The guest
Rich Barton: Serial entrepreneur and investor who founded Expedia (incubated inside Microsoft), Zillow, Glassdoor, and Avvo, and sits on the boards of Netflix and others; known for 'provocation marketing' and building consumer-facing digital marketplaces.
What this episode covers
Rich Barton walks Tim Ferriss through his career arc from a Stanford engineer and reluctant management consultant to a product manager at Microsoft, where Bill Gates green-lit and funded Expedia as an internal venture before spinning it out during the late-1990s internet bubble. He explains the strategy and HR logic behind spinning companies out, how he pitched employees, spouses, and investors, and the eventual sale of Expedia to Barry Diller's IAC. Barton details how he and co-founder Lloyd Frank started Zillow around the insight that home values should be public, leading to the provocative Zestimate, and codifies his 'provocation marketing' playbook used across Zillow, Glassdoor, and Avvo. He also covers company-naming rules, how to evaluate board seats, hiring and firing people, and a mid-career health reckoning during his wife's high-risk twin pregnancy that reshaped his priorities around family, fitness, and disconnection.
Recommended on this episode
MediaRecommended
CNBC
“It's my favorite source of news”
“It's my favorite source of news because business news is generally happy. Yeah. Got it. They just don't wallow in the”— Rich Barton
ProductRecommended
Pocari Sweat
Otsuka Pharmaceutical
“My favorite electrolyte is picari sweat ... My nutritionist says that's the one”
“My favorite electrolyte is picari sweat. Japanese one. Oh, the blue can. My nutritionist says that's the one.”— Rich Barton
ProductRecommended
Hyperice Venom (back)
Hyperice
“Oh my god. That loosens everything up, too”
“I'm wearing that Venom. Oh my god. That loosens everything up, too. I have it on repeat. I'm wearing that Venom.”— Rich Barton
BookRecommendedISBN verified
eBoys
Randall E. Stross
“it was incredibly inspirational. Super entertaining”
“a book was recommended to me called E Boys. it was incredibly inspirational. Super entertaining and so entertaining.”— Tim Ferriss
ProductRecommended
Peloton
Peloton
“the Pelaton is my favorite one there”
“My knees kind of are not great running, but a softer treadmill works, but the Pelaton is my favorite one there.”— Rich Barton
BookRecommendedISBN verified
The Oceans and the Stars
Mark Helprin
“this latest one I highly recommend”
“Recently, I gifted The Oceans and the Stars. Do you know Mark Hellprin? this latest one I highly recommend.”— Rich Barton
BookRecommendedISBN verified
Winter's Tale
Mark Helprin
“It's just a beautiful, beautiful story ... You might actually like it”
“The only one of his that I've probably reread is A Winter's Tale ... It's just a beautiful, beautiful story of early 20th century life”— Rich Barton
BookRecommendedISBN verified
Polostan
Neal Stephenson
“his latest Polo Stump, I highly recommend”
“Neil Stevenson ... his latest book Polaron. But his latest Polo Stump, I highly recommend.”— Rich Barton
BookRecommendedISBN verified
Cryptonomicon
Neal Stephenson
“Kryptonomicon or something like which I loved”
“It's not like Kryptonomicon or something like which I loved. Side note, me too.”— Rich Barton
BookRecommendedISBN verified
Stories of Your Life and Others
Ted Chiang
“pretty much everyone who read it was just like I don't understand how this guy does this”
“Ted Chang ... has two collections of short stories ... It's like stories of your life and other stories. one of those short stories was the basis for the movie Arrival”— Tim Ferriss
MediaRecommended
Arrival
“Jeremy Rener, amazing movie”
“one of those short stories was the basis for the movie Arrival with Jeremy Rener, amazing movie.”— Tim Ferriss
BookRecommendedISBN verified
Exhalation
Ted Chiang
“the second is just unbelievably good ... the ones that hit are just incredible”
“Then a second collection came out, Exhalation ... And the second is just unbelievably good.”— Tim Ferriss
BookRecommendedISBN verified
The Paper Menagerie and Other Stories
Ken Liu
“in this really compelling way ... So highly highly recommend”
“Kenneth Leu ... has the paper managerie ... blends or alternates in a sense between sci-fi and fantasy in this really compelling way. highly highly recommend.”— Tim Ferriss
BookRecommendedISBN verified
The Lincoln Highway
Amor Towles
“it is such a page turner. It's so beautifully architected”
“Lincoln Highway, which I mean, it is such a page turner. It's so beautifully architected.”— Tim Ferriss
MediaRecommended
Bowfinger
“It's a cult classic ... I highly recommend it”
“that movie Bow Finger ... It's a cult classic ... I highly recommend it. It's Eddie Murphy Tour to Force.”— Rich Barton
ProductRecommended
Procreate
Savage Interactive
“There's something very soothing about it”
“I took a Procreate painting on my iPad during co and it's so I'm so I feel so good.”— Rich Barton
ProductRecommended
Taco Cat (Taco Cat Goat Cheese Pizza)
Dolphin Hat Games
“That is a funny game ... So fun. That was so good”
“Taco Cat. That is a funny game, isn't it? So stupid. So fun. That was so good.”— Rich Barton
The guest's own work
ProductBy the guest
Expedia
Rich Barton
“Expedia was a v quote venture startup inside of Microsoft and then it spun out and we can get to that.”— Rich Barton
ProductBy the guest
Zillow
Rich Barton
“that was the dawn of Zillow. We're basically building a super app, a one-stop shop application for anybody who's renting or buying”— Rich Barton
ProductBy the guest
Glassdoor
Rich Barton
“having data like having a stream of data that people are interested in at Glass Door, which I did with Bob Hman ... is another example of that.”— Rich Barton
Also referenced (named, not recommended)
ProductReferenced
iPad
Apple
“I've got my iPad set up next to it rolling, you know, CNBC quietly. Mhm. On mute.”— Rich Barton
ProductReferenced
iPhone
Apple
“now I have a folder called the Breakfast Club, my iPhone pictures, and I have like a thousand pictures”— Rich Barton
BookReferenced
DOS for Dummies
IDG Books
“the book that the dummies series was founded on was DOSs for dummies. it was like the bestselling book about software of all time.”— Rich Barton
ProductReferenced
MS-DOS 5
Microsoft
“We were working on MS DOS5 ... it was a really big operating system for Microsoft at the time and we made an upgrade”— Rich Barton
ProductReferenced
Windows 95
Microsoft
“this was during the Windows 95 launch. I left the Windows 95 team and I went to the consumer division at Microsoft”— Rich Barton
ProductReferenced
Windows NT
Microsoft
“He also liked that we could rebuild all the mainframes on Windows NT which was a different conversation.”— Rich Barton
ProductReferenced
Microsoft Encarta
Microsoft
“these things were like Wikipedia before Wikipedia was called In Carta. Multimedia CDROM”— Rich Barton
ProductReferenced
Microsoft Office
Microsoft
“as long as Windows NT the operating system succeeded or Office Microsoft Office succeeded they could make a lot of money”— Rich Barton
ProductReferenced
easySABRE
Sabre
“I demoed Easy Saber on Prodigy. Easy Saber was a tool for travel agents to use at home on Prodigy to access the airline reservation systems.”— Rich Barton
ProductReferenced
Prodigy
“I demoed Easy Saber on Prodigy. Prodigy was an online service. and I could get access to it on Prodigy.”— Rich Barton
ProductReferenced
Hotels.com
“they kind of pushed us to buy the number two player which was Hotels.com. And so we mashed those things together”— Rich Barton
ProductReferenced
Match.com
IAC
“I think he owns most of the popular dating apps ... and then spun it out as Match.com”— Tim Ferriss
ProductReferenced
Netflix
“Including the IA board, which had bought Expedia, and Netflix, where I'd been on the board since like 2000”— Rich Barton
ProductReferenced
Uber
“I was one of the first three advisers when it was called Uber Cab LLC. Way back in the day.”— Rich Barton
ProductReferenced
Dropbox
“He went off on one that was kind of Dropbox before Dropbox is like it was obvious that the kind of cloud storage thing was going to be huge.”— Rich Barton
ProductReferenced
Google AdWords
“The magic business model that they sort of discovered ... was the AdWords, you know, the digital auctionbased market.”— Rich Barton
ProductReferenced
AWS
Amazon
“So, at the time, was it just rentable infrastructure, AWS? AWS didn't exist.”— Tim Ferriss
ProductReferenced
TripAdvisor
“It was just kind of like Trip Adviser for attorneys. You kind of trip adviser for anything, right?”— Rich Barton
MediaReferenced
Die Hard
“did you see Die Hard? You remember Die Hard where the the German terrorist leader ... he said, Ladies and gentlemen, I'll give you the FBI.”— Rich Barton
ProductReferenced
Stripe
“the forever startups now, like I'm sure Stripe directors make a lot of money.”— Rich Barton
ProductReferenced
WordPress
Automattic
“Matt Mullenweg, generally associated with WordPress, founder and CEO of Automatic ... and pioneer of distributed workforces.”— Tim Ferriss
ProductReferenced
Shopify
“And there are some other standout examples. I mean, Shopify did really well. Yep.”— Rich Barton
ProductReferenced
Kindle
Amazon
“I have gifted Oceans and Stars, but I'm such a Kindle person and so many of us are digital readers now.”— Rich Barton
BookReferencedISBN verified
A Soldier of the Great War
Mark Helprin
“a beautiful, luscious pros writer, really smart, wrote Soldier of the Great War and A Winter's Tale and Freddy and Frederica.”— Rich Barton
BookReferencedISBN verified
Freddy and Fredericka
Mark Helprin
“wrote Soldier of the Great War and A Winter's Tale and Freddy and Frederica.”— Rich Barton
BookReferencedISBN verified
The Last of the Mohicans
James Fenimore Cooper
“I read Last of the Moheakans just to beautiful. It's beautiful. Take a walk through that area in that time period.”— Tim Ferriss
BookReferencedISBN verified
Snow Crash
Neal Stephenson
“He's the one who wrote Snow Crash. Oh yeah. Okay. So you know him. Snow Crash.”— Rich Barton
ProductReferenced
Starlink
SpaceX
“Starlink and traveling Starlink and Starlink at my surf camp and Starlink on my Airstream like it's harder and harder to disconnect”— Rich Barton
ProductReferenced
Airstream
Airstream
“Starlink at my surf camp and Starlink on my Airstream like it's harder and harder to disconnect”— Rich Barton
Big reveals from this episode
- Barton pitched Bill Gates on Expedia as a travel-first, software-second company and Gates became his 'first venture capitalist,' green-lighting and funding it inside Microsoft rather than letting him build it outside.
- Expedia spun out of Microsoft taking 150 people who were given the choice to stay or leave; all but two came along, and Barton framed the spinout to Steve Ballmer largely as an HR and talent-retention experiment.
- On IPO night in November 1999, Barton's wife Sarah went into labor and joked about whether the baby would have to be named Expedia; his son Will was born while the IPO was happening.
- Zillow began when co-founder Lloyd Frank got fired from Expedia and convinced Barton not to move to California; they dusted off an old Microsoft-era plan for a digital real estate marketplace built on the insight that home prices were kept opaque.
- The Zestimate emerged from a failed attempt to auction homes online; the killer feature became an algorithmic value on every roof, displayed like a stock chart, after they realized auctions require a real-time liquid market.
- Zillow launched on a 'server in a closet' that crashed under day-one traffic after Walt Mossberg praised it; the team turned the failure into press with a 'house porn site' headline in the San Francisco Chronicle.
- Bill Gurley, a Zillow board member, challenged the team to imagine having no marketing budget, which pushed Barton to develop his 'provocation marketing' playbook of building provocative, data-driven, talk-worthy features instead of buying ads.
- A six-week scare when Sarah went into early labor with twins at 27 weeks triggered Barton's reassessment of his work-all-the-time lifestyle and his decision to prioritize health and family and eventually leave the Expedia CEO role.
Worth remembering
- Barton's daily pre-workout smoothie includes oat milk, ice, two-thirds of an apple, pistachios, macadamia, blueberries, and Pocari Sweat electrolyte, plus a prune to 'keep things moving.'
- He wears a Hyperice Venom heated, vibrating back wrap for his roughly 45-minute morning kitchen-table routine to loosen up.
- As a young Microsoft PM, Barton bundled the MS-DOS 5 upgrade with 'DOS for Dummies' to sell through Barnes & Noble and Borders; it flopped because the $49-$54 product looked like a $12 book.
- Microsoft took 17 years to regain its November 1999 stock price after the dot-com crash, while Expedia recovered its all-time high within a couple of years.
- Barton's idea criteria are 'big pond, good fishermen' plus a big obvious consumer problem, and he warns entrepreneurs against big problems that are actually small markets.
- Glassdoor's 'give to get' model required users to share their own salary, title, and company review to unlock seeing others' data.
- Barton compares Avvo's lawsuit-courting launch strategy for rating attorneys to the Die Hard line 'I'll give you the FBI', deliberately inviting the suits to create noise.
- His company-naming rules: use rare high-Scrabble-point letters (Z, X, Q), few syllables, evocative meaning, verb-able, and ideally a good 'dog name', hence Zillow.
- Greg Maffei's three-part board-seat filter that Barton uses: is it local, is it fun, is it lucrative, aim for at least two of three.
- Barton's billboard message is 'Don't panic', inspired partly by the movie Bowfinger's mantra 'even though I feel like I might ignite, I probably won't' and a Burning Man dome's neon sign.
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