101. Behind the Points: How the Travel Mom Squad Built a Thriving Travel Business

Welcome to Point Me to First Class, the only show for employed professionals, entrepreneurs, and business owners who are looking to optimize their higher-than-average expenses to travel the world. I'm your host, Devon Gimbel, and I believe that your expenses are your greatest untapped asset if you know how to leverage them. Ready to dive into the world of credit card points and miles so you can travel more, travel better, and travel often? Let's get started.

Hello, everyone, and welcome back to the Point Me To First Class podcast. I have something very special for you today because I'm being joined by not three, but three incredible points and miles experts for this episode. My guests today have become a go to resource for women and families looking to turn their expenses into travel using points. And they are known for offering practical advice to make travel easier and better. Not only that, but these women have built one of the most successful points education platforms and businesses in the industry.

And today we're going to be getting a behind the scenes view at exactly how they did it, including milestones, challenges, and lessons learned along the way. We're also going to hear their top tips for award travel. That is right. I have none other than the entire Travel Mom Squad here today, and I cannot wait to bring you this conversation. Pam, Jess, Alex, welcome to the podcast, ladies. I am so thrilled to have you here today.

Alex: Thanks so much for having us. That was like the nicest intro ever. I'm like, oh, I'm like blushing over here.

Jess: You can't see us, but we're blushing and we're very flattered and we're very grateful to be here and we are just obsessed with Devon and everything she does. And so when she invited us on, we were like, of course.

Pam: Absolutely. It's an honor.

Devon: Well, thank you ladies so much. I'm really looking forward to this conversation because I think it's going to give people a look at something they don't often get to see, which is what does it actually look like to start a business around travel, to run a business, and to have one of the most successful businesses in this industry. I know I'm definitely here to learn, and I can't wait for you to share all of your insights with everybody. But just to kind of take a step back or introduce you more formally. Can you guys tell us a little bit who exactly is Travel Mom Squad and what is your mission as a business?

Jess: All right. So Alex is the one that actually started Travel Mom Squad. It was actually Travel Hacking Mom back then when she started it. But I think our mission is just to empower everyone. But we primarily focus on women and moms to make travel accessible for their families, even if they think they can't afford it.

You know, when we got started, all we saw was men in this industry. We saw a lot of single men flying business class, and that's great, and I'm happy for them, but I couldn't relate to a lot of what I saw. And so I kind of started my own thing. Alex started her own thing. We ended up merging, which we will get into all of that.

But we all had, I think one of the reasons it worked so well for us to merge is because we had the same mission and goal to really, you know, women make 80% of travel decisions, but all we were seeing in the world travel space was men. And so, you know, to just be that, be those people to be like, okay, if they can do it, I can do it. And so that's really our goal.

Devon: Yeah, I think that's so relatable. You know, I think we have all been learning about points and miles for about the same time. You know, I kind of started learning about this in like 2013, 2014 and I had the same exact experience you did. There were some amazing information and blogs out there on the internet. I'm so grateful those existed and I learned from them.

But it was really fascinating to me to feel like just one side of points and miles was being shown. And I think even on the earning side, I realized I was hitting up against a wall. The things that I was looking to do in terms of earning points or stuff that was happening in my life, I was like, I don't find any information here. You know, who's here to teach me about how I can leverage certain expenses? Or like you said, what does it look like to travel if you maybe aren't traveling solo or you don't have complete location or time flexibility in terms of just snagging the one single award that might exist, you know, for a flight that you're looking for.

And so I can relate to that sort of gap in the market as a consumer and really kind of going through a phase of wondering, wait a minute, where's the education for somebody like me? And Alex, I'm really curious to hear from you because Jess mentioned that initially you all started separate businesses or separate platforms. What was it for you that first sparked your interest in award travel and how did that passion grow into your just initially starting the business that is now Travel Mom Squad?

Alex: Yeah, so I had a friend in college and we stayed good friends after college for a while and I would see her post on Instagram. So at this point, I think I'm, you know, married. I maybe have one or two kids. She's married, has a couple kids. Her husband's in law school and they're traveling to the Maldives. And I'm thinking like, how? Like I know you can't afford this. You guys are a young married couple in law school. How are you in the Maldives right now?

And she would just, you know, message me back like, oh, like my husband's figured out how to use credit card points. I'm like, I know how credit card points work, but I don't know how to do what you're doing. And to me, the idea was extremely overwhelming. And I couldn't grasp like, okay, but like how, like you get credit cards, but then how do you go to the Maldives? And I didn't understand that, oh, they're getting more than one credit card. They're earning sign-up bonuses.

It's kind of funny. The other day, I actually was going through old screenshots, and I had a screenshot on my phone from like 2013 where she was explaining to me what they do. And I read it again. And I'm like, this makes perfect sense to me now. But when she sent me that Facebook message in 2013, I was like, whoosh, right over my head. So confused by it.

So that was like my first introduction. I knew it existed, but I didn't know what to do with that knowledge. I don't even think I, I didn't have any knowledge. I didn't know what to do with that information.

So then, you know, a few years later, I see somebody posting about it on Instagram and how it works. They had a blog. They don't exist anymore. They didn't keep going. But it was a very, very simple... Just explained it so simple that I hadn't seen it broken down so well before. So I was like, okay, I'm going to do this. And so I dove in and spent a lot of time. I kind of had this assumption that I needed to know everything, which I don't think is correct.

You can just know a little bit and then grow on that. And I had a notebook full of notes. I was reading Reddit message boards. I was like trying to figure it all out and didn't need to do all that. I spent a lot of time learning things I didn't need to know as a beginner. And so from that, I start traveling on points. And of course, the natural thing is people that know me are like, wait, how are you all of a sudden traveling like this? How is this happening?

I started to explain it to them. Their eyes glaze over and I'm like, hey, don't worry about it. I'm going to send you this blog that taught me how to do this. You're going to be golden. They break it down so well. I go to share the blog, and it's not there anymore. So I'm like, okay, well, the people I learned from, he had just started a new job. It was just a fun thing they were doing on the side to teach people. And then they were like, okay, we're moving off my professional career here now.

So I thought, you know what? Like I had friends tell me, you should start teaching people how to do this. And I thought, oh, there's already people out there doing this. It's too late. You know those things we tell ourselves of, oh, I couldn't possibly do this, you know, major imposter syndrome.

So I figure, you know what? So many people told me this. I can't find the right resource that I'm looking for. I guess I'll just make it. And I went through back and forth a lot in my head, like, should I do this, should I not? And I'm like, you know what, I'm just going to do it. It'll be fun. I'm passionate about this. I love teaching people about this.

And I got actually what happened is I kind of got tired of texting people. And like, if I could just write this on a blog post and send them a blog post, I wouldn't have to rewrite this all the time. So that's what I did. I created a blog and I thought, how am I going to get people to this blog? I need to create an Instagram account. That was major in putting yourself out there. I felt stupid.

Are people going to think this is dumb that I'm starting an Instagram account? I don't want to be a "influencer". That's not really my personality. But I just went for it. And I did it and would never have guessed that it would take me here.

So then after, you know, I'm doing this by myself for six months, it was time consuming and overwhelming. I'm putting out one blog post a week, if that. And I had introduced my mom to this hobby as well. And she, being retired, had a lot more free time and flexibility to travel more than I could. And I'm thinking, if I want to teach people how to do this, I need to travel more. And I can't really travel more right now when I have babies. It was just challenging. And so I said, Mom, do you want to do this with me? And you can write trip reports and you can write blog posts. And she was all in.

And then, you know, that was fantastic. We were just you and I did it for how long, mom, together? Maybe.

Pam: Well, I think it was at least a couple of years. It was like, you know, two or three years.

Jess: I think it was three years.

Pam: Yeah. And then we didn't do much. We weren't making any money. We had a lot of referral points, but we just loved it.

Alex: We did and then my mom. Mom, do you want to share about how Jess because that was her epiphany?

Pam: Yeah Well, you know the other thing I wanted to say is that this was right up my alley. I love to travel. I remember I was a nurse in my prior life, my prior career, as we say. And so I would always be working extra shifts. I was the queen of saying, I want to go here. And my husband said, how are you going to pay for it? And I said, I'll work an extra shift. And everybody would joke, well, there's only so many hours in a week, how many extra shifts can you work? But that's how I would fund it.

So then Alex heard about this. I was like, this is amazing. This is what I need to do. And I'd been an extreme couponer in the past, so I traded free shampoo for nearly free trips, which was definitely a win-win. And so Alex and I just kind of plugged along. I was writing the trip reports. I was, you know, we were kind of divided up stuff. But she was a busy mom and there was only so much that she could do and only so much that I could help her do.

And we met Jess at a meetup for women in the industry, and Alex and her just became really good friends. And about this time, reels had started, and Jess had just started, but her viewership was amazing because she put out really good reels. And I remember, I'm a very competitive person, and so I would look at her and go, oh, look how many, you know, views she has. Wow, she's really growing and, you know, be kind of, you know, competitive.

And I was one day, because they were really good friends besides just knowing each other and their friendship had really blossomed. And I remember being in the shower one day, and I get all my best ideas when I'm in the shower. I think because I can be a little type A and I just think in the shower. And all of a sudden it came to me, what if we didn't compete against Jess? What if we joined forces?

And so I called Alex up and I says, you will never believe what's going to come out of my mouth. And after I told her, she says, I never would have thought you would say that.

But I said, what do you think we invite Jess to be part of TMS? And that's where it came from, that epiphany in the shower. And I got to say that, you know, we didn't know Jess that well. And partnerships can be tough. I would say this could go down as one of the smoothest partnerships in the world. We are all different. It isn't like we are all exactly the same. And that is the beauty of it, I think, is that we all offer different things. Jess came in with strengths we didn't have, and it has been pretty darn seamless. It has been the best epiphany I ever had in the shower.

Devon: You know, I think it's so fascinating to hear. I'm sorry, Alex, to cut you off. Oh, go ahead. I think it's so fascinating to hear, you know, from a total outsider perspective about how this kind of organically came together. Because I think I found you guys after it was the three of you.

You know, I didn't know any of the backstory. You had a little bit of a different business name at that point. Maybe we'll get into that if you want to talk about that a little later in the episode. But I think what's so fascinating is that when I was first introduced to your work and who knows how I stumbled upon you, it just seemed like such an obvious organic partnership from seeing the three of you work together that I didn't realize that you had started out as, you know, kind of separate entities and then had merged together. And Pam, like you said, I think partnerships can be tricky.

You know, partnerships between two people. Now you add a third person in. And I'm curious, what is it that you think made that partnership so successful when it could have been very challenging to try to merge the three of you together?

Jess: I still remember when I was at home and Alex texts me and she's like, what would you think about coming over to Travel Hacking Mom? And I was like, what? We had kind of joked before, like, oh, one day we should like join forces, you know, but I didn't think it was going to materialize as quickly as it did. I think all three of us have really similar work ethic. Like we are all hustlers.

And so I think that really helps. Like if I didn't work as much as I do and they brought me on, they'd be like, Hey, you need to pick up the slack. Like, what are you doing? You know? So we are all hustlers and we each have our own unique perspective.

Like obviously Pam is a retired 70 year old grandma, 21 grandchildren. And so she's doing a lot of like traveling with her husband or her sister or her friend. And then I have a blended family of six. And so we have all sorts of different configurations when we travel.

Alex has her family of six. And so I feel like our strengths are that like we all have similar goals, but we achieve them in different ways and we're able to offer different perspectives. And so we offer a little bit of something for everyone.

Pam: You know, and I think one of the strengths too that we've had is that I think a lot of people say, oh, you could travel here and there, you could do this, and maybe you go on one or two trips a year, but we really travel a lot. Between the three of us, we are showing people how to book, you know, 20 to 30 trips a year. And so I think that we walk the walk instead of just talk the talk. We actually really walk the walk. We love it.

We're passionate about it. We're passionate about using points and miles. And I think that in all the trips we take, it shows.

Devon: Yeah, I, again, as just someone who's a fan and an outsider of your work, I think that's some of my favorite things about you all and the work you do is that not only are you so relatable, also because you're three distinct people. And like you said, you have different lives, you have different travel circumstances. I think it's wonderful to have all of those different examples about how can you travel? What are the challenges you face? How do you overcome them?

But I think one of the kind of roles that you all occupy so, so amazingly well in this space is that you can be really inspirational and educational without ever being condescending or without ever being what feels like judgmental, you know, in terms of what you teach or how you teach it. And I think that that's something that really can't be, like, overestimated how important that is, you know, to be able to put out information that folks feel like they can really hang on to and use, but never feel like they're being talked down to.

And I know that that's something that can be, I think, challenging in a space. And so I love that you all strike that balance really, really well. And I'm curious, can you just remind us, when did the three of you actually formally come together as Travel Hacking Moms?

And when you first started out as this trio, what were some of the first wins or breakthroughs that made you realize that this could really become something big?

Alex: Was it August 2022?

Jess: So they started Travel Hacking Mom in fall of 2018. Yes. And then I started, so my prior account that still exists is Made Possible by Points. I started that in July 2021.

And that's just because I was depressed because of the pandemic and not being able to travel. And I was like, I was not ever anticipating like monetizing it or it becoming my full-time job and like quitting my job as a lawyer. Like none of that ever crossed my mind when I started my account. I just started as a hobby to share my love of travel hacking with everyone on Instagram. And so I started that in July 2021.

And then a year later is when Alex sent me that text. And then I was like, are y'all serious? And so we met, we had to like get a lawyer to draft up on, you know, all those things. But I think August 2022 is when we formally announced the merger. Yeah.

So over two years ago now.

Devon: And what were some of those first milestones in growing your platform? And when did you feel like you were really starting to gain some traction as this group of three?

Jess: I think Alex had said like, so we were each independently making income on our own. Like by that point I had quit my job. I was making, you know, a full-time income off of, off of my Made Possible by Points account, Alex and Pam, same thing. And I think Alex said like, okay, when you join, we anticipate that, there's gonna be a dip in revenue because now we're gonna be splitting it between the three of us instead of just the two of us, and I don't think that ever actually happened. 

Alex: There was never a dip. It just kept getting better and better and better. So that was a very welcome surprise. And I think part of it was just like, we just worked really hard together.

And a big thing of when we merged was Jess had just created a course. And she had put a ton of work into it. We had a course as well. Ours was a much cheaper, not as, I would say, it was more basic. Hers was more in-depth course and it was reflected in, you know, her course was more expensive and she was like, "Hey, I just put this course out. I like put a lot of like, a lot into this course. I don't want to merge and just let go of that course."

And we're like, "Well, let's look at your course." And so we're like, "Nope, we love your course. We will drop our course and we will rebrand your course and add to it." We re-recorded all of the modules. We added some new things to it and we've continued to do to add to it.

But that was kind of a win as well when we realized, okay, like, yeah, there's some obstacles here of, okay, how are we going to logistically make this work? But we figured it out. And we relaunched that course as, I mean, same name, just with like the new branding and colors of World Travel Academy. And our course launch went amazing when we relaunched it.

So that was a huge win for us that like, okay, people were very receptive. And I think part of that is we have similar teaching styles. And so when we merged, we had a lot of crossover with some of our audience and people were so excited about it. They're like, "Oh, this just makes so much sense." And so that was a huge win for us to have that reaction of people being just as excited about it as we were.

Jess: Yeah, I was kind of nervous. I was like, what are people gonna think? Are people gonna be like, "Oh, well, they're not the same anymore. So like, I'm done with them." You know, you never know how people on the internet are going to react to things.

But like Alex said, like we were blown away by the support and it was, we got so many messages of people saying, "I love you both. And like, I'm so torn about who's linked to apply through and now I can just apply through like your link together." And I'm like, oh, that makes me so happy that people care that much, you know? Yeah.

Devon: Yeah, I think that is something that has always really struck me about the work that you all do is that you have a community and an audience that is really engaged with you and loves what you do, loves how you do it, and I think feels really personally connected to you. And I'm really curious to hear, you know, as you expanded, especially after the merger, when the three of you came together, what were some of the most important strategies that you all have used to connect with your audience and provide so much value to them?

Jess: I think we've always really just like, number one, just stayed true to ourselves and our messaging and like trying just to be as authentic as possible. But also we are still very much involved in this business. We have a few people on our team now, but we are creating the content, that's us. We don't have a VA, we don't have an assistant making our reels. We are making our reels.

Pam is writing our newsletter every week. Alex and I are personally responding to the hundreds of DMs that we get every day. We don't have an assistant in our inbox responding to DMs. We want it to feel like us, you know? And so I think that has just been really important, is like us still being engaged.

It's not like we blew up and we were like, "Okay, we have this business now, we're gonna just outsource everything and just be hands-off." Like, that's the complete opposite of what we've done.

Pam: Yeah. I'd say that the people that we have brought into our team, our background players, they aren't right out there. It is still us. It is still our voice. It will, you know, and we have no intention of that ever changing. It will always be our voice.

Devon: Yeah, I think it comes back to that idea, just what you were saying about your authenticity, that this business is really built on the three of you living your actual lives, sharing your actual travels, and teaching other people how you've made it possible for yourselves. Now, up until this point, I think it's easy to hear this story and think, wow, this was just an overnight success. It has only ever been like one win after another. You know, these three incredibly talented women create this wonderful business. Seems like everything is going right.

But I'm really curious to hear from you. Have there been any unexpected hurdles that you all have faced, you know, in your business? How did you overcome them? How did you handle them?

Alex: Well, I think the first hurdle for myself, and Jess might relate to this when she started making possible at points, was just getting started and getting over that imposter syndrome and deciding to actually try to do this. Learning how to create a blog, watching YouTube videos, not liking the way things looked with the templates. I'd be like, I've got to learn how to do basic coding. And if you asked me how to do that today, I'd say, I don't know any idea how to do that. I'd have to read.

I mean, that was what, like six, seven years ago. I have no idea how to do that anymore. But not being afraid to learn new things was a huge part of that. I also think, you know, Mom, maybe you want to touch on this because the big thing for us was that we didn't go into this thinking, we really hope we blow up and become this big resource out there.

Pam: No. It was really just, I remember when Alex called me and asked me if I wanted to do it, I go, oh yeah. I would love to talk to people nonstop every day about the trips that I take. This just sounds so fun, but people really aren't interested in hearing about my trips.

So this was like an outlet that I could talk about, you know, that I use point somewhere. I mean, it's a whole different language for most people. Most people, like Alex has said, their eyes glaze over. And so it's like, I could talk to an audience that would understand this? This sounds like a dream thing to me.

I mean, at this time, I'm in my late 60s, and this is a whole new thing for me to do. And I was so excited about just jumping in and doing it. And like I said, we, for the first couple of years, we didn't make any money. And we would just get some referrals. And I remember we'd say, you know what?

I don't care if we never make any money. We are passionate about this. A few referrals is amazing. We will love this. So I think that's a huge thing is just to be so passionate about what you're doing that you don't care if you make money.

And I remember one month, there was this month that we made this minimal amount. And then all of a sudden, the next month, we made a much more substantial amount. And like we were blown away. It was like, you gotta be kidding me. We can make money?

It's like, and I remember just telling people about it because I was so excited and I said, but this will never happen again. This is a one-off. This will never happen. But I think that was the thing is like, we went into it not expecting it to be a career or that we were going to make substantial money with, but we just had a passion for it and we loved it. We loved what we were doing and we just kept doing it and we kept being very, very consistent with what we were doing.

Devon: Yeah, and part of that was during the pandemic too. So it was like, you know what? We don't even have a whole lot of stuff to really talk about, but we still enjoy this. So let's just keep plugging away here. And so that was a hurdle in itself was do we keep going during the pandemic and having this?

Like we, I think at the time on Instagram, we had maybe 3,000 followers and we were like, you know what? We love this and the pandemic will eventually end and we're going to keep earning points during this time so we can travel when it's over. And yeah, I mean, we've had some other really major hurdles we had to cross, most namely, Jess, you want to cover our biggest one that literally we were like, how, what do we do now?

Jess: Yeah, I definitely don't. I mean, it's been for the most part great.

Pam: It was a nightmare. 

Jess: This has been for the most part really great, but I will say that 2024 has been like a year on the struggle bus for us. And we are not sad to put that behind us. It's been an amazing year business wise, but also it started out with, so like I said, our name used to be Travel Hacking Mom. And then in January, it was like end of January, early February, we found out...

Alex: It was actually Jess's birthday.

Jess: It was my birthday. We found out. So we have affiliate links, like we said, through the banks. That's how we make a big chunk of our revenue is through those affiliate links.

When people apply through our links, we earn a cash commission, not just referral points from that. And so we have links through Chase, Amex, all the major banks, but Chase is really the one where we make the biggest chunk of our revenue. And Chase basically said, we are not going to allow anyone with the term hack or hacking in their name to continue to have affiliate links. And so we were like, okay, well, our name is Travel Hacking Mom, so that's an issue.

And so I think we had around two weeks to completely rebrand our entire business. And it's a blur in my mind still because I don't know how we did it. But we basically met with a brand strategist and we were like, here's our name. Here's our mission. Here are our goals. We need a new name that people will still love, but that doesn't have hacking in it.

And so we met with him. That's how we came up with Travel Mom Squad. We still wanted obviously mom to be in our name because we're a group of three moms. And then travel, obviously, that's a huge part of what we do. But then he was like, so what's the next biggest component of your business?

And I was like, it's our community. Our community is everything to us. We wouldn't be where we are without them. He was like, okay, I think you need a third word that's like team or squad. We were like, squad, travel mom. It was kind of like a light bulb moment.

We had to take hack and hacking out of our podcast, our blog with 600 blog posts, we had to change our name on Instagram. We had to take down every Instagram reel or post that mentioned hack or hacking. And that was our biggest struggle. Like for sure.

Alex: 1000%. And the scariest part of it was our Instagram name switch didn't go smoothly. We ran into some like glitches and issues with Instagram. And so we were unsure if it was going to switch.

And at this point, I believe we had, I don't know, 350, 000 followers maybe, somewhere in that range. And it was like, I've had this account here for years and years and years. And if we can't monetize it, then what are we going to do? Anyways, I mean, the good news is we got it sorted out, but it was a very, very stressful, like 2 days waiting on that name change to go through on Instagram. And I remember like Jess texted me, she's like, it's fixed.

She like was able to get a hold of somebody and we got it all figured out. But it was a high anxiety week for us.

Devon: Yeah, I can't even imagine honestly, because knowing the extent to which your business was affected by this. You know, I can't imagine there was a single piece of material that you all had created that didn't have the fingerprints of the word hack on it because that was the name in the name of your business. And folks listening to this, whether they own and run their own businesses, they're employed and they have other projects going on in their life. I think something I would really love to hear you all talk a little bit more about is, I imagine that maybe there was a conversation amongst you three, or maybe individually one of you thought, oh my gosh, is this worth it? Like, is the amount of effort it's going to take to rebrand our whole business and to go back into every piece of content you've ever made to make it compliant with these new rules, is this something that we're really committed to doing?

Especially on, like you said, like a two-week timeline. This was not something that you had a year to prep for and plan for. What was it that allowed you all to look at this challenge and say, we're gonna take this, we're gonna tackle it, and we're gonna move forward with this. What made that possible for you all?

Jess: I don't think we ever had a conversation like, should we just give up? Should we just, like, abandon ship? We are all very, like, strong, stubborn women, and we're like, we're not going down. Like we are not letting this bump in there. Now I can look back at it and say bump in the road.

At the time it was like a mountain that we had to climb. But I was like, we have put too much into this to just let it go. I don't think that was ever even an option for us. It was just like, are we going to lose links for a month? But yeah, we never considered quitting or just not rising to the challenge.

Alex: I think a huge part of it too for us was knowing I'm not doing this alone. Like I don't, it's not just me having to figure this all out. If it was just me, I would be sitting in a puddle of tears. I mean there was moments still where I wanted to sit in a puddle of tears, but I knew I had people with me. We were in this together, and between the three of us, it's like, okay, we're going to rally.

We've got this. I mean, we have this hysterical video. My mom was actually at my house when this was all going down. Just by coincidence she was visiting and she's in my kitchen and she's going we got this squad go team go and I was recording it I sent it to Jess. Jess uses it when we as like promotional material now. So she took our suffering and turned it into like a video she shares when we're like doing a core cell, which is hysterical.

Jess: But you can just tell in the video that Pam is like delirious from removing the word hack from like 600 blog posts. And she's like, go squad, go. I don't know. It was just so Pam and...

Pam: Yeah. They love to make fun of me.

Alex: So I think that was a huge reason why we can push through these obstacles is we have each other and we're all like Jess said at the beginning, we're all very much like go-getters, hard workers. And it's like, all right, let's buckle down. We're going to get this done. Like, we're just going to do it. Whether this is terrible or not, we're going to figure it out.

There's always something we can do to figure it out.

Jess: And we actually use it as like a baseline. Like every time an obstacle sense has come up, we were like, if we can rebrand in two weeks, we can do this. If we can change our name in two weeks, we can do it. So it's like, yeah, we just use it as our, as our go-to. Like if we did that, we can do anything.

Devon: So it sounds like the rebrand was something at the time, maybe not the obstacle that you would have chosen to tackle head on, but you guys came out from where I'm standing, it seems like better, stronger. Everything has just continued to grow in your business since you all became the Travel Mom Squad. I'm curious to hear from you all looking forward, where do you see Travel Mom Squad in five years and what's the next big goal that y'all are working toward?

Jess: I was actually joking. So we're actually all together right now in Mexico. And I was joking about this at dinner because we were going through your questions. And our goal is to be like The Points Guy, but for women and families. And so we want to be a household name.

And I said, I want someone to bring up The Points Guy and this woman to say, who's The Points Guy? I only know Travel Mom Squad. Like that's my goal. It's like that people don't, not that we have anything against The Points Guy. Like that was a crucial blog and me getting started in this business.

But I just feel like we want to be a household name. Personally, I want us to get on the Today Show or Good Morning America. If anyone has any connections, that is my goal. Yeah. 

Jess: Well, what we were joking to at dinner was like, I want someone to say, oh, The Points Guy, oh, so that's like Travel Mom Squad, but for men, right? That's our goal. But like Jo said, Points Guy is a great resource, done amazing things for people in points and miles and like kind of paving the way in the industry for us as well. So another thing we were kind of talking about dinner the other night was, you know, it hasn't it's been six years I think since we first started since I started Travel Hacking Mom.

That was six years ago. If you would have told me that this was where we would be now, like a full-time job with a team, and I would have been like, no way, you're joking. It's literally impossible to imagine what the next five years will bring because we wouldn't have even imagined this. So I'm very hopeful that we'll be even bigger and helping more and more women and families make their travel dreams come true. That's the hope.

Alex: Because that's the thing for, I think for all of us is when we hear success stories from people, we get more excited about that than we do about our own successes. We've been doing this long enough. We know how to do this, but being able to teach someone else, change someone else's life, for them to send us a message and be like, it doesn't even have to be an extravagant trip. My mom got diagnosed with cancer, and I was able to travel across the country and be with her. Or my sister graduated from college, and I was able to fly there and be at her graduation.

Or, you know, the big things, like we took our first family trip out of the country, and like it was made possible by points and miles. Like, I never get tired of people emailing us or writing in our Facebook group or DMing us about those successes.

Devon: It is so incredible to hear those stories. And I think that's one of the things that, again, just makes your community as amazing as it is, is how much time and dedication that you all have put into what you've created, how invested you are in the success of the people in your community, and I think hearing those stories and knowing not that you're responsible for it, but that you opened a door to show people, you know, this is an option. These are things you can do and helping them and walking them sort of walk through that doorway, I think is probably got to be one of the most gratifying things about your business.

Now, thinking about the future as well, if it's one thing that we know about points and miles just in general, and I think this is also true of the points and miles educating space is that it is very dynamic and very quickly changing. I'm curious to hear from you all, how do you plan to keep innovating in your business and what do you think is going to be some of the biggest challenges for award travelers and educators in the next few years?

Alex: Well, I think one thing we've talked about is just, you know, being okay with the fact that yeah, like things do change in this industry and you have to adapt to it. And so we hear, you know, you hear a lot about like, oh, this airline devalued or, you know, this hotel chain got rid of their award chart and things like that are going to happen and continue to happen. But on the flip side, we've also never seen welcome offers as high as we've seen them. Like 2024 was a crazy year for welcome offers. Lots of those cards had best ever welcome offers.

And so realizing like, hey, yeah, things might change but there's also some things that kind of make up for it and make it better. And also realizing that, you know, I'm gonna get into this and get as much out of it as I can while it's good and not kind of looking at the glass half empty sometimes.

I think people do a lot of that work. I don't know. Is it even worth getting into points and miles now? Credit card companies have these different rules and it's like, I'm going to take what I can get. You know, if I get one free trip, that will be worth learning how to do this, you know?

And so I think that's a big thing for people, you know, going forward is just adapting to that change and not letting it kind of bog you down and feel like I'm not even gonna do it kind of attitude.

Jess: And then as far as challenges for award travelers, I think while some of these tools that we have access to now are very helpful. They also sometimes make it harder to snag award space, like the alerts and being able to set an alert when a flight becomes available, being able to set an alert when a hotel becomes available. I personally love those tools, but they also, you know, people are more aware now than ever, like when availability opens up. And as we know, there's only, there's not an infinite amount of award availability.

And so I do think that plan, especially if you have a family, planning ahead is key. I think a lot of people think that they can plan their spring break trip in December. And I'm like, no, you should have planned it in March or April the year prior. So I think especially if you're traveling with a family during a peak time, like the holidays or spring break or summer, the further in advance you can plan that, the better, the more availability that you're gonna have access to.

And then as far as educators go and others in this space, I think the biggest challenge is differentiating yourself and finding a niche or an angle that someone isn't already covering. I don't think we were talking about this last night. I don't think it's enough to just be like, Hey, I'm so-and-so and I cover points and miles. It needs to be like, you cover for who, like who is your ideal audience and where are you traveling and what class are you, you know, are you focusing on economy for families to Europe? Are you focusing on luxury travel for family? You know, it's, you got to really niche it down these days, I feel like to get some attention.

Devon: I could not have the three of you on today's podcast and not actually ask you about things specific to earning and using points and miles, your best tips, your best tricks. Jess, you mentioned this trend that you're noticing of the more tools that make award travel available to people, you know, a little bit tougher. It's becoming to snag certain awards. Curious to hear from you all, what other trends have you noticed recently that are shaping the way that people earn and use points and miles?

Jess: I think more people, more women in particular, are open to business cards, which I think is huge. If you are traveling with a family, those business cards are really going, you know, you need, if you're traveling with six people, you need more points than if you're traveling with two. And so you need to, like business cards are a huge part of our strategy. I assume they're a huge part of your strategy as well. And I think people are learning like, okay, it's easier to qualify for business cards than I thought.

And if I don't have something that qualifies for a business now, I'm going to create something that qualifies for a business because those points are that valuable that I'm going to make it happen.

Devon: Are there any other trends, tips that you all have for folks in award travel?

Pam: Well, I think one of the things as far as tips is flexibility. I mean, we talk about not finding redemptions, that they're harder sometimes. But because I'm so flexible, because I'm retired, I can always find something. It isn't a problem with me, and it's that flexibility that makes it possible.

So I think, you know, you need to be flexible either where you go, the timing you go, what kind of seats you're willing to travel on. If you're not flexible, you are going to run into some problems. But if you're flexible, you know, you can still find it.

Alex: I just think a big thing is, you know, we get a lot of families who think, I can't do this because I have a big family, you know, and we laugh about this sometimes, we were just talking about it this morning. People think it's not going to work for them if they have either, you know, two, it can go both ways.

Like I have a family of six, they see me do something like, oh, I only have a family of two, like, can I do this? It's like, yeah, you just need half as many points as I need, or on the flip side, you know, I have a family of six. Let's say it's Jess going with her husband and her daughter, it's the three of them. Well, how do I do what you did with a family of three?

It's like, well, you just double it. You can take anybody's trip and make it work for the number of people in your family. And I think people get very overwhelmed by that idea or they think they can't do it because they don't see the exact same person doing it, you know, for representing their family. And so I think like Jess talks about making a recipe.

Jess: Yeah, So I have this analogy I use, okay, so Devon, you have a family of four, right? So say you open a cookbook and you're like, okay, I really wanna make this for dinner, but it says it only serves two. So like, I guess I'm not gonna make it for my family. Like, no, you wouldn't say that. You would just say, okay, I'm gonna double the ingredients and I'm gonna make this recipe for my family of four.

It's the same thing with points and miles. I think people get so bogged down in every single thing being representative of them that they can't see, okay, I can do this. I just need to fly out of this airport instead of this airport, or I can do this, I just might need two rooms instead of one room, but I'll just rack up more points to get that second room. And so it's totally doable, no matter how many people you have, it's just like the more people you have, the more points you're going to need. Probably the more further in advance, you're going to want to book your travel or you're going to want to be really flexible, like Pam said, but it's totally doable.

Like we both have families of six that we're regularly traveling with and have been for almost 10 years now. 

Alex: Yeah. It's like, Jess has a trip coming up to Hawaii. Well, by the time this airs, she'll be home from her trip. But they're taking all six of them are going. And so she booked two rooms.

We get a lot of people saying like, "Oh, how do I do this though? Like I have a family of six. How do I stay at the Grand Hyatt Kauai?" You just book two rooms, and then you're good. So yeah, you'll have earned more points, or you're like me, and you're like, "Okay, well, we're going to invite grandma, and we're going to put two kids in her room on the reservation, and so we only have to book one room." You know, you just have to, it goes back to being flexible.

It goes back to just, you know, making this work for you and not, not getting bogged down in the details of I have to do it this exact certain way. It's like, no, you just make it work how it works for you. We're teaching you and same with Devon, it's like we're teaching you the concepts, the ideas, and then you take that information and make it work for you and your lifestyle. You don't have to copy exactly what we're doing. This is just to give you some inspiration and ideas.

Devon: Yes, that is such a great reminder that nobody's journey has to look identical to anybody else's and you can still have points and miles work amazingly for you. Ladies, I'm so grateful for you sharing your time with us here today. Before we wrap up, I just have one final question I'd love to hear from all of you and that is just if there's one piece of advice that you would give to someone, whether they're just starting their own award travel journey or they've been in this hobby for a little while, what would it be?

Alex: I would say you don't have to know all of the things. That was my issue. I thought I had to know all of the things. And it's like, no, just start. Get a credit card. Start earning on that one credit card.

Learn how that one reward program works, and then you can go from there. You don't need to know Amex, Chase, Capital One, Citi. Just learn Chase Ultimate Rewards, and then call it a day. And then when you're feeling comfortable, move on.

Jess: Yeah, I totally agree. Like just do it. You're gonna have imposter syndrome. You're gonna feel like you don't know what you're doing. That's completely normal.

We have all been there and like, just get started. Take that first trip. It doesn't have to be a trip around the world your first time. You can just go like say, I'm in Texas. I could have just gone to like Florida for a beach vacation with my family and flown Southwest and stay at a Hyatt.

Like just start small if that's what you feel more comfortable with. Get your feet wet. Do a few domestic, easier bookings. And then try and go bigger.

Pam: And I would say my biggest piece of advice is you do you. We say this all the time. You do you. Don't do us. There is no perfect way to do this.

There isn't a perfect redemption. You do what works for you. And you know, that's the perfect thing. Just do what works for you.

Devon: Pam, Jess, Alex, thank you so much. That's incredible advice. Again, I appreciate your time today so much. For folks who are looking to learn more about you, about what you do, where can they find you online?

Jess: You can find us on Instagram @TravelMomSquad. And then we also have a podcast, Points Talk with the Travel Mom Squad. We have a blog, like we said, with I think over 600 blog posts on it. So that's just travelmomsquad.com. And you can find our blog there. And I think those are our three.

We have a Facebook group also if you want to join that with 80,000 other Travel Mom Squad members. So that's another place where there's a lot of support and feedback offered there from other people in our community.

Devon: All right, everybody, we will have the links to all of those resources for you in the episode description and the episode show notes. Travel Mom Squad, like I said, one of the most inspirational and influential groups of women in the travel award space. Thank you so much for spending time with me, especially on your vacation. I really appreciate it. And have a fantastic week, everybody.

Jess: Thank you so, so much.

Thank you for joining me for this week's episode of Point Me to First Class. If you want more tips on turning your expenses into travel, visit pointmetofirstclass.com to learn more. See you next week.