How Much Can I Make? - Discover Your Dream Job.
"How Much Can I Make?" - Explores career opportunities and job advice.
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This podcast dives deep into what different careers are really like—what the day-to-day looks like, how much you can earn, and what it takes to succeed. You'll hear firsthand job advice from professionals who've been there, done that, and are eager to share their stories.
If you're curious about your next move, or just exploring career possibilities, you're in the right place!
Nominated for 2025 Women Podcasters award.
How Much Can I Make? - Discover Your Dream Job.
Building a Career as a Travel Designer: Tips from Kelli Carpenter
Travel Designer
6/24/25
In this episode, explore career opportunities with Travel Designer Kelli Carpenter - of KelliGregg Travel - who shares valuable job tips and insights on overcoming industry challenges.
Kelli transformed her passion for travel into a thriving career. She reveals great job tips for aspiring travel entrepreneurs, discusses how she built a niche serving LGBTQ families, and shares strategies for overcoming challenges, including the pandemic's impact on the travel industry. Tune in to discover valuable insights on networking and making money in the travel sector, and learn how meaningful human connections can enhance your own travel experiences.
Topics
0:17 Introduction
1:37 The Role of a Travel Designer
2:49 From Marketing to Traveling
3:37 Identifying a Niche
4:48 Pivoting to Changing Market
6:23 Building Our Family Vacations Brand
8:18 Safe Destinations for LGBTQ
10:05 Grow the Business
11:07 Creating Memorable Group Experiences
12:56 How Covid Changed the Business
16:19 Skills Needed to Run Such Business
17:59 The Money Structure
20:35 Post-Pandemic Travel Challenges
21:36 Business Challenges and Personal Rewards
24:23 Is AI a Challenge?
Resources
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Music credit: Kate Pierson & Monica Nation
Vacations change people's lives. They save up all year. I mean it's an expensive investment, but it opens their eyes to the world. You get to open their children's eyes to the world and people are passionate about it.
Speaker 1:Hi, welcome back to how Much Can I Make. I'm your host, merav Ozeri, and today we're diving into the world of travel with an entrepreneur who saw a need in the industry and ran with it, or should I say, actually sailed with it. My guest is Kelly Carpenter, co-founder of the groundbreaking company Our Family Vacations, which made history as the first travel company to design full-scale vacations specifically for LGBTQ families and their friends. Now rebranded as Kelly Gregg Travel, her company continues to lead the way, offering everything from luxury river cruises to curated group adventures around the world. So let's dive right in and hear how she built it from the ground up. Kelly, thank you so much for joining us. I'm really excited to have someone from the travel industry.
Speaker 2:I can't believe I'm your first travel industry person.
Speaker 1:You are, are there still a lot of travel agents?
Speaker 2:Well, it actually went from one direction to the other. So all these online ability to book your own travel happened. People were like we don't need travel advisors anymore, we can just do it ourselves. Well then, all of a sudden, more companies launched that were doing this online travel. It got more confusing. People realized that they don't have anybody actually taking care of them, so they don't have anybody. That if they need to cancel, they can help get that refund back, they can advise them on where to go. You know, an actual person is more helpful than a bot on a website and I also think a lot of people don't realize and people do it differently but it doesn't cost you anything extra to use a travel advisor. We get paid by the cruise line or the hotel or the tour operator.
Speaker 1:You call yourself travel advisor and not travel agent. Please define for us the difference.
Speaker 2:I actually refer to myself as a travel designer.
Speaker 1:Designer right.
Speaker 2:Yeah, I work on a lot of different projects that not only are the group's business, the charter's business and the individual business, but it may involve air, a cruise, a tour, it may involve so many different things and you design a vacation for somebody. An agent in my head is somebody that basically just inputs into Sabre or an airline site and books your flight and books your hotel. You know what I mean. Like it's not coming up, it's not a creative position in my head and to me, an advisor advises their clients and a designer creates magical vacations advises their clients and a designer creates magical vacations.
Speaker 1:So let's back up for a second. You worked in marketing for large companies like Pepsi and Nickelodeon, and how did you make a switch from that to travel?
Speaker 2:When I graduated from college, my main work was always in the marketing world and my last marketing job was at Nickelodeon and at the time I had young children and I realized that I wanted to have more time with them and less divert my time, especially at that age. So I left my Nickelodeon job and I still freelance for them, which gave me a lot of control of my time but still kept my brain, you know, working and kept those contacts going. And I always loved to travel. My family went on a cruise every year from the time that I can remember.
Speaker 2:So I was always you know, and my parents were avid travelers, so it was always part of my world and I decided, while freelancing for Nickelodeon, I saw a niche. I saw something missing in the travel world. There was an all lesbian company travel company, an all gay male travel company, but at the time and this was 23 years ago, 24 years ago there was nobody that did this for LGBTQ families, and that was the beginning of the launch of the company. Is that? I felt like if I was searching for that world, there must have been so many other families, gay families that were searching for that world. I had gone to Provincetown, I had gone to family week in Provincetown and seen what my kids saw like, look, mommy, you know other families that look like ours and I was like, oh my gosh, there's definitely a place for this.
Speaker 2:But my, I had never worked in the travel industry and at the time I became friends with my now business partner, a guy that's like my brother at this point in time, and he had worked for Atlantis Events for years. He was their producer and so he understood how that business works. So with us we launched this business and it was a very long time ago and it has taken many twists and turns along the way, just with our community changing what our needs are changing. I now, you know, do eight, nine trips a year.
Speaker 2:Wow and only one of them is a family trip Only how many is a family trip.
Speaker 2:Only one is a family trip now. The rest are adults. Only because I ended up with all these empty nesters. That kids grew up on my trips and then, boom, they all still want to travel. So you know, I've diversified quite a bit and it's about, I feel like in this industry because it's constantly changing and your clientele is constantly changing, that you have to be flexible and sort of have your fingers on the pulse of what are people wanting right now. How do people feel like they want to travel safely? What can I do to help that happen? We had to do a big branding change. The name of my company was Our Family Vacations and what I found as my clientele was growing up and I wanted to do these adult-only trips, is I'd do advertising. They'd be like well, we can't do your trips, we don't have any kids, and it was still called our family vacations. I was like family's, what you make of it? The branding changes we did it over the pandemic because we had very little to do.
Speaker 1:Oh, I have questions about the pandemic Right.
Speaker 2:And we did a branding change and it was probably the smartest thing we ever did.
Speaker 1:So walk me through the process. You decide to do a cruise trip to a destination. How do you take it from there? Do you create whatever you like, wherever you would like to go? Or how does it work?
Speaker 2:It works in a variety of ways. So with our family trips it's an interesting business model because there's only two weeks out of the summer that all kids in the United States are off of school. It's different on every part of the United States, so we have to cram that trip into those two weeks in July, pick one week, and then you also are creating a product during the most expensive time that everybody is traveling. So it's an interesting business model and it's where I'm happy. My business has grown to be just beyond that. But that is usually either a family resort or a cruise ship with kid programs, because that's something that comes into account. You have to be able to take care of from babies to teenagers, from parents to grandparents, from people without kids to people that have one kid or four kids, or you just have to go through. What we used to do is go through the schedule and say, okay, if I'm a mother with a three-year-old, what does every day look like? If I'm a grandmother that's here with my family, what does every day look for her? And you have to program for every single person on that trip. So that one trip a year is pretty formulaic after this amount of time.
Speaker 2:But as far as picking other trips, we listen to our clients about where they want to go and I also pick places that I feel like is of interest to me, that I've never been, and I'm sort of like come join me, let's go see the world together, and it usually ends up working out. I mean, I had always wanted to go to Egypt but I was nervous to go with just myself and my wife and Uniworld, one of the best travel partners I have. They have a river cruise company and I work a lot with them and they have a river cruise that goes down the Nile. I contacted them. I was like I want to bring a group of 10 cabins. Let's just say we sold out the entire ship because there were so many LGBTQ people that were nervous to do the same thing I was nervous to do, and I have found that that has been a great strategy. It really has.
Speaker 1:Is every destination safe for LGBT tourists? Are there places that you would not go?
Speaker 2:There are certainly places I would absolutely not go. However, there are places that you would not go. There are certainly places I would absolutely not go. However, there are places that I wanted to go that you have to be respectful of what their laws are. I'll take Egypt, for example. It's, you know, not known as the most LGBTQ friendly place. If you're respectful about the laws public displays of affection I tell my gay male clients I don't think you should go on Grindr. I think you know there's things that you have to be respectful about and you have to follow their laws.
Speaker 2:We did a trip in the cruise left out of Morocco, out of Casablanca, and you know it's interesting because we were staying at the Four Seasons pre-trip and they really did not want to put the same sex couples into one bed.
Speaker 2:Like every time I would check in, they were like we're going to give you two beds and I was like I don't want two beds. But I think you just it is what it is and you talk to your clients in advance and you know we also go to many, many LGBTQ friendly country, like I do a host of tour every two years through Thailand, one of the most LGBTQ friendly countries that you could go to, and it is an absolutely magical experience, and I feel like you just have to understand where you're going and inform your clients, and I think that I just got back from South Africa a few weeks ago and I didn't run into any issues. However, I've had other people that have. So I just think you just have to be aware, do your research, and that's what your travel advisor helps you do, and that would be one reason that you would want a travel advisor.
Speaker 1:How did you get your first client?
Speaker 2:My business started off as one cruise ship charter a year. I was what would be considered a tour operator. So basically you buy that ship, you repackage it with all of your programming. It already has the infrastructure which makes it great, but you bring your own entertainment and parties and all of that, package it and resell it. So I ended up with a lot of clients.
Speaker 2:Well, actually it wasn't even my idea. So we were doing this business and we had a travel agency come to us and they were like, have you ever considered just becoming a regular travel advisor? And I was like no, I hadn't really thought about it. They're like you realize, your clients that are taking that one trip a year with you, all of them go on more than one trip a year. If they could book with you, the amount of additional revenue that you could get from not only them, but then they recommend you to their family members, and so it just goes on and on and on. So the first clients came from people that already traveled with me, and now they come from a lot of referrals and, like I said, I do river cruise charters. So those house about 200 clients each on them and so they also book additional trips and they tell their family and friends. So I would say, mostly a word of mouth business, you do a great job and vacations change people's lives.
Speaker 2:I mean you have to imagine they save up all year. I mean it's an expensive investment, but it opens their eyes to the world. You get to open their children's eyes to the world and people are passionate about it, so they're going to go sell your story to somebody else. So I think that that's really important.
Speaker 1:So 200 people is quite a large ship.
Speaker 2:Our beginning cruises. When we first started, we were chartering 4,000 person ships.
Speaker 1:Wow, and you filled it up.
Speaker 2:Yep, we filled it up and now we don't do that level of business on the large cruise ships. They've just gotten too big. I mean, these ships now are enormous and so we do large groups. I have a large group, my family group, on NCL, norwegian Cruise Lines, in July and I've got a little over 200 people. I've got a group on a mega yacht leaving out of Stockholm to Copenhagen on end of July. I've got 40 people on that. So it depends on the ship and it depends on the product.
Speaker 1:So you have to get the ship, get all the hotels in the different places, right?
Speaker 2:Yes.
Speaker 1:There's a lot of liability involved also, correct.
Speaker 2:Basically what we do as a company. Because we don't charter large cruise ships anymore, the contract is directly with the cruise line who has?
Speaker 2:all the liabilities managed. I always say to somebody they're like they skipped a port, I'm going to sue. I was like, honey, you signed your life away when you signed that cruise ship document. You're not suing anybody, that's what travel insurance is for. But yeah, so it takes away a lot of our liability. We're a two-person company doing, you know, all those bookings, so we work a lot with the cruise line and it does help to have their support.
Speaker 1:Yeah, you have to have the support. How did the business change since COVID? Do people demand different things, more personal safety, etc.
Speaker 2:It was, you know, an awful time for the travel industry. I mean, look, it was an awful time for everybody. But the travel industry specifically took some really solid hits just because we spent the first three or four months just giving people their money back and hoping that we were going to get those clients back when the pandemic was done. So we just were losing money and losing money and losing money. We got some help from the government and I think the main thing that it changed is people realizing that things can change in a hot second and travel, travel protection and travel insurance changed. I never had people want to take it out because they never want to spend the extra money, but since pandemic they always take out travel protection and travel insurance and I would say that's the biggest difference. You know the state of the world right now. I think people get a little bit anxious right now, but people are still traveling and I always offer some great tips to get through an airport, because airports are not easy right now and flying is not easy right now.
Speaker 2:One thing I would tell people that are traveling there's something called the Airline Passenger Bill of Rights out that Pete Buttigieg put together. It was something that the EU had had in place for a long time and we finally have it here in the States, and it literally lays out for you your right as a paying passenger on board an airplane. When they delay you and you sit on the runway too long, they lose your luggage, they cancel your flight, overbook your flight All of this stuff has benefit to you. Of course, you don't want it to happen, but just don't believe everything they tell you. Don't put your arms up in the air and be like, oh, this just stinks and there's nothing I can do. There are things you can do financial compensation, just different things to just always be aware of.
Speaker 1:So your work does it end at the end of the cruise or the end of the trip, or you have to still work with a group after the trip well, my work, I you know, the weirdest thing is, like I don't, in travel you don't really have a day off, sort of it's.
Speaker 2:You have to always, always remember it's also it's not your vacation, it's their vacation. So, um, when I'm even when I'm hosting a trip, I'm already working on the next trip that's coming up. You know, because there is the pulling it together and the sales piece and the production piece, and then you host the trip and then it all starts over again. So, um, I just got back from hosting a group on a celebrity cruise where my, my wife, um, is a touring singer and she's also a main stage singer on a lot of cruise ships and we started this new brand called gig trips. So, when she's also a main stage singer on a lot of cruise ships, and we started this new brand called Gig Trips, so when she's on the main stage, I host a group of guests and we all sail together and they get to see her perform, and so we just got off of that on Sunday and we leave again on Saturday.
Speaker 2:So pulling together all of the details for every single trip with very few days, where you're actually not jet lagged and on the ground, is an interesting, with very few days where you're actually not jet lagged and on the ground is an interesting process. And it's also a process that it's about time management I could be, cause I work with people in all different time zones. I feel like I, from the time I wake up until the time I go to bed, I could be on the phone or my computer or answering emails and you know, sometimes I just take a day, I say Sunday I'm not going to work and I just I don't look at my emails. And you know I do need to take those days probably more often, just because our schedules are weird. You know we both have strange travel schedules.
Speaker 1:So what advice would you give somebody that want to break into that business? What kind of skills do they need? What advice would you give them?
Speaker 2:You need very, very strong executive functioning skills Because you need to be able to manage the time. Every single minute that that guest is on a trip that you book for them needs to be able to be accountable for. So you know, the truth is is like if you're like, oh my gosh, I booked the hotel on the 18th and the tours on the 19th and I messed that up, you know you have to really be able to look at a schedule, manage a schedule and manage times. I would also say that you need to be a person, friendly, forward person, like if you know, I get people that call me and they have wonderful things to say to me, and I get people that are mad and you have to be a great listener. It does do the customer's always right. Philosophy and I'm going to say something sort of interesting is that people always say you know, do you get mad when people complain? And I was like I'm going to say 90% of the time that people are complaining to me, it's a legitimate complaint.
Speaker 2:And it's a lot of money that people are spending and I feel like there's construction at the hotel and they're at a five-star hotel and paid for a five-star hotel. That's a legitimate complaint. And they're at a five-star hotel and paid for a five-star hotel that's a legitimate complaint. So I think to be a really good listener and be a great problem solver, because you also may end up with somebody that is in London and all the flights have been canceled and I need to find them a hotel and I need to figure out what their travel insurance claim is going to be. You need to help them through the process. So you have to be a really good problem solver. Those would be the three things that I would think would be best if you want to jump into the travel industry.
Speaker 1:Is it a lucrative?
Speaker 2:business. These days the travel business industry is interesting because some people do it as a part-time job. You can do it as much as you want to do it. The business is what you decide you're going to take in. So a lot of people do it sort of like real estate. I think a lot of people do it on the side because you can sort of control your hours.
Speaker 2:Now, how I do it is full time. I don't know how long my body can, you know, keep traveling the world and hosting people. But I mean, mine is a full time job, but not everybody's. So I think some people can go work for a travel agency and be more of a phone taker of bookings and things like that. Or you can be more creative with it, like you could be somebody. That's like you know what. I've got 200 people that I think would love to do a. My daughter just graduated from the University of Delaware a University of Delaware reunion cruise. I'm going to start with that project and you book it and you do it and you see, okay, do I like this, do I not like this? It's a great way to sort of dip your toe in. There's self training courses that you could sign up, for there's different ways to do it.
Speaker 1:So but how do you make money? You make a commission from everything, because you said before the, traveling through an agency is not necessarily more expensive an agency is not necessarily more expensive, correct.
Speaker 2:So how it works is you will work for an agency and that agency does whatever split that you agree upon with them. With you, because they're going to manage the money and the bookings.
Speaker 1:Oh, so it is like real estate.
Speaker 2:So let's say it's. I'm just going to say I get 70% and my agency gets 30%.
Speaker 1:Okay.
Speaker 2:So all of my bookings go through them, so my commission, though, goes through them too. So, basically, the cruise line may pay me 15% commission on the thing that I did, they're going to pay the agency that 15%, and then I'm going to get my split of that Okay.
Speaker 1:Wow, it works just like real estate. You're right about that.
Speaker 2:Yeah, it's a very similar yeah.
Speaker 1:What trend do you see for this coming year and going forward in travel?
Speaker 2:Oh, I only had a crystal ball. I'm nervous because I feel like it's just it's the world's a crazy place. Now when I go travel I don't feel it anywhere else. Now I don't know if that's going to change, but you know, people are nervous about the airport experience. People are nervous about are other people in other parts of the world going to hate us because we're disrupting everything right now? There's a lot of questions and I don't have the answers to those questions. All I know is that I'm still traveling and my clients are still traveling and so far, so good, we've all been okay. So I feel like post-pandemic. One thing that I would say changed is people also realize life is short and there's places they want to go see, and I'm finding clients are being a little more exotic with their travels. They're not just wanting to go to Europe, they're wanting to go to different parts of the world and I'm really thrilled about that.
Speaker 1:So you do other travel besides cruise ships.
Speaker 2:I do land tours. Every two years I do a land tour through Thailand, we've done two through Ireland, we are doing another one in Scotland. So we do do land tours also.
Speaker 1:What do you prefer? What do you like best? They're really different, but land tour is a little less work than the cruise, right.
Speaker 2:For the clients. Land tours I find maybe a little harder because you have to unpack and repack every place you go. Cruise is what I love about it is you unpack once and you know you get to see the world. So there's an ease to that that clients really like and for me it makes it a lot easier too.
Speaker 1:What's the biggest challenge of your job?
Speaker 2:My biggest challenge of my job is I have to trust my destination specialists on the ground, like, if I'm booking a trip through Japan for a client, it's not going to be me I mean I work with a local tour operator and they have to deliver for me, or else I look like a client. It's not going to be me that I mean I work with a local tour operator and they have to deliver for me, or else I look like a failure. So it's those relationships that become vital and important, and so some of the anxiety I always have is like what if they're not able to deliver? Or what if they don't deliver and it's three o'clock in the morning and I'm not going to answer my phone. You know what I mean. It's just like it's more that kind of anxiety.
Speaker 2:The other biggest challenge is sort of like you just asked me, the future. You know, as we saw with the pandemic, it's like it can change in a hot second. So you know what I do. It's it's a luxury to be able to travel and and people have to feel confident about the market. They need to feel confident about their financial status.
Speaker 1:What's the biggest reward?
Speaker 2:Oh my gosh, that I get to see the world with people that I respect. I love People that have been traveling with me for 22 years. The other I'll tell you. The other great reward is I sign into Facebook and the amount of people that have made lifelong friendships on the trips that I've hosted and they all go see each other and visit each other, plan their next trip together and sometimes, when I feel frustrated with my work, it's the only thing I find Facebook really good for.
Speaker 1:I sign into Facebook and I'm like look how many friendships have been created because I do what I do and that makes me feel good. Do you have any particular story of a certain trip that comes to mind? That was like amazing. That stays with you forever.
Speaker 2:Well, I mean, you know what story stays with me forever is the very first cruise ship charter I did so long time ago. It was myself and my business partner. We had one assistant. We did every booking on our own and you have to imagine if you're an LGBTQ family. Nobody came traditionally to your family, so every family has a unique story. So we heard every one of those family stories and we had not met any of them in person. So the minute that Greg and I walked on stage to welcome everybody to the cruise and we looked around realizing that we had talked to every single person in that room, heard every single person's story, and I was like this is powerful and I will never forget that moment. And I've had many of those moments since, but that first time of of walking on stage and being like everybody's in here has got a fantastic story to share. So that was, like my, my biggest moment of knowing that we were on to very special.
Speaker 1:Yeah, sounds like it. I was wondering if AI can take your job and design trips.
Speaker 2:It's interesting with AI and I had a real fear of it in the beginning and I started studying it and listening to interviews about it people that I respected, and one of them said if you're somebody that's living in fear and not learning AI because you're scared, ai is going to take your job. Ai is going to take your job. Ai is not going anywhere. So what we have to do is learn how to have AI help us do our jobs better. Ai I can type in create a seven-day itinerary in Italy.
Speaker 2:But what they don't have they'll give ideas that are not real options. You can't use that as the Bible of travel, because the restaurants will be closed, the train won't be working on that day. But for somebody to come to me and said I put into AI that I wanted to go to Italy and I want to spend seven days, and here's what the idea is, what do you think? That's a great thing for me because we're starting from somewhere. I don't find it to be a terrible tool. I also use it to create my documents for the guests. I, I input, I write everything, I input it into there. They format it, they make it look nice, like it's like it can't write my knowledge but, it can help create a better product.
Speaker 2:I, I make myself practice, ai. I go on every day and I learn a new prompt so I can learn to be really skilled at it, so it can better what I do, and I think that you know, not everybody is in the same arena as I am. My goal is just not to be scared of it, just to make it better at my job.
Speaker 1:Right, because it's here to stay, that's for sure.
Speaker 2:Okay, well thank you so much. Much thank you for having me.
Speaker 1:I'm so happy to have somebody in the travel industry. That's very good by the way, do you have to speak all those languages?
Speaker 2:no, and I, I, uh, I speak a little bit of french, but I do not speak multiple languages, and it is a big regret of mine that, as a as a younger person, I didn't start, and not that I couldn't, but I had. I thought about making it one of my new year's goals and I had other ones that I felt like more important. So there you go, but I spoke more languages. I am very impressed by people that do.
Speaker 1:All right, kelly. All right, thank you so much. All right, bye-bye. Okay, that's a wrap for today. If you have a comment or question or would like us to cover a certain job, please let us know. Visit our website at howmuchcanimakeinfo. We would love to hear from you and, on your way out, don't forget to subscribe and share this episode with anyone who is curious about their next job. See you next time.
