Lindsey Epperly: Founder & CEO of Jetset World Travel

Episode 517

In this episode, Lindsey Epperly, Founder and CEO of Jetset World Travel, a boutique travel agency renowned for its personalized and luxurious travel experiences. We hear how Lindsey has carved a niche in the travel industry by emphasizing unique, immersive experiences that transcend the ordinary. Shares her journey in the travel industry and the challenges she faced in scaling her business. She discusses the acquisition of Jet Set World Travel and the rebranding process. Lindsay also highlights the importance of building awareness and loyalty in the travel industry, as well as the future of luxury travel. She shares her favorite destinations and offers advice for entrepreneurs.
So much inspiration and wisdom in this episode. Now on this episode of #TheKaraGoldinShow.

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Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be I want to be, you just want to make sure you will get knocked down. But just make sure you don’t get knocked down knocked out. So your only choice should be go focus on what you can control control control. Hi, everyone and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs, and really some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hi, everyone. And welcome back to the Kara Goldin show. I’m so excited to have our next guest. Here we have Lindsey Epperly, who is the founder and CEO of Jet Set World Travel. And if you are not familiar with jetset world travel, you absolutely need to be listening to this podcast because you are not only going to learn about an incredible business, but also an incredible founder and CEO who has not only taken on an incredible feat in this industry, but also really has grown this business to be unbelievable. I mean, it’s it’s really, really incredible. I loved what I was doing research on her company, I’d love just hearing about everything that she’s accomplished and sort of where she came from, and all the peaks and valleys that we talked about. On the show, I really felt like Lindsey definitely has seen all of that and can give us all a great glimpse, but also inspiration into how to maybe do it for herself. But it’s a boutique travel agency, really renowned for its personalized and luxurious travel experiences. Lindsay has carved a niche in the travel industry, obviously a very competitive industry. So I can’t wait to dive into that a lot more. But jetset world travel really stands out for its commitment to excellence. And again, as Lindsay has scaled and competed in this, in this industry, I think is such an amazing story that is very, very motivating. So without further ado, let’s get started. Welcome, Lindsey.

Lindsey Epperly 2:28
Thank you for having me, Kara. I know this is gonna be such a good conversation. Yeah,

Kara Goldin 2:32
very, very excited to have you on the show for sure. So can you give us a little bit of background on you? Who was Lindsay as a kid? Did you always love to travel? Did you always think like when I grow up? This is what I’m going to be doing? Or did you just sort of fall into this place?

Lindsey Epperly 2:53
Gosh, a little bit of all right, I always say that the travel industry finds you versus you finding it. But for me, I think there were two really big contributing factors to how I wound up here in terms of my childhood. One is that my dad is an entrepreneur. And so I always call it my dinnertime MBA, that was how I learned business. Right? He would bring home the conversations of ethics and of growth and of what he was doing next in his business. And we would have conversations as a family about it. So from a very young age, I knew being an entrepreneur is part of my DNA, right? I’m five, two, I’m brunette. I’m an entrepreneur, like I just felt it in my soul. And then the second contributing factor is that part of his entrepreneurship journey included a very short stint in the travel industry himself. So he opened up a cruise holidays franchise, because he couldn’t get anyone to call him back about a cruise he was going on with the family. And so he opened this franchise you probably had it for now he’s like six to eight years old. But I grew up cruising because of that. And so that was my way of travel. And I just thought it was normal for people to one only cruise I didn’t know you could fly and stay somewhere but to to use a travel agent because that was a business humans owned. So those two things I think kind of primed me for at the age of 19. I wandered into a travel agency for a brochure for a trip we were going on and I accidentally walked out with a job. But I feel like I was so prepped from from those earlier years that this could even be a viable career option for me.

Kara Goldin 4:17
That’s why so you started at 19. And just yesterday, doing walking into an agency and obviously the industry changed significantly since that time when you used to walk into an agency I was telling my kids that the other day because I I used to go into travel agencies to to book all flights. I mean, you had two options like you would either reach out to the airlines directly or the hotels directly or you would go inside a travel agency and go talk to somebody right so different than what exists today but three that all of those shifts and changes, you lift it, right, you saw it all, you saw these, you know, all the expedience, and the consolidation of all of these ideas all coming together and competing against each other in many ways. So what did you feel was, you know, really missing? Once you saw all of that? I mean, maybe there’s a step in between the ninth 19 year old Lindsey, working inside of a travel agency and the Jets at world travel. So what happened in between there?

Lindsey Epperly 5:37
Yeah, that’s a great question, Kara. Because you’re right, this industry has evolved in such a cool way. And I feel like I was at the right place at the right age at the right time to be able to study it and see what it needed next. So when I first got into it, I was certainly the only 19 year old in the room, I was probably the only individual that you know, in about 20 years had decided this was a career path worth pursuing. So there was a really interesting gap from when the internet came about. And people stopped believing that it was a viable career path. So from when I was 19, there weren’t 20 year olds or 30 year olds, or barely even 40 year olds at the time who were pursuing it. So I saw this big gap. And to your point, there were mostly brick and mortar stores. Still, at that time, this was about 15 years ago, what was happening was this whole rebrand of even the term travel agent. So it got a good publicity spend. Because when you think of a travel agent, you think of going into a brick and mortar, and they type up a ticket. And here’s a transaction. And what I saw happening, and what I really latched on to is there was an opportunity for forming a relationship. And so now it’s gone from travel agent to Travel Advisor. And so as I’m studying the industry at 19, and saying, What could this use, I could see a world in which that travel advisor role was modernized, you know, we could meet clients where they are, which is all virtual. So when I decided to launch a company, it was then called Epperly travel. And we can certainly get into how we became jet said it was via an acquisition. But when I launched that really travel, it was completely virtual it was let’s serve a foreign five star client base across the globe with advisors located all around the world. They won’t know if we’re in Spain, doing a trip to tour hotels, or if we’re in their own backyard, it’s all going to be done virtually, and from a human to human perspective instead of a transaction perspective.

Kara Goldin 7:24
And so you just mentioned you was through an acquisition. Can you talk a little bit about that?

Lindsey Epperly 7:30
Yeah, yeah, I’m happy to that was kind of one of our prouder moments, because I 10 years ago, actually will be 10, this year launched Epperly travel my maiden name. And about five years ago, my husband, who was my fiancee at the time, decided to join me in business and in scaling. So I want you to imagine he’s been doing this alongside me, we’re not business partners, yet, I have no desire to have a partner. You know, this is my baby. But we’re just a couple years into that whole business working relationship. And I’m pregnant with our first child, we have a home under contract, and it’s March of 2020. So that obviously levels so many industries, but the travel industry in particular, like we can’t plan trips when the planes are grounded for months and months. So we have all eggs in one basket, and we decide we’ve got a hold steady with this mission that we believe that this agency can achieve, right? Like we went into the pandemic with I think 10 team members, and we were able to use the funds that we would have used toward that home, we decided to walk away from it to save the business toward an acquisition opportunity in 2021. So in 21, we were able to say, All right, if we could do anything in the world right now, what would it be? And for us, it was well, could we acquire another company? So we had long since admired this company, jetset world travel, incredible female founder, Julia Peron, who I had long since looked up to the agency was older than ours. It was bigger than ours. But it was an opportunity where she had never quite had the operation side like we were getting down right at Epperly travel. So we started talking and that acquisition opportunity presented itself and it is the move that catapulted us as Epperly travel, we eventually rebranded as jetset because we wanted a platform that was more serving to the team. But it also sent this really cool message to our industry, where it was all about consolidation and mega agencies gobbling up smaller ones. And all these mom and pops are going it was a message of female founded entrepreneurship, and it is strong and alive and well. And that’s something we really are proud up to this day.

Kara Goldin 9:31
When you merged the companies together, was it? Did you change kind of the ethos and mission of what you had been focusing on? I mean, was there one for just for example, you were talking about cruises, were you more focused on you know, different types of trips and then now you are going to be more focused on this consumer who maybe wanted different opportunities, what exists equity. How did you think about it? Yeah,

Lindsey Epperly 10:02
that’s a good question. Because we were very fortunate that jetset had an extremely similar ethos to us, they were already running virtually, they had a very similar client base. We do cruises, tours, hotels worldwide, both companies did. And when we acquired them, we actually ran both brand side by side for about a year because we really wanted to kind of study to make sure that this is our first acquisition, right like, and at this point, I’m also making the active choice to become business partners with my husband. So we’re now navigating this acquisition for the first time this company’s larger than we ever dreamed it would be. Let’s make sure we don’t rock the boat. Let’s study both companies see how they’re doing. They both had great reputations in the industry. But why we ultimately decided to make that decision on on rebranding, the way we looked at that was, the agency has two arms to it, right. So one arm is essentially the direct to consumer, where the end client is the traveler or the other arm is we we power other travel agents and travel agency. So we essentially said as a back office, like an umbrella company, something like you’d see an insurance or real estate. And that particular arm is very fast growing in the travel industry. And so if we are going to lean into what is a host model is that the reference, if we’re going to lean into that, we want to create a brand that can uplift all of the other advisors, instead of it being the Lindsay app really show. So the messaging we created around that was let’s go for Me to We and let’s become jetset world travel. And that was the decision behind that.

Kara Goldin 11:29
So what was kind of the the most significant challenge in doing that? I mean, this was kind of new to you. Right? You know, you weren’t just talking to consumers. Now you’re, you’re, I guess it’s b2c and b2b. Right. And so that’s, that’s a big shift, and your company, right, and sort of what you had been running? I mean, first of all, how scary was that? And also, what challenges did you have to face in order to really be able to take that on?

Lindsey Epperly 12:03
Yeah, that’s such a good question. And I’m glad that you haven’t touched on the scary side of it, right? Because I think it’s, it’s something we should admit as entrepreneurs is when we’re in those positions that make us a little bit scared, those are usually the right direction to go. But we have to overcome that fear. I talk a lot on my own podcast about impostor syndrome, you and I talked recently, when I interviewed you, and man did that imposter syndrome rear its ugly head during a season of acquiring another company bringing two companies together, I also had a health crisis in the middle of all of that. So just things that were challenging me as a leader, I never hesitated when it came to the business model. And I think a lot of that is because I had sat in the seat that the advisors were in, right, I had once been the lead advisor. And for anyone listening, that is going from being a solo practitioner, or the main person in the business, it’s, it’s their baby. And now they are scaling that there’s a whole slew of challenges that comes with that, right, like the idea of letting go of control. And I was such a bottleneck for so long, because I was trying to sit as an advisor and as the CEO trying to scale but also trying to serve clients. And there’s, there’s just no ability to do all of it at once. So the decision to really step out of the client facing role and step into a position of leadership, which was much more intimidating to me, you know, I’d never ran a company that size. And every day, if it’s doing right, it’s gonna grow a little bit, which means every day, it’s a little bit larger. And that’s a little bit scarier as a leader. So really having to confront that impostor syndrome, and study up and make sure I’m in my best position of authenticity. And empathy as a leader has been probably the greatest challenge, but also the greatest reward.

Kara Goldin 13:44
Yeah, definitely. So the travel industry is, I mean, I can only imagine how difficult it is because you’re probably dealing with, you know, pricing issues that go on, like, how do you? What is the hardest thing about the travel industry that maybe the average consumer doesn’t think about? I don’t know, the travel industry, other than the fact that I love to travel? I mean, what is it from a operator standpoint, is very difficult for you.

Lindsey Epperly 14:21
You know, it’s interesting that you touch on the pricing thing, because I wouldn’t even say that’s the biggest issue. I mean, it definitely is of interest in just for general consumer, you know, when you work with a Travel Advisor, a really good Travel Advisor who’s worth their salt is probably going to charge a small service fee that covers their time. And then the pricing should be pretty consistent with what you would find direct. It’s not going to be the same price as Expedia because that’s an online discounter and they’ve got a totally different model, which is okay until it goes wrong, right until you have booked one of those trips and now you’re Sol because you paid the rock bottom prices and the hotel no longer cares, whereas the Travel Advisor pricing should be about the same across the board through the direct hotels or cruise lines, the bigger issue as an operator, I think is that we’re representing so much that is out of our control. And so whether it’s a strike in France or a hurricane in the Caribbean, or a world pandemic, right, like, there are so many elements that once we have planned this beautiful trip for our clients, they’ve come to us and they trust us with planning their memories, and for getting it right. There’s so much that’s out of our hands for being able to actually puppeteer and get right. And so we really have to think on our toes. And he always tried to teach my team to come in with the idea of empathy and authority, right, like any situation that we have, I really believe we can solve if we put on our empathy hat and see human to human, I too, would be upset if there was a hurricane actively affecting my destination. But from an authority perspective, as a Travel Advisor, I live eat breathe this every day. Here’s my expert opinion on what our options are, right? So we can solve it. But from an operation standpoint, you just don’t know what you’re going to wake up to every day.

Kara Goldin 16:01
Yeah, no, I can only imagine. And people are probably for these types of trips. What is the average number of people that you’re actually booking for? As well, in a party? Like are you booking? Do you find that it’s? Is it rarely one individual? It’s usually like a group, right? I mean, either a family or is it a or a company? Or? I mean, I would think like, it’s not just one person having a problem. It’s probably multiple people having problems from all different, right? I mean, is that yeah, is that accurate?

Lindsey Epperly 16:38
It depends on the type of travel agency that you’re talking to. Because what we’re getting into now is we are a leisure travel company, which means we specialize primarily in vacations. So yeah, it’s anywhere from a you can have solo travelers, that’s definitely part of our subset. But typically families or small groups, you know, multiple couples traveling together, or a family of four, whatever that looks like. We do have some small corporate groups that we work with, but small being like maybe 100 people, Max. So for us if there is an issue that’s impacting, yes, it’s several seats on a plane and several hotel rooms, whatever that looks like. But that just depends on the type of travel agency that it is.

Kara Goldin 17:17
Yeah, no, that’s so interesting. So what strategies have you deployed to really build awareness for what you’re doing? And obviously, you know, again, going back to you are a b2c and b2b play. So what percent of your business I should ask that first, like is b2b versus b2c?

Lindsey Epperly 17:40
Yeah, I would say probably about 30 to 40% is the b2c and then the majority is the b2b element. But I think that there is a an aspect of this, that’s the through line when it comes to what jetset does really well, which is meeting people where they are. And so if it’s the b2c element, what that looks like, is a very intimate relationship with the clients where we’re really understanding, Hey, what is that dream in the back of your head? And how do we turn it into reality? Also, if there are other travelers on that trip, it’s like 90% therapy, right? Like, my husband wants something different than I do. And my kids want something different, too. So they’re, they’re really trying to meet the clients where they are. And then they’re finding really cool touches to surprise and delight. So if it is an anniversary trip, we’re finding out what song was played on their wedding night that they dance to, and let’s make sure that the band dedicates that at one of their dinners, right? So little special touches from the b2b element, we look at it as a lot of business consulting. So we look at the status, how do we meet our advisors? Where they are based off of? Are they new to industry? Or do they have an existing book of business they want to grow? Yes,

Kara Goldin 18:44
so interesting. So what strategies have you deployed to build a strong and loyal community? Do you find that most of your consumers, new consumers are hearing about you through word of mouth or social or where is the biggest kind of lift for you coming from?

Lindsey Epperly 19:07
So for us, I really feel like because what we do as a customized product and service, word of mouth has been by far the number one way we build rabid fans. And we extend the reach of, of how we’re marketing essentially, right. So when we do something like that surprise and delight, where we have a band dedicated song to the clients that are celebrating their anniversary like that, you know, that’s like a hand to hurt moment. That’s what we call it at the company. And we celebrate those handle hurt moments, both internally, with the team members and with their clients. So when they come back, and they say, Oh, I had a client that walked into the room and saw a photo of their dog that they left behind, right, like that’s going to hurt moment. The clients are going to share those. It’s so exceptional. It’s so personal and so special. And you’re not going to get that with Expedia who doesn’t have a clue who you are. Yeah. So it’s really again, meeting the customers where they are that has allowed for just incredible growth. That’s awesome.

Kara Goldin 20:07
So where do you see the future of luxury travel heading. So

Lindsey Epperly 20:11
I get to continued diving in deep to that customization, which actually makes our job a lot harder, right, like in terms of holding the tension as a CEO of a company that wants to thoughtfully grow and scale, but also wants to serve our customers? Well, in both b2b and b2c, it’s continuing to find ways where we can use technology, we can automate, we can even leverage AI so that we’re more efficient, so that we can actually deliver on that promise of a better customer experience. No,

Kara Goldin 20:42
I love that. So what is kind of the hottest places for people? Where do people want to go? I mean, I feel like are there? Are there trends that are happening right now? I would guess, based on seasonality, you have, you know, certain times a year that people want to go to certain places. But do you feel like there’s something that has come up recently that that really is kind of, you know, hitting the excitement for everyone involved, that everybody wants to go to one or two places.

Lindsey Epperly 21:17
You know, it’s so fascinating to me. And this is what you need a Travel Advisor to be able to navigate this kind of post pandemic landscape. Yes, there are certain places that have seasons due to weather, etc. But there used to be a lot more opportunities to travel during offseason and shoulder season. And what we’re seeing post pandemic is that demand for travel is so high, that if it’s a popular place, it’s probably popular year round, like there’s no longer the same element of seasons to be able to save a little or you should go here then because it’s a hidden secret. Now it’s all about some of the emerging destinations. So while we’ve got places that are so popular, right, Italy will always be someone’s number one, I mean, like, not necessarily everyone, but in terms of like a mass market response, constantly sending people to Italy. But if someone’s looking for the next undiscovered Italy, they need to know about Slovenia, or if they’re outdoorsy, and they’re about to spend 30 $40,000 on a Europe trip that they never thought they would spend. Maybe we’re considering spending that money in South Africa, because it’s going to go further. And it’s going to scratch that itch of being outdoors. Right? So so it’s always kind of looking at what that individual is dreaming of, and what resources they have to work with. And then applying that accordingly. Given the ever evolving landscape of the travel industry.

Kara Goldin 22:28
Yeah, no, definitely. Is there a place that people are or, or a type of travel that people tend to be shying away from right now?

Lindsey Epperly 22:37
You know, I wouldn’t necessarily say that anyone is shying away. I mean, we definitely saw for a little while people were you know, obviously with the pandemic situation a little hesitant on group trips, or even cruises, for that matter. But that is that is really in the past. I mean, travel right now is at an all time high. So I think if it’s an opportunity for someone to take it, they’re taking it.

Kara Goldin 22:59
Yeah, no, I love it are people taking longer trips,

Lindsey Epperly 23:03
we hoped that we would see that in a post pandemic world, we actually hoped that we would see a little bit of a slower travel pace, right? Because Americans are so aggressive when we go travel, we want to see it all and do it all at once. And we really oftentimes feel like ah, but if you were to just spend an extra day in that destination and immerse yourself a little bit more, you might get more out of the culture, right, you might get to experience it. I think that people’s memories are pretty short lived. And so we’ve seen that kind of return to normal, normal being, you know, the amount of time they have, then again, a lot more people are able to work remotely. And so we have seen that in certain family settings that they’re saying, Okay, actually, my company’s gifting me a sabbatical. Or I know that I can do what’s called leisure, right, a business and leisure trip, but I’m blending together. So we do see that emerging more and more.

Kara Goldin 23:50
So I always ask people about their company and like a favorite SKU or a favorite product, or is there a favorite destination that you have that you personally have been like? Oh, my gosh, I like love it there. I’ve been there so many times, or I’ve only been there once, but it’s amazing.

Lindsey Epperly 24:08
Yes. Oh, my goodness. Okay. So I get asked this question a lot on podcasts that I do interviews on. And I always give the same answer, which is South Africa. And I just mentioned South Africa to you. So I’m going to give you a little bit of a different answer, in that I want to drop South Africa because it’s my favorite. But the place that surprised me the most personally was Ireland. Have you been?

Kara Goldin 24:28
Yeah, it’s a great place. Yeah.

Lindsey Epperly 24:32
I think that I expected it to be very sleepy, and that it was the type of place someone would go after they’ve been everywhere else. And for me, I found that the beauty of being able to rent a car or being able to connect with locals, I actually enjoyed the sleepiness of it right. It allowed me to slow down a little bit driving out and kind of this wild Atlantic coast and I’m a moody traveler so I you know, some people like the beach I like like a good cliff side with some fog rolling in for me is the perfect spot.

Kara Goldin 25:01
So we have a lot of listeners who are entrepreneurs, and also CEOs like you are, that maybe are just entering into being an entrepreneur, or maybe they’re just thinking about, I’m gonna go start something, I’m hearing all of these incredible, very inspiring stories of going and starting a company, but what advice would you give to entrepreneurs that, you know, remembering the day when you’re thinking, I’m gonna go do this, this is really scary. But I’m going to figure out a way to go and start my own thing. What advice would you give to entrepreneurs? Yeah,

Lindsey Epperly 25:41
you know, I was actually writing about this recently, on my blog, when it came to something that I fell into a trap early on, where I had a lot of great mentors, but the mentors thought very differently than me, right, especially as a female. So I had a lot of great male mentors, who, when I would encounter a business problem, they would always say, you just kind of get thicker skin, right, like, don’t let the emotions like get thicker skin. And so for so long, I lived in that, that idea that I could kind of put myself in the way of a problem and that I would grow thicker skin. And then I found over time that I was actually like weakening and burning out. And what I found as an entrepreneur, is that when I actually listened to my intuition, which was trying to speak up in those moments where I thought I needed thicker skin, I would I would pay heed to it saying, actually, this is a moment where you need to evolve, and you need to employ someone in that position instead of you continuing to step into it. That was when my business really took off. So I kind of look at it as instead of just trying to muscle your way through grit is a great thing. Of course, we have to have grit, but instead of trying to muscle your way through, it’s actually listening to your intuition about what’s the next right thing.

Kara Goldin 26:48
So great. So Lindsey Epperly, founder and CEO of Jet Set World Travel. Thank you so much for sharing your wisdom, not only about your company, but also about your journey and the industry overall. So appreciate it.

Lindsey Epperly 27:03
Thank you, Kara had such a good time talking to you about it.

Kara Goldin 27:06
Thanks again for listening to the Kara Goldin show. If you would, please give us a review and feel free to share this podcast with others who would benefit and of course, feel free to subscribe so you don’t miss a single episode of our podcast. Just a reminder that I can be found on all platforms at Kara Goldin. I would love to hear from you too, so feel free to DM me. And if you want to hear more about my journey, I hope you will have a listen or pick up a copy of my Wall Street Journal, best selling book undaunted, where I share more about my journey including founding and building hint. We are here every Monday, Wednesday and Friday. Thanks for listening and goodbye for now.