You know, the collision in the hallways thing is real, but we're getting all kinds of more collisions in Slack and Zoom as well. If you're using those tools correctly or Teams, you know, if you're using those tools correctly, there's a new kind of meeting format where I've got Slack. I've got Slack up and Chrissy's telling me, you know, your time is getting tight. You know, we're multitasking and making decisions in meetings, right? Which has never happened before. Like we had to have the meeting after the meeting to make the decision because you couldn't say what you're really thinking in the meeting.

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1:17:29But now we can do it in Slack and just say, this is the answer and everybody moves on. So there's some more efficiency that's occurring because of this. Way, way, way more, way more. We still get together though. So CloudHQ for me means, yeah, you can decide, you can choose in these three time zones where you live, no problem whatsoever. But you are going to be, for a lot of job types at least, you are going to be required to get together at least once a quarter with your team. Once a quarter for a week. And you got to, yeah, so if you got a family, if you got kids, whatever, you got to make that work.

1:18:01That's part of the deal. That's part of the deal. And people have a blast and it's like the human thing and you get to know people and you make the human bonds. And then when you go back into your cloud HQ seat, you have more personal relationships and you're more effective. So that's working extremely well. You need 25 % of the office space that you had. I think that'll be right. Yeah. Yeah. We're at 35 % now. We'll probably get down to 15 or 20 % of pre-pandemic space. See, this is the fascinating part that it is worse because I know that the statistics you're talking about are correct. the the vacancy rate in uh san francisco i think it's like 30 which is absurd right like 30 is crazy you said 15 is crazy san francisco is 30 but i know that other 70 is being used 15 that's right let's say give it let's give it 30 oh my god unsustainable i mean it's empty down there is truly uh truly scary all right listen i know you gotta go you gave me a full 75 minutes i appreciate it i was really concerned with this because i told you at one point like i'd invited you so many times and i was just like you were like did i say something mean to you i insulted a lot of people and i didn't know i'm not good like that i was like this happened now three times i was like i told brian chesky at some point i was like brian i've invited you on like seven times i really am going to stop inviting you because i feel like i offended you at some point and i really don't want to make it uncomfortable and i said the same thing to you and you're like, Jake, I love you.

1:19:32I didn't do it. I'm like, so let's do a pod. It's not the end of the world. And you're just like, I'm not my thing. Honestly, it was, I don't like to get overexposed, but, but, uh, it was really Gerstner. I'm really tight with Gerstner, your bestie Gerstner. Oh, thank you. You know, watching, watching all you guys have so much fun on the all in, as well as how you're doing with this pod. Yeah. It's like, all right, you know, obviously. I appreciate you caving. Well, here's the thing. There's, you and i have been so blessed right to be part of a generation that grew up with the pc build companies to invest in companies be on the board of companies it's just such an amazing privilege and these conversations i have 16 17 18 year olds that 14 year old who went to work at microsoft they listen to this week and startups they take notes they write me these long emails i saw this interview it changed my life they come up to me i've had people hug me and cry and say i watched this episode with travis and you guys talked for three hours or i saw this chris sock episode and it changed their lives and that's the what gets me stoked everything about a mission if i can share these conversations with quarter million half million people and it just inspires 10 of them to create something in the world man what a legacy and just how great it is and you were so awesome let's put it on the books for a year from now uh really appreciate you taking the time i got a thousand more questions there it is folks we save it for next time thanks jake thanks everybody rich barton all right see ya cheers now Thank you.

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Today’s show:

Rich Barton joins Jason to give a masterclass on his thought process behind creating evocative top-tier brands like Zillow, Expedia, and Glassdoor. (22:02) Rich also discusses the lessons he learned from Bill Gates during his time at Microsoft (49:22), how tech management has evolved (57:04), and more!

Rich's blog on branding: https://www.hopperanddropper.com/syllables-scrabble-letters-and-picking-brand-names

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Time stamps:

(0:00) Zillow CEO Rich Barton joins Jason

(1:58) The creation of Zillow’s Zestimate

(7:03) “Tension and Importance” and empowering people in the workplace

(13:24) Crowdbotics - Get a free scoping session for your next big app idea at crowdbotics.com/twist

(14:53) Branding and creating iconic company names

(16:53) Navigating major layoffs

(22:02) Back to building top-tier brands, “What got us here, won’t get us there”

(27:54) OpenPhone - Get 20% off your first six months at https://openphone.com/twist

(29:25) Steering the complex dynamics of startup-attorney interactions

(33:22) Defying convention to create stellar products and the effects digital currency

(37:54) Fitbod - Get 25% off at https://fitbod.me/twist

(39:23) Innovating in the real estate industry

(49:22) Lessons Rich learned from Bill Gates during his time at Microsoft

(57:04) How tech management has evolved

(1:01:27) How Covid-19 and remote work changed the landscape

(1:07:02) The concept of “iBuying”

(1:10:31) Continuous high-interest rates, “zoom towns”, and the “great reshuffling”

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Follow Rich: https://twitter.com/Rich_Barton

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