The Man Behind Travelocity Explains How AI Will Change Everything | Terry B. Jones

Welcome to the Legacy All-Stars Podcast. We feature inspirational stories from people who dedicate themselves to helping others. Here is your host, Alan Pavlosky.

All right. All right. Welcome back to the Legacy All-Stars Podcast. I'm your host, Alan Pavlosky. Let me ask you a question. What if you booked a flight, planned a road trip, or compared travel prices online? All traces back to one visionary who saw the future before anyone else did. Today I am genuinely honored and pleased to sit down with a man who has quietly shaped the way billions of people experience the world. Literally. Terry B. Jones is the founder and former CEO of Travelocity, the platform that revolutionized how consumers access travel. He's the founding chairman of kayak.com, a company that changed price comparison forever and sold for nearly $2 billion. He served as Chief Information Officer at Sabre Inc., one of the largest and most sophisticated technological companies that focuses on infrastructure in the world for travel. He's founded 5 startups, served on over 20 boards, and generated more than $10 billion in combined exits. He's a published author, an internationally recognized keynote speaker, and an advisor who still pours his knowledge into the next generation of entrepreneurs. But here's what really drew me to Terry for this conversation. Behind the billion-dollar companies and the industry-shaping innovation, he is a leader who believes deeply in the responsibility that comes with success. Terry has dedicated decades to mentoring rising entrepreneurs, helping companies navigate disruption with integrity, and using the power of technology to connect people to new possibilities. That commitment to lifting others as you climb, that is what Legacy All-Stars is all about. And that's our mindset. Terry, welcome to the show. It's great to have you.

Thanks, Alan. Great to be here.

Yeah, total pleasure. Let's get started right away. We got a lot to cover and I want to make sure our audience gets the most out of this. Take us back to the beginning. You entered the travel industry as a travel agent in 1971. What did those early years teach you about how people want to experience the world?

You know, when I graduated from college, I thought I was going to Vietnam. I had a very low draft number, but I got rejected for the draft because I have a bad back. And my college roommate's dad was a pilot for TWA, had a free pass. And he said, "Before I go to grad school, I'm going around the world." So 3 of us spent a year going around the world. One of the best experiences of my life. We spent a year. And I really learned that travel is about experiences. It's about having somebody explain what the Palace of Knossos is all about, or eating a meal in a 3-star French restaurant, or seeing the sunset in Machu Picchu. That's what people want. Of course, the question is, and I spent my life about this, how do you book it? How do you get there? How do you find it? But that, that's what's travel about. In fact, experiences are way more important than ever for travelers today.

Yeah, for sure. You spent 24 years at Sabre and American Airlines before launching Travelocity. At what point did you realize the internet was not just a tool, but it was going to fundamentally change how people live and do business?

You know, we'd had an online travel product for many years at Sabre. We powered travel agents, but we had a thing called Easy Sabre on AOL and CompuServe and Prodigy, those old closed networks, and They gave the responsibility for that to me in 1996. And I said, why isn't this on the internet? So we put it on the internet. And of course, IT was worried about security and there were a lot of issues, but it was the perfect product. It was fascinating. People on Wall Street, we took it public, thought, well, it's going to be toys.com and, you know, delivery products. It turns out Travel, the pricing changes all the time. You don't necessarily buy the same thing over and over again. Images and reviews are really important. Travel is the number one piece of e-commerce on the internet, you know. So, uh, I knew it was going to be good. I didn't know it was going to be that good.

Yeah. Well, founding Travelocity in the mid-'90s was, to me, was a genuinely bold move. What was the biggest resistance you faced internally, and how did you push through it?

Well, you know, we were a company at Sabre, we were part of American Airlines, that automated travel agents. And here I was going directly to consumers. And in the beginning, Travelocity, you could make a booking, but you couldn't buy a ticket. You had to refer that ticket to a local travel agent. But they weren't really doing a very good job with it. They didn't understand the internet. So I convinced the company that we should open our own travel company. And we did. And that was a huge problem internally and with our customers. And we finally, after a few years, my boss called for a debate. And we had a debate among all the senior officers of Sabre, should we keep it, should we sell it? I was not allowed to participate. And they ended up saying we should keep it, 'cause we could have sold it for a couple hundred million bucks. And I asked my boss years later, What would he have done if they said sell it? He said, well, I would've found a way to get around that, but I wanted to get it all out on the table. And once that happened, everybody had had their kind of session to talk bad stuff and they got behind it. So, but I also, you know, moved out of the building, created my own culture, didn't use their IT or purchasing or a whole bunch of things that would've slowed me down.

Yeah, it's tough. Big companies can be really amazing.

Entrepreneurship— I have a book on it called On Innovation, available on Amazon, and it's all about intrapreneurship and how it's different than entrepreneurship.

Got it. I look forward to that. I'm going to pick that one up today, as a matter of fact. Got a camping trip this weekend I'm going to be on, and I'm going to be reading that book for sure.

It's, uh, all 3 and 4 page chapters. It's like a cookbook. It's lot 72 little lessons, so you can read it whenever.

That's cool. After Travelocity, you co-founded Kayak.com. I was a user of that. I remember it. It was a revolutionary tool. It became one of the most successful travel startups in history. What made Kayak different, and what did you learn about building a second revolutionary company?

Well, Kayak was very different because it was a VC-backed startup, so I didn't have those corporate problems. We moved much faster and the VCs were really into risk-taking. So for example, we proposed this idea, we're gonna use search for travel and we're gonna deliver American Airlines customers to the last page on your website where they just have to put in the name. They already will have shopped and we're gonna convert way higher than Google. They said, that's a great idea, but we're not gonna pay you. Really? No, we're not gonna pay you.. And most of the airlines didn't. The hotels did. And so our board said, just keep sending them traffic. And we sent the traffic, and we sent the traffic, and we sent the traffic. And one day we turned it off, and they called up and said, where's the traffic? We said, same place your money is, dude. Uh, then they paid. So I don't know if we invented ransomware, but you know, they were willing to take that risk to build a product Because there's an old saying, if the startup gets the distribution before the incumbent gets the innovation, the startup wins. And we nailed the distribution and then, you know, eventually worth almost $2 billion.

Amazing story. You founded 5 startups and served on over 20 boards. What common mistakes do you see founders make when they confuse growth with impact?

Well, you know, we're gonna talk a little later. I'm chairman of another AI startup. And I was talking to the CEO yesterday and we've got great contracts with the biggest travel companies. We're growing well. And my job as chairman to make them look at the future, you say, okay, who's our competition? And frankly, I think our competition isn't another startup. It's the evolution of AI. We've got to stay ahead of it. We have to do more things. We have to do so many things for our customers. They don't dare throw us out. And continue to listen to new ideas. And, you know, he's focused on growth and revenue, and I'm focused on the next growth and revenue. So, you have to keep your head up and look at the horizon sometimes and get out of the day-to-day, particularly in SaaS where, yeah, I've done the deal, but now it's about getting the transactions.

Yeah, that sounds right to me. You've written a book about the tension between innovation and disruption. How do leaders build organizations that can disrupt markets without losing sight of the people they serve?

Well, I don't think you can disrupt a market without being hand in hand with a customer. And sometimes people fall in love with their idea. So at Kayak, we were at the beginning of the mobile revolution. Cell phones were just really taking off, smartphones. And we thought it would be about, oh, the meeting ran late, I need a later flight, or I gotta stay the night, or the meeting got out early. So it was all about immediacy. But we really listened and all of our customer emails went to the engineers. No customer service, just went to the engineers. So they really had to listen. Turns out that people were using mobile just like the desktop. And of course that's common knowledge today, but it wasn't back then. And we rewrote the product quickly and became the biggest travel app in the world for mobile at the time because we listened. So, you know, it's fine to put something out there, but you gotta prototype and you gotta listen and you shouldn't fall in love with your prototype. If they call the baby ugly, it is ugly. Doesn't matter what you think.

Yeah. You're deeply engaged now in the AI space as a speaker and an advisor, and we talked about that a little earlier, but in your view, what does responsible AI adoption look like for mid-market companies and what should leaders be watching out for?

Well, I think first they have to use it themselves. AI isn't something you can delegate. And, you know, your team members are probably already using it. You have to use it more than they do. Take a course, you know, spend your time on Google or Microsoft or Anthropic or whatever. And you need to use it to fix your costs clearly because your competitors will, but you can't win doing that. So you really need to think about how do I deploy it in my products? How do I build it in? And maybe you can't do that on your own, but I was just talking to a client who is a big SaaS company, runs ERP systems and lots of others for companies, and they're helping their clients deploy AI and deploy AI agents in their business and make them more AI-first. Because it's changing every business. But you can't win just on cost. You have to use AI to increase revenue as well.

Yeah, and also increase efficiency. I mean, because you're—

well, efficiency is fine, but that's cost. That's great, you know, that's the cost side. You need to use it, you know, in marketing and legal, in quality control and manufacturing, all that. But you also have to say, well, you know, like we've done How can I use AI to make a booking, you know, as easy as ordering a pizza?

Right.

You've got to figure out, or hey, I need to use it in customer service or to help my customer service agents answer faster and better.

Right. Makes sense. As someone who spent 24 years inside one of the largest technology companies in the world before building startups, how do you balance the precision of systems with the importance of the human connection?

Well, human connection is still really important. You know, I spent my life building online tools that eliminated a lot of travel agents, but of all things, my daughter is a travel agent. So, um, but she's a high-end travel agent in Beverly Hills working with stars and wealthy clients. And what we learned at Travelocity is the more expensive a product is, the less likely somebody's going to buy it online. They want advice. Right? You may have trade stocks on your own, but you have a financial advisor. You know, you might have a woodshop in your garage, but you probably don't build your own furniture. So there are levels of that, you know, where I want AI to help, but I don't necessarily want it for everything. I'm building a voice product in the travel company, and it's got what I call off-ramp. So if you've got a 10-minute hold time, The AI will say, well, you know, Alan, tell me where you're going and what you want, and I'll give that to the agent, right? Which never seems to work. But also it's going to say, you know, while you're waiting, I've got 3 suggestions for you. Here's some flights you could take, and if you'd like, I'll text them to you. If you like them, just press the button. So you give the person a choice. And if I have to wait 10 minutes, I'd probably rather talk to a robot. Right?

Right.

Unless it's so complicated, I don't think, or I want to discuss the experience. Right? So you have to balance when people want speed and efficiency and when they want the human connection.

Yeah, it makes total sense. I want to shift gears a little bit. You're currently advising GeoSure, which focuses on travel safety through AI and data. I'm intrigued by this. I really want to hear more. Why is this mission important to you? And what does it represent about where technology can genuinely serve people?

This is fascinating. They have taken hundreds of data sources to determine the safety of the area of where you're going down to a zip code. And it's not just, is this area around my hotel in, you know, name a South American country, safe? But I'm Black and gay, is it safe for me, right? And because it depends, right? Whatever country you're in, whatever you know, your ethnicity or your preferences may make you safe or unsafe. So it's a very important thing for corporations. They have duty of care, they need it, but also individual travelers need it. And it's just great that they're putting all these databases into the big AI blender and are able to answer those, you know, where should I jog around this hotel? I did that recently in a foreign country. I didn't jog, I walked. But anyway, um, it's really fascinating. So I, I think it's a great use of technology.

I mean, that's great use of AI. I mean, to create something that adds safety to your life that you wouldn't have otherwise. And I can't imagine a better use of AI.

Well, in fact, you know, we're talking to realty companies because when people are looking to buy a house, they want to know how safe the neighborhood is. We can do that.

Yeah. And especially if it's specific to your—

yeah, your race, religion, preferences, whatever it is.

Absolutely.

People have biases. Biases. We have to recognize that. Hey, I said biases too, but you know, it's important to you. That's what's so cool about the personalization of AI. You know, I watch Anthropic or GPT get to know more about me and make more better recommendations. Google never did that, and we're doing the same thing in travel.

Yeah, tell me about Amgen AI. I'm really intrigued by this one as well. This is the new project that you're chairman of, right? Really love to hear details about that.

Well, you know, I, I had The chairman of IBM called me 10 years ago and said, would I come and teach IBM Watson about travel? And that led into an IBM-funded travel startup, which worked awesomely and failed because customers were just not ready for AI. They didn't see it. I saw it. I see things early. So with Amgen, what we're doing is we found, believe it or not, that about 20% of corporate reservations are made via email. People send an email saying, I want to go to New York tomorrow, stay at the Hilton, come back Friday. Book it. Well, that results in a lot of ping-pong emails and screenshots and garbage. We just read that email, look at your travel policy, look at your preferences, look at your past trips, and say, Alan, here are 3 flights that are perfect for you. We also are automating group travel. So groups of thousands of people, that's all that's been done with spreadsheets and humans. It takes weeks for them to book it. We do it in minutes. We can make a booking through Slack, we can make a booking through Teams. It's all natural language, and that's the way the world's going. And that's what my old startup did. You know, I want to go to the Caribbean with my family, play golf, have a great spa and things for kids to do. You can't ask that question on any travel website today, but you're going to be able to now. You can ask it to ChatGPT and book it separately. But at Amgen, you know, we're bringing all that to life.

And that's mostly for corporate?

Yeah, Amgen's corporate-based. Yeah, today.

Okay.

But it's happening on the, the consumer side as well. The guys who started Kayak, one of whom still works at Booking.com, now have a new AI travel startup that Booking is funding outside of Booking.com because they have decided we can't change fast enough inside. We're gonna fund an external startup to come and tap us on the shoulder and say, guys, you gotta change.

What's that called?

I don't remember. I think it's Lola. I think it might be Lola.

Lola.

It's not running yet. Just started. And, but it's really interesting. In fact, Airbnb, Chesky is doing the same thing. His AI startup is outside. If it fails, it doesn't wanna affect his P&L. But that's kind of like Travelocity. It was a carve-out. Right? We built it inside and then took it public outside. That's a good strategy.

You know, mentorship's really important to me personally, and I think it's really important to do that for others. You've mentored countless entrepreneurs over the years. What's the most common piece of advice you give most people that resist hearing it?

They resist hearing their baby is ugly. Um, they resist making the pivot. Amgen's a complete pivot from a failed company that tried to do consumer AI. You know, it's about listening to your coach or your chairman or your board and understanding they have a lot of wisdom based on experience. I want my entrepreneurs to make brand new mistakes, not ones I already made. And sure, the world changes and you gotta be cognizant of that and they can come back and say, you know, You're out of date, you don't get it. And leaders have to listen to that. I was in a group yesterday where a leader was telling a story of a big telecom company and he had a marketing person who was probably 20 years younger than he was explaining a marketing program in Latin America for people of her age. And he said, "Boy, I don't like that idea at all." She said, "You're not the target market, dude.

You don't understand." You shouldn't like it.

Yeah, so there is that tension. Between, you know, if I'm not the target market of some of the products that I advise on, so I've got to shut up about that. But if I say, don't open in Europe like this, you don't understand, you've never been abroad, you need people on the ground, you need to understand the legal aspects, you can't run it from the US, come on, you know, I'm gonna rain on their parade, right? I want them to again make new mistakes.

Yeah, absolutely. What does leadership look like when the goal isn't just shareholder value but genuine impact on people's lives?

Well, I'm not sure that leadership itself is different, but I think what happens to you is different. You know, how it gives back to you as a leader. I'm chairman of a Boys and Girls Camp in— I was until recently— in International Falls, Minnesota. We take 500 kids a summer. And take them out in the woods and get them off their phones. And 25% of them are scholarship kids. They don't pay anything for it. And we just want to get them out of the inner city. And that's just wonderful for me because I love that experience and I love sharing it. But I also love broadening the audience into people who just, you know, I was with a group of inner city kids from Cincinnati who spent the night in a tent in pouring rain. And I thought, oh, they're going to go in the building. And they came out and said, That was awesome. We could read by the lightning and the rain was so cool. And they loved it. I have another friend who worked startup with me. He formed a company called WriteGift and they help charities allow donors to give in kind. So rather than giving money to an unhoused person, you could give them a blanket or you could give them, you know, food. So there are lots of choices. Hard for charities to do that. So they build all the pipelines into Walmart and Costco and Amazon, and they package it and ship it and do all that stuff. And they're a, they're a for-profit company, but, you know, they really did it for the impact. And in fact, I can even invest in that from a foundation that I run because it has a charitable purpose, right?

Social enterprises are amazing vehicles, and so I'm a big fan.

Yeah, so I think it's great for me. I mean, I love, you know, at this point, I mean, my lectures and speaking are about innovation, disruption, and AI, but it's all about because I want companies to be more innovative. You know, nobody wants a historical marker. Here was the Joe's Company. They succeeded and employed a lot of people till they didn't. You know, you gotta change. And so I love helping that. I love helping entrepreneurs. 'Cause it keeps me young and I learn about a lot of things and help make new mistakes. I was chairman of the Shakespeare Festival here. We put 15,000 people a summer through Shakespeare on the Beach in Lake Tahoe, you know? And that's, that's great. But we also teach Shakespeare in schools, which schools don't do anymore. So we have people who go out and do that. At our camp, we teach canoe building in schools. So it's STEM, but they also end up with a canoe on the water. So that stuff is very rewarding. And I've learned to make wooden toys for my 6 grandkids, so that's what we're gonna do. Now I'm doing it with a charity who makes 1,000 toys in the winter for kids all over the Reno area.

That right there is a whole nother episode that I want to do. It's really fun with you and the other people in that organization that could really express how much impact they're having to these kids.

Yeah, it's, you know, kids are so important and You know, they learn faster and differently than we did. But, you know, grandpas still have lessons for sure.

Well, you founded companies, written books, spoken on stages around the world. When you strip all of that away, what do you think the next generation of builders need to take from your story?

Well, you know, I think we only learn strong lessons from failure. And, you know, in Silicon Valley, we look for people who failed before, but they got up again and learned from it. And, you know, why do sports teams watch the film of the fumble over and over again? Not to assign blame, but to ensure victory. So, it's really about learning and it really is about curiosity. If you're not a curious person, don't do a startup. And don't get into innovation. You've gotta be curious, you've gotta be tough. You always have to be selling 'cause you're selling your idea and yourself and the company and the team. But, you know, it's about trying and failing and listening to the customer and pivoting. At Travelocity, we had a British phone booth in the hall. If you picked up the phone, you could listen to customer service. It reminded people that everybody in the company from the guy in the mailroom legal department, any department had to listen to 2 customer service calls a month. And at staff meetings say, how could we have done that better? And why is our product so lousy they had to call? And so it involved everybody in the customer's pain. You've gotta listen. And in this hyper-connected world, there are lots of ways to listen. And AI can listen for you. But if you don't listen, then you don't change. There's a wonderful guy called the Amazon Whisperer in New York. He runs one of those electronic shops on 3rd Avenue. He reads Amazon reviews of electronic products, takes the ones with the worst reviews, and builds products that don't have those faults. What a wonderful way to look at product development.

I mean, that's great disruption right there.

Yeah, let's know what sucks and fix it.

Most definitely.

That's what we did at Kayak.

Yeah. Terry, what are you most excited about right now? Projects, partnerships, conversations you're a part of, and what do you think will matter in 10 years?

Well, I'm real excited about the positive impact of AI. You know, I'm worried about the negative impact. I'm on the board of two cybersecurity companies. You know, I think we do need regulation. I think this is a technology that It can change the world for good or bad, but I'm excited about the good part. You know, look, the Industrial Revolution was really hard on people, but hey, we've been through it again. What's manufacturing? Less than 10% of our economy now. We've changed again. We're going to change again. So I think using AI to improve our productivity, realizing that, you know, we're not bringing enough new people into the country, our birth rate is down, we need to be more productive. We need AI to help us. I'm very excited about what it could do and about, you know, the next technologies. Quantum, right? Awesome. Nuclear fusion, you know, could change the world. What do you think if we had free power? I mean, there are some very exciting things that could change the world for good. And yeah, yeah, with all the negativity that's out there in the world, You know, I try to think about what's right with the world and how I can help it be more right.

Couldn't agree more. Well, we've come to the end of the episode. I'm so thankful to have you, Terry. Thank you.

My pleasure. It was great, great fun. And, you know, people want to learn more about me, it's terryjones.com, and my books are on Amazon. And I'm, you know, still an active speaker and mentor.

Can't wait to dive into the book you mentioned earlier. I will be on that right away.

Second one is called Disruption Off. How to not be disrupted and become the disruptor yourself.

Very cool. Terry, what you've built for 4 decades isn't just about a portfolio of companies. It's a blueprint for what's possible when you combine vision and responsibility, courage with generosity. Travelocity opened the door to millions of people who had never had that kind of access. Kayak put the power of informed decisions into the hands of everyday travelers. And the work you continue to do—advising, writing, speaking, mentoring—it's proof that legacy isn't something you build once, it's something you keep building. To our Legacy All-Stars audience, I encourage you to pick up Terry's books. I definitely will be doing so. Follow his insight at TB Jones or at TerryJones.com. Either one, TB Jones or Terry Jones.

I have them both.

Yeah, and then carry this conversation forward. The future belongs to those who build it with intention. Terry, again, thank you so much. I'm Alan Pavlosky, signing off for Legacy All-Stars. See you next time.