From her office overlooking the atrium at Expedia Group’s sunlit headquarters campus on the Seattle waterfront, CEO Ariane Gorin puts the online travel giant’s 30-year history into three chapters, each tied to a major inflection point in the evolution of technology.

Chapter 1 was the internet itself: the 1996 launch of Expedia inside Microsoft, when a small team bet that consumers could benefit from technology previously exclusive to travel agents.

Chapter 2 was mobile: as travelers migrated from desktop to smartphone, Expedia rebuilt itself for the small screen and assembled a collection of brands through a wave of acquisitions. 

Chapter 3, Gorin says, is artificial intelligence, and it’s only starting to unfold. Expedia is now positioning itself for a new reality in which different types of agents — machines, not humans — will play a role in booking travel, in some cases making the decisions entirely on their own.

“It’s exciting to get to write the future of AI and travel,” Gorin said.

Expedia is marking its 30th year in business this week with the launch of the Expedia Trails Fund, a philanthropic initiative to restore outdoor trails across the U.S., backed by an initial $4.3 million in grants. 

The company is also bringing top executives from throughout its history — founder Rich Barton, chairman Barry Diller, and former CEO Dara Khosrowshahi — together with Gorin for its partner conference in Las Vegas. Collectively, they grew Expedia from internal division to corporate spinout to online travel giant. 

What happens next, under Gorin, will depend on Expedia’s ability to reinvent itself for a fundamentally new relationship between travelers and technology — attempting to continue a pattern that has repeated itself throughout the company’s history.

Chapter 1: ‘Power to the people’

Expedia started with a question: why shouldn’t everyone see what travel agents do? 

In 1994, Rich Barton was a 27-year-old Microsoft employee, working on a CD-ROM travel guidebook — an Encarta for travel — when he learned about the airline reservation systems that travel agents used to book flights. The systems were accessible electronically, but only to industry insiders. He started to imagine regular people using them directly.

“The idea was simple and almost obvious once you said it out loud: give consumers the same information the professionals have, and get out of their way,” recalled Barton, now a well-known entrepreneur and investor, who shared new details of the Expedia story for this piece. 

His term for this approach would ultimately define his career: “Power to the People.”

Barton pitched the idea directly to Microsoft CEO Bill Gates and President Steve Ballmer, who gave him the green light.

Secretly building for the web

The team initially started building the product for Microsoft’s proprietary online service, MSN 1.0, a would-be competitor to AOL, which had a proprietary multimedia development environment called Blackbird. Then the web gained steam, with its open protocols and universal reach. 

That’s when Greg Slyngstad, the original general manager of what was then called Microsoft Travel, made a pivotal call: develop the product for the open web instead of Microsoft’s walled garden. 

Slyngstad “knew the web would win,” Barton said. “Because of this, we secretly built for the web, which was brilliant. Expedia would not be what it is today if not for that decision.” 

Before it was called Expedia, the project had a very different interface. In the early days of Microsoft Travel, the hot trend in software was the social user interface, personified most memorably by the widely mocked Microsoft Bob. Barton’s team had its own version: a parrot that served as a travel planning guide.

“I can’t remember the name of the parrot now,” he said, “but I faked a travel planning scenario talking to a robot parrot in front of the whole Consumer Division — which was a hit!”

‘We had massive ambition’

A plaque still on the Microsoft campus in Redmond marks what came next: “Microsoft Expedia, Version 1.0, Shipped October 22, 1996.”

Microsoft’s annual report for 1997 described Expedia as “a free travel service on the World Wide Web and MSN which enables users to find low fares, book flights, make hotel reservations, and rent cars.”

Barton and team had a much bigger vision. “We had massive ambition,” he said. Their BHAG — or “big, hairy, audacious goal,” the term popularized by author Jim Collins around the same time — was to become “the largest seller of travel in the world.”

Expedia’s revenue went from zero to $38.7 million by 1999. At the time, it was still about half the size of Travelocity, which had gotten to market first. 

‘Go do this on your own!’

But Barton was already seeing a future for Expedia outside the software giant. 

“One of my core arguments was that Expedia, in success, would become a travel company first and a tech company second,” he explained. “Therefore, we simply wouldn’t fit inside a giant tech company, and that by setting us free, it would dramatically improve our chances of fulfilling our giant global dreams.”

So Barton made the case to Ballmer, his boss at the time, to let him and his team of “internet adventurers” spin out through an initial public offering, with Microsoft retaining a stake.

He pasted a printout of Ballmer’s headshot onto an IATA card, the credential issued by the International Air Transport Association to licensed travel agents. “Steve, do you want to be a travel agent?” Barton remembers asking. “Do you want to run the largest travel agency in the world?”

Ballmer recoiled at the idea and yelled, “No, you guys should go do this on your own!” Then he asked if he could keep the card.

And with that, the spinout was set in motion.

The IPO prospectus in September 1999 described Expedia’s value proposition: “one-stop travel shopping and reservation services, providing reliable, real-time access to schedule, pricing and availability information.” Travel, it said, was uniquely suited to the internet: a global market with millions of buyers, and purchases “involving large amounts of information from multiple sources.”

‘Whoops and hollers’

Expedia went public on Nov. 10, 1999. The company had 138 employees. The stock, initially priced at $14 a share, soared more than 260% on its first day of trading. 

“We’re feelin’ pretty good,” said Suzi Levine, who led Expedia’s IPO communications, in a Seattle Post-Intelligencer story about the Nasdaq debut, admitting “there may have been one or two whoops and hollers” around the office. Levine went on to become the U.S. Ambassador to Switzerland under President Obama, among other high-profile government positions. 

Another newspaper clipping from that week shows Barton and his wife Sarah holding their newborn son William, born the same day as the IPO. The headline: “Initial public offspring.”

Within two years, Expedia had surpassed Travelocity to become the largest online travel company. Barton left in 2003, eventually going on to co-found ventures including Zillow and Glassdoor, applying the same “power to the people” philosophy — giving consumers access to data that industries had previously kept behind walls — to real estate and the job market.

Before Barton left, controlling interest in Expedia had passed to a new owner. But the deal that made it happen nearly didn’t survive the worst moment in the history of modern travel.

Chapter 2: ‘If there’s life, there’s travel’

Barry Diller was a Hollywood legend who had built Fox Broadcasting and launched the Home Shopping Network when he turned his attention to the internet in the late 1990s. 

Through his company, USA Networks, he was assembling a portfolio of online brands, and he saw travel as the biggest opportunity. Travel, he wrote in his 2025 memoir, Who Knew, looked like “the perfect business to be colonized by the internet.” He had already acquired Hotels.com when he approached Microsoft about buying its controlling stake in Expedia. 

Expedia was still losing money, and Ballmer had concluded that Microsoft shouldn’t be in internet verticals anyway, as Diller recalled in the book. With relatively little negotiation, Microsoft agreed to a deal worth about $1 billion in USA Networks stock.

They were set to close the deal in October 2001. Then, on September 11, the travel industry shut down in an instant. The deal included a material adverse change clause — a legal escape hatch that would have let Diller walk away. For weeks, his team debated whether to use it. 

How could they pay $1 billion for a travel company when no one was traveling?

“Some people said, you shouldn’t do it, it’s too dicey, there’s no travel, the world is ending,” Diller told GeekWire in 2016, on the company’s 20th anniversary.

But then, someone in the room said, “If there’s life, there’s travel.”

“Yeah, that’s what we’ll do,” Diller recalled saying. “We’ll bet on life.”

The next transition

The deal closed in February 2002. Diller folded Expedia into a division of his company called IAC Travel. When the head of that division resigned, a young executive named Dara Khosrowshahi raised his hand. Khosrowshahi had first crossed paths with Diller as a junior analyst at the investment bank Allen & Company, and had been in the room during the 9/11 deliberations. 

“Barry was desperate. He had no one else,” Khosrowshahi recalled on the Diary of a CEO podcast. 

In 2005, Diller spun IAC Travel back out as a standalone public company — Expedia, Inc. — with Khosrowshahi as CEO. He moved to what he later called “the Netherlands of Seattle.” He would hold the role for 12 years, longer than any leader in the company’s history.

It was under Khosrowshahi that Expedia navigated the shift from desktop to mobile. As travelers migrated to smartphones, the company rebuilt its products for the small screen.

Khosrowshahi also led an acquisition spree that transformed Expedia from a single brand into a travel conglomerate, adding Orbitz, Travelocity, Trivago, and others along the way. 

Competition from all corners

Even as Expedia consolidated its position in online travel, a different kind of threat was emerging. Google was pushing into travel directly through Google Flights and Google Hotels, and its search algorithm had become the dominant gateway to travel shoppers — making the search giant Expedia’s biggest advertising channel and one of its largest competitors.

Google’s position is “a reality of e-commerce,” Khosrowshahi said in a 2016 interview with GeekWire, on the company’s 20th anniversary, in the conference room at its Bellevue, Wash., headquarters. “It’s reality of the Internet, and it’s certainly a reality of this category in general. That’s not going to stop.

The bigger direct threat, though, was emerging from across the Atlantic. The Priceline Group — later renamed Booking Holdings — had acquired Booking.com out of Amsterdam in 2005, building a business that would eventually surpass Expedia in gross bookings.

“Priceline is our toughest competitor,” Khosrowshahi said at the time, calling it a great company that had quickly expanded its international reach. “They’re more global than we are.”

And then there was a competitive threat that nobody at Expedia had anticipated: the rise of vacation rentals as a category, led by Airbnb. Expedia’s response was its biggest deal yet: the 2015 acquisition of HomeAway, which would later be rebranded as Vrbo — a $3.9 billion bet on the category.

“I think the growth of Airbnb has been pretty extraordinary, and I think anyone who would say today, ‘Oh, we expected it,’ would be lying,” Khosrowshahi said in the interview. 

The one exception, he acknowledged, was Airbnb founder Brian Chesky, who was known for transforming the world of lodging just as Uber’s Travis Kalanick had upended transportation.

‘You’re f’ng crazy’ 

The next year, Uber came calling for Dara. 

At the time, the ride-hailing company was in turmoil — embroiled in scandals, burning billions, and in need of a leader who could steady the ship. When Khosrowshahi told Diller he’d been offered the job as Uber’s CEO, the chairman’s first reaction was to hang up on him.

“He’s like, you’re f’ng crazy,” Khosrowshahi said on the Acquired podcast. 

But Diller called back the next day. “Speaking as the chairman of Expedia, it will be a real mistake,” Khosrowshahi recalled him saying. “But speaking as a friend, I understand why you’re interested. How can I help?” Diller then helped him prepare his presentation for the Uber board.

In a farewell email to Expedia staff, obtained by GeekWire at the time, Khosrowshahi called Diller “the toughest, smartest, most demanding, and most human boss I’ve ever had.” 

Ketchup and mustard

One of the company’s rising executives at the time was Ariane Gorin. A Berkeley, Calif., native who grew up in a French-American family, she had moved to France in 2001 and lived in Europe for more than two decades, eventually becoming a dual French-American citizen. 

The future Expedia CEO had joined the company in 2013, and her first encounter with Expedia’s leadership set the tone: she met Khosrowshahi and CFO Mark Okerstrom on Halloween, when they were dressed as ketchup and mustard. “This is the best company,” she recalls thinking.

Okerstrom succeeded Khosrowshahi as CEO in August 2017. By comparison, his tenure was brief, most notable for Expedia’s move from downtown Bellevue to a picturesque former biotech campus on the Seattle waterfront, and an ambitious effort to unify its technology across its growing collection of brands.

After a strategy disagreement with the board over the pace and direction of the tech revamp, Okerstrom and CFO Alan Pickerill both resigned on the same day: Dec. 4, 2019. Diller, as chairman, asserted direct operational control alongside vice chairman Peter Kern, a longtime Expedia board member. 

‘I’m on the edge of revolt’

Eight days later, on December 12, 2019, Diller put his frustration with Google in writing. In an email to Google’s chief business officer, Philipp Schindler — which later surfaced in the U.S. government’s antitrust case against Google — the chairman wrote that “much of Expedia’s trouble is due to an increasingly aggressive Google.” 

Diller cited Vrbo’s payments to Google, which had risen from $21 million in 2015 to nearly $300 million in 2019, even as the traffic Google sent to VRBO stayed roughly flat.

“Google has systematically moved every lever in its hegemony over search to disembowel our businesses,” Diller wrote, describing himself as “on the edge of revolt.”

It wouldn’t be the last time Expedia found itself subject to forces beyond its control.

‘Buy the thing’

In the meantime, Diller had been shaping the company’s new home. In the mid-2010s, he had pushed Expedia to acquire a 40-acre site on Elliott Bay, formerly occupied by Immunex, maker of the arthritis drug Enbrel. The site was vacated after Amgen bought the Seattle biotech.

“Once I saw it, I just said, ‘buy the thing,’” Diller said at a 2023 company event. He wanted a campus that felt horizontal, not vertical, with what he called “a lot of ability to breathe.” 

Over five years of planning, Diller personally shaped details down to the geometric paving stones that radiate outward from the main building like airport runways. The campus included 1,000 trees, an on-site soccer pitch, and a meeting pavilion called “the Prow,” designed to rise out of the landscape like the bow of a ship. 

Beyond the property line, Expedia funded improvements to a portion of the Elliott Bay Trail running alongside the campus. That gave the company a sense for how it could invest in outdoor public spaces — an early version of the work it’s now expanding nationwide. 

The first of Expedia’s began moving into the campus in October 2019. By February 2020, the move was complete, at a final cost of more than $1.1 billion. 

‘Travel finds a way’

In April 2020, when Kern was formally named CEO, COVID-19 had brought the industry to a halt. He used the moment to complete the overhaul of Expedia’s technology platform, unifying the patchwork of systems that had accumulated through years of acquisitions. 

“Travel finds a way,” Kern said in a virtual appearance at the 2020 GeekWire Summit, predicting that cities would come “roaring back,” and the industry would ultimately rebound. 

In the meantime, Gorin had been building what would become one of Expedia Group’s most important business lines. In 2014, Khosrowshahi had asked if she was interested in running the company’s affiliate network, which licensed the company’s travel technology and inventory to outside partners, letting them offer Expedia-powered bookings under their own brands. 

It was less than 10% of the company’s business, and nobody else wanted the job.

“B2B was not seen as a sexy part of the company,” she recalled recently.

Gorin jumped in with passport in hand. She spent her initial months in the job talking to partners around the world, developing a strategy of going where Expedia’s own consumer brands couldn’t or didn’t go, including offline retail, corporate travel, emerging markets, and anywhere else there were untapped pools of travel demand. 

Over the next decade, she grew the B2B division from a small afterthought into one of the company’s most important businesses. Today it accounts for roughly a third of Expedia’s overall business, powering travel programs for companies like Marriott, Hilton, United, Delta, and Capital One. 

It was, in retrospect, perfect preparation for what would come next. 

Chapter 3: ‘The agent that roams with you’ 

Long before ChatGPT became a household name, the head of OpenAI was already sitting on Expedia’s board. Sam Altman joined Expedia Group’s board of directors in 2019, recruited at a time when his AI research lab was still better known in Silicon Valley than in living rooms. 

In November 2022, weeks before ChatGPT was unveiled to the world, Altman appeared on stage with Diller at a private executive event for IAC, the parent media company in Diller’s portfolio. Altman demonstrated what was coming by typing a prompt asking ChatGPT about Diller’s relationship with his wife, the fashion designer Diane von Furstenberg.

What the AI produced was “extremely creative” and “somewhat salacious,” Diller recalled at Expedia’s 2023 partner conference. “Because we do have a history.” 

More than that, it was a glimpse of the future. Diller said the preview gave Expedia an early jump on generative AI. The company was one of the first travel firms to integrate ChatGPT — both as a plugin on OpenAI’s platform and as a travel-planning assistant in its own app. 

It actually wasn’t a surprise to Diller. Speaking with GeekWire back in 2016, Mr. Diller (as we were advised to call him) had described AI as “another form of magic.” Asked whether it would influence travel, he said at the time: “Of course it will. It will influence everything.” 

Altman left the board in June 2023, as OpenAI consumed his full attention.

From B2B to B2A 

When Kern stepped down in May 2024, Ariane Gorin — the executive who had been steadily expanding the company’s business-to-business reach — became Expedia Group’s CEO.

She soon had a phrase for what the AI era would require: B2A, for business to agent. But there’s a risk in this new world: a human traveler might choose Expedia out of loyalty, or brand recognition, but an AI agent making the same decision might not care about any of that.

In a recent interview at Expedia headquarters, Gorin said the company now has teams looking at what it means to market to machines: how to make sure an AI agent understands that an Expedia Gold member gets a VIP perk at a particular hotel, or that a traveler has One Key points to apply toward a trip.

Expedia has been building AI into its own products for years now. But more recently, it has been looking outward: embedding its service inside ChatGPT, Claude, and Amazon’s Alexa+, buying ads inside AI chatbots, and signing a deal to power Uber’s hotel bookings. (Khosrowshahi, who remains on the Expedia Group board, recused himself from the negotiations over that partnership.)

“I think that’s the future,” Gorin said. “It’s the agent that really roams with you.”

A competitive moat

It’s still early. AI-native platforms like ChatGPT account for less than 1.5% of Expedia’s overall traffic, Gorin said. But the company said on its recent earnings call that getting its brands to show up in AI responses has become its fastest-growing marketing channel.

As demonstrated by Diller’s past frustrations with Google, these external dependencies can be a double-edged sword. But there are early signs that Expedia won’t be cut out of the picture. In March, OpenAI scaled back plans to let users book travel directly inside ChatGPT. 

Gorin said she wasn’t surprised, given the complexities of travel. “Trust me, it’s pretty complicated to be able to go from shopping to booking to servicing,” she said. Expedia handles 250 million customer service interactions a year, across more than 30 languages. 

“I see them as partners,” more than competitive threats, she said of the major AI platforms. “I see them as an opportunity for us to attract new travelers into our ecosystem.” 

Illustrating the ongoing importance of industry partnerships, Expedia struck a deal this spring to power hotel bookings inside the Uber app, with Vrbo vacation rentals coming later this year. Khosrowshahi, who still sits on Expedia’s board, recused himself from the deal.

Growth and challenges

The company that began in 1996 as a small team inside Microsoft is now on a different scale entirely. When Expedia went public in November 1999, it had fewer than 150 employees, about $700 million in gross bookings, and a presence in four countries. 

Fast forward nearly 30 years, to the end of 2025, and Expedia had roughly 16,000 employees across nearly 50 countries, $119.6 billion in gross bookings, and a marketplace of 3.6 million lodging properties, including 2.4 million vacation rentals.

The company’s evolution has also brought challenges, including executive turnover and job cuts — with the latest round impacting 162 tech positions at the company’s headquarters earlier this year.

‘More travel equals more memories’

Gorin, meanwhile, has been putting her own stamp on the company. 

To mark its 30th year, Expedia is launching the Expedia Trails Fund, a philanthropic initiative to restore outdoor trails and protect natural landscapes across the United States. 

The initial $4.3 million will go to 11 projects, spanning destinations from Yellowstone’s Paradise Valley to Hawaii’s Kealakekua Bay, covering areas that draw more than 1 million visits annually. Expedia is partnering with The Conservation Fund, The Nature Conservancy, and Trust for Public Land, and with AllTrails to match support for the hiking app’s stewards fund. 

The effort reflects growing demand among travelers for outdoor experiences, particularly among younger generations. Gorin said the company’s earlier trail work alongside its Seattle campus helped to show what could be possible at a larger scale.

“If our trails fund really works the way we want it to, the impact we’re going to have on trails across the U.S. and elsewhere is going to be huge,” she said.

For Gorin, the initiative connects to something deeper. A few years after she joined Expedia, her sister was diagnosed with stage four lung cancer. Before she died, she offered Gorin a piece of advice: travel more, because more travel equals more memories.

“And then she said, ‘Oh, wait a minute. You work in travel. One day, you should use that story on stage,’” Gorin recalled. She told it at her first town hall as CEO.

“We are in the business of helping people make memories,” Gorin said. The common thread among all of Expedia’s CEOs over the years, she said, is a belief in the benefits of travel for people and the world, and in the potential of technology to achieve it.

‘Original vision … fully realized’

But if Expedia’s founding vision was to remove the barriers to travel, isn’t there a risk of people losing control when AI puts a new intermediary into the process? Barton, the person who started it all, doesn’t buy that. He draws a direct line from the original idea to the present moment.

“Round one was radical transparency,” he said. “We blew the doors open and gave everyone access to information that used to live only in a computer on the desk of a professional.”

AI agents, Barton asserts, are “the next unlock.” Rather than replacing the human in the loop, he said, they give every traveler “the equivalent of a brilliant, tireless expert in their corner.” That makes AI an accelerant for the concept of “Power to the People,” not a replacement.

“I don’t see it as a threat. I see it as the original vision, finally fully realized,” he said. “We started by turning the screen around. Now we’re handing people the whole toolkit.”

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