Tim FerrissHow Rich Barton Built Expedia and Zillow — Audacious Goals, Provocation Marketing, and More
CHAPTERS
- 0:00 – 1:32
IPO-day childbirth story and noticing “magic” in products
Rich Barton opens with a personal story about his first child being born on the day of Expedia’s IPO, including a joke about naming the baby “Expedia.” He then shifts to a moment of product delight, describing how Apple’s ecosystem made his mouse seamlessly move to an iPad screen—prompting him to text Eddy Cue about the “magic.”
- •Describes the coincidence of IPO day and his son’s birth, plus the “name him Expedia” joke
- •Mentions knowing Eddy Cue and enjoying observing standout product experiences
- •Recounts discovering seamless cross-device behavior that felt like “magic”
- •Emphasizes how small product moments can create outsized emotional impact
- 1:32 – 2:34
Why CNBC is his default news feed
Tim asks why Rich keeps CNBC on in the background, and Rich explains it’s his preferred way to stay informed. He says business news is generally more upbeat and less emotionally draining than general news, and he often watches with captions on mute.
- •Prefers business news because it tends to be “happy” and less demoralizing
- •Uses CNBC largely as a background information stream
- •Watches on mute with closed captions and only turns attention to items that stand out
- •Notes the channel can become repetitive, but includes strong interviews
- 2:34 – 6:38
Morning routine: early start, smoothie ingredients, and pre-workout setup
Rich walks through his early-morning routine, describing quiet time before his wife is up and how he catches up via email and an iPad news stream. He details his smoothie and a few specific pre-workout practices, including using a heated/vibrating back wrap.
- •Typically wakes around 6:30 and values uninterrupted morning time
- •Uses email as his primary “newsfeed” and pairs it with the iPad for news
- •Lists smoothie ingredients and mentions Pocari Sweat as his preferred electrolyte
- •Uses a Hyperice “Venom” back device as part of his morning routine
- •Works out nearly every day to feel mentally settled and focused
- 6:38 – 9:12
Skepticism about extreme longevity optimization—and the “Breakfast Club” parenting ritual
The conversation turns to longevity culture, with Rich expressing skepticism about aggressively pushing supplements and tightly scheduled optimization. He then shares how his role as the early-rising parent led to daily breakfast-making for his kids, including building a photo time series he treasures.
- •Says pushing hard on longevity often leads to “pushback” and diminishing value
- •Frames health basics as more important than stacking endless interventions
- •Describes being the morning parent who made whatever breakfast the kids wanted
- •Shares the story of feeding a child impacted by appetite-suppressing medication
- •Kept candid daily breakfast photos in an album called “The Breakfast Club”
- 9:12 – 11:32
Brad Chase at Microsoft: permission to swing big and fail
Rich explains how his early Microsoft boss, Brad Chase, shaped his willingness to take big risks. He tells a story about a bold project that failed and highlights how supportive leadership can encourage innovation rather than punish failure.
- •Introduces Brad Chase as an early mentor and boss at Microsoft
- •Describes Microsoft’s product management culture at the time
- •Explains how Brad encouraged a large “swing” even though it failed
- •Highlights the value of leaders asking, “What’s your next big idea?” after failure
- •Raises the broader question of how companies enable innovation without chaos
- 11:32 – 16:08
The “DOS for Dummies” bundle failure—and what it taught him about innovation culture
Rich recounts a packaging and distribution experiment bundling MS-DOS upgrades with a “DOS for Dummies” book for bookstores. The unit economics and customer expectations didn’t match, and it flopped—yet he emphasizes the organizational lesson: strong cultures don’t punish principled experiments.
- •Tried bundling software with a popular book to sell via bookstores
- •Explains the pricing mismatch and confusion about what customers were buying
- •Calls out cost-of-goods issues and the “shock value” of a higher price tag
- •Says great organizations support big swings and avoid reflexive punishment
- •Uses the story to underline how innovation depends on leadership behavior
- 16:08 – 20:22
From consulting to Microsoft: discovering he’s a “builder,” not a “server”
Rich describes taking a strategy consulting job after Stanford and quickly realizing it wasn’t the right fit. He explains his “clients and servers” worldview—where he discovered he wanted to build products rather than advise from the outside—then credits a friend for nudging him toward Microsoft.
- •Took a strategy consulting job and learned quickly it wasn’t aligned with his nature
- •Says consulting taught him strategy fundamentals but lacked “seeing it through”
- •Explains the “clients and servers” continuum and identifying as a builder/client
- •Credits a Stanford friend for repeatedly encouraging him to join Microsoft
- •Describes arriving at Microsoft as being “a kid in a candy store”
- 20:22 – 29:54
How Expedia began inside Microsoft—and why it spun out
Rich explains that Expedia started as an internal venture at Microsoft, sparked by insights about consumer access to travel booking tools. He describes pitching the opportunity to Bill Gates, later arguing to spin the business out, and positioning the spinout partly as a talent and accountability experiment.
- •Expedia originated as a venture-style project inside Microsoft
- •Initial travel concept evolved from CD-ROM travel guides to consumer booking access
- •Pitched a vision of becoming the world’s largest seller of travel
- •Explains why spinning out can unlock value and attract a focused investor base
- •Frames the spinout pitch as an HR/accountability mechanism within a large company
- 29:54 – 38:00
Recruiting the spinout team and the IPO high point
Rich describes pitching the adventure of the Expedia spinout to employees, noting the toughest audience was often their spouses. He also shares the roadshow intensity and returns to the IPO-day birth story as a personal peak moment.
- •Recruited people who were “adventurers” and likely to leave otherwise
- •Says spouse skepticism required detailed, dinner-table explanations
- •Describes the IPO roadshow format: many cities and meetings over weeks
- •Notes Expedia had a real business model and recovered faster than broader tech declines
- •Calls the IPO-day birth of his son a defining high point
- 38:00 – 44:06
Selling to Barry Diller/IAC and taking a sabbatical in Florence
Rich explains how the acquisition by Barry Diller’s IAC came together, including the role of IAC’s corporate development thinking and Microsoft’s willingness to sell. After stepping aside, he describes moving his family to Florence for a year, reconnecting with study, art, and a different pace of life.
- •Describes IAC’s interest in building an interactive conglomerate
- •Mentions Dara Khosrowshahi as a key figure involved in the acquisition strategy
- •Explains the two-step nature of the deal and later consolidation moves
- •Says the transaction taught him he wanted to control companies he started going forward
- •Moved to Florence post-sale for school, art, biking, and the “Italy vibe”
- 44:06 – 49:08
From post-Expedia brainstorming to founding Zillow with Lloyd Frink
Back in Seattle, Rich describes considering venture capital before being pulled into brainstorming with Lloyd Frink. They revisit ideas from earlier research and focus on the frustration of opaque real estate data, framing Zillow as a “power to the people” move for home information.
- •Describes uncertainty about starting another company due to workload and life priorities
- •Brainstormed with Lloyd Frink after Lloyd left Expedia
- •Considered an early cloud-storage-like idea but worried it wouldn’t be profitable
- •Revived the digital real estate marketplace concept and targeted industry opacity
- •Positioned Zillow as consumer empowerment through access to information
- 49:08 – 56:40
Zillow’s early mistakes, the “big pond” test, and discovering the Zestimate
Rich explains the criteria he uses to choose opportunities—especially “big pond, good fishermen”—and warns that some big problems are still small opportunities. He then details Zillow’s early attempt to auction homes, why it didn’t work, and how that exploration led to the Zestimate as a breakthrough feature.
- •Uses “big pond, good fishermen” as a primary business filter
- •Notes many entrepreneurs misjudge opportunity size even when the problem feels large
- •Tried a home-auction concept and learned housing markets aren’t real-time liquid markets
- •Highlights the difficulty of changing deeply ingrained consumer behavior
- •Describes wanting “prices on every roof” and building toward the Zestimate concept
- 56:40 – 1:06:07
Launch-day chaos, provocation marketing, and handling regulatory pushback
Rich recounts Zillow’s launch-day traffic surge and server failure, then describes turning that failure into positive press. He lays out how provocative features and data distribution can substitute for ad spend, and he explains how product popularity can help neutralize industry lobbying and regulatory resistance.
- •Launch drove massive traffic after influential coverage, overwhelming infrastructure
- •Marketing leadership reframed the outage as “lemonade from lemons” PR
- •Describes “provocation marketing” as building features that spark emotional discussion
- •Explains building PR/data pipelines to feed constant housing-news demand
- •Says regulatory/lobbying battles were countered by activating broad user and legislator support
- 1:06:07 – 1:12:24
Glassdoor and Avvo: ‘give to get’ data models and lawsuits as attention engines
Rich expands provocation marketing with examples from Glassdoor and Avvo. He explains Glassdoor’s “give to get” approach to collecting salary and workplace reviews, then discusses Avvo’s attorney ratings, anticipating lawsuits, and why early legal challenges were manageable and even catalyzed awareness.
- •Glassdoor used salary transparency as inherently provocative data
- •Explains the “give to get” mechanic to solve user-generated data collection
- •Added company and CEO reviews as additional provocative elements
- •Avvo rated attorneys and expected legal action as part of the launch dynamic
- •Says early wins reduced the momentum of continued lawsuits
- 1:12:24 – 1:22:18
Marketplace defense: brand strength, workflow integration, and naming memorable companies
Rich discusses how SEO-driven middleman models can be disintermediated—especially when dependent on a single traffic supplier—and describes defensive strategies. He then shares his company-naming framework, arguing for invented words and explaining the specific attributes he looks for in a name.
- •Explains strategic risk of heavy dependence on a single customer source like Google
- •Describes Google moving “vertical” into reviews, travel, and other categories
- •Defends with two moves: build a direct-traffic brand and embed into transaction workflows
- •Shares preference for invented words to own brand meaning
- •Outlines naming rules: distinctive letters, fewer syllables, positive evocation, verb potential, and memorable word forms (e.g., double letters/palindromes)
- 1:22:18 – 1:34:08
Benchmark, board service, and leadership systems (including firing well)
Rich explains why he worked with Benchmark as a venture partner and what he gained from staying close to new ideas and company-building. He then demystifies board roles, shares criteria for choosing boards, and transitions into leadership practices like disappearing for two weeks to develop successors and approaching firing as a mutual win.
- •Took a venture partner role to stay connected to Silicon Valley deal flow and ideas
- •Describes boards as coaching and company-building in private companies, with different dynamics in public ones
- •Shares board selection heuristic: “Is it local? Is it fun? Is it lucrative?”
- •Recommends leaders periodically disconnect for two weeks to force leadership emergence
- •Discusses hiring signals (interest/passion) and firing quickly, framing it as helping both sides find fit
- 1:34:08 – 2:14:25
Health catalyst, training routine, family tattoo, distributed work, reading picks, and ‘Don’t panic’
Rich describes a personal health-and-family catalyst during a high-risk twin pregnancy that reshaped his priorities and habits over time. He shares his current fitness mix, discusses a family tattoo design, reflects on remote work benefits post-pandemic, recommends fiction authors/books, and ends with a billboard message focused on staying calm and disconnecting periodically.
- •Recounts the scare during his wife’s twin pregnancy and how it triggered a lifestyle reassessment
- •Describes evolving health habits: yoga, running, later weight training, plus ongoing activity to keep doing sports he loves
- •Outlines a current routine combining cardio/zone-2-style work, lifting, and play sports
- •Explains the symbolism and collaborative design process behind the family tattoo
- •Supports distributed work as more inclusive, citing influence from a distributed-company leader he brought into a company meeting
- •Shares fiction recommendations and reading as a way to quiet “monkey brain”
- •Billboard message centers on calm: “Don’t panic,” and the value of disconnecting/sabbaticals
