AI Will Revolutionise How You Travel, Priceline CEO Says

With its 1997 launch as a name-your-own-price site, Priceline helped usher in the era of online travel booking―and the growth of a trillion-dollar category. Priceline itself has mushroomed into a global business with 1,500 full-time employees; along with global airline bookings, the site claims to offer 1.2 million accommodations in 116 countries.

Now, the Connecticut-based company is focusing on generative AI, and CEO Brett Keller is behind the leap. It’s just the latest technology push from Keller, a 25-year veteran of the company who has also served as CMO and COO. Under Keller, Priceline launched the travel industry’s first full-service mobile app in 2009; he also helped conceive the hugely popular William Shatner-fronted “Negotiator” ad campaign.

Keller, 56, talked to Penta about how AI is changing travel planning, what luxury travellers do to save money, and why Japan blows his mind.

Penta: Much of Priceline’s marketing is about value. Do you see luxury travellers in your customer mix along with budget-conscious travellers?

Brett Keller: High-net-worth consumers take a significantly higher number of trips than the average leisure traveller. For a high-end vacation like a safari in Tanzania, they’ll work with experts. But for the other 30 trips they book that year, either for themselves or family members, they don’t always reach for the stars. They want to manage money effectively. And as they’re moving around the country and the world, they need a fast, easy way to book travel that accommodates their needs. Priceline is a great platform for that kind of trip. And if you’re taking a quick weekend trip to Miami, and want to stay in the Four Seasons, we’ve negotiated with them. Even high-net-worth individuals seek value.

Priceline made headlines last year for partnering with both Google and OpenAI on Penny, your AI assistant. How has Penny evolved?

She’s gone from, “I can answer questions about the hotel you’re looking at” to actually servicing the customer through more complicated scenarios. If you need to cancel a hotel that’s fully refundable, you can do it with one click. But if there are issues, like a reservation that’s not fully cancelable, Penny can walk through those steps for you.

Penny’s also helping people find, search, and book properties. For example, if the customer tells her, “I’m looking for a great resort with these features, anywhere warm”—she’ll present recommended properties that meet those requirements. You can continue with Penny on the site, or go with the traditional experience.

Has there been any pushback from consumers about Penny and generative AI?

There has been none. Customers still have access to phone agents. Anyway, the younger generation doesn’t want to talk to anyone. And with traditional chat agents, live agents, or even messaging apps, there’s typically a delay. Penny answers immediately and in real time.

What’s the future of generative AI and online travel booking?

The future is a highly personalised shopping experience. It’s hard to achieve, because we don’t know about the consumer when they come in. But generative AI lets us dramatically improve personalisation. As you work with Penny, and tell us your preferences, the way you interact lets us find and book the best products and services every time you return. The ability to customise and personalise increases exponentially.

Is the travel experience even more bifurcated between elite, ultra-high-net-worth travellers and everyone else?

Consumers seem to be a little less sensitive in some areas. On planes, first-class and comfort-plus seats are the first to go, most of the time, and people are burning through points to sit in the front because they’re tired of not having legroom. But seats are packed in economy, too, so people are flying.

Hotel bookings are more economically driven in the U.S. Higher-income people are not as affected by interest rates or the cost of living, so they spend more freely than economy-minded consumers. There is a bit of bifurcation there. The low end is not filling, but the high end is.

It’s been reported Europe’s going to get even more crowded this summer. Does Priceline ever suggest alternatives to over-touristed or overpriced destinations?

We’re not in the business of telling you where you shouldn’t travel. We market popular destinations because that’s where people want to go. As much as we could tell people, “Las Vegas is overcrowded, don’t go,” people will want to go.

Social media is highlighting some overpopulated destinations and suggesting alternatives, so that comes back to us. But price is the No. 1 motivator. Vegas is a great value. There are so many hotel rooms available that you can go in a non-peak period and get a room in a four-star hotel for US$120. Try doing that in New York City.

What destinations are going to pop over the next year or two?

Asia will continue to be exciting and interesting to people. Bangkok is a great place to move in, then travel throughout Southeast Asia. As the region gets more popular, people will keep trying to find more remote and more unique destinations. People love Europe, but it was the hot spot in 2022 and ’23. Some travellers are saying, “I’ve had enough, and I’m moving on.” Japan is also amazing, for so many reasons. It’s easy to navigate. English is not a challenge. It’s safe. It feels like a different world, but completely first-world. The strength of the dollar is also driving some of that―again, price plays a role.

Beyond that, Mexico and the Caribbean took a real hit in 2022 and ’23 after a boom in 2021. They’re coming back now. A lot of people don’t want to travel far—“I just want to go to a beach and not think of anything.” And because not everyone wants to travel overseas, unique and relaxing cities like Nashville, Tennessee; Houston; and Austin, Texas, will be popular, especially into the fall.

Every day brings more headlines about airline woes. Who gets blamed if a Priceline customer has a bad flying experience, you or the airline?

When you have a bad experience traveling, you want to blame everybody. No matter what happened, the online travel agency takes blame and the airline takes the blame. It could be your seat, the person sitting next to you, whatever. We get the complaint, and we take on that responsibility and that role. We have leverage because of the amount of business we drive to partners. They want to work with us to make sure the customer has the best experience. Something goes wrong almost every time you take a trip. That’s just the reality.

What are your favourite places to travel?

My favourite destination, and a place where I spend a lot of time every summer, is [resort town] McCall, Idaho, one of the most beautiful towns in the West, with hiking, trails, and mountain biking. Outside of the country, it’s Japan, absolutely. Tokyo is the most exciting city in the world. It’s mind-blowing.

This interview has been edited for length and clarity.

Charities, distant relatives and even pets are benefiting from surprise inheritances. They can thank people without children.

Not having children is becoming more common, both among millennials and older people. A July Pew Research Center analysis found that 20% of U.S. adults age 50 and older hadn’t had children.

And many of these people don’t have wills. An AARP survey found half of childless people age 50-plus who live alone have a will, compared with 57% of others that age. Those without wills have less control over what happens to their money, which often ends up in the hands of people who don’t expect it.

This phenomenon of a surprise inheritance is common enough that it has a name: the laughing heir .

“All they do is get the money and go, ‘Ah ha ha, look at that,’ ” said Michael Ettinger , an estate lawyer in New York.

Kelley Gilpin McKeig, a 64-year-old healthcare-industry consultant in Ridgefield, Wash., received a phone call several years ago saying her cousin Nick Caldwell left behind money in a savings account. They hadn’t been in touch for 20 years.

“I thought it was a scam,” she said. “Nobody else in our family had heard that he had passed.”

She hunted down his death certificate and a news article and learned he had died about a year and a half before in a workplace accident.

Caldwell, who was in his 50s, had died without a will. His estate was split among cousins and an uncle. It took about two years for the money to be distributed because of the paperwork and court approval involved. Gilpin McKeig’s share was $2,300.

Afterward, she updated her will to make sure what she has doesn’t go to “just anybody down the line, or cousins I don’t care about.”

Who inherits

There are trillions of dollars at stake as baby boomers age.

Most people leave their money to spouses and children when they die. A 2021 analysis of Federal Reserve survey data found that 82% of heirs’ inheritances came from parents.

People with no children say they want to leave a greater share of their estates to charity, friends and extended family , according to research by two Yale law professors that surveyed 9,000 U.S. adults.

Rebecca Fornwalt, a 33-year-old writer, created a trust after landing a book deal. While her heirs are her parents, her backup heirs include her sister and about a half-dozen close friends. She set aside $15,000 for the care of each of her two dogs.

Susan Lassiter-Lyons , a financial coach in Florence, Ariz., said one childless client is leaving equal interests in her home to her two nephews. Another is leaving her home to a man she has been friends with for a long time.

“She broke his heart years ago and she feels guilted into leaving him property,” Lassiter-Lyons said.

A client who is a former escort estranged from her family is leaving her estate to two friends and to charity.

Lassiter-Lyons, who doesn’t have children, set up a trust for her two dogs should she and her wife die. The pet guardian, her wife’s sister, would live in their house while taking care of the dogs. When the dogs die, she inherits the house.

In the Yale study, people without descendants—children or grandchildren—intended to give 10% of their estates to charity, on average, more than triple the intended amount of those with descendants.

The Jewish Community Foundation of Los Angeles, which manages $1.3 billion of assets, a few years ago added an “heirless donors” section to its website that profiles donors and talks about building a legacy.

“Fifteen years ago, we never talked about child-free donors at all,” said Lew Groner , the foundation’s vice president for marketing.

In the absence of a will, heirs are determined by state law . Assets can wind up in the state’s hands. In New York, for example, $240 million in unclaimed funds over the past 10 years has arrived from estates of the deceased, not including real estate, according to the state comptroller’s office. In California, it is $54.3 million.

Hard questions

Financial advisers say a far bigger concern than who gets what is making sure there is enough money and support for a comfortable old age, because clients without children can’t call on them for help.

“I hope there is something left to leave,” said Stephanie Maxfield, a 43-year-old therapist in southern Colorado. “But if there isn’t, I think that’s OK, too.”

She said she would like to leave something to her partner’s nieces and nephews, as well as animal shelters and domestic-violence shelters. Her best friend is a beneficiary.

Choosing an estate executor and who would handle money and health decisions on your behalf can be difficult when you don’t have children, financial advisers say. Using a promised inheritance as a reward for taking care of you when you are older isn’t a good solution, said Jay Zigmont , an investment adviser focused on childless people.

“Unfortunately, it is relatively common to see family members who are in the will decide to opt for cheaper medical care (or similar decisions) in order to protect what they will be inheriting,” he said in an email.

Kirsten Tompkins, who is from Birmingham, U.K., and works in consulting, along with her husband divided their estate among their dozen nieces and nephews.

Choosing heirs was the easy part. What is hard is figuring out whom to ask for help as she and her husband get older, she said.

“A lot of us are at an age where we are playing that role for our parents,” the 50-year-old said, referring to tasks such as providing tech support and taking parents to medical appointments. “Who is going to do that for us?”

AI Will Revolutionise How You Travel, Priceline CEO Says

The bequests benefit charities, distant relatives and even pets

Who inherits

Hard questions