Early on in our conversation, Matthew Upchurch had a simple yet profound statement that resonated deeply and stuck with me long after our conversation came to a close, “Travel is the only thing that makes you richer.” It is not a slogan or something that he leverages for professional gain, it is simply a grounding pillar that has followed him throughout his career. As a leader, this saying has become the ethos behind four decades of leadership at Virtuoso, the global luxury travel network he began shaping at just 24-years-old. Since then, Matthew has grown Virtuoso into one of the most influential high-end travel brands.
Growing up in Mexico, raised by a father who was deeply ingrained in the travel space, Upchurch leveraged the knowledge he gained from his father and drilled home his personal ethos, the idea of connection, human connection to be specific to build his luxury travel empire. We touched on these topics quite a bit in our conversation, what I thought would be a clear trajectory of business expansion and leadership success with just the right dose of travel turned into a much larger conversation about the power of human connection.
Long before AI entered the mainstream, Upchurch was preparing for a world driven by efficiency. At this point he hit me with another bar that is applicable to many of us, regardless of our industry. His philosophy is simple: “Automate the predictable so that you can humanize the exceptional.” In other words, use technology to handle the transactional so that people can focus on what actually creates value, things like having good judgment, seeking out authentic chemistry, and building actual trust. In his view, the modern travel advisor is not just a booker behind a screen, they are a team and well oiled machine that is always two steps ahead. The type that has already called the car service to change destinations before a storm rolls in, or knows your dog will need a bed just as plush as your own, and makes sure to call ahead for it. Rather than waiting for the inevitable bump in the road, these could-be issues become invisible, quietly taken care of behind the scenes.
For Upchurch, the differentiator is culture. Relationships are not an added bonus, they are the foundation on which Virtuoso is built on. When advisors bring this level of genuine human connections to their relationships with partners, the experience shifts from service to stewardship. In an era defined by speed and digital noise, he sees travel as one of the last remaining spaces where attention is reclaimed, families reconnect, and memories compound rather than depreciate.
He made something abundantly clear, money can be earned, lost, and earned again, but time is irreplaceable. That belief finds its meaning in the unwavering attention to detail and ability to build upon that sort of authentic connection he spoke about. His wise sentiment being: treat your leisure time with the same intentionality as your capital. Because if travel is the only thing that makes you richer, then the true return is measured not in margins, but in meaning.
Answers to questions have been shortened for editorial clarity purposes only
When did you first realize that luxury travel would be more than just a traditional service industry—that it could be a force for economic and cultural impact?
I’m a second generation travel person. My father was one of the founders of the U.S. Tour Operators Association (USTOA), and he was one of the pioneers in opening up photographic safaris to Africa. I had first hand knowledge of that. What’s been really amazing is, over the years, when travel had good stewardship, how it could really be a force for good—both in the opportunities and the things that it did for the destinations, but also the way it opened up people’s minds.
When I was 24 years old, what is today Virtuoso, I met a group of European expat small boutique agency owners. Back in the old days, it used to be called the carriage trade—the luxury business—but it was all about how to create bespoke experiences. That was when I really first started seeing the difference between somebody that was a designer, curator, life experience guide, versus somebody who was just a booker.
If you think about the path of the modern day Travel Advisor, it’s not unlike what happened with the moniker of a stock broker. It used to be a stock broker—there were people that were just boiler room processors, and there were people that were true strategic wealth managers. Same thing inside the moniker of what was once known as a travel agent, then became a Travel Advisor.
One of the most interesting parts of the word luxury and luxury travel is that luxury used to be about fancy, and then it became more of like—this broadens my mind. It makes me a more competitive global citizen. It frankly makes me a more interesting person. It allows me to learn things and see things from different perspectives. I think that people, over time, as travel became more diverse and more interesting, really started associating it from being a luxury to a lifestyle—a really important part of developing who you are.
I always joke that around a dinner table, the two things that everybody likes to talk about the most are themselves and travel. And so when you pair the growing meaningfulness of this expenditure, and then you look at what’s happened in almost every single major disruption—economic, geopolitical, or whatever—with, of course, the pandemic being the mother of all disruptions—all of a sudden, this idea about what the value of travel really is has only been accentuated from the perspective of its intrinsic value.
What are the driving forces shifting the culture of luxury travel today? What makes people lean toward a holistic approach—toward something like Virtuoso—as opposed to just straightforward planning?
I’ve always told a good Travel Advisor: if you tell people that you book travel, you’ve literally lost before you started. Because that’s like walking into a store and me being your salesperson saying, “Hey, I know how to ring the cash register.”
The way a great Travel Advisor adds value is—what do they do before the trip? In a world where there’s infinite information, one of the things that really impresses a sophisticated traveler is a really good question. Like, you give me a really good question I hadn’t thought about.
The other one is human connection. We have invested a tremendous amount of effort in making sure that our travel advisors have personal relationships with people all over the world. So you may know Le Sirenuse in Positano, but the owner of that incredibly famous property has been coming to Virtuoso meetings for years, building all these relationships. And I talk about this concept of—you can’t take the human out of humanity. If I know you and you know me and I send you my client, you can’t help but treat them just a little bit different, a little bit better.
Then, what do you do during the trip? It’s travel—it’s not if things are going to go wrong, but when. And not just disruptions like canceled flights, but the nuances of having the right type of people on the ground and the type of relationships that allow for the fluidity of an experience that isn’t just cookie cutter. It’s kind of like the concept of pacing—if you’re in a really good restaurant, you can always tell intrusive service versus naturally fluid service. They’re reading the room, reading the energy.
And then there’s the post-travel, because the ability to exchange information creates a learning relationship that adds to the ability for an advisor and a client to evolve together. Being able to map to new destinations, new feature sets, new products—that’s something that creates what I would call the art of travel, rather than the science of travel.
When you think about success within Virtuoso, is it more financial growth, client satisfaction, long-term relationships, or something else entirely?
What was once a clerical job of a travel agent has now become a really serious, well respected profession that is also financially and personally rewarding.
The common denominator I actually see amongst our most successful advisors is not years in the business. They’re so good at what they do that the client is as afraid of the advisor firing them as the other way around.
And it’s funny, because one of the great things about the profession is, when you’re an advisor, you don’t have to deal with everybody—you have a choice. That’s why, when I’m asked to give a suggestion of an advisor by friends or people, I literally refuse to give them the name of a person. Because if the traveler doesn’t put some cognitive effort into the selection of the professional, giving the name of one person is like being in the business of promoting blind dates—they don’t normally turn out really well. If you really want a valuable, true, perfect relationship, you need to put some cognitive effort, because at the end of the day, it’s not just about knowledge. It’s about chemistry and style. In telecom, they used to call it the last mile—you can have the fastest fiber optic network in the world, but if you have a piece of copper between the switch box and your house, it doesn’t matter. Well, the last mile in a human connection-driven profession like ours is human connection.
And that value is becoming even more valuable in a world where AI can generate itineraries and do all of that. But what’s the relationship I have with my professional?
The people attracted to this profession are driven by their client set. To come back and get letters or emails from your clients saying, “Oh my gosh, that was one of the greatest experiences”—these are the most valuable moments that people have. And it actually gets even more rewarding over time.
We’ve always had this moniker that travel is the only thing that makes you richer. There are serious psychology studies about the value of travel—there’s value in the anticipation, there’s value in being in the moment. But one of the most interesting findings is that travel memories actually get stronger over time. In a lot of luxury products, human adaptation kicks in—you buy a Bentley, and within weeks or months, you get used to it and it just doesn’t seem as special as it used to be. But travel memories actually become more valuable over time, rather than what happens with other types of luxury goods.
How has the rise of AI and automation shifted the industry? Are we losing human connection?
Probably the single most famous quote of mine—and I said this almost 20 years ago, particularly in the beginning of the Internet era—is: automate the predictable so that you can humanize the exception.
As technology has gotten stronger and more ubiquitous and more intelligent, I always felt that the ability to leverage technology to spend less time on things that are rote, procedural, repeatable—so that you can actually spend more time on things that are more human, more personal—that’s been my philosophy for a long time. And AI is the mother of all “automate the predictable.” AI by definition are predictive models. That is literally the definition of AI.
So now what we’re doing is: what does it mean to humanize the exceptional? How are you going to be more intentional about that?
Will Guidara, who wrote Unreasonable Hospitality, was our keynote speaker this past year. I love his definition: service is that thing you do. Hospitality is how you make somebody feel doing that thing you do. I love the simplicity of that, but just because something is simple doesn’t actually mean it’s easy.
I think one of the things you’re going to see is people who use AI purely to increase their margins and remove costs—they’ll get a lot of efficiencies. But if they don’t really believe in the power of human connection and culture, you can already today feel the difference between going to a restaurant or a hotel where the employees are inspired by their ownership or their brand. The half life of somebody having a technological competitive edge is getting shorter and shorter. What’s going to be really difficult to replicate are really good cultures where you can feel that the people delivering the experience are genuinely excited and genuinely there.
Have major disruptions—economic downturns, global crises—shaped your philosophy? What lessons have stayed with you?
Every major disruption has only amplified what I would almost call Carpe Diem. Under the moniker of travel, it’s like: time with my family, time to introspect, time to recharge. We are starting to understand the sophistication of the way technology is used for the monetization of human attention—it’s worth trillions of dollars. And travel is one of the greatest antidotes to this.
Disruptions have made people live more in the now—and not in a fatalistic kind of way. We went from the Depression era people who thought travel was a luxury—”oh my gosh, I can’t afford that”—to now flipping it on its head and saying: “No, this is not a luxury per se. It’s what keeps me going. It’s looking forward to doing something.”
We have one of our Virtuoso members who just did her thesis at Wharton on whether travel changes the trajectory of pre-teens and teens later in life. Her primary research of actually interviewing teens and preteens found that they themselves were saying—because it’s not just the devices, it’s the ridiculously hectic life: soccer practice, hockey practice, college counseling, this, that, the other—they were literally saying, “Are you kidding me? Travel is—we’re all around the table. We’re all actually doing something.” So I think there’s a realization that travel is a natural pause, and a natural way of sharing something together that bonds you.
Is there something that keeps you awake at night—a problem you want to solve, or an uncertainty you want to prepare for?
In 2010, we hired Simon Sinek as our keynote speaker when he wrote Start With Why. I love the simplicity of that model: people buy the why you do something, and they commoditize the what.
When you live in such a fluid world, my personal belief is that you stay constantly curious, but you also hold onto those core things that you believe in. For me, it’s been the power of human connection. As an entrepreneur, one of the things I’ve always thought about is there’s this almost manic focus on the things that need to change. But what I love to focus on is: okay, these things need to change, but what maybe shouldn’t change? And not only not change, but maybe double down on it.
I feel that way about a very contrarian example—the profession of travel agent in the late 1990s. When the airlines cut commission by 50% in 1997, can you imagine being in a business where overnight, 50% of your revenue is gone? And then a couple years later, they went to zero. But you know what the airlines forgot? Who ultimately decides whether I survive or not. It’s called the client. Two years ago, American Airlines tried to basically force everybody to book the way they wanted to. Whereas the CEO of Delta Airlines says: “Our philosophy is really simple. We are where our clients want us to be.”
So one of my pieces of advice is: build a business, understand your core value, embrace technology but don’t use it to replace human connection. There are two fundamental ways technology is applied. One is under the euphemism of efficiency—how many human beings can it remove from the process for higher margins. The other is the utilization of technology to enhance the human. And I think society is going through this right now.
The one thing around AI that is unprecedented is the speed at which it may operate. If it does it at a speed that is so fast, how do we adjust societally? And now, all of a sudden, liberal arts and being interesting and telling a good story—that’s all becoming important again.
What does the responsibility of leadership look like in the travel space—how do leaders enable people to experience the world more meaningfully?
There are two things. One is the way we at Virtuoso look at it. The other is, I’m the Vice Chair of an organization called the World Travel and Tourism Council, which was originally started over 30 years ago by Bill Marriott and James Robinson III of Amex—basically around creating the private sector voice of the travel and tourism industry. One of the major focuses of that organization is responsible growth.
I do think it all starts with destinations, and all of us understanding what we want and what we don’t want. A community needs to understand what they want, what they don’t want, and go from there.
When we think of global stewardship and what we call purposeful travel, we look at it under three pillars: protecting the planet, preservation of natural and cultural heritage, and benefiting the local economy. The percentage of people who walk in and say “give me a sustainable trip” is a very small percentage—but it doesn’t mean that people don’t care.
A lot of times the people that are the best at doing it are the most hesitant to talk about it, because they don’t want to be seen as bragging. So our philosophy is: start where you are. I’d rather see 90% take two steps forward than 10% trying to reach a perfection that keeps getting redefined.
What we’re starting to hear from clients is that if you can make it easy on me to feel good about who I gave my money to, that adds intrinsic value. So part of what we’re trying to do is help our partners around the world that are doing amazing things tell better stories. For example, if you go to the Brando in Tahiti—Marlon Brando’s private island—you come to find out that they are pioneers in salt water air conditioning, where they have a pipe that pulls up ice cold deep sea water, and they’re doing mosquito eradication. These back stories really add a lot of beauty to the value that you get as a human being. And quite frankly, you come back and some of these stories are the most fun you’re having sitting around a dinner table—what are you going to say, “Well, I ate more caviar than you did”? It’s pretty cool to be able to tell stories that have some sort of fun meaning and purpose to them.
Worth’s motto is “worth beyond wealth.” How does that resonate with you?
I love that, because it goes back to this whole thing about travel being the only thing that makes you richer. It’s worth beyond wealth.
We at Virtuoso actually own the trademark on the phrase “return on life.” What I’ve always said is: why would you have a skilled trusted advisor to help you have a conscious strategic plan to optimize your financial assets—but why wouldn’t you have a trusted advisor, a collaborator, that could help you have a conscious strategic plan to optimize your most valuable non-renewable asset? Your free leisure time. Because if you lose money, you can make it back. The time—it’s gone.
There’s a big misnomer, which is that the people who go to travel advisors are the ones that don’t know any better—they don’t know how to research, they have no contacts. I could tell you right now, the best clients are the ones that are actually the most sophisticated. They’ve realized that having a really great professional collaborator—and I say this when I’m speaking to the owners of hotels and PE groups—the success of our profession is really simple. Who are the people in life that have determined it’s a lot better to have trusted advisors in every important part of their life? People of means. It’s not complicated.
What’s really cool is today’s modern advisor relationship is not “you come to me because you don’t know anything.” You come to me because I have knowledge, contacts, and people. And when we collaborate, combining your assets with mine—and a community of other like-minded travelers and community knowledge—now it’s like you have a palette of colors to paint from that are infinitely better than they ever were on your own.
Many of Worth’s readers are investors, founders, and family office leaders. If you were to ask them to rethink something about travel, what would it be?
The number one thing when I think about founders, investors, family offices: why aren’t you treating this most valuable, non-renewable asset like the valuable asset that it is? Why not have a much more conscious plan?
I think it was General Eisenhower who said: the value of the plan is in the planning. So the whole idea is—having a conscious plan around the ability to enhance your life experiences, your time for yourself, your time with your family, your time with friends—why aren’t we putting more effort into that? And what is the outcome? It’s just a life better lived.
