#806: How Rich Barton Built Expedia and Zillow from $0 to $35B — Audacious Goals, Provocation Marketing, Scrabble for Naming, and Powerful Daily Rituals

0:00 Hello, boys and girls, ladies and germs, this is Tim Ferris. Welcome to another episode of the Tim Ferris Show, where it is my job to deconstruct world class performers, people who are arguably the best at what they do. How do they do it? What are their influences, favorite books, frameworks? Lessons learned, things that you can apply to your own life. And I have someone you may not have heard speak before. On the podcast today, Rich Barton. Close friend of Chris Saka and some other guests we've had. He is the co founder and co executive chairman of Zillow, a company transforming how people buy, sell, rent, and finance homes. Before Zillow

0:38 Rich founded Expedia within Microsoft in nineteen ninety-four and successfully spun the company off as a public company in nineteen ninety nine. He served as president, CEO, and board director of Expedia, and later co-founded and served as non-executive chairman of Glassdoor. He has done so many different companies. And he has a lot of stories from the trenches, a lot that you can use that is tactical and practical. He's also super fit, super active. I would say a great father and husband. He is an incredible human being. Sort of full stack. And that's part of the reason I really wanted to have him on the show. We did it in person, we covered a lot of ground. And I think you're gonna enjoy it.

1:20 I loved it. So With just a few words from the people who make this podcast possible, we'll get straight to the meat and potatoes and a wide ranging conversation with None other than Rich. Martin.

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4:54 Tim. And disclosure, I am a client of Crescent. There are no material conflicts other than this paid testimonial, and of course, all investing involves risk, including loss of principle. So do your due diligence. Optimal minimal. At this altitude, I can run flat out for a half mile before my hands start shaking. And then I also do personal questions. No, it's so. My cybernetic organism, living tissue over metal enough scale.

5:30 I know A D Q a little bit, he's a friend. And there was a point at which You know, I like to observe magic product things. Yeah. Of course Apple has tons. But my typical morning news setup is I'm kinda doing my email and sifting through things while I drink my coffee.

5:46 And I've got my iPad set up next to it, rolling, you know, C N B C Qui. On mute. And at one point a couple of years ago I mouse off the left edge of the screen and it seamlessly went onto the and my also my mouse is on the iPad. I was like Oh my God. It just decided because it was the same guy logged in, it's an extended monitor. Yeah. And I text him immediately. I'm like, Oh, Eddie. Why do you have

6:16 C and B C Playing concurrently. Is that just old habits die hard, or is it let's see if anything cataclysmic or monumental has happened that I need to be aware of? It's my favorite source of news because business news is generally Happy Yeah, got it. Just don't wallow in the bullshit.

6:36 Yeah. And regular news makes me feel bad. Yeah. And CNBC. At best makes me feel good and most of the time is just mid That's fine. You know, and I get the news.

6:49 I'm interested in business and companies and strategy and trends and you know, it is Pretty funny channel. It kinda gets on repeat. You don't need to watch it very long. But they get good interviews too, so I usually don't have the volume on I have the Close caption scrolling. Uhhuh. And then if something catches my eye, I'm gonna go do it. So let's take a closer look then at the other screen. Yeah. Yeah, coffee.

7:11 Yeah. Yeah. Yeah, I'm a pretty early riser. Mm-hmm. Six thirty I get up usually. And long before Sarah. Mm-hmm. My wife.

7:20 And so these Hour and a half, two hours I get in the morning are nice. My kids have all left the house now. There was a routine when my kids were in the house It was obviously very different and really fun. I can talk about that. But now I have two hours of

7:39 Just catch up on the stuff in my newsfeed, which is my inbox, my email inbox. I'm kinda old school that way. And as I go through that, I'm catching on the news on my iPad. I have a smoothie every morning with lots of stuff. What's the stuff? No supplement kinds of things.

7:56 But lots of cat testicles. I am not I am not one of those guys. I am I am not one of the the you know longevity supplement. people, but I'll tell you what's in it. It's about Three or four ounces of oat milk.

8:12 Ice An apple used to be a banana I've switched to kinda Two thirds of an apple. Pistachias. Macadamia's

8:22 A handful of blueberries. My favorite electrolyte. I'm getting ready for my work out. It's not very big. Mm-hmm. Electrolytes Prokari sweat.

8:31 Yeah, the blue the blue can, man. I had a lot of that when I lived there as a student. My nutritionist says that's the one. Yeah. And I'm like, okay, I'd been ha taking another one, using another one. She's like, no, this is the one. Not much. A prune? Prune. Prune.

8:47 Because keeps things moving. Keeps things moving, that's very important. You know, young people out there don't really realize how important that is yet. Yeah. But as you age you realize how that can affect your day. Really. Having everything moving. Here's a little hack. I'm not really a hacky guy, but I do have a lot of Well quirks, I guess. Hyper ice, you know that company that makes the Okay. They have a thing. I think they bought a bunch of products, but there's a back one called the Venom.

9:13 Uh-huh. You must have run into that. I think it heats and vibrates. Yes. Yeah. So I actually for my whole kind of forty-five minutes of that routine at the kitchen table, you know, with a lot of light coming in as soon as the sun's up. I have it on repeat. I'm wearing that venom. Oh my God. And you mentioned before your workout, so this is all

9:36 Pre workout. Yeah, I need to get things going. And feel settled. A little bit settled and brain on. Before I work out. Mm-hmm.

9:47 Coffee helps too. Coffee helps all that. Yep. And I don't drink a lot of coffee. Today I had a little too much, uh, because I'm off time zone a little bit, but I'll have one, maybe two cups. And that'll be the caffeine for the day. Yeah, got it. So I go through that and once everything's you know Make my ablutions and uh uh change into my into my workout. And pretty much every day I do a workout. I can't really get my mind right without that. All right. So we're gonna talk about the workout for people who are audio only.

10:18 This guy looks like a I don't know why you and Marvel character meets Abercrombie and Fitch model. Not to mention scion of business. It's unfair. Uh I don't know how I got the shirts drawn this genetic and habit lottery, but We're gonna talk about the training because I have this Working.

10:37 Pet theory that Longevity may be inversely correlated with the number of things that you do for longevity. Like in other words, there are a few things that really matter, but then there's a long tail. of things of questionable value that also have unknown uncharted side effects. Yeah. Plus plus.

11:00 At your body. The likelihood of you heading in the wrong direction is probably higher or just as high. My observation is the harder you push against something, the harder it pushes back. And I think the people who are pushing really hard at the longevity and And the supplement thing and the

11:18 The whole day scheduled out, lifestyle, things to improve, health span. Yeah, most of that's probably not. Yeah. Yeah, there's some basics. Yeah, and maybe the most important basic is When I was younger my kids were in the house because I got up early I was to get the kids to school.

11:33 Mm-hmm. Yeah. While Sarah became more beautiful. She stays up late. And I love to cook.

11:40 I've had several jobs as a kid growing up where I was a short order chef and Worked in a lot of kitchens and I love to cook. And so our house is set up We have a kitchen island. With a big

11:52 Bar stools. And um the cooktop is on the other side. And Whenever the kids wandered downstairs blurry eyed, I was their short order breakfast chef and anything they wanted. Uh I would be which was so fun. It was like the breakfast buffet of the four seasons or something. Whatever they wanted. I had it I could whip it up really, really fast because you get that skill when you're a short order chef.

12:15 I have my younger boy had some kind of ADHD stuff and started taking those the meds. I can't remember how old he was. Ten. Twelve.

12:26 And those meds make kids it's an appetite suppressant. Oh, for sure. Okay So you maybe you know. And I was a typical parent, our primal urge is to feed our children. That's it. Like feed and care for our children. That is the overriding program. That kind of puts everything else down. And so I got to the point where I was so worried about how skinny he was and he wasn't eating the rest of the day he was hungry in the morning and I would like make a twelve egg fritata and like put potatoes in it and sausage in it and he down the thing and I'm like, Okay

13:00 You should have. Yeah. The Anaconda diet. Just one huge meal. And it works. Yeah. And the punctuation on this one, aside from that just being really quality time. regardless of what kind of mood the kids are in, it's just really quality. I cherish it. I took a picture. Most days. Hm. Okay.

13:19 Totally candid, there no no posing. I would sneak a picture every day. And now I have a folder called The Breakfast Club on my you know, in my picture my iPhone pictures. And I have like a thousand pictures. And it's

13:32 A time series of these kids growing up. Yeah. It's a virtual possession, but it's my most prized possession. Alright, we're gonna double click on a bunch of things we we passed over. Yeah. Let's hop for the

13:45 The entrepreneurial set listening. This is also related to more than just pure entrepreneurship, but let's see if this is dead end or if it takes us somewhere. Who was Brad Chase? Right, Chase? Yeah. What impact did he have on your life?

13:59 Great guy. He was my first real Boss out of college. Mm-hmm. It's not quite right, but it's close to right. Mm-hmm. Brad was a group product manager at Microsoft. Microsoft was my

14:11 You know, I'll I'll call up my first job out of college. Mm. It had this nineteen ninety one, Microsoft had only about three thousand people at the time. And just for reference. Yeah. Because I have no idea. How many employees do you think they have now? gonna be a multiple of that of course three three hundred, four hundred thousand multiple orders of magnitude.

14:33 Two to three. And the product managers were kind of this elite little group of really smart people. We weren't very big. And he was my boss and we were working on MS DOS five. Which maybe I would say we'll have to go two standard deviations out in your audience distribution curve to find anybody who really knows what MS DOS five was, but it was a really big operating system.

14:54 for Microsoft at the time and we made an upgrade. And the feature was We broke the six forty K barrier. Which you're not gonna engage on the geeky stuff, but it was a really big product, and my job was to create the packaging, manage and manufacturing, and figure out how to get this Physical product into the egghead. Some of you will remember Egghead. Egghead was a retail software store.

15:20 And to push the product out into Egg. That was my first job and Brad was a guy who he's one of my mentors, you know, I only worked for him for a short period of time. I was a Big idea, thinker. Mm-hmm. You know, big risks, big bets.

15:36 And he encouraged me. At a very young age, he funded me to take a really big swing at something. And Supported me in it. And it failed miserably. So this is the book project. Yeah. You want to tell people about it? Well, I don't know how that interesting is, other than the lesson of take big swing. It is, but the detaint a picture, right? People can conjure a visual in their head. All right. It's become a huge series. It's a series for dummies. Blank for dummies. Yeah.

16:03 And the Look That the dummy series was founded on. was DOS for dummies, believe it or not. It was like the best selling Book about software of all time.

16:15 And I was like, I'm a young product manager, I wanna sell more MS Toss five upgrades. And I Was like Okay, we have all these software retailers where people go, but the really big thing at the time, believe it or not, was Barnes and Noble and Borders Bookstores. The bookstore experience was huge back then.

16:34 And Dosh for Dummies sold millions and millions of copies of this book. In Barnes and Noble and Borders. And so I Was like, why don't we Do a bundle.

16:45 With Doz for Dummies and have that be the manual for the upgrade. Mm-hmm. Bundle it together. The book And the upgrade. Seems reasonable. And distributed. Through bookstores. How brilliant. And so I went and met with Like one of the Riggio guys at Barnes and Noble. I met with the guy who created the dummy series, this guy John. So I met with all these people. We designed the product. It was really I was, you know.

17:09 Feeling pretty like a big deal. Built a bunch of it. Uh. Probably cost us. Eight to ten bucks a unit. Yeah. Okay, which is a lot for COGs, right? Yeah.

17:20 Cost of goods sold. I can't remember how many we built, but It was at best a C. You know, maybe a D. What was the retail price? You hit the problem. The problem was people are going in to buy a twelve dollar book. And it was a fifty-four dollar price tag or forty-nine dollar price tag, which is what the you know, basically what the software cost it at uh at Egghead. And it kinda looked a bit too much like a book. I kinda made it look like a book.

17:48 Wasn't the greatest cover. Anyway, I kind of I'm embarrassed about what it looks like now. I have one, of course. As a reminder, but yeah, it was just it was too the shock value was too much. People didn't realize there was software in that And so we ate we ate a bunch. We ended up getting rid of all the inventory, but it it was not a success. And the amazing thing. Depending on where your audience is in their careers, like you work at a lot of places out there. And

18:12 Great organizations Encourage innovation. Encourage big idea people to take big swings and do not punish them when it doesn't work out according to plan. If that happens too many times, maybe there's a pattern and somebody should go find another job. But Brad Chase, back to Brad Sat me down, I thought I was for my review and I thought I was gonna

18:34 Who knows? It was a ten, twenty million dollar mistake, you know? And I was a young kid. And he said, I remember distinctly, he said All right. What's your next big idea?

18:45 Ha ha. Amazing. That that is that Microsoft was and is an amazing organization because of that kind of culture. Well. How have you If you have sort of taken that forward.

18:56 into companies that you've built. Or just philosophically or operationally speaking. How do you encourage that? Because you there must be some constraints on things so that you don't light the whole house on fire. Yeah right. Yeah. How do you think about enabling people Two

19:14 Innovate. You don't want learned helplessness where they're afraid to do anything. Right. At the same time, you don't want some rogue trader like taking that's right. Yeah, it's really hard. But everything ultimately boils down to the people. that you hire and the people you choose to work with and the people you keep. And Saying your culture is XYZ

19:37 is very different from having people who channel that those traits that you want. And so My method for doing this is to make sure we're really diligent about finding those innovators and the entrepreneurs sometimes who The entrepreneurs, let's call them, okay? The inside entrepreneurs. And protect them a little bit because sometimes they're Different and

20:01 mainline corporate culture. Sometimes rejects, often rejects the innovators and the ones who want to disrupt Whatever, just ro rock the boat a little bit. And you really do need to rock the boat to innovate. And so the leadership needs to hire, cultivate, protect.

20:17 And invest in those people. Yeah. The foreign bodies so they don't get rejected by the corporate immune system. Which is just it's just natural. Yeah. You know? Alright, so let's Come back to one thing you mentioned.

20:30 He said in effect not totally true, but Let's consider Microsoft first job out of college. What was the actual first job out of college? It was I was you know, I was one of these High performance confession coming. Yeah, yeah. I I was just one of those kids. You know, I went to Stanford And uh was an engineer. No. I know, but this it was funny. There's a good story here. Um I mean I don't know if it's a good story, but we'll tell it.

20:56 Yeah, I mean, I was like success kid, like do well. Loved that identified that way. And so of course, whatever the hardest job that came to interview at Stanford when I was a senior, of course, that's the job I wanted. Yeah, there was like strategic planning at Disney. There was the kind of investment banking training program, analyst program. And there was like the strategy management consultant and those were like The big ones. And it was the most competitive, hardest to get to. That's how I got tracked and I took a job as a strategy consultant in Cambridge.

21:26 Right out of college. I knew pretty damn quickly it wasn't for me. It was a spin off of B Called Alliance Consulting Group. Great group of people. Super smart. It was going into a recession though in nineteen eighty nine and so a lot of people ended up losing their jobs. However, the the interesting thing was One of my besties. Not Stanford.

21:47 Nina Roberts. Who was an engineer with me. We were both interviewing for all the same jobs. And you know, she didn't get the big job. But she got this little tech company in Seattle.

21:59 You know, Microsoft, which of course I knew. Like the companies that I really love were Microsoft, Apple All I needed to do was buy Microsoft and Apple stock back in eighty nine. That would've that would have been yeah. I wouldn't be talking with you now. You know, Microsoft Apple I liked Patagonia, that was a brand that I identified with. Anyway, Nina got the job as a product manager at Microsoft. And she went to Seattle. I went to

22:20 Cambridge. And we kept in close touch and I knew pretty quickly it wasn't for me. And she knew Microsoft was the place for me and was like on the horn with me every week saying, You gotta come out here, gotta come out here. And so it took about a year To finally get the flight out and the job offer.

22:37 How did you know it wasn't for you? What about it? Wasn't for you. Because there are some people who thrive th in those environments, right? Yes, yes, yes, yes, yes. You know, a trite answer would be Dressing up in a suit and tie and wearing uncomfortable shoes wasn't for me. I like to go barefoot. Yeah. That really wasn't what it was.

22:56 You know. It kinda makes you feel important when you dress up. And I was like presenting things to CEOs and stuff and it it did feel important. And I got like a really good Business school education in competitive strategy, you know, the Michael Porter stuff. I I basically got a MBA in this one year.

23:13 What I discovered about myself And I discovered it there. I probably knew it before, but I hadn't really focused on it. I believe the world is somewhat divided. It is isn't totally Binary, but It's a continuum, but it's maybe a barbell. Clients and servers.

23:28 Okay, which is kind of a geeky geeky. Reference, but people get it. Mm-hmm. There are all of these industries that are set up to be service provision industries. Lawyers.

23:41 Doctors. Consultants. Academics. And the benefit of these industries is You get to indulge your curiosity and see lots of different

23:50 deal with lots of different clients and lots of different problems, but oftentimes with consulting, you're not seeing things through to the finished. And It was apparent to me really quickly that I derive my jollies on the other hand from being a builder and the client. I actually loved what the clients were doing more than what we were doing when when I was a consultant. So it was became clear to me that I was a client. I wanted to build things. I derive my jellies that way. And so I started looking. And it was good to discover at a pretty young age. Yeah. Uh and then I got to Microsoft and it was like

24:22 I was a kid in a candy store. I never left the place. Thank God for Nina, was it? Nina. Wow. Yeah. I hope she's still gets a box of chocolates. We're still close. She's great. Alright, so let's talk about then Microsoft And

24:40 Expedia. How does this happen? I'll just leave it broad. Well, back to the earlier conversation we had about Taking big swings and intrapreneuring.

24:50 The how on how this happened is that Expedia was a quote venture startup inside of Microsoft. And then it spun out. And we can get to that. But the real reason I even got into it and left the operating system group was that my wife Sarah, who you just saw

25:06 is a doctor, and she was applying to She was in medical school at Northwestern and was applying to her residencies. She's an OBGYM. And There's only one residency OBGYN residency in Seattle, where I lived. With only six or seven.

25:22 Residents a year. And one of the most attractive residencies in the country, so super competitive. We were engaged. And then soon married after that. We got married pretty young. And I was like, Well she's not gonna match out here.

25:36 In Seattle, so I Better get ready to move to New York City or You know, this probably would have been New York City where she matched. This was during the Windows ninety five launch. I left the Windows ninety five team and I went to the consumer division at Microsoft. Which was kind of

25:51 Small. Now just this is gonna maybe sound like it's not a little bit more than Like a side quest, but When you say you moved. Did you just put in a request?

26:00 Like how easy is that to do? At great companies it's relatively easy. Relatively easy. Especially for people who are tagged as high potential. Yeah. But it's still not easy, of course. Brad, who was my boss at the time. Couldn't believe we're launching Windows ninety five. This is gonna be the biggest

26:15 Launch of all time. In the software industry, or maybe w one of the biggest product launches of all time. I don't know if you remember that. It was a big deal. And About six months before we launched I had a big job there. I interviewed for jobs over in the consumer division.

26:31 And took on a portfolio of multimedia CD ROMs. And the reason I did this I was interested in consumer marketing, obviously, but the reason I did this was that I I was gonna have to leave Microsoft. Mm-hmm. And I wanted to start a company.

26:44 Mm-hmm. And it wasn't gonna be an operating system. Yeah. Okay. Like that this just wasn't gonna happen for reasons that You know, we don't need to get into, but but the government made clear To Microsoft at one point. So I figured it was gonna be a consumer software company and I wanted to go learn that. Mm-hmm. And the folks over there were fantastic. Microsoft was fantastic. And I took on a portfolio of CD ROMs.

27:06 Some of you out no out there will not even know what that is. This is kind of basically precursor to the internet. It's the thing your doctor gives you that you can't make any use of with all your images. And some artists, some musicians still hand out C the artifact that your doctor gives you. Oh it was what it was what the last the what what came in the red envelopes at Netflix. Um anyway, so but these things were like Wikipedia before Wikipedia was called Incarta. Mm-hmm.

27:37 And one of the products in my portfolio of like rando ideas. was in Carta. So an encyclopedia of travel guides. Mm-hmm.

27:47 Just really good. Take a whole bookshelf. A whole shelf of Travel guides cram it down onto one CD ROM, pictures, audio. Wow, what could be better for travel planning? And that was one of them. And I remember going into my first product review with Bill Gates and and others. Which was a kind of every six months, every year.

28:05 Kind of thing that the product people did. And I was used to like Business plans but billions of dollars from the operating system group. And I was responsible for this thing and I'm like, Bill, like this is tiny. The whole travel book industry in in the US is maybe a hundred million dollars. And that's

28:23 The whole thing. And so really, A, there's not an opportunity, and B You can't travel with the CD ROM. There there were no like like the laptop at that point was this compact suitcase that c that weighed twenty pounds. I'm like That's when you want the travel guy when you're traveling. So even though I know it's your idea and it's kinda fun, it's not gonna work. That said, I demoed

28:44 Easy Saber. On Prodigy. Prodigy was an online service. And I was a geeky online guy, right. And Easy Saber was A tool for travel agents

28:57 to use at home on Prodigy to access the airline reservation systems. Okay, so it wasn't meant for consumers. But I could get access to it on Prodigy. And I demoed that for him. He actually knew about it. I demoed that for him. I'm like, This is a change the world thing. If we can have consumers be able to do this, then we can become the largest. E-commerce wasn't a word then. We could become the largest seller of travel in the world. That was my pitch and my dream.

29:22 And fund me on the outside, because I'm gonna have to move to New York, because my wife, she's not gonna match out here, and this doesn't wanna be a Microsoft business anyway. It's Travel first, software second, not software first, travel second. He agreed with all that. He thought it was an awesome idea. He also liked that we could rebuild all the mainframes on Windows NT, which is a different conversation. So he loved it. He greenlit it. He was my first venture capitalist. He said, No, don't go do it on the outside, do it here. We have a great team we'll put together and I'm sure Sarah will match her residency at University of Washington.

29:57 High degree of confidence. That was the end of that. She did match. I honestly to this day don't know if there was any thumb on the scale. I doubt there was he had that kind of power, but she matched. I stayed in Seattle. He had promised me that he'd consider spinning it out if it got big enough, and then that's what happened. So we spun in the height of the internet bubble, which is so bubbly that people today who think we're in a bubble have no concept. I mean you remember. Oh yeah. Ninety nine. I mean I moved out to The barrier in two thousand. It was crazy. Impeccable timing. We all thought we were the smartest people in the world. We really did. And we all thought those people in New York City just didn't get it. And then there was come up and Expedia was a really good business. I was working for Balmer. At the time. And I s asked Steve for a hundred million dollars to spend on a television advertising campaign, because I said, We are becoming, we can do this. We are in the pole position, we can build the biggest brand and travel.

30:58 And Steve like laughed at me, like No we don't do that. I said, Well Dog shit.com is going public right now at a billion dollar valuation. Wasn't quite that. It was like five hundred million, which seemed big at the time. Really Some stupid stuff in my closet.com was going public. You know, put it on the web. Anyway, and I was like

31:18 The public markets would give us a hundred million dollars. And it'll cost basically nothing. And so let's give this a try. Let me spin this thing up. It's a good HR experiment, human resources experiment, too. Now just to explain for folks, why does spinning something out make sense? What are the advantages of doing that? To them and to you.

31:36 Okay. I mean the financial answer to that is unlocking value. That is stuck in a company. And this happens a lot. Mm-hmm. That's kind of the most uninteresting one. Unlocking value meaning It's not getting valued by the shareholders as being part of Microsoft. But if you if you take it public or do something outside of Microsoft, all of a sudden it could attract its own investor base that were interested in that in particular. But there's a conglomerate discount, generally speaking, in the public markets where the more stuff you have in a big company, the less the individual businesses are valued. There was a period of American business history where conglomerates actually got a premium. Like in this like in the GE, the Jack Welch GE days, and Honeywell and all these big conglomerates. And then the pendulum swung the other way. Microsoft could have

32:25 Cared less about the financial play though, however. I pitched it mostly as an HR experiment. Microsoft was getting so big. at the time that people could hide out in random corners of Microsoft. And as long as Windows NT, the operating system succeeded, or Office Microsoft Office succeeded, they could make a lot of money off their stock options. Mm-hmm. And so that's basically a

32:50 Compensation accountability disconnect. Okay. And so Some of the best people at Microsoft there was this Field of dreams, w wild opportunity outside of Microsoft, even though it was the place everybody wanted to work at the time.

33:06 Probably still is. There were great people, like I'll just say like me, like I would not have stayed. I would have gone out and started something on the outside because the opportunity was so great. And so Steve Ballmer understood this really well. This was like a talent retention pitch. Sort of. Sort of. And so he's like, Yeah, we'll take a flyer on it. And that was great. And Greg Mafey, who was the CFO at the time, he became my chairman and he was really supportive.

33:29 You know, he and I still work together. He's been a great Great mentor to me. We took a hundred and fifty people out of Microsoft. We gave them the choice if they wanted to stay or come. All but I think two people. We had a hundred fifty of us, all but two people decided to come, take the adventure. Give it a rip.

33:44 I was thirty two years old, thirty one, thirty two years old. Now were you pitching those people yourself? Yeah. What was the pitch? Palmer. Uh.

33:55 Yeah. Way different. I mean it was I had had this idea for a while and so the people I recruited back to an earlier comment I made the people that were on the team were the people who were the adventurers and the the ones who wanted to Who would have left. Okay. And so this was all about the adventure. The hardest sell was not the people, it was the spouses. And I remember several dinners, like with an S one. For those who know it's an IPO document, with our our expedia draft of the S one lying on a dinner table at Wild Ginger in Seattle with a skeptical spouse. The S one is highlighted and like there's annotation, and I'm having to answer like

34:37 You know, those were my toughest investors, actually. It worked out w really well, maybe too well. Because Expedia was a real business, we actually were profitable and growing like crazy. I mean, obviously. Digital travel agent made a lot of sense. Okay. And so when

34:53 Thom and Louise one off the cloud, as you say. We were already public. Okay, and we gone to the moon, the stock price had gone to the moon, we crashed back down, but we had a real business. And very shortly. popped back up on the climb and just climbed from there and were very successful. Microsoft, however,

35:11 Crashed. And it took seventeen years for Microsoft to reachieve the same stock price it had in November of ninety nine when we spun Expedia. So the H R experiment kind of failed. How long did it take Expediate recovery. Or to get back on the climb. I mean not sometimes to reach the all time high probably a couple years. Yeah, but a couple versus seventeen. Yeah, but the the valuations were s a bit nutty, right? So

35:37 It was obvious that Expedia was on the right path very quickly. And There was kind of a flight to quality with internet investors, which meant find the profitable. recent IPOs, which there were not many. And let's invest in those. But we were one.

35:53 Just a quick thanks to one of our sponsors and we'll be right back to the show. This episode is brought to you by Shopify. Shopify is the commerce platform revolutionizing millions of businesses worldwide, and I've known the team since 2008 or 2009. But prior to that, I wish I had personally had Shopify in the early two thousands when I was running my own e commerce business. But the tools then were absolutely atrocious, and I could only dream of a platform like Shopify. Whether you're a garage entrepreneur or

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37:01 So sign up for your one dollar per month trial period at Shopify.com. Slash Tim. All lowercase. go to shopify.com slash Tim. to start selling today with Shopify. One more time, Shopify.com.

37:14 Slash. Tim. I Maybe this is not a good question, but I have to ask, how did you learn to pitch? How did you learn to pitch different stakeholders? Because you're talking about employees.

37:29 Balmer. Gate. Spouses. That is a skill set. Persuasion.

37:35 Yeah, how did you develop that? I it just must have been a an innate thing that got a lot of exercise as I was growing up. I was an engineer by degree. But Never a practicing engineer. I was an engineer because I liked

37:50 Technology. Mm. I was initially. The story there kinda answers the question. I was an industrial engineer. Theoretically, but I wanted to go study in Italy my junior year. Mm-hmm. Now industrial engineer would be like you end up going to a smart design or one of those types of companies.

38:09 Or how are you thinking your path would be. It does it's not a degree anymore at Stanford. It's called management science and engineering and then there's a kind of a symbolic systems things. The in industrial engineering degree, which kinda sunset it, was really a kind of Manufacturing efficiency. I got it. Okay. I got it. Optimization simulation. Lots of computer work going into the design of making things more efficient. Yeah. Kind of like the operations, research, finance department or other places. Yeah. I did it just because it was

38:38 A Bachelor of Science, not a Bachelor of Arts. And it was the most businessy of the engineering disciplines. At Stanford they called it imaginary engineering.'Cause the mechanical the mechanical and the electrical folks didn't respect us. Yeah, probably deserved it. Because we're more interested in business. But anyway, I did this because I had all these other interests and skills around persuasion and people and entrepreneurialism and Already at that point undergrad. Already, already. As a kid, I had all that. I probably was a good pitch person already, but had a lot of support.

39:12 And exercise of that. You mentioned Italy in passing, so we're gonna come to Italy. But How did you get that exercise when you were younger? I went to Italy so I got off the Industrial engineering track.

39:25 And Stanford was awesome. I came back And they're like, Well, you can't get a accredited degree now. I'm like, I don't care. And uh Nina's dad was a professor at the time and he said, Well Stanford you can self design an engineering degree, so let's just design one for you. So we design I designed one. So my degree is called General Engineering Colon. Industrial economics. Anyway.

39:45 You know, unlike a lot of kids today, I worked real summer jobs, you know My kids generally did actually. My kids had worked real summer jobs. So we were talking like bus boy or Yeah, I mean my daughter, I was thinking of what their jobs are right now, but my daughter spent You're you're gonna know this place. You know, after Gurney's was redone it became like this club scene. This is out in Montreal. It got super fancy. Took away the day passes for the locals, you bastards.

40:11 Uh yeah. Oh so she was it was after her sophomore year in college, I think, or fresh yeah, sophomore year. And I'm like honey, you've got a Place to stay out in the Hamptons. You don't need to get on the track the track that every smart kid is supposed to take. You don't need to do that. Why don't you get real experience? So she came and lived in our house out in Montauk and Was the

40:35 Who's the person that stands at the counter when the hostess. The hostess at the club part of Garners. Okay, where where it was like thousand two thousand dollar tables. Yeah, yeah, that's quite an educational human nature job. Oh my god. She had a crazy successful, interesting learning experience. Yeah. Yeah, and I we we had fun watching it happen. And we also got table set. Anyway, when I was a kid, I was the ice cream man, so I ran my own ice cream business. This is in Connecticut. I went to high school in Connecticut. I learned how to do house painting. As a crew member of a buddy of mine.

41:11 And then after one year doing that, like Mm. Well, I can bid the jobs myself. You know, and I can hire a crew. And so I had my own painting company for a couple of years. Which

41:21 was hugely profitable for a kid. I mean, I made a ton I had to pay for all my expenses at college. Not my tuition. My parents covered the tuition, but I had to pay all my other expenses. So making back then I would make like Fifteen thousand dollars or twenty thousand dollars summer painting and that was boatload of money. Yeah. And so I had run my own businesses. Mm-hmm. Got it. And why did you go to Italy at all?

41:47 Why did I want to go when I was in school? Bye. I have no Italian heritage, as you can probably tell. Uh but I went to Italy and Greece when I was in high school with my Latin teacher. And Just had these awesome kind of kid high school trips.

42:04 And I while I was in Italy, I literally fell in love with the whole vibe. The food, the wine, the girls, the family, culture, the kind of work is not that imp as important, you know? And I kind of fell in love with it. And kept going back. So went to study and then after I sold Expedia to Barry Diller.

42:26 We were Republican, Barry Diller bought it. And we had three little kids and I was leaving after Barry Ba I wanted to give space to the next team. And I said, Let's go back to Italy. And so we moved to Florence for a year after we sold Expedient. In fact, Nina, who I was talking about before, she was living there, married to a European guy. Uh, and s I'd gone to Stanford there when I was a junior and I had kept in touch with the woman who ran the Stanford program, Linda.

42:52 And so we kind of moved to Florence and went back to school. Um learned how to paint and started road biking. Anyway, so I just I love the whole Italy butt. Let's take a closer look at the Barry Diller transaction. Yeah. Yeah. How did that come to be and what were the most important aspects of that deal.

43:12 Could be deal structure, it could be timing, could be anything. But how does that even happen, right? Yeah, so Expedia had been public for maybe four years. Mm-hmm. And Had become Very successful and pretty big, you know, pretty highly valued.

43:26 in the market. And I think it came about I mean, Barry was kinda interested. He was building a Interactive conglomerate called IAC. IAC, right. USA networks and then I think he owns most of the popular dating apps, things like that. I mean IAC buys a lot of stuff. Yep and then spun it out as match dot com. Yep. You know, and

43:46 Yeah, he was post his media career, he got into interactive media and he started buying stuff. And the guy a guy his kinda key corporate development strategist An all around great frickin' guy. Who worked for him was a young guy named Darakazushahi. Uh okay. Folks might recognize that man. I don't I may be miscrediting or giving you too much credit, Dara.

44:09 Well probably not. I think this was Dara's idea was consolidate the players. Mm-hmm. in the online travel space. That it was already big, but it was gonna be much bigger. And

44:22 Microsoft Was like majority owner. But didn't have anybody on the board? Even they own sixty five percent of the company didn't have anybody on the board. Greg they knew me and they trusted Greg McFay, who had left as CFO and running company. Unbelievable level of trust. I guess it's just as a percentage of the total. And at some point somebody came in I won't name names. Somebody came in and said, We need to focus at Microsoft. We need to get things focused. We're too scattered. And an easy thing to do was to take a big offer.

44:51 From Barry Diller and so they they did. Was a bit of a two step deal the I C and Dara and Barry bought Microsoft sixty five percent. And then maybe

45:04 So we were public but captive to IC and Barry Diller was my chairman for a while and then maybe eight months later bid for the for the rest of it. And consolidated it down. We Or I think they kind of pushed us to buy the number two player. Which was hotels.com. Mm. And so we mashed those things together and I moved on at that point. So when in that journey, the expedia journey

45:27 Did you feel the highest high like for instance, I would imagine When you were working summers and on your way sort of through high school and college, there was probably a moment, I'm just guessing here, but when you had your first big summer with that. Painting gig and made fifteen, twenty grand. Yeah. Thank you

45:47 My God, you must have felt rich. Yeah, we went to the highlight. You know the highlight is? Yeah. Took the crew to the highlight. Yeah. So with the expedient journey. Yeah. Was it the tail end with the Barry double transaction. No. 'Cause there's mixed emotions there, right? Yeah. And I didn't control the company. I learned that henceforth I would control the companies that I started.

46:08 No, I mean that was Great. And it made sense and it created value. No, the highest highs were I mean, probably around the spin out. And the IPO.

46:18 There's kind of a funny IPO story that My wife, Sarah, was pregnant with our first child, Will. During the road show. Okay, so this is November of Nineteen ninety nine.

46:28 It's really pitching to the buy side. So it's pitching to the mutual funds. To the investors. Okay, got it. And it used to be. I think now is a lot more on Zoom. Which is it should be, by the way. But it was a rite of passage back then for companies public and a lot more companies went public than

46:44 Mm-hmm. And it was fifteen cities over three weeks. Five meetings a day, six meetings a day, chartered private plane with banker team and CFO and CEO. Zipping around the country. Okay. Exhausting and exhilarating. And repetitive.

47:02 And Kind of boring, also really fun anyway. So Sarah was pregnant and she wasn't due until December, but We had been on the road for Two and a half weeks already, we'd filled the book thirty times over, which means we had a lot more demand. We knew the offering was gonna be successful. These were back in the days when the offerings were a little bit managed to the advantage of the inside banker people, but anyway, that's a different story. So it was gonna work. The IPO was gonna work. And I called the road show off a day early. I flew back to Seattle.

47:30 Exhausted. I get in bed at like One in the morning after getting home, Sarah's super pregnant. I get a tap on the shoulder. Uh

47:40 Three AM And she said She's an OB, so she knows what's going on. Although that's not always the case, but she knows what's going on. And she said to me, honey. This is like

47:54 IPO day. If our baby is born On the IPO day, do I really have to name him Expedia? Which is what I promised the team.

48:05 And then we went to the hospital and while the IPO was happening My son was being born. That w yeah, my my my my oldest was being born. And so that was actually the high point right there. Wow. All right. No We're tracking the path.

48:19 So now you're Painting a vase of Fruit in Florence. Living the life of a naked it was a naked woman, it was like a it was like drawing. There we go. Sharco. There you go. Naked lady. Changing poses every ten minutes. What could be a better way to learn art.

48:41 And Living the life of a refined gentleman. Pasta and wine and culture and road biking. Little cap, maybe. Little cap, of course, no helmet. Little. Taking Italian classes in the morning. Yeah, yeah. So here and there. Sounds like a great life. So how the hell

49:00 Does it Zillow happen. Yeah. Do you start getting fidgety? I mean what what happens there? Yeah, I was still pretty young, so probably Oh three, I was like thirty five, thirty six.

49:13 And I was hoping our Music. Thought I might Write books. Whatever, you know, find the next chapter.

49:22 Mm-hmm.'Cause I really didn't need to I had enough to take care of myself for the rest of my life. But something I discovered a I was still on a few boards. Mm-hmm. Including the IC board. Which had bought Expedia and Netflix where I've been on the board.

49:37 Since like two thousand. And still I'm still on that board and a couple others. So I was still involved in the business world from a kind of long in a long distance way. Though I had an amazing time learning experience, I didn't find my next calling. And I was still really curious about the business world and what was going on.

49:57 So I knew that I had we weren't gonna stay in Italy, we were gonna move back and I was gonna do something else. Which is great to learn. You know? And we did. Doing in Florence for a little over a year. We spent a few months skiing with the family, which was really fun.

50:13 In the mountains. And you came to the US. I am going on a hunting expedition. Did you already have an inkling of what you were going to do? Little bit. I didn't know if I really had another startup in me. Because I knew how much Work it was, and I'd adjusted my life.

50:30 To prioritize Some things I hadn't prioritized when I was younger? Like living well and Family and body. Mm-hmm.

50:37 And mine. Yeah, it's very curious in all kinds of different things. So the venture capital opportunity w was available to me to go via GP At a venture capital firm and I was kinda headed in that direction.

50:50 And then my Zillow co founder Lloyd Frank was a guy I went to Stanford with and did Expedia with. He was still at Expedia and he got fired. By our good friend Eric. Who was running Expedia at the time.

51:04 Probably for good reason. Awesome guy, really smart. I won't follow up on that a little bit. But Lloyd so Loy got fired and Lloyd's like, wait, wait, wait. Don't move to California. Let's just sit in an office and brainstorm for a while. And so we did.

51:23 We did, and we went through a bunch of ideas. He went off on one that was kind of Dropbox before Dropbox is like w it was obvious that the kind of cloud storage thing was gonna be huge. And I I said go figure that out. See what it's cost. See what you know, and so he disappeared for a couple of weeks, so we were kinda sharing an office. And came back and said, Yeah, a hundred percent this is gonna work, but there's gonna be no prof there's no profit. Like it's gonna be

51:45 Microsoft and Google are gonna give you a Where were you guys brainstorming? We were brainstorming in his dad's his dad was a stockbroker, where he had an extra couple of rooms in his office and he just gave them to us. New York City. No, no, this is Seattle. Oh Seattle. Yeah, I got I got Yeah. So we're in Seattle.'Cause we didn't sell our house in Seattle when we moved it, we'd move back to our house. But we were looking for a new house.

52:04 We were gonna maybe move to California. Or something in Seattle, our family was getting bigger. And so we went through a series of ideas. And then at one point I said hey, you know. Back when we started Expedia, we also wrote a plan for an electronic stockbroker.

52:21 Matchmaking service, all the classified categories basically, and all the kind of agent categories. We're all obvious that We were on a little team of people researching big ideas inside of Microsoft. How would the web change industry? And so we had all these plans. Expedia was one of the ideas. There was a basically to create a digital real estate marketplace.

52:42 And I dusted that off and I said, Hey, what about that? I mean, you're looking for a house right now. It's really freaking hard. This is two thousand and three. And I can't get the price of a home. Online? Like

52:55 I can't even get the address. Because the industry had been very good at defending their special data. Making it opaque. Yeah, yeah, yeah. And we were the power to the people guys. We were the guys who freed all that information for the regular traveler. And we're like, well, wants to be power to the people here too, right? And we couldn't believe that it hadn't changed. And so at that that was the dawn of Zillow.

53:19 Yeah. So he he convinced me not to move and I said, Well I'll be CEO, but I'm not gonna work that hard. He's like, don't worry, I'll do it. Just be CO. I need you to be CO because you have to raise money and stuff.

53:32 So maybe I am a four hour work and cat kinda guy. I said, Look, I don't want to do it full time. Like you can use my name. Of course he was like, Yes, sure, whatever. You can do whatever you want, Rich. Knowing I'd be sucked in. Let the line out. He totally managed me. Yeah, I think I'm in charge now. Lloyd was in charge. So when you say you're brainstorming, right, there's an entire universe of possibilities. Yeah. What constraints or criteria are you applying to that brainstorming? What are you looking for?

54:01 I think most great ideas that there's just a Big Obvious problem. I like consumer stuff. And so that means the way I interface with the world, the way we all interface with the world is rife with problems.

54:15 And all those problems are business opportunities. And when you see a particularly big oh my God, why is it this way? Those are probably the bigger opportunities. And It's almost as simple as that. We identified this big dislocation.

54:28 We knew one hundred percent. That there would be A Leading digital real estate marketplace in the US at some point. At some point. Inevitability. Inevitability. And business model

54:39 Who knows? Who cares? It's a giant. Mm-hmm. It's a big pond. You know, and so my business criteria for doing stuff is is it a big pond and are there good fishermen? Right, because the the travel CD ROM wasn't big enough, right? You said small one.

54:55 Hundred million. That's the entire market. Plus you're not gonna carry a briefcase. That you're Doing weight training with inadvertently. Problems. To read the thing. Right. A lot of entrepreneurs make

55:07 This mistake of Identifying a really big problem, but it is just a small Opportunity. Mm-hmm. And then there are ones where like I'm I know Bill Gurley was on on the pod, you know

55:19 couple of years ago talking about the Uber thing. What did the The inside you were involved there a little bit. I was one of the first three advisors when it was called Uber Cab L C way back in the day. Yeah. And for people who didn't pick up Dara. Yeah, oh sorry, Car is the CEO. Current CEO of Uber. He was the CEO of Xpedia after, you know Mm. Two after I left as well.

55:41 Anyway, a lot of people make the mistake, is what I was gonna say. of identifying a real problem, but it's just too small. Uber kinda to some pe a lot of people looked too small because it was a black car tan. But the inside that you and girly and Travis and I guess J C H and others had was that actually no was gonna It was gonna take not just the black car market, but

56:07 Taxi, transportation, and then ultimately more. It can expand the total addressable market. That's right. Car ownership. Yeah. Just transportation. You know, and of course Obviously it's

56:19 Beautifully played out that way. Took a little while to see, but it's yeah, amazing. Anyway, so Big pond. Good fisherman. After identifying the big problem. And I guess that was the guiding thing here. I knew Lloyd and I knew There would be a digital real estate marketplace. We didn't know what the business would be.

56:36 We didn't know h what how we were gonna play. And we started poking at ideas for attracting audience. With software. Mm-hmm. And we made a couple of big mistakes before we landed on the solution. Yeah. What were some of the big mistakes? And how costly, how risky were they?

56:54 Pretty small venture numbers at that point, and Lloyd and I were funding it all ourselves. You know, we put the first five million bucks total in with a couple of friends. So Costly, but not that costly. But the first idea we were not also what Garrett Camp did with Uber early on. He did too. He wrote yeah I didn't realize that. Yeah, there was self funding for a while. Wasn't expensive. Yeah. It wasn't overly expensive, but It's a good way to go.

57:18 As a Second time founder or a non first time finder if you actually have some resources. Because you end up with more of the company down the road. Yeah. You know. I love girly. We're really close. But what by the time Girly or the venture capitalists come in, you know.

57:33 If they're writing the first check, they're gonna end up with a big chunk of the company. Which is great. Especially if you get somebody like Bill. Okay. But we were able to do it our ourselves. We were enamored of

57:45 Google everyone was at the time. the magic business model that they sort of discovered or innovated, iterated on that came from another company. was the Adwards. You know. The

57:58 Digital. Auction based marketing. Yeah. I might not know that wrinkle. Yeah, it did. Meaning they acquired something or they I'm thinking what's the guy's name who did the startup incubator factory, gross? Oh Bill Gross? Yeah.

58:11 Yeah. It was I mean I may be getting this wrong. He did ideal lab. There was a d a lot of companies kinda s sort of spun out of that, but one of them was A search engine whose name I'm forgetting. We can you know look it up later. And but it was the whole basis of the search engine was Edwards. Edwards. Oh wow.

58:32 So did Google acquire that or they just be in a better mousetrap? Think the latter, but I'm not an expert. Regardless, I don't want to speak out of terms. We'll put the story in the in the show notes. Okay, right. It's pr it's there's a good story there, I'm sure. Why I brought it up was we were enamored of

58:50 Auctions. Mm-hmm. Auctions are have huge geek appeal for Matthew idealists. And we were like, Well, obviously the US housing market should be an auction, and that's the most efficient mechanism for price discovery. Okay. Which of course it is. And we were like, Okay, so that's our business. We're gonna auction homes. Mm-hmm.

59:10 And what we learned Trying to auction a home. Jordan got us uh kind of on consignment. Was that

59:18 Well, two things. One To have an auction work, you kinda need a real time liquid market. Mm-hmm. Okay. Duh. Okay. Uh so you need all the bidders there at the same time. Okay. Well the the housing market doesn't work that way. It's just, you know, it's a it's a it's a long period of time. You wanna show it to a lot of better side. You know, that that didn't work.

59:38 The second thing, which is obvious, is until all those Innovators out there. If you have to educate your customer on how to buy the thing that you're doing, if it's like a radically new way to do it, uh you know, from decades or hundreds of years of ingrained human behavior. It's a pretty heavy lift.

59:58 It's gotta be super duper simple, obvious, and ten times better than the current way. And just we didn't check any of those boxes. But in Pursuit. Of price discovery.

1:00:10 We Found this estimate. Which was our killer feature. And the visual on the z estimate that's in m in my head that kind of popped in in our collective heads on the home auction web experiment.

1:00:21 was a real time estimated value algorithmically driven As your Google Map zooming over neighborhoods, looking we wanted prices on every roof. Because everything should have a price. That was And the timing of that is pretty wild, right? And it's just like how things line up because I I mean how long had the aerial view

1:00:42 been around prior to you guys. Short. It was short. Short. And there was no iPhone, there were no smartphones. Yeah. But it was obvious. Like I was like, Oh and then I also had in my head Homes are for home American homeowners Oftentimes their largest asset.

1:00:59 And the bulk of their wealth. And people care a lot about it. Yeah. So I knew they wanted to know the value. I knew that was Captain. Okay. I knew I in my gut I knew that was c we did, the team knew it was candy.

1:01:12 And I'm like, Oh, it's an investment. And so let's plot the zest and the home value like a stock. Chart. And so The aerial view with the numbers.

1:01:22 Any home's value. laid out like a stock chart. Those were the two things. And when we discovered that, we were kinda off to the races. Okay. So At the time was it just rentable infrastructure, AWS, you get it going, you launch, and it's up to the right, just a nice smooth rocket launch. Is that what happened? AWS didn't exist. I know. No dude, man, this was like server in a closet.

1:01:51 Yeah, this was server you forbade Christmas lights or something, like you're like preserving electricity and compute power and all the stuff. I don't remember that. I don't remember. David Bytel, who was our CTO at the time and still is, and was CTO at Expedia with me too. He may have told that story somewhere, so it may actually be right. Yeah, I I I believe I remember our launch blog post with Garrett, who worked for David. Like doing the what's the professor in uh Doc. Doc from Back to the Future. Whatever. Because we launched And millions of people showed up.

1:02:29 Because Walt Mossburg Who was who's the equivalent? Is there any equivalent of Walt Mossberg now? No, it's like the the uh the Oprah of tech at the time. Yeah, I mean God, and Walt loved it, and Walt published and millions of people came on day one. And of course the server in the closet tipped over for a while. And it was painful, but Amy Bratinski, who was running our marketing at the time. Said, Don't worry, we'll make lemonade out of lemons and the headline the next day in the San Francisco Chronicle was

1:02:59 House porn site. Zillow Launches and falls over Because it's so popular, or something, you know, something like that. And uh she's like, Yeah, that's gonna be good press. Anyway, I I I'm a big believer in

1:03:14 The product being the most important part of the marketing mix, if that makes sense to you. Gurley actually challenged us when we launched, he was on the board. Benchmark and T C V were our A round funders. And he was on the board at the time and we had had kind of a spend advertising dollars mindset at Expedia because we really needed to grow exposure for the brand. And Gurley said, Well what if we didn't have any marketing budget? And that

1:03:37 launched. We were like, No way, you can't do that. And but that made us think a lot more creatively about the features that we built, the way we built them, and then the way we PR communicated them. And I've since developed a pretty good playbook around, I guess what I would call provocation marketing, you know. When you have really provocative feature that you know people are gonna feel emotional about one way or the other and they're gonna talk about it. You're on to something. What are some aspects of that toolkit or the playbook?

1:04:08 Yeah, I mean having data. Having a stream of data that people are interested in at Glassstore, which I did with uh Bob Homan who who was at Expedia with me as well. Glassdoor's another example of that. When you have constantly changing data that people are interested in.

1:04:26 You can almost think about feeding that data to hungry consumers in a Bloomberg like way. And so the playbook that Amy kinda put together was building a

1:04:38 data distribution infrastructure down to the line. Amy was our our marketing chief at Zillow. She's still on the board today and she was really creative about Recognizing that there's an infinite news hole for housing data at local newspaper level, once upon a thought. And If you could wire that up to just feed, constantly feed.

1:04:58 Yeah. Endless appetite. Housing is just an important topic, right? And there's always space in the paper for a story on housing and changing prices. And so we set up a mechanism to feed that data, which was a terrific brand builder for us rather than spending ad you know ad money. And then just having this estimate be so provocative. Like You know, high school boyfriends, house philanthropist development team that are trying to figure out who's a good target, you know, whatever. Like it's a application. Yeah.

1:05:29 I know you had a lot of fans. I think the Arizona Attorney General was a fan. That's a deep cut. Wow. No, but w this is of interest to me because there's opposition also. Oh yeah. Right. And A lot of the number of I don't think they were actual ulcers, but just the roller coaster ride that I was also on with Uber.

1:05:52 From a regulatory Yeah. mobbed up local fill in the blank perspective. And it was just nonstop battles. And that was just part of the deal. Yep. Right. If you're actually part of the playbook. Yeah.

1:06:04 Honestly, it's the same provocation marketing. It's the exact same thing. It's exactly the same. Yeah, I mean, you know, we were provocative to some of the industry players who were big lobbyists. Yeah. You know, the taxi commission in Uber's case. Yeah. In our case, a lot of the real estate professional associations. They were not they were not thrilled. Don't not thrilled. Or they think they're not thrilled. They don't realize'til later that it's could be helpful. But

1:06:29 But whatever, yes. They were they were provoked. Nobody no industry that's likes change. Most people don't like change. I'm one of the people that like loves change, but a lot of people most people don't. And so We were seen as a th we were seen. You may like change when you're the instigator of the change. Well that's you know, awesome. It leaves me more open to change coming from the outside too, though. I do believe. I do believe. And I and I and I I mean obviously this is just human nature. Yeah, but the equivalent of the taxi commission in the Uber case. was these real estate professionals and a lot of places we had them lobbying to have us outlawed.

1:07:08 Mm-hmm. They're not licensed. How can they make an appraisal, you know? Whatever. Whatever thing they're gonna make up. We knew we're on really strong legal ground. Mm-hmm. And so we weren't so worried about that. But the strategy for combating that

1:07:22 Resistance. Mm-hmm. Was literally probably the same thing. You guys did it Uber. Which was We knew

1:07:32 The legislators State legislators Not to mention federal legislators were big And of the site. Mm-hmm. And the service. Yeah.

1:07:41 Okay. And so All we had to do was make sure we just activated that latent love. Mm-hmm. For the product itself. And made it

1:07:52 Obvious that this way is the future way. And the lobbyists got nowhere. And it was overcome. Yeah, in the case of Uber I don't want to. make this uh overly about Uber but also Turns out when people have something that is incredibly convenient and useful, they do not want it taken away. No. And

1:08:11 If elected officials like the service or are even ambivalent about the service, they do love getting reelected. And man o man, if there are a lot of your constituents Using that app and you take it away. They're not gonna be super happy about it. Power to the people, baby. I mean like you build

1:08:30 Magic stuff for masses of consumers that they want to talk about with their friends unprompted. On the sidelines of the soccer game or what have you. Have you tried Uber? Have you tried Zillow? Have you tried Expedia? Whatever. It's like you're definitely on to something. And having popular support as we're learning politically right now is having big Populist support is ultimately where the power is derived. So Sometimes you can go too far. We don't need to talk about that, but of course you can go too far. And in fact it may be that you need to go too far.

1:09:01 To establish where the frontier is. Well I can't I can't. not take the the bait on that one. What does going too far look like? I was thinking specifically over about Because it did you know, in some cities municipality or orbit. You can you can push too hard. You can push too hard. And learn some lessons about

1:09:24 How Much. leash you're gonna be given by the popular support. 'Cause it does tip into a point where like with Airbnb You know, this is not a story I know this guy's a little bit, but it's not a story I'm intimately familiar with, nor was I uh an early investor or anything, but you know, they did piss off

1:09:42 Some owners, yeah, in certain Cities, not just the hotel owners. Yeah. And you know, so they found the line. And I think they've managed it really, really well because they lead from the heart. You know, I think other companies may have not obviously led from the heart and had had had difficulty. At Zillow our our j our job was a little easier. Also with those battles, I remember there were early on a number of locations that were incredibly important.

1:10:10 Yeah. Not just from a ride volume perspective, but from a precedent setting perspective. So if you win a few of those Precedent setting. battles, then you don't necessarily have to do like a full frontal assault. On the next. That's right.

1:10:24 Ten locations. Because people have gotten the message, you can be a little more diplomatic about it. Which people figure out over time. But then there's the next country and then whatever. Anyway, so there's always something. But uh provocation marketing with a heart.

1:10:39 With The end consumer's best interests in mind. That's a winner. So if you were teaching a class, maybe you already have, I have no idea. Related to provocation marketing. All right. There you go. You get to choose. You can go back to your alma mater or wherever it might be. You're teaching a class. Yeah. What what would other Elements of the class B. Resources, principles, anything at all. While I try to figure out a

1:11:05 structure here on the flat to give a couple other examples of stuff that I've I've been involved with. So I could have found a glass door. Which many people out there may may know. Um and our provocation data marketing feature was How much money do people make? Mm-hmm. Okay, not individuals.

1:11:24 But The Product manager at X Y Z company or the developer or the Customer service representative. And our model was we knew that Salaries was kinda ta a little bit taboo for a lot of people, so it was inherently secret and provocative. Okay.

1:11:40 And then Robert Homeman Who is My co founder and and and the team They had a data collection problem'cause it was ultimately user generated content.

1:11:51 People would need to share their salaries. In a way that we believed. In order to get enough data. to provide anything interesting to everybody else. And so their innovation

1:12:03 After kinda hand cranking it. With survey? Their innovation was give to get. Uh You show me yours, I'll show you mine. Very good. That's very clever. Very clever.

1:12:15 T. I'll give you a little taste, but if you want to see any more data, you've got to share your salary and your title and your company. We promise you'll be anonymous. You know, and do a company review. How people screwed that up where they're the only person in that position. Yeah, yeah. Yeah, we did have protocols for that. Uh but it worked really and we we also then solicited feedback on what it's like to work at the company. And you know, CEOs are kind of public figures, so okay, we're gonna let you review the CEO performance. Yeah.

1:12:47 And we knew all those things would provoke. We knew some CEOs would go crazy, you know. So there's another example while I'm formulating a framework. The another one is With another former expedia guy Mark Britain. We founded a company called Avo.

1:13:05 Which was in the legal space. And we decided to rate attorneys. Systematically rate attorneys. This had never happened before. It was just kinda like Trip advisor for attorneys. This was these are

1:13:20 business models that are well trod now, but these were kind of innovative back in the day. And of course We were gonna get sued because we were rating attorneys. Yeah. Definitely a great way to kick the horn at its nest. So some investors, when we were raising money, I remember traveling around, you know, doing the sand hill shuffle with Mark. And

1:13:41 You know, I remember some people saying, Well Is this legal? You're gonna get can you rape people? You know, you're gonna get sued. You know, I'm not gonna invest. And we were like Yeah, we're gonna get sued. You know, did you see Die Hard? You remember Die Hard where the German terrorist leader

1:13:56 is waiting for the last lock to open and he needs the power to go down in order to be able to get the bearer bombs out of the Nakatomi Plaza safe. Yeah. Okay. And the people are like, How is he gonna get the power to go down? And he's like he said Ladies and gentlemen, I'll give you the FBI. And they came in on those things and the FBI, the playbook said, All right, cut the power. Yeah, yeah. Anyway, that was exactly the launch strategy of Ava. It's like here come the suits. I'll give you the FBI. Anyway, it was perfect because it created all kinds of noise. I'm struggling with the lawsuits. All right. So the Sandhill Shuffle for people who don't get that reference. So Sandhill Road. If you could imagine. Going to like This is not gonna be the best comparison. But you go to like Kuwait and there's a shopping mall with like

1:14:44 Balenciaga and like Prada and all the fanciest brands. All the aspirational brands. Well, if there were such a place, but it was all the highest end venture capitalists, that would be Sandhill Road. And now it's more distributed, but still It's a thing. Yeah. Oh yeah. If you go stay at the at the Rosewood and you're right around the corner, that's got its own stories. That's a strange place. But Fantastic. Fantastic. And then you have

1:15:12 You name it, right? Everybody's there. All the big players. And so that's the Sandhill shuffle. So why not be afraid to lawsuits? What did you guys know that the guys who said, nah uh uh I'm not gonna touch that with a ten foot pool. Well the founder CEO Mark Britton Was my general counsel at Expedia. And he worked.

1:15:33 Securities commission prior to that. He was a real attorney. Mm-hmm. And the way we did it, we were one hundred percent convinced of our legal Grounds. Yeah.

1:15:42 And so people could still just consume so much energy, right? No doubt. So we raised money to deal with that, but we knew it was gonna be pretty cheap losses. And we could provide the legal most of the legal billing ourselves anyway. And so it would be cheaper than hiring some fancy firm. We were convinced and You know, after we won the first few suits, you know, they lost steam, the lawyers lost steam on suing. So it caused some venture capitalists to not do it, but the more kind of disruptive oriented folks were like yeah, great. So what happened with that? It did pretty well. It did pretty well. We had trouble so in a kind of trip advisor for legal

1:16:19 uh sort of way. It did really well. Ultimately These kind of trip advisory middle digital middlemen who were kind of SEO on one side. collecting Google search traffic on one side and trying to monetize leads on the other. You know, as time wore on, a lot of those business models got Somewhat disintermediated. And so the protection against that is

1:16:40 Usually to go down into the tr workflow of the transactions of the of the industry, which is say what we've done at Zillow. Or what Expedia does. So could you explain that just one more time and maybe an example would be helpful. So let's just say there's a trip advisor for X. Yep. Like you said, they're kinda harvesting traffic on the SEO side. So their pages are engineered in such a way. That's right. Maybe also using ad spend to drive traffic. to these reviews, which are then monetized on some level. That's right. Some people get to see but by selling those leads out the other side of the marketplace. Right. So literally a lead middleman. You got it. Yeah lead. How would they get disarmed intermediated Michael Porter Five Forces would say

1:17:21 Look, if you have an over dependency on any supply of customers, you're strategically exposed for obvious reasons. You go if you have an overdependency on any supplier. Yeah. You're strategically exposed. And so Business strategy one oh one says diversify your sources of customers and your sources of supply so that nobody gets too much leverage over you. Okay, well also it's like a single point of failure, right? If absolutely factory went down because of XYZ. That's a problem. We're dealing with that right now in the country because COVID discovered that we had lots of You know, supply chain single points of failure. Anyway, we don't need to sidetrack on that. Alright, so in that example

1:17:57 If you're primarily getting your traffic from Google, Paid or free. You're developing a serious dependency on Google. And Google, of course, in its own search for increased value starts looking vertical, which means down into your business.

1:18:14 Yeah. And so People probably noticed over the years that Google started doing reviews, and then they did their own mess. So they're doing their Yelp reviews and their TripAdvisor reviews, and then they started doing airline schedules and hotel bookings and restaurant reservations and and and so when the big guy that you're getting all your customers from starts Taking a more than passing interest in your business model because they want to capture more value, you better figure out something else. Yeah. Okay. So strategically speaking, my defense against that in my digital marketplaces has been twofold. One Build a giant brand.

1:18:48 The customers know. Mm-hmm. And love. And therefore most of your traffic and customers comes directly to your app and sites. Okay, you have to have a brand to do that in order to have power. And then two, look down your funnel and look into the workflow of the business you're in, be it

1:19:05 Travel or real estate or legal or jobs, you know, through for the verticals that I've done stuff in. And make sure you become digitally integral to the workflow. You you're building tools for the industry. Mm-hmm. Ultimately, maybe even doing the transactions. Okay, and having a platform for the transactions. And that in a nutshell is what Zillow's long term strategy is. We're basically building a super app, a one-stop shop application for anybody who's renting or buying, soup to nuts, everything integrated.

1:19:37 All the professionals plug in and workflow. And that We have a big brand, we source almost all of our customers directly. Not all, but most. And were embedded in the workflow solving real customer problems and The business is great. And draw.

1:19:53 Alright, so I haven't forgotten about the provocation marketing class. However Okay. I think this is a great place to buy you some more time and talk about naming. Okay. Oh, how do you how do you name company? You saw that live post. I played around with blogging like all of us. You know, some it took it really stuck with some and it didn't with others. I probably only had like ten posts on my blog. But one of them was naming,'cause I've I've had a lot of fun naming companies. Mm-hmm. And I gave advice on naming I think the title of the post The site it's on is called hopperandropper.com, which is a fly fishing term. But which is nobody's gone to, so I only had twenty visitors. Tim being one. Lucky twenty one

1:20:35 I have a few rules about naming. First when you're trying to brand a company, if you're building a consumer brand especially You have kind of two broad ways you can go. The easy way and the hard way. And I'll forgive the four hour work week and the four hour body.

1:20:51 You know, but I'll tell you that there are no shortcuts. You take the shortcut to the long road, my coach Jimmy says. Yeah. Anyway. The easy way is if you're building a travel site to call it hotels.com, airline tickets.com. You know, you name it. Every category has a literal word dot com. And the advantages to that are it's easy to explain to people what you do. Yeah. And the disadvantages to that are you don't own any brand equity. Because you can't own a word that previously exists.

1:21:17 And so you're non distinct and non distinctive. There's an in between way. Which is to use an existing word but make a new application of it, Apple. Computer. Amazon dot com.

1:21:28 And that's viable. But you have to build a new definition for that word, which those companies obviously did successfully. The hard way and the best way, I think. for consumers is to make up a word. Make up a word.

1:21:41 Which is super hard because you have to tell people what the word means. You have to define it for them. But once you do, you own that word. The definition of that word is yours and only yours. And so I like the hard path because I like building brands. And with provocation marketing, I think I can get a big audience early, which begins to familiarize people with the brand. So I'm was confident my ability to my my team's really ability to do that. Okay, so now when you're making up a word, what do you do? And I think this is what you're referring to. Okay, so high point scrabble letters. Do you play Scrabble? Okay, you know that there are different

1:22:18 Point numbers on each letter as you play scrabble. And Do you remember what the high point ones are? I don't. Okay. There Z

1:22:27 Is ten. X is ten. That's the highest points you can get. A E I O U are one. Here's why. Q is ten to. Here's why. Z, X and Q are super rare.

1:22:39 Letters. Mm-hmm. A E I O U are super common. And so rule number one is Pick the super rare letters.

1:22:47 And pick them because they're very distinctive. They jump off a page when you read, they stick in people's brains in a way that's not crowded. Mm-hmm. So All my stuff has Z and X's and some Q's actually too. Uh rule number two, fewer syllables is better than more. I kinda learned this lesson with expedia.

1:23:04 Expedient was uh too many syllables. It worked. Oh fine. We've overcome that. The company's overcome that now, but it was in hindsight was a lot. I liked it because of rule number three, which is it was evocative of positive thing speed. Expedition.

1:23:20 So it it said adventure and speed and that all felt good. Yeah uh in that word. But fewer syllables. I think two syllables is the sweet spot. Because I also want it to be a good dog name. So if the word could be a good dog name, you're on to something like you can call for it. Yeah. Zillow.

1:23:38 Yeah. Anyway. Another one is it can be turned into a verb pretty easily. So pick a word that can be turned into a verb. So it's probably A dog name and verb probably means it ends in a vowel sound. And then the last one is people, double letters and palindromes are good too. So anything that is unique, a unique word form. Double letters people remember they jump off the page and palindrome are Words that are the same forward and backward spelled. Right. So just interesting, interesting words. Yeah.

1:24:05 Anyway. That's my handbook. Palindrome like my friend Mike Kemp back in the day. I was struggling to think of one, I couldn't pull one on the fly. Taco Cat. It's a good game. So you're in the game station. That is a funny game, isn't it? So stupid. So fun. That was so good. So I'm thinking of Double letters. So there are names Expedia had X. has an X. X speed. Good connotation with pre existing words or concepts. Yep.

1:24:37 Maybe one syllable too long. Then you got Zillow. Zillow kinda named it. I'm imagining this Labrador retriever, right? Yeah. And starts with a Z, like what how many words start with a Z? That's great. And two double letter L Lft ending. Double letter, but I'm not sure because I've I'm not disputed with my

1:24:56 Scrabble glass door. Last door. In the middle. Yeah. pretty evocative of having people peer is transparency. Power of the people and transparency is a big thing. We really liked kinda

1:25:10 Looking in through the glass door inside of a company. Two syllables, not a great dog word. You know, but two double letters. So it kinda jumps off the page. It's an interesting looking Word. I would say we get a kind of a B on that. No but Robert did a very good job with marketing that so

1:25:28 All right. So If you need more time. I'm not gonna forget about it. The provocation mark curriculum. Yeah. And it could just be one seminar. It doesn't have to be ongoing. Just if that complicates the the envisioning process.

1:25:43 Find a seven deadly sin zone, something that is emotionally core to us. Okay. That you know is gonna incite an emotional response. All right. Okay. So some topic that people are emotional about. And then Go address some

1:26:01 Sacred cow. You know, some taboo. Or Sacred Cow in that space. Most of the ideas that you could probably think of with that outline would be really negative. Mm-hmm.

1:26:12 And then get rid of all those because I do believe a cheap way to get attention is to scare people. Okay. But I think it's cheap. It's a cheap way to lead. Is to scare people. Effective, but cheap.

1:26:26 And it doesn't make people feel good. To be scared. So if you're building a brand and a service, you want people to be Provoked? But feel good.

1:26:38 Or Tickled or entertained. You know. And so that is where I would head with the seminar. And then we End up brainstorming about getting people's ideas for that. Let's touch on briefly mentioned Bill Gurley.

1:26:51 Of course, famous venture capitalist, he's been on the show. Brilliant guy. Also quite hilarious. And local. And local.

1:26:59 Yeah, yeah, he's right down right a couple of blocks from where we're sitting right now. You have spent time at Benchmark Capital, which way back in the day, I mentioned this to Bill when I first moved to Silicon Valley. A book was recommended to me called E Boys way back in the day. Exciting. And putting aside how Bill may or may not feel about it, we didn't really get into it. I'm sure there's lots of stuff that could stand some fact checking, but it was incredibly inspirational. And so entertaining. I mean this was the heyday, right? I mean this was just

1:27:29 Rocket ships everywhere. So fun, right? So you've spent time Yeah. Benchmark. What?

1:27:37 Led you to that. Was that kind of biding time until you figured out which next big swing to take? What was the motivation? And then also What did you learn there or what came into Greater resolution or clarity while you were there. Yeah, okay.

1:27:56 So As we chatted about before when I was coming. With my family back from Sabbatical. I'm a big believer in the sabbatical.

1:28:04 In Italy. And was considering the next Career. Move. I got to know.

1:28:11 First Bruce Dunleevy and the at Benchmark. And then Bill and the other guys. I did read E Boys then too, which was you know. Romantic kind of in a in a weird way, but you know for business geeks like me and you maybe romantic. And I also knew that I had a personality that did want to have my fingers in a lot of stuff.

1:28:31 Mm-hmm. Yeah. I did, I knew that. I like to do lots of things and I wanna do lots of things and I could do lots of things. I could think about lots of things. And so

1:28:41 In the course of trying to figure out prior to Zillow. Trying to figure out what to do. I got to know those guys really well. You know, they invited me to a bunch of stuff to sit in on stuff. I knew I would be good at that. I knew I liked doing that. And then a condition with Llo Frank of doing the Zillow thing and taking the CEO title, I said, Look, you know I'm gonna

1:29:01 Do a bunch of other things too. I'm gonna start more companies and And I'm gonna do the venture capital thing and he's like, Oh good, no problem. And so As a way To keep myself stimulated and seeing lots of stuff and get down to the valley. I was in Seattle, which was not really a venture. Pop Ed.

1:29:18 It's time. Cloud computing hadn't happened yet. We did have Amazon, Expedia, and Microsoft, but you know, and so the action on the cutting edge was down in the valley. I had some boards I was on down there as well. And so I took the venture partner job with benchmark, which is a pretty ill-defined position. As a way to

1:29:38 Keep me going to the valley and keep me in the flow of the latest stuff. And I really loved that. I do believe that ended up benefiting all the other stuff I was doing as well. I really love that you know, love that team. I love that team to this day. How did it benefit the other things? Was just seeing around corners, kind of getting an idea of what's coming before most other people have a chance to Yeah, and and thinking of new ideas for companies too. But I'm a big believer

1:30:04 There are some companies that hold on to their people and say you can't go do other things. Don't sit on other boards. I really like Executives that are on my teams. To have another port. And

1:30:16 If you love it, set it free. If you're scared about losing people and you're being too retentive, that means you're too insulate, probably. And You gotta give the get. If you give time and get interested in other business models, you help them. But you end up learning a s a bunch of stuff for your own. Company. I've learned so much from sitting on the board of Netflix that I've imported to my other companies. Can you explain, just for folks who may not be familiar, what does it mean to sit on a board?

1:30:42 What does that actually mean? It depends board to board, I'm sure, on responsibilities and expectations, but Along with that. You must have lots of requests to join X, Y, or Z boards. How do you choose? the boards to be a part of. Okay. What it means to sit on a board is when a company's private It means

1:31:03 Help. The CEO and the leadership team build the company. Mm-hmm. Okay, so it's really being an advisor and a coach and somebody with a lot of business building experience. Two

1:31:16 Help. Pick the right strategy. Not don't you're not running anything, but you're basically coaching the entrepreneurs who oftentimes are less experienced. Sometimes not. But oftentimes less experienced. And

1:31:28 I would always recommend assembling a board of people with real experience who gonna be engaged. And so it's a company building exercise. And then when fundraising it's time to fundraise can s totally help with the the next fundraising. Can help with recruiting. at this is I mean, there's so many good ones. Bill is really good, as you've seen in the Uber case at really helping c build companies. Okay. And a public company is a little different.

1:31:51 Yeah, I had one thing and I've never been. Than on a board, but Yeah, no, I've dodged it, I guess, in a sense. So you have a negative impression? No, no, it's not a negative impression. Um You dodged it. Well, I feel like Yeah, dodge is a strong verb to use. I felt like I at the time when these opportunities have come up.

1:32:13 That I did not have clear criteria. And I don't want to commit to things reactively. Yeah. Which is part of the reason why I'm asking you. Okay, got it. And also it seems like, and definitely correct me if I'm wrong, but another responsibility of a board is to fire leadership if it comes down to that. So it can be better roses and looking forward to the future and a lot of good things, but it's also It also comes with responsibilities to handle the tough times. And that's those are probably the most especially for a public company, those are the most important times too. Yeah.

1:32:47 When you're company building As a private company, it's a little less important. Yeah. That's good context. But it's something that I've been uh not necessarily reconsidering because I've I think you should. I think you'd be good. Okay, tell me. Well you're a coach.

1:32:59 Yeah. That's all it is. Okay. I mean it's what it's what it primarily is you're instinctively a coach. And you have a lot of experience sets and you look for look for analogies, you look for, you know, oh, this situation here is a lot like this other situation, and that that makes you a good communicator and that

1:33:16 It's I kind of in I shouldn't say inadvertently, because it's not inadvertent, but informally do that already, right, with a lot of the founders that I'm involved with. Which is fine too. But it's that same. In the best of circumstances.

1:33:34 It is that same way on a board. Mm-hmm. Okay. And those are the only boards that I'm involved with is is those that are really there. Two Coach and give advice.

1:33:44 Sometimes Oftentimes. in a public company when you get into the public markets where your responsibilities are a little different. Yeah. You have these hardcore responsibilities to represent shareholders.

1:33:55 And the only real power you have is kind of capital allocation a little bit, and who's the CEO? Capital allocation meaning how do they spend Raising money. Raising money. Spending money. Usually not to the budgetary, but big big acquisitions, whatever. Big changes in the cap.

1:34:13 Table in the balance sheet that will affect shareholders. Okay. Got it. Oftentimes public companies, depending on their age, usually as they get older, they stop acting like a private board where it's really about the strategy and coaching and helping and building and then becomes more about Institutional shareholder services rates directors. What is that?

1:34:33 Oh wow. Okay. So they're like the lawyers competing to have good ratings on Ava. Kinda. Okay. Kinda. And then when a board This is something I haven't heard anything about. If a board tips just if a board tips into let's call them professional directors who are really worried about their board director reputation It becomes more about them and process and CYA. Cover your ass. Yeah, because you don't want to get sued, whatever. You don't want to look bad, whatever. Versus let's build a company. Yeah, that doesn't sound fun. I've really actually never had a board tip into that.

1:35:04 That some boards evolve into Finger pointing and and what have you, but in the private space, right? Yeah. So I'm on a few public boards, but they're all really their strategy and how can we grow and how can we help you and how's the team doing? And and so

1:35:20 If I don't get a good ISS rating, which I have some of the worst there are out there Um Wait, wait, who who actually determines the rating? I don't really know the process and I don't really give a rip, but it's some survey. It's got stick up job these things. They they uh stick up job like give us what we want or else look it's like bond ratings or whatever. Like these ratings firms

1:35:43 They do ratings and then they sell consulting services to the customers. It's just a classic. You know. And mutual funds and ETFs, whatever hire them and you know, they can't track every company, so they look at the ratings and how we should vote on the proxy issue and blah, blah, blah. Anyway I I've got very low ratings for lots of Nonsensical reasons. But I don't care. Yeah. Yeah. Okay. I personally don't care.

1:36:08 But uh a a lot of the a board that's full of directors who really do care is like not as you know as fun. Framework for you. Which you you asked so Greg McFay, who's on my board at Zillow and who I've worked with for a long time, I mentioned already. And Jay Hoag kinda gave me the same advice. Jay's another venture capitalist who I work a lot with. We're on boards together. Construct. A good construct that Greg told me early in my career was is it

1:36:34 Local, is it fun? Is it lucrative? Yeah, those are good place to start. So you don't want to you don't you can zoom now a little bit, but you really don't want to spend your life. So that's another thing that put me on the sidelines is I knew a few people who i they just seemed like traveling Salesman in the sense it was like George Clooney from Up in the Air. When he's just traveling around a different city every yeah, you know, every other week. Soul crushing. Yeah. It's not quite that way, but yeah, I mean

1:37:06 So local is Greg when he laid it out for me, he's like It's gotta be two out of three at least. If we can be all three, tri effector score. And lucrative meaning potentially lucrative. Like the businesses you would buy the stock. Right. As a gross stock. You know. So and and this is as good a point as any to just explain the I guess compensation structure. How does it work? You get an equity grant, you have options to vest over time, and then I suppose it depends on the state of the and stage of the company. But

1:37:33 Private companies often are not compensated because you're the venture capitalist. Right. Okay. So you're the funder. So you're doing it because you've ha already. You already own a chunk of the company. Yep. So that's your compensation. And most startups, most Private companies can't afford to Okay.

1:37:48 Now the late stage startups, the forever startups now, like I'm sure stripe directors make a lot of money. Public Companies You know, it's really just like Salary bands based on the size of the company. I mean it's like for most

1:38:02 Kind of mid cap. public companies, I would guess it's two hundred to three hundred fifty thousand dollars a year. Most companies for big meetings, committee meetings, whatever, not a huge chunk of time. You know, so it's nice. And then usually they Enable the directors to choose if they want it in if some part has to be in stock.

1:38:22 And some could be in cash. You know? Anyway. I had a ton of experience with those. So Fun, local, lucrative. Potentially lucrative. Potentially lucrative. And fun fun has gotta be like

1:38:34 It's a proxy for maybe it's a cool company, whatever, that's fun, but really it's the boardroom dynamic. Mm-hmm. You look around the table and at the leadership team and are these Interesting. Is it a collegial Everybody's rowing together in the same boat kind of situation, or is it a

1:38:50 We got old factions fighting and this these guys want that and these ones want that and like you know run away. Less game of throne. Yeah, exactly. Like no fun. No fun. Alright, so We're drinking our carbonated Japanese citrus, yeah. Use your coconut water.

1:39:08 Feeling very Infused. Well hydrated and infused. And that is as smooth slash awkward a segue as possible. Two Do a callback to something you mentioned earlier, which was da da da da.

1:39:22 And then I started paying attention to things I had neglected before that and Including Health and body things like that. So when Did that happen? Was was it a gradual

1:39:37 Development of Wellness habits, self care, or was there a reckoning? At some point, what happened? Yeah, I mean I think a for a lot of people it's a health reckoning for them or For somebody else.

1:39:51 That kind of Shocks them and uh You know, and maybe an overlay of general age. You know, the the substrate is age. Yeah.

1:40:00 Ultimately everybody probably figures this out. Some later sooner than others. What is your age now? I have no idea. I can't tell. Fifty seven. Okay, God. Yeah. Wow. Yeah. Really held on to the youthful glow. Everything's falling apart. Oh god. American history acts as of ten years ago, and then it's just the crow's feet are turning into Crow's legs. But you seem to Be very active. I am and it was for me it was that same

1:40:29 It was a Catalyst. It was pretty sudden. External catalyst, not my health. But My wife's and children's

1:40:37 And So my I have three kids. Will, Josie and Russell and Josie and Russell are twins. And twin pregnancies are High risk.

1:40:47 Definitionally. And so I was age maybe thirty five. Thirty four. Running.

1:40:57 Experience. As a really young Public company. CEO. The company's doing great, but I like had to deal with stuff like nine eleven, you know? Yeah during the

1:41:08 In the travel business. And I had been a Pretty like Not s quite sleep under the desk, but kinda work all the time kind of guy for a long time. Like we all kinda Yeah, we socialized with Microsoft people and then Expedia people and we just lived this was our lives.

1:41:26 We talked about it at dinner. So I was pretty neglectful. While I was a weekend warrior type basketball player and tennis player. And snowboarder. I didn't yet realize that I had to maintain myself in order to be able to do those things.

1:41:41 I was just working too hard. Working all the time. When Sarah was pregnant with Josie and Russell, she went into labor really early. We were on our way up to Whistler. And she was

1:41:54 For those who understand these things, I think she was twenty seven weeks. Pregnant out of a forty week typical gestation period, which is very early. That's not very, very early, but it's danger early. Like And so We were driving.

1:42:08 On our way, so I was like, I think something's going on. Let's go stop by the hospital. So we stopped by the hospital just so sh so her OB could check her out. And she was like Partially dilated and like Yeah. And

1:42:23 Sarah thought nothing of it. You know, the shoemakers' kids have no shoes. Sarah's like, Oh, fine, I'll just keep the seat reclined as we drive up the Whistler And her her doctor, Edie Edith. So not only are you not going up to Whistle, you're not going home. You are gonna be admitted to the hospital and we're gonna put you on muscle relax and so that began at kind of a six week very scary period of my life and her life where she was in the hospital

1:42:48 Making sure that the babies didn't get born. I was taking care of my Three year old Will And Then everything turned out great. She carried them to

1:42:59 Thirty five weeks or something, thirty six weeks. Kids are perfect. The birth was a little hard, the kids were perfect. And it all worked out, but in the course of that period of time it got me to reassess My life and how I live my life and what my priorities were and how I

1:43:13 You know, I needed to take care of myself mentally and physically. I kinda had the realization that for sustainability I was gonna have to start doing a bunch of things If I wanted to do the things I love to do for the long term, I was gonna have to really build my foundation. I decided to quit my job at that point too. I was still CEO, I see had just acquired the company.

1:43:33 And I made the decision at that point, but that this lifestyle Was not. I didn't need it. Need to change.

1:43:41 And What were some of the Changes. Like how did you layer things in? Did you boil the ocean all at once? And I was like, all right, here are the twelve new things I'm starting. Did you layer it in? And Would you have done anything differently?

1:43:56 I started just exploring things. The big change was we moved to Italy six months later. Or maybe Eight months later.

1:44:04 And I developed a whole new set of things I did when we were living in Italy, like I took up road biking, which is a very Italian A social Italian thing to do, which was great. Was great for making friends too. But I had a period of time after that where I was in Seattle and I started You know, I remember the first real class of kind of thing I'd ever done was hot yoga. And I was like, Wow, this is amazing. I feel incredible after I come out of that class and it's you know

1:44:29 Strength and some conditioning, I guess, and really interesting and kind of a mental thing too. I started doing that. And then I I didn't I hadn't didn't hire a trainer until much later, but I eventually I eventually got there. I didn't lift weights for a long, long time. I was more just kind of Running, I took up running. I ran a couple of marathons.

1:44:50 You know, I discovered my body was not built for my joints were not built for marathons. Anyway, I d I did a I did a bunch of things, Tim. recognizing the I felt better when my body felt better. And uh My mind felt better when

1:45:04 My body felt better. And It's just built over time to the age I am now where like The physiology of what's happening to my body and my bone density, my muscle mass at my age. It's like I'm like continually been ramping up how much I do. A because it makes me feel good, but B because I'm you know

1:45:23 Just Agewise deteriorating. And if I want a snowboard, I've snowboarded thirty five days this year. And it's been amazing. And like

1:45:32 If I wanna keep doing stuff like that. I've gotta be strong. Mm-hmm. So what does the current regiment look like? Generally speaking, I'm sure there are exceptions and maybe travel or go to various places, but what does the general regimen look like?

1:45:45 Probably a couple hours total of zone two y type stuff, you know, bike. Growing. Maybe tread. My knees kinda are not great running, but the treadmill a softer treadmill works. But the Peloton is my favorite one there. And then

1:46:01 Weight lifting. Different Body parts maybe four times a week. Mm-hmm. And then a lot of just play stuff.

1:46:08 You know, A lot of snowboarding and again uh sports play sports. Yeah. Yeah. I play tennis. I like to do a lot of stuff with my body in the world. Yeah. How do you fit that in? I mean you got a lot going on. You like building, you continually, as our mutual friend Chris Saka uh has in one of his one of his suggested topics for exploration since I asked him. Like you continually put yourself back in the arena.

1:46:33 Yeah. Right, as a builder. Yeah. You are on several boards. I mean there are Demands. I'm sure there's a lot of inbound that you say no to.

1:46:42 How do you think about the self care? Is it sort of the first thing that you block and then That's it. For me now priority wise that is Me my family and My health is essential to my family's health too. So

1:46:55 My family and my health and my state of mind. But I am not operating I but Seven, eight months ago I after my Second or third stint as CEO at Zillow. I kinda kicked myself back upstairs.

1:47:08 And so I'm no longer the day to day CEO. Which is terrific. It's helped. But I've always been the guy who uh my joke was I'm very much a delegator. I'm very much a pick great people and then give them lots of space.

1:47:22 And actually a a a leadership development technique I often coach Is for a senior leader or middle management type leader I encourage them to really take a vacation and disappear. And most people think that's gonna be harmful.

1:47:37 to their business or their career. And what I try to coach them on is no, that is actually the way You develop Your leaders one of the ways you develop your leaders because if you're really disconnected You're on a surf trip.

1:47:50 In Indonesia and you had zero connectivity. For how long it's like. For two weeks. Yeah. Okay. Do it for two weeks. And be disconnected and your teams are gonna have to figure out how to deal with stuff that's important. And they're gonna have to create systems and policies and rules ahead of time. That will Outlive the surf trip.

1:48:09 That's true, but from a leadership perspective, sometimes the real leader of an organization is not necessarily the one with the title. Yeah. And when Somebody's really disconnected. The senior leader is disconnected. Leadership is sort of an emergent property.

1:48:25 Okay, and it it kind of emerges. So This is a long way of saying I kind of have always felt that way about my universe too. I believe the most Secure people are willing to let go. and roll the dice on the other people and answer the question, who is your successor? If you were hit by a bus, who would take over? Okay. And the less secure people, the more insecure people

1:48:49 put themselves in a position where they seem indispensable to senior management and couldn't possibly leave. Okay, that person is not promotable. The person who has cultivated leaders under them, that person is totally promotable, even though That person's more expendable, too. Yeah. Right. And so it's that fine thing. Long winded way of me saying I've always had a lot of things going on, and my joke was

1:49:10 You know, if I'm doing my job really, really perfectly, I can be on my surfboard. Okay. And nobody knows when you don't show up to work if you have eight jobs. Everybody always thinks you're working on the other thing. I'm being glib and it's kind of gets it gets a little bit of a chuckle, but it's I I am uh seriously leverage oriented person.

1:49:32 So it's not that hard. You identify opportunities for leverage or think about leverage. In a life context, it is just Surrounding yourself with great people who care.

1:49:49 Who have skills and who care about whatever the mission is, be it building a business or building a family. Like Sarah is Amazingly Smart and capable and cares and like The stuff that she's in charge of is gonna happen well.

1:50:04 You know, that like that's an unbelievable feature to have in a partner as you're looking for a partner. Yeah. You know. Uh lots of stuff matters in finding a partner, but like It's really a partnership. If you guys are gonna have a baby, that's a business of sorts. You know? I think it's mostly about picking the right people.

1:50:22 Any recommendations for people who Or Hiring folks they have not known for a long period of time. Any recommendations for The hiring process.

1:50:36 'Cause a lot of people interview well who don't necessarily perform well. They know what to say. And reference checks often are conflicted. Reference conflicted. I've had the worst luck with taking reference checks at face value. There's some ways to kinda work with that. Yeah. Two things.

1:50:52 I would say. One is my favor my favorite section of the resume, I guess now LinkedIn. It's not really a section on LinkedIn, but is always in the very bottom, which is the interests. Mm-hmm. Okay.

1:51:04 And I want Sure. Get somebody if in an interview situation talking about their interests and why they put them there and then just

1:51:15 Asking them basic questions and watching Whether or not they have any passion. Yeah. Just to see a real spark. Mm-hmm. You know,'cause if they put it there, that is what they're interested in. And they'd better be able to light up on it. When I was earlier in my career, I'd I would always make up business cases around some interest, you know. How big is the ski industry? Because you put skiing, whatever, you know, and that was always a fun stepping off point.

1:51:37 So finding people's pass I wanna find people who are passionate people. And then the second thing is get used to Pulling the pitcher off the mount quickly. Firing someone. Yep.

1:51:49 Okay. It's hard when you're early in your career. It's not as hard later. All of my mistakes As a leader.

1:51:58 Have been leaving Almost all of them have been leaving the pitcher on the mound. Too long. Hoping that's The arm would get better.

1:52:05 What have you learned in terms of Process for firing. Any Approach. Go to phrases.

1:52:14 rules. If you've got someone you're going on your two week surf trip, there's someone below you who is going to fill that Leadership void and he or she is gonna have to fire someone. And they're like Hey boss. I don't want to bother you, but this is something I haven't done before. Yep. Give me some advice.

1:52:33 Don't do it via text. Be an upstanding person. You know, have some courage. You gotta be face to face. But it's actually not that hard. My advice would be

1:52:43 Look. If you're not happy With the performance of this person? I guarantee you the person isn't happy either. Therefore you can increase love in the world by releasing that person to find where that person belongs.

1:52:58 That person belongs somewhere else. That person's gonna be happy somewhere. Help that person find that somewhere. But you're gonna be happier when you release that person, that person's gonna be happier too. And so if you make it a partnership, if you make it a joint decision effectively, or at least align get the interests aligned, which it Almost always is.

1:53:16 It's not as hard. And when you do that, you naturally are being human. If you're looking for shared Alignment. That means you care.

1:53:26 That means you're showing heart. And having heart in this situation is s really important. And then in terms of the delivery. The conversation. Any tips on how to manage that?

1:53:38 You do have to be ready for A lot of stuff to come up. And As the person in the power holding power in this situation, you have to wear it. You have to understand and be

1:53:49 Sympathetic and non argumentative. In order to get people on the same page. Well, oftentimes just like in life with anything. People really do need to get it out and be heard. And that's great. That's great.

1:54:02 And then asking advice on the way out too, like For voluntary or involuntary termination. Sometimes it's hazy, right? You know? And Soliciting information on the way out. For yourself and the organization is often appreciated and often revealing.

1:54:17 Two. So that's good. Exit interview. Exit interview is important. In a As casual a setting as you can make, as you can muster. I believe the entrance the one month

1:54:29 Post. Start is a really great time to get observations from new people too. They haven't been fully indoctrinated yet. And they probably are good consultants. Right then.

1:54:39 Mm-hmm. So Random question. I don't know. You could be covered in tattoos, but what is the story Of this tattoo. Family.

1:54:49 Alright. Five of us in the family? Things we love. So it looks at a quick glance looks like a snowflake, but Those are trees. It's made up of five trees.

1:54:59 It's a snowflake in total shape. And it's a starfish in the negative space. Uh-huh. My daughter Josie When she was sixteen?

1:55:08 Which is too young to get a tattoo. Yeah. Sarah? If she could get a tattoo. Or asked her more specifically, would she get a tattoo with her?

1:55:18 Mm-hmm. And Sarah's like Well you meant sorry, like sharp. Ha Okay, well let's design one as a family.

1:55:28 Yeah, no Wiley Coyote. It the first version do you know those uh on the back of a minivan, the family of five with the stick figure mom and stick figure that was what Josie drew. That's Josie's very creative, you're you're creative, honey. But it was funny, that was the first version and we You know, we were Sharing. different versions and iterating and at some point Sarah said

1:55:51 Maybe we should bring, you know, this artist friend Joe Park into this and he'd never designed a tattoo. We brought him and he was super psyched to do it. So then he led the creative iterations and we ended up with we ended up with this. They they look exactly the same, but they're not, they're all unique. They form a Oh, the trees you're saying. The trees are unique too. Mm-hmm. So Anyway.

1:56:11 I dig it. Yeah. I love it. I was the only one who got it in a really visible place and everybody else got jealous because I like to be able to look at it and rem remember my family. And We did this maybe. Five, six, seven years ago. I thought we'd get

1:56:26 More? Sarah's gotten two more tattoos, but I haven't gotten any more. You know. I think tattoos are you don't have any? Do you have some? No. It's a it's a Very few people have one. Yeah, I have been uh I've been considering getting my first which is is in some ways Kind of similar. It'd actually be in Very similar location, right here with my dog's paw prints.

1:56:48 It's hard for me to imagine. Regretting that. You won't yeah, I don't think I will. Yeah. Yeah. Yeah. Uh so We uh it was interestingly

1:56:57 Our older boy Will was of age to get a tattoo. He was eighteen, I think, at the time, maybe nineteen. But the twins It wasn't legal to get one in Washington State or most states. And so Josie was actually going to high school for a year in Spain at the time, and Spain didn't have that restriction. So she got the design and got it. Got it in Spain.

1:57:16 And we have the house in Montana. And Montana doesn't have any restrictions, so On the way to go skiing one time, Russell, you know, went to some sketchy place in Bozeman and got the tattoos, and we got'em all we all got'em in different places. It's funny. Any other uh I mean, I guess n getting a tattoo is not necessarily a recommendation you're making, but Any thoughts for

1:57:37 Let's just say there are people listening who are Type A or otherwise builders. Consumed perhaps by the scale and scope of what they're doing or hope to do. And they're

1:57:52 Planning on kids or they have very young kids. What would your recommendations be to those people? For the planning on the the kind of Costant. Delayers. Which there are a lot of

1:58:03 Yeah. Uh uh out there. Yeah. Okay. And I think the fundamental logic Is this is an important thing and I don't have enough time. Yeah. Right now. And so I'll wait till it's a better time. Mm-hmm.

1:58:20 There's never a better time. Yeah. There's never a good time. So point number one is It's not gonna get better. It's not gonna feel better.

1:58:29 And then point number two is We're built for this. Yeah. We are the successful evolutionary product of A lot of people who figured this out

1:58:43 Which means We have a lot of encoded knowledge about how to do this and how to deal From our bodies and our minds and our relationships and even just how we parent. It's encoded. A lot of it is encoded. So it's you know what? It's probably gonna work. Pretty well.

1:58:57 And so I don't know if I call myself a birther. I'm an encourager of like Plus have more babies and I'm a really Big believer in how it's such an important part of our own mental health. To have At least for me. Yeah. To have children and

1:59:13 From a Growth perspective and it kind of As we get older. Ego focus naturally, the diameter of our ego sphere gets broader and broader and children just Blow it way out. And that is

1:59:25 Really a positive for most people to realize that their needs and wants are trivial. You know? I think that's a positive. So anyway, I I encourage it. Yeah, for me it's not a Bad timing, looking for better timing thing. It's more of a navigating the bizarre aspects of modern dating being in my Public slash semi public position and

1:59:50 As someone who's already for a lot of good reasons slow to trust. getting to a point where I feel like I can pull the trigger. I think that's solvable, but it's it's not trivial. It's I didn't have I never had to deal with that, but I totally how how old were you guys when you met? Twenty two. Wow. Yeah. In a pub in Cambridge, Mass?

2:00:12 Think of that. Yeah. Maybe that's my next move. Pub crawling game. Um it's hard. For the uh the people with young kids, like And balancing things.

2:00:26 I guess I would just always advise to don't wait for an external catalyst to make sure you're prioritizing your Family life and your personal health. 'Cause a lot of people out there are not doing that. And Eventually Comes home to Russ one way or another.

2:00:42 You know, and the sooner you can kinda Keep things in perspective. It's a it's kind of a confidence game in general. It's a courage and confidence game in general. If you have High confidence In your abilities, there is no better time for at least

2:00:55 You know, the kinds of jobs in the sit at a desk, use a computer type job. There's no better time in the history Of the world. To be able to have a good balance between having work and life interweave. I'm a huge believer in what I call cloud HQ, cloud headquarters at Zillow. Post pandemic. I was a huge believer in office culture before that, but the pandemic opened my eyes to just how much more inclusive.

2:01:20 The Cloud. Headquartered The Matt Mullenway. Matt was very you know, he was very influential on me early in the pandemic. Mm-hmm. You know, I had him blue jeans.

2:01:31 zoom in to an early company meeting early in Covid and lay out his Game plan. For the distributed corporation. Mm-hmm. Yeah. People who don't know. Yeah. Super helpful. Yeah, Matt Mullenweg. generally associated with WordPress.

2:01:46 Founder and CEO of Automatic spelled M A T T I C. and pioneer of distributed workforces. and uh as a design principle from the outset has built that company. To be distributed. And therefore was very

2:02:04 anti fragile when Covid came along. And there are some other stand out examples. I mean Shopify did really well. Yep. Also. But you're right. I think If this can't lend itself, I mean modern technology and the options available.

2:02:18 To some type of balance or the option to pull different levers where it would have been far difficult. Even ten years ago. Yeah. We can generalize and say it's been great for moms, but it's more than just moms. Like you know But it has enabled

2:02:34 Really smart. very experienced moms who may have historically decided to take the off ramp into primarily momhood rather than primarily climbing the corporate ladder or just executive leadership. Uh it's it's enabled them to come back. Yeah.

2:02:51 And likewise now. For a father, like As long as the company doesn't Get angry. When they see you in your car on the Zoom.

2:03:01 Because you're at a dentist deployment for your kid or something. You know, as long as like that doesn't make the CEO get angry because that's not the way I did it when I came up and look how great I turned out. You know, like I've got to do it this way. It's like I kinda chuckle when I listen to all that. I'm like You people, like open your minds. Like this is just this opens doors. This doesn't close doors. Yeah. So let me ask a couple of quick questions.

2:03:26 Yeah, they don't need to have quick answers, but just as we start to Line the plan. What books have you either Gifted a lot to other people or re read yourself. Either one.

2:03:40 I am Not your typical person probably sitting in the seat and that Maybe yeah. I am not a nonfiction business book

2:03:51 Sorry, Tim. And I tend not to read that stuff. So the older I get, I occasionally will read a biography now, but they mean more now the older you get. But I am fully a I'm a big reader and it's fiction. Mm-hmm. And generally good fiction, although I do have, you know

2:04:09 Cheap thrills. Yeah, I yeah, I do. I do. I really love beautiful Beautiful fiction. I dabble I've always dabbled in the kind of science fiction, magical realism Stuff as well. I believe, for me at least, escape.

2:04:25 From The Cranked up. Quick twitch, always on alert, operational stuff that business people go with. Yeah, exactly. To get my brain my I've monkey brain. Okay, and to get my monkey brain to relax.

2:04:40 Escaping into a fiction novel for me is just a fantastic Release. So with all that said, what stuff do I like? And then I've gifted recently I gifted The oceans and the stars. Do you know Mark Halpron? Oh no.

2:04:55 Okay. He's a guy who's a little older than I am and writes characters that are just about in my Like a beautiful, luscious prose writer. Really smart wrote.

2:05:07 Soldier of the Great War and A Winter's Tale and Freddy and Frederica. I don't know if these if you've heard of any of these books. There's a little bit of magic in'em. Magic is a prime character in all these books. It's this luscious prose and epic stories of War and romance and exploration and relationships. And this latest one is I highly recommend It's a kind of on the edge of retirement.

2:05:33 Just under Admiral or like a a low level Admiral in the US Navy. who almost becomes head of the D O D but doesn't get it'cause he speaks his mind and then he gets commissioned As a rebuke on this new weird ship. And I'll I'll just say that and that's the setup for him taking this really K more fast attack destroyer into into the Middle East. And he's kind of a war guy. He's he's a vet.

2:05:58 And he's a pretty engaged political kind of I'd call him an offensive realist in the John Meersheimer mold. kinda hawkish would be perceived as hawkish, you know, believes in strong defense. The protagonist. The author. I got it. Mark Alperton, he's this is his mindset.

2:06:15 So that manifests in Basically romantic stories of Heroic. You know, war efforts, which is you know I'm a boy. I like that stuff. So you would if I recommend Oceans and Stars is great. The one the only one of his that I probably reread is a Winters Tale, which was my first one I ever read by him. It's just a beautiful

2:06:35 Beautiful story of early twentieth century life. near New York City and upstate New York. You might actually like it. I might dang it. I read last the Mohicans just to Take a walk through that area in that time period. Authors I like. I like

2:06:50 Hiroki Murakami kinda magic. Neil Stevenson is Mike. Some people don't like his latest book Polost on. I don't know if he's the one who wrote Snow Crash. Oh yeah. Okay. So you know him. I had pizza in Seattle with a couple of other guys. And I was like, wait, you do Victorian era?

2:07:10 Halisthenics with Oh, and you make swords? Wait, what? There I mean lots of And he's got the beard. Oh amazing beard, yeah. I actually kinda like froze up when I met him. It doesn't happen to me very often, but he's kind of a hero. And he's in Seattle. He's in Yeah, he's right there. Yeah, he's right there. So I see him occasionally at our sushi place. I get scared. But his latest

2:07:32 Polostom. I highly recommend. Okay, I haven't read it yet. Some people are Giving me grief.

2:07:39 For it. You know, authors when they get Successful late in there. Well, it's long. A lot of his stuff is long, but it's not that long. It's not like cryptonomicon or something like that. Which I love. Which me too. Me too. But Authors as they get successful sometimes, you know, they have too much power over their editors and so they get a little self indulgent, you know?

2:07:59 Which For me with a beautiful prose writer, I'm like, take me along, fine, I will indulge your self indulgence and I and I don't mind it. But this one takes a hundred To a hundred and fifty pages to break into, but then it just goes. Then it rips. Then it rips. Yeah. So anyway, I highly right. And it's gonna be a trilogy. And so it's only the first one, so I'm like, you know, I can't wait. Anyway, I love you can tell I love to uh I love to read fiction. Yeah. And do you lean

2:08:25 These days If you're gifting, do you have you gifted those books that you mentioned? I have gift oceans and stars, but I'm such a Kindle person and so many of us are digital readers now. It's kinda hard to gift. Yeah, it is. It's more You know, group chat.

2:08:39 Yeah. Group chat. That's how most of the Book discovery happens for me now. Have you read any of Ted Chang's stuff? Uh Oh man. Who is it? Okay. So Ted C H I A N G

2:08:53 Okay. He has last I checked, he has two collections of short stories. There is one which I always script the title of. It's stories of your life and other stories, something like that. Okay.

2:09:10 And one of those short stories was the basis for the movie Arrival with Jeremy Renner. Amazing movie. So one of his short stories was the basis for that. And then I read that collection and pretty much everyone I read it was just like I don't understand how this guy does this. And if they happen to be writers are also just like Sad clown tear, you know, just like

2:09:33 How does someone even begin to create something like this? His second collection came out, Exhalation, and I didn't want to buy it because I didn't want to be disappointed. Like there's just no way, right? Like that first one was appetite for destruction. Like, yeah, you can't do that twice. And The second was just unbelievably good. And Not all of them will hit. Necessarily.

2:09:55 But the ones that hit. are just incredible and he has And they're like one night read short story a collection of one night I would say a lot of them are one night reads. Some of them end up being a little bit longer, but he along with other writers too, Kenneth Liu, I think is L I U, he has the paper menagerie, which was actually gifted to me by Matt Mullenwick Blends. Or alternates in a sense between sci fi and fantasy. In this.

2:10:21 Really compelling way. Cool. So you get these like little ginger snacks in between your Pieces of sushi. That sounds like my own resets. So highly, highly recommend. And I think for the longest time he wasn't maybe he still isn't a full time writer. That's the part that really got me where it's like, okay, he writes technical manuals for A, B, or C and then in in his spare time he wins Hugo and Nebula Wars. It's just like oh come on. Yeah. There's hope there's hope for I always kinda wish I became a writer. I don't like to write, but I'm not that good. I've never dedicated time to it, but

2:10:56 In that vein. This guy Amorts, do you know? I've only read He was a banker. I know. Finance. That's well, that's another one. Forty No, I know. I read the only thing I've read of his is Lincoln Highway, which I mean, it is such a page turner. It's so beautifully architected, and I read that. And I threw someone named uh Hugh Howie shook hands with Amor very briefly at a restaurant. We happened to bump into each other.

2:11:24 And I found out about the finance background, I was like, You gotta be kidding me. I know. You gotta be kidding me. I learned that he d was on somebody's pod. He gave a great pod when Lincoln Highway came out. Yeah. To somebody who cracks open artists, it might have been like Brian, um

2:11:37 M compliment. Yeah. Very well could have been compliment. Who, by the way, for people who don't know, a quick bit of trivia So Brian Kalman, co-creator of billions and co-writer of Rounders and all these movies and TV shows and so on. Also Discover Tracy Chapman. As a musician.

2:11:57 Back in his A and R days. Really? Yeah. Not wild. He's a talented guy. Yeah. So it wouldn't surprise me if Amor was on. He was yeah, he was on there and I and got him to crack up and then he was kinda surprised by Brian's questions, I think, and didn't know of Brian and all this stuff came out. Yeah you know. Amazing. All right.

2:12:18 This is the Billboard question. If you could put anything on a billboard. Message. Quote. Minder.

2:12:27 Anything at all. Obviously metaphorically, just to get something in front of a lot of people. You asked us, so I did think about it a little bit. And My initial response that I latched on to came from that movie Bowfinger. I don't know if you ever saw Bowfinger. It's a cult classic and a lot of you people out there haven't seen it, but I highly recommend it. It's Eddie Murphy tour de force.

2:12:48 And Steve Martin and Heather Graham. It's super quirky. Eddie Murphy plays two roles. And it Which he did for a while in in lots of movies. Anyway, he plays one of his roles he plays a paranoid Hollywood celebrity.

2:13:03 Who thinks and in fact is being followed by people who are making a movie about him with him starring it unbeknownst to him. That's the shut up. Steve Martin's directing.

2:13:14 And he gets super he's already a paranoid guy, but he gets super paranoid. He's like, People are following me. And he goes to a thing that I don't know what kind of culty LA religion it's representing. Mm-hmm. But it's called Mindhead. Uh and he goes in and has his first counseling with the high priest of Mindhead.

2:13:33 And the religion is based on three happy premises. I'm not gonna remember'em all, but but happy premise number one was something like There is no giant foot in the sky about to step on me. Okay, this is like a mantra you have to repeat. The third one is my favorite and that was the what I was gonna put on the billboard and that is Even though I feel like I might ignite

2:13:54 I probably won't. Okay. That goes on my billboard. That or my favorite Burning Man bar ever was uh had that giant neon saw and and on top of this kind of cozy geodesic dome playing groovy.

2:14:08 Music decorated as an aquarium. Anybody out there it's like it was at Burning Man a while ago and it hasn't come back. It was our favorite spot. And the sign said. Don't Panic.

2:14:20 Well say more. That's it. Don't panic. So that's on the billboard. Don't panic. Don't panic. I think a lot of My job as a leader, n explicitly or naturally, or otherwise, is to naturally bring people off of their high High beta, high swings, high mood swings. People have a tendency to to towards fear and panic.

2:14:39 And Almost always it's gonna be just fine. And when it's not, it doesn't matter anyway. Okay. Yeah. All right. And it can cause a lot of a a happier life and a calmer community. And a better, healthier community and family if everybody just takes a little breath before

2:14:59 Getting scared. You know or getting or sending a a text or whatever. Even though I feel like I might ignite, I probably won't. Is that basically related to the don't panic? I think so. I think that led me to the don't panic. I think so. And I'm not saying I actually I don't move through the world feeling as if I might ignite. I really don't. But I think a lot of people especially in the the modern Newsfeed. iPhone TikTok.

2:15:24 Twitter world do feel that way. Yeah. And so it's even more important. It's it's why meditation is on the rise. It's why We're looking for escapes. Mm-hmm. We're looking to give our brains

2:15:36 Embodies just a break from the constant barrage. It's causing mental health problems we all are familiar with. You know, and I think that's part of it. It's just too easy to get mad or scared or outraged or whatever. Go? Take a rafting trip for a week. Yeah.

2:15:50 That's disconnected. That's gonna be on the rise. Those are growth businesses, right? People sheltering From Hail storm of doom. Exactly. It's so unhealthy. You know? Have you taken any sabbaticals since Italy? Oh yeah. I mean I I've had multiple retirements and

2:16:08 Now are those failed retirements or did those have an end point where like I'm gonna take a year and then I'm gonna dust off my own. The early one was a failed one. Although I suspect it. I was really young. Right. The others no, it's just been sabbaticals. How long are they typically? You know, the Italy one was the longest one, but I've kinda built

2:16:28 Shelter. Into our family's routine now. Mm. So it's just a part of the normal cycle of the seasons? Mm-hmm. You know?

2:16:37 And a really key component of that. Not always achievable. Especially now. Starlink and Probably Starling. Starling at my surf camp and string at my airstream. Like it's harder and harder to disconnect, but disconnection is really

2:16:50 A key part of it. I think. I think disconnection, the behavior you observe when people are disconnected, uh Like with my family when we do we rafter the Grand Canyon. This year with a big group of friends and family.

2:17:01 And when you watch the younger people, it's very Unsettling. For the first Only like three or four hours. Mm-hmm.

2:17:09 And then when they realize it's over, it's total mean reversion to n human behavior. Playing games, doing crafts, taking a hike, you know. Painting a picture. You know, it's totally beautiful what happens, and everybody is happy. Well you can't not be happy making a friendship bracelet or playing Taco Cat, what are we I don't wanna I don't wanna give that away. I don't wanna give your game away. But you can't not be happy when you're doing that and not looking at your phone. Yeah.

2:17:40 Highly encouraged. Rich. Tim. So nice to see you, man. It's great to see you. We've covered a lot of ground. That was fun. Wow. Where If people want to learn more things about Rich, should they Be visitor twenty two to your blog? No, I don't think so. I think the the blog is totally vestible. It's an appendix that needs to be removed. Hopper and dropper. Yeah. No

2:18:02 Yeah, no, man, I don't you know the writing thing, I I've had a lot of offers to do that with I've just never felt like I enjoyed reading any of those Yeah. Ego books, you know. I just don't find them very interesting. And I don't want to be one of those

2:18:17 Kind of jerk offs, you know? Maybe do a writer's retreat or an M FA, compressed M F A, and take a stab at fiction? To fan. Even if you never publish anything, it's a good muscle to Train for a bit, just to play with it.

2:18:30 I'm doing more creative things deliberately now and it feels good. Yeah. Like I took a Procreate painting on my iPad during COVID and it's so I'm so I feel so good.

2:18:41 And I like catch myself going back and looking at my works and I sho like at a be at a party And then I'll I'll show people what I painted. Yeah. Yeah. But it makes me feel good. I did exactly the same thing during Covet. Appropriate.

2:18:54 And you go through these tutorials, there's something very soothing about. Australian gal Yeah. Oh who I think works appropriate. Who gives the tutorials so awesome. Yeah, so many good ones. Is there anything you would like to say? Any closing comments, formal public complaints you'd like to lodge. No, no, I guess I should just I should thank you. You perform a good service. You provide a good service for a lot of people with this podcast and with your books. You know, and certain people need it more than others. And I don't think I really don't think people are looking for shortcuts. That may have been where you started a little bit. Yeah.

2:19:31 I really just think People are just looking to lead Better, happier, slightly more efficient. Yeah lives. Improving lives. They want to improve themselves. And you really help people do that and they the diversity of The guests that you bring on this pod is really inspiring. So yeah, it's great. Thank you. Thanks, man. It's great to be here. Yeah.

2:19:53 Awesome to have you. Everybody listening, we're gonna include everything we talked about in the show notes, Tim.blog slash podcast. You search Barton, that's gonna be the only Barton, so you'll find this episode. And until next time, be just a bit kinder. than is necessary to others, but also to yourself. And as always, thanks. Tuning. Hey guys, this is Tim again, just one more thing before you take off, and that is Five Bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little fun before the weekend? Between one and a half and two million people subscribe to my free newsletter, my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel.

2:20:34 It is basically a half page that I send out every Friday to share the coolest things I've found or discovered or have started exploring over that week. It's kind of like my diary of cool things. It often includes articles I'm reading, books I'm reading. albums perhaps gadgets gizmas all sorts of tech tricks and so on that get sent to me by my friends including a lot of podcast guests and these strange esoteric things end up in my field and then I test them and then I share them with you. So if that sounds fun again it's very short a little tiny bite of goodness before you head off for the weekend, something to think about. If you'd like to try it out, just go to Tim.blog slash Friday. Type that into your browser, Tim.blog slash. Friday, drop in your email and you'll get the very next one. Thanks for listening.

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