Jason Lucking: From Gemology to Technology and the Future of Smarter Airfare

Intro: Broadcasting live from the Business RadioX studios in Houston, Texas. It’s time for Houston Business Radio. Now, here’s your host.

Trisha Stetzel: Hello, Houston. Trisha Stetzel here bringing you another episode of Houston Business Radio. Is my pleasure to introduce my guest today, Jason Lucking, founder of pAiback, the AI powered travel platform built for frequent fliers who are tired of overpaying for this same flight. He is a gemologist turned tech founder. Jason has spent years in the high end jewelry industry, traveling nonstop between cities, shows and clients. One day after discovering his wife had paid far less for the same flight. A month later, he asked a simple question why isn’t this process automated? That moment became the spark for pAiback. The company helps travelers get automatic refunds or airline credits when ticket prices drop. No rebooking, no lost seats and no disruption to travel plans. Booked directly with Delta, United, Alaska or American others, forward your confirmation email and payback does the rest. Jason’s story is about much more than just airfare. It’s about innovation born from frustration and how AI is quietly helping travelers save money while staying loyal to the airlines they love. Jason, welcome to the show.

Jason Lucking: Thank you, thank you. Appreciate it.

Trisha Stetzel: Yeah, you’re very welcome.I hope I did you justice.

Jason Lucking: Such flattery. I will pay you $20 at the end of it for.

Trisha Stetzel: Okay, good. I’m glad I, you know, I just want to make sure I was going to get paid. Kidding, everyone. All right. Jason. Um, tell us a little bit more about you.

Jason Lucking: Yeah. So, I mean, you summarized it beautifully. I have been in the luxury service world, predominantly jewelry for since I was 15, 16 years old. And, you know, I’ve been sat on a plane being a road warrior, like many salespeople have, um, you know, just trying to trying to live on the road and, and, and trying to make that as best of an opportunity for us as possible. And when things continued to change and you’re set on the road, you’re away from home. You know, we’re always looking to optimize our miles and our points. And, you know, there’s so many different things that people are doing with credit cards. Um, and, you know, I was I was sat on a plane and my, my house became a very expensive storage unit. Um, and, and it was, you know, how do we, uh, how do we how do we change this for, um, for both myself personally, my family. Because we do love to travel. Um, but, yeah, you know, I think, I think, um, ideas come out of sometimes unexpected moments.

Trisha Stetzel: Yeah, absolutely. So, uh, in your bio, I read, I read, I talked about how, you know, this moment where you saw your wife getting a less expensive flight really sparked, um, the moment of payback. But how did that all come together? Like, how did it go from, gosh, why isn’t this automated? And why isn’t somebody already doing this to actually doing it 1,000%?

Jason Lucking: So I, I, the company would pay for, for my travel. But just as a human being, I always wanted to optimize the right time to buy your ticket. And I tried all the fads. Tuesday. Clear your cookies. Make sure Mercury is in retrograde. Have a gluten free meal the night before. You know all the things that they tell you on on social media to do. And, and and I mean, 80% of us start on a Google or an Expedia for searching for our flights. And I was the same. I’d started on Google, and there’s a little graph at the bottom that showed what the prices had done. And I thought to myself, man, I knew I should have booked it a week ago, or you know, why did I why did I wait? How do I play this, this, this system? And and as you said, when my wife booked her, she wanted to join me on a business trip and she booked hers a month later. Like what? What kind of loyalty is that to me? Who? Who booked in advance so that the airlines know I’m going to be on the plane. They know that they’ve got my money. Um, and and it just kind of. I’m very fortunate. I come from a very entrepreneurial background. My, my dad has done a whole multitude of things my mum made us do. Logic problems as children. Maybe that contributed to it. My wife’s, uh, father created the first heated wetsuit. So all these just, you know, um, ideas, you just look at the world maybe a little differently on some things. And I was very fortunate enough that that between my own neuroses of wanting to optimize my own tickets and then seeing this, the rise of AI was, uh, a beautiful addition. It came at the right time. And an amazing co-founder who really just, you know, brought it all to life.

Trisha Stetzel: Okay. So I’m going to roll all the way back to gemologist, to technology. Like, how did that how did that shift for you?

Jason Lucking: So my dad has always been in the computer industry, so I’ve always been surrounded by computers since I was, you know, a baby. We had a we had a computer in a whole bedroom, so to speak. And, you know, we were doing, uh, we would build computers as children. So I guess from from that perspective, technology has always been even though I never saw myself as that. I was very fortunate that I got into gemology. I loved the science behind it. I loved the psychology. I loved the composition of of, uh, ultimately, I’m realizing it’s I love breaking things into parts, you know, kind of dissecting them. What makes a blue diamond, a blue diamond, what makes a spinel, a spinel, all these different things. And and that’s clearly what I’ve done with my flight ticket pricing, you know, what was it that changed the price on things? Um, I don’t consider myself a coder. Um, I’ve got way smarter people that do that, um, than I do. Um, and so having an amazing team that, that helped bring that to life was amazing. Um, being being in gemology, as you said, isn’t a natural transition into technology. You don’t necessarily think the two go hand in hand, but I was fortunate enough to work for an online diamond and engagement retailer. Um, so, you know, I’ve always bridged the gap between pushing innovation forward, whether it’s in the jewelry industry and now pushing it forward in the aviation industry.

Trisha Stetzel: Yeah, absolutely. So, uh, having the right partner is really important. So how did how did that form, uh, to bring payback to life?

Jason Lucking: Um, so I’ll, I’ll give you the honest answer here. Uh, Morgan was a student in one of the rental properties that that we have in the UK. Uh, and he was, was working on my dad has a Christmas tree rental company. He rents out live Christmas trees.

Trisha Stetzel: So that’s a great concept.

Jason Lucking: I told you, we look at the world a little differently. So you take the Christmas tree out the ground, you rent it to somebody, we take it back at the end of the season, we plant it, it grows another 6 to 12in. You rent it back again. Morgan was helping my my dad with the website and some of the social side for that. So when the idea came around, it just started off as a conversation. Um, I am a, a big believer in you don’t need to know the right people, but by meeting people, you’ll get to meet the right people. Uh, I’m a I’m a serial networker, if you would. And so I was very fortunate that when you ask somebody a question, do you know somebody that might. It led to this conversation with Morgan. And Morgan was, um, kind of starting his his development, uh, world. He’s a young but super, super smart guy. And it was just a perfect partnership. You know, it’s allowed us to continue to grow, Grow our technology, uh, grow our team. And so it’s it’s allowed him to really focus on what he does best. And it’s allowed me to focus on what I do best. So it’s a it’s a it’s a very unusual origin story. One would say. Um, but I believe I don’t believe in luck. I believe that luck is a mathematical formula. It’s opportunities times by frequency. The more opportunities we put ourselves in front of, the luckier we become. And that’s with meeting people. That’s with taking ideas. That’s why many entrepreneurs do multiple ideas, because it’s it’s not always about the first idea. It’s about it’s about opportunities, times by frequency.

Trisha Stetzel: And your name, your last name just happens to have luck in it. I’m just saying.

Jason Lucking: Yes. A lot of people say, well, you must be lucky. It’s in it’s in your last name. And I will not I will not fall short of of the, the luck of that.

Trisha Stetzel: Yeah. It happens. Um, okay, so we know the background, and I really want to dive into payback because I don’t want listeners to think it’s just another thing. You talked about the getting points and the signing up for this and signing up for that, because it isn’t just another thing. It’s really special. And for everyone who’s listening, I want you to hear that it’s spelled p a b a c k. So if you’re looking for it already, that’s what you’re going to be looking for. I’d really, Jason, like to dive into what exactly does payback do and how can the listeners start using it today.

Jason Lucking: So let’s let’s take it back to, you know, kind of the start of how it works, which is we we’re not a travel agent. You don’t book your travel through payback. You’ll book them directly through the airlines, as you said, Delta, American United or Alaska. So you’re you’re booking directly with the airlines, not through a third party, not through an online travel agent directly with the airlines. Now, once you’ve got that ticket, you forward that ticket or you sign up for payback at payback app, which, as you said, is paid back. Um, and then you forward that ticket to us. You get these instructions, you get a welcome email forward it to ticketing payback app. You can also integrate your inbox. So then you don’t even need to do the forwarding. We automatically pick up any Delta, American, United or Alaska flights. So you buy directly with the airline, you forward that ticket to us and then you have to do nothing. You sit back because we use AI to monitor the system. We check your flight with regularity every three hours. If the price of that ticket drops below what you bought it for. So we’re talking about the same flight. We’re talking about the same cabin class. None of that changes. We’re not trying to, you know, downgrade you. So you stay on the same flight in the same seat, and we then just optimize that ticket at the new price. And the wild thing is, this happens one in every two flights. And the average savings that we see, um, is $250. Now that takes into account, um, you know, economy premium and business.

Jason Lucking: So it does it does factor in all the classes. Uh, it doesn’t work for basic economy because, I mean, there are it’s the most restricted and limited ticket. Um, so other than that, you have to do nothing, and the price might drop once between the time you booked it and you take off, it might drop. We’ve seen it drop eight times on a person’s ticket. And so every single time that ticket drops, as long as it drops below, uh, above $10, we will we will collect that. Um, uh, as you said, it would be a refund if you buy a refundable ticket and it will be a future flight credit if you buy a nonrefundable ticket, which most of us do. And anybody that is a frequent flier. Same thing as cash. You know you’re going to use it on the next flight or what. We are truly encouraging and and our real ethos of payback is we want people to travel more because the more the world be that domestically, be that internationally, the more that we connect, be that with friends or family or or people that we don’t know, the better we become as a world. And not to get all, you know, deep and philosophical about it, but ultimately we want people to travel more. And so if you’ve got this $100, $250 to spend on either a flight you’re planning on taking or take one you weren’t planning on taking, that is really what we want out of payback.

Trisha Stetzel: I love that.

Trisha Stetzel: That just makes my heart warm. Jason. Just the the whole idea of bringing people together. I think it’s so very important. Okay, so we’re about halfway through our conversation right now. I know folks are already excited about connecting with you and or taking a look at payback. So what is the best way for folks to connect with you? And then let’s give the payback a location again as well.

Jason Lucking: Yeah. So the best way to connect with me would be through LinkedIn is probably my primary social that I use. So Jason looking look ING. Um, if you want to find payback online, if you just Google payback travel, that’s sometimes the easiest one. The website is payback app, which does confuse a couple of people because the app is in development. Let’s just say that. Um, you’ve got to walk before you can run as a new business.

Trisha Stetzel: Yes, absolutely. And by the way, you guys, I’ve signed up for it. It’s so simple. Like it will take you less than two minutes. Go. Especially those of you who already have tickets with those airlines directly. Go sign up and send your tickets over so that you can get your, uh, your future use of the refund when it comes or, uh, actual refund. So exciting.

Jason Lucking: The thing that we say to people is submit every ticket, right? And even though we’re focused on, you know, for airlines, we are adding extra airlines is even if you do have a basic economy ticket, you might as well submit it. It takes you two seconds to do. There’s no there’s no loss there. Um, we won’t be able to necessarily do anything with it, but if there is some change in the future, it just kind of teaches you to get into that. Um, get into that automation, I guess. That habit.

Trisha Stetzel: Absolutely.

Trisha Stetzel: Uh, you said something that triggered a question for me, which is, you know, start up. We get a walk before we run. Um. Um. This startup life is grind. Some creativity, lots of chaos. You’ve also moved in the middle of all of this. So what have been some of your biggest lessons in resilience since you launched payback?

Jason Lucking: Um, having an amazing support network. And that shout out would be to my wife, who allows me to have two full time day jobs with two children, two and four, spend time with her and move and try and keep some level of sanity by working out at 5 a.m. in the morning and being awake till two two in the morning. So having an amazing support network, whether that is is family, whether that is the team that is around you. I had a long call with our team yesterday who said, you need a break. You. You need a break. Um. And and I love, I love payback. I love what we’re doing. And I love the deep rooted element of it. And so we ultimately do what we love. Um, and so I’m very fortunate that I have that opportunity. Um, but having that support network, I would say, is super key because you are going to be told no a lot. You are going to be ghosted. And I’m 38 and I, I’ve been married for coming up to ten years. I don’t remember the last time I got ghosted. You know, I realize it’s it’s 20, 25 here. Uh, ghosting is a real thing, but there is a level of respect that I apply to people that reach out to me and in kind, I. I expect it back, but that isn’t, unfortunately, the world. So you’ve got to be you’ve got to be an irritating optimist as well. Um, which is, which is, um, how how I’ve been described in the past because you’re going to get told no a lot, and you gotta dust it off real quickly and jump back on that horse and, um, you know, keep going.

Trisha Stetzel: Irritating, optimistic. I would like to adopt that. Can I borrow that? It’s lovely.

Jason Lucking: I know that my optimism is both a pro and a con. Uh, I love being optimistic and and looking at things with, you know, with rainbows and unicorns as it’s always described. Uh, but that isn’t always fun when you’re not feeling tip and top. And all I do is paint a great face of, of optimism on it. So it’s a little irritating at times. Um, but as a entrepreneur, I believe that you’ve got to have that, uh, chutzpah to, you know, to to enter the room and ask somebody and expect them to say no. Uh, and bring straight back up.

Trisha Stetzel: Yeah, absolutely. And, you know, I, I think that that positive energy brings more positive energy. You and I met because we were supposed to meet. And we both have that positive energy. Right? We’ve put that out there in the world. And I think it’s so important. So, um, how important is transparency and relatability when you’re introducing something new like payback?

Jason Lucking: Yeah. So our two biggest cruxes with payback is learning because people don’t even realize they can do this. Um, so there’s learning and there’s trust. As much as we’re a technology company, we believe that we are a service company first. And that is because flights are super important for people. Um, you know, you’re taking whether it’s a work trip and you have to be there. It’s a family trip, and you definitely don’t want those plans messed up. So we believe that we are service first, not just technology. And that has been a very pivotal point for us. Um, you know, through through all this.

Trisha Stetzel: Mhm. Absolutely. So I know a little secret. You’ve got some cool things happening or some projects brewing for next year that may or may, may or may include the veterans space. So can you talk about that.

Jason Lucking: Yes definitely. Even though we are a for profit organization, as we talked about, we want people to travel more. We want people to to expand outside of, you know, just being on a plane for work perspectives. We have, um, we believe that we have a responsibility to give back. And my wife’s father served in Vietnam, and she sadly lost him when she was very young. And it’s always been an important thing to us. And so we are, um, working with an organization that’s based on the West Coast, uh, called Operation Surf. Um, they do, um, uh, uh, almost PTSD work through surfing for veterans. And so for us, um, wanting to provide a service for veterans or at least gain some, some additional benefits for veterans, um, to allow them to, um, whether it’s lowering their cost of their existing flights, whether it’s providing them the opportunity to travel, uh, those that have served and those that have given, um, which I know you have, I I’m British, right. It’s a it’s the military is a little different in the UK. We have it. But I could not comprehend submitting my life to sacrifice what I don’t know could happen for the protection of others. And so for us being able to provide something to the veteran community, um, which is a project that we’re, um, launching towards in 2026, um, as an, as an initiative, because, uh, if we’re not doing good in the world, then what’s our purpose?

Trisha Stetzel: Mhm. Absolutely. And thank you for going down this path and really figuring out a way to give back and serve the community, uh, through this business that you’re building. So what’s next for payback?

Jason Lucking: Well, as we mentioned the the app is in development as well, which we see as a big a big up for us. Um, we’re also looking at other industries, um, hotels, car rentals. There’s some exciting partnerships that we have in the works right now that would really, um, really boost the direction of payback. And, you know, early 2026 is where we’re we’re projecting for those to land. Um, I know that’s that’s the most vague statement I could probably give. Um, but the growth, the growth of, of payback is, is in a real exciting direction for, for the new year.

Trisha Stetzel: It’s very exciting. All right, you guys, if you’re excited about this opportunity to save on your tickets, go to payback app and its payback app and sign up. It’s super easy. I’ve done it. It’s amazing. I can’t wait to save on my flights in December. I know Jason knows that I’ve got some some travel coming up I’m very excited about. Um, so. What you’ve turned just a frustration with travel into a company that helps thousands of people fly smarter. Right. And help us save money and get refunds. Um, have money available for the next flight. What would you say to those entrepreneurs out there who are sitting on their own aha moment, but have yet to take the leap to build something from it?

Jason Lucking: Um, ultimately we had we had entrepreneurs risk when we first started, you know, we thought we needed to get it perfect before we did anything. Um, two things I would say. You just got to go for it. You’ve got it. You’ve got to get 80% of the way there. The balance of the 20% doesn’t matter. Take your idea. Get it 80% of the way there and just go put it into this, into this user cycle loop. Put it out. It’s going to break. You’ll fix it, whatever it is. But what comes with that as well? And somebody said to me, uh, recently I did this very novel pitch idea called The Cut. And what they do is they give you a bad idea or a failed business, and then you get to pitch your actual business, and you get 15 minutes to make up a fake pitch for the business. And I took the idea and I flipped the idea upside down and turned it into a completely different product. And what came out of that was, everybody says, if your startup hasn’t recreated itself probably three times or pivoted in some way, then you’re probably not going to succeed. And and that’s ultimately what we’ve done with payback. We started off with, you know, saving money for, for for people with flights. And what we’ve realized through all of this is we’re actually turning price drops into loyalty for the airlines.

Jason Lucking: So we’re actually here for the airlines to boost their growth and revenue and, and make you travel more. But what is what comes out of that is people are able to optimize their flights, they’re able to travel more. So we have really changed our, uh, business direction as well. You know, a bit of a pivot, thinking it was about saving dollars and cents for the customers. And what we’ve realized through, through our research is, um, is that we are as 50% here to grow the airlines as much as we are for the customers. So the two things I would definitely say, you just got to go for it. Um, the other one is don’t be afraid to pivot. Um, and I will throw one final third one is don’t be too close to the baby. You might have an ugly baby, you might have a really pretty baby. But you will always think that your baby is really pretty. And that’s the point of pivoting and putting it out there. So I would say put it out there. Don’t be afraid to pivot, but realize your baby might be ugly. It’s okay to pivot and realize that not you need a new baby. That’s the worst thing you could probably say, but pivots in order to make sure that, um, you know, maybe your idea isn’t the number one idea.

Trisha Stetzel: I love that. So what I’d like to leave with and you’ve you’ve described this, but you didn’t actually use the coined phrase that I know you use, which is loyalty loop. Uh, why don’t we leave with a note on that loyalty loop?

Jason Lucking: Yeah. So one thing that we have realized with with loyalty, the airlines are in this a little bit of a plateau in terms of loyalty. Now, what ends up happening is people are moving a lot between airlines, whether it’s price specific, if you’re in a specific hub, you might be more loyal than the others. Um, I personally have shifted my loyalty from one airline to another. And what payback does is it really builds your loyalty with them for two reasons. One, you feel better about that flight? Every single time you get a price drop? Be it $10, be it $100. We’ve saved somebody $9,000 on a ticket, right? So, so so you get that dopamine hit every single time I feel better about my trip, I feel better about the flight, and I feel better about the airline. Now, there is also a forced loyalty that exists because now you have a future flight credit to use with that airline. There are worse things to force upon you. You know the worst things to say. Hey, I gotta take another trip. Um, so for that reason, the loyalty element with the airlines is super key. Um, to us, um, for our continued, you know, success of this company.

Trisha Stetzel: Absolutely. Jason, this has been so much fun. I appreciate you spending the time with me one more time. When you tell folks how they can best connect with you.

Jason Lucking: Yeah. Connect with me on LinkedIn, which is Jason looking, or if you, uh, Google payback, travel AI back or just go straight to the website which is payback dot app.

Trisha Stetzel: Awesome. I appreciate you, this was so much fun. I you may have to come back and let’s talk gemology because I have some interest in that too.

Jason Lucking: Happily.

Trisha Stetzel: Would love that. All right you guys. That’s all the time we have for today. If you found value in this conversation that I had with Jason, please share it with a fellow entrepreneur, veteran or Houston leader. Ready to go or somebody traveling? Be sure to follow, rate, and review the show. It helps us reach more bold business minds just like yours and your business. Your leadership and your legacy are built one intentional step at a time. So stay inspired, stay focused, and keep building the business and the life you deserve.