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

Episode Date: April 16, 2025

Rich Barton is the co-founder and co-executive chairman of Zillow, a company transforming how people buy, sell, rent, and finance homes. Before Zillow, Rich founded Expedia within Microsoft in 1994 and successfully spun the company off as a public company in 1999. He served as president, CEO, and board director of Expedia and later co-founded and served as non-executive chairman of Glassdoor.Sponsors:Ramp easy-to-use corporate cards, bill payments, accounting, and more: https://ramp.com/tim (Get $250 when you join Ramp)Cresset prestigious family office for CEOs, founders, and entrepreneurs: https://cressetcapital.com/tim (book a call today)Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business: https://shopify.com/tim (one-dollar-per-month trial period)*For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast.For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsorsSign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissYouTube: youtube.com/timferrissFacebook: facebook.com/timferriss LinkedIn: linkedin.com/in/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hello boys and girls ladies and germs. This is Tim Ferriss. Welcome to another episode of the Tim Ferriss 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 Sokka 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, Rich founded Expedia within Microsoft in 1994 and successfully spun the company off as a public company in 1999. 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 going to enjoy it. 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 Barton. My first book, The Four Hour Workweek, which made everything else possible, is built around the acronym and framework DEAL. D-E-A-L, define, eliminate, automate, and liberate. Now, of course, after you define all the things you want, your metrics, 80-20, define, eliminate, automate, and liberate. Now, of course, after you define all the things you want, your metrics, 80-20, blah, blah, blah, then you wanna get rid of as much as possible, eliminate. But sometimes there are things that are a huge hassle,

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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. Can I answer your personal question? Now or the sooner the better. What if I did the opposite? I'm a cybernetic organism living this year over metal endoskeleton.

Me, Tim Ferriss, Joe. issue of a metal handle skeleton. I know ADQ a little bit, he's a friend, and there was a point at which, you know, I like to observe magic product things, and of course Apple has tons, but my typical morning news setup is I'm kind of doing my email and sifting through things while I drink my coffee and I've got my iPad set up next to it rolling CNBC quietly on mute. And at one point a couple

years ago, I moused off the left edge of the screen and it seamlessly went onto the end. I also had my mouse is on the iPad and 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 texted him immediately, I'm like, oh, Eddie. Why do you have CNBC 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. Okay. Just don't wallow in the bullshit. 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. And I get the news. I'm interested in business and companies and strategy and trends and it is pretty funny channel. It kind of gets on repeat.

You don't need to watch it very long, but they get good interviews too. I usually don't have the volume on. I have the closed caption scrolling and then if something catches my eye, I don't know how to do it. So let's take a closer look then at the other screen. Yeah. You have your coffee. Yeah. What time is this?

Yeah, I'm a pretty early riser. 630 I get up usually and long before Sarah, my wife. 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 that was obviously very different and really fun. I can talk about that. But now I have two hours of just catch up on the stuff in my newsfeed, which is my inbox, my email inbox. I'm kind of old school that way. And as I go through that, I'm catching up 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, but lots of- Cat testicles. I am not one of those guys. I am not one of the longevity supplement people, but I'll tell you what's in it. It's about three or four ounces of oat milk, ice, an apple, used to be a banana, I've switched to kind of two thirds of an apple, pistachios, macadamias, a handful of blueberries,

my favorite electrolyte, I'm getting ready for my workout. It's not very big. My favorite electrolyte is Prokary Sweat. Yeah, the blue can, man. I had a lot of that when I lived there as an exchange student. My nutritionist says, that's the one. And I'm like, okay, I'd been taking another one, using another one. She's like, no, this is the one.

Not much, a prune. Prune. Prune, because- Keeps things moving. Keeps things moving, and that's very important. You know, young people out there don't really realize how important that is yet. 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 quirks, I guess. Hyperice, 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. You must have run into that. I think it's heat and vibration.

Yes. Yeah. So I actually, for my whole kind of 45 minutes of that routine at the kitchen table, 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. That loosens everything up too. And you mentioned before your workout.

So this is all pre-workout? Yeah. I need to get things going and feel settled, a little bit settled, and brain on before I work out. Coffee helps too. Coffee helps all that. Yep, and I don't drink a lot of coffee. Today I had a little too much 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 change into my workout stuff. Rinse your face with some holy water. And pretty much every day I do a workout.

I can't really get my mind right without that. All right. So we're going to talk about the workout for people who are audio only. This guy looks like a, I don't know how you, Marvel character meets Abercrombie and Fitch model, not to mention scion of business. It's unfair. I don't know how I got the shorts drawn this genetic and habit lottery, but we're going

to talk about the training because I have this working pet theory that longevity may be inversely correlated with the number of things that you do for longevity. 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. So when you start throwing the kitchen sink plus plus 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 the supplement thing and the whole day scheduled out lifestyle things to improve health span, yeah, most of that's probably not very useful. Yeah, there's some basics. And maybe the most important basic is when I was younger, my kids were in the house because I got up early, I was the get the kids to school parent. Yeah. While Sarah became more beautiful, she stays up late. And I love to cook. 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 bar, stools and the cook top is on the other side. And whenever the kids wander downstairs bleary eyed, I was their short order breakfast chef and anything they wanted I would make, which was so fun. It was like the breakfast buffet at the Four Seasons or something. Whatever they wanted.

I could whip it up really, really fast because you get that skill when you're a short order chef. My younger boy had some kind of ADHD stuff and started taking the meds. I can't remember how old he was, 10, 12. And those meds make kids, it's an appetite suppressant. Oh, for sure. Okay, so maybe you know. And I was a typical parent,

our primal urge is to feed our children, that's it. Like feeding 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 12 egg frittata and like put potatoes in it and sausage in it and he'd down the thing. And I'm like,

okay, he's good for the day. The anaconda diet, just one huge meal. And it works. You should accomplish the anaconda diet. Just one huge meal. 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 ran is just really quality. I cherished it. I took a picture most days Mmm, okay Totally candid there no posing I would sneak a picture every day and now 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 a time series of these kids growing up. It's a virtual possession, but it's my most prized possession. All right, we're gonna double click on a bunch of things we passed over. Let's hop for 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? Brad Chase? Yeah. What impact did he have on your life? He was a great guy. He was my first real boss out of college.

It's not quite right, but it's close to right. Brad was a group product manager at Microsoft. Microsoft was my, I'll call it my first job out of college. It had, this is 1991, Microsoft had only about 3,000 people at the time. Just for reference, because I have no idea, how many employees do you think they have now? It's gonna be a multiple of that, of course. 300, 400,000. Yeah, orders of magnitude.

Multiple orders of magnitude, 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 5, which maybe I would say we'll have to go two standard deviations at in your audience distribution curve to find anybody who really knows what MS-DOS 5 was, but it was a really big operating system

for Microsoft at the time and we made an upgrade and the feature was we broke the 640K barrier, which you're not gonna engage on the geeky stuff. It was a really big product and my job was to create the packaging, manage the 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 and to push the product out into Egghead. 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, you know, big risks, big bets. 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.

Is this 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 details help paint a picture. People can conjure a visual in their head. All right. It's become a huge series.

There's a series for dummies, blank for dummies. And the book that the dummies series was founded on was DOS for dummies, believe it or not. It was like the best selling book about software of all time. And I was like, I'm a young product manager, I want to sell more MS-DOS 5 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 Bookstore. The bookstore experience was huge back then.

And DOS 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 with DOS for Dummies and have that be the manual for the upgrade. Bundle it together, the book and the upgrade. Seems reasonable. And distribute it 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 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 feeling pretty like a big deal. Built a bunch of it at probably cost us eight to 10 bucks a unit. Yeah. Okay. Which is a lot for cogs, right? Cost a good 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 $12 book. And it was a $54 price tag or $49 price tag, which is what, you know, basically what the software cost

at Egghead. And it kind of looked a bit too much like a book. I'm embarrassed about what it looks like now. The shock value was too much. We ended up getting rid of all the inventory, but 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 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 going to, who knows? It was a 10, $20 million 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? Amazing. That is that Microsoft was and is an amazing organization because of that kind of culture. Wow. How have you, if you have sort of taken that forward into companies that you've built or just philosophically or operationally speaking,

how do you encourage that? Because there must be some constraints on things that you don't light the whole house on fire. Right? How do you think about enabling people to innovate? You don't want learned helplessness where they're afraid to do anything. At the same time, you don't want some rogue trader like taking a Paris turns or whatever. 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 X, Y, Z 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 intrapreneurs, let's call them, okay, the inside entrepreneurs, and protect them a little bit because sometimes they're different and mainline corporate culture sometimes rejects, often rejects the innovators and the ones who want to disrupt whatever, just 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, 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? All right, so let's come back to one thing you mentioned. You 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? I was, you know, I was one of these high performance. There's a confession coming. Yeah, I was just one of those kids, you know,

I went to Stanford and was an engineer. Management consulting? Yeah. Really? No. I know, but it was funny. There's a good story here. I mean, I don't know if it's a good story, but we'll tell it. Yeah, man, I was like a success kid, 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. And 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, right out of college.

I knew pretty damn quickly it wasn't for me. Was it by like BCG or who was? It was a spin-off of BCG. Okay. Called Alliance Consulting Group. Great group of people, super smart. It was going into a recession though in 1989 and so a lot of people ended up losing their jobs.

However, the interesting thing was one of my besties at Stanford, Nina Roberts, who was an engineer with me, we were both interviewing for all the same jobs. And she didn't get the big job, but she got this little tech company in Seattle, Microsoft, which of course I knew, the companies that I really loved were Microsoft, Apple. All I needed to do was buy Microsoft and Apple stock

back in 89, that would have been, 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 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 got to come out here, you got to come out here. And so it took about a year to finally get the flight out and the job offer. How did you know it wasn't for you? What about it wasn't for you? Because there are some people who thrive in those environments, right? Yes, yes, yes, yes, yes. 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. It kind of makes you feel important when you dress up. I was presenting things to CEOs and stuff, and it did feel important. I got a really good business school education in competitive strategy, you know, the Michael Porter stuff.

I basically got an MBA in this one year. What I discovered about myself, and I discovered it there, I probably knew it before, but I hadn't really focused on it, was I believe the world is somewhat divided. It isn't totally binary, but it's a continuum, but it's maybe continuum, but it's maybe a barbell. Clients and servers, which is kind of a geeky software architecture reference, but people get it. There are all of these industries that are set up to be service provision

industries, lawyers, doctors, consultants, academics. And the benefit of these industries is you get to indulge your curiosity and see lots of different, deal with lots of different clients and lots of different problems. But oftentimes with consulting, you're not seeing things through to the finished product. And it was apparent to me really quickly that I derived 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 I was a consultant. So it became clear to me that I was a client. I wanted to build things.

I derived my jollies that way. And so I started looking and it was good to discover at a pretty young age. And then I got to Microsoft and it was like, 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 still gets a box of chocolates. We're still close. She's great. All right. So let's talk about then Microsoft and 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,

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, is a doctor and she was applying to, she was in medical school at Northwestern and was applying to her residencies. She's an OB-GYN. And there's only one OB-GYN residency in Seattle where I lived with only six or seven 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 in Seattle, so I'd better get ready to move to New York City or this probably would have been New York City where she matched. This was during the Windows 95 launch. I left the Windows 95 team and I went to the consumer division at Microsoft,

which was kind of small. Now just, this is going to maybe sound like a side quest, but when you say you moved, did you just put in a request? 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. But it's still not easy, of course. Brad, who was my boss at the time, couldn't believe we're launching Windows 95.

This is going to be the biggest launch of all time in the software industry. Maybe one of the biggest product launches of all time. I don't know if you remember that. I do. 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 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 was going to have to leave Microsoft and I wanted to start a company. And it wasn't going to be an operating system. Yeah. OK? Like that just wasn't going to happen for reasons that we don't need to get into. But the government made clear to Microsoft at one point.

So I figured it was going to be a consumer software company. And I wanted to go learn that. And the folks over there were fantastic. Microsoft was fantastic. And I took on a portfolio of CD-ROMs. Some of you 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. It's true. It's true. And some artists, some musicians still hand out CDs. It's the artifact that your doctor gives you. Oh, it was what came in the red envelopes at Netflix. Anyway, so these things were like Wikipedia before Wikipedia was called Encarta. It was a multimedia CD-ROM and one of the products in my portfolio of like rando ideas

was an Encarta, so an encyclopedia of travel guides. This really good take a whole bookshelf a whole shelf of travel guides cram it down on the one CD rom pictures audio wow what could be better for travel planning and that was one of them. I remember going into my first product review with bill gates and others which was a kind of six months, every year kind of thing that the product people did. And I was used to business plans with billions of dollars from the operating system group. And I was responsible for this thing. And I'm like, Bill, this is tiny. The whole travel book industry in the US is maybe $100 million. And that's the whole thing.

And so really, A, there's not an opportunity. And B, you can't travel with the CD-ROM. There were no like, the laptop at that point was this compact suitcase that weighed 20 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 kind of fun, it's not gonna work.

That said, I demoed EasySaber on Prodigy. Prodigy was an online service. Oh, yeah. OK, and I was a geeky online guy. Right. And EasySaber was a tool for travel agents to use at home on Prodigy to access the airline reservation systems.

OK, 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 of 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, my dream. The pitch further went, and fund me on the outside, because I'm gonna have to move to New York, because my pitch, my dream. on Windows NT, which is a different conversation. So he loved it, he green lit 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. High degree of confidence. Yeah, 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 he had that kind of power, but 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. 1999. I moved out right before the Thelma and Lewis car went off the cliff.

I mean, I moved out to the Bay Area in 2000. It was crazy. What time pegable 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 good muppets, but Expedia was a really good business. I was working for Balmer at the time, and I asked Steve for $100 million 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. And Steve like laughed at me like, no, we don't do that. I said, well, dogshit.com is going public right now. Had a billion dollar valuation, wasn't quite that. It was like 500 million, which seemed big at the time. Really dumb, stupid stuff in my closet.com was going public.

Put it on the web. Anyway, and I was like, the public markets would give us $100 million. And it'll cost basically nothing. And so let's give this a try. Let me spin this thing out. It's a good HR experiment, human resources experiment too. Now just explain for folks,

why does spinning something out make sense? What are the advantages of doing that? To them and to you? Okay, I mean, the financial answer to that is unlocking value that is stuck in a company. And this happens a lot. That's kind of the most uninteresting one. Unlocking value meaning.

It's not getting valued by the shareholders as being part of Microsoft. Right, but 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, okay? So 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 the GE, the Jack Welch GE days and Honeywell and there were all these big conglomerates and then the pendulum swung the other way. Microsoft could have 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 Microsoft Office succeeded, they could make a lot of money off their stock options. And so that's basically a compensation accountability disconnect. Okay? And so some of the best people at Microsoft, there was this field of dreams, wild opportunity outside of Microsoft, even though it was the place everybody wanted to work at the time, 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. Got it, 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 Maffei, who was the And so he's like, yeah, we'll take a flyer on it. And that was great.

And Greg Maffei, who was the CFO at the time, he became my chairman and he was really supportive. You know, he and I still work together. He's been a great, great mentor to me. We took 150 people out of Microsoft. We gave them the choice if they wanted to stay or come, all but I think two people. We had 150 of us, all but two people decided to come,

take the adventure, give it a rip. I was 32 years old, 31, 32 years old. Now were you pitching those people yourself? Yeah. What was the pitch? Because it's going to be different than the pitch to Balmer, right? 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 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 S1. For those who know it's an IPO document with with our Expedia draft of the S1 lying on a dinner table at Wild Ginger in Seattle with a skeptical spouse. The S1 is highlighted and like there's annotation and I'm having to answer like, you know, those were my toughest investors

actually. It worked out really well, maybe too well because Expedia was a real business. We actually were profitable and growing like crazy. Obviously, digital travel agent made a lot of sense. When Thelma and Louise went off the cloud, as you say, we were already public. We'd gone to the moon, the stock price had gone to the moon, we crashed back down, but we had a real business. Very shortly, popped back up on the climb and just climbed from there and were very successful. Microsoft, however, crashed with Thelma and Louise and it took 17 years for Microsoft

to re-achieve the same stock price it had in November of 99 when we spun Expedia out. So the HR experiment kind of failed. How long did it take Expedia to recover or to get back on the climb? I mean, to re-achieve the all time high, probably a couple of years. Yeah. But a couple versus 17. Yeah. But the valuations were a bit nutty, right? So 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. 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 2000s 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.

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at Shopify.com slash Tim, all lowercase. Go to shopify.com slash Tim to start selling today with Shopify. One more time, shopify.com slash Tim. 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, bomber, gates, spouses. That is a skill set. Persuasion.

Yeah, how did you develop that? It just must have been 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 technology. I was a geek. What type of engineer? I was initially the story that kind of answers the question. I was an industrial engineer theoretically, but I wanted to go study in Italy my junior year. Now industrial engineer would be like, you end up going to a smart design or one of those

types of companies or how are you thinking your path would unfold? It's not a degree anymore at Stanford. It's called management science and engineering and then there's kind of a symbolic systems thing. The industrial engineering degree, which kind of sunset it was really a kind of manufacturing efficiency. I got it. Okay. I got it. that it was really a kind of manufacturing efficiency. Optimization, simulation, lots of computer work going in.

It's the design of making things more efficient. I did it just because it was 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 because the mechanical and electrical folks didn't respect us. Probably deservedly because we were 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.

Already, already, already as a kid I had all that. I probably was a good pitch person already, but had a lot of support 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, and Stanford was awesome.

I came back and I was like, well, you can't get an accredited degree now. I'm like, I don't care. And 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 I designed one. So my degree is called General Engineering Colon Industrial Economics. Anyway, unlike a lot of kids today, I worked real summer jobs, you know?

My kids generally did, actually. My kids have worked real summer jobs. So we were talking like busboy, what do you think? Yeah, I mean, my daughter, I'm just thinking of what their jobs are. I know my daughter spent, you're gonna know this place, you know, after Gurney's was redone, it became like this club scene.

This is out at Montauk. Once it got fancied up. It got super fancied up. Took away the day passes for the locals, you bastards. Anyway, yep. Yep. So she was, it was after her sophomore year in college, I think, or freshman, 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 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, who's the person that stands at the counter when the hostess at the club part of Gurney's. Oh God. Okay, where it was like $2,000 tables. Yeah, yeah, that's quite an education.

It's an amazing human nature job. Oh my God. She had a crazy successful, interesting learning experience. 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. And then after one year doing that, like, 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 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 $15,000 or $20,000 summer painting and that was a boatload of money. And so I had run my own businesses. Got it. All right. And knew I liked it. And why did you go to Italy at all?

Why did I want to go when I was in school? I have no Italian heritage, as you can probably tell. 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. And 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 as important, you know?

And I kind of fell in love with it and kept going back. So I went to study and then after I sold Expedia to Barry Diller, we Expedia to Barry Diller We were public and Barry Diller bought it and we had three little kids and I was leaving after very by 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 Expedia In fact Nina who I was talking about before she was living there married to a European guy

In fact, Nina, who I was talking about before she was living there, married to a European guy. And I'd gone to Stanford there when I was a junior and I'd kept in touch with the woman who ran the Stanford program, Linda. And so we kind of moved to Florence and went back to school and learned how to paint and started road biking. Anyway, so I just, I love the whole Italy vibe. Let's take a closer look at the Barry Diller transaction. How did that come to be and what were the most important aspects of that deal?

Could be deal structure, could be timing, could be anything. But how does that even happen? Yeah. So Expedia had been public for maybe four years and had become very successful and pretty big, pretty highly valued in the market. And I think it came about, I mean Barry was kind of interesting, he was building a interactive conglomerate

called IAC, USA Networks. I think he owns most of the popular dating apps, things like that, I mean IAC buys a lot of stuff. And then spun it out as Match.com. And yeah, he was that. I mean, I see he buys a lot of stuff. And then spun it out as match.com. And yeah, he was post his media career, he got into interactive media and he started buying stuff. And the guy, his kind of key corporate development strategist

and all around great freaking guy who worked for him was a young guy named Dara Kazushahi. Ah, okay. Folks might recognize that name. I may be miscrediting or giving you too much credit, Dara Kazushahi. Okay. Folks might recognize that name. I may be miscrediting or giving you too much credit, Dara, but probably not. I think this was Dara's idea was consolidate the players in the online travel space, that it was already big, but it was going to be much bigger. Microsoft was the majority owner, but didn't have anybody on the board.

Even there, 65% of the company didn't have anybody on the board. They knew me and they trusted Greg Maffei, who had left SCFO and was running company. Unbelievable level of trust. It just didn't matter to Microsoft. Yeah, I guess. It didn't matter.

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 the easy thing to do was to take a big offer from Barry Diller. And so they did. It was a bit of a two-step deal that IAC and Dara and Barry bought Microsoft 65%.

And then maybe, so we were public but captive to IAC and Barry Diller was my chairman for a while and then maybe eight months later bid for the rest of it. And consolidated it down. I think they kind of pushed us to buy the number two player, which was hotels.com. And so we mashed those things together and I moved on at that point. So when in that journey the Expedia journey Did you feel the highest high like for instance? I would imagine when you are 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 15, 20 grand. Yeah. Like, my God, you must've felt rich. Yeah. We went to the highlight. You know, the highlight is, took the crew to the highlight.

Yeah. So with the Expedia journey, was it the tail end with the Barry Dillard transaction? No, no, because that'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.

No, I mean, that was great and it made sense and it created value. No, the highest highs were probably around the spin out and the IPO. 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 1999. It's really pitching to the buy side. So it's pitching to the mutual funds, to the investors.

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 going public and a lot more companies went public then. There was a rite of passage back then for companies going public and a lot more companies went public then. It was 15 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. Exhausting and exhilarating and repetitive 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 30 times over, which means we had a lot more demand. We knew the offering was going to 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 going to work. The IPO was going to work. And I called the Red Show off a day early.

I flew back to Seattle 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 at 3 a.m. 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 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. And then we went to the hospital and while the IPO was happening, my son was being born.

Yeah, my oldest was being born. And so that was actually the high point right there. Wow. All right. Now we're tracking the path. So now you're painting a vase of fruit in Florence, living the life of a- Naked, it was naked woman. It was like, it was like drawing charcoal. Yeah. All right. Charcoal, charcoal drawing of naked lady changing poses every 10 minutes.

What could be a better way to learn art? What a lovely way to learn art. And living the life of a fine gentleman, pasta and wine and culture and road biking, little cap maybe. Little cap, of course, no helmet, taking Italian classes in the morning. Yeah, espresso here and there. Sounds like a great life. It was fun. How the hell does Zillow happen?

Yeah. Do you start getting fidgety? I mean what what happens there? Yeah, I was still pretty young. So probably So three I was like 35 36 and I was hoping art Music thought I might write books whatever, you know find the next chapter Mm-hmm, because I really didn't need, I had enough to take care of myself for the rest of my life, but something I discovered, I was still on a few boards, including the IAC board, which had bought Expedia and Netflix, where I'd been on the board since like 2000.

And still I'm still on that board and a couple of 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. 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. Did it in Florence for a little over a year. We spent a few months skiing with the family, which was really fun in the mountains. And you came to the US. Came back to Seattle. I am going on a hunting expedition.

Did you already have an inkling of what you were gonna do? A little bit. I didn't know if I really had another startup in me because I knew how much work it was and I adjusted my life to prioritize some things I hadn't prioritized when I was younger like living well and family and body and mind. I was very curious in all kinds of different things. So the venture capital opportunity was available to me to go be a GP at a venture capital firm

and I was kind of headed in that direction. 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, probably for good reason awesome guy really smart Follow up on that As a fun story, but but Lloyd so Lloyd 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 we did and we went through a bunch of ideas for a while. And so we did. We did. And we went through a bunch of ideas. He went off on one that was kind of Dropbox before Dropbox. It was obvious that the cloud storage thing was going to be huge. And I said, go figure that out. See what it costs. And so he disappeared for a couple weeks. So we were sharing an office and came back and said, yeah, 100% this is going to work, but there's going to be no profit. There's no profit. Like, this is going to be, Microsoft and Google are going to give this away. And where were you guys brainstorming?

We were brainstorming in his dad's, his dad was a stockbroker where he had an extra couple rooms in his office and he just gave them to us. New York City? No, no, this is Seattle. Oh, Seattle. Seattle, yeah, yeah. So we're in Seattle,

because we didn't sell our house in Seattle. When we moved to Italy, we moved back to our house. But we were looking for a new house. We were going to 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, matchmaking service, all the classified categories basically,

and all the kind of agent categories were 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 basically to create a digital real estate marketplace. 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 2003 and I can't get the price of a home online. Like, 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 were like, well, wants to be power to the people here too, right? And we couldn't believe that it hadn't changed. And so that was the dawn of Zillow. So he convinced me not to move.

And I said, well, I'll be CEO, but I'm not going to work that hard. He's like, don't worry, I'll do it. Just be CEO. I need you to be CEO because you have to raise money and stuff. All this trick in the book. So maybe I am a four-hour worker, a cat kind of guy. I said, look, I don't want to do it full-time.

You can use my name. Of course, he was like, yeah, sure, whatever. You can do whatever you want, Rich, knowing I'd be sucked in. Let the line out. He totally managed to make me feel it back. Yeah, I think I'm in charge now. Lloyd was in charge. So when you say you're brainstorming, there's an entire universe of possibilities. What constraints or criteria are you applying to that brainstorming? What are you looking for? I think most great ideas, 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. 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.

We knew 100% that there would be a leading digital real estate marketplace in the US. At some point. At some point. Inevitability. Inevitability. Business model, who knows? Who cares? It's a giant.

It's a big pond. And so my business criteria for doing stuff is, is it a big pond and are there good fishermen? Right. Because the travel CD-ROM wasn't big enough, right? You said 100 million. That's the entire market. Plus, you're not going to carry a briefcase that you're doing weight training with inadvertently to read the thing. Right. that you're doing weight training with inadvertently. Problems.

To read the thing. Right. A lot of entrepreneurs make this mistake of identifying a really big problem, but it is just a small opportunity. And then there are ones where, like I know Bill Gurley was on the pod a couple of years ago talking about the Uber thing.

What did the insight, you were involved there a little bit. I was one of the first three advisors when it was called UberCab LLC, yeah, way back in the day. Yeah. And for people who didn't pick up, Dara. Yeah, oh, sorry, Dara is the CEO. Current CEO of Uber. He was the CEO of Expedia after, you know, two after I left as well. Anyway, a lot of people make the mistake is what I was going to say, of identifying a real problem, but it's just too small.

Uber, to some people, a lot of people looked too small, because it was a black car tam, this total addressable market. But the insight that you, and Curly, and Travis, and I guess J Cal, and others had was that actually, no, it was going to take not just the black car market, but taxi, transportation, and then ultimately more. It can expand the total addressable market. That's right. Car ownership. Just transportation. And of course, obviously it's beautifully

played out that way. It took a little while to see, but it's amazing. Anyway, so big pond, good fishermen 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. We didn't know how we were going to play. And we started poking at ideas for attracting audience with software. And we made a couple of big mistakes before we landed on the solution. What were some of the big mistakes and how costly, how risky were they? Pretty small venture numbers at that point and Lloyd and I were funding it ourselves.

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- Side note also what Garrett Camp did with Uber early on. He did too, he wrote, I didn't realize that. Yeah, there was self-funding for a while. Wasn't expensive, it wasn't overly expensive, but. It's a good way to go as a second-time founder or a non-first-time founder

if you actually have some resources. Because you end up with more of the company down the road. I love Gurley. We're really close. But by the time Gurley or the venture capitalists come in, if they're writing the first check, they're going to end up with a big chunk of the company, which is great, especially if you get somebody like Bill. But we were able to do it ourselves. We were enamored of 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 AdWords, the digital auction-based marketplace.

You say it came from another company. 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 that startup incubator factory gross? Oh bill gross. Yeah. Yeah, it was I may be getting this wrong Am I making some idea lab? He did idea lab there was a lot of companies kind of sort of spun out of that but one of them was a

Search engine whose name I'm forgetting. We can look it up later maybe. Put it in the show notes, yeah. But the whole basis of the search engine was AdWords. AdWords. Wow. So did Google acquire that or are they just being a better mousetrap? Think the latter, but I'm not an expert. All right.

Regardless, I don't want to speak out of turn. We'll put the story in the show notes. Okay, right. There's a good story there, I'm sure. Why I brought it up was we were enamored of auctions. Auctions have huge geek appeal for mathy idealists. And we were like, well, obviously the US housing market should be at 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 efficient mechanism for price discovery, which of course it is. And we were like, okay, so that's our business. We're going to auction homes. And what we learned trying to auction a home that our buddy Gordon got us kind of on consignment was that, well, two things. One, to have an auction work, you kind of need a real-time liquid market. Okay? Duh. Okay?

So you need all the bidders there at the same time. Okay. Well, the housing market doesn't work that way. It's just, you know, it's a long period of time. You want to show it to a lot of bidders. You know, that didn't work. The second thing, which is obvious, is, and to 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, you know,

from decades or hundreds of years of ingrained human behavior, it's a pretty heavy lift. It's got to be super duper simple, obvious, and 10 times better than the current way. And just we didn't check any of those boxes. But in pursuit of price discovery, we found the Zestimate, which was our killer feature. And the visual on the Zestimate that's in my head that kind of popped in our collective heads on the home auction web experiment

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. And the timing of that is pretty wild, right? And it's just like how things line up. I mean, how long had the aerial view 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. I was like, whoa. And then I also had in my head, homes are for American homeowners, oftentimes their largest asset 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 catnip.

In my gut, I knew that was, we did, the team knew it was candy. And I'm like, oh, it's an investment. And so let's plot the home value like a stock chart. And so the aerial view with the numbers, any home's value laid out like a stock chart. Those were the two things. And when we discovered that we were kind of off to the races. Okay. So at the time was it just rentable infrastructure, AWS, you got 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. lunch? Is that what happened? AWS didn't exist.

I know. You knew that. You baited me. No, dude, man. This was like server in a closet. Yeah, this was server in a closet. You forbade Christmas lights or something? You're preserving electricity and compute power and all this stuff. I don't remember that. I don't remember. All right, got it. But David, our CTO-

The things of lore. David Bitala, 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. Yeah, I believe. I remember our launch blog post with Garrett,

who worked for David, like doing the, what's the professor in? It's Doc, from Back to the Future. 3.2 gigawatts! Whatever. Because we launched, and millions of people showed up, professor in, uh, it's doc from back to the future. Because we launched and millions of people showed up because Walt Mossberg 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.

I mean, God and Walt loved it and Walt published and millions of people came on day one and And of course, the server in the closet tipped over for a while and it was painful. But Amy Botinsky, 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, house porn site Zillow launches and falls over because it's so popular, or something like that. And she's like, yeah, that's going to be good press. Anyway, I'm a big believer in 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, benchmarking TCVR, A-Round funders. And he was on the board, benchmarking TCV 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 to the brand.

And Gurley said, well, what if we didn't have any marketing budget? And that 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 going to feel emotional about one way or the other and they're going to talk about it, you're

onto something. What are some aspects of that toolkit or the other and they're going to talk about it, you're onto something. What are some aspects of that toolkit or the playbook? Yeah, I mean having data, having a stream of data that people are interested in at Glassdoor, which I did with Bob Homan who was at Expedia with me as well. Glassdoor is another example of that. When you have constantly changing data that people are interested in, you can almost think about feeding that data to hungry consumers in a Bloomberg-like way. And so the playbook that Amy kind of put together was building a PR data distribution infrastructure down to the local. Remind me who Amy is?

Amy was 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 time. And if you could wire that up to just feed, constantly feed the 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 money. And then just having this estimate be so provocative, like 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 lot of applications. I know you had a lot of fans. I think the Arizona attorney general was a fan. That's a good cut. Wow.

No, but this is of interest to me because there is opposition also. Oh yeah. Right. And a lot of my got me the number of, I don't think they were actual ulcers, but just the roller coaster ride that I was also on with Uber from a regulatory mobbed up local fill in the blank perspective. It was just nonstop battles. And that was just part of the deal.

Yep. Right. If you want to. And actually part of the playbook. Yeah. Honestly, it's the same provocation marketing. It's the exact same thing. It's exactly the same. Yeah. So what happened with you guys?

Yeah. I mean, we were provocative to some of the industry players who were big lobbyists. The Taxi Commission, Uber's case. In our case, a lot of the real estate professional associations. A lot of voters. They're not thrilled. They're not thrilled, or they think they're not thrilled. They don't realize until later that it could be helpful, but whatever.

Yes, they were initially provoked. No industry likes change. Most people don't like change. I'm one of the people that loves change, but a lot of people, most people don't. And so we were seen as a three-way scene. You may like change when you're the instigator of the change. Well, that's awesome. It leaves me more open to change coming from the outside too, though. I do believe. I do believe. And 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. They're not licensed. How can they make an appraisal? You know, whatever, whatever thing they're going to make up. We knew we were on really strong legal ground. And so we weren't so worried about that. But the strategy for combating that resistance was literally probably the same thing you

guys did at Uber, which was we knew the legislators, state legislators, not to mention federal legislators were big fans of the site and the service. Okay. And so all we had to do was make sure we just activated that latent love for the product itself and made it 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 wanna make this overly about Uber, but also turns out when people have something that is incredibly convenient and useful, they do not want to take it away. And if elected officials like the service or even ambivalent about the service, they do love getting reelected. And man, oh man, if there are a lot of your constituents using that app and you take it away, they're not going to be super happy about it.

Power to the people, baby. I mean, like you build 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 onto 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. Of course you can go too far. And in fact, it may be that you need to go too far to establish where the frontier is.

All right, well I can't not take the bait on that one. What does going too far look like? I was thinking specifically about Uber. Oh, all right. Yeah, but because some cities, municipalities, or Airbnb. You can push too hard. You can push too hard. And learn some lessons about how much leash you're going to be given

by the popular support. Because it does tip into a point where like with Airbnb, this is not a story, I know this guy's a little bit better, it's not a story I'm intimately familiar with nor was I an early investor or anything. But they did piss off some homeowners in certain cities, not just the hotel owners. So they found the line and I think they managed it really, really well because they lead from the heart.

I think other companies may have not obviously led from the heart and had difficulty. At Zillow, our job was a little easier. Also with those battles, I remember there were early on a number of locations that were incredibly important. 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 10 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, there's always something. But provocation marketing with a heart 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. Yeah. All right, there you go. You get to choose, you can go back to your alma mater, wherever it might be.

You're teaching a class. Yeah. What would other elements of the class be? Other resources, principles, anything at all? While I try to figure out a structure here on the flat to give a couple of other examples of stuff that I've been involved with. So I co-founded Glassdoor,

which many people out there may know. And our provocation data marketing feature was how much money do people make? Okay, not individuals, but the product manager at XYZ company or the developer or the customer service representative. And our model was, we knew that salaries was kind of a little bit taboo for a lot of people,

so it was inherently secret and provocative, okay? And then Robert Homan, who is my co-founder and the team, they had a data collection problem because it was ultimately user-generated content. 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,

after kind of hand cranking it with survey, their innovation was give to get. You show me yours, I'll show you mine. Very good. That's very clever. Very clever. And so, hey, 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. And do a company review. How is this even? How many people screwed that up where they're the only person with that position?

I guess that's- And we have protocols for that. We did have protocols for that. But it worked really. We also then solicited feedback on what it's like to work at the company. CEOs are kind of public figures. So okay, we're going to let you review the CEO performance. Yeah.

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. Another one is with another former Expedia guy, Mark Britton, we founded a company called AVO, which was in the legal space. And we decided to rate attorneys, systematically rate attorneys. This had never happened before. It was just kind of like TripAdvisor for attorneys. You can kind of TripAdvisor for anything, right? These are business models that are well-trod now, but these were kind of innovative back in the day.

And of course, we were going to get sued because we were rating attorneys. Yeah, definitely a great way to kick the horn in its nest. Some investors, when we were raising money, I remember traveling around doing the Sandhill Shuffle with Mark. And I remember some people saying, well, is this legal? Can you rape people? You're going to get sued. I'm not going to invest.

And we were like, yeah, we're going to get sued. Did you see Die Hard? You remember Die Hard, where the German terrorist leader 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 bonds out of the Nakatomi Plaza safe? And the people are like, how is he going to get the power to go down in order to be able to get the bearer bonds out of the Nakatomi Plaza safe. Yeah. And the people are like, how is he going to 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, yeah. I'm like, boom. Anyway, that was exactly the launch strategy of Ava.

I was 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 structure. Well, here, let's go with the lawsuits. All right, so the Sand Hill Shuffle, for people who don't get that reference. So Sand Hill 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 Balenciaga and Prada and all the fanciest brands, all the aspirational brands. Well, if there was such a place, but it was all the highest end venture capitalists, that would be Sand Hill Road. And now it's more distributed, but still it's a thing. Right?

Oh yeah. If you go stay at the Rosewood and you're right around the corner, that's got its own stories. That's a strange place. But fantastic. Love that. Love that bar. And then you have, you name it, right? Everybody's there. All the big players. And so that's the Sand Hill Shuffle. So why not be afraid of lawsuits? What did you guys know that the guys who said, I'm not going to touch that with a 10 foot pole.

Well, the founder CEO, Mark Britton was my general counsel at Expedia and he worked securities exchange commission prior to that. He was a real attorney. And the way we did it, we were 100% convinced of our legal grounds. Yeah. 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 lawsuits. 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 after we won the first few suits, 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 Ava? It did pretty well. It did pretty well. We had trouble. So in a kind of TripAdvisor for legal sort of way, it did really well. Ultimately, these kind of TripAdvisor-y 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. As time wore on, a lot of those business models got somewhat disintermediated.

The protection against that is usually to go down into the workflow of the transactions 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 TripAdvisor for X. Like you said, they're kind of harvesting traffic on the SEO side.

So their pages are engineered in such a way. Maybe also using ad spend to drive traffic to these reviews, which are then monetized on some level. By selling those leads out the other side of the marketplace. So literally a lead middleman. Well, Michael Porter, Five Forces would say, look, if you have an over dependency on any supply of customers, you're strategically exposed for obvious reasons. If you have an over dependency on any supplier, you're strategically

exposed. And so business strategy 101 says diversify your sources of customers and your sources of supply so that nobody gets too much leverage over you. Also, it's like a single point of failure, right? Absolutely. The factory went down because of X, Y, Z. 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. All right, so in that example, 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. 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. And so when the big guy that you're getting all your customers from starts taking 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 two-fold. One, build a giant brand that customers know and love, and therefore, most of your traffic and customers comes directly to your app insights. 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 travel or real estate or legal or jobs, you know, for the verticals that I've done stuff in, and make sure you become digitally integral to the workflow. You're building tools for the industry. 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, 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 we're embedded in the workflow, solving real customer problems and the business is great and growing.

All right. So I haven't forgotten about the provocation marketing class. However, 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 us. It really stuck with some and it didn't with others. I probably only had like 10 posts on my blog. But one of them was naming because I've had a lot

of fun naming companies. And I gave advice on naming, I think the title of the post, the site it's on is called hopperanddropper.com, which is a fly-fishing term. But, which nobody's gone to. I only had 20 visitors. Tim being one. Lucky 21. 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, you know, but I'll tell you that there are no shortcuts. You take the shortcut to the long

road, my coach Jimmy says. Anyway, the easy way is if you're building a travel site to call it hotels.com, airlinetickets.com, you name it. Every category has a literal word.com. And the advantages to that are it's easy to explain to people what you do. And the disadvantages to that are you don't own any brand equity because you can't own a word that previously exists. 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.com, 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, 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 was confident in my ability to, my and 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 points gravel letters. Do you play Scrabble? It's been a minute, but yes, I play Scrabble. Okay, you know that there are different point numbers on each letter as you play Scrabble. And do you remember what the high point ones are? They don't. Okay. They're Z is 10. X is 10. That's the highest point you can get. A, E, I, O, U are 1. Here's why. Q is 10 too. Here's why. Z, X, and Q are super rare letters. A, E, I, O, U are super common. And so rule number one is pick the super rare letters 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. So all my stuff has Zs and Xs and some Qs actually too. Rule number two, fewer syllables is better than more. I kind of learned this lesson with Expedia. Expedia was too many syllables. It's worked out fine. We've overcome that. The companies 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 things, speed, expedition. So it said adventure and speed, and that all felt good 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 onto something like you can call for it. Zillow. 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 probably, the 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 palindromes are words that are the same forward and backward spelled. So just interesting, interesting words. Anyway, that's my handbook. Palindrome, like my friend, Mike Kim 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 space. That is a funny game, isn't it? Yeah. So stupid. It's so fun. So good. So I'm thinking it? Yeah. So stupid. Yeah. So fun.

So good. So I'm thinking of double letters. So there are names Expedia had X has an X speed, good connotation with preexisting words or concepts. Maybe one syllable too long. Then you got Zillow. Zillow. That's sweet spot.

Kind of named it. I'm imagining this Labrador Retriever, right? Yeah. Zillow. And starts with a Z. Like how many words start with a Z? That's great. And two double letter LLs, soft ending. Double letter, but I'm not sure because I am not up to speed with my Scrabble, Glassdoor.

Glassdoor, in the mid, in the middle. It was pretty evocative of having people peer is transparency power to the people and transparency is a big thing. We really liked kind of 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 kind of jumps off the page. It's an interesting looking word. I would say we get a kind of a B on that, but Robert did

a very good job with marketing that. So. All right. So if you need more time, I'm not going to forget about it. The provocation market curriculum. Yeah. And it could just be one seminar. It doesn't have to be ongoing. Just if that complicates the envisioning process. 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 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. 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. It's a cheap way to lead is to scare people. Effective, but cheap. 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 or tickled or entertained. And so that is where I would head with the seminar. And then we'd end up brainstorming about getting people's ideas for that. Let's touch on briefly, mention Bill Gurley, of course, famous venture capitalist. He's been on the show, brilliant guy, also quite hilarious. And local.

And local. Hey, Bill. Yeah, yeah, he's right down 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 eboys way back in the day. 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 rocket ships everywhere. So fun. So you've spent time at and with benchmark. What led you to that?

Was that kind of biting 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. So as we chatted about before, when I was coming with my family back from sabbatical, I'm a big believer in the sabbatical in Italy and was considering the next career move.

I got to know first Bruce Dunleavy at Benchmark and then Bill and the other guys. I did read E-Boys then too, which was romantic kind of in a weird way, but for business geeks like me and you you maybe romantic And I also knew that I had a personality that did want to have my fingers in a lot of stuff Yeah, I did. I knew that I liked to do lots of things and I want to do lots of things and I could do lots of things I could think about lots of things and

so 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. 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 Lloyd Frank of doing the Zillow thing and taking the CEO title, I said, look, you know I'm gonna do a bunch of other things

too, I'm gonna start more companies and I'm gonna do the venture capital thing." He's like, all good, no problem. 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 at the time. Cloud computing hadn't happened yet. We did have Amazon, Expedia, and Microsoft. 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 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 loved that team. I love

that team to this day. How did it benefit the other things? Was it just seeing around corners, getting an idea of what's coming before most other people have a chance to? Yeah. And thinking of new ideas for companies too. But I'm a big believer, 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 board. And 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 insular probably. And you gotta give to get. If you give time and get interested in other business models, you help them, but you end up learning 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? 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 is private, it means help the CEO and the leadership team build the company. Okay, so it's really being an advisor and a coach and somebody with a lot of business building experience

to help pick the right strategy. Now, you're not running anything, but you're basically coaching the entrepreneurs who oftentimes are less experienced, sometimes not, but oftentimes less experienced. And I would always recommend assembling a board of people with real experience who are gonna be engaged. And so it's a company building exercise.

And then when fundraising, it's time to fundraise, can totally help with the next fundraising, can help with recruiting. One of the very best 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 build companies. Okay. And a public company is a little different.

Yeah. I had one thing and I've never been on a board, but yeah, no, I've dodged it, I guess, in a sense, maybe you have a negative impression. No, no, it's not a negative impression. You dodged it. Well, I feel like yeah, dodge is a strong verb to use. So that was a missile coming at you and you- I felt like I, at the time when these opportunities

have come up, that I did not have clear criteria and I don't want to commit to things reactively, 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 can- Those are probably the most, especially for a public company, those are the most important times too. When you're company building as a private company, it's a little less important.

That's good context. But it's something that I've been, not necessarily reconsidering because I've- I think you should, I think you'd be good. Okay, tell me. Well, you're a coach. Yeah. That's all it is.

Okay. I mean, it's what it primarily is. You're instinctively a coach and you have a lot of experience sets and you look for far analogies. You look for, oh, this situation here is a lot like this other situation and that makes you a good communicator and that is oftentimes what good coaching is. I shouldn't say inadvertently because it's not inadvertent, but informally do already right with a lot of the founders that I'm involved with Which is fine, too. Yeah, it's that same

In the best of circumstances it is that same way on a board Okay, and those are the only boards that I'm involved with is is those that are really there to coach and give advice. Sometimes, oftentimes, in a public company, when you get into the public markets where your responsibilities are a little different, you have these hardcore responsibilities to represent shareholders. And the only real power you have

is kind of capital allocation a little bit, and who is the CEO? Capital allocation, meaning how do they spend their funds? Raising money, spending money, usually not to the budgetary, but big, big acquisitions, whatever. Big changes in the cap table in the balance sheet that will affect shareholders. Yeah, 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? Oh, wow. Okay. So they're like the lawyers competing to have good ratings on AVO.

Kind of. Okay. And then when a board- This is something I haven't heard anything about. 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 only get sued, whatever. If 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. I've had some boards that evolve into finger pointing 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 so if I don't get a good ISS rating, which I have some of the worst there are out there, really I do. Wait, wait, who actually determines the rating? I don't really know the process and I don't really give a rip, but some survey, it's going to stick up job these things.

They- Stick up job like they rate, give us what we want or else. Look, it's like bond ratings or whatever. These ratings firms, they do ratings and then they sell consulting services to the customers. It's just a classic. And mutual funds and ETFs, whatever, hire them. 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've got very low ratings for lots of nonsensical reasons, but I don't care. I personally don't care, but a lot of, a board that's full of directors who really do care is like not as, it's not as fun. Framework for you, which you asked. Greg Maffay, who's on my board at Zillow

and who I've worked with for a long time, I mentioned already, and Jay Ho, kind of gave me the same advice. Jay's another venture capitalist who I work a lot time. I mentioned already and Jay Ho kind of 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 local? Is it fun? Is it lucrative? Yeah, it's a good place to start. Those are those are good. Yeah.

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 traveling. That's another thing that put me on the sidelines is I knew a few people who they just seemed like traveling salesmen in the sense. It was like George Clooney from Up in the Air when he's just traveling around a different city every other week. Soul crushing. Yeah. It's not quite that way.

But yeah, I mean, 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 it can be all three, trifecta score. And lucrative meaning potentially lucrative, like the businesses, you would buy the stock as a growth stock. 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 invest over time, and I suppose it depends on the state of the and stage of the company. But 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 already, you already own a chunk of the company. Yeah. So that's your compensation. And most startups, most private companies can't afford to pay. Now the late stage startups, the forever startups now, I'm sure Stripe directors make a lot

of money. Public companies, it's really just salary kind of mid cap public companies, I would guess it's 200 to $350,000 a year. Most companies for big meetings, committee meetings, whatever, not a huge chunk of time. So it's nice. And then usually they enable the directors to choose if they want it and if some part has to be in stock and some could be in cash. You know, anyway, I don't have a ton of experience with those. So fun, local, lucrative. Potentially lucrative.

Potentially lucrative. And fun has got to be like, it's a proxy for maybe it's a cool company, whatever, that's fun, but really it's the boardroom dynamic. 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, we got old factions fighting and these guys want that and these ones want that and like, you know, run away. Less game of thrones. Yeah, exactly. Like no fun. No fun.

All right. So we're drinking our carbonated Japanese citrus. Yes. Yuzu coconut water. Feeling very well hydrated and infused. And that is as smooth slash awkward a segue as possible to do a callback to something you mentioned earlier, which was da, da, da, da, da, da. And then I started paying attention to things I had neglected before that, and da, da, da, da, including health and body, things like that. So when did that happen? Was it a gradual development of wellness habits, self-care, or was there a reckoning at some point? What happened?

Yeah, I mean, I think for a lot of people, it was there a reckoning at some point? What happened? Yeah, I mean, I think for a lot of people, it's a health reckoning for them or for somebody else that kind of shocks them into, maybe an overlay of general age. The substrate is age, and ultimately everybody probably figures this out some way sooner than others.

What is your age now? I have no idea. I can't tell. I'm 57. Okay, God. Yeah. Wow. You've really held on to the youthful glow.

Everything's falling apart. Look at me. Oh, God. I'm like American History Xs of 10 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 for me it was that same thing. It was a catalyst, a pretty sudden external catalyst.

Not my health, but my wife's and children's. So I have three kids, Will, Josie, and Russell, and Josie and Russell are twins, and twin pregnancies are high risk definitionally. And so I was age maybe 35, 34 running Expedia as a really young public company CEO. The company is doing great, but I like had to deal with stuff like 9-11, during the travel business. And I had been a pretty, not quite sleep under the desk,

but kind of work all the time kind of guy for a long time because I love my work, whatever. We socialized with Microsoft people and then Expedia people and we just lived this was our lives 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. So 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, for those who understand these things, I think she was 27 weeks pregnant

out of a 40 week typical gestation period, which is very early. That's not very, very early, but it's danger early. And so we were driving 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 her OB could check her out. And she was partially dilated and did some small contractions. And Sarah thought nothing of it. You know, the shoemaker's kids have no shoes. Sarah's like, oh, fine, I'll just keep the seat reclined as we drive up to Whistler. And her doctor, Edith, said,

not only are you not going up to Whistler, you're not going home. You are gonna be admitted to the hospital and we're gonna put you on muscle relaxants. So that began a kind of a six week, very scary period of my life and her life where she was in the hospital 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 35 weeks or something, 36 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 needed to take care of myself mentally and

physically. I kind of had the realization that for sustainability, I was going to 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, IAC had just acquired the company and I made the decision at that point

but that this lifestyle was not, I didn't need it. Needed to change. And what were some of the changes? Like how did you layer things in? Did you boil ocean all at once? And I was like, all right, here are the 12 new things I'm starting. Did you layer it in?

And would you have done anything differently? I started just exploring things. The big change was we moved to Italy six months later, or maybe eight months later, and I developed a whole new set of things I did when we were living in Italy. I took up road biking, which is a very Italian, a social Italian thing to do, which was great.

It was great for making friends too. But I had a period of time after that where I was in Seattle, and I started, I remember the first real class 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 its strength and some conditioning, I guess, and really interesting and kind of a mental thing too.

I started doing that. And then I didn't hire a trainer until much later, but 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 marathons. I discovered my body was not built for, my joints were not built for marathons. Anyway, I did a bunch of things, Tim, recognizing that I felt better when my body felt better and my mind felt better when my body felt better. And it's just built over time to the age I am now where the physiology of what's happening to my body and my bone density and my muscle mass at my age, it's like I'm continually

been ramping up how much I do, A, because it makes me feel good, but B, because I'm age-wise deteriorating. If I want to snowboard, I've snowboarded 35 days this year, and it's been amazing. If I want to keep doing stuff like that, I've got to be strong. What does the current regimen look like, generally speaking? I'm sure there are exceptions, or maybe travel or go to various places, but what does the general regimen look like? Probably a couple hours total of Zone 2-y type stuff,

bike, rowing, maybe tread. My knees are not great running, but the treadmill, a softer treadmill works, but the Peloton is my favorite one there. And then weight lifting, different body parts, maybe four times a week. And then a lot of just play stuff, you know, a lot of, a lot of snowboarding and sports. 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 Chrisckout, has in one of his suggested topics for exploration since I asked him. Like you continually put yourself back in the arena.

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. 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 my family and my health is essential to my family's health too. So my family and my health and my state of mind. But I am not operating. About seven, eight months ago, after my second or third stint as CEO at Zillow, I kind of kicked myself back upstairs. 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, my joke was, I'm very much a delegator. I'm very much a pick great people and then give them lots of space. And actually a leadership development technique I often coach is for a senior leader or middle and then give them lots of space. 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 in Indonesia and you have zero connectivity for two weeks. Yeah. Okay.

Do it for two weeks and be disconnected. And your teams are going to have to figure out how to deal with stuff. That's important Because it's gonna arise. And they're gonna have to create systems and policies and rules ahead of time that will outlive the surf trip. That's true, but from a leadership perspective, sometimes the real leader of an organization is not necessarily the one with the title. And when somebody's really disconnected, the senior leader is disconnected,

leadership is sort of an emergent property, okay? And 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, 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, 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 gets a little bit of a chuckle, but I am a seriously leverage-oriented

person. So it's not that hard. Yeah. What are other ways that you identify opportunities for leverage or think about leverage? In a life context, it is just surrounding yourself with great people who care, who have skills and who care about whatever the mission is, be it building a business or building a family. Sarah is amazingly smart and capable and cares and the stuff that she's in charge of is going gonna happen well.

That's an unbelievable feature to have in a partner as you're looking for a partner. Lots of stuff matters in finding a partner, but it's really a partnership. If you guys are gonna have a baby, that's a business of sorts. I think it's mostly about picking the right people. Any recommendations for people who are hiring folks

they have not known for a long period of time? Any recommendations for the hiring process? Because a lot of people interview well who don't necessarily perform well. They know what to say. And reference checks often are conflicted. I've had the worst luck with taking reference checks at face value. There's some ways to kind of work with that.

Yeah. Two things I would say. One is my favorite section of the resume, I guess now LinkedIn. It's not really a section on LinkedIn, but it's always in the very bottom, which is the interests. Okay? And I want to get somebody, if in an interview situation, talking about their interests and why they put them there and then just asking them basic questions and watching whether or not they have any passion, you know, to see a real spark, you know, because 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 would always make up business cases around some interest. How big is the ski industry? Because you put skiing, whatever. And that was always a fun stepping off point. So finding people's passion. I want to find people who are passionate people.

And then the second thing is get used to pulling the pitcher off the mound quickly. Firing someone. Yep. Okay. It's hard when you're early in your career. It's not as hard later. All of my mistakes as a leader have been leaving, almost all of them have been leaving the pitcher

on the mound too long, hoping that the arm would get better. What have you learned in terms of process for firing? Any approach, go-to phrases, 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 he or she is gonna have to fire someone. And they're like, hey boss, I don't wanna bother you, but this is something I haven't done before. Give me some advice. Yeah, don't do it via text. Be an upstanding person, have some courage.

You gotta be face to face. But it's actually not that hard. My advice would be, 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. That person belongs somewhere else. That person's going to be happy somewhere.

Help that person find that somewhere. But you're going to be happier when you release that person, and that person's going to be happy somewhere. Help that person find that somewhere. But you're going to be happier when you release that person, that person's going to be happier too. And so if you make it a partnership, if you make it a joint decision effectively, or at least get the interests aligned, which it almost always is, 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. That means you're showing heart. And having heart in this situation is really important.

And then in terms of the delivery, the conversation, any tips on how to manage that? 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 sympathetic and non-argumentative in order to get people on the same page. 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. And then asking advice on the way out too, like for voluntary or involuntary termination. Sometimes it's hazy, right? And soliciting information on the way out for yourself and the organization is often appreciated and often revealing too.

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 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.

So random question, I don't know, you could be covered in tattoos, but what is the story of this tattoo? Family. All right. 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. It's a snowflake in total shape. And it's a starfish in the negative space. My daughter Josie, when she was 16, which is too young to get a tattoo, asked Sarah if she could get a tattoo or asked her more specifically, would she get a tattoo with her? And Sarah's like, well, you met Sarah. Like, sure. And she's like, and I bought it to me and I was like, okay, let's design one as a family. No Wiley Coyote. The first versions, you know those on the back of a minivan, the family of five with

the stick figure mom and stick figure. That was what Josie drew. V1. Josie's very creative. You're creative, honey. But it was funny. That was the first version. And we were sharing different versions and iterating.

And at some point, Sarah said, maybe we should bring 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 this. They look exactly the same, but they're not. They're all unique. They form a cohesive whole. The trees are unique too. So anyway.

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 remember my family. And we did this maybe five, six, seven years ago. I thought we'd get more. Sarah's gotten two more tattoos, but I haven't gotten any more. I think tattoos are, you don't have any?

Do you have some? It's a, very few people have one. Yeah, I have been, I've been considering getting my first, which is in some ways kind of similar. It'd actually be in very similar location, right here with my dog's paw prints. It's hard for me to imagine regretting that. You won't?

Yeah, I don't think I will. Yeah. Yeah. So. We, it was interestingly, our older boy Will was of age to get a tattoo. He was 18, I think at the time, maybe 19. 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 in Spain. And we have that house in Montana, and Montana doesn't have any restrictions. So on the way to go skiing one time, Russell went to some sketchy place in Bozeman and got the tattoos. So we got them all, we all got them in different places. It's funny.

Any other, I mean, I guess getting a tattoo is not necessarily a recommendation you're making, but any thoughts for, let's just say there are people listening who are type A or otherwise builders who can sometimes be consumed perhaps by the scale and scope of what they're doing or hope to do. And they're planning on kids or they have very young kids. What would your recommendations be to those people? For the planning arms, the kind of constant delayers, which there are a lot of, you know, maybe some right here. There are a lot of, you know, maybe some right here.

Uh, uh, there are a lot of 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. There's never a better time. There's never a good time. So point number one is

it's not going to get better. It's not going to feel better. 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, 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 going to work pretty well. And so I don't know if I call myself a birther. I'm an encourager of like, let's 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, to have children. And from a growth perspective and it kind of, as we get older, our ego focused naturally, the diameter of our egosphere gets broader and broader and children just blow it way out. And that is really a

positive for most people to realize that their needs and wants are trivial. I think that's a positive. So anyway, I encourage it. Yeah, for me, it's not a bad timing looking for better timing thing. It's more of a navigating of navigating the bizarre aspects of modern dating, being in my public slash semi-public position. And 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 not trivial.

I didn't have, I never had to deal with that, but I totally saw it as. How old were you guys when you met? 22. Wow. Yeah. Good for you. In a pub in Cambridge, Mass.

Look at that. Maybe that's my next move. Go pub crawling in Cambridge. It's hard though. I totally get what you're saying. It's hard. For the people with young kids and balancing things, 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. Because a lot of people out there are not doing that. And eventually it comes home to roost one way or another. And the sooner you can kind of keep things in perspective. 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, 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 the cloud headquartered the Matt Mullenweg. Matt was very, he was very influential on me early in the pandemic. You know, I had him blue jeans Zoom into an early company meeting early in COVID and lay out his game plan for the distributed corporation. And God was super helpful.

Yeah, Matt Mullenweg, generally associated with WordPress, founder and CEO of Automatic, spelled M-A-T-T-I-C, and pioneer of distributed workforces. And as a design principal from the outset has built that company to be distributed, and therefore was very anti-fragile when COVID came along. And there were some other standout examples.

I mean, Shopify did really well also. But you're right. I think if this can't lend itself, I mean, modern technology and the options available to some type of balance or the option to pull different levers where it would have been far difficult even 10 years ago.

Yeah. But we can generalize and say it's been great for moms, but it's more than just moms. But it has enabled 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 path. It's enabled them to come back. 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 because you're at a dentist appointment for your kid or something. As long as 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. Gotta do it this way. That's like, I kinda chuckle when I listen to all that.

I'm like, you people, open your minds. This opens doors, this doesn't close doors. Yeah, so let me ask a couple of quick questions. Yeah. Now, they don't need to have quick answers, but just as we start to land the plane, what books have you either gifted a lot to other people or reread yourself? Either one. I am not your typical person probably sitting in this seat and that maybe I am not a nonfiction

business book. Sorry, Tim. Oh, it's okay. Yeah, I tend not to read that stuff. The older I get, I occasionally will read a biography now, but they mean more now the older you get. I am fully a, I'm a big reader and it's fiction. And generally good fiction, although I do have, you know.

Cheap thrills. Yeah, 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 from the Cranked up quick twitch always on alert operational stuff that people go. Yeah, exactly to get my brain my monkey brain Okay, and to get my monkey brain to relax Escaping into a fiction novel for me is just a fantastic release. So with all that said, what stuff do I like and that I've gifted? Recently I gifted The Oceans

and the Stars. Do you know Mark Halperin? Oh no. Okay. He's a guy who's a little older than I am and writes characters that are just about in my phase of life. Like a beautiful luscious prose writer, really smart wrote, Soldier of the Great War and A Winter's Tale and Freddie and Frederica, if you've heard of any of these books. There's a little bit of magic in them.

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, just under admiral or like a low level admiral in the US Navy, who almost becomes head of the DOD but doesn't get it because he speaks his mind. And then he gets commissioned as a rebuke on this new weird ship.

And I'll just say that and that's the setup for him taking this really more fast attack destroyer into the Middle East. And he's kind of a war guy. He's a vet and he's a pretty engaged political kind of, I'd call him an offensive realist in the John Mearsheimer mold. Kind of hawkish would be perceived as hawkish, you know, believes in strong defense. The protagonist.

This is the author, Mark Alper. And he's, this is his mindset. 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, if I recommendceans and Stars is great. The only one of his that I've probably reread is A Winter's Tale, which was my first one I ever read by him.

It's just a beautiful, beautiful story of early 20th century life near New York City and upstate New York. You might actually like it. I might dig it. I read Last of the Mohicans just to take a walk through that area in that time period. Authors I like, I like Haruki Murakami kind of magic. Neal Stephenson is like,

some people don't like his latest book, Polistan. I don't know if he's the one who wrote Snow Crash. Oh yeah, oh yeah. Okay, so you know him. Snow Crash for Keeks. Had pizza with him in Seattle. With's with a couple of other guys. And I was like, wait, you do Victorian era calisthenics with, oh, and you make swords?

Wait, what? I mean, lots of. And he's got the beard down his. Oh, amazing beard, yeah. I actually kind of 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 Seattle. Yeah, he's right there. Yeah, he's right there. So I see him occasionally at our sushi place. I'm like, I get scared. But his latest Polostom, I highly recommend. Okay, I haven't read it yet. Some people are giving me grief for it. It's, you know, authors when they get successful.

7,000 pages. Well, it's long. A lot of his stuff is long pages. 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 loved. Which me too. Me too.

But authors, as they get successful, sometimes, they have too much power over their editors, and so they get a little self-indulgent, you know? Which, for me, with a beautiful prose writer, I'm like, take me along, fine, I will indulge your self-indulgence and I don't mind it. But this one takes 100 to 150 pages to break into,

but then it just goes. Then it rips. Then it rips, yeah. So anyway, I highly recommend it. And it's gonna be a trilogy. And so it's only the first one, so I'm like, I can't wait. Anyway, I love, you can tell, I love to read fiction.

And do you lean these days, if you're gifting, do you, have you gifted those books that you mentioned? I have gifted oceans and stars, but I'm such a Kindle person, and so many of us are digital readers now. It's kind of hard to gift. Yeah, it is. It's more, you know, group chat.

Yeah. You know, book group, group chat. That's how most of the book discovery happens for me now. Have you read any of Ted Chang's stuff? Uh-uh. Oh, man. Who is it? Okay, so Ted C-H-I-A-N-G.

Okay. He has, last I checked, he has two collections of short stories. There's one which I always script the title of. It's like stories of your life and other stories, something like that. OK. And one of those short stories was the basis for the movie Arrival with Oh, God, that's great. We're an amazing movie.

So one of his short stories was the basis for that. And then I read that collection and pretty much everyone who 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 tier, you know, just like, 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. I was like, there's just way. Right. Like that first one was appetite for destruction. Like, yeah, you can't do that twice. And then the second was just unbelievably good. And not all of them will hit necessarily, but the ones that hit are just incredible. And he has like one night read short story as collection of one. 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 LIU. He has the paper Menagerie, which was actually gifted to me by Matt Mullenweg, blends or alternates in a sense between sci-fi and fantasy in this really compelling way. Cool. So you get these like little ginger snacks in between your pieces of sushi. These are the sort of food 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 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 kind of wished I became a writer. I'd like to write, but I'm not that good.

And I've never dedicated time to it. But in that vein, this guy, Amor tolls, you know, okay, I've only read he was a banker. I know finance. That's well, that's another one. Until he was like 40. No, I know, finance. That's, well, that's another one. Until he was like 40. 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 Hugh Howey, shook hands with Amor very briefly at a restaurant. We happened to bump into each other. And I found out about the finest background. I was like, you gotta be kidding me. I know.

You gotta be kidding me. I learned that he was on somebody's pod. He gave a great pod when Lincoln Highway came out. Yeah. To somebody who cracks open artists. It might've been like Brian. Oh, compliment. It might've been compliment.

Yeah, very well could've been compliment. Who like gets to artists, right? Yes, who by the way, for people who don't know, a quick bit of trivia. So Brian Kaltman, co-creator of Billions and co-writer of Rounders and all these movies and TV shows and so on, also discovered Tracy Chapman as a musician

back in his A&R days. Really? Yeah. Isn't that wild? He's a talented guy. Yeah, so it wouldn't surprise me if Amor was on that show. He was on there and got him to crack up and then he was kind of surprised by Brian's questions,

I think, and didn't know Brian and all this stuff came out. Yeah. You know. Amazing. All right, this is the billboard question. If you could put anything on a billboard, message, quote, reminder, anything at all, obviously metaphorically, just to get something in front of a lot of

people. You asked this, so I did think about it a little bit. My initial response that I latched onto 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 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 and Steve Martin and Heather Graham. It's super quirky. Eddie Murphy plays two roles in it which he did for a while in Lost Movies and he plays one of his roles. He plays a paranoid Hollywood celebrity 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 setup. Steve Martin's directing. 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 And he goes to a thing that I don't know what kind of culty LA religion it's representing, but it's called Mindhead. And he goes in, he has his first counseling with the high priest of Mindhead. And the religion is based on three happy premises. I'm not going to remember them all, 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 what I was going to put on the billboard and that is, even though I feel like I might ignite, I probably won't. Okay, that goes on my billboard. That or my favorite Burning Man bar ever had that giant neon sign on top of this kind of cozy geodesic dome playing groovy 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. We'll say more. That's it. Don't panic. So that's on the billboard. Don't panic. So that's on the billboard. Don't panic.

I think a lot of my job as a leader, explicitly or naturally or otherwise, is to naturally bring people off of their high beta, high swings, high mood swings. People have a tendency towards fear and panic. And almost always it's going to be just fine. And when it's not, it doesn't matter anyway. Right. Okay? All right.

And it can cause a lot of a happier life and a calmer community and a better, healthier community and family if everybody just takes a little breath before getting scared, you know, or getting crazy. Or sending 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?

Yes, I think so. I think that led me to the don't panic. I think so. 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 modern newsfeed, iPhone, TikTok, 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. We're looking to give our brains and bodies just a break from the constant barrage and 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, you know?

That's disconnected. That's gonna be on the rise. Those are growth businesses, right? So people sheltering from the digital storm. The hail storm of doom. Exactly. It's so unhealthy, you know? Have you taken any sabbaticals since Italy?

Oh yeah. I mean, I've had multiple retirements and- Now, are those failed retirements or did those have an end point where you're like, I'm going to take a year and then I'm going to dust off my gloves and get back in the- The Italy 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 kind of built shelter into our family's routine now. So it's just a part of the normal cycle of the seasons, you know, and a really key component of that. Not always achievable, especially now. Starlink and traveling Starlink and Starlink at my surf camp and Starlink on my Airstream. It's harder and harder to disconnect, but disconnection is really a key part of it,

I think. I think disconnection, the behavior you observe when people are disconnected, like with my family when we do, we were after the Grand Canyon this year with a big group of friends and family. And when you watch the younger people, it's very unsettling for the first only like three or four hours. And then when they realize it's over, it's total mean reversion to 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. What you can't not be happy making a friendship bracelet or 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 do we, I don't want to give that away. I don't want to give your game. But you can't not be happy when you're doing that and not looking at your thumb. Yeah. Highly encourage rich Tim. So nice to see you, man. It's great to see you. We've covered a lot of ground. It was fun. Where, if people want to learn more things about Rich, should they

be visitor 22 to your blog? No, I don't think so. The blog is totally vestigial. It's an appendix that needs to be removed. Hopper and dropper. Yeah. No. Yeah. No, man. I don't, you know, the writing thing, I've had a lot of offers to do that with, I've just never felt like I enjoyed reading any of those, you know, business guy ego books, you know? I just don't find them very interesting and I don't wanna be one of those kind of jerk-offs, you know?

Maybe do a writer's retreat or an MFA, compressed MFA and take a stab at fiction, just saying. Even if you never publish anything, it's a good muscle to train for a bit just to play with it. I'm doing more creative things deliberately now and it feels good. Yeah, like I took up procreate painting on my iPad during COVID. And it's so I'm so I feel so good. And I like catch myself going back and looking at my works. And I like I've been a party and I'll show people what I painted. Yeah, it's not good. And I like catch myself going back and looking at my works. And I like got to be at a

party and I'll show people what I painted. And it's not good 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 thank you. You perform a good service. You provide a good service for a lot of people with this bottom and with your books. 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. I really just think people are just looking to lead better, happier, slightly more efficient lives, improving lives. They want to improve themselves. And you really help people do that. And 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. Awesome to have you. Everybody listening, we're going to include everything we talked about in the show notes, tim.blogslash.podcast. If you search Barton, that's going to 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 for tuning in. 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. 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,

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