Live From ILTM: Virtuoso CEO Matthew Upchurch on Humanizing the Exceptional in an Age of AI

For more than four decades, Matthew Upchurch has been a driving force behind how high-end travel is sold, experienced, and understood. As CEO of ⁠Virtuoso⁠ , one of the world’s leading luxury travel networks, he’s championed human connection in an increasingly digital world and advocated for the enduring value of trusted advisors and transformative, purpose-driven travel.

In this ILTM episode, recorded live in Cannes, Afar cofounder Joe Diaz sits down with Matthew to discuss how the luxury sector is evolving, what personalization really means today, and where he sees the next opportunities for meaningful travel experiences.

The conversation explores how AI is reshaping the advisor role, why debriefing clients is the most underrated skill in the business, and how intergenerational collaboration is breathing new life into travel advising.

Transcript

Joe Diaz: I’m Joe Diaz, an Afar cofounder, and welcome to View From Afar, a podcast that spotlights the people and the ideas shaping the future of travel. In this special series, I’m coming to you live from ILTM, one of the most important travel shows that happens every year. ILTM stands for the International Luxury Travel Market, and the show takes place in a fittingly luxurious city, Cannes, France. The conversations that happen here influence how we think about travel for years to come.

Afar editor in chief Julia Cosgrove and I sat down with leaders across the travel industry, from visionary hoteliers to destination innovators, to discuss the trends, challenges, and ideas that are driving hospitality forward. We want to understand what truly motivates these leaders—how their personal stories, values, and visions shape the experiences they create for travelers. Be sure to follow the show to hear all our conversations from ILTM.

In this episode, I’m sitting down with Matthew Upchurch, the CEO of Virtuoso, one of the world’s leading luxury travel networks. For more than four decades, Matthew has been a driving force behind how high‑end travel is sold, experienced, and understood. Under his leadership, Virtuoso has grown into a global community of advisors, partners, and travelers. He’s been a vocal advocate for human connection in an increasingly digital world, championing the role of trusted advisors and the enduring value of transformative, purpose‑driven travel. We talk about how the luxury sector is evolving, what personalization really means today, and where he sees the next opportunities for meaningful travel experiences.

Well, Matthew [of] Virtuoso, welcome to the Afar apartment here in ILTM Cannes. Excited to have you with us today. You often describe Virtuoso as being in the relationship business. So, in our world today of AI and algorithms, how does that change the calculus in the context of human connection?

Matthew Upchurch: Well, first of all, I, thank you for having me. It’s great to see you, as always. I’m super excited. I’ve never been more excited. I mean, it’s so funny. With every new wave of technology, the demise of human connection and the advisor has been predicted, right? So I honestly can’t remember how long ago, but it’s at least 10 to 15 years ago. So probably my most quoted quote of mine is something that I started talking about many, many years ago that encapsulates it: Automate the predictable so that you can humanize the exceptional.

I’ve always been a huge fan of technology, but there’s basically two variations of technological application: one is to gain efficiency, which can be a euphemism for how many human beings can be removed from the process so we can increase our margins or speed or whatever it is; and the other is the application of technology to enhance who we are as humans, what we do, what makes us special. And so, you know, I talked about that back, you know, when the OTAs [online travel agencies] were born, when social media was born, I mean, all this kind of stuff. But what AI is going to become and is the mother of all “automate the predictable,” right?

What’s super interesting now is, What does it mean to humanize the exceptional? So we had Will Guidara as our keynote this year, and it was awesome because he had such a great line, which is, you know, “You know how everybody talks about It’s all about service? No, it’s all about hospitality.” But I love his definition of it. Service is that thing you do. Hospitality is how you make somebody feel doing that thing you do. So, actually, service can be replaced. And in some cases, automation and things like that can be better service, quite frankly, than human service.

So I’m super excited. And we’re going into—there’s all kinds of things that [we] are doing because now the ability of advisors to leverage AI . . . I mean, so many people—oh, you know, last night a fairly senior person said, “We’re going to Brazil.” And my daughters, who are in their 20s, said, “Dad, we’ve been using this agency—give us an hour.” And they came back with this incredible itinerary and all that. Yeah, that’s great, but who are the people behind it? It’s no longer just “Can you find a guide”—they don’t have my guide, and they don’t have the relationships that we have. So I’m very, very bullish.

Joe: So give me an example. Humanizing the exceptional is an easy concept to understand for all those travel advisors that are listening to this, even entrepreneurs in the service and hospitality business. [What are] some examples you’ve seen from advisors that do a great job of encapsulating that idea of humanizing the exceptional?

Matthew: I think a lot of it has to do with just a series of pragmatic things, like, for example, if an advisor ever says, “Oh my God, I lost this booking” or whatever. And I said, “Well, did you use your Virtuoso contact? Did you send them a message? Did you tell them this? What are the things you can do to make someone feel seen?” Will again said, you know, my definition of luxury is You see me. What are you doing to help transmit that emotion? Right. What are you doing?

I’ve always told advisors that if you tell people you book travel, you’ve literally lost before you started. And I could sit here and give you some specific examples. Instead, I’m a big believer in frameworks. So this is not new. But it’s interesting how every so many years there are new tools, new things, whatever that help you build that, use this framework. I want to challenge all advisors to say the holistic nature of what you do. What do you do before they travel? What do you do while they’re traveling? And what do you do after they travel? And ironically, a lot of our advisors—and we have this data from consumer research—the number one thing that sophisticated travelers tell us separates a transactional travel agent from a trusted travel advisor is the quality of the debrief. Whatever practical way, right. It’s got to be practical to the customer. I don’t want to do it in a one‑hour interview. But if I can then feel how that improves and we have a learning relationship, I as a consumer have actually put in my capital into this relationship, and it becomes stickier and stickier and stickier over time, and also the leveraging of our personal relationships. Right.

And then another one that I think is a big one that we’ve been working on is a lot of advisors do this naturally, but it’s the difference between inspiration. So for example, a lot of advisors again with this whole debrief thing, they talk about how do I help people be more conscious about what they’re doing in the future? How do I help take what they love, introduce other things so that people can be a little bit more purposeful in having a framework of how to optimize their most valuable nonrenewable asset, their free leisure time?

Joe: I love the idea of the debrief. I think it’s a powerful one. This idea of being able to circle back and really get into your client’s life, understanding what they love, what they didn’t, and being able to just continue to take that to the next level. And I think people, especially today, forget, like they get the business. But that’s just the beginning.

Matthew: I think one of the most powerful things about why I’ve enjoyed the Virtuoso community is that we truly believe there’s more in sharing than there is in keeping things to yourself.

Why do tech companies always talk in terms of domination? because it’s actually possible to be 90 percent of search. But whenever you’re involved in anything that’s human‑connection‑dependent, collaboration is the greatest way to succeed, because anything that’s human dependent, it’s impossible to be 80 percent right. I’ll give you a real example. One of our top members, and Sculley was a great educator, right? People saying, yeah, but when my clients come back and say, you know, how was your trip? Some of them don’t want to say anything or they’re kind of quiet or whatever. And she said, “Because you’re asking the wrong question.” That’s very intimate; certain personality types will run with it. A lot of personalities won’t. Because here’s the better question: “If you could change one thing about that trip, what would it be?” Way easier, way more focused. It opens up Pandora’s box and creates a safe space. So that’s very pragmatic, And it’s funny because years ago I was quoted in USA Today where I said, you know, what clients are impressed about now are not answers. It’s a really good question, which is kind of funny because now it’s called prompt engineering.

Joe: Asking a really good question is so powerful, it can open up a conversation in ways that you didn’t think possible.

Matthew: Exactly.

Joe: And so the advisor today wears many hats—strategist, sometimes therapist, planner, connector, relationship builder. What skills, as you kind of look at the tea leaves for the next five years, that really stick out to you for what a great advisor needs to embody and take with them?

Matthew: You know, it’s interesting. I have a thesis that’s really important going into 2026, and that is: prior to the GDS, the airline GDS—

Joe: And can you just quickly define that?

Matthew: They were the airline reservation systems. The travel agents in the ’50s and ’60s actually were true travel advisors. Do you know that more people booked direct with partners in the ‘50s and ‘60s than they do today? Because there were no OTAs. All travel was luxury. PanAm was white‑glove service. There wasn’t price complexity. Airfares were regulated by governments. You flew on PanAm, you flew on BOAC. It was the same rate. So to be a travel agent in the ’50s and ’60s meant, “Why do I need you? I know Claridge’s customer, I know Ronald Jones, GM or whatever.” So community knowledge, relationships. Most innovation is not invention. It’s kind of looking at how things change language, new skill sets, new things, new technologies, resequencing things. Right?

So the reason I say that is then the GDS came along, thousands of people were hired as travel agents, but really they were human biological interfaces to the scripting language. And the number of travel agencies went from 4,000 to 44,000. Then the OTAs were born. There’s a forest fire of—and I don’t mean to be rude or unkind, but a forest fire of people that were called travel agents that were human ATMs, and they get replaced. Right. But the people who were truly advisors not only did not get replaced, they started to build what they’re doing.

Then we had in the early 2000s when iPhone and social media were born, all of a sudden the profession got unchained from the desk. Then we started attracting a whole new level of professional that didn’t want to sit in an office. And I would say for the last 20 years, the bias of a travel advisor has been right‑brained. So imagine if I have to learn scripting language. It’s like court reporting. I was left‑brain biased in that era. Now it’s been 20 years. Right‑brained social skills, this creativity. Everybody has to have a little bit of right‑brain, left‑brain skills. Right.

I actually think one of the things that is a really cool idea for the future is I think we need to do for the left‑brain side of the business what we did for travel advisors. I don’t know whether they’re logistics people, whatever, but I think unique‑ability teams are going to become really important because if I’m really good at relationships and this, that, and the other, I’m probably normally not as good on the logistics side or the process side or whatever. That’s why I’m a big believer: What is the framework? What is the front stage? How do you make people feel? How do you interact [with] all that? What’s the backstage part? Because if you get a really great right‑brained person partnered with a really, really great left‑brained person, that’s powerful. It’s not arithmetic. It’s literally—and I love the concept of unique ability because in unique ability, you can have something that is in your excellence quadrant, meaning that you’re known for it, you get paid a lot of money, blah blah blah. And then you take the same superlatives and put it in unique ability. Well, what’s the difference? That which is in your quadrant, no matter how good you are at doing it, when you do it, it drains you of energy. Now it might be a little drain or a big drain, but it’s a drain. That which is your unique ability, when you do it, it gives you energy.

Joe: So recharge.

Matthew: Recharge your—

Joe: Batteries. Yeah.

Matthew: So the concept of unique ability is how can I build a practice, a business around the concept of creating unique‑ability teams knowing it’s an ideal you’ll never reach—the ideal where the greatest number of working possible hours of every person on the team is in their unique ability. And if you do that right, it’s freaking magic.

Joe: You talked a little, you know, about this idea of automating the predictable. Maybe another dimension too, especially given the world we live in, is being able to delegate more and outsource things you’re not good at, right?

Matthew: Exactly. I’m turning 64 next year. I’ve been doing this for 40 years. I am so grateful to the people that raised me that helped me. But one person who has become a good friend and I love him is Chip Conley. Chip wrote The Wisdom at Work: The Making of the Modern Elder.

One of the other subjects I love is intergenerational collaboration. So Chip makes this concept that I actually totally agree with. When you mix multi‑generational—younger people, older people, whatever—and you create a really great environment, it creates magic because, as Chip said in that book, “I’ll lend you some of my EQ for some of your DQ.” Right? My emotional intelligence for your digital intelligence. And what I found is, as Virtuoso focused on bringing new talent for the last 20‑some odd years, what I didn’t fully expect was that the arrival of new, younger talent extended the lifetime of our veterans because all of a sudden it’s like, this is exciting. And now all of a sudden I have, you know, and whether it’s younger people, my—I never thought my daughter would quit her job at Pfizer and move back to Michigan. She said, “Oh, Mom, I’ll never do what you do.” Hoteliers 20 years ago wouldn’t leave X brand to be a trap. I mean, I just literally met with one: “Oh, yeah, I was a revenue manager for XYZ hotel group and now I’m on this side.” Super fun.

Joe: There’s a lot of transformation that has happened at Virtuoso Travel Week that you host every year in Las Vegas. But as someone who regularly attends, I think that’s one of the things I’ve noticed the most. If you ask what’s changed the most at Travel Week in the last decade, it’s the next generation of advisors. It’s a younger group that brings a new energy, a new perspective, and that just shows you the vibrancy of the space that you get to play in.

Matthew: The thing is that it’s not a zero‑sum game. So here’s what’s interesting. I had one of our members—nameless, but he’s very funny. I think we were just coming out of the pandemic. He goes, “Matthew, would you tell some of our older members, for God’s sake, quit talking about the millennials like they’re kids, for Pete’s sake. They have kids.” “Yeah, right. Yeah, they have kids.” And I said, you know, you’re right, etcetera. I said, but you know what? Right now, millennials are a major part of the workforce or whatever. But you know who the wealthiest cohort of American consumers in the next 15 years will be? Single women over 65.

Joe: Wow.

Matthew: Bar none. So the point is, what I always tell our partners, everybody, is that it’s not millennials versus this whatever. I’m now starting to talk to not the GMs, not the brands, but like the hotel owners, the revenue. I said, because one of the reasons we’re doing so well is that the diversity of our advisors mirrors the diversity of our clients.

So the reality is, why do we have Gen Z clients? Because we have Gen Z advisors. Why do we have amazing matriarchs that are in their 70s and 80s and are incredible? And by the way, spending a quarter of a million, half a million dollars a year taking the whole family somewhere or whatever, because we have amazing matriarchs and people like to identify with that.

Joe: Let’s talk a little bit about that traveler. Obviously, the last five years has been pretty insane. I think it’s fair to say we’re in a postpandemic boom when it comes to higher‑end luxury travel. What are some of the things you and your team are seeing in terms of the changes that the affluent traveler, the luxury traveler—somebody that likes to travel at that level—is asking for that they weren’t necessarily asking for in 2019? Have there been any remarkable shifts for you? Is it more of the same? What’s your team seeing when it comes to that idea?

Matthew: I’m a big framework person, right? I love frameworks because in order to be creative, really good frameworks give you a language and a way to be creative. So I would start with the fundamental thing that is accelerated, which is what I call the creative tension of the sophisticated, luxury experiential traveler. And that is the creative tension between wanting to go back to places I adore and love and feel a connection with and the desire to see something new.

And so what’s interesting about that is if it is the place I’ve been going to or whatever, what is interesting there is what’s new. How do I see it differently? How do I engage differently? You know, we’re expanding in the Middle East, the Middle Eastern luxury. The younger Middle Eastern luxury customer is actually turning out to be a great new thing for us, because a lot of their parents, they’d go to the same hotel in London, take over the top floor with the same entourage year after year after year. Well, you don’t need an advisor for that, right? So exploration.

Joe: I’ll be your advisor if you’re booking that.

Matthew: Yeah. Well, they tended not to, but now they are. But it’s interesting. That has led to what I call fusion travel, right? The mixing. One of my favorite examples is my love of Venice and then knowing that it’s a two‑hour train ride to Slovenia. Right. So it’s kind of like fusion cuisine, things like that.

We have a new trend called FOMO to slo‑mo, which is the fact that there really is this kind of awareness: There are certain places in the world that are rapidly changing for multiple reasons, and I want to get there. But then when I get there, I want to be really intentional because I’m not sure it’ll stay the same. So FOMO to slo‑mo is a really interesting one.

I think the thing that’s important about all this is that consumers and travelers today have many travel personas, right? There is no such thing as Matthew the Traveler. Matthew has multiple personas. But I also think it’s interesting that the role of an advisor today, when people are so smart, so connected, have access, is also inspiration, right? It’s getting people to take time.

So one of my favorite kind of long‑term processes is: Why would you have a wealth advisor in your life? To have a conscious, strategic plan to optimize your financial assets. Who’s going to help inspire you to slow down a little bit? Let’s be a little more intentional, to have a framework about how being a little bit more intentional and purposeful about having a strategy to optimize your most valuable nonrenewable asset, your free leisure time. Why the hell would you have a collaborator on money and not on your time? Oh, because I’m spontaneous. I mean, I come from Mexico originally, right? Like all my Mexican friends, like, “Dude, do you realize that 24 hours is advanced planning?” But I said, it’s not about having a plan that you execute. It’s about having a framework of thinking. So I actually think that’s another incredible opportunity: How do you get your customers to think differently, to think more purposefully, more intentionally?

Joe: On that note, as we wrap up, I know you value and put a lot of time into leadership and building your leadership skills. You’ve been leading Virtuoso now for what, close to four decades?

Matthew: Next year will be 40 years.

Joe: Years, you know. Congratulations. That’s amazing. Could you just talk a little bit about how your leadership style has changed from, you know, 40 years ago to today, and are there still any nonnegotiables for you?

Matthew: You know, it’s interesting when I kind of look back on it, it starts with a deep belief in collaboration. I did a speech a few years ago. I said, you know, I actually think my core shtick hasn’t changed since I ran for class president in the eighth grade, which was pretty much like, “Hey, I will work my butt off for you as long as we’re in it together.”

Joe: Did you get elected?

Matthew: I did get elected. I did get elected. I did get elected. But then it’s always been that. Which is why I love the [unclear]. But I think the thing that, you know, my grandfather and my dad both were like, be a voracious reader and a voracious learner. And so I’ve always—I think I’ve really become a lover of—because I’m like that dog in the movie Up: squirrel. Squirrel. Like I’m easily distracted.

So I think from a leadership perspective, I would say that frameworks have become a very important part of my life. I knew that having a good culture was a thing, but for example, Patrick Lencioni, who wrote The Advantage and The Five Dysfunctions of a Team, that was a game changer for me. That framework was really good because I loved the thesis of that whole book, which is being smart has become a commodity. You have to be organizationally healthy in order to succeed. And so for me, the ability to get human beings to have healthy conflict, the ability to agree to disagree—so I think my leadership has evolved from the perspective of constantly wanting to learn and constantly trying to tweak frameworks. Just because I say something doesn’t mean people understand it, right. How to ask better questions. How to build better teams that complement each other. That’s probably the most important thing that I’ve learned.

Joe: Well, thank you for teaching us today. It’s been a privilege. It’s always fun. I feel like we could do this for two hours. And so thank you, Matthew, and hopefully get you on soon.

Matthew: Thank you.

Joe: Thanks for joining us for this special episode of View From Afar, recorded live at ILTM in Cannes. In the show notes, you’ll find links to everything we discussed today, as well as Virtuoso’s website and social media handles. And be sure to follow along this week to hear more interviews with industry experts.

You can find more Views From Afar on Afar.com and be sure to follow us on Instagram and TikTok. We’re @AfarMedia. If you’ve enjoyed today’s exploration, I hope you’ll come back for more great interviews. Subscribing always makes that easy. And be sure to rate and review the show on your favorite podcast platform. It helps other travelers find it.

This has been View From Afar, a production of Afar Media. The podcast is produced by Aislyn Greene and Nikki Galteland with assistance from Jenn Flowers, Julia Cosgrove, and Joe Diaz. Music composition from Epidemic Sound.

This podcast is part of the Airwave Media Podcast Network. Visit Airwave Media to listen and subscribe to its other fine shows like Culture Kids and The Explorers Podcast.