Season 3 of The Travel Again Podcast is off to a strong start, and this week’s episode features one of the true visionaries of the travel industry: Terry Jones. As the Chairman of Amgine and the founder of Travelocity and Kayak, Terry has spent decades shaping how we book and experience travel.
In this episode, hosts Mike McCormick and Ed Silver dive into Terry’s journey, his views on AI and innovation, and how travel companies can adapt to the fast-changing landscape. Below, we highlight the key takeaways from the conversation—followed by the full transcript for those who want to dig into the details.
Key Takeaways from Our Conversation with Terry Jones
1. The Evolution of Travel Tech: From Sabre to AI
Terry’s career began at Sabre, where he led early experiments in online travel. Recognizing the potential of the internet, he helped launch Travelocity, which disrupted traditional travel booking. Later, he co-founded Kayak, revolutionizing metasearch for travel.
"We proved with EasySaver that online booking would work, but the internet let us break free and build something bigger. That was exciting."
Now, Terry is focused on AI-driven travel solutions, helping companies optimize booking, customer service, and personalization.
2. AI is Reshaping the Travel Industry
Terry is a strong believer in AI’s transformative power. He compares today’s AI moment to the early days of the internet, where businesses that adapted quickly gained a major advantage.
"You're not going to lose your job to AI. You're going to lose it to someone who deploys AI better than you."
At Amgine, Terry is using AI to automate corporate travel management, reducing the inefficiencies of outdated booking systems. Instead of waiting for an agent’s response, AI-powered tools instantly generate policy-compliant flight, hotel, and car rental recommendations.
"We’re making travel booking feel like the days when an assistant just handled everything for you."
3. The Rise of Personalized Travel Experiences
One of AI’s most exciting promises is true personalization—something the travel industry has long struggled with.
"We've had personalization as a buzzword for years, but it's never been done well. AI is finally making it possible."
With AI-driven recommendations, booking experiences can adapt in real time. For example, an AI-powered itinerary builder could suggest alternatives based on weather changes, local events, or personal preferences.
4. Experimentation is Key to Innovation
Terry emphasized the importance of constant experimentation, recalling how some of Travelocity’s early innovations—like flight paging alerts—became massive hits, while others flopped.
"We tried putting fares on a map. The New York Times loved it. Consumers? Not so much."
His advice to travel companies? Keep testing, learning, and iterating—because the next big disruption is always around the corner.
Full Transcript: Travel Again Podcast - Terry Jones Episode
(Lightly edited for readability.)
Travel Again Podcast - Season 3, Episode 2Guest: Terry Jones, Chairman of Amgine
Announcer: Welcome to Travel Again Presents, the weekly travel roundup covering the headwinds and tailwinds impacting the business of travel. Please welcome our hosts, Mike McCormick and Ed Silver.
Ed: Hello, Mike.
Mike: Hey, Ed.
Ed: How are you doing today?
Mike: I am doing awesome.
Ed: Mike, welcome again to Season Three, Episode Two. Man, we are off to a great start to the season, and I am so jazzed about the guests we have planned. Our guest today is another amazing luminary of the travel industry, so I am thrilled to get us going.
Mike: Sounds good to me.
Ed: All right. With that, let's dive right into the news.
Ed: Mike, I have six articles for our first news item because there are so many stories covering this. What is the problem with air travel lately? What's the deal with all these incidents? We've had one Delta flight end up upside down, a near collision with a Southwest flight, a flight to India rerouted due to a terror scare, a Delta flight from Atlanta filled with smoke, and even a flight in Scottsdale with a Motley Crüe member on board where one person died. All of this just since our last recording! I personally don't see a pattern between these incidents. But give our listeners some perspective—what's the deal with all this airline mess, Mike?
Mike: Well, I think you're right not to jump to any conclusions. You have to be cautious not to force a pattern where there isn't one. I don't think there's any particular pattern here. With the sheer number of flights in the world, there's always a probability that you'll have some incidents—that's just reality. No system is 100% perfect or infallible. However, there are a few things to note. One is that any incident makes headline news. Travel safety is always of high interest to the public, so of course the news media covers it prominently. Another point, which we discussed when we talked about that mid-air collision in D.C., is that it's important to understand the root causes and take action where needed. In this case, the investment needed in modernizing our air traffic control system has been on the docket forever through multiple administrations. Everyone agrees it needs to be done; the issue, of course, is funding. So again, back to the main point: you can't conclude there's some sort of pattern here at all—it's just that any incident will always make the news.
Ed: Okay, thanks for that perspective, Mike. Moving along from the air travel woes to the hotel world. I picked up a couple of items here. First, Hyatt is set to acquire Playa Hotels & Resorts for $2.6 billion, marking a significant expansion of its all-inclusive resort portfolio in the Caribbean. I also saw that Hyatt is launching a new select-service brand. So a lot of action for Hyatt, and really a lot happening in the hotel space. Help our listeners get some context here, Mike.
Mike: Sure. Stepping back, I'd say the hotel industry at large—and certainly the major brands—continue to be very bullish about future demand, maybe even unmet demand out there in the marketplace. Marriott, for example (separately from this news), had their CEO talk through their plans for expansion—the hundreds of properties they have coming online across all segments. They are very bullish about the future. Hyatt has been growing by building new properties, but also through acquisitions like this Playa deal. It's an interesting growth strategy for them.
Ed: From a consumer perspective, I just don't understand having so many brands to support. Even we in the industry couldn't get 100% on a test of which sub-brand is which—we'd be lucky to pass it! They have so many brands covering roadside, mid-scale, upscale, luxury, and everything in between. I get the need for some sub-branding, but when you're carrying, like, 50 sub-brands, I don't see how that gets supported well from a marketing perspective. It certainly adds to consumer confusion. Obviously there's a strategy there, but still...
Ed: Mike, buried in the Marriott news is the return of the Starwood brand—adding back a brand name that Marriott had acquired and then retired. Now it's coming back to life. There must be a strategy there, though I'm not sure I totally understand it. Maybe Marriott felt people had a connection to Starwood, so they're bringing it back for that reason.
Mike: There's a bit of a backstory to that. When Marriott acquired Starwood from Barry Sternlicht, part of the deal was that Barry kept the rights to the Starwood name. He retired it and didn't do anything with it, and they waited years and years. Without knowing the exact agreement, maybe there was a time limit before Marriott could use the name again. Barry, in the meantime, developed some properties under the Baccarat brand—a smaller luxury portfolio. He still owns properties in the Marriott system as a major owner, so he has some influence. It sounds like now they’re ready to bring Starwood back to the market. It's a little unique behind the scenes, but it'll be interesting to see how it fits in. Certainly it's yet more brand noise and confusion out there. But hey, what do I know? It seems to work for them—it must, because everyone keeps doubling down on these sub-brands. Best Western, Choice, all the big chains are doing the same thing with micro-brands. It's a bit of a dilemma to me, but on the plus side, I like seeing big moves like this. Big acquisitions mean things are growing, and that's a good thing. So I'll take all of this as positive news overall.
Ed: Great points. Now, Mike, I'm going to change gears on you and switch to the corporate travel world. UK regulators have reversed their stance on the CWT deal. The UK’s Competition and Markets Authority (CMA) announced an about-face on the planned acquisition of CWT by American Express Global Business Travel. The CMA has provisionally concluded that CWT is a significantly weaker competitor than it used to be and will likely continue to weaken, and that other players will still provide alternatives to customers. Mike, this is exactly what we suspected last time we talked about the CWT–Amex GBT deal. Why the reversal, and what does this mean generally for M&A in the travel space?
Mike: First off, I think the original objection from the UK authorities was misplaced, and I'm glad they backed off. Given CWT’s economic situation and ownership, if it wasn't Amex stepping in, it would’ve been someone else—BCD or another player—attempting a merger. That had been talked about for a long time; CWT had been to the altar in different ways with different potential acquirers or partners over the years. So, in the scheme of things, this just wasn't the place to take a stand. Honestly, I think the combination of CWT and Amex GBT is good for competition. I don't see it as a bad thing at all. So we'll see where it goes. The betting markets actually show the deal is likely to go through—I checked, and you can bet on these things now! Hopefully the U.S. regulators will follow suit. We shall see, but overall I think this is positive.
Ed: Mike, that's our news for today. Now, on to our guest—and what a guest we have today! We’re excited to welcome Terry Jones. Terry is truly a luminary of the travel industry. He’s the founder of five startups—two of them had billion-dollar exits (that’s billion with a B!). He’s a noted speaker on AI, innovation, and disruption, and importantly he’s a speaker who’s actually done it. He’s served on the boards of about twenty companies with roughly $9 billion in exits. I could read off every company he’s worked with, but we’d be here all day—just a few highlights include Travelocity, Kayak, AMGiNE, Sabre... I even heard a great story about American Airlines from him in our pre-show chat. I think it’s best to just bring him on and let him tell his story. Please welcome to the show, Terry Jones!
Terry: Hey, guys!
Mike: Hey, Terry.
Mike: Welcome, Terry! That was a nice intro by Ed. On a personal note, I first got to know you back when I was working with Philip Wolf in the early days of Phocuswright.
Terry: Right.
Mike: Even then—during the early days of Travelocity and online travel—you were a pioneer. That alone would have been a huge success on its own. But what I find amazing is that you always seemed to see the next big thing coming. You helped lead Sabre into the online world, and then you saw the next iteration of travel tech—metasearch—and co-founded Kayak with Steve Hafner. It seems you've always had a vision of what's coming, and more importantly, you were able to act on it and make it a reality. That’s exceptional. You’ve also been a great ambassador for the industry over the years. So we’re really happy to have you on the show.
Terry: Thanks, Mike.
Ed: (laughs) With all that, we might as well say goodbye now! Just kidding. I’m really excited to dig in.
Ed: First, just a personal question to kick things off: What inspires you to do this? What inspired you to get into travel and be a part of all these innovations, driving so much success in the industry?
Terry: Well, I was with Sabre for a long time—as you know—and before that I had been involved in a couple of startups. I was a CIO, which is a terrible job. You're trying to orchestrate a lot of people who don't all want to go in the same direction. We had this little online thing on CompuServe and Prodigy and AOL, and they gave that to me. I thought, why isn't this on the Internet? Pretty soon I realized that would be a lot more interesting than being CIO, because it was about putting customer needs together with technology. We proved with EasySabre that online booking could work, and the Internet let us break free and do it on our own. That was so exciting. And then Kayak was the same kind of thing. We had a dinner with Steve Hafner, Paul English, a guy from Microsoft, and a VC. We talked about the fact that 90-plus percent of our customers were searching with us but buying somewhere else. We thought, why don't we solve that problem with metasearch? So we did.
Then I got a call from Ginni Rometty, the chairman of IBM, and she said, "Can you come teach IBM Watson about travel?" That sounded like fun, so I got involved. That ended up turning into an AI company where I was Chairman and Noreen Henry was CEO. We were too early—the tech worked great (and we'll talk more about AI later, I’m sure) and it actually increased conversion significantly, but we couldn't get hotels and cities to sign on. It was just too early. Which is why I'm excited now to be Chairman of AMGiNE, which is deploying AI into the TMC (travel management company) world.
I guess for me it's always been about listening to customers and figuring out what technology could solve their problem. Or sometimes, as a CIO or business leader, pointing out a new technology to the business and saying, hey, I think this could help us here. Being that bridge between business needs and technological capability—that's what's fun for me.
Mike: As you've gone through this process over the years and been part of so many different ventures, were there any big surprises along the way? Things that happened that you didn't expect—or things you expected that didn't happen?
Terry: I found that I was often too early with a lot of things. I was actually talking with the AMGiNE guys yesterday about this. I'm an idea guy—I was driving my team crazy because I was always coming up with new things at Travelocity. I ended up with two programmers who worked for me, and all I did was prototypes. We would put these prototypes out and see what happened. For example, we launched flight paging—that was so long ago we were literally paging people—and we were the first in the world to do that. It was a huge hit. Then I put out a fare calendar where you could click on a date to get the price. The New York Times loved it, but consumers didn't click on it at all. We tried showing fares on a map—nobody used it. But the point is, we were experimenting, failing, and learning.
So there were a lot of surprises, mostly because I was ahead of the customer in terms of what they were ready for. Back then, people were still trying to figure out if it was safe to even put their credit card in online. In fact, we put up an 800 number so people could call in and give us their credit card information, because they felt safer doing it that way. (We didn’t tell them that when they called, we were just entering it over the Internet on our end!) You have to work with both the customers’ desires and their fears of new tech.
Ed: Yeah, it's interesting you say that. That's always the marketing challenge, right? You can survey consumers all day long, but what they say they want and what they actually do with their money and time often differ. It’s a great point—and maybe a good segue into the topic of AI. To me, it seems like what's happening with AI right now is one massive experiment, as it should be. Test and learn, test and learn. Not in a vacuum, but with real users figuring out how they want to use it and where. I don’t think the roadmap is set yet; it’s still very early days.
Terry: The big thing is, these AIs are learning all the time. As a lecturer on AI, I was just with a thousand people in the mining industry yesterday, and I told them: if your competitor has learning systems in its products, operations, logistics, and you don't, how are you going to catch up? As somebody said, you're not going to lose your job to AI; you're going to lose your job to somebody who's deploying AI better than you.
Ed: Right. So, would you say that fear of losing out to a competitor is what's driving a lot of AI experimentation these days?
Terry: No, I don't think fear is the primary driver. I think people are excited by a new technology and they see that finally the time is right. We've had this convergence of big data and very large language models, plus the computing power (GPUs, cloud, etc.) to actually use them effectively. I'll give you an example: when we started Wayblazer (that was the AI company I mentioned), my partner wanted to go direct to consumer (B2C). I said, "We can't do it—we can't boil the ocean." If someone asks, "Where do I get the best Singapore Sling in Singapore?" we wouldn't know, and we'd get trashed on social media. We could handle a specific domain, like a hotel chain’s data, but not the whole world.
Now, though, you can start to tackle the whole world. You have massive datasets that can be consumed by LLMs, and you have the processing power to make use of it. So companies are experimenting; they're going to fail on some things and succeed on others. I actually think a lot of CEOs are naive about how widely AI is already being used. They might say "Oh, maybe 10% of our people are using AI," when in reality it might be 50-60% of employees experimenting with it in some form. ChatGPT opened everyone's eyes—it's great for drafting marketing copy, handling customer service chats, writing code, all sorts of tasks. But beyond those uses, the really important thing is building AI into your products and services.
For example, John Deere now has self-driving tractors that learn your specific fields—they know where to water, where to fertilize, where to kill weeds. Are you going to buy a tractor from a competitor that doesn't know your farm? Probably not, because once you have that advantage, you're hooked. I’m hoping we’ll see the same kind of thing with AI and personalization in travel, because frankly, personalization in travel has been a bit of a dud so far. It's never been done very well.
Ed: Right. You touched on some obstacles there—and some of them are at the C-suite level. If you're advising a CEO or business leader on how to deploy AI, where should they start? What kind of advice would you give them right now?
Terry: Well, obviously when we talk about obstacles, there's risk and security to consider. And you really need to focus on solving a real customer problem. So again, it comes back to listening to the customer and figuring that out. Someone at IBM once told me that the most impactful solutions will come from combining public data (say, data from OpenAI) with industry data (for example, data from ARC or airlines) and a company's proprietary data. The corporate data is the most important piece, because it's not out there in the wild for everyone to use. The question becomes, what new recipe can you create by mixing those ingredients?
I’ll give you a story. At Wayblazer, about nine years ago, we went to TripAdvisor and said, "Look, we've mined a million reviews from one of your competitors. We could mine your reviews and turn that into something really powerful." They declined. To this day, they still haven't really done it—though now I hear they're talking to startups like Perplexity AI, so maybe they're coming around. But think about it: TripAdvisor’s user reviews are a treasure trove of knowledge. If you combine that with the right AI technology, you could create a whole new way of shopping for travel.
So my advice is to be creative: look at what unique data or other assets you have, think about what the customer really wants, and figure out how combining those can change the game.
Mike: Looking forward now, with the companies you're involved in and the trends you're seeing: can you give us some examples of where you see real innovation happening with AI in travel today? And where do you think we might be a little further down the road, say with some emerging technologies?
Terry: I think AI will become the new UI—user interface—for travel. When we talk about natural language, today that often means text (typing), but it's also voice. It’s funny: we'll talk to Siri or Alexa on our phones, but we don't talk to our laptops. We're still mostly stuck with the old interface I helped roll out back in 1996 at Travelocity: "Where do you want to go, on what dates?" That's not how people really think about travel. People think, "I want to go to the Caribbean with my family. My wife wants a spa, I want golf, and we need things for the kids to do."
We have the capability to take an input like that now. Back at Wayblazer, we analyzed millions of photos and reviews. So if someone gave us that kind of request, the next page wouldn’t show just a generic hotel front. It might show a picture of the golf course at a resort, and a snippet of a review highlighting the spa. Companies are starting to dabble in this direction: for instance, Kayak has an AI-powered search where you can type something like "I want an American Airlines flight before 8 AM in first class," instead of clicking through filters. Booking.com has a new AI route planner on their app. So I think that's where things are headed. You mentioned the explosion of hotel brands earlier. We know that's largely driven by franchise deals. That's why you might see three Marriott-owned hotels on one city block—they can't open another of the same brand there, so they create different brands for each property. It doesn’t make much sense to consumers, but it makes business sense for development. I learned something interesting: Marriott is actually the largest operator of golf courses in the world, they have more spas than anybody, and they run more three-star restaurants than anyone (because so many high-end restaurants are in hotels). But as a consumer, you can't easily say, "Show me the best Marriott spa in France," regardless of which Marriott brand it is, because the systems aren't set up that way. It’s scale without consumer-facing meaning. I think AI will allow us to break through that barrier.
We're already seeing AI in back-end operations and in things like analyzing which hotel images or descriptions drive the most bookings. But we haven't seen as much on the consumer-facing side yet. A little further out, I think we'll see what some call agentic AI—AI agents working on our behalf. I was on a panel at Phocuswright about that concept. Someone predicted that this year we'll see consumers deploying their own AI agents to negotiate with AI agents on travel websites. That might be a bit ahead of its time, but I do think AI agents acting like a super-powered travel assistant could be very powerful, kind of like what metasearch did by sitting between consumers and suppliers.
I'm also advising a startup in Israel called RoutePerfect that ties into a couple of these ideas. One, they've gathered input from thousands of human tour guides about the best things to do in various places. Two, they're using AI to build day-by-day itineraries. If I say I want to go from Paris to Milan and I love wine and opera, it'll generate a day-by-day route with things I'd enjoy. That got me excited because, back in my very first job as a travel agent, I used to type out day-by-day itineraries for clients. None of the big online travel agencies really do full itineraries yet—they mostly just handle flights and hotels. And by the way, about half of hotel stays in the US and Europe are part of drive trips (people driving to their destination), which is something traditional sites don’t cater to well. So RoutePerfect is addressing that drive-market itinerary in a smart way.
I've seen a bunch of travel AI demos that are basically just using ChatGPT on generic data, and I don't think those will work—they'll likely fail because they lack depth. But the ones that add their own proprietary content and expertise to the mix, and enhance it with AI, those could be pretty interesting.
Mike: Yep. Love it. I completely agree—there’s a process there. Take your example: say I have a family trip to Florida for four days. If an AI could quickly give me a draft itinerary of activities for the kids, that’s incredibly valuable. And as you said (and as some Phocuswright research shows), a huge number of people are starting to experiment with these AI trip planners.
Terry: Yes. The challenge right now is that many of these AI travel planners aren’t connected to actually booking anything. With RoutePerfect, for example, we've connected the planning to purchasing. You can get your itinerary and then actually book it. Plus, there’s a mobile app you can use during your trip. If you’re out and about and it starts raining, the app can say, "Hey, it's raining—here are some indoor activities nearby you might enjoy," because it knows where you are. That kind of contextual assistance is where this is heading.
Mike: Right. And think about business travel, too—you could say to an AI, "I've got three meetings in Chicago, what hotel should I stay at to be close to them?"
Terry: Exactly. That's something we’re actually working on at AMGiNE. Right now about 60% of corporate travel bookings that aren't done by travelers themselves are handled via email requests. A traveler emails their agent something like, "I need to go to New York on Wednesday, stay at the Hilton, and come back Friday." Then the agent emails back a bunch of screenshots of options. It's terribly inefficient. We use NLP (natural language processing) to read that initial email and respond with a few curated options—air, hotel, car rental if needed—that fit the company policy and the traveler's preferences. To me, that's like having the old-school corporate travel agent experience, but faster. I remember when I had an executive assistant years ago: I’d say, "I need to be in New York on Friday, staying at X hotel, back Saturday," and then I'd just slam the door and it was done. That was so much easier than fiddling with booking websites for 30 minutes. With AI, we can get back to that level of convenience.
You can imagine integrating that into your calendar or whatever work app you're using (Salesforce, Outlook, etc.), so it already knows, for instance, that you have a meeting in midtown Manhattan at 9 AM and it suggests a hotel nearby that all your colleagues use and that's within policy. Then it just books it for you. That's the kind of seamless experience we're building toward at AMGiNE.
We’re also applying AI to things like group airfare. We saw travel managers juggling huge spreadsheets to coordinate flights for company meetings or incentive trips—lots of manual effort. We can automate that. We send forms out to everyone, collect their preferences, and in minutes we have options that fit the company's travel policy. It's not a flashy consumer feature, but it saves a ton of time and money behind the scenes. And all of that is really exciting to work on, even if it's not something the average traveler sees directly.
Ed: It is exciting. And to your point, Terry, it’s still early days—again.
Terry: Oh, yeah. We're at the beginning of another big wave, for sure.
Ed: All right, we have a wrap-up question that we’re asking all our guests this season. We’re debuting it on you! We all face a lot of chaos—both real and perceived—in our personal and professional lives. How do you cope with chaos in your life?
Terry: You know, I'm not sure I have a perfect answer, but I've always been pretty methodical even when I'm juggling twenty different things at once. I keep a pretty rigid to-do list, and I stick to it. Even now, after 20 years of essentially working for myself and sitting on numerous boards, that to-do list is my anchor. I also carve out a lot of time for reading up on what's new. I use Flipboard and other apps to aggregate news on topics I care about—AI, blockchain, whatever it is—so I can stay on top of the latest developments. I'll gather a bunch of articles and then read them all on the airplane when I'm heading to my next speaking gig.
I think it's about being both rigid and flexible. Rigid enough to get the important stuff done, but flexible enough to handle the chaos that inevitably comes at you and threatens to throw you off course.
Mike: So, basically, keep your eyes on the horizon and try to anticipate what's coming?
Terry: I do try to, yes.
Mike: Maybe one day we'll finally have true NDC across the industry.
Terry: (laughs) Yeah, right! Some of these industry initiatives, I swear—airline direct connect has been talked about since I had hair! What's old is new again in so many cases. We joke about it all the time—"someday, maybe..."
I’ll leave you with a quick story: I was talking with some folks about a cybersecurity lawsuit where they wanted me as an expert witness. I told them, "We never had that problem at Sabre." Back when we first hooked Sabre up to the Internet, people were terrified outsiders would hack it. I said, "Let them try." Sabre was this ancient beast written in assembly language, running on a terabyte-sized flat file database. If someone got into it, they wouldn't have the slightest idea what they were looking at or how to mess with it.
Ed: Only five people left on earth even understand that system, right?
Terry: Exactly! Nobody knows how to hack it, because nobody understands it anymore.
Ed: (laughs) That's great. Well, Terry, thank you so much for joining us. We really appreciate it.
Terry: Good to be with you guys.
Ed: For our listeners, Terry Jones is currently Chairman of AMGiNE and a public speaker on a range of technology topics. Terry, it’s been great having you on the show—thanks for your time today.
Terry: My pleasure. And if anyone wants to follow up, just check out TerryJones.com.
Mike: There you go—TerryJones.com.
Ed: Thank you, Terry. Best of luck with everything.
Terry: Thanks.
Ed: All right, Mike—what a great guest. Incredible background and so much knowledge.
Mike: Really great perspective.
Ed: Absolutely. Okay, that’s our show for today. If you have a challenge in your business or you want to better understand the chaotic world of travel, reach out to us at TravelAgainAdvisory.com. We’re here to help. Mike, we'll be back in about two weeks with our next episode.
Ed: Thanks again for listening to Travel Again. See you next time.
Packed with insights into the future of travel and AI’s role in shaping the industry. If you want to hear it straight from Terry, be sure to check out the full episode on YouTube:
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