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

Rich Barton is the co-founder and co-executive chairman of Zillow https://www.zillow.com/, 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 https://ramp.com/tim easy-to-use corporate cards, bill payments, accounting, and more: https://ramp.com/tim (Get $250 when you join Ramp) Cresset https://cressetcapital.com/tim prestigious family office for CEOs, founders, and entrepreneurs: https://cressetcapital.com/tim (book a call today) Shopify https://shopify.com/tim global commerce platform, providing tools to start, grow, market, and manage a retail business: https://shopify.com/tim (one-dollar-per-month trial period) Timestamps: [00:00:00] Start. [00:05:30] Eddy Cue magic. [00:06:14] Rich’s morning routine and workout philosophy. [00:13:38] How Brad Chase at Microsoft taught Rich to swing big. [00:15:46] The failed DOS for Dummies book bundle project. [00:18:52] Steering a company toward a culture of innovation. [00:20:26] Rich’s journey from management consulting to Microsoft. [00:24:34] How Expedia came to be. [00:32:32] Pitching and recruiting team talent. [00:37:18] Degree design at Stanford. [00:39:45] Realizing the value of real work as a youth. [00:41:44] A fascination with Italy. [00:43:01] Selling Expedia to Barry Diller/IAC. [00:43:51] Dara Khosrowshahi’s role in Expedia’s acquisition. [00:45:23] From a post-Expedia sale sabbatical in Italy to the birth of Zillow with Lloyd Frink. [00:55:41] “Big pond, good fishermen” as business criteria. [00:56:50] Early Zillow mistakes. [01:00:05] The Zestimate: Zillow’s killer feature. [01:01:29] Making lemonade from the lemons of Zillow’s launch day server crash. [01:03:49] Rich’s provocation marketing playbook. [01:05:30] Regulatory battles and resistance to industry disruption. [01:10:44] Founding Glassdoor and its “give to get” data collection model. [01:12:58] Avvo and rating attorneys — legal challenges as marketing. [01:16:11] Digital marketplaces and Google disintermediation concerns. [01:19:52] How Rich names companies to be memorable. [01:25:28] Why Rich recommends leaving fear out of the provocation marketing equation. [01:26:48] Working with Benchmark Capital. [01:30:37] What serving on a board looks like and Rich’s membership criteria: “Is it local? Is it fun? Is it lucrative?” [01:39:00] Rich’s motivation and regimen for staying healthy in his 50s. [01:47:13] Cultivating leadership through absence — the two-week disconnected trip. [01:49:34] Building a good company by keeping good company. [01:51:42] Developing the skill to fire people as a win/win proposition. [01:54:41] Rich’s family tattoo design and symbolism. [01:57:29] Advice for balancing family and professional life. [02:01:08] The benefits of distributed workforces post-pandemic. [02:03:23] Recommended reading. [02:12:17] Rich’s billboard. [02:14:25] The importance of sabbaticals and disconnecting from digital devices. [02:17:41] Taking up Procreate digital art during COVID. [02:19:05] Parting thoughts. * For show notes and past guests on The Tim Ferriss Show https://tim.blog/podcast, please visit tim.blog/podcast https://tim.blog/podcast/?utm_source=podcast&utm_medium=podcast&utm_campaign=podcast-description. For deals from sponsors of The Tim Ferriss Show https://tim.blog/podcast, please visit tim.blog/podcast-sponsors https://tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday https://go.tim.blog/5-bullet-friday-1/. For transcripts of episodes, go to tim.blog/transcripts https://tim.blog/transcripts. Discover Tim’s books: tim.blog/books https://tim.blog/books. 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Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Tim Ferriss?

  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 Saka and some other guests we've had. He is the co-founder and co-executive chairman of Zillow, a company transforming how people buy, sell, rent, and finance homes. Before Zillow, Rich founded Expedia within Microsoft in 1994 and successfully

• 0:41Tim Ferriss?

  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,

• 1:25Tim Ferriss?

  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 Work Week, 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, blah, blah, blah, then you want to get rid of as much as possible, eliminate. But sometimes there are things that are a huge hassle, like expense management for a lot of companies, which you can't get rid of. They are essential to your business. But today, thank God, you can automate it, and there is no better way to do that than with today's sponsor, Ramp. Ramp is a free corporate card that automates

• 2:10Tim Ferriss?

  Your entire expense process. They are incredibly fast growing and incredibly well reviewed for good reasons. The moment your team makes a purchase, Ramp handles everything. Receipt matching, categorization, approval, the whole works. Switching to Ramp is like hiring a full-time employee just for expense management. And Ramp makes it easy to migrate from your current corporate card with their complimentary white glove onboarding service for new members. More than 25,000 businesses trust Ramp, including my good friends at Shopify and the Boys and Girls Club of America, which is why they were just named number one in spend management by G2. And now for a limited time, you guys, listeners of the Tim Ferriss Show can get $250 when you

• 2:54Tim Ferriss?

  join Ramp. Just go to ramp.com/tim. That's R-A-M-P dot com slash tim. Cards issued by Sutton Bank, member FDIC. Terms and conditions apply. Listeners have heard me talk about making before you manage for years. All that means to me is that when I wake up, I block out three to four hours to do the most important things that are generative, creative, podcasting, writing, etc. Before I get to the email and the admin stuff and the reactive stuff and everyone else's agenda for my time. For me, let's just say I'm a writer and entrepreneur. I need to focus on the making to be happy. If I get sucked into all the little bits and pieces that are constantly churning, I end up feeling

• 3:38Tim Ferriss?

  stressed out. And that is why today's sponsor is so interesting. It's been one of the greatest energetic unlocks in the last few years. So here we go. I need to find people who are great at managing. And that is where Cresset Family Office comes in. You spell it C-R-E-S-S-E-T. Cresset Family Office. I was introduced to them by one of the top CPG investors in the world. Cresset is a prestigious family office for CEOs, founders, and entrepreneurs. They handle the complex financial planning, uncertain tax strategies, timely exit planning, bill pay, wires, all the dozens of other parts of wealth management and just financial management that would otherwise pull me away from doing what I love most, making things, mastering skills,

• 4:23Tim Ferriss?

  spending time with the people I care about. And over many years, I was getting pulled away from that stuff, at least a few days a week, and I've completely eliminated that. So. Experience the freedom of focusing on what matters to you with the support of a top wealth management team. You can schedule a call today at cressetcapital.com/tim. That's spelled C-R-E-S-S-E-T, cressetcapital.com/tim to see how Cresset can help streamline your financial plans and grow your wealth. That's cressetcapital.com/tim. And disclosure, I am a client of Cresset. There are no material conflicts other than this paid testimonial. And of course, all investing involves risk, including loss of principal. So do your due diligence.

• 5:07Tim Ferriss?

  At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question?

• 5:14Speaker 01

  Now would be an appropriate time.

• 5:18Speaker 02

  I'm a cybernetic organism, living tissue over metal endoskeleton.

• 5:30Speaker 01

  I know Eddie Q a little bit, his 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, you know, CNBC quietly on mute. And at one point, a couple of years ago, I moused off the left edge of the screen and it seamlessly went onto the, and my, all of a sudden, my mouse was 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.

• 6:09Tim Ferriss?

  Yeah.

• 6:09Speaker 01

  And I texted him immediately. I'm like, oh, Eddie.

• 6:14Tim Ferriss?

  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?

• 6:26Speaker 01

  It's my favorite source of news because business news is generally happy.

• 6:32Tim Ferriss?

  Yeah, got it.

• 6:33Speaker 01

  To just don't wallow in the bullshit.

• 6:36Tim Ferriss?

  Yeah.

• 6:36Speaker 01

  And regular news makes me feel bad.

• 6:39Tim Ferriss?

  Yeah.

• 6:40Speaker 01

  And CNBC. At best makes me feel good and most of the time is just mid. That's fine, you know, and I get the news. I'm interested in business and companies and strategy and trends and, you know, 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. So I usually don't have the volume on. I have the closed caption scrolling. And then if something catches my eye, I'm gonna go do it.

• 7:05Tim Ferriss?

  So let's take a closer look then at the other screen.

• 7:09Speaker 01

  Yeah.

• 7:10Tim Ferriss?

  You have your coffee?

• 7:11Speaker 01

  Yeah, yeah.

• 7:12Tim Ferriss?

  What time is this?

• 7:13Speaker 01

  Yeah, I'm a pretty early riser.

• 7:15Tim Ferriss?

  Mm hmm.

• 7:15Speaker 01

  6:30 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.

• 7:24Tim Ferriss?

  Prestige.

• 7:25Speaker 01

  My kids have all left the house now. There was a routine when my kids were in the house. It was obviously very different and really fun. I can talk about that, but now I have two hours of just catch up on the stuff in my news feed, 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.

• 7:52Tim Ferriss?

  What's the stuff?

• 7:54Speaker 01

  No supplement kinds of things, but lots of

• 7:57Tim Ferriss?

  Cat testicles?

• 7:59Speaker 01

  I am not, I am not one of those guys. I am not one of the, you know, longevity supplement people, but I'll tell you what's in it. It's about three or four ounces of oat milk, 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.

• 8:31Tim Ferriss?

  Yeah, the blue can, man. I had a lot of that when I lived there as an exchange student.

• 8:36Speaker 01

  My nutritionist says that's the one.

• 8:38Tim Ferriss?

  Yeah.

• 8:39Speaker 01

  And I'm like, okay, I'd been taking another one, using another one. She's like, no, this is the one. And not much, a prune.

• 8:46Tim Ferriss?

  Prune.

• 8:46Speaker 01

  Prune because

• 8:48Tim Ferriss?

  Keeps things moving.

• 8:48Speaker 01

  Keeps things moving and that's very important. You know, young people out there don't really realize how important that is yet. When they're your 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've bought a bunch of products, but there's a back one called the Venom. You must have run into that.

• 9:14Tim Ferriss?

  I think it heats and vibrates.

• 9:16Speaker 01

  Yes.

• 9:17Tim Ferriss?

  Yeah.

• 9:19Speaker 01

  So I actually, for my whole kind of 45 minutes of that routine at the kitchen table, you know, with a lot of light coming in as soon as the sun's up. I have it on repeat. I'm wearing that Venom. Oh my God, that loosens everything up.

• 9:33Tim Ferriss?

  And you mentioned before your workout, so this is all pre-workout?

• 9:37Speaker 01

  Yeah, I need to get things going and feel settled, a little bit settled and brain on before I work out.

• 9:47Tim Ferriss?

  Coffee helps too.

• 9:48Speaker 01

  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.

• 9:59Tim Ferriss?

  Yeah, got it.

• 9:59Speaker 01

  So I go through that and once everything's, you know, make my ablutions and change into my, into my workout stuff.

• 10:07Tim Ferriss?

  Rinse your face with some holy water.

• 10:09Speaker 01

  And pretty much every day I do a workout. I can't really get my mind right without that.

• 10:14Tim Ferriss?

  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 short straw on 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. Like in other words, there are a few things that really matter, but then there's a long tail of things of questionable value that also have unknown, uncharted side effects.

• 10:55Speaker 01

  Yeah.

• 10:56Tim Ferriss?

  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.

• 11:07Speaker 01

  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, you know, 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.

• 11:34Tim Ferriss?

  Yeah.

• 11:34Speaker 01

  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 cooktop is on the other side. And whenever the kids wandered downstairs bleary eyed, I was their short order breakfast chef and anything they wanted, I would make, which was so fun.

• 12:07Tim Ferriss?

  It was like the breakfast buffet at the Four Seasons or something.

• 12:10Speaker 01

  Whatever they wanted, I had it, I could whip it up really, really fast because you get that skill wasting when you're a short order chef. I have my younger boy had some kind of ADHD stuff and started taking those, the meds. I can't remember how old he was, 10, 12. And those meds make kids, it's an appetite suppressant.

• 12:30Tim Ferriss?

  Oh, for sure.

• 12:30Speaker 01

  Okay. So maybe, you know, and I was a typical parent, our primal urge is to feed our children. That's it, like feed and care for our children. That is the overriding program that kind of puts everything else down. And so I got to the point where I was so worried about how skinny he was and he wasn't eating the rest of the day. He was hungry in the morning and I would like make a 12 egg frittata and like put potatoes in it and sausage in it and he'd down the thing and I'm like, okay.

• 13:00Tim Ferriss?

  It's been accomplished.

• 13:01Speaker 01

  Yeah.

• 13:01Tim Ferriss?

  The anaconda diet, just one huge meal and it works.

• 13:05Speaker 01

  Yeah. And the punctuation on this one, aside from that just being really quality time, regardless of what kind of mood the kids were in, it was just really quality, I cherished it. I took a picture most days.

• 13:17Tim Ferriss?

  Hmm.

• 13:18Speaker 01

  Okay. Totally candid, there's no posing, I would sneak a picture every day. And now I have a folder called the breakfast club on my, you know, in my picture, my iPhone pictures and I have like a thousand pictures. And it's a time series of these kids growing up.

• 13:34Tim Ferriss?

  Yeah.

• 13:35Speaker 01

  It's a virtual possession, but it's my most prized possession.

• 13:38Tim Ferriss?

  All right, we're going to double click on a bunch of things we passed over.

• 13:41Speaker 01

  Yeah.

• 13:42Tim Ferriss?

  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?

• 13:55Speaker 01

  Brad Chase?

• 13:56Tim Ferriss?

  Yeah. What impact did he have on your life?

• 13:59Speaker 01

  And 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, you know, 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.

• 14:19Tim Ferriss?

  And just for reference.

• 14:20Speaker 01

  Yeah.

• 14:21Tim Ferriss?

  Because I have no idea, how many employees do you think they have now?

• 14:26Tim Ferriss?

  It's going to be a multiple of that, of course.

• 14:29Speaker 01

  Three, 300, 400,000.

• 14:30Tim Ferriss?

  Yeah, orders of magnitude.

• 14:31Speaker 01

  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 going to engage on the geeky stuff, but 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.

• 15:16Speaker 01

  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.

• 15:46Tim Ferriss?

  Is this the book project?

• 15:48Speaker 01

  Yeah.

• 15:48Tim Ferriss?

  You want to tell people about it?

• 15:50Speaker 01

  Well, I don't know how that interesting is, other than the lesson of take big swing.

• 15:53Tim Ferriss?

  It is, but the details help paint a picture, right? People can conjure a visual in their head.

• 15:58Speaker 01

  All right. It's become a huge series. It was a series for dummies, Blank for Dummies.

• 16:02Tim Ferriss?

  Yep.

• 16:03Speaker 01

  And the book that the dummy series was founded on was DOS for Dummies, believe it or not. It was like the best selling book about software of all time. 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.

• 16:31Tim Ferriss?

  Sure.

• 16:31Speaker 01

  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.

• 16:52Tim Ferriss?

  Seems reasonable.

• 16:53Speaker 01

  And distribute it through bookstores. How brilliant. And so I went and met with like one of the Rigio guys at Barnes and Noble. I met with the guy who created the dummy series, this guy John. So I met with all these people. We designed the product. It was really, I was, you know, feeling pretty like a big deal. Built a bunch of it that probably cost us eight to 10 bucks a unit.

• 17:17Tim Ferriss?

  Yeah.

• 17:17Speaker 01

  Okay, which is a lot for COGS, right?

• 17:19Tim Ferriss?

  Yeah.

• 17:20Speaker 01

  Cost a good sold. I can't remember how many we built, but it was at best a C, you know, maybe a D.

• 17:29Tim Ferriss?

  What was the retail price?

• 17:31Speaker 01

  You hit the problem. The problem was.

• 17:34Tim Ferriss?

  People are going in to buy a $12 book?

• 17:36Speaker 01

  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 kind of made it look like a book.

• 17:47Tim Ferriss?

  Yeah.

• 17:48Speaker 01

  Wasn't the greatest cover. Anyway, I kind of, I'm embarrassed about what it looks like now. I have one, of course, as a reminder, but yeah, it was just, it was too, the shock value was too much. People didn't realize there was software in it. And so we ate, we ate a bunch. 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.

• 18:29Speaker 01

  But Brad Chase, back to Brad, sat me down. I thought I was for my review and I thought I was gonna, who knows? It was a 10, 20 million dollar mistake, you know? And I was a young kid and he said, I remember distinctly, he said, all right, what's your next big idea?

• 18:46Speaker 01

  Amazing. That is, that Microsoft was and is an amazing organization because of that kind of culture.

• 18:52Tim Ferriss?

  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.

• 19:09Speaker 01

  Yeah.

• 19:09Tim Ferriss?

  Right?

• 19:09Speaker 01

  Yeah.

• 19:10Tim Ferriss?

  How do you think about enabling people to innovate? You don't want learned helplessness where they're afraid to do anything.

• 19:17Speaker 01

  Right.

• 19:17Tim Ferriss?

  At the same time, you don't want some rogue trader like

• 19:21Speaker 01

  That's right.

• 19:22Tim Ferriss?

  Bear Sterns or whatever.

• 19:24Speaker 01

  Yeah, it's really hard, but everything ultimately boils down to the people that you hire and the people you choose to work with and the people you keep. And saying your culture is XYZ 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.

• 20:09Speaker 01

  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.

• 20:19Tim Ferriss?

  The foreign bodies so they don't get rejected by the

• 20:21Speaker 01

  That's right.

• 20:22Tim Ferriss?

  corporate immune system.

• 20:23Speaker 01

  Which is just, it's just natural.

• 20:24Tim Ferriss?

  Yeah.

• 20:24Speaker 01

  You know?

• 20:26Tim Ferriss?

  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?

• 20:35Speaker 01

  It was, I was, you know, I was one of these high performers.

• 20:39Tim Ferriss?

  Confession coming.

• 20:40Speaker 01

  Yeah, I was just one of those kids, you know, I went to Stanford and was an engineer.

• 20:46Tim Ferriss?

  Management consulting?

• 20:46Speaker 01

  Yeah.

• 20:47Tim Ferriss?

  Really odd.

• 20:48Speaker 01

  Yes.

• 20:48Tim Ferriss?

  No.

• 20:48Speaker 01

  And I don't want, I know, but it was funny. There's a good story here. Um, I mean, I don't know if it's a good story, but we'll tell it.

• 20:56Tim Ferriss?

  Yeah.

• 20:56Speaker 01

  Yeah, man, I was like success kid, like do well, loved that, identified that way. And so of course, whatever the hardest job that came to interview at Stanford when I was a senior, of course, that's the job I wanted. 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.

• 21:29Tim Ferriss?

  But like BCG or who's?

• 21:31Speaker 01

  It was a spin off of BCG.

• 21:32Tim Ferriss?

  Okay.

• 21:33Speaker 01

  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, 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, you know, she didn't get the big job, but she got this little tech company in Seattle, you know, Microsoft, which of course I knew, like 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, that would have been, yeah, we, you know, 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.

• 22:17Speaker 01

  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 gotta come out here, you gotta come out here. And so it took about a year to finally get the flight out and the job offer.

• 22:37Tim Ferriss?

  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?

• 22:44Speaker 01

  Yes, yes, yes, yes, yes, yes. You know, a trite answer would be dressing up in a suit and tie and wearing uncomfortable shoes. Wasn't for me. I like to go barefoot.

• 22:53Tim Ferriss?

  Yeah.

• 22:54Speaker 01

  That really wasn't what it was, you know? It kind of makes you feel important when you dress up and I was like presenting things to CEOs and stuff. And it did feel important and I got like a really good business school education in competitive strategy. You know, the Michael Porter stuff. I basically got a 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. It was, I believe the world is somewhat divided. It isn't totally binary, but it's a continuum, but it's maybe a barbell. Clients and servers. Okay. Which is kind of a geeky, geeky software architecture reference, but people get it. There are all of these industries that are set up to be service provision industries.

• 23:40Speaker 01

  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, when I was a consultant. So it was, 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.

• 24:19Tim Ferriss?

  Yeah.

• 24:20Speaker 01

  Uh, and then I got to Microsoft and it was like, I was a kid in a candy store. I never left the place.

• 24:25Tim Ferriss?

  Thank God for Nina, was it?

• 24:27Speaker 01

  Nina.

• 24:28Tim Ferriss?

  Wow. I hope she still gets a box of chocolates.

• 24:32Speaker 01

  We're still close. She's great.

• 24:34Tim Ferriss?

  All right. So let's talk about then Microsoft.

• 24:39Tim Ferriss?

  And Expedia, how does this happen? I'll just leave it broad.

• 24:44Speaker 01

  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 residency, OB-GYN residency in Seattle where I lived, with only six or seven residents a year in one of the most attractive residencies in the country. So, super competitive.

• 25:28Speaker 01

  We were engaged and then soon married after that. We got married pretty young. And I was like, well, she's not going to match out here in Seattle. So, I better get ready to move to New York City or, you know, this probably would have been New York City where she matched. This was during the Windows 95 launch. I left the Windows 95 team and I went to the consumer division at Microsoft, which was kind of small.

• 25:52Tim Ferriss?

  Now, 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?

• 26:02Speaker 01

  At great companies, it's relatively easy.

• 26:04Tim Ferriss?

  Relatively easy.

• 26:04Speaker 01

  Especially for people who are tagged as high potential.

• 26:07Tim Ferriss?

  Yep.

• 26:07Speaker 01

  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. Or maybe one of the biggest product launches of all time. I don't know if you remember that.

• 26:22Tim Ferriss?

  I do.

• 26:22Speaker 01

  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. Okay, like that just wasn't gonna happen for reasons that, you know, we don't need to get into, but the government made clear to Microsoft at one point. So I figured it was gonna be a consumer software company and I wanted to go learn that. Mm hmm. And the folks over there were fantastic. Microsoft was fantastic and I took on a portfolio

• 27:05Speaker 01

  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 like CDs. It's the artifact that your doctor gives you.

• 27:24Speaker 01

  It was what it was what the last, what came in the red envelopes at Netflix. Anyway, so but 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 is really good. You take a whole bookshelf, a whole shelf of travel guides, cram it down onto one CD-ROM, pictures, audio. Wow, what could be better for travel planning? And that was one of them. And I remember going into my first product review with Bill Gates and others, which was a kind of every six months, every year kind of thing that the

• 28:06Speaker 01

  product people did. And I was used to like business plans with billions of dollars from the operating system group. And I was responsible for this thing. And I'm like, Bill, like, this is tiny. The whole travel book industry in the US is maybe a hundred million dollars. 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, like the laptop at that point was this compact suitcase that weighed 20 pounds. I'm like, that's when you want the travel guide 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 Easy Saber on Prodigy. Prodigy was an online service. Oh, yeah. Okay, and I was a Bringing back your memories.

• 28:51Speaker 01

  Geeky online guy, right. And Easy Saber was a tool for travel agents to use at home on Prodigy to access the airline reservation systems. Okay, so it wasn't meant for consumers. But I could get access to it on Prodigy. And I demoed that for him. He actually knew about it. I demoed that for him. I'm like, this is a change 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 going to have to move to New York because my wife, she's not going to match out here. And this doesn't want to be a Microsoft business anyway. It's travel first, software second, not software first, travel second. He agreed with all that.

• 29:36Speaker 01

  He thought it was an awesome idea. He also liked that we could rebuild all the mainframes on Windows NT, which is a different conversation. So he loved it. He greenlit it. He was my first venture capitalist. He said, no, don't go do it on the outside. Do it here. We have a great team that we'll put together. And I'm sure Sarah will match her residency at University of Washington.

• 29:57Tim Ferriss?

  High degree of confidence.

• 29:59Speaker 01

  That was the end of that. She did match. I honestly, to this day, don't know if there was any thumb on the scale. I doubt there was, he had that kind of power, but she matched. I stayed in Seattle. He had promised me that he'd consider spinning it out if it got big enough. And then that's what happened. So we spun in the height of the internet bubble, which is so bubbly that people today who think we're in a bubble have no concept. I mean, you remember.

• 30:21Tim Ferriss?

  Oh, yeah. I moved out right before the Thelma Lewis car went off the cliff. I mean, I moved out to the Bay area in 2000.

• 30:30Speaker 01

  It was crazy.

• 30:31Tim Ferriss?

  Impeccable timing.

• 30:33Speaker 01

  We all thought we were the smartest people in the world. We really did. 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 in travel. And Steve like laughed at me like, no, we don't do that. I said, well, dogshit.com is going public right now at 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. You know, put it on the web.

• 31:16Speaker 01

  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, a human resources experiment, too.

• 31:29Tim Ferriss?

  Now, just explain for folks, why does spinning something out make sense? What are the advantages of doing that to them and to you?

• 31:36Speaker 01

  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.

• 31:47Tim Ferriss?

  Unlocking value, meaning?

• 31:48Speaker 01

  It's not getting valued by the shareholders as being part of Microsoft.

• 31:52Tim Ferriss?

  Right. But if you, if you take it public or do something outside of Microsoft, all of a sudden?

• 31:57Speaker 01

  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.

• 32:40Speaker 01

  And as long as Windows NT, the operating system, succeeded, or Office, Microsoft Office succeeded, they could make a lot of money off their stock options. 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.

• 33:18Tim Ferriss?

  God, this was like a talent retention pitch.

• 33:20Speaker 01

  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 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 guys, all but two people decided to come, take the adventure, give it a rip. I was 32 years old, 31, 32 years old.

• 33:47Tim Ferriss?

  Now, were you pitching those people yourself?

• 33:50Speaker 01

  Yeah.

• 33:51Tim Ferriss?

  What was the pitch? Because it's going to be different than the pitch to Ballmer, right?

• 33:55Speaker 01

  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.

• 34:11Tim Ferriss?

  Mm-hmm.

• 34:11Speaker 01

  Okay. And so this was all about the adventure. The hardest sell was not the people, it was the spouses.

• 34:17Tim Ferriss?

  Ah-ha.

• 34:18Speaker 01

  And I remember several dinners, like with an S1, for those who know, it's an IPO document, with our Expedia draft of the S1 lying on a dinner table at Wild Ginger in Seattle with a skeptical spouse.

• 34:31Tim Ferriss?

  Mm-hmm.

• 34:32Speaker 01

  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. I mean, obviously, digital travel agent made a lot of sense.

• 34:50Tim Ferriss?

  Yeah.

• 34:51Speaker 01

  And so when Thelma and Louise went off the cloud, as you say, we were already public, okay, and we'd gone to the moon, the stock price had gone to the moon, we crashed back down, but we had a real business and very shortly popped back up on the climb and just climbed from there. We're 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.

• 35:22Tim Ferriss?

  How long did it take Expedia to recover or to get back on the climb?

• 35:27Speaker 01

  I mean,

• 35:28Tim Ferriss?

  Not 17 years.

• 35:29Speaker 01

  To re-achieve the all-time high, probably a couple of years.

• 35:31Tim Ferriss?

  Yeah, but a couple versus 17.

• 35:33Speaker 01

  Yeah, but the valuations were a bit nutty, right?

• 35:36Tim Ferriss?

  Yeah.

• 35:36Speaker 01

  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.

• 35:55Tim Ferriss?

  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. Whether you're a garage entrepreneur or getting ready for your IPO, Shopify is the only tool you need to start, run and grow your business without the struggle. And once you've reached your audience, Shopify has the internet's best converting checkout to help you turn browsers into buyers.

• 36:37Tim Ferriss?

  Shopify powers 10% of all e-commerce in the United States. And Shopify is truly a global force as the e-commerce solution behind Allbirds, Rothy's, Brooklinen and millions of other entrepreneurs of every size across more than 170 countries. Plus Shopify's award-winning help is there to support your success every step of the way. If you have questions. Established in 2025 has a nice ring to it, doesn't it? So sign up for your $1 per month trial period at Shopify.com/Tim, all lowercase. Go to Shopify.com/Tim to start selling today with Shopify. One more time, Shopify.com/Tim.

• 37:19Tim Ferriss?

  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.

• 37:34Speaker 01

  Persuasion.

• 37:35Tim Ferriss?

  Yeah. How did you develop that?

• 37:37Speaker 01

  It just must've 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.

• 37:52Tim Ferriss?

  What type of engineer?

• 37:54Speaker 01

  I was.

• 37:54Tim Ferriss?

  Initially?

• 37:55Speaker 01

  The story there kind of answers the question. I was an industrial engineer theoretically, but I wanted to go study in Italy my junior year.

• 38:03Tim Ferriss?

  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?

• 38:11Speaker 01

  It's not a degree anymore at Stanford. It's called management science and engineering. And then there's a kind of symbolic systems things. The industrial engineering degree, which kind of sunsetted, was really a kind of manufacturing efficiency.

• 38:24Tim Ferriss?

  I got it. Okay.

• 38:25Speaker 01

  Okay. Optimization, simulation, lots of computer work going in because it's the design of making things more efficient.

• 38:32Tim Ferriss?

  Yeah, kind of like the operations, research, finance department at other places.

• 38:36Speaker 01

  That's right. Yeah. I did it just because it was a bachelor of science, not a bachelor of arts, and it was the most business-y of the engineering disciplines. At Stanford, they called it imaginary engineering because the mechanical and the electrical folks didn't respect us. And 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.

• 39:04Tim Ferriss?

  Already at that point?

• 39:05Speaker 01

  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.

• 39:13Tim Ferriss?

  You mentioned Italy in passing, so we're going to come to Italy. But how did you get that exercise when you were younger?

• 39:20Speaker 01

  I went to Italy, so I got off the industrial engineering track. And Stanford was awesome. I came back and I'm 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 we designed, I designed one. So my degree is called general engineering colon industrial economics.

• 39:44Speaker 01

  Anyway, you know, 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.

• 39:53Tim Ferriss?

  So we were talking like busboy?

• 39:54Speaker 01

  Yeah, I mean, my daughter, I was 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 in Montauk.

• 40:04Tim Ferriss?

  Once it got fancied up.

• 40:05Speaker 01

  It got super fancied.

• 40:06Tim Ferriss?

  Took away the day passes for the locals, you bastards. Anyway, yeah.

• 40:11Speaker 01

  Uh, yeah. So she was, it was after her sophomore year in college, I think, or freshman, yeah, sophomore year. And I'm like, honey, you've got a place to stay out in the Hamptons. You don't need to get on the track, the track that every smart kid is supposed to take. You don't need to do that. Why don't you get real experience? So she came and lived in our house out in Montauk and was the, who's the person that stands at the counter when?

• 40:37Tim Ferriss?

  The hostess?

• 40:38Speaker 01

  The hostess at the club part of Gurney's. Okay, where it was like thousand, $2,000 tables.

• 40:44Tim Ferriss?

  Yeah, yeah, that's quite an education.

• 40:45Speaker 01

  It's an amazingly human nature job.

• 40:48Tim Ferriss?

  Oh, my God.

• 40:49Speaker 01

  She had a crazy, successful, interesting learning experience.

• 40:53Tim Ferriss?

  Yeah.

• 40:54Speaker 01

  Yeah, and we had fun watching it happen. And we also got tables set.

• 40:59Speaker 01

  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.

• 41:36Tim Ferriss?

  Wow.

• 41:37Speaker 01

  Summer painting. And that was a boatload of money.

• 41:39Tim Ferriss?

  Yeah.

• 41:40Speaker 01

  And so I had run my own businesses.

• 41:42Tim Ferriss?

  Mm hmm. Got it. All right.

• 41:43Speaker 01

  And who I like.

• 41:44Tim Ferriss?

  And why did you go to Italy at all?

• 41:46Speaker 01

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

• 41:55Speaker 01

  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 were public and Barry Diller bought it. And we had three little kids and I was leaving after Barry bought, 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.

• 42:40Speaker 01

  In fact, Nina, who I was talking about before, she was living there, married to a European guy. Uh, and I'd gone to Stanford there when I was a junior and I had kept in touch with the woman who ran the Stanford program, Linda. 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.

• 43:01Tim Ferriss?

  Let's take closer look at the Barry Diller transaction.

• 43:05Speaker 01

  Yeah, yeah.

• 43:06Tim Ferriss?

  How did that come to be? And what were the most important aspects of that deal? Could be deal structure, it could be timing, it could be anything, but how does that even happen?

• 43:16Speaker 01

  Yeah, so Expedia had been public for maybe four years.

• 43:19Tim Ferriss?

  Hmm.

• 43:20Speaker 01

  And had become very successful and pretty big, you know, pretty highly valued in the market. And I think it came about, I mean, Barry was kind of interested. He was building a interactive conglomerate called IAC, right? USA Networks and then.

• 43:38Tim Ferriss?

  I think he owns most of the popular dating apps, things like that. I mean, IAC buys a lot of stuff.

• 43:42Speaker 01

  And then spun it out as Match.com.

• 43:44Tim Ferriss?

  Yeah.

• 43:44Speaker 01

  You know, 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 fricking guy who worked for him was a young guy named Dara Kazashahi.

• 44:01Tim Ferriss?

  Ah, okay.

• 44:03Speaker 01

  And I, I think this, I don't, 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. And Microsoft was the majority owner, but didn't have anybody on the board, even there. You own 65% of the company, didn't have anybody on the board. Greg, they knew me and they trusted Greg Maffei, who had left SCFO, was running the company now.

• 44:34Tim Ferriss?

  Unbelievable level of trust.

• 44:36Speaker 01

  It just didn't matter to Microsoft, right?

• 44:38Tim Ferriss?

  Yeah, I guess.

• 44:38Speaker 01

  It just didn't matter.

• 44:39Tim Ferriss?

  Just as a percentage of the total.

• 44:40Speaker 01

  And at some point, somebody came in, I won't name names, somebody came in and said, "We need to focus at Microsoft. We need to get things focused. We're too scattered." And an easy thing to do was to take a big offer from Barry Diller. And so they, they did. It was a bit of a two-step deal. The 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, for the rest of it.

• 45:11Tim Ferriss?

  Under.

• 45:11Speaker 01

  And consolidated it down. We, or I think they kind of pushed us to buy the number two player, which was hotels.com.

• 45:19Tim Ferriss?

  Hmm.

• 45:20Speaker 01

  And so we mashed those things together and I moved on at that point.

• 45:23Tim Ferriss?

  So when in that journey, the Expedia journey, did you feel the highest high? Like, for instance, I would imagine when you were working summers and on your way sort of through high school and college, there was probably a moment, I'm just guessing here, but when you had your first big summer with that.

• 45:43Tim Ferriss?

  Painting gig and made fifteen, twenty grand.

• 45:45Speaker 01

  Yeah.

• 45:46Tim Ferriss?

  Like, my God, you must have felt rich.

• 45:48Speaker 01

  Yeah, we went to the highlight. You know, the highlight is?

• 45:50Tim Ferriss?

  Yeah.

• 45:51Speaker 01

  Took the crew to the highlight.

• 45:53Tim Ferriss?

  Yeah. So with the Expedia journey.

• 45:55Speaker 01

  Yeah.

• 45:56Tim Ferriss?

  Was it the tail end with the Barry Dill transaction?

• 46:00Speaker 01

  No.

• 46:00Tim Ferriss?

  No.

• 46:01Speaker 01

  Cause that's mixed emotions there, right?

• 46:02Tim Ferriss?

  Yeah.

• 46:03Speaker 01

  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, I mean, 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 roadshow. Okay, so this is November of nineteen ninety nine. It's really pitching to the buy side, so it's pitching to the mutual funds.

• 46:31Tim Ferriss?

  To the mutual funds.

• 46:32Speaker 01

  To the investors.

• 46:33Tim Ferriss?

  Okay, got it.

• 46:33Speaker 01

  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. And it was fifteen cities over three weeks, five meetings a day, six meetings a day. Chartered private plane with banker team and CFO and CEO zipping around the country. Okay, exhausting and exhilarating and repetitive and kind of boring, also really fun. Anyway. So Sarah was pregnant and she wasn't due until December, but we had been on the road for two and a half weeks already. We'd filled the book thirty times over, which means we had a lot more demand. We knew the offering was going to be successful.

• 47:18Speaker 01

  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 roadshow 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 three AM.

• 47:43Speaker 01

  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.

• 48:05Speaker 01

  And then we went to the hospital and while the IPO was happening, my son was being born. That was, yeah, my, my, my, my oldest was being born. And so that was actually the high point right there.

• 48:15Tim Ferriss?

  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

• 48:26Speaker 01

  Naked, it was a naked woman. It was like, it was like drawing.

• 48:29Tim Ferriss?

  There we go.

• 48:30Speaker 01

  Charcoal.

• 48:31Tim Ferriss?

  All right. Charcoal, charcoal drawing, naked lady, changing poses every 10 minutes.

• 48:37Speaker 01

  Could be a better way to learn art.

• 48:38Tim Ferriss?

  What a lovely way to learn art.

• 48:40Speaker 01

  Yeah.

• 48:41Tim Ferriss?

  And living the life of a refined gentleman. Pasta and wine and culture and road biking, little cap, maybe.

• 48:50Speaker 01

  Little cap, of course, no helmet, taking Italian classes in the morning.

• 48:55Tim Ferriss?

  Yeah. So here and there, it sounds like a great life.

• 48:58Speaker 01

  It was fun.

• 48:58Tim Ferriss?

  So how the hell does Zillow happen?

• 49:02Speaker 01

  Yeah.

• 49:03Tim Ferriss?

  Do you start getting fidgety? I mean, what, what happens there?

• 49:06Speaker 01

  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. Cause I really didn't need to, I had enough to take care of myself for the rest of my life. But something I discovered, I was still on a few boards, including the IAC board, which had bought X Media and Netflix, where I'd been on the board since like 2000. And still, I'm still on that board and a couple others. So I was still involved in the business world from a kind of long, in a long distance way.

• 49:48Speaker 01

  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 going to stay in Italy. We were going to move back and I was going to 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.

• 50:13Tim Ferriss?

  And you came to the US.

• 50:15Speaker 01

  Came back.

• 50:15Tim Ferriss?

  I am going on a hunting expedition. Did you already have an inkling of what you were going to do?

• 50:20Speaker 01

  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. And 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 Frink, who 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

• 51:04Speaker 01

  for good reason. Awesome guy, really smart.

• 51:07Tim Ferriss?

  I won't follow up on that.

• 51:09Speaker 01

  We don't need to. It's a fun story, 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. He went off on one that was kind of Dropbox before Dropbox. It was like, it was obvious that the kind of cloud storage thing was going to be huge. And I said, go figure that out. See what it's cost. You know, and so he disappeared for a couple of weeks. So we were kind of sharing an office and came back. He's like, yeah, the hundred percent 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.

• 51:46Tim Ferriss?

  Where were you guys brainstorming?

• 51:48Speaker 01

  We were brainstorming in his dad's, his dad was a stockbroker where he had an extra couple of rooms in his office and he just gave them to us.

• 51:53Tim Ferriss?

  New York City?

• 51:54Speaker 01

  No, no, this is Seattle.

• 51:55Tim Ferriss?

  Oh, Seattle.

• 51:56Speaker 01

  Seattle. Yeah. So we're in Seattle. Cause we didn't sell our house in Seattle when we moved it. 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 a basically to create a digital real estate marketplace.

• 52:42Speaker 01

  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 frigging hard. This is 2003 and like 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.

• 53:02Tim Ferriss?

  Making it opaque.

• 53:02Speaker 01

  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 at that, that was the dawn of Zillow. Yeah. 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.

• 53:30Tim Ferriss?

  All this trick in the book.

• 53:33Speaker 01

  So maybe I am a four hour work to pack kind of guy. I said, look, I don't want to do it full time. Like you can use my name. Of course, he was like, yes, sure. Whatever. You can do whatever you want, Rich, knowing I'd be sucked in.

• 53:43Tim Ferriss?

  Let the line out.

• 53:44Speaker 01

  He totally managed me. Yeah, I think I'm in charge now. Lloyd was in charge.

• 53:50Tim Ferriss?

  So when you say you're brainstorming, right? There's an entire universe of possibilities.

• 53:54Speaker 01

  Yeah.

• 53:55Tim Ferriss?

  What constraints or criteria are you applying to that brainstorming? What are you looking for?

• 54:01Speaker 01

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

• 54:35Tim Ferriss?

  At some point.

• 54:36Speaker 01

  At some point.

• 54:36Tim Ferriss?

  In inevitability.

• 54:37Speaker 01

  In inevitability. And business model, who knows?

• 54:41Speaker 01

  Who cares? It's a giant. It's a big pond, you know, and so my business criteria for doing stuff is, is it a big pond? And are there good fishermen?

• 54:51Tim Ferriss?

  Right, because the travel CD-ROM wasn't big enough, right?

• 54:54Speaker 01

  Small pond.

• 54:55Tim Ferriss?

  Hundred million, that's the entire market. Plus, you're not going to carry a briefcase that you're doing weight training with inadvertently.

• 55:04Speaker 01

  Problems.

• 55:05Tim Ferriss?

  To read the thing.

• 55:05Speaker 01

  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, you know, a couple of years ago, talking about the Uber thing, what would be the insight? You were involved there a little bit.

• 55:24Tim Ferriss?

  I was one of the first three advisors when it was called Uber Cab LLC, yeah, way back in the day.

• 55:29Speaker 01

  Yeah.

• 55:30Tim Ferriss?

  And for people who didn't pick up, Dara.

• 55:32Speaker 01

  Yeah, oh, sorry, Dara's the CEO.

• 55:34Tim Ferriss?

  Current CEO of Uber.

• 55:35Speaker 01

  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, kind of, to some, a lot of people looked too small because it was a black car TAM, this total addressable market. But the insight that you and Gurley and Travis and, I guess, J Cal and others had was that actually, no, it was gonna, it was gonna take not just the black car market, but taxi, transportation, and then ultimately more.

• 56:10Tim Ferriss?

  It can expand the total addressable market.

• 56:12Speaker 01

  That's right. Car ownership.

• 56:14Tim Ferriss?

  Yep.

• 56:15Speaker 01

  Just transportation, you know, and of course, obviously, it's beautifully played out that way. Took a little while to see, but it's, you know, 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 what, 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, yeah.

• 56:49Tim Ferriss?

  What were some of the big mistakes and how costly, how risky were they?

• 56:54Speaker 01

  Pretty small venture numbers at that point and Lloyd and I were funding it ourselves. You know, we put the first five million bucks total in with a couple of friends. So costly, but not that costly. But the first idea we were

• 57:06Tim Ferriss?

  Side note also what Garrett Camp did with Uber early on.

• 57:10Speaker 01

  He did too. He wrote, I didn't realize that.

• 57:11Tim Ferriss?

  Yes, there was self-funding for a while. Wasn't expensive. It wasn't overly expensive, but.

• 57:16Speaker 01

  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.

• 57:26Tim Ferriss?

  Yeah.

• 57:26Speaker 01

  You know, I love Gurley. We're really close, but by the time Gurley or the venture capitalists come in, you know, 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. Okay. 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. You know, the digital auction-based marketplace.

• 58:00Tim Ferriss?

  You say it came from another company.

• 58:01Speaker 01

  Yeah.

• 58:01Tim Ferriss?

  I might not know that wrinkle.

• 58:03Speaker 01

  Yeah, it did.

• 58:04Tim Ferriss?

  Meaning they acquired something or they?

• 58:06Speaker 01

  I'm thinking, what's the guy's name who did the startup incubator factory, Gross?

• 58:10Tim Ferriss?

  Oh, Bill Gross?

• 58:11Speaker 01

  Yeah, yeah. It was, I may be getting this wrong.

• 58:14Tim Ferriss?

  Am I making this idea lab?

• 58:15Speaker 01

  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, you know, look it up later maybe.

• 58:26Tim Ferriss?

  In the show notes, yeah.

• 58:26Speaker 01

  And but it was, the whole basis of the search engine was AdWords.

• 58:30Tim Ferriss?

  AdWords. Oh, wow. So did Google acquire that or they just being a better mousetrap?

• 58:36Speaker 01

  Think the latter, but I'm not an expert.

• 58:38Tim Ferriss?

  All right.

• 58:39Speaker 01

  Regardless, I don't want to speak out of term.

• 58:41Tim Ferriss?

  We'll put the story in the, in the show notes.

• 58:42Speaker 01

  Okay, right. It's, there's a good story there, I'm sure. Why I brought it up was we were enamored of auctions. Auctions are, 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. We're going to auction homes.

• 59:10Speaker 01

  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. 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

• 59:55Speaker 01

  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.

• 1:00:35Tim Ferriss?

  And the timing of that is pretty wild, right? And it's just like how things line up. Because I mean, how long had the aerial view been around prior to you guys?

• 1:00:44Speaker 01

  Short.

• 1:00:44Tim Ferriss?

  It was short.

• 1:00:45Speaker 01

  Short. And there was no iPhone, there were no smartphones.

• 1:00:47Tim Ferriss?

  Yeah.

• 1:00:48Speaker 01

  But it was obvious. Like, I was like, whoa. And then I also had in my head, homes are, for home, American homeowners, oftentimes their largest asset, and the bulk of their wealth.

• 1:01:02Speaker 01

  And people care a lot about it.

• 1:01:03Tim Ferriss?

  Yeah.

• 1:01:03Speaker 01

  So I knew they wanted to know the value. I knew that was catnip. Okay, I knew I 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 zestimate, 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.

• 1:01:30Tim Ferriss?

  Okay, so at the time was it just rentable infrastructure, AWS, you get it going, you launch and it's up to the right. Just a nice, smooth rocket launch. Is that what happened?

• 1:01:40Speaker 01

  AWS didn't exist.

• 1:01:42Tim Ferriss?

  I know.

• 1:01:47Speaker 01

  No, dude, man, this was like server in a closet. Yeah, this was server.

• 1:01:54Tim Ferriss?

  You forbade Christmas lights or something like you're like preserving electricity and compute power and all this stuff.

• 1:02:00Speaker 01

  I don't remember that. I don't remember. But David. David Vitale, 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.

• 1:02:13Tim Ferriss?

  Yeah.

• 1:02:13Speaker 01

  Yeah, I believe. I remember our launch blog post with Garrett, who worked for David, like doing the, what's the professor in?

• 1:02:21Tim Ferriss?

  It's Doc from Back to the Future.

• 1:02:25Tim Ferriss?

  Whatever.

• 1:02:26Speaker 01

  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.

• 1:02:35Tim Ferriss?

  It's like the the Oprah of tech at the time.

• 1:02:38Speaker 01

  Yeah, I mean, God, and Walt loved it and Walt published and millions of people came on day one. And of course, the server in the closet tipped over for a while and it was painful. But Amy Batizki, 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, you know, something like that. And she's like, yeah, that's going to be good press.

• 1:03:11Speaker 01

  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, Benchmark and 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." 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

• 1:03:56Speaker 01

  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 on to something.

• 1:04:04Tim Ferriss?

  What are some aspects of that toolkit or the playbook?

• 1:04:08Speaker 01

  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.

• 1:04:41Tim Ferriss?

  Remind me who Amy is?

• 1:04:42Speaker 01

  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, you know, high school boyfriend's house, philanthropist development team that are trying to figure out who's a good target, you know, whatever.

• 1:05:26Tim Ferriss?

  Lots of applications.

• 1:05:28Speaker 01

  Lots of applications, yeah.

• 1:05:29Tim Ferriss?

  I know you had a lot of fans. I think the Arizona Attorney General was a fan.

• 1:05:34Speaker 01

  That's a deep cut. Wow.

• 1:05:38Tim Ferriss?

  No, but this is of interest to me because there is opposition also.

• 1:05:42Speaker 01

  Oh, yeah.

• 1:05:42Tim Ferriss?

  Right. And my god, I mean, 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.

• 1:05:59Speaker 01

  Yep.

• 1:06:00Tim Ferriss?

  And that was just part of the deal.

• 1:06:01Speaker 01

  Yep.

• 1:06:01Tim Ferriss?

  Right. If you want.

• 1:06:02Speaker 01

  And actually, part of the playbook.

• 1:06:03Tim Ferriss?

  Yeah.

• 1:06:04Speaker 01

  Honestly.

• 1:06:05Tim Ferriss?

  All right.

• 1:06:05Speaker 01

  It's the same provocation marketing. It's the exact same thing. It's exactly the same.

• 1:06:08Tim Ferriss?

  Yeah. So what happened with you guys?

• 1:06:09Speaker 01

  Yeah. I mean, you know, we were provocative to some of the industry players who were big lobbyists.

• 1:06:15Tim Ferriss?

  Yeah.

• 1:06:15Speaker 01

  You know, the Taxi Commission, Uber's case.

• 1:06:17Tim Ferriss?

  Yeah.

• 1:06:18Speaker 01

  In our case, a lot of the real estate professional associations.

• 1:06:21Tim Ferriss?

  They were not.

• 1:06:22Speaker 01

  A lot of voters.

• 1:06:22Tim Ferriss?

  They were not, they were not thrilled.

• 1:06:23Speaker 01

  They're not thrilled, or they think they're not thrilled. They don't realize till later that it's could be helpful. But, but whatever. Yes, they were.

• 1:06:31Tim Ferriss?

  Initially.

• 1:06:31Speaker 01

  Provoked. Nobody, no industry that's likes to 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.

• 1:06:43Tim Ferriss?

  You may like change when you're the instigator of the change.

• 1:06:46Speaker 01

  Well, that's, you know, awesome.

• 1:06:50Speaker 01

  It leaves me more open to change coming from the outside too, though. I do believe, I do believe. And I, and I, and I, obviously, this is just human nature.

• 1:06:57Tim Ferriss?

  Yeah.

• 1:06:58Speaker 01

  But, 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're 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.

• 1:07:41Tim Ferriss?

  Yeah.

• 1:07:41Speaker 01

  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.

• 1:07:58Tim Ferriss?

  Yeah. In the case of Uber, I don't want to 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.

• 1:08:09Speaker 01

  No.

• 1:08:10Tim Ferriss?

  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.

• 1:08:28Speaker 01

  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 on to something. And having popular support, as we're learning politically right now, is having big populist support is ultimately where the power is derived. So sometimes you can go too far. We don't need to talk about that. But of course you can go too far. And in fact, it may be that you need to go too far to establish where the frontier is.

• 1:09:02Tim Ferriss?

  All right. Well, I can't, I can't not take the bait on that one. What does going too far look like?

• 1:09:10Speaker 01

  I was thinking specifically Uber, but.

• 1:09:12Tim Ferriss?

  Oh, all right.

• 1:09:13Speaker 01

  Yeah, but, but because it did, you know, in some cities, municipalities or Airbnb.

• 1:09:18Tim Ferriss?

  You can, you can push too hard.

• 1:09:20Speaker 01

  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, you know, this is not a story. I know this guy's a little bit, but it's not a story I'm intimately familiar with, nor was I an early investor or anything. But, you know, they did piss off some homeowners, you know, in certain cities, not just the hotel owners.

• 1:09:46Tim Ferriss?

  Yep.

• 1:09:47Speaker 01

  And, you know, so they found the line and I think they managed it really, really well because they lead from the heart. You know, I think other companies may have not obviously led from a heart and had, had a difficulty. At Zillow, our, our, our job was a little easier.

• 1:10:02Tim Ferriss?

  Also with those battles, I remember there were early on a number of locations that were incredibly important.

• 1:10:10Speaker 01

  Yeah.

• 1:10:10Tim Ferriss?

  Not just from a ride volume perspective, but from a precedent setting perspective.

• 1:10:14Speaker 01

  Yeah.

• 1:10:15Tim Ferriss?

  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.

• 1:10:24Speaker 01

  That's right.

• 1:10:24Tim Ferriss?

  10 locations. Because people have gotten the message, you can be a little more diplomatic about it, which people figure out over time.

• 1:10:31Speaker 01

  But then there's the next country and then whatever. Anyway, there's always something. But provocation marketing with a heart with the end consumers' best interests in mind. That's a winner.

• 1:10:44Tim Ferriss?

  So if you were teaching a class, maybe you already have, I have no idea, related to provocation marketing. All right, there you go. You get to choose. You can go back to your alma mater, wherever it might be. You're teaching a class. What would other elements of the class be? Other resources, principles, anything at all?

• 1:11:03Speaker 01

  Well, I try to figure out a structure here on the fly 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 was my co-founder and the team, they had a data collection problem

• 1:11:48Speaker 01

  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.

• 1:12:13Tim Ferriss?

  That's very clever.

• 1:12:14Speaker 01

  Very clever. And say, 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. You know, and do a company review.

• 1:12:25Tim Ferriss?

  How many people screwed that up where they're the only person at that position? I guess it has.

• 1:12:30Speaker 01

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

• 1:12:46Tim Ferriss?

  Yeah.

• 1:12:47Speaker 01

  And we knew all those things would provoke, we knew some CEOs would go crazy, you know? So there's another example while I'm formulating a framework. The another one is with another former Expedia guy, Mark 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? This was, 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.

• 1:13:29Tim Ferriss?

  Yeah, definitely a great way to kick the hornet's nest.

• 1:13:33Speaker 01

  Some investors, when we were raising money, I remember traveling around, you know, doing the Sand Hill Shuffle with Mark and, you know, I remember some people saying, well, is this legal? You're going to get, can you rate people? You know, you're going to get sued, you know, I'm not going to invest. And we were like, yeah, we're going to get sued. You know, 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.

• 1:14:04Tim Ferriss?

  Yeah.

• 1:14:05Speaker 01

  Okay. 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.

• 1:14:21Speaker 01

  Anyway, that was exactly the launch strategy of AVO. It's like, here come the suits. I'll give you the FBI. Anyway, it was perfect because it created all kinds of noise. I'm struggling with.

• 1:14:31Tim Ferriss?

  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 going to be the best comparison. Like 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 were 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?

• 1:15:00Speaker 01

  Oh, yeah.

• 1:15:00Tim Ferriss?

  If you go stay at the Rosewood

• 1:15:02Speaker 01

  Yep.

• 1:15:02Tim Ferriss?

  and you're right around the corner, that's got its own stories. That's a strange place, but

• 1:15:06Speaker 01

  Fantastic.

• 1:15:07Tim Ferriss?

  Fantastic.

• 1:15:08Speaker 01

  Love that.

• 1:15:10Tim Ferriss?

  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, nah, I'm not going to touch that with a 10 foot pole?

• 1:15:26Speaker 01

  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.

• 1:15:42Tim Ferriss?

  Yeah.

• 1:15:42Speaker 01

  And so

• 1:15:43Tim Ferriss?

  People could still just consume so much energy, right?

• 1:15:46Speaker 01

  No doubt. So we raised money to deal with that, but we knew it was going to 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, you know, after we won the first few suits, you know, they lost steam. The lawyers lost steam on suing. So it caused some venture capitalists to not do it, but the more kind of disruptive oriented folks were like, yeah, great.

• 1:16:11Tim Ferriss?

  So what happened with that?

• 1:16:13Speaker 01

  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 middle, digital middlemen who were kind of SEO on one side, collecting Google search traffic on one side and trying to monetize leads on the other. You know, as time wore on, a lot of those business models got somewhat disintermediated. And so the protection against that is usually to go down into the workflow of the transactions of the, of the industry, which is say what we've done at Zillow or what Expedia does.

• 1:16:47Tim Ferriss?

  So could you explain that?

• 1:16:48Speaker 01

  Yeah.

• 1:16:48Tim Ferriss?

  Just one more time and maybe an example would be helpful. So let's just say there's TripAdvisor for X.

• 1:16:52Speaker 01

  Yep.

• 1:16:53Tim Ferriss?

  Like you said, they're kind of harvesting traffic on the SEO side.

• 1:16:56Speaker 01

  Yep.

• 1:16:56Tim Ferriss?

  So their pages are Engineered in such a way.

• 1:16:59Speaker 01

  That's right.

• 1:16:59Tim Ferriss?

  Maybe also using ad spend.

• 1:17:01Speaker 01

  Yeah.

• 1:17:01Tim Ferriss?

  To drive traffic to these reviews.

• 1:17:04Speaker 01

  Yeah.

• 1:17:04Tim Ferriss?

  Which are then monetized.

• 1:17:06Speaker 01

  Yes.

• 1:17:06Tim Ferriss?

  On some level.

• 1:17:07Speaker 01

  That's right. Some people can see, but by selling those leads out the other side of the marketplace.

• 1:17:12Tim Ferriss?

  Right.

• 1:17:13Speaker 01

  So literally a lead middleman.

• 1:17:14Tim Ferriss?

  You got it. Yeah.

• 1:17:15Speaker 01

  Okay.

• 1:17:16Tim Ferriss?

  So how would they get this intermediated?

• 1:17:18Speaker 01

  Michael Porter, Five Forces would say, look, if you have an over dependency on any supply of customers, you're strategically exposed.

• 1:17:25Tim Ferriss?

  Mm hmm.

• 1:17:26Speaker 01

  For obvious reasons. If you have an over dependency on any supplier.

• 1:17:29Tim Ferriss?

  Yeah.

• 1:17:30Speaker 01

  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.

• 1:17:40Tim Ferriss?

  Yep.

• 1:17:40Speaker 01

  Over you. Okay. Well.

• 1:17:41Tim Ferriss?

  Also, it's like a single point of failure. Right. If.

• 1:17:44Speaker 01

  Absolutely.

• 1:17:44Tim Ferriss?

  Oop, factory went down because of XYZ. That's a problem.

• 1:17:48Speaker 01

  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.

• 1:18:01Tim Ferriss?

  Mm hmm.

• 1:18:02Speaker 01

  Paid or free, you're developing a serious dependency on Google. And Google, of course, in its own search for increased value starts looking vertical, which means down into your business.

• 1:18:14Tim Ferriss?

  Yeah.

• 1:18:14Speaker 01

  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.

• 1:18:38Tim Ferriss?

  Yeah.

• 1:18:39Speaker 01

  Okay. So strategically speaking, my defense against that in my digital marketplaces has been twofold. One, build a giant brand that customers know.

• 1:18:50Tim Ferriss?

  Mm hmm.

• 1:18:50Speaker 01

  And love. And therefore, most of your traffic and customers comes directly to your app insights. Okay. You have to have a brand to do that in order to have power. And then two, look down your funnel and look into the workflow of the business you're in, be it 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.

• 1:19:19Tim Ferriss?

  Mm hmm.

• 1:19:20Speaker 01

  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.

• 1:19:52Tim Ferriss?

  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.

• 1:20:00Speaker 01

  Okay.

• 1:20:01Tim Ferriss?

  How do you name companies?

• 1:20:03Speaker 01

  You saw that live. I played around with blogging like all of 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 post, the site it's on is called hopperanddropper.com, which is a fly fishing term, but which is, nobody's gone to. So I only had 20 visitors, Tim being one.

• 1:20:31Tim Ferriss?

  Lucky 21.

• 1:20:33Speaker 01

  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, airline tickets.com, you know, 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.

• 1:21:17Speaker 01

  And so you're non-distant and non-d 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.

• 1:22:02Speaker 01

  So I was confident in my ability to, my, my team's really, ability to do that. Okay, so now when you're making up a word, what do you do? And I think this is what you're referring to. Okay, so high point Scrabble letters. Do you play Scrabble?

• 1:22:14Tim Ferriss?

  It's been a minute, but yes, I've played Scrabble.

• 1:22:16Speaker 01

  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?

• 1:22:24Tim Ferriss?

  I don't.

• 1:22:24Speaker 01

  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 Z's and X's and some Q's actually too. Uh, rule number two, fewer syllables is better than more. I kind of learned this lesson with Expedia. Expedia was, uh, too many syllables. It's worked out fine.

• 1:23:08Speaker 01

  We've overcome that. The company's overcome that now, but it was, in hindsight, was a lot. I liked it because of rule number three, which is it was evocative of positive things. Speed, expedition. So it said adventure and speed and that all felt good, uh, in that word. But fewer syllables, I think two syllables is the sweet spot. Because I also want it to be a good dog name. So if the word could be a good dog name, you're on to something like you can call for it.

• 1:23:37Tim Ferriss?

  Yeah.

• 1:23:37Speaker 01

  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, right? So just interesting, interesting words.

• 1:24:05Tim Ferriss?

  Yeah.

• 1:24:05Speaker 01

  Anyway, that's my handbook.

• 1:24:07Tim Ferriss?

  Palindromes, like my friend Mike Kim back in the day.

• 1:24:10Speaker 01

  I was struggling to think of one. I couldn't pull one on the fly. Well done.

• 1:24:13Tim Ferriss?

  Taco Cat.

• 1:24:15Speaker 01

  It's a good game. So you're in the game space.

• 1:24:20Speaker 01

  That is a funny game, isn't it? So stupid. It's so fun.

• 1:24:24Tim Ferriss?

  That was so good.

• 1:24:24Speaker 01

  Yeah.

• 1:24:25Tim Ferriss?

  So I'm thinking of double letters. So there are names, Expedia had.

• 1:24:30Speaker 01

  X.

• 1:24:31Tim Ferriss?

  Has an X.

• 1:24:32Speaker 01

  X speed.

• 1:24:33Tim Ferriss?

  Good connotation with pre-existing words or concepts.

• 1:24:36Speaker 01

  Yeah.

• 1:24:37Tim Ferriss?

  Maybe one syllable too long. Then you got Zillow.

• 1:24:40Speaker 01

  Zillow, that's a sweet spot.

• 1:24:41Tim Ferriss?

  Kind of named it. I'm imagining this Labrador Retriever, right?

• 1:24:45Speaker 01

  Yeah. And starts with a Z, like what, how many words start with a Z? That's great. And two double letter LL, soft ending.

• 1:24:52Tim Ferriss?

  Double letter, but I'm not sure because I am not up to speed with my Scrabble, Glass Door.

• 1:24:58Speaker 01

  Glass Door, in the mid, you know, in the middle. It was pretty evocative of having people peer is transparency. Power of the people and transparency is a big thing. And 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.

• 1:25:28Tim Ferriss?

  All right. So if you need more time, I'm not going to forget about it. The provocation marketing.

• 1:25:33Speaker 01

  Okay, okay.

• 1:25:34Tim Ferriss?

  Curriculum.

• 1:25:35Speaker 01

  Yeah.

• 1:25:35Tim Ferriss?

  And it could just be one seminar. It doesn't have to be ongoing, just if that complicates the envisioning process.

• 1:25:43Speaker 01

  Find a seven deadly sin zone, something that is emotionally core to us, okay?

• 1:25:50Speaker 01

  That you know is going to incite an emotional response.

• 1:25:53Tim Ferriss?

  All right.

• 1:25:53Speaker 01

  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. And it doesn't make people feel good to be scared. So if you're building a brand and a service, you want people to be provoked, but feel good.

• 1:26:38Speaker 01

  Or tickled or entertained, you know? And so that is where I would head with the seminar. And then we end up brainstorming about getting people's ideas for that.

• 1:26:48Tim Ferriss?

  Let's touch on briefly, mention Bill Gurley, of course, famous venture capitalist. He's been on the show, brilliant guy, also quite hilarious.

• 1:26:57Speaker 01

  And local.

• 1:26:57Tim Ferriss?

  And local.

• 1:26:58Speaker 01

  Hey, Bill.

• 1:26:59Tim Ferriss?

  Yeah, yeah, he's right down, right, a couple of blocks from where we're sitting right now. You have spent time at Benchmark Capital, which way back in the day, I mentioned this to Bill. When I first moved to Silicon Valley, a book was recommended to me called E-Boys.

• 1:27:12Speaker 01

  Oh, yeah.

• 1:27:13Tim Ferriss?

  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 to read. 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?

• 1:27:54Speaker 01

  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, you know, romantic, kind of, you know, in a weird way, but you know, for business geeks like me and you, maybe romantic. And I also knew that I had a personality that did want to have my fingers in a lot of stuff.

• 1:28:31Tim Ferriss?

  Hmm. You did?

• 1:28:33Speaker 01

  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. You know, they invited me to a bunch of stuff to sit in on stuff. I knew I would be good at that. I knew I liked doing that. And then a condition with Lloyd Frink of doing the Zillow thing and taking the CEO title, I said, look, you know, I'm going to do a bunch of other things too. I'm going to start more companies and I'm going to do the venture capital thing. And he's like, all good. No problem. And so as a way to keep myself stimulated and seeing lots of stuff and get down to the

• 1:29:13Speaker 01

  valley, I was in Seattle, which was not really a venture op-ed at the time. Cloud computing hadn't happened yet. We did have Amazon, Expedia and Microsoft, but you know, and so the action on the cutting edge was down in the valley. I had some boards I was on down there as well. And so I took the venture partner job with Benchmark, which is a pretty ill-defined position as a way to 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, you know, love that team. I love that team to this day.

• 1:29:51Tim Ferriss?

  How did it benefit the other things? Was it just seeing around corners, kind of getting an idea of what's coming before most other people have a chance to?

• 1:29:59Speaker 01

  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.

• 1:30:38Tim Ferriss?

  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?

• 1:30:57Speaker 01

  Okay, what it means to sit on a board is, when a company's 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. Not, don't, you're not running anything, but you're basically coaching the entrepreneurs who oftentimes are less experienced, sometimes not, but oftentimes less experienced. And I would always recommend assembling a board of people with real experience who are going to 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.

• 1:31:40Speaker 01

  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, in a public company, it's a little different.

• 1:31:51Tim Ferriss?

  May I add one thing? And I've never been on a board, but

• 1:31:54Speaker 01

  Really?

• 1:31:55Tim Ferriss?

  Yeah, no, I've dodged it, I guess, in a sense.

• 1:31:57Speaker 01

  So you have a negative impression?

• 1:31:59Tim Ferriss?

  No, no, it's not a negative impression.

• 1:32:01Speaker 01

  You dodged it?

• 1:32:02Tim Ferriss?

  Well, I feel like, dodged is a strong verb to use.

• 1:32:06Speaker 01

  So that was a missile coming at you and you

• 1:32:08Tim Ferriss?

  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.

• 1:32:19Speaker 01

  Yeah.

• 1:32:20Tim Ferriss?

  Which is part of the reason why I'm asking you.

• 1:32:21Speaker 01

  Okay, got it.

• 1:32:21Tim Ferriss?

  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

• 1:32:42Speaker 01

  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.

• 1:32:51Tim Ferriss?

  Yeah.

• 1:32:51Speaker 01

  That's good context.

• 1:32:52Tim Ferriss?

  But it's something that I've been, not necessarily reconsidering, because I've

• 1:32:56Speaker 01

  I think you should. I think you'd be good.

• 1:32:57Tim Ferriss?

  Okay, tell me.

• 1:32:58Speaker 01

  Well, you're a coach.

• 1:32:59Tim Ferriss?

  Yeah.

• 1:33:00Speaker 01

  That's all it is.

• 1:33:01Tim Ferriss?

  Okay.

• 1:33:02Speaker 01

  I mean, it's what, it's what it primarily is. You're instinctively a coach. And you have a lot of experience sets and you look for, look for analogies. You look for, you know, oh, this situation here is a lot like this other situation. And that, that makes you a good communicator. And that is oftentimes what good coaching is.

• 1:33:17Tim Ferriss?

  And I kind of in, I shouldn't say inadvertently, because it's not inadvertent, but informally do that already, right? With a lot of the founders that I'm involved with.

• 1:33:28Speaker 01

  Which is fine too.

• 1:33:29Tim Ferriss?

  Yeah.

• 1:33:30Speaker 01

  But it's that same, in the best of circumstances, it is that same way on a board.

• 1:33:35Tim Ferriss?

  Mm hmm.

• 1:33:36Speaker 01

  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

• 1:33:46Speaker 01

  Oftentimes in a public company, when you get into the public markets where your responsibilities are a little different.

• 1:33:51Tim Ferriss?

  Yep.

• 1:33:52Speaker 01

  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?

• 1:34:01Tim Ferriss?

  Capital allocation, meaning how do they spend their funds?

• 1:34:04Speaker 01

  Raising money, raising money, spending money, usually not to the budgetary, but big, big acquisitions, whatever.

• 1:34:10Tim Ferriss?

  I got it.

• 1:34:11Speaker 01

  Big, big changes in the cap table in the balance sheet that will affect shareholders.

• 1:34:16Tim Ferriss?

  Yep.

• 1:34:16Speaker 01

  Okay.

• 1:34:17Tim Ferriss?

  Got it.

• 1:34:17Speaker 01

  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.

• 1:34:32Tim Ferriss?

  What is that? Oh, wow. Okay, so they're like the lawyers competing to have good ratings on AVO.

• 1:34:39Speaker 01

  Kinda.

• 1:34:39Tim Ferriss?

  Okay.

• 1:34:40Speaker 01

  Kinda. And then when a board-

• 1:34:41Tim Ferriss?

  This is something I haven't heard anything about.

• 1:34:42Speaker 01

  If a board tips-

• 1:34:43Tim Ferriss?

  Oh, this is juicy.

• 1:34:44Speaker 01

  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.

• 1:34:54Tim Ferriss?

  Cover your ass.

• 1:34:55Speaker 01

  Yeah, because you only get sued, whatever. If you don't want to look bad, whatever. Versus, let's build the company.

• 1:35:00Tim Ferriss?

  Yeah, that doesn't have fun.

• 1:35:01Speaker 01

  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?

• 1:35:10Tim Ferriss?

  Yeah.

• 1:35:10Speaker 01

  So I'm on a few public boards, but they're all really their strategy and how can we grow and how can we help you and how's the team doing? And, and so if I don't get a good ISS rating, which I have some of the worst there are out there, really I do.

• 1:35:26Tim Ferriss?

  Wait, who, who actually determines the rating?

• 1:35:28Speaker 01

  I don't really know the process and I don't really give a rip, but some survey, it's a stick up job, these things. They, they-

• 1:35:36Tim Ferriss?

  Stick up job like-

• 1:35:37Speaker 01

  They rate-

• 1:35:38Tim Ferriss?

  They give us what we want or else?

• 1:35:39Speaker 01

  Look, it's like bond ratings or whatever, like these ratings firms, they do ratings and then they sell consulting services to the customers.

• 1:35:47Tim Ferriss?

  Oh, yeah.

• 1:35:48Speaker 01

  It's just a classic, you know? And mutual funds and ETFs, whatever, hire them and, you know, they can't track every company, so they look at the ratings and how we should vote on the proxy issue and blah, blah, blah. Anyway, I've got very low ratings for lots of nonsensical reasons, but I don't care.

• 1:36:05Tim Ferriss?

  Yeah, yeah, yeah.

• 1:36:07Speaker 01

  I personally don't care, but a lot of the board that's full of directors who really do care is like not as, you know, it's not as fun. Framework for you, which you asked, Greg Maffei, who's on my board at Zillow and who I've worked with for a long time, I mentioned already, and Jay Hoed 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?

• 1:36:38Tim Ferriss?

  Yeah.

• 1:36:38Speaker 01

  It's a good place to start.

• 1:36:39Tim Ferriss?

  Those are, those are.

• 1:36:40Speaker 01

  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.

• 1:36:45Tim Ferriss?

  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 was just traveling around.

• 1:36:57Speaker 01

  Right.

• 1:36:57Tim Ferriss?

  A different city every, you know, every other week.

• 1:37:00Speaker 01

  Soul crushing.

• 1:37:01Tim Ferriss?

  Yeah.

• 1:37:01Speaker 01

  It's not quite that way, but, 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.

• 1:37:16Tim Ferriss?

  Right.

• 1:37:17Speaker 01

  As a growth stock, you know, so.

• 1:37:19Tim Ferriss?

  And, and this is as good a point as any to just explain the, I guess, compensation structure. How does it work? You get an equity grant, you have options that vest over time. And then I suppose it depends on the state of the.

• 1:37:30Speaker 01

  That's right.

• 1:37:30Tim Ferriss?

  End stage of the company, but.

• 1:37:33Speaker 01

  Private companies often are not compensated because you're the venture capitalist.

• 1:37:36Tim Ferriss?

  Right.

• 1:37:37Speaker 01

  Okay. So you're the funder. So you're doing it because you've already, you already own a chunk of the company.

• 1:37:42Tim Ferriss?

  Yep.

• 1:37:42Speaker 01

  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, like I'm sure Stripe directors make a lot of money. Public companies, you know, it's really just like salary bands based on the size of the company. I mean, it's like for most 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. You know, so it's nice. And then usually they enable the directors to choose if they wanted, 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.

• 1:38:27Tim Ferriss?

  All right, so. Fun, local, lucrative.

• 1:38:31Speaker 01

  Potentially lucrative.

• 1:38:32Tim Ferriss?

  Potentially.

• 1:38:32Speaker 01

  And fun, 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.

• 1:38:39Tim Ferriss?

  Mm hmm.

• 1:38:40Speaker 01

  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 this, these guys want that and these ones want that. And like, you know, run away.

• 1:38:56Tim Ferriss?

  Less game of Thrones.

• 1:38:57Speaker 01

  Yeah. No fun. No fun.

• 1:39:01Tim Ferriss?

  All right, so we're drinking our carbonated Japanese citrus. Yes.

• 1:39:06Speaker 01

  Yuzu coconut water.

• 1:39:07Tim Ferriss?

  Feeling, feeling very.

• 1:39:09Speaker 01

  Infused.

• 1:39:10Tim Ferriss?

  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. And then I started paying attention to things I had neglected before that. And da, da, da, da, including health.

• 1:39:29Speaker 01

  Yeah.

• 1:39:29Tim Ferriss?

  And body, things like that. So when did that happen? Was, was it a gradual development of wellness habits, self-care? Or was there a reckoning at some point? What happened?

• 1:39:44Speaker 01

  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, you know, and maybe an overlay of general age. You know, the substrate is age. And ultimately, everybody probably figures this out. Some later, sooner than others.

• 1:40:05Tim Ferriss?

  What is your age now? I have no idea. I can't tell.

• 1:40:07Speaker 01

  Fifty seven.

• 1:40:08Tim Ferriss?

  Okay, God.

• 1:40:09Speaker 01

  Yeah.

• 1:40:09Tim Ferriss?

  Wow.

• 1:40:09Speaker 01

  Yeah.

• 1:40:10Tim Ferriss?

  Really held on to the.

• 1:40:11Speaker 01

  Yeah, right.

• 1:40:11Tim Ferriss?

  Useful.

• 1:40:12Speaker 01

  Yeah, right.

• 1:40:13Tim Ferriss?

  Glow.

• 1:40:13Speaker 01

  Everything's falling apart.

• 1:40:14Tim Ferriss?

  Look at me, oh my God. American history acts as 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.

• 1:40:26Speaker 01

  I am, and it was 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. And 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 aged maybe 35, 34, running Expedia.

• 1:40:58Speaker 01

  As a really young public company CEO, the company's doing great, but I like had to deal with stuff like nine 11, you know, during the, in the travel business. And I had been a pretty like, 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. Like we all kind of, 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.

• 1:41:40Speaker 01

  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 like, 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 like partially dilated and like just some small contractions. And Sarah thought nothing of it.

• 1:42:25Speaker 01

  You know, the shoemakers kids have no shoes. Sarah's like, oh, fine. I'll just keep the seat reclined as we drive up to Whistler and her, her doctor Edie, Edith said, not only you not going up to whistle, you're not going home. You are going to be admitted to the hospital and we're going to 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.

• 1:42:56Speaker 01

  Then everything turned out great. She carried them to thirty-five weeks or something, thirty-six weeks. Kids are perfect. The birth was a little hard. The kids were perfect. And it all worked out. But in the course of that period of time, it got me to reassess my life and how I live my life and what my priorities were and how I, you know, 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 going to 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.

• 1:43:39Tim Ferriss?

  Need 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 twelve new things I'm starting. Did you layer it in? And would you have done anything differently?

• 1:43:56Speaker 01

  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. Like, 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, you know, I remember the first real class, the kind of thing I'd ever done was hot yoga. And I was like, wow, this is amazing. I feel incredible after I come out of that class and it's, you know, 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, I hadn't, didn't hire

• 1:44:39Speaker 01

  a trainer until much later, but I eventually, I eventually got there. I didn't lift weights for a long, long time. I was more just kind of running. I took up running. I ran a couple of marathons. You know, I discovered my body was not built for, my joints were not built for marathons. Anyway, I did, 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 like, The physiology of what's happening to my body and my bone density, my muscle mass at my age, it's like I'm like continually been ramping up how much I do.

• 1:45:20Speaker 01

  A because it makes me feel good, but B because I'm, you know, just age wise deteriorating. And if I want to snowboard, I've snowboarded 35 days this year and it's been amazing. And like, if I want to keep doing stuff like that, I've got to be strong.

• 1:45:35Tim Ferriss?

  So what does the current regimen look like? Generally speaking, I'm sure there are exceptions and maybe you've traveled or go to various places. But what does the general regimen look like?

• 1:45:45Speaker 01

  Probably a couple hours total of zone two-y type stuff, you know, bike, rowing, maybe tread. My knees kind of are not great running, but the treadmill, a softer treadmill works. But the Peloton is my favorite one there. And then weightlifting, 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

• 1:46:11Tim Ferriss?

  I got sports.

• 1:46:11Speaker 01

  Play sports.

• 1:46:12Tim Ferriss?

  Yeah.

• 1:46:13Speaker 01

  I play tennis. I like to do a lot of stuff with my body and the world. Yeah.

• 1:46:18Tim Ferriss?

  How do you fit that in? I mean, you got a lot going on. You like building, you continually, as our mutual friend Chris Saka has in one of his, one of his suggested topics for exploration, since I asked him, like you continually put yourself back in the arena.

• 1:46:33Speaker 01

  Yeah.

• 1:46:33Tim Ferriss?

  Right? As a builder.

• 1:46:35Speaker 01

  Yeah.

• 1:46:35Tim Ferriss?

  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?

• 1:46:48Speaker 01

  For me now, priority wise, that is, I mean, 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'm not operating. I, but seven, eight months ago, I, 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 management type leader,

• 1:47:30Speaker 01

  I encourage them to really take a vacation and disappear. And most people think that's going to be harmful to their business or their career. And what I try to coach them on is no, that is actually the way you develop your leaders. One of the ways you develop your leaders, because if you're really disconnected, you're on a surf trip in Indonesia and you have zero connectivity.

• 1:47:52Tim Ferriss?

  For how long?

• 1:47:53Speaker 01

  For two weeks, okay? Do it for two weeks and be disconnected. And your teams are gonna have to figure out how to deal with stuff that's important.

• 1:48:02Tim Ferriss?

  And they're gonna have to create systems and policies and rules ahead of time that will outlive the surf trip.

• 1:48:09Speaker 01

  That's true, but from a leadership perspective, sometimes the real leader of an organization is not necessarily the one with the title.

• 1:48:17Tim Ferriss?

  Yeah.

• 1:48:17Speaker 01

  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?

• 1:48:44Tim Ferriss?

  Mm-hmm.

• 1:48:44Speaker 01

  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.

• 1:49:03Tim Ferriss?

  Yeah.

• 1:49:04Speaker 01

  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.

• 1:49:22Speaker 01

  Everybody always thinks you're working on the other thing. I'm being glib and it's kind of gets, it gets a little bit of a chuckle, but it's, I am a seriously leverage oriented person. So it's not that hard.

• 1:49:33Tim Ferriss?

  Yeah. What are other ways that you identify opportunities for leverage or think about leverage?

• 1:49:42Speaker 01

  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. Like Sarah is amazingly smart and capable and cares and like the stuff that she's in charge of is gonna happen well. You know, that like, that's an unbelievable feature to have in a partner as you're looking for a partner.

• 1:50:09Tim Ferriss?

  Yeah.

• 1:50:09Speaker 01

  You know, lots of stuff matters in finding a partner, but like, it's really a partnership. If you guys are gonna have a baby, that's a business of sorts. You know, I think it's mostly about picking the right people.

• 1:50:22Tim Ferriss?

  Any recommendations for people who are

• 1:50:28Tim Ferriss?

  hiring folks they have not known for a long period of time? Any recommendations for the hiring process? Cause a lot of people interview well, who don't necessarily perform well. They know what to say.

• 1:50:40Speaker 01

  And reference checks often are conflicted.

• 1:50:44Tim Ferriss?

  I've had the worst luck with taking reference checks at face value. There's some ways to kind of work with that.

• 1:50:50Speaker 01

  Yeah. Two things I would say. One is my favorite, 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, cause if they put it there, that is what they're interested in. And they'd better be able to light up on it. When I was earlier in my career, I would always make up business cases around some interest.

• 1:51:31Speaker 01

  You know, how big is the ski industry? Because you put skiing, whatever, you know, 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.

• 1:51:48Tim Ferriss?

  Firing someone.

• 1:51:49Speaker 01

  Yep.

• 1:51:49Tim Ferriss?

  Okay.

• 1:51:50Speaker 01

  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.

• 1:52:05Tim Ferriss?

  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 or she is going to have to fire someone.

• 1:52:25Speaker 01

  Yeah.

• 1:52:25Tim Ferriss?

  And they're like, hey, boss, I don't want to bother you, but this is something I haven't done before.

• 1:52:31Speaker 01

  Yeah.

• 1:52:31Tim Ferriss?

  Give me some advice.

• 1:52:32Speaker 01

  Yeah, don't do it via text. Be an upstanding person, you know, have some courage. You gotta be face to face, but it's actually not that hard. My advice would be, 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. 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 align, get the interests aligned, which it almost always is, it's not as hard.

• 1:53:18Speaker 01

  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.

• 1:53:32Tim Ferriss?

  And then in terms of the delivery, the conversation, any tips on how to manage that?

• 1:53:38Speaker 01

  You do have to be ready for a lot of stuff to come up. And as the person in the power, holding the 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? You know? And soliciting information on the way out for yourself and the organization is often appreciated and often revealing too. So that's good.

• 1:54:19Tim Ferriss?

  Exit interview.

• 1:54:20Speaker 01

  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.

• 1:54:40Tim Ferriss?

  So, random question, I don't know, you could be covered in tattoos, but what is the story of this tattoo?

• 1:54:47Speaker 01

  Family.

• 1:54:48Tim Ferriss?

  All right.

• 1:54:49Speaker 01

  Five of us in the family, things we love.

• 1:54:52Tim Ferriss?

  So it looks at a quick glance, looks like a snowflake, but those are trees?

• 1:54:57Speaker 01

  It's made up of five trees. It's a snowflake in total shape and it's a starfish in the negative space.

• 1:55:05Speaker 01

  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, sorry, like, sure.

• 1:55:24Speaker 01

  And she's like, and then bought it to me and I was like, okay, let's design one as a family.

• 1:55:28Tim Ferriss?

  Yeah, no wily coyote.

• 1:55:30Speaker 01

  The first, first versions, you know those on the back of a minivan, the family of five with the stick figure mom? That was what Josie drew.

• 1:55:39Tim Ferriss?

  V1.

• 1:55:39Speaker 01

  That's, Josie's very creative. You're, you're creative, honey. But it was funny. That was the first version and we, you know, we were sharing different versions and iterating. And at some point Sarah said, maybe we should bring, you know, this artist friend, Joe Park, into this. And he'd never designed a tattoo. We brought him and he was super psyched to do it. So then he led the creative iterations and we ended up, we ended up with this. They, they look exactly the same, but they're not, they're all unique. They form a Cohesive.

• 1:56:08Tim Ferriss?

  Oh, the trees you're saying.

• 1:56:08Speaker 01

  The trees are unique, too.

• 1:56:10Tim Ferriss?

  Mm hmm.

• 1:56:10Speaker 01

  So, anyway.

• 1:56:11Tim Ferriss?

  I dig it.

• 1:56:12Speaker 01

  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. You know, I think tattoos are, you don't have any? Do you have some?

• 1:56:32Tim Ferriss?

  I don't.

• 1:56:33Speaker 01

  It's a, it's a, very few people have one.

• 1:56:36Tim Ferriss?

  Yeah, I have been, I've been considering getting my first, which is, is in some ways kind of similar. It'd actually be in very similar location, right here with my dog's paw prints. It's hard for me to imagine regretting that.

• 1:56:51Speaker 01

  You won't.

• 1:56:51Tim Ferriss?

  Yeah, I don't think I will.

• 1:56:53Speaker 01

  Yeah.

• 1:56:53Tim Ferriss?

  Yeah.

• 1:56:53Speaker 01

  Yeah.

• 1:56:54Tim Ferriss?

  Uh, so.

• 1:56:55Speaker 01

  We, uh, interestingly, our older boy, Will, was of age to get a tattoo. He was eighteen, I think, at the time, maybe nineteen. But the twins, it wasn't legal to get one in Washington State or most states. And so Josie was actually going to high school for a year in Spain at the time, and Spain didn't have that restriction. So she got the design and got it, got it in Spain. And we have the house in Montana, and Montana doesn't have any restrictions. So on the way to go skiing one time, Russell, you know, went to some sketchy place in Bozeman and got the tattoo. So we got them all, we all got them in different places. It's funny.

• 1:57:29Tim Ferriss?

  Any other, uh, 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?

• 1:57:58Speaker 01

  For the planning on, the kind of constant delayers, which there are a lot of, you know, maybe some right here.

• 1:58:07Speaker 01

  There are a lot of out there.

• 1:58:08Tim Ferriss?

  Yeah.

• 1:58:08Speaker 01

  Okay. And I think the fundamental logic is, this is an important thing and I don't have enough time.

• 1:58:15Tim Ferriss?

  Yeah.

• 1:58:15Speaker 01

  Right now. And so I'll wait till it's a better time.

• 1:58:18Tim Ferriss?

  Mm hmm. There's never a better time.

• 1:58:23Speaker 01

  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.

• 1:58:33Tim Ferriss?

  Yeah.

• 1:58:35Speaker 01

  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 a kind of, as we get older, our ego focus naturally,

• 1:59:18Speaker 01

  the diameter of our ego sphere 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. You know, I think that's a positive. So anyway, I encourage it.

• 1:59:34Tim Ferriss?

  Yeah, for me, it's not a bad timing, looking for better timing thing. It's more of a navigating the bizarre aspects of modern dating, being in my public slash semi-public position and as someone who's already, for a lot of good reasons, slow to trust, getting to a point where I feel like I can pull the trigger. I think that's solvable, but it's, it's not trivial.

• 2:00:01Speaker 01

  It's, I didn't have, I never had to deal with that, but I totally.

• 2:00:04Tim Ferriss?

  How, how old were you guys when you met?

• 2:00:07Speaker 01

  Twenty-two.

• 2:00:07Tim Ferriss?

  Wow. Yeah.

• 2:00:09Speaker 01

  In a pub in Cambridge, Mass.

• 2:00:12Tim Ferriss?

  Look at that. Maybe that's my next move.

• 2:00:14Speaker 01

  No.

• 2:00:15Tim Ferriss?

  Pub crawling Cambridge.

• 2:00:16Speaker 01

  It's hard though. I totally get what you're, get what you're saying. It's hard. For the people with young kids, like, 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. Cause a lot of people out there are not doing that. And eventually it comes home to roost one way or another, you know? 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 jobs.

• 2:00:59Speaker 01

  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, you know, 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.

• 2:01:39Tim Ferriss?

  Yeah.

• 2:01:40Speaker 01

  And super helpful.

• 2:01:42Tim Ferriss?

  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.

• 2:02:27Speaker 01

  Yeah. But we can generalize and say it's been great for moms, but it's more than just moms. Like, you know, but it has enabled really smart, very experienced moms who may have historically decided to take the off-ramp into primarily momhood rather than primarily

• 2:02:46Speaker 01

  Climbing the corporate ladder or just executive leadership path, it's enabled them to come back.

• 2:02:50Tim Ferriss?

  Yeah.

• 2:02:51Speaker 01

  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, you know, as long as like that doesn't make the CEO get angry. Because that's not the way I did it when I came up and look how great I turned out. You know, like I've got to do it this way. It's like, I kind of chuckle when I listen to all that. I'm like, you people like open your minds. Like this is just, this opens doors, this doesn't close doors.

• 2:03:23Tim Ferriss?

  Yeah. So let me ask a couple of quick questions.

• 2:03:25Speaker 01

  Yes.

• 2:03:26Tim Ferriss?

  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?

• 2:03:40Speaker 01

  I am not your typical person probably sitting in this seat and that maybe I am not a nonfiction business book. Sorry, Tim.

• 2:03:52Tim Ferriss?

  Oh, it's okay.

• 2:03:53Speaker 01

  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. But I am fully a, I'm a big reader and it's fiction. And generally good fiction, although I do have, you know.

• 2:04:09Tim Ferriss?

  Cheap thrills.

• 2:04:10Speaker 01

  Yeah, yeah, I do. I do. I really love beautiful, beautiful fiction. I dabble, I've always dabbled in the kind of science fiction, magical realism stuff as well. I believe for me at least, escape from the cranked up, quick twitch, always on alert, operational stuff that business people go with.

• 2:04:33Tim Ferriss?

  Problem solving.

• 2:04:33Speaker 01

  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 Halpern?

• 2:04:54Tim Ferriss?

  Oh, no.

• 2:04:55Speaker 01

  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 Freddy and Frederica. I don't know if you've heard of any of these books.

• 2:05:13Tim Ferriss?

  No.

• 2:05:14Speaker 01

  There's a little bit of magic in him. 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

• 2:05:54Speaker 01

  East. And he's kind of a war guy. He's a vet and he's a pretty engaged political kind of, I call him an offensive realist in the John Mearsheimer mold, kind of hawkish, would be perceived as hawkish, you know, believes in strong defense.

• 2:06:09Tim Ferriss?

  The protagonist.

• 2:06:10Speaker 01

  This is the author.

• 2:06:12Tim Ferriss?

  I got it.

• 2:06:13Speaker 01

  Mark Alpern. 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.

• 2:06:24Tim Ferriss?

  So you, if...

• 2:06:27Speaker 01

  I recommend. Oceans and Stars is great.

• 2:06:28Tim Ferriss?

  Oceans and Stars.

• 2:06:29Speaker 01

  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.

• 2:06:42Tim Ferriss?

  I might dig it. I read Last of the Mohicans just to take a walk through that area and that time period.

• 2:06:48Speaker 01

  Authors I like. I like Haruki Murakami.

• 2:06:51Tim Ferriss?

  Yeah.

• 2:06:52Speaker 01

  Kind of magic. Neal Stephenson is like... Some people don't like his latest book, Polostom. I don't know, he's the one who wrote Snow Crash.

• 2:07:00Tim Ferriss?

  Oh, yeah.

• 2:07:00Speaker 01

  Okay, so you know him. Snow Crash.

• 2:07:02Tim Ferriss?

  I had pizza with him in Seattle 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.

• 2:07:14Speaker 01

  And he's got the beard.

• 2:07:15Tim Ferriss?

  Oh, amazing beard, yeah.

• 2:07:17Speaker 01

  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.

• 2:07:24Tim Ferriss?

  Yeah, he's right there.

• 2:07:25Speaker 01

  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.

• 2:07:36Tim Ferriss?

  Okay, I haven't read it yet.

• 2:07:37Speaker 01

  Some people are giving me grief for it. It's, you know, authors, when they get successful.

• 2:07:43Tim Ferriss?

  Seven thousand pages?

• 2:07:44Speaker 01

  Well, it's long. A lot of his stuff is long, but it's not that long. It's not like Kryptonomicon or something.

• 2:07:49Tim Ferriss?

  Which I loved.

• 2:07:50Speaker 01

  Which me too, me too. But authors, as they get successful, sometimes, you know, they have too much power over their editors. And so they get a little self-indulgent, you know, 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.

• 2:08:12Tim Ferriss?

  Then it rips.

• 2:08:12Speaker 01

  Then it rips. Yeah. So anyway, I highly recommend. And it's going to be a trilogy. And so it's only the first one. So I'm like, you know, I can't wait. Anyway, I love, you can tell I love to, I love to read fiction.

• 2:08:23Tim Ferriss?

  And do you lean these days, if you're gifting, do you have you gifted those books that you mentioned?

• 2:08:30Speaker 01

  I've 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.

• 2:08:36Tim Ferriss?

  Yeah, it is.

• 2:08:37Speaker 01

  It's more, you know, group chat, you know, book group, group chat. That's how most of the book discovery happens for me now.

• 2:08:44Tim Ferriss?

  Have you read any of Ted Chiang's stuff?

• 2:08:48Speaker 01

  Uh-uh.

• 2:08:48Tim Ferriss?

  Oh, man.

• 2:08:49Speaker 01

  Who is it?

• 2:08:49Tim Ferriss?

  Okay, so Ted C-H-I-A-N-G.

• 2:08:53Speaker 01

  Okay.

• 2:08:55Tim Ferriss?

  He has, last I checked, he has two collections of short stories. There is one, which I always script the title of.

• 2:09:04Tim Ferriss?

  It's like stories of your life and other stories, something like that.

• 2:09:09Speaker 01

  Okay.

• 2:09:10Tim Ferriss?

  And one of those short stories was the basis for the movie Arrival with

• 2:09:15Speaker 01

  Oh, God, that's great.

• 2:09:16Tim Ferriss?

  Jeremy Renner, amazing movie. So one of his short stories was the basis for that. And then I read that collection and pretty much everyone 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 clowned here, you know, it's 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. Like, there's just no way, right? Like, that first one was Appetite for Destruction. Like, yeah, you can't do that twice. And the second was just unbelievably good.

• 2:09:50Speaker 01

  All right.

• 2:09:51Tim Ferriss?

  And not all of them will hit necessarily, but the ones that hit are just incredible. And he has

• 2:09:58Speaker 01

  And they're like one night read short story, this collection of one night reads.

• 2:10:00Tim Ferriss?

  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 Mullen, like blends or alternates, in a sense, between sci fi and fantasy in this really compelling way.

• 2:10:22Speaker 01

  Cool.

• 2:10:22Tim Ferriss?

  So you get these like little ginger snacks in between your pieces of sushi.

• 2:10:27Speaker 01

  That sounds, that sounds right up my alley.

• 2:10:29Tim Ferriss?

  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 Awards. It's just like, oh, come on.

• 2:10:46Speaker 01

  Amazing.

• 2:10:47Tim Ferriss?

  Yeah.

• 2:10:47Speaker 01

  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 Tolles, do you know him?

• 2:10:58Tim Ferriss?

  Oh, so good. I've only read.

• 2:11:00Speaker 01

  He was a banker.

• 2:11:01Tim Ferriss?

  I know. Finance. That's, well, that's another one.

• 2:11:03Speaker 01

  Until he was like 40.

• 2:11:05Tim Ferriss?

  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 Howie 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.

• 2:11:27Speaker 01

  I know.

• 2:11:27Tim Ferriss?

  You gotta be kidding me.

• 2:11:28Speaker 01

  I learned that he was on somebody's pod. He gave a great pod when Lincoln Highway came out.

• 2:11:33Tim Ferriss?

  Yeah.

• 2:11:34Speaker 01

  To somebody who cracks open artists. It might have been like Brian.

• 2:11:37Tim Ferriss?

  Oh, compliment.

• 2:11:38Speaker 01

  It might have been compliment.

• 2:11:39Tim Ferriss?

  Yeah, very well.

• 2:11:39Speaker 01

  Who, who, who like gets to artists, right?

• 2:11:42Tim Ferriss?

  Yes, who, by the way, for people who don't know, a quick bit of trivia. So Brian Koppelman, 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 and R days.

• 2:11:59Speaker 01

  Really?

• 2:11:59Tim Ferriss?

  Yeah. Isn't that wild?

• 2:12:02Speaker 01

  He's a talent.

• 2:12:02Tim Ferriss?

  Yeah, so it wouldn't surprise me if Aymar was on that show.

• 2:12:06Speaker 01

  He was on there and I, 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.

• 2:12:15Tim Ferriss?

  Yeah.

• 2:12:16Speaker 01

  You know?

• 2:12:16Tim Ferriss?

  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.

• 2:12:31Speaker 01

  You asked this, so I did think about it a little bit. And my initial response that I latched on to came from that movie Bowfinger. I don't know if you ever saw Bowfinger. It's a cult classic and a lot of you people out there haven't seen it, but I highly recommend it. It's Eddie Murphy tour de force. And Steve Martin and Heather Graham. It's super quirky. Eddie Murphy plays two roles in it, which he did for a while in, in last 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.

• 2:13:14Speaker 01

  And he gets super, he's already a paranoid guy, but he gets super paranoid. He's like, people are following me. And he goes to a thing that I don't know what kind of culty LA religion it's representing, but it's called Mindhead. And he goes in, he has his first counseling with the high priest of Minehead. And the religion is based on three happy premises. I'm not gonna remember them all, but, but happy premise number one was something like, "There is no giant foot in the sky about to step on me." Okay, this is like a mantra you have to repeat. The third one is my favorite, and that was what I was gonna 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.

• 2:13:59Speaker 01

  That, or my favorite Burning Man bar ever, was, had a giant neon sign on top of this kinda 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."

• 2:14:20Tim Ferriss?

  Well, say more.

• 2:14:22Speaker 01

  That's it, "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, high beta, high swings, high mood swings. People have a tendency to, towards fear and panic. And almost always, it's gonna be just fine. And when it's not, it doesn't matter anyway.

• 2:14:45Tim Ferriss?

  Right.

• 2:14:46Speaker 01

  Okay?

• 2:14:46Tim Ferriss?

  Yeah.

• 2:14:47Speaker 01

  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.

• 2:15:04Tim Ferriss?

  Even though I feel like I might ignite, I probably won't. Is that basically related to the "Don't panic"?

• 2:15:09Speaker 01

  Yes, I think so. I think that led me to the "Don't panic." I think so. And I'm not saying I actually, I don't move through the world feeling as if I might ignite. I really don't. But I think a lot of people, especially in the modern news feed, iPhone, TikTok.

• 2:15:24Speaker 01

  Twitter world do feel that way.

• 2:15:26Tim Ferriss?

  Yeah.

• 2:15:26Speaker 01

  And so it's even more important. 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 going to be on the rise. Those are growth businesses, right? It's people sheltering from the digital storm.

• 2:15:57Tim Ferriss?

  Storm of doom.

• 2:15:58Speaker 01

  Exactly. It's so unhealthy, you know?

• 2:16:02Tim Ferriss?

  Have you taken any sabbaticals since Italy?

• 2:16:04Speaker 01

  Oh, yeah. I mean, I I've had multiple retirements and.

• 2:16:08Tim Ferriss?

  Now, are those failed retirements? Or did those have an endpoint where you're like, I'm going to take a year and then I'm going to dust off my gloves?

• 2:16:14Speaker 01

  The Italy one was a failed one, although I suspected I was really young, right? The others, no, it's just been sabbaticals.

• 2:16:21Tim Ferriss?

  How long are they typically?

• 2:16:23Speaker 01

  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 is not always achievable, especially now. Starlink and traveling Starlink and Starlink at my surf camp and Starlink on my airstream. Like, 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 rafted the Grand Canyon this year with a big group of friends and family.

• 2:17:01Speaker 01

  And when you watch the younger people, it's very unsettling for the first, it's 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. 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.

• 2:17:33Tim Ferriss?

  Oh, no, you didn't.

• 2:17:35Speaker 01

  But you can't not be happy when you're doing that and not looking at your phone.

• 2:17:39Tim Ferriss?

  Yeah.

• 2:17:40Speaker 01

  Highly encourage.

• 2:17:41Tim Ferriss?

  Rich.

• 2:17:42Speaker 01

  Tim.

• 2:17:42Tim Ferriss?

  So nice to see you, man.

• 2:17:43Speaker 01

  It's great to see you.

• 2:17:44Tim Ferriss?

  We've covered a lot of ground.

• 2:17:46Speaker 01

  It was fun. Wow.

• 2:17:47Tim Ferriss?

  Where, if people want to learn more things about Rich, should they be visitor 22 to your blog?

• 2:17:54Speaker 01

  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 want to be one of those kind of jerk offs, you know?

• 2:18:19Tim Ferriss?

  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

• 2:18:28Speaker 01

  Yeah.

• 2:18:28Tim Ferriss?

  Train for a bit, just to play with it.

• 2:18:30Speaker 01

  I'm doing more creative things deliberately now and it feels good.

• 2:18:33Tim Ferriss?

  Yeah.

• 2:18:34Speaker 01

  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 should, like I'd be at a party and I'll, I'll show people what I painted.

• 2:18:48Tim Ferriss?

  Yeah.

• 2:18:48Speaker 01

  And it's not good, but it makes me feel good.

• 2:18:51Tim Ferriss?

  I did exactly the same thing during COVID, Procreate, and you go through these tutorials. There's something very soothing about it.

• 2:18:57Speaker 01

  That Australian gal.

• 2:18:58Tim Ferriss?

  Yeah.

• 2:18:59Speaker 01

  Oh, who I think works at Procreate. Who gives the tutorials. So awesome.

• 2:19:03Tim Ferriss?

  Yeah, so many good ones. Is there anything you would like to say? Any closing comments, formal? Public complaints you'd like to lodge?

• 2:19:14Speaker 01

  No, no, I guess I should just, I should thank you. You perform a good service. You provide a good service for a lot of people with this blog and with your books. You know, and certain people need it more than others. And I don't think, I really don't think people are looking for shortcuts. That may have been where you started a little bit.

• 2:19:30Tim Ferriss?

  Yeah.

• 2:19:31Speaker 01

  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.

• 2:19:51Tim Ferriss?

  Thanks, man.

• 2:19:51Speaker 01

  It's great to be here.

• 2:19:52Tim Ferriss?

  Yeah. Awesome to have you. Everybody listening, we're going to include everything we talked about in the show notes, tim.blog/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,

• 2:20:33Tim Ferriss?

  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, gadgets, gizmos, all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcast guests. And these strange esoteric things end up in my field, and then I test them, and then I share them with you. So if that sounds fun, again, it's very short, a little tiny bite of goodness before you head off for the weekend, something to think about. If you'd like to try it out, just go

• 2:21:13Tim Ferriss?

  to tim.blog/friday, type that into your browser, tim.blog/friday, drop in your email, and you'll get the very next one. Thanks for listening. Listeners have heard me talk about making before you manage for years. All that means to me is that when I wake up, I block out three to four hours to do the most important things that are generative, creative, podcasting, writing, et cetera, before I get to the email and the admin stuff and the reactive stuff and everyone else's agenda for my time. For me, let's just say I'm a writer and entrepreneur. I need to focus on the making to be happy. If I get sucked into all the little bits and pieces that are constantly churning, I end up feeling stressed out.

• 2:21:55Tim Ferriss?

  And that is why today's sponsor is so interesting. It's been one of the greatest energetic unlocks in the last few years. So here we go. I need to find people who are great at managing, and that is where Crescent Family Office comes in. You spell it C-R-E-S-S-E-T. Crescent Family Office. I was introduced to them by one of the top CPG investors in the world. Crescent is a prestigious family office for CEOs, founders, and entrepreneurs. They handle the complex financial planning, uncertain tax strategies, timely exit planning, bill pay, wires, all the dozens of other parts of wealth management, just financial management that would otherwise pull me away from doing what I love most: baking things,

• 2:22:38Tim Ferriss?

  mastering skills, spending time with the people I care about. And over many years, I was getting pulled away from that stuff, at least a few days a week, and I've completely eliminated that. So, experience the freedom of focusing on what matters to you with the support of a top wealth management team. You can schedule a call today at cressetcapital.com/tim. That's spelled C-R-E-S-S-E-T. cressetcapital.com/tim to see how Crescent can help streamline your financial plans and grow your wealth. That's cressetcapital.com/tim. And disclosure, I am a client of Crescent. There are no material conflicts other than this paid testimonial. And of course, all investing involves risk, including loss of principal. So, do your due diligence.

• 2:23:22Tim Ferriss?

  My first book, The Four Hour Work Week, 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, blah, blah, blah, then you want to get rid of as much as possible, eliminate. But sometimes, there are things that are a huge hassle, like expense management for a lot of companies, which you can't get rid of. They are essential to your business. But today, thank God, you can automate it. And there is no better way to do that than with today's sponsor, Ramp. Ramp is a free corporate card that automates away your entire expense process. They are incredibly fast-growing and incredibly well-reviewed for good reasons.

• 2:24:06Tim Ferriss?

  The moment your team makes a purchase, Ramp handles everything. Receipt matching, categorization, approval, the whole works. Switching to Ramp is like hiring a full-time employee just for expense management. And Ramp makes it easy to migrate from your current corporate card with their complimentary white-glove onboarding service for new members. More than 25,000 businesses trust Ramp, including my good friends at Shopify and the Boys and Girls Club of America, which is why they were just named number one in spend management by G2. And now, for a limited time, you guys, listeners of The Tim Ferriss Show, can get $250 when you join Ramp. Just go to ramp.com/tim. That's R-A-M-P dot com slash tim.

• 2:24:51Tim Ferriss?

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