#806: How Rich Barton Built Expedia and Zillow from $0 to $35B — Audacious Goals, Provocation Marketing, Scrabble for Naming, and Powerful Daily Rituals
The myth-busts, hot takes, explainers, and tools worth keeping.
◆Hot Take· 1
◆Hot Take1:51:30
Don't Wait for a Crisis to Prioritize Family and Health
Barton argues that there is never a perfect time to have children and that people should not wait for an external shock before protecting family life and personal health. He views modern flexible work as an opportunity to interweave work and life more effectively than earlier office norms allowed.
He rejects the idea that a clearly better time for children will arrive
Parenthood broadens attention beyond personal wants
External health catalysts eventually force neglected priorities into view
Confidence and flexible work can support a healthier integration
“there's never a better time like there's never a good time”
“don't wait for an external catalyst to make sure you're prioritizing your family life and your personal health”
#family#health#parenting#work life
❝Story· 6
❝Story07:00
A Thousand Breakfast Photos Became His Most Prized Possession
When his children lived at home, Barton became their early-morning short-order breakfast cook and used the time to feed them and connect. He also took candid photos most mornings, creating a time series called the Breakfast Club that shows the children growing up.
He made whatever breakfast each child requested
The routine created quality time regardless of the children's mood
He quietly captured candid photos rather than posed portraits
The resulting folder contains roughly a thousand pictures
“I took a picture most days. Okay. Totally candid. There no no posing. I would sneak a picture every day.”
“it's a virtual possession, but it's my most prized possession.”
#family#parenting#rituals#photography
❝Story11:00
Microsoft Answered a Costly Failure With One Question
As a young Microsoft product manager, Barton created a DOS for Dummies software bundle for bookstores that failed because its price and packaging did not fit shoppers' expectations. Expecting punishment, he instead heard his boss Brad Chase ask for his next big idea, which Barton presents as evidence of an innovation-supporting culture.
The bundle paired an MS-DOS upgrade with DOS for Dummies
Its roughly $49 to $54 price shocked shoppers expecting a $12 book
The packaging failed to make the included software clear
Brad Chase did not punish the failed swing
“great organizations encourage innovation, encourage big idea people to take big swings and do not punish them when it doesn't work out according to plan.”
“all right what's your next big idea”
#innovation#failure#microsoft#culture
❝Story41:30
Expedia's IPO Happened While Barton's Son Was Born
After ending Expedia's heavily subscribed road show a day early, Barton returned to Seattle just before his pregnant wife went into labor. Their son was born while Expedia went public, combining the company's high point with the birth of Barton's oldest child.
The road show covered 15 cities over three weeks
Investor demand had filled the book many times over
Barton returned home only hours before labor began
His wife joked about a promise to name the baby Expedia
“Honey, this is like IPO day. If our baby is born on the IPO day, do I really have to name him Expedia?”
“while the IPO was happening, my son was being born.”
#expedia#ipo#family#entrepreneurship
❝Story54:00
A Failed Home Auction Produced Zillow's Killer Feature
Zillow initially tried to auction homes as a more efficient price-discovery mechanism. The experiment revealed that housing lacked the liquid real-time market auctions require and that radically retraining buyers was too heavy a lift, but the search for price discovery produced the Zestimate concept.
Home auctions lacked simultaneous bidder liquidity
The proposed buying behavior was not simple or ten times better
The team wanted an estimated price displayed on every roof
Home values were presented visually like stock charts
“to have an auction work, you kind of need a real-time liquid market.”
“in pursuit of price discovery, we found this estimate, which was our killer our killer feature.”
While Barton was running Expedia and working constantly, his wife's high-risk twin pregnancy led to a frightening six-week hospital period. Although the children were born healthy, the experience made him reassess his priorities, leave the CEO lifestyle, and gradually build a stronger physical and mental foundation.
His wife entered early labor around 27 weeks
She remained hospitalized for roughly six weeks
Barton was simultaneously caring for their three-year-old son
He later explored road biking, hot yoga, running, and strength work
“it got me to just reassess my life and how I led my life and what my priorities were”
“If I wanted to do the things I love to do for the long term, I was going to have to really build my foundation.”
#health#family#priorities#fitness
❝Story2:10:00
What Happens After Young People Lose Connectivity
Barton builds periods of shelter and disconnection into his family's normal seasonal rhythm. On a Grand Canyon rafting trip, he watched younger people move from a few unsettled hours without connectivity into games, crafts, hiking, painting, and visibly happier human interaction.
Disconnection is a central feature of Barton's sabbaticals
The first three or four hours can feel unsettling
Acceptance produces what he calls mean reversion to human behavior
Shared offline activities replace phone attention
“it's total mean reversion to human behavior. Playing games, doing crafts, taking a hike, painting a picture.”
“It's totally beautiful what happens. And everybody is happy.”
Use the Interests Section to See a Candidate's Real Spark
Barton distrusts polished interviewing and conflicted reference checks, so he uses a candidate's listed interests to invite unscripted conversation. He watches for genuine passion and has used the interest as a starting point for an impromptu business case.
The bottom interests section is his favorite part of a resume
Candidates should be able to light up about an interest they chose to list
Follow-up questions reveal energy beyond rehearsed job answers
A related market-sizing case can test thinking in a more natural context
“I want to get somebody in an interview situation talking about their interests”
“I want to find people who are passionate people.”
#hiring#interviews#passion#talent
▲Takeaway· 5
▲Takeaway02:30
Rich Barton's Morning Reset Before Work
Barton describes an early routine built around quiet news and email, a smoothie, coffee, heat and vibration on his back, and a near-daily workout. He says the sequence helps him feel settled and get his mind working before the rest of the day.
He usually rises at 6:30 and gets up before his wife
He catches up on email while CNBC runs muted with captions
He uses the Hyperice Venom during part of the kitchen-table routine
He says he cannot get his mind right without a workout
“I need to get things going and feel settled a little bit. Settled and brain on before I work out.”
“pretty much every day I do a workout. I can't really get my mind right without that.”
#morning routine#exercise#focus
▲Takeaway19:00
The Career Divide Between Builders and Service Providers
Barton realized during consulting that he preferred building the client's product to advising across many clients. He frames careers as a continuum between service provision, which offers varied problems, and building, which provides ownership through the finished product.
Service professions offer curiosity and varied client problems
Consultants often do not see work through to the finished product
Barton felt more drawn to what clients were building
The realization led him toward Microsoft product work
“I derived my jollies on the other hand from being a builder and the client.”
“I wanted to build things. I derived my jollies that way.”
#career#builders#consulting#self-knowledge
▲Takeaway1:46:00
How Barton Approaches Firing With Courage and Heart
Barton says leaders commonly leave a poor fit in place too long and should handle separation face to face rather than by text. He recommends seeking aligned interests, listening without argument, helping the person find a better fit, and asking for useful feedback on the way out.
Do not postpone a separation while hoping performance fixes itself
Hold the conversation face to face
Recognize the power imbalance and absorb the person's reaction
Listen sympathetically without arguing
Use a casual exit conversation to learn about the organization
“All of my mistakes as a leader have been leaving almost all of them have been leaving the pitcher on the mound too long hoping…”
“as the person holding power in this situation, you have to wear it.”
#firing#leadership#feedback#management
▲Takeaway1:57:00
Why Barton Reads Fiction Instead of Business Books
Barton reads fiction to escape the operational alertness of business life and relax what he calls his monkey brain. He especially values beautiful prose, science fiction, and magical realism, recommending writers including Mark Helprin, Haruki Murakami, and Neal Stephenson.
He increasingly avoids nonfiction business books
Fiction provides release from quick-twitch operational thinking
He recommends The Oceans and the Stars and A Winter's Tale
He also recommends Neal Stephenson's Polostan
“to get my monkey brain to relax escaping into a fiction novel for me is just a fantastic release”
“I really love beautiful beautiful fiction.”
#books#fiction#reading#recovery
▲Takeaway2:06:00
Don't Panic: Barton's Message for High-Beta Moments
For his metaphorical billboard, Barton chooses 'don't panic.' He sees part of a leader's job as calming fear and mood swings, creating a healthier community by encouraging people to breathe before reacting, texting, or becoming outraged.
His alternate phrase is that feeling ready to ignite does not mean ignition will happen
Fear and panic are common but events are usually manageable
A pause can improve family, community, and leadership reactions
Modern news and social feeds amplify anger, fear, and outrage
“Don't panic.”
“People have a tendency towards fear and panic. And almost always it's going to be just fine.”