Rich Barton could hear the keyboard. Somewhere at the other end of a telephone, a travel agent was looking at fares, routes and schedules. Barton was trying to arrange a complicated business trip. The useful information was on a screen. The screen belonged to somebody else.
He later described wanting to reach through the telephone and turn it around. There is a whole career in that small act of impatience. Expedia would let travelers inspect their choices. Zillow would put estimated prices on houses. Glassdoor would let employees compare what working somewhere actually paid, and what it felt like. In each case, a familiar arrangement suddenly looked rather peculiar: why should the person making the decision be the person with less information?
Barton calls the connecting idea “power to the people.” It sounds large enough to require a balcony. His applications have tended toward the practical: a plane ticket, a home, a job. These are decisions people make with their own money and live with afterward. A little more knowledge changes the conversation.
The screen on the other side of the telephone
Born in 1967 and raised in New Canaan, Connecticut, Barton graduated from Stanford in 1989. After consulting at Alliance Consulting Group, he joined Microsoft in 1991. His early assignment was product management for MS-DOS, software whose name now gives a person's age away almost as efficiently as a birth certificate.
Microsoft also gave him room to be wrong. Barton tried bundling an MS-DOS 6 upgrade with DOS for Dummies for sale through Barnes & Noble. The idea left the company holding millions of dollars in inventory. His boss, Brad Chase, responded by asking, “What’s your next idea?” Barton remembered the permission as much as the failure. An employer had absorbed an unsuccessful experiment without treating the experimenter as finished.
The travel idea began inside Microsoft in 1994. When Barton pitched an electronic travel agency to Bill Gates, the company offered a place to build it. Expedia reached the web on October 22, 1996. Consumers could search flights, hotels and rental cars, make reservations, and pay online. The service connected to the WORLDSPAN reservation system that travel professionals used.
The original product included travel guides, hotel maps and software wizards that walked customers through unfamiliar choices. Its hotel directory covered more than 25,000 properties. That combination mattered: access alone was insufficient if the information remained incomprehensible. People needed a way to use it. The travel agent's screen had to become a consumer's tool.
There was a nicely transitional detail in the launch: tickets could still arrive by mail. The purchase had entered the internet age; the envelope had retained its employment. Expedia also supported electronic tickets, letting customers move between two systems that were, for a while, operating together.
A public company, then a pause in Florence
Expedia went public in 1999, with Barton as president and chief executive. Building a travel brand required spending beyond the habits of a software division. He recalled asking Steve Ballmer for $100 million for television advertising; the request helped push the conversation toward a separate company. The IPO offered capital and independence.
He remained through 2003, when IAC acquired the company. His next move was a year in Florence with his wife, Sarah, and their three children. Italy already occupied a particular place in his life. As a Stanford undergraduate, studying in Florence had interrupted the sequence of his industrial engineering program. He ended up designing a general engineering degree focused on industrial economics.
Returning with a family made the city a different kind of classroom. He tried drawing and writing, entertaining the possibility of another direction. Business ideas kept arriving anyway. A sabbatical, it turned out, could remove the meetings more easily than the habit of spotting a business.
Back in Seattle, he began working with Lloyd Frink, a friend and fellow Microsoft and Expedia veteran. Their next subject was the house. Home shopping offered plenty of expensive decisions and remarkably awkward access to the information needed to make them. Barton had found another screen that needed turning.
Forty million invitations to be curious
Zillow was incorporated in December 2004. The website launched on February 8, 2006, publishing Zestimates for approximately 40 million American homes. A visitor could look up a property even when it wasn't for sale. The question had escaped the transaction.
That was a consequential product choice. Most people are only occasionally buying a home. Curiosity about the place next door is considerably less seasonal. Giving a number to an otherwise private-looking asset made property data something people could inspect, discuss and dispute. Dinner conversation acquired an additional hazard.
Barton set an early communications goal of a million monthly visitors within six months, with no marketing spending. He later wrote that Zillow reached a million visitors in its first three days and that the site crashed during its first week. The actual interest had arrived faster than the machinery could comfortably accommodate.
Investor Bill Gurley's challenge to imagine a company without an advertising budget helped shape that approach. Zillow could produce information that people wanted to talk about and newspapers wanted to cover. Its home values supplied a continuing subject, rather than a single launch announcement. Barton eventually called the approach provocation marketing.
A Zestimate also came with a boundary. It was an automated estimate of market value, rather than an appraisal or an agreement between buyer and seller. Its usefulness lay in giving people somewhere to begin. A number can open a discussion without having the authority to settle it.
“What’s your next idea?”
Brad Chase to Barton after an unsuccessful Microsoft product bundle, as Barton later recalled.
The salary conversation gets a website
Glassdoor brought the same interest in transparency into employment. Barton co-founded the company in 2007 with Robert Hohman and Tim Besse, both Expedia alumni, and served as its non-executive chairman. The site launched in 2008. His place in this company was different from his operating role at Expedia: Hohman led the business as CEO.
Employee reviews and salary reports gave job seekers material beyond the official recruitment pitch. A job offer is both a financial decision and an invitation to spend much of one's waking week among strangers. The polished careers page rarely answers every question a candidate has.
Glassdoor's contribution model asked users to share information to gain access to more of it. The site's value depended on people supplying experiences that employers themselves had little reason to publish. By May 2018, it reported reviews and insights covering 770,000 companies across more than 190 countries.
That month, Recruit Holdings announced a $1.2 billion cash agreement to acquire Glassdoor. The deal closed in June. Expedia colleagues had now helped build businesses around travel, property and work. Barton repeatedly found collaborators in people he already knew, even while pursuing markets that initially looked unrelated.
The house that wouldn't behave like data
In 2010, Barton handed Zillow's CEO job to Spencer Rascoff and became executive chairman. He returned as chief executive in February 2019, as Zillow expanded into mortgages and directly buying and selling homes through Zillow Offers. The ambition had moved beyond helping people examine a transaction toward taking part in it.
The distinction became expensive. In November 2021, the board decided to wind down Zillow Offers. Unpredictable home prices, capacity constraints and operational difficulties had made it unsuitable as a stable business. The announced wind-down was expected to reduce the workforce by about a quarter.
This belongs in Barton's story alongside the launches. Owning houses meant committing capital while renovations, closings and resale unfolded. Publishing an estimate and carrying an inventory exposed the company to different consequences. The information could be useful to millions of people while the business of buying the underlying assets still failed.
His enthusiasm for large experiments had met a limit with consequences for employees as well as shareholders. Closing the operation was a substantial retreat. Any account that treats each new venture as another effortless expression of one clever principle misses what happened when that principle met a balance sheet full of houses.
Another seat, another address
On August 7, 2024, Jeremy Wacksman succeeded Barton as CEO. Barton became co-executive chairman alongside Frink. In his message about the transition, he described a move toward counseling Wacksman and the leadership team. The succession followed years of expanding responsibility for Wacksman, whom Zillow recruited from Microsoft in 2009.
Barton's other commitments include Netflix's board and Stanford's trustees. He and Sarah established an undergraduate scholarship fund at Stanford. Away from boardrooms, his own list of interests includes snowboarding, surfing, fly fishing and traveling. The person who helped put travel planning online still likes going somewhere.
In April 2026, he was discussing another shift: AI. At Zillow's AI Summit, he emphasized businesses with distinctive data, complicated transactions and deep connections to professional workflows. The interests were familiar, even with a new technology attached. He was still asking where useful knowledge meets an important decision.
Then, in June, came a more personal announcement. Barton had become a Las Vegas resident. His explanation pointed to children leaving home and the start of another chapter. After decades of helping strangers investigate their next address, he had changed his own. Even a career spent making things easier to look up leaves plenty of room for deciding what to do next.