Expedia has positioned itself solely as a booking platform rather than an entity that enhances the travel experience. Your travel experience remains virtually identical, whether you book through Expedia or any other platform. Successful commerce and e-commerce companies don’t operate that way—they strive to improve customer experiences through benefits like faster delivery speeds, generous return policies, and competitive pricing.

Expedia’s limited focus on improving the travel experience has contributed to high customer acquisition and retention costs. Roughly half of Expedia’s revenue is allocated to sales and marketing.

When we travel, we are vulnerable, and there are many opportunities for Expedia to improve our experience and reduce that vulnerability. Since September 11, 2001, airport security has become a frustrating obstacle for travelers. Some companies, like Clear, have emerged to solve this problem. But why is Clear a separate company? Why didn’t Expedia tackle this issue itself—and in a more efficient way? Today, when you book a flight through Expedia, it advertises Clear services: “You have earned two free months of Clear.” Instead, the message should be: “You have earned two free months of Expedia+, which includes fast airport security and other exclusive perks—all for $X/month.”

If Expedia had 50+ million paid subscribers, it would have real negotiating power with airlines. Missing a connection can be frustrating, as airlines prioritize cost efficiency over traveler convenience. If Expedia dictated the terms, airlines selling tickets to Expedia subscribers would need to allow rebooking through Expedia’s app—with any airline available on Expedia, not just the originally booked carrier. E-commerce platforms seamlessly handle returns—shouldn’t Expedia ensure travelers can switch flights just as easily, especially during disruptions?

On the convenience side, perks like in-flight and hotel WiFi were once premium services. Expedia+ could have made them complimentary before anyone else did. Similarly, credit card companies offer airport lounge access—Expedia+ could include this benefit as well. Even better, a trillion-dollar Expedia could operate hundreds of its own lounges in major airports. At one point, the e-commerce industry believed infrastructure investment wasn’t its responsibility. Today, leading e-commerce companies have proven that owning infrastructure enables lower costs, faster service, and a competitive edge. So where is Expedia’s equivalent infrastructure?

From a supplier perspective, small hoteliers struggle with pricing. Every night and every type of room represents a unique inventory. Unlike other industries, travel inventory expires—once a flight takes off or a night ends, vacant seats or rooms go unused. Large brands have dedicated data analysis teams to optimize pricing and inventory management, but smaller suppliers lack those resources. Expedia could level the playing field between small suppliers and larger hotel chains.

Expedia could have joined the trillion-dollar club—or still could, if it has the courage to execute on its own imagination. AI-driven productivity gains will likely increase travel demand. Planning a vacation or any trip is often a tedious chore—can Expedia outcompete search engines, social platforms, or AI companies in streamlining this process? Could a travel-agentic Expedia become the superior solution?

One potential advantage is its ability to act as a real-time travel agent. For example, imagine you’ve planned an indoor event for today and an outdoor activity for tomorrow during your vacation. Expedia’s AI agent detects unfavorable weather for tomorrow and proactively alerts you, offering to swap the activities and handle all necessary travel arrangements. With real-time inventory access, Expedia is uniquely positioned to monitor and enhance travelers’ experiences.

I leave the audience with these questions: What travel problem do you think Expedia should solve? Could it still shoot for a trillion-dollar valuation in the next 25 years? I’d love to hear your thoughts.