Booking Holdings

This is the oral history of Priceline's two deals, the acquisitions of Active Hotels and Bookings B.V., that created Booking.com, and continue to shape the course of online travel and the competitive landscape today. The twin transactions were among the greatest Internet deals of all time, and their lessons are relevant to startups and dealmakers in any industry.

Online travel agencies remain essential to the travel industry as consolidators of, and clearinghouses for, advertising dollars throughout the space. We do not see OTAs being removed from this position easily, but growing challenges have hurt ad efficiency. OTAs must remain nimble to keep pace.

TV ads can be the hippest type of marketing. But the personal brand of Booking.com's chief marketing officer Pepijn Rijvers is tied up in a data-first approach that instead emphasizes paid ads in search engines.

Online travel agencies remain essential to the travel industry as consolidators of, and clearinghouses for, advertising dollars throughout the space. We do not see OTAs being removed from this position easily, but challenges are growing by the day.

Online travel's two most influential female executives, Ctrip's Jane Jie Sun and Booking.com's Gillian Tans, will now deliberate around the table together at Ctrip board meetings. Ctrip felt the need to announce that the two companies are strengthening their ties after Booking's 2017 investment in Ctrip rival and IPO-bound Meituan-Dianping.

We wonder whether Airbnb's community spirit will survive its growth plans and impending IPO.

While Airbnb has been brashly adding independent hotels, HomeAway has been quietly doing the same — although it has been using an entirely different business model given its ties to parent Expedia. Curation may have its place, but all of these companies realize that the more inventory and choice they give consumers, the more likely they are to spend on a stay.

TripAdvisor CEO Stephen Kaufer is ordinarily far from being the most-compensated CEO in online travel. This year represented an unusual payout for him. But Skift's annual survey reveals that most online travel CEOs are often more handsomely compensated than what the top bosses in other industries receive, on average.

Amazon likely has a role to play in the future of travel distribution, marketing, or devices — if not all three. Travel leaders need to prepare today or risk being caught flat-footed tomorrow.

In some ways, Trivago and TripAdvisor find themselves in similar situations, although TripAdvisor has more upside because of its global brand awareness and the breadth of its offerings. But both need time to play the long game. In Trivago's case, it is now seeing alternative accommodations as a potential life line.