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Tim FerrissTim Ferriss

How Rich Barton Built Expedia and Zillow — Audacious Goals, Provocation Marketing, and More

Rich Barton is the co-founder and co-executive chairman of Zillow, a company transforming how people buy, sell, rent, and finance homes. Before Zillow, Rich founded Expedia within Microsoft in 1994 and successfully spun the company off as a public company in 1999. He served as president, CEO, and board director of Expedia and later co-founded and served as non-executive chairman of Glassdoor. This episode is brought to you by: Ramp easy-to-use corporate cards, bill payments, accounting, and more: https://ramp.com/tim (Get $250 when you join Ramp) Cresset prestigious family office for CEOs, founders, and entrepreneurs: https://cressetcapital.com/tim (book a call today) Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business: https://shopify.com/tim (one-dollar-per-month trial period) Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 900 million downloads and been selected for “Best of Apple Podcasts” three years running. Sign up for "5-Bullet Friday" (Tim's free weekly email newsletter): https://go.tim.blog/5-bullet-friday-yt/ Follow the Tim Ferriss Podcast: https://tim.blog/podcast/ Visit the Tim Ferriss Blog: https://tim.blog/ Follow Tim Ferriss on Twitter: https://twitter.com/tferriss/ Follow Tim Ferriss on Instagram: https://www.instagram.com/timferriss/ Like Tim Ferriss on Facebook: https://www.facebook.com/TimFerriss/ [00:00] Start [00:48] Eddy Cue magic. [01:32] Rich's morning routine and workout philosophy. [05:44] The Breakfast Club [09:10] How Brad Chase at Microsoft taught Rich to swing big. [11:21] The failed DOS for Dummies book bundle project. [14:31] Steering a company toward a culture of innovation. [16:09] Rich's journey from management consulting to Microsoft. [20:22] How Expedia came to be. [28:36] Pitching and recruiting team talent. [32:01] Degree design at Stanford. [34:34] Realizing the value of real work as a youth. [36:37] A fascination with Italy. [38:00] Selling Expedia to Barry Diller/IAC. [38:42] Dara Khosrowshahi's role in Expedia's acquisition.* [44:06] From a post-Expedia sale sabbatical in Italy to the birth of Zillow with Lloyd Frink. [51:03] “Big pond, good fishermen" as business criteria. [52:12] Early Zillow mistakes. [55:18] The Zestimate: Zillow's killer feature. [56:41] Making lemonade from the lemons of Zillow's launch day server crash. [58:56] Rich's provocation marketing playbook. [01:00:39] Regulatory battles and resistance to industry disruption. [01:05:48] Founding Glassdoor and its "give to get" data collection model. [01:07:27] Avvo and rating attorneys — legal challenges as marketing. [01:10:12] Digital marketplaces and Google disintermediation concerns. [01:14:57] How Rich names companies to be memorable. [01:22:04] Working with Benchmark Capital. [01:25:55] What serving on a board looks like and Rich's membership criteria: "Is it local? Is it fun? Is it lucrative?" [01:34:05] Rich's motivation and regimen for staying healthy in his 50s. [01:42:03] Cultivating leadership through absence — the two-week disconnected trip. [01:44:17] Building a good company by keeping good company. [01:46:05] Developing the skill to fire people as a win/win proposition. [01:48:55] Rich's family tattoo design and symbolism. [01:51:36] Advice for balancing family and professional life. [01:54:56] The benefits of distributed workforces post-pandemic. [01:57:14] Recommended reading. [02:06:09] Rich's billboard. [02:09:58] The importance of sabbaticals and disconnecting from digital devices. [02:11:42] Taking up Procreate digital art during COVID. [02:13:09] Parting thoughts.

Rich BartonguestTim Ferrisshost
Apr 17, 20252h 14mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 0:48

    Start

    1. RB

      I get in bed at, like, 1:00 in the morning after getting home. Sarah's super pregnant. I get a tap on the shoulder at 3:00 AM.

    2. TF

      [laughs]

    3. RB

      She's an OB, so she knows what's going on.

    4. TF

      Yeah.

    5. RB

      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?"

    6. TF

      [laughs]

    7. RB

      Which is what I promised the team. [laughs]

    8. TF

      [laughs]

    9. RB

      And then we went to the hospital, and while the IPO was happening, my son was being born. [upbeat music]

  2. 0:48 – 1:32

    Eddy Cue magic.

    1. RB

      I know Eddy Cue a little bit.

    2. TF

      Yeah.

    3. RB

      He's a friend, and there was a point at which... You know, I like to observe magic product things.

    4. TF

      Yeah.

    5. RB

      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.

    6. TF

      Mm-hmm.

    7. RB

      On mute. And at one point a couple years ago, I moused off the left edge of the screen and it seamlessly went onto the... And my-

    8. TF

      [laughs]

    9. RB

      ... 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,"

    10. TF

      [laughs]

    11. RB

      "It's an extended monitor."

    12. TF

      Yeah.

    13. RB

      And I texted him immediately. I'm like, "Oh, Eddy, it's magic. I love magic."

    14. TF

      [laughs]

  3. 1:32 – 5:44

    Rich's morning routine and workout philosophy.

    1. TF

      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?

    2. RB

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

    3. TF

      Yeah. Got it. Okay.

    4. RB

      They just don't wallow in the bullshit.

    5. TF

      Yeah.

    6. RB

      And regular news makes me feel bad.

    7. TF

      Yeah.

    8. RB

      And CNBC at best makes me feel good, and most of the time is just mid. That's fine.

    9. TF

      Yeah. [laughs]

    10. RB

      You know? And I get the news.

    11. TF

      Yeah.

    12. RB

      You know, and I get the news, and I'm interested in business and companies and strategy and-

    13. TF

      Yeah

    14. RB

      ... trends and, you know. It is pretty funny channel. It kind of gets on repeat. You don't need to watch it very long.

    15. TF

      [laughs]

    16. RB

      But they get good interviews too. So anyway. I usually don't have the volume on. I have the, kind of the close captions scrolling.

    17. TF

      Uh-huh.

    18. RB

      And then if something catches my eye, like, then I go do it.

    19. TF

      So let's take a closer look then-

    20. RB

      Yeah

    21. TF

      ... at the other screen.

    22. RB

      Yeah.

    23. TF

      You have your coffee.

    24. RB

      Yeah.

    25. TF

      What time is this?

    26. RB

      Yeah, I'm a pretty early riser.

    27. TF

      Mm-hmm.

    28. RB

      6:30 I get up usually.

    29. TF

      Mm-hmm.

    30. RB

      And long before Sarah-

  4. 5:44 – 9:10

    The Breakfast Club

    1. RB

      without that.

    2. TF

      All right. So we're gonna talk about the workout. For people who are audio only, this guy looks like a, I don't know, how you... A Marvel character meets Abercrombie & Fitch model.

    3. RB

      [laughs]

    4. TF

      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 gonna talk about the training because I have this working pet theory that [laughs] longevity may be inversely correlated with the number of things that you do for longevity. [laughs] 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.

    5. RB

      Yeah.

    6. TF

      So when you start throwing the kitchen sink plus plus at your body, the likelihood of you heading in the wrong direction-

    7. RB

      Yeah

    8. TF

      ... is probably higher or just as high.

    9. RB

      My observation is the harder you push against something, the harder it pushes back.

    10. TF

      Yeah.

    11. RB

      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-

    12. TF

      Yeah

    13. RB

      ... 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-

    14. TF

      Mm-hmm

    15. RB

      ... parent.

    16. TF

      Yeah.

    17. RB

      While Sarah became more beautiful. She stays up late.

    18. TF

      Mm-hmm.

    19. RB

      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.

    20. TF

      Mm-hmm.

    21. RB

      And I love to cook. And so our house is set up, like, we have a kitchen island-

    22. TF

      Mm-hmm

    23. RB

      ... with a big, a big bar-

    24. TF

      Mm-hmm

    25. RB

      ... with stools, and on- 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-

    26. TF

      [laughs]

    27. RB

      ... uh, uh, I would make. Which was so fun.

    28. TF

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

    29. RB

      Whatever they wanted.

    30. TF

      Yeah.

  5. 9:10 – 11:21

    How Brad Chase at Microsoft taught Rich to swing big.

    1. TF

      All right. We're gonna double-click on a, on a bunch of things we-

    2. RB

      Yeah

    3. TF

      ... passed over. Let's hop for the, 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?

    4. RB

      Brad Chase? [laughs]

    5. TF

      Yeah.

    6. RB

      Uh-

    7. TF

      What impact did he have on your life?

    8. RB

      He was a great guy. He was my first real boss out of college. That's not quite right, but it's close to right. Brad was a group product manager at Microsoft.

    9. TF

      Mm-hmm.

    10. RB

      Microsoft was my, you know, I'll, I'll call it my first job out of college.

    11. TF

      Mm-hmm.

    12. RB

      This is 1991. Microsoft had only about 3,000 people at the time.

    13. TF

      Mm-hmm.

    14. RB

      Um-

    15. TF

      And just for reference-

    16. RB

      Yeah

    17. TF

      ... because I have no idea-

    18. RB

      Yeah

    19. TF

      ... what, how many employees do you think they have now?

    20. RB

      Ooh.

    21. TF

      It's gonna be a multiple of that, of course.

    22. RB

      3, 300, 400,000.

    23. TF

      Yeah. Yeah, orders of magnitude.

    24. RB

      Multiple orders of magnitude. Yeah. Two to three. And the product managers were kind of this, you know, elite little group of, of really smart people, and we weren't very big. And he was my boss when we were working on MS-DOS 5-

    25. TF

      [laughs]

    26. RB

      ... which maybe I would say we'll have to go two standard deviations out in your audience distribution curve to find anybody who really knows what MS-DOS 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.

    27. TF

      [laughs]

    28. RB

      You're not gonna engage on the geeky stuff, but it was a really big product, and my job was to create the packaging, manage the manufacturing, and figure out how to get this physical product into the Egghead. Some of you will remember Egghead. Egghead was a retail software-

    29. TF

      Mm-hmm

    30. RB

      ... you know, store, and to push the product out into Egghead. That was my first job. And Brad was a guy who... My big... He, he's one of my mentors, you know. I only worked for him for a short period of time, but 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, you know, supported me in it, and it failed miserably.

  6. 11:21 – 14:31

    The failed DOS for Dummies book bundle project.

    1. TF

      Is this the book project?

    2. RB

      Yeah.

    3. TF

      You wanna tell people about it? [laughs]

    4. RB

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

    5. TF

      It is, but-

    6. RB

      Yeah

    7. TF

      ... the details help paint a picture.

    8. RB

      Okay.

    9. TF

      Right? People can conjure a visual in their head.

    10. RB

      All right. It's become a huge series. There's a series For Dummies, Blank For Dummies.

    11. TF

      Yep.

    12. RB

      And the book that the Dummies series was founded on was DOS For Dummies.

    13. TF

      [laughs]

    14. RB

      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 wanna 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 & Noble and Borders bookstores.

    15. TF

      Sure.

    16. RB

      The bookstore experience was huge back then. And DOS for Dummies sold millions and millions of copies of this book in Barnes & Noble and Borders. And so I was like, "Why don't we do a bundle with, with DOS for Dummies and have that be the manual for the upgrade?"

    17. TF

      Mm-hmm.

    18. RB

      Bundle it together, the book and the upgrade-

    19. TF

      Seems reasonable

    20. RB

      ... and distribute it through bookstores. How brilliant. [laughs] And so I went and met with, like, one of the Riggio guys at Barnes & Noble. I met with the guy who created the Dummies 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.

    21. TF

      [laughs]

    22. RB

      Built a bunch of it, probably cost us eight to 10 bucks a unit.

    23. TF

      Yeah.

    24. RB

      Okay? Which is a lot-

    25. TF

      Yeah, it's a lot

    26. RB

      ... for COGS, right?

    27. TF

      Yeah.

    28. RB

      Cost of goods sold. I can't remember how many we built, but it was at best a C-

    29. TF

      [laughs]

    30. RB

      ... you know, maybe a D. Uh-

  7. 14:31 – 16:09

    Steering a company toward a culture of innovation.

    1. TF

      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 you... there must be some constraints on things so that you don't light the whole house on fire.

    2. RB

      Yeah.

    3. TF

      Right?

    4. RB

      Yeah.

    5. TF

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

    6. RB

      Right.

    7. TF

      At the same time, you don't want some rogue trader like [laughs] taking-

    8. RB

      That's right. That's right

    9. TF

      ... Paris turns or whatever.

    10. RB

      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, you know, saying your culture is X, Y, Z is very different from having people who channel that, those traits that you want. And so my method for doing this is to make sure we're really diligent about finding those innovators and the entrepreneurs sometimes who the intrapreneurs, let's call them, okay? The inside entrepreneurs, and protect them a little bit because sometimes they're different and, you know, mainline corporate culture sometimes rejects, often rejects the innovators-

    11. TF

      Yeah

    12. RB

      ... and the ones who want to disrupt whatever, just want rock the boat a little bit, and you really do need to rock the boat to innovate. And so the leadership needs to hire, cultivate, protect, and invest in those people.

    13. TF

      Yeah.

    14. RB

      Yeah.

    15. TF

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

    16. RB

      That's right

    17. TF

      ... corporate immune system.

    18. RB

      Which is just, it's just natural.

    19. TF

      Yeah.

    20. RB

      You know?

    21. TF

      All

  8. 16:09 – 20:22

    Rich's journey from management consulting to Microsoft.

    1. TF

      right. So let's come back to one thing you mentioned. You said in effect, not totally true, but let's consider Microsoft first job out of college. What was the actual first job out of college?

    2. RB

      I was one of these, you know, high performance, uh-

    3. TF

      Ooh, there's a confession coming

    4. RB

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

    5. TF

      Management consulting?

    6. RB

      Yeah.

    7. TF

      Really? Oh.

    8. RB

      Yes. Yes.

    9. TF

      No.

    10. RB

      And I know it, I know-

    11. TF

      Say it ain't so, Rich

    12. RB

      ... I know, but this, it was funny. There's a, there's a good story here. [laughs] I mean, I don't know if it's a good story, but we'll tell it.

    13. TF

      Yeah. [laughs]

    14. RB

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

    15. TF

      Yeah

    16. RB

      ... when I was a senior-

    17. TF

      Yeah

    18. RB

      ... of course, that's the job I wanted. You know, there was like strategic planning at Disney. There was the kind of, you know, investment banking training program, analyst program, and there was like the strategy management consultant, and those were like, you know, the big ones. And it was the most competitive, hardest to get, so that's how I got tracked.

    19. TF

      Mm-hmm.

    20. RB

      And I took a job as a strategy consultant in Boston, Cambridge, right out of college. I knew pretty damn quickly it wasn't for me.

    21. TF

      Was it by like BCG or who was...

    22. RB

      It was a spinoff of BCG-

    23. TF

      Okay

    24. RB

      ... called Alliance Consulting Group. Great group of people, super smart.

    25. TF

      Mm-hmm.

    26. RB

      It was going into a recession, though, in ni- 1989, and so a lot of people ended up losing their jobs. However, the interesting thing was one of my besties at Stanford, Nina Roberts, who was an engineer with me, we were both interviewing for all the same jobs. And, you know, she didn't get the big job, but she got this little tech company in Seattle, Microsoft.

    27. TF

      [laughs]

    28. RB

      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. It would've, that would've been, yeah, we, you know... I wouldn't be talking with you now.

    29. TF

      [laughs]

    30. RB

      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. 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-

  9. 20:22 – 28:36

    How Expedia came to be.

    1. TF

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

    2. RB

      Okay.

    3. TF

      Right? How does this happen?

    4. RB

      Yeah.

    5. TF

      I'll just leave it broad.

    6. RB

      Well, back to the earlier conversation we had about taking big swings and intrapreneurial, the how on how this happened is that Expedia was a ven- 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-

    7. TF

      Mm-hmm

    8. RB

      ... is a doctor, and she was in medical school at Northwestern and was applying to her residencies. She's an OBGYN. And there's only one residency, OBGYN residency, in Seattle, where I lived, with only six or seven residents a year, and one of the most attractive residencies in the country, so super competitive. And so we were engaged and then soon married after that. We got married pretty young. And I was like, "Well, she's not gonna match out here in Seattle, so I'd, I'd better get ready to move to New York City or, you know," this probably would've been New York City-

    9. TF

      Mm-hmm

    10. RB

      ... where she matched. And so about a year, this during... 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.

    11. TF

      Now, this is gonna maybe sound-

    12. RB

      Yeah

    13. TF

      ... like a side quest, but when you say you moved, is it... Did you just put in a request? How did that... Like, how easy is that to do?

    14. RB

      At great companies, it's relatively easy.

    15. TF

      Relatively easy. Okay.

    16. RB

      Especially for people who are tagged as high potential.

    17. TF

      Yep.

    18. RB

      But it's still not easy-

    19. TF

      Yeah

    20. RB

      ... of course. Brad, who was my boss at the time, couldn't believe, like, we're launching Windows 95. This is gonna be the biggest launch of all time-

    21. TF

      Mm-hmm

    22. RB

      ... in the software industry, or maybe one of the biggest product launches of all time. I don't know if you remember that.

    23. TF

      I do.

    24. RB

      It was a big deal. And about six months before we launched, I had a big job there. About six months before we launched, I, 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, I was gonna have to leave Microsoft.

    25. TF

      Mm-hmm.

    26. RB

      And I wanted to start a company.

    27. TF

      Mm-hmm.

    28. RB

      And it wasn't gonna be an operating system.

    29. TF

      Yeah.

    30. RB

      Okay? Like that, that just wasn't gonna happen for, for reasons that, you know, we don't need to get into-

  10. 28:36 – 32:01

    Pitching and recruiting team talent.

    1. RB

      Microsoft was getting so big at the time that people could hide out in random corners of Microsoft, and as long as Windows NT, the operating system, succeeded or Office, Microsoft Office succeeded, they could make a lot of money off their stock options.

    2. TF

      Mm-hmm.

    3. RB

      And so that's basically a compensation accountability disconnect.

    4. TF

      Mm-hmm.

    5. RB

      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.

    6. TF

      Mm-hmm.

    7. RB

      Like, I would not have stayed. I would have gone out-

    8. TF

      Right

    9. RB

      ... and started something on the outside, 'cause the opportunity was so great. And so, you know, and Steve Ballmer understood this really well.

    10. TF

      Got it. So it was like a talent retention pitch.

    11. RB

      Sort of.

    12. TF

      Yeah.

    13. RB

      Sort of. And so he's like, "Yeah, we'll take a flyer on it," and, 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. It was all but two people s- decided to come, take the adventure, give it a rip. I was 32 years old, 31, 32 years old.

    14. TF

      Now, were you pitching those people yourself?

    15. RB

      Yeah.

    16. TF

      What was the pitch? 'Cause it's gonna be different than the pitch to Ballmer, right?

    17. RB

      Yeah, way different. I mean, I had had this idea for a while, and so the people I recruited, back to an earlier comment I made, the, the people that were on the team were the people who were the adventurers and the ones who would have left.

    18. TF

      Mm-hmm

    19. RB

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

    20. TF

      Ah, yeah.

    21. RB

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

    22. TF

      Mm-hmm

    23. RB

      ... walking. The, the S1 is highlighted and, like, there's annotation, and I'm having to answer, you know. Those were my toughest investors, actually.

    24. TF

      [laughs]

    25. RB

      And anyway, 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.

    26. TF

      Yeah.

    27. RB

      And so when Thelma and Louise went off the cliff-

    28. TF

      [laughs]

    29. RB

      ... as you say, um, we were already public, okay?

    30. TF

      Yeah.

  11. 32:01 – 34:34

    Degree design at Stanford.

    1. TF

      How did you learn to pitch? How did you learn to pitch different stakeholders, right? Because you're talking about employees, Ballmer, Gates, spouses. Like, that is a skill set, right?

    2. RB

      Persuasion.

    3. TF

      Yeah. How did you develop that?

    4. RB

      Uh, it just must have been a- an innate thing that got a lot of exercise-

    5. TF

      Mm-hmm

    6. RB

      ... as I was growing up.

    7. TF

      Yeah.

    8. RB

      I'm an... I was an engineer by degree-

    9. TF

      Mm-hmm

    10. RB

      ... but never a practicing engineer. I was an engineer because I liked technology.

    11. TF

      Mm-hmm. What type of engineer initially?

    12. RB

      Well, 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.

    13. TF

      Mm-hmm. Now, industrial engineer would be like you end up going to a Smart Design or one of those types of companies, or how were you thinking your path would unfold?

    14. RB

      It doesn't... It's not a degree anymore at Stanford. It's called Management Science and Engineering, and then there's kind of a symbolic systems things. The industrial engineering degree, which kind of sunsetted, was really a kind of manufacturing efficiency.

    15. TF

      I got it. Okay.

    16. RB

      Okay?

    17. TF

      I got it, yeah.

    18. RB

      Optimization-

    19. TF

      Mm-hmm

    20. RB

      ... simulation, you know, lots of, lots of computer work-

    21. TF

      I got it. Okay

    22. RB

      ... going into the, the design of making things more efficiently.

    23. TF

      Yeah, kind of like the operations research finance department-

    24. RB

      That's right

    25. TF

      ... at other places.

    26. RB

      That's right.

    27. TF

      Yeah.

    28. RB

      I did it just because it was Bachelor of Science, not a Bachelor of Arts, and it was the most business-y of the engineering disciplines.

    29. TF

      Mm-hmm.

    30. RB

      At Stanford, they called it imaginary engineering because the mechanical-

  12. 34:34 – 36:37

    Realizing the value of real work as a youth.

    1. RB

      Unlike a lot of kids today, I worked real summer jobs, you know?

    2. TF

      [laughs]

    3. RB

      My kids generally did, actually. My kids have worked real summer jobs.

    4. TF

      So what are we talking, like bus boy? What are, what are we talking?

    5. RB

      Yeah, I mean, my daughter... I'm just thinking of what their jobs are right now. My daughter spent... You, you're gonna know this place. You know, after Gurney's was redone-

    6. TF

      [laughs]

    7. RB

      ... it became like this club scene. This is out in Montauk.

    8. TF

      Once it got fancied up.

    9. RB

      It got super fancy. [laughs]

    10. TF

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

    11. RB

      [laughs]

    12. TF

      Anyway, yeah. [laughs]

    13. RB

      Uh, yep. Um, so it was after her sophomore year in college, I think. Or fresh- yeah, sophomore year. And I'm like, "Honey, you've got a place to stay out in the Hamptons. You don't need to get on the freaking, you know, 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... What do you call the... Who's the person that stands at the counter when-

    14. TF

      The hostess?

    15. RB

      The hostess at the club part of Gurney's.

    16. TF

      Oh, God. [laughs]

    17. RB

      Okay? Where, where it was like thou- $2,000 tables.

    18. TF

      Yeah, yeah. That's quite an education-

    19. RB

      It's an amazing-

    20. TF

      ... human nature

    21. RB

      ... human nature job. [laughs]

    22. TF

      Oh my God.

    23. RB

      She had a crazy successful, interesting learning experience.

    24. TF

      Yeah.

    25. RB

      Yeah, and that... We, we had fun watching it happen, and we also got tables at Gurney's.

    26. TF

      [laughs]

    27. RB

      Uh, 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 of doing that, like, well, now 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 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-

    28. TF

      Wow

    29. RB

      ... in the summer painting, and that was-

    30. TF

      Yeah

  13. 36:37 – 38:00

    A fascination with Italy.

    1. TF

      and why did you go to Italy at all?

    2. RB

      Why did I wanna go when I was in school?

    3. TF

      Mm-hmm.

    4. RB

      I am not, have no Italian heritage, as you can probably tell.

    5. TF

      [laughs]

    6. RB

      Uh, uh, but I went to Italy and Greece when I was in high school with my Latin teacher, and just had these awesome kinda kid high school trips.

    7. TF

      Mm-hmm.

    8. RB

      And I, while I was in Italy I literally fell in love with the whole vibe.

    9. TF

      Yeah.

    10. RB

      Like, the food, the wine, the girls, the just, the family, culture, the kinda work is not that im- as important, you know. And I kinda fell in love with it, and kept going back.

    11. TF

      Mm-hmm.

    12. RB

      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, three little kids, and I was leaving after, after Barry bought it. I wanted to give space to the next team. And I said, "Let's go back to Italy."

    13. TF

      Mm-hmm.

    14. RB

      And so we moved to Florence for a year after we sold Expedia. In fact, Nina, who I was talking about before, she was living there, married to a European guy. And St- I'd gone to Stanford there when I was a junior, and I'd kept in touch with the woman who ran the Stanford program, Linda. And so we kinda moved to Florence and went back to school, and paint- learned how to paint, and s- started road biking. Anyway, so I ju- I love the whole Italy vibe.

  14. 38:00 – 38:42

    Selling Expedia to Barry Diller/IAC.

    1. TF

      Mm-hmm. Let's take a closer look at the, the Barry Diller transaction.

    2. RB

      Yeah.

    3. TF

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

    4. RB

      Yeah, so Expedia had been public for maybe four years, and had become very successful and pretty big, pretty highly valued in the market. And I think it came about ... I mean, Barry was kinda interest- he was building a interactive conglomerate called-

    5. TF

      IAC

    6. RB

      ... IAC, right.

    7. TF

      Mm-hmm.

    8. RB

      USA Networks and then-

    9. TF

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

  15. 38:42 – 44:06

    Dara Khosrowshahi's role in Expedia's acquisition.*

    1. TF

      of stuff.

    2. RB

      Yep, and then spun it out as Match.com.

    3. TF

      Yeah.

    4. RB

      You know? And yeah, he was, post his media career, he got into interactive media and he started buying stuff. And the gu- a guy, his kinda key corporate development strategist and all around great fricking guy who worked for him was a young guy named Dara Khosrowshahi.

    5. TF

      Aha.

    6. RB

      Mm-hmm.

    7. TF

      Okay.

    8. RB

      And I think this-

    9. TF

      Folks might recognize that name

    10. RB

      ... 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-

    11. TF

      Mm-hmm

    12. RB

      ... in the online travel space, that it was already big, but it was gonna be much bigger.

    13. TF

      Mm-hmm.

    14. RB

      And they just made an offer that finally ... M- and Microsoft was the majority owner, okay? But didn't have anybody on the board even. They're-

    15. TF

      That's-

    16. RB

      ... you know, 65% of the company, they didn't have anybody on the board. Greg, they knew me, and they trusted Greg Maffei, who had left as CFO and was running the company now.

    17. TF

      That is an unbelievable level of trust.

    18. RB

      It just didn't matter to Microsoft, right?

    19. TF

      Yeah, I guess so.

    20. RB

      Just didn't matter.

    21. TF

      Just as a percentage of the total.

    22. RB

      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-

    23. TF

      Mm

    24. RB

      ... they, they did. It was a bit of a two-step deal. The IAC and Dara and Barry bought Microsoft's 65%, so we were public, but captive to IAC, and Barry Diller was my chairman for a while, and then maybe eight months later bid for the rest of it.

    25. TF

      For the remainder.

    26. RB

      And consolidated it down. We ... Or I think they kinda pushed us to buy the number two player, which was Hotels.com.

    27. TF

      Mm-hmm.

    28. RB

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

    29. TF

      So when in that journey, the, 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, there was probably a moment, I'm just guessing here, but when you had your first big summer with that painting gig-

    30. RB

      Mm-hmm

  16. 44:06 – 51:03

    From a post-Expedia sale sabbatical in Italy to the birth of Zillow with Lloyd Frink.

    1. TF

      So how the hell does Zillow happen? [laughs]

    2. RB

      Yeah.

    3. TF

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

    4. RB

      Yeah, I was still pretty young, so probably, it was '03, I was, like, 35, 36. And I was hoping art, music, r- I thought I might write books, whatever, you know, find the next chapter.

    5. TF

      Mm-hmm.

    6. RB

      'Cause I really didn't need to make... You know, I had enough to take care of myself for the rest of my life. But something I discovered a... I, I was still on a few boards-

    7. TF

      Mm-hmm

    8. RB

      ... including the IAC board, which had bought Expedia, and Netflix, where I'd been on the board since, like, 2000.

    9. TF

      Mm-hmm.

    10. RB

      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. And 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. And so I knew that we weren't gonna stay in Italy, we were gonna move back, and I was gonna, you know, do something else.

    11. TF

      Mm-hmm.

    12. RB

      Which is great to learn, you know.

    13. TF

      And then...

    14. RB

      And we did. We'd been in Italy for... We lived in Florence for a little over a year. We spent a few months skiing with the family, which was really fun, in the mountains.

    15. TF

      And you came to the US sort of-

    16. RB

      Came back to Seattle

    17. TF

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

    18. RB

      Uh, a little bit. A little bit. I didn't know if I really had another startup in me-

    19. TF

      Mm-hmm

    20. RB

      ... because I knew how much work it was, and I'd adjusted my life to prioritize some things I hadn't prioritized when I was younger-

    21. TF

      Mm-hmm

    22. RB

      ... like living well and family and body-

    23. TF

      Mm-hmm

    24. RB

      ... and mind. And I was very curious in all kinds of different things, so the venture capital opportunity w- was available to me-

    25. TF

      Mm-hmm

    26. RB

      ... 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 for good reason. Awesome guy, really smart.

    27. TF

      [laughs] I won't follow up on that. I'll let that one-

    28. RB

      We don't, we don't need to

    29. TF

      ... let that one, let that one go. [laughs]

    30. RB

      It's a fu- it's a fun story, but Lloyd... So Lloyd got fired, and Lloyd's like, "Wait, wait, wait. Don't, 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 w- it was obvious that the kind of cloud storage thing was gonna be huge. And I, I said, "Go figure that out. See what it's cost, see what..." You know. And so he disappeared for a couple weeks, so we were kind of sharing an office, and he came back, and he's like, "Yeah, 100% this is gonna work, but there's gonna be no pro- there's no profit."

  17. 51:03 – 52:12

    “Big pond, good fishermen" as business criteria.

    1. RB

      Anyway, a lot of people make the mistake, is what I was gonna say, of identifying a real problem, but it's just too small.

    2. TF

      Mm-hmm.

    3. RB

      Uber kind of to some pe- a lot of people looked too small because it was a black car TAM.

    4. TF

      Exactly.

    5. RB

      Total addressable market. But the insight that you and Gurley and Travis and-

    6. TF

      Garrett

    7. RB

      ... I guess J Cal-

    8. TF

      Yeah

    9. RB

      ... and others had was that actually no, it was gonna take not just the black car market, but taxi, transportation, and then ultimately more.

    10. TF

      It can expand the total addressable market.

    11. RB

      That's right.

    12. TF

      Right? Which-

    13. RB

      Car ownership.

    14. TF

      Yeah.

    15. RB

      Just transportation.

    16. TF

      Mm-hmm.

    17. RB

      You know, and of course obviously it's beautifully played out that way.

    18. TF

      Yeah.

    19. RB

      Took a little while to see, but it's, you know, amazing. Anyway, so big pond, good fisherman. Start after identifying the big problem, and I guess that was the guiding, 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 h- what, how we were gonna play, and we started poking at ideas for attracting audience-

    20. TF

      Mm

    21. RB

      ... with software. And we made a couple of big mistakes before we landed on the solution.

  18. 52:12 – 55:18

    Early Zillow mistakes.

    1. TF

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

    2. RB

      Pretty small venture numbers at that point, and Lloyd and I were funding it our- ourselves. You know, we put the first 5 million bucks total in with a couple of friends. So costly, but not that costly. But the first idea we were-

    3. TF

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

    4. RB

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

    5. TF

      Yeah, it was, there was self-funding for a while.

    6. RB

      Interesting.

    7. TF

      It wasn't expensive.

    8. RB

      Yeah.

    9. TF

      It wasn't overly expensive.

    10. RB

      Yeah.

    11. TF

      But...

    12. RB

      It's a good way to go as a second time founder or a non-first time founder if you actually have some resources.

    13. TF

      Mm-hmm.

    14. RB

      Because you end up with more of the company down the road.

    15. TF

      Yeah.

    16. RB

      I love Gurley. We're really close, but what, by the time Gurley or the venture capitalists come in, you know, if they're writing the first check, they're gonna end up with a big chunk of the company.

    17. TF

      Yeah.

    18. RB

      Which is great, especially if you get somebody like Bill.

    19. TF

      Yeah.

    20. RB

      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.

    21. TF

      Mm-hmm.

    22. RB

      You know, the digital auction-based marketplace.

    23. TF

      When you say it came from another company-

    24. RB

      Yeah

    25. TF

      ... I might not know that wrinkle.

    26. RB

      Yeah, it did. It did.

    27. TF

      Meaning they acquired something or they-

    28. RB

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

    29. TF

      Oh, Bill Gross.

    30. RB

      Bill? Yeah. I-

  19. 55:18 – 56:41

    The Zestimate: Zillow's killer feature.

    1. TF

      Mm-hmm.

    2. RB

      But in pursuit of price discovery, we found the Zestimate, which was our killer, our killer feature. And the visual on the Zestimate that's in my head, that kind of popped in, in our collective heads on the home auction web experiment, was a real time estimated value alga- algorithmically driven as your Google Map zooming over neighborhoods-

    3. TF

      Mm

    4. RB

      ... looking. We wanted prices on every roof.

    5. TF

      Yeah.

    6. RB

      Because everything should have a price. That was it.

    7. TF

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

    8. RB

      Short.

    9. TF

      It was short, right?

    10. RB

      Short. There were no smartphones, but it was obvious.

    11. TF

      Mm-hmm.

    12. RB

      Like, I was like, "Whoa." And then I also had in my head, homes are, for American homeowners, oftentimes their largest asset-

    13. TF

      Mm-hmm

    14. RB

      ... and the bulk of their wealth. And people care a lot about it.

    15. TF

      Yeah.

    16. RB

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

    17. TF

      Okay.

    18. RB

      In my gut, I knew that was c- 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."

    19. TF

      Mm-hmm.

    20. RB

      And so the aerial view with the numbers and 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.

    21. TF

      [laughs] Okay.

  20. 56:41 – 58:56

    Making lemonade from the lemons of Zillow's launch day server crash.

    1. TF

      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?

    2. RB

      [laughs] AWS didn't exist.

    3. TF

      I know. [laughs]

    4. RB

      [laughs] You knew that. You baited me.

    5. TF

      [laughs]

    6. RB

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

    7. TF

      Did, did you-

    8. RB

      Server in a closet

    9. TF

      ... is it true you forbade Christmas lights or something? Like, you're like preserving electricity and compute power and all this stuff?

    10. RB

      I don't remember that.

    11. TF

      Who knows.

    12. RB

      I don't remember.

    13. TF

      All right. All right. Got it.

    14. RB

      But, but David or C-

    15. TF

      The things of lore

    16. RB

      ... David Beitel, 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.

    17. TF

      Yeah.

    18. RB

      Yeah. I, I, I believe. I remember our launch blog post with Garrett, who worked for David, like doing the-

    19. TF

      [laughs]

    20. RB

      What's the professor in, uh-

    21. TF

      Doc-

    22. RB

      Doc Brown

    23. TF

      ... from Back to the Future.

    24. RB

      3.0 gigawatts.

    25. TF

      Whatever. [laughs]

    26. RB

      Because we launched, and millions of people showed up because Walt Mossberg, who was-

    27. TF

      Mm-hmm

    28. RB

      ... who's the equivalent... Is there any equivalent of Walt Mossberg now? No? Walt-

    29. TF

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

    30. RB

      Yeah.

  21. 58:56 – 1:00:39

    Rich's provocation marketing playbook.

    1. RB

      And, and I've since developed a pretty good playbook around, I guess, what I would call provocation marketing, you know.

    2. TF

      Yeah.

    3. RB

      When you have really provocative feature that you know people are gonna feel emotional about one way or the other, and they're gonna talk about it-

    4. TF

      Mm-hmm

    5. RB

      ... you're onto something.

    6. TF

      Uh, what are some aspects of that toolkit or the playbook?

    7. RB

      I mean, having data, like having a stream of data that people are interested in. At Glassdoor, which I did with, uh, Bob Hohman, who, 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.

    8. TF

      Mm-hmm.

    9. RB

      And so the playbook that Amy kind of put together was building a PR data distribution infrastructure down to the local-

    10. TF

      Remind me who Amy is, sorry.

    11. RB

      Amy was our, our marketing chief-

    12. TF

      Got it

    13. RB

      ... 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-

    14. TF

      Mm

    15. RB

      ... once upon a time. And if you could wire that up to just feed, constantly feed the endless appetite... F- housing is just an important topic, right?

    16. TF

      Mm-hmm.

    17. RB

      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, which was a terrific brand builder for us, rather than spending ad money, and then just having the Zestimate be so provocative, like, you know, high school boyfriend's house.

    18. TF

      [laughs]

    19. RB

      Philanthropist development team that are trying to figure out who's a good target.

    20. TF

      Mm.

    21. RB

      You know, whatever. Like it's a-

    22. TF

      Lots of applications

    23. RB

      ... the Zestimate. Lots of application.

  22. 1:00:39 – 1:05:48

    Regulatory battles and resistance to industry disruption.

    1. RB

      Yeah. Yeah.

    2. TF

      I know you had a lot of fans. I think the Arizona attorney general was a fan. [laughs]

    3. RB

      That's a deep cut.

    4. TF

      [laughs]

    5. RB

      Wow. [laughs]

    6. TF

      No, but this is of interest to me-

    7. RB

      Yeah

    8. TF

      ... because there's, there's opposition also.

    9. RB

      Oh, yeah.

    10. TF

      Right? And my God-

    11. RB

      Lot of agents, lot of agents that knew

    12. TF

      ... I mean, the number of... I don't think they were actual ulcers, but just the rollercoaster ride that I was also on with Uber-

    13. RB

      Yeah

    14. TF

      ... from a regulatory mobbed up local fill-in-the-blank perspective.

    15. RB

      Yep.

    16. TF

      I mean, it was just nonstop battles.

    17. RB

      Yep.

    18. TF

      And that was just part of the deal.

    19. RB

      Yep.

    20. TF

      Right? If you wanna-

    21. RB

      And actually part of the playbook.

    22. TF

      Yeah. Yeah.

    23. RB

      Honestly.

    24. TF

      All right.

    25. RB

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

    26. TF

      Yeah. So what happened with you guys?

    27. RB

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

    28. TF

      Yeah.

    29. RB

      You know, the taxi commission in Uber's case.

    30. TF

      Yeah.

  23. 1:05:48 – 1:07:27

    Founding Glassdoor and its "give to get" data collection model.

    1. RB

      I think.

    2. TF

      So if you were teaching a class, maybe you already have, I have no idea, related to provocation marketing-

    3. RB

      Yeah.

    4. TF

      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.

    5. RB

      Yep.

    6. TF

      What would other elements of the class be? Other resources, principles, anything at all.

    7. RB

      While I try to figure out a structure here on the fly, to give a couple other examples of stuff that I've-

    8. TF

      Yeah

    9. RB

      ... I've, I've been involved with. So I co-founded Glassdoor, which many people out there may, may know, and our provocation data marketing feature was how much money do people make.

    10. TF

      Mm-hmm.

    11. RB

      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 a little bit taboo for a lot of people, so it was inherently secret and provocative.

    12. TF

      Mm-hmm.

    13. RB

      Okay? And then Robert Hohman, who is my co-founder- And, and the team, they had a data collection problem 'cause it was ultimately user-generated content. People, 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.

    14. TF

      Ah.

    15. RB

      You show me yours, I'll show you mine.

    16. TF

      [laughs]

    17. RB

      Very good.

    18. TF

      That's very clever.

    19. RB

      Very clever. And say, "Hey, I'll give you a little taste, but if you wanna see any more data, you've gotta share your salary and your title and your company, and we promise you'll be anonymous. And do a company review."

  24. 1:07:27 – 1:10:12

    Avvo and rating attorneys — legal challenges as marketing.

    1. RB

      How is the C-

    2. TF

      How many people screwed that up where they're the only person in that position? [laughs] I guess it has to be large.

    3. RB

      And we had protocols for that.

    4. TF

      [laughs] Yeah.

    5. RB

      Yeah, we did have protocols for that. We also then solicited feedback on what it's like to work at the company.

    6. TF

      Yeah.

    7. RB

      And, you know, CEOs are kind of public figures, so okay, we're gonna let you review the CEO performance.

    8. TF

      [laughs]

    9. RB

      And we knew all those things would-

    10. TF

      Yeah

    11. RB

      ... provoke, right? We knew some CEOs would go crazy, you know? So there's another example while I'm formulating a framework.

    12. TF

      Mm-hmm.

    13. RB

      The, another one is with another former Expedia guy, Mark Britton, we founded a company called Avvo-

    14. TF

      Mm

    15. RB

      ... which was in the legal space, and we decided to rate attorneys.

    16. TF

      Mm-hmm.

    17. RB

      Systematically rate attorneys. This had never happened before. It was just kinda like TripAdvisor for attorneys.

    18. TF

      Mm-hmm.

    19. RB

      You can have a 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 gonna get sued because we were rating attorneys. [laughs]

    20. TF

      [laughs] Yeah. I mean, definitely a great way to kick the hornet's nest.

    21. RB

      Some investors, when we were raising money, I remember traveling around, you know, doing the Sand Hill shuffle with Mark, and I remember some people saying, "Well, is this legal? You're gonna get... Can you rate people? You're gonna get sued. I'm not gonna invest." And we were like, "Yeah, we're gonna get sued."

    22. TF

      [laughs]

    23. RB

      You know, did you see Die Hard? You remember Die Hard where the, the German terrorist leader, you know, is waiting for the last lock to open, and he needs the power to go down-

    24. TF

      Yeah

    25. RB

      ... in order to be able to get the bearer bonds out of the Nakatomi Plaza safe?

    26. TF

      [laughs] Yeah.

    27. RB

      Okay? And the people are like, "How is he gonna get the power to go down?" And he's like... He said, "Ladies and gentlemen, I'll give you the FBI." And they came in on those things, and the FBI, the playbook said, "All right, cut the power." [laughs]

    28. TF

      [laughs] Yeah, yeah, yeah.

    29. RB

      Remember?

    30. TF

      Yeah, yeah, yeah.

  25. 1:10:12 – 1:14:57

    Digital marketplaces and Google disintermediation concerns.

    1. TF

      And then you have... You name it, right? Everybody's there. All, all the big players.

    2. RB

      Yep.

    3. TF

      And so that's the Sand Hill shuffle. So why not be afraid of the lawsuits? What did you guys know that the guys who said, "Nuh-uh-uh, I'm not gonna touch that with a 10-foot pole"?

    4. RB

      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.

    5. TF

      Mm-hmm.

    6. RB

      And the way we did it, we were 100% convinced of our legal grounds.

    7. TF

      Yeah.

    8. RB

      And so-

    9. TF

      But people could still just consume so much energy, right?

    10. RB

      No doubt. So we raised money to deal with that, but we knew it was gonna be pretty cheap lawsuits.

    11. TF

      Yeah.

    12. RB

      And we could provide the legal, most of the legal billing ourselves anyway.

    13. TF

      Mm-hmm.

    14. RB

      And so it would be cheaper than hiring some fancy firm.

    15. TF

      A lot cheaper.

    16. RB

      And so we were convinced, and after we won the first few suits, they lost steam. The lawyers lost steam on, on, on suing. So yeah, I mean, it caused some venture capitalists to not do it, but the more kind of disruptive-oriented folks were like, "Yeah, great."

    17. TF

      So what happened with Avvo?

    18. RB

      It did pretty well 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, search engine optimization, you know, collecting Google Search traffic on one side and trying to monetize leads on the other.

    19. TF

      Mm-hmm.

    20. RB

      As time wore on, a lot of those business models got somewhat disintermediated.

    21. TF

      Mm-hmm.

    22. RB

      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.

    23. TF

      Could you explain that just one more time, and maybe an example-

    24. RB

      Yeah

    25. TF

      ... would be helpful. So let's just say-

    26. RB

      Yeah

    27. TF

      ... they're TripAdvisor for X.

    28. RB

      Yep.

    29. TF

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

    30. RB

      Yep.

  26. 1:14:57 – 1:22:04

    How Rich names companies to be memorable.

    1. RB

      and growing.

    2. TF

      All right. So I haven't forgotten about the provocation marketing class. However-

    3. RB

      Yeah. Okay

    4. TF

      ... I think this is a great place to buy you some more time-

    5. RB

      Yeah

    6. TF

      ... and talk about naming.

    7. RB

      Okay. Oh. [laughs]

    8. TF

      How do you, how do you name companies?

    9. RB

      You saw that blog post. [laughs]

    10. TF

      [laughs]

    11. RB

      As an all... I played around with blogging like all of us. It really stuck with some-

    12. TF

      [laughs]

    13. RB

      ... and it didn't with others. I probably only had, like, 10 posts on my blog, but one of them was naming, 'cause I've, I've had a lot of fun naming companies.

    14. TF

      Mm-hmm.

    15. RB

      And I gave advice on naming. I think the title of the post... The site it's on is called hopperanddropper.com, which is a fly fishing term-

    16. TF

      [laughs]

    17. RB

      ... which is, nobody's gone to. It's, uh, only had 20 visitors. Tim, Tim being one.

    18. TF

      Lucky 21. [laughs]

    19. RB

      [laughs] Uh, so 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 f- The 4-Hour Workweek and The 4-Hour Body-

    20. TF

      [laughs]

    21. RB

      ... you know, but I'll tell you that there are no shortcuts.

    22. TF

      [laughs]

    23. RB

      You take the shortcut to the long road, my coach Jimmy says.

    24. TF

      Yeah.

    25. RB

      Anyway, the easy way is if you're building a travel site to call it hotels.com, airlinetickets.com. You know, you name it. Every category has a literal word .com.

    26. TF

      Mm-hmm.

    27. RB

      Okay? And the advantages to that are it's easy to explain to people what you do.

    28. TF

      Yeah.

    29. RB

      And the disadvantages to that are you don't own any brand equity-

    30. TF

      Hmm

  27. 1:22:04 – 1:25:55

    Working with Benchmark Capital.

    1. RB

      for that.

    2. TF

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

    3. RB

      And local.

    4. TF

      And local.

    5. RB

      Hey, Bill.

    6. TF

      Yeah. Yeah, he's right down, right, a couple blocks from where we're sitting right now.

    7. RB

      Yeah.

    8. TF

      You have spent time at Benchmark Capital-

    9. RB

      Yeah

    10. TF

      ... 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-

    11. RB

      Oh, yeah

    12. TF

      ... way back in the day.

    13. RB

      Exciting.

    14. TF

      And [laughs] 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.

    15. RB

      Super entertaining.

    16. TF

      And so entertaining. I mean, this was the heyday, right?

    17. RB

      Yeah. Right.

    18. TF

      I mean, this was just rocket ships everywhere.

    19. RB

      Yep.

    20. TF

      So fun. Right. So you've spent time at and with Benchmark. What led you to that? Was that kind of biding time until you figured out which next big swing to take? What was the motivation, and then also, what did you learn there, or what came into greater resolution or clarity while you were there?

    21. RB

      As we chatted about before, when I was coming with my family back from that sabbatical, I'm a big believer in the sabbatical, in Italy-

    22. TF

      Mm-hmm

    23. RB

      ... and was considering the next career move, I got to know first Bruce Dunlevie at Benchmark and then Bill and the other guys. I did read E-boys then, too, which was-

    24. TF

      [laughs]

    25. RB

      ... you know, romantic kind of-

    26. TF

      Yeah [laughs]

    27. RB

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

    28. TF

      Mm-hmm. You did.

    29. RB

      I did.

    30. TF

      Yeah.

  28. 1:25:55 – 1:34:05

    What serving on a board looks like and Rich's membership criteria: "Is it local? Is it fun? Is it lucrative?"

    1. RB

      companies.

    2. TF

      Can you explain, just for folks who may not be familiar, what does it mean to sit on a board?

    3. RB

      Okay.

    4. TF

      What does that actually mean, right? And it depends board to board, I'm sure, on-

    5. RB

      Yeah

    6. TF

      ... 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?

    7. RB

      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.

    8. TF

      Mm-hmm.

    9. RB

      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 gonna be engaged. And so it's a company building exercise. And then when it's time to fundraise, can s- totally help with the, the next fundraising, can help with recruiting. One of the very best at this is... I mean, there's so many good ones, but Bill, Bill is really good, as you've seen-

    10. TF

      Mm-hmm

    11. RB

      ... in the Uber case, at really helping build companies. And a public company is a little different, you know?

    12. TF

      May I add one thing?

    13. RB

      Yeah.

    14. TF

      And I've never been on a board, but-

    15. RB

      Really?

    16. TF

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

    17. RB

      So you have a negative impression.

    18. TF

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

    19. RB

      You dodged it.

    20. TF

      Well, I feel like [laughs] ...

    21. RB

      [laughs]

    22. TF

      Yeah, dodge is a strong-

    23. RB

      Okay

    24. TF

      ... verb to use.

    25. RB

      And so that was a missile coming at you, and you-

    26. TF

      I have felt like I, at the time when these opportunities have come up, that I did not have clear criteria, and I didn't, I don't want to commit to things reactively.

    27. RB

      Yeah, okay.

    28. TF

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

    29. RB

      Okay, got it.

    30. TF

      And also, [laughs] it seems like, and definitely correct me if I'm wrong, but another responsibility of a board is to fire leadership-

  29. 1:34:05 – 1:42:03

    Rich's motivation and regimen for staying healthy in his 50s.

    1. RB

      Yuzu coconut water.

    2. TF

      Feeling, [laughs] feeling very-

    3. RB

      Infused

    4. TF

      ... well-hydrated and infused. And that is as smooth/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-

    5. RB

      Right

    6. TF

      ... da, da, da, da, including health-

    7. RB

      Yeah, yeah

    8. TF

      ... and body, things like that.

    9. RB

      Yep.

    10. TF

      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?

    11. RB

      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.

    12. TF

      Mm-hmm. Yeah.

    13. RB

      You know, the substrate is age.

    14. TF

      Yeah.

    15. RB

      And ultimately everybody probably figures this out-

    16. TF

      Yeah

    17. RB

      ... some later, sooner than others.

    18. TF

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

    19. RB

      I'm 57.

    20. TF

      Okay. God.

    21. RB

      Yeah.

    22. TF

      Wow.

    23. RB

      Yeah.

    24. TF

      You've really held onto the-

    25. RB

      Yeah, right

    26. TF

      ... youthful-

    27. RB

      Yeah, right

    28. TF

      ... glow.

    29. RB

      Everything's falling apart. [laughs]

    30. TF

      Look at me. Oh, God. I'm like American History X as of 10 years ago, and then it's just the crow's feet are turning into crow's legs. It's... But you seem to be very active.

  30. 1:42:03 – 1:44:17

    Cultivating leadership through absence — the two-week disconnected trip.

    1. RB

      And actually, a leadership development technique I often coach is for a senior leader or a middle management type leader, I encourage them to really take a vacation and disappear.

    2. TF

      Mm-hmm.

    3. RB

      Okay? And most people think that's gonna 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-

    4. TF

      For how long do you recommend?

    5. RB

      ... for two weeks.

    6. TF

      Yeah.

    7. RB

      Okay?

    8. TF

      Uh-huh.

    9. RB

      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, 'cause it's gonna arise.

    10. TF

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

    11. RB

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

    12. TF

      Yep.

    13. RB

      And when somebody's really disconnected, the senior leader is disconnected, leadership is sort of an emergent property.

    14. TF

      Mm-hmm.

    15. RB

      Okay? And it kind of emerges. So this is a long way of, 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?

    16. TF

      Mm-hmm.

    17. RB

      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.

    18. TF

      Mm-hmm.

    19. RB

      Okay, that person is not promotable.

    20. TF

      Yeah.

    21. RB

      The person who has cultivated leaders under them, that person is totally promotable-

    22. TF

      Yeah

    23. RB

      ... even though that person's more expendable, too.

    24. TF

      Yeah.

    25. RB

      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, "If I'm doing my job really, really perfectly, I can be on my surfboard."

    26. TF

      [laughs]

    27. RB

      Okay?

    28. TF

      Yeah.

    29. RB

      And nobody knows when you don't show up to work if you have eight jobs.

    30. TF

      [laughs]

  31. 1:44:17 – 1:46:05

    Building a good company by keeping good company.

    1. TF

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

    2. RB

      I mean, in a life context, it is just surrounding yourself with great people who care.

    3. TF

      Mm-hmm.

    4. RB

      You know? And 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 the stuff that she's in charge of is gonna happen well. That's an unbelievable feature to have in a partner as you're looking for a partner.

    5. TF

      Yeah.

    6. RB

      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. [laughs]

    7. TF

      [laughs]

    8. RB

      So anyway, I think it's mostly about picking the right people.

    9. TF

      Any recommendations for people who are 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.

    10. RB

      Yeah, and reference checks often are conflicting-

    11. TF

      Reference checks

    12. RB

      ... conflicted.

    13. TF

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

    14. RB

      Yeah. Two things I would say. One is my favorite section of the resume, I guess now LinkedIn, it's not really a section on LinkedIn, but is always in the very bottom, which is the interests.

    15. TF

      Mm-hmm.

    16. RB

      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.

    17. TF

      Hmm.

    18. RB

      To see a real spark.

    19. TF

      Mm-hmm.

    20. RB

      'Cause if they put it there, that is what they're interested in, and they better be able to light up on it. When I was earlier in my career, I'd, I would always make up business cases around some interest. "How big is the ski industry because you put skiing?" Whatever.

    21. TF

      Yeah.

    22. RB

      And that was always a fun stepping off point. I want to find people who are passionate people.

  32. 1:46:05 – 1:48:55

    Developing the skill to fire people as a win/win proposition.

    1. TF

      Mm-hmm.

    2. RB

      And then the second thing is get used to pulling the pitcher off the mound quickly.

    3. TF

      Firing someone.

    4. RB

      Yep.

    5. TF

      Okay.

    6. RB

      It's hard when you're early in your career. It's not as hard later.

    7. TF

      Mm.

    8. RB

      All of my mistakes as a leader have been leaving, almost all of them, have been leaving the pitcher on the mound too long-

    9. TF

      Mm-hmm

    10. RB

      ... hoping that the arm would get better. [laughs]

    11. TF

      [laughs] What have you learned in terms of process for firing? Any approach, go-to phrases, rules, right? You're going on your two-week surf trip. There's someone below you-

    12. RB

      Yeah

    13. TF

      ... who is going to fill that leadership void.

    14. RB

      Yeah.

    15. TF

      And he or she is gonna have to fire someone.

    16. RB

      Yeah.

    17. TF

      And they're like, "Hey, boss, I don't want to bother you-

    18. RB

      Yeah

    19. TF

      ... but this is something I haven't done before. Give me some advice."

    20. RB

      Yeah. Don't do it via text. [laughs] Be an upstanding person.

    21. TF

      Mm-hmm.

    22. RB

      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.

    23. TF

      Mm-hmm.

    24. RB

      Therefore, you can increase love in the world by releasing that person to find where that person belongs.

    25. TF

      Mm-hmm.

    26. RB

      That person belongs somewhere else. That person's gonna be happy somewhere. Help that person find that somewhere, but you're gonna be happier when you release that person, and that person's gonna be happier, too. And so if you make it a partnership, if you make it a joint decision effectively-

    27. TF

      Mm-hmm

    28. RB

      ... or at least get the interests aligned, which it almost always is, it's not as hard. And when you do that, you naturally are being human. If you're looking for shared alignment, that means you care. That means you're showing heart, and having heart in this situation is really important.

    29. TF

      Mm-hmm.

    30. RB

      Yeah.

  33. 1:48:55 – 1:51:36

    Rich's family tattoo design and symbolism.

    1. RB

      then.

    2. TF

      Mm-hmm. Random question. I don't know. You could be covered in tattoos, but what is the story of this tattoo?

    3. RB

      Family.

    4. TF

      All right.

    5. RB

      Five of us in the family. Things we love.

    6. TF

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

    7. RB

      It's made up of five trees. It's a snowflake in total shape, and it's a starfish in the negative space. My daughter, Josie, when she was 16, which is too young to get a tattoo- Asked Sarah if she could get a tattoo, or asked her more specifically, would she get a tattoo with her?

    8. TF

      Mm-hmm.

    9. RB

      And Sarah's like, "Pfft. What do you me-" Sorry. Like, "Sure."

    10. TF

      [laughs]

    11. RB

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

    12. TF

      Yeah, no Wile E. Coyote. [laughs]

    13. RB

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

    14. TF

      V1.

    15. RB

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

    16. TF

      Oh, the trees, you're saying.

    17. RB

      The trees are unique, too.

    18. TF

      Mm-hmm.

    19. RB

      So anyway.

    20. TF

      I dig it.

    21. RB

      Yeah, I love it. I was the only one who got it in a really visible place-

    22. TF

      Yeah

    23. RB

      ... and everybody else got jealous, 'cause I like to be able to look at it and re- remember my family.

    24. TF

      Mm-hmm.

    25. RB

      And I thought I would start getting more. We did this maybe five, six, seven years ago. I thought we'd get more. Sarah's gotten two more tattoos, [laughs] but I haven't gotten any more.

    26. TF

      [laughs]

    27. RB

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

    28. TF

      I don't.

    29. RB

      Very few people have one.

    30. TF

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

  34. 1:51:36 – 1:54:56

    Advice for balancing family and professional life.

    1. TF

      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.

    2. RB

      Yeah.

    3. TF

      What would your recommendations be to those people?

    4. RB

      For the planning on, the, the kind of constant delayers, which there are a lot of.

    5. TF

      Yeah.

    6. RB

      You know, maybe some right here.

    7. TF

      [laughs]

    8. RB

      There are a lot of out there.

    9. TF

      Yeah.

    10. RB

      Okay? And I think the fundamental logic is, This is an important thing, and I don't have enough time-

    11. TF

      Yeah

    12. RB

      ... right now, and so I'll wait till it's a better time.

    13. TF

      Mm-hmm.

    14. RB

      There's never a better time.

    15. TF

      [laughs]

    16. RB

      Like, there's never a good time. So point number one is it's not gonna get better. It's not gonna feel better. And then point number two is, like, we're built for this.

    17. TF

      Yeah.

    18. RB

      We are the successful evolutionary product of a lot of people who figured this out.

    19. TF

      [laughs]

    20. RB

      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.

    21. TF

      Mm-hmm.

    22. RB

      It's encoded. A lot of it is encoded. So it's, you know what? It's probably gonna work pretty well.

    23. TF

      [laughs]

    24. RB

      And so I am, I don't know if I'd call myself a birther. I'm an encourager of-

    25. TF

      Procreating

    26. RB

      ... let's have, let's have more babies, and I'm a really big believer in how it's such, such an important part of our own mental health, at least for me-

    27. TF

      Yeah

    28. RB

      ... to have children and from a growth perspective. And it kind of, as we get older, our ego focus naturally, the diameter of our ego sphere-

    29. TF

      Mm-hmm

    30. RB

      ... gets broader and broader, and children just, phew, blow it way out.

  35. 1:54:56 – 1:57:14

    The benefits of distributed workforces post-pandemic.

    1. TF

      Yeah.

    2. RB

      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.

    3. TF

      Yeah.

    4. RB

      Matt was very influential on me early in the pandemic. I had him blue jeans Zoom into an early company meeting early in COVID and lay out his game plan for the distributed corporation.

    5. TF

      Yeah, Matt Mullenweg, generally associated with WordPress, founder and CEO of Automattic, spelled M-A-T-T-I-C, and- ... pioneer of distributed-

    6. RB

      Yeah

    7. TF

      ... workforces.

    8. RB

      Yeah.

    9. TF

      And as a design principle from the outset has built that company to be distributed.

    10. RB

      Yeah.

    11. TF

      And therefore was very anti-fragile when COVID came along. And there were some other standout examples. I mean, Shopify did really well-

    12. RB

      Yep

    13. TF

      ... also.

    14. RB

      Yep.

    15. TF

      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've been far difficult even 10 years ago.

    16. RB

      Well, we can generalize and say it's been great for moms, but-

    17. TF

      Mm-hmm

    18. RB

      ... it's more than just moms. Like, but it has enabled really smart, very experienced moms who may have historically decided to take the off-ramp into primarily momhood rather-

    19. TF

      Mm-hmm

    20. RB

      ... than primarily climbing the corporate ladder or just executive leadership-

    21. TF

      Mm-hmm

    22. RB

      ... path, it's enabled them to come back.

    23. TF

      Yeah.

    24. RB

      And likewise now for a father, come on, as long as the company doesn't get angry when they see you in your car on the Zoom because you're at a, you know, dentist appointment for your kid or something, you know?

    25. TF

      Mm-hmm.

    26. RB

      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."

    27. TF

      [laughs]

    28. RB

      Like, "Gotta 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-

    29. TF

      Yeah

    30. RB

      ... this is just... This opens doors. This doesn't close doors.

  36. 1:57:14 – 2:06:09

    Recommended reading.

    1. TF

      What books have you either gifted a lot to other people or reread yourself? Either one.

    2. RB

      I mean, I am not your typical person probably sitting in this seat in that may- maybe I am. I am not a nonfiction business book... Sorry, Tim. I'm not, yeah.

    3. TF

      No, that's okay.

    4. RB

      Yeah. I tend not to read that stuff.

    5. TF

      Mm-hmm.

    6. RB

      Though the older I get, I occasionally will read a biography now, but-

    7. TF

      Mm-hmm

    8. RB

      ... they mean more now the older you get. But no, I am fully a, I'm a big reader, and it's fiction.

    9. TF

      Mm-hmm.

    10. RB

      And generally good fiction, although I do have, you know-

    11. TF

      Cheap thrills. [laughs]

    12. RB

      Yeah. I, yeah, I do. I do. I really love beautiful, beautiful fiction. And I like, I dabble, I've always dabbled in the kind of science fiction, magical realism-

    13. TF

      Mm-hmm

    14. RB

      ... 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-

    15. TF

      Problem solving

    16. RB

      ... yeah, exactly. To get my brain, my... I have monkey brain.

    17. TF

      Mm-hmm.

    18. RB

      Okay? And to get my monkey brain to relax, escaping into a fiction novel for me is just a fantastic release.

    19. TF

      Mm-hmm.

    20. RB

      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 Helprin?

    21. TF

      Oh, no.

    22. RB

      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.

    23. TF

      Mm.

    24. RB

      Really smart. Wrote Soldier of the Great War, and A Winter's Tale, and Freddie and Frederica. I don't know if these, if you've heard of any of these books.

    25. TF

      No.

    26. RB

      But they are... There's a little bit of magic in them. Magic is a prime character in all these books.

    27. TF

      Mm-hmm.

    28. RB

      It's, it's luscious prose and epic stories of war and romance and exploration and relationships, and this latest one I highly recommend. It's a kind of on the edge of retirement, just under admiral or like a, a low-level admiral in the US Navy who almost becomes head of the DOD but doesn't get it 'cause he speaks his mind, and then he gets commissioned as a rebuke on this new weird ship. And I'll, uh, I'll just say that, and that's the setup for him taking this really c- more fast attack destroyer into the Middle East.

    29. TF

      Hmm.

    30. RB

      And deals with a lot of... He's kind of a war guy. He's a vet, and he's a pretty engaged political kind of, I'd call him an offensive realist in the John Mearsheimer-

  37. 2:06:09 – 2:09:58

    Rich's billboard.

    1. TF

      All right. This is the, the billboard question. If you could put anything on a billboard, message, quote-

    2. RB

      Yeah

    3. TF

      ... reminder, anything at all, obviously metaphorically, just to get something in front of a lot of people.

    4. RB

      [laughs] You asked this, so I did think about it a little bit.

    5. TF

      Yeah.

    6. RB

      And my initial response that I latched onto came from that movie Bowfinger. I don't know if you ever saw Bowfinger.

    7. TF

      No.

    8. RB

      It's a cult classic.

    9. TF

      Okay.

    10. RB

      And a lot of you people out there haven't seen it, but I highly recommend it.

    11. TF

      [laughs]

    12. RB

      It's Eddie Murphy tour de force.

    13. TF

      [laughs] Okay.

    14. RB

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

    15. TF

      [laughs]

    16. RB

      ... who thinks and in fact is being followed by people who are making a movie about him with him starring it, unbeknownst to him.

    17. TF

      [laughs]

    18. RB

      That's the setup. Steve Martin's directing. And he gets super pa- he's already a paranoid guy, but he gets super paranoid. He's like, "People are following me." [laughs] And he goes to a thing that, I don't know what kind of culty LA religion it's representing-

    19. TF

      Mm-hmm

    20. RB

      ... but it's called Mind Head.

    21. TF

      [laughs] Okay.

    22. RB

      Uh, and he goes in and he has his first counseling with the high priest of Mind Head.

    23. TF

      [laughs]

    24. RB

      And the religion is based on three happy premises. I'm not gonna remember them all, but happy premise number one was something like, "There is no giant foot in the sky about to step on me."

    25. TF

      [laughs]

    26. RB

      Okay, this is, like, a mantra-

    27. TF

      Yeah [laughs]

    28. RB

      ... 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.

    29. TF

      [laughs] Okay.

    30. RB

      Okay. That goes on my billboard. That or my favorite Burning Man bar ever had that giant neon sign on top of this kind of cozy geodesic dome playing groovy music decorated as an aquarium. Anybody out there-

  38. 2:09:58 – 2:11:42

    The importance of sabbaticals and disconnecting from digital devices.

    1. TF

      Have you taken any sabbaticals since Italy?

    2. RB

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

    3. TF

      [laughs] Now, are those failed retirements, or did those have an end point where you're like, "I'm gonna take a year, and then I'm gonna dust off my gloves and get back in the ring"?

    4. RB

      The Italy one was a failed one.

    5. TF

      [laughs]

    6. RB

      Although I suspected. I was really young, right?

    7. TF

      Yeah.

    8. RB

      The others, no, it's just been sabbaticals.

    9. TF

      Yeah.

    10. RB

      But-

    11. TF

      How long are they typically?

    12. RB

      You know, the Italy one was the longest one, but I've kind of built shelter into my, into our family's routine now.

    13. TF

      Mm-hmm.

    14. RB

      So it's just a part of the normal cycle of the seasons.

    15. TF

      Mm-hmm.

    16. RB

      And a really key component of that, not always achievable, especially now, Starlink and traveling Starlink and Starlink at my surf camp and Starlink on my Airstream.

    17. TF

      Mm-hmm.

    18. RB

      Like, it's harder and harder to disconnect, but disconnection is really-

    19. TF

      Mm-hmm

    20. RB

      ... 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, and when you watch the younger people, it's very unsettling for the first, it's only, like, three or four hours.

    21. TF

      Mm-hmm.

    22. RB

      And then when they realize it's over, it's total mean reversion to human behavior.

    23. TF

      Mm-hmm.

    24. RB

      Playing games, doing crafts, taking a hike, painting a picture.

    25. TF

      Yeah.

    26. RB

      It's totally beautiful what happens, and everybody is happy.

    27. TF

      Hmm.

    28. RB

      Well, you can't not be happy making a friendship bracelet or playing Taco Cat. What do we... Is that?

    29. TF

      [laughs] Okay.

    30. RB

      I don't want, I don't want to give that away.

  39. 2:11:42 – 2:13:09

    Taking up Procreate digital art during COVID.

    1. RB

      Tim.

    2. TF

      So nice to see you, man.

    3. RB

      It's great to see you.

    4. TF

      We've covered a lot of ground.

    5. RB

      It was fun. Wow.

    6. TF

      Uh-

    7. RB

      Oof

    8. TF

      ... where... If people want to learn more things [laughs] about Rich, should they be visitor 22 to your blog?

    9. RB

      No, I don't think so.

    10. TF

      [laughs]

    11. RB

      I think the, the blog is totally vestigial. It's an appendix that needs to be removed. [laughs]

    12. TF

      [laughs]

    13. RB

      Hopper and dropper. Yeah. No. I haven't written.

    14. TF

      Yeah.

    15. RB

      I haven't gotten the-

    16. TF

      Yeah.

    17. RB

      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-

    18. TF

      Yeah

    19. RB

      ... you know, business guy ego books, you know?

    20. TF

      Yeah. [laughs]

    21. RB

      I just don't find them very interesting.

    22. TF

      Mm-hmm.

    23. RB

      And I don't want to be one of those kind of jerk-offs.

    24. TF

      Maybe do a writer's retreat or an MFA, compressed MFA, and take a stab at fiction.

    25. RB

      It's not a bad idea.

    26. TF

      Just saying. Even if you never publish anything, it's a, it's a good muscle to-

    27. RB

      Yeah

    28. TF

      ... train for a bit, just to play with it.

    29. RB

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

    30. TF

      Yeah.

  40. 2:13:09 – 2:14:14

    Parting thoughts.

    1. TF

      Is there anything you would like to say? Any closing comments, formal public complaints you'd like to lodge?

    2. RB

      No, no. I guess I should just-

    3. TF

      [laughs]

    4. RB

      ... I should thank you. You know, you perform a good service. You provide a good service for a lot of people with this pod-

    5. TF

      Thanks, man

    6. RB

      ... and with your books, 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.

    7. TF

      Yeah.

    8. RB

      I do think people are just looking to lead better, happier, slightly more efficient-

    9. TF

      Yeah

    10. RB

      ... lives, improving lives. They want to improve themselves.

    11. TF

      Yeah.

    12. RB

      And you really help people do that, and the diversity of the guests that you bring on this pod is really ins- inspiring, so yeah, it's great. Thank you.

    13. TF

      Thanks, man.

    14. RB

      It's great to be here.

    15. TF

      Yeah. Awesome to have you.

    16. RB

      Yeah.

    17. TF

      Everybody listening, we're gonna include everything we talked about in the show notes, tim.blog/podcast. If you search Barton, that's gonna be the only Barton, so you'll find [laughs] 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

Episode duration: 2:14:25

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