Frequent Miler on the Air - Frequent Miler origin story - Stephen's story | Coffee Break Ep63 | 7-15-25

Episode Date: July 15, 2025

We’ve been gradually telling the “origin stories” of each team member in Frequent mIler. Today, we’ll talk about how Stephen came to join Frequent Miler.Frequent Miler origin story - Stephen's story(01:04) - When did Stephen first get into the points and miles travel hobby?(04:41) - Stephen remembers the stackable IHG promo codes(05:39) - Stephen's wife helped him pull the trigger on some early credit cards like the US Airways credit card with a bonus after just one purchase(07:54) - Stephen recalls his earliest credit cards (which he has noted in a spreadsheet, of course!) (09:35) - In 2016, Stephen and his wife decided that (in two years), they would start a roadtrip to every state in the US. They prepared by piling up on hotel credit cards.(11:30) - When did Stephen get into gift card reselling? (14:29) - How did Stephen get involved with Frequent Miler?(15:36) - Stephen remembers being excited that Frequent Miler had linked to his website! He was also very active in the Frequent Miler Insiders Facebook group.(16:51) - Stephen remembers being invited to write for Frequent Miler to help cover Nick's paternity leave. He wasn't sure it would cooperate with the roadtrip he was about to begin, but his wife helped encourage him to go for it! (A Frequent Miler author theme).(18:23) - Nick talks about how he came to recommend Stephen as his paternity leave coverage. Stephen's useful posts in the Frequent Miler Insiders group made him the first person Nick thought of.  (19:62) - How did Stephen become the "king of stacking"?(22:21) - Stephen talks about how his time at Frequent Miler has been.Visit https://frequentmiler.com/subscribe to get updated on in-depth points and miles content like this, and don’t forget to like and follow us on social media.Music Credit – Beach Walk by Unicorn Heads

This is a VoyEscape podcast. You can find all of our travel podcasts from around the world at voyescape.com. Welcome to Frequent Milers Coffee Break, where we focus on a single topic related to miles and points. And each coffee break is limited to 20 minutes or less, or your money back. On today's coffee break, we're going to be interviewing Stephen Pepper to learn his origin story. Stephen's been working with us for a number of years now as one of our primary authors. And we want to dig into how he got started, how he got started with Points and Miles

and how he discovered FrequentMiler and what ultimately led to him joining our team. Welcome, Stephen. Thank you. It's good to be here finally. I'm excited to hear more of this because I feel like I know, I feel like I know you pretty well, but I don't actually know how you really got started.

I know about your first ever points redemption because we wrote a post about that at some point, but I don't really know how you get started in points and miles and in the broader sense. So I'm curious to hear more about it. Cool. Glad to share. All right, Stephen, let's just dig in. Let's start from the beginning.

When did you first start thinking about points and miles with respect to travel? So going back, I guess it's 20 years now or something like that. This was back when we were still living in the UK at the time. I wasn't really into Point of Miles too much. I had been collecting IHG points just because we had stayed at Holiday Inn at one point and so that ended up kind of like becoming our default loyalty band of choice when we needed to stay somewhere.

But there wasn't kind of too much involvement in the Points and Miles game, although back then I was much more into grocery store points. So over here, like Tesco and Sainsbury's were two of the biggest ones. And Tesco, their club card loyalty program, you could redeem the points. Nowadays, you can actually transfer them to, I think it's both Avios and Virgin Atlantic, but back then I don't think that was possible, but you could redeem them for certificates for things like Thomson Holidays or Thomas Cook Holidays where you could book package vacations using your grocery store points and stuff. And so our first kind of proper redemption of those was my wife and I went on a week long all-inclusive trip

to Lanzarote, which was fantastic. So even though it wasn't strictly points and miles, it was kind of points and miles adjacent with that. At the time, because my wife's American, we used to fly back and forth to the US a couple of times a year. And usually that was on Virgin Atlantic. And so we joined Virgin Atlantic Flying Club. And so we pick up some miles here and there, but not a substantial

number. But then our first redemption came when we moved from the UK to the US. Because we only needed a one way flight, but one way flights in cash are super expensive when you're trying to do that from London to the US. US to London, it doesn't tend to be too bad. It's like just kind of regular price. But if you try doing it in reverse, then they charge like a thousand pounds or something like something crazy like that. But we were able to do a points in cash rate where we only redeemed, I want to say like 3000 or 5000 points at the time. And then we just had to pay like one or 200 pounds copay in order to get a one-way flight over to the US to move over there. So that ended up being a pretty fantastic redemption considering I didn't have a clue what I was doing back then.

And then after that, I think it was like six months later, we got a Virgin Atlantic credit card, because they had a special setup at the time where if you're an expat, then they would be more likely to grant you a US-based Virgin Atlantic credit card even if you didn't really have any credit history in the US. So that was handy getting into that. So we started collecting more miles with them, ended up getting a Delta Sky Miles card, just because I can't even remember where I heard about that. And then I started reading online a little bit more about points and miles. I think I had been looking at stuff on Flyer Talk. And so that was back when IHG would do all those fantastic promotions where it would be like stay two nights, you get this many number of points, stay at two different

van, you get this many number of points, and you would have all these challenges. And then you would get like 50,000 or 100,000 points if you completed three or four of them or something like that. And so I got really into that because we had lived in Thailand for a little while. I also had some work trips back to the UK where I managed to end up completing some of these challenges. So I started getting really into points and miles at that point. Yeah, before you say more about that, I remember those promos where they- Accelerate, right?

That's the same goal, yes. Accelerating, yeah. So I'm wondering, was that your first with doing that sort of thing? Or even before that, it used to be that on Flyer Talk and other sites, they would post like promo codes with IHG if I remember right, where, you know, it'd be like, codes with IHG, if I remember right, where, you know, it'd be like, stay once, get

this many points, stay twice, get this many and they would all stack, like you could load them all to your account and then like a couple nights could generate like 40,000 points or more or whatever. Yeah, that's what I did. Yeah, I was getting the codes off of Flyer Talks. So I wasn't kind of active in the Flyer Talk scene, but I was a lurker and I was taking advantage of all those codes that you could enter on your account. So that was, I guess, my first kind of proper gaming of anything like that.

Yeah. You know who I learned that from was Drew, Kerry's husband, who used to have the blog Travel is Free. But yeah, I can't remember if I learned it from in person or from reading his blog. But yeah. And so after that, I think I had started reading The Points Guy for a while. And then that was back when USA Airways was still around. And it was coming towards the end, like American Airlines had announced that they were taking them over and that the USA Airways credit card

was gonna be coming to an end. And it was when you would get, I think it was 50,000 miles for one purchase or something like that and paying the annual fee. And so I was intrigued by that, just because it seemed like a super easy way to pick up all these miles. But I hadn't pulled the trigger,

but then my wife got on a work trip to Denver. And then she got back and she was like, just FYI, I might have applied for a credit card. And she thought I was going to be like really annoyed. And I just said, so it was like this flight on USA ways. They said that you could get 50,000 miles just for one purchase. And so it seemed like it was worth it. I was like, sweet, okay, you've already got ahead and done that. Let me do it for myself before it's too late. And then, yeah, things just kind of snowballed from there. And so, um, found out about Freak-O-Miler, Doctor of Credit and stuff like that. And, um, yeah, just really got much deeper involved in, um, earning

and redeeming points and miles. That's fantastic. I remember those, uh, the U S airways dividend card. I had a couple of those when, when that got converted over. So I remember those the US Airways dividend card. I had a couple of those when when that got converted over. So I remember hopping on that too. It's funny because I think I must have gotten started not too long behind you. Probably you were starting a little bit before me. But I remember those IHG Accelerate promotions and going after those two right near the beginning

of my journey with miles and points too. So it had to have been in the same years anyway, I would guess maybe 2010 to 2015 somewhere in that window. Yeah, I think it was like 2014, 15 or something like that. Yeah, kind of when I really started getting deeper into it. That's funny that we both kind of got deeper into it around the same time. So all right, so you started getting deeper into it, Started then doing some more redemptions where you collect. I mean, started with the US Airways dividend cards. Did you get into transferable points like how how quickly did it snowball

and in which way initially? Because I feel like what I know of you, you've done a lot of road tripping, but I haven't heard about a lot of flights to far-flung places. But maybe I just haven't heard. I don't heard about a lot of flights to far-flung places, but maybe I just haven't heard. I don't know. How did you end up kind of broadening your horizons with us? So I just brought up my spreadsheet just because I'm trying to remind myself of what cards I ended up getting. So the ink plus card was one of the earliest ones I ended up getting. And so that was before 524 came along. And I'm really glad that I picked that up

back in the day because that was also meant that you get $50,000 worth of spending at 5x rather than only 25,000 that you get on the in cash. So I was pleased to have gotten that at the time. What was the welcome bonus back then? Oh, that was... 70,000 ultimate rewards for 5,000 spend in three months. So it actually wasn't all that bad. Yeah, even by today's standards, that's not bad. Yeah.

And so it looks like my next cards were the IHG Select card, which was 80,000 points on a thousand dollars spend. I got the Premier Rewards Gold MX card, which is now just the regular Amex Gold card. That was only 50,000 membership rewards at the time, whereas we it's basically double that now. So yeah, back then, I feel like 50,000 was a pretty good offer on the gold card. So I'm yeah, so I was just basically going after whatever cards had decent welcome offers at the time. I knew about things like

not being able to get an MX bonus more than one, so I was trying to save myself for getting higher bonuses when I wanted. Because at the time we were doing some traveling, but we weren't doing a whole ton of traveling, and so it made more sense just to kind of pick and choose and maximize our earnings that way. But in terms of trips, at that point we were living in the US, but we, so we would go back to the UK every year or every other year. We've done, we had done like a few international trips

and things like that. But yeah, that was before our big road trip. So as soon as we decided on doing our road trip. So we decided in 2016 to do a seven year 50 state road trip. We knew that we weren't going to set off until January 1st, 2018, though. So we spent kind of like the next year and a half just collecting as many hotel points as we could get, getting pretty much every single hotel credit card that made sense, and just started like saving up as

many points as we could. And so by the time we left, we had, I think it was about two million, two and a half million hotel points. And that includes ultimate rewards. It doesn't include membership rewards, but it meant that we had like a good stash in all of the big hotel currencies. So that way we could cherry pick Redemption, which made it much cheaper to live in hotels and Airbnb's. So as an aside, you mentioned Ultimate Rewards, presumably because you would transfer those to Hyatt. But did you ever... were you already at the point where you realized that was the best way to use Ultimate Rewards? Or did you ever consider transferring them to Hyatt? Yeah, no, I think I knew even... I think one of the main reasons I had gotten the ink plus card before was because I knew that it would be some good redemption for hired and so I'd gotten that one.

Back in those days as well. That was when you could still get on SPG cards and SPG was still a thing because it was just before I ended up destroying that. And so I remember us having some great redemptions at 2000 points at some Sheraton's and things like that when those were available. So that was fantastic at the time. Very nice. Very nice. So were you doing any, I mean, I know you eventually ended up with a very popular gift card site for gift card deals. Were you earning your welcome bonuses and points by buying gift cards and selling them even in those days

or just using ordinary spend? How did you go about the process of earning the two and a half million points or whatever it was that you had for hotels? So a fair bit of that was from the sign up bonus welcome offers. Some of it was through spend. I was doing a reasonable amount of

gift card reselling at the time. That was before the sites that I sell to now, but that was back in the days of the plastic merchant, which rest in peace or I guess don't rest in peace. But in case you're not familiar with the plastic merchant, it was a gift card reselling company that went under and left a lot of people holding the bag. So we ended up losing about $1,000 on that, which in the grand scheme of things, really wasn't bad at all. Some people ended up losing like five or six figures on that, which would have been like far more painful. But yeah, I was doing a fair bit of gift card reselling. And I've come across that through, I think it was Fat Wallet, which was a website forum back in the day that had a really decent finance section on there.

So I found out about buying gift cards using Amex offers. That's how I first started getting into that. It would be like a $100 or loads of Amex offer where you spend $100, you get $20 back or something like that. And so I'd go in and buy a Lowe's gift card or buy a gift card from their gift card rack, and then we sell it. And that was back in the day where it was like super easy to add Amex offers to all of your different cards. And so you would be able to get this offer on like pretty much every Amex card that you had. And so you could end up making like a decent amount of money on every single one if you had some good Amex offers. So that was kind of what got me into the gift card side of things way back when. All right. So go ahead Greg. Well, I was going to say, so you said initially that

you didn't have many membership rewards cards. So when you're talking about Amex, I guess you're talking about Hilton cards and SPG at the time. Yeah, so, um, Marriott cards. So I think I've had like a platinum card for quite a while, but some Amex cards I just never got. I never ended up getting the Amex everyday card. Just because I was trying to prioritize the cards that made the most sense. So you can only have five credit

cards. But in terms of charge cards, yeah, I've had like, Amex Gold card, like, numerous business gold cards and business platinum cards and stuff over the years from all the different offers and no lifetime language offers and things like that. So yeah, I've managed to win a decent stash of membership rewards over the years too. But yeah, so in terms of the credit card side of things, our focus was more on the hotel kind of thing so that we could earn as many free nights certificates and points as possible. Right.

So how did you go from doing that and building that up? I think I know the answer to this, but I'm sure other people want to know and maybe we'll see who remembers what here. How did you end up starting with all of that, planning out your road trip, but then also, I mean, you mentioned that your road trip started in January of 2018, and that is about when you started with Frequent Mylar, if I remember correctly.

So how did that come to pass? So at the time, so we had started our own blog, No Home, just trying to cover our road trip in 2017. So we started that about nine months before we set off on the road trip, because we wanted to cover the planning and all the preparation that would go into it, including things like getting rid of all of our stuff,

because we ended up minimalizing hardly having anything by the end of it. And so I'd been writing that and then I got to the Chicago seminars in 2017, and I'd met both of you there. And I'd gotten chatting to Nick. And then I was super excited one day when I was just reading through like my feed. I feel like back then it might've been the old Google read or something like that rather than Feedly, but he linked to my website because I'd written a post about a couple of AARP redemptions that you could get to save money on travel.

And he had linked to that in his like, we can review like round the web posts. And I was like, oh my word, I've just been linked to by Freakamaila. I've made it in life. And so that was just fantastic. And at the time, I was like fairly active in the frequent Mylar Facebook group. I think you'd only set that up like six months beforehand or something. So it's fairly new. And but I'd like shed some deals in there. Because that was back when staples would do 100% rebate offers for things like batteries and other stuff like that. So you could

order them online, get them delivered for free, you could earn cash back through a shopping portal. And then you'd earn all these points back that you can redeem at Staples and like earn 5x on the transaction and things like that. So I posted like a few things about how to maximize those kind of deals. And I think it was ink cartridge recycling, where you would buy them in bulk on eBay, like these empty cartridges, and then you could recycle them at staples and get all this like money back and stuff like that. And it seemed to be off the back that

my wife and I took a month long trip to Australia and New Zealand at the end of 2017, just before our road trip started. And it was while we're in New Zealand that I got an email from, I can't remember if it was from Nick or Greg, where I'm just asking if I would like to write part-time or full-time or whatever on frequent miler, because Nick was about to be going on paternity leave. And so I was like, oh man, okay. So I was like chatting with my wife and I was like this is an amazing opportunity but I just don't know if I should say yes because pretty much as soon as we would we got back to the US we were going to

be setting off on our road trip and I had no idea what our new life was gonna look like and so I didn't really want to commit to riding for Fregal Myla, just in case I couldn't end up doing it justice and if it kind of like took away from our road trip that we were planning. And then I think she effectively said, like, don't be dumb, like, do this. We can make it work. Like, you love Freak with Myla, like this would be like a dream kind of opportunity. So just do it and we'll just make it work. And so in hindsight, I'm so glad that she had said that

because yeah, like I took them up on the offer and have been with Freakamaila since, I think it was the first or second week of 2018. So yeah, a week or two after we started on the road trip, I started writing for Freakamaila and it's been amazing. It's so, and I should say, we're really happy too that she said that to you. But it's funny because Nick and Tim also had stories about their wives convincing them

to apply. But now kind of backing up to where we got to that point, because yeah, I was going out on paternity leave and so Greg and I had had conversations about that and he said we're gonna have to find somebody to cover the quick deals while I was out and he asked if I had any suggestions any recommendations and Stephen was the first person that came to mind because you had been posting so much stuff so many different stacking deals in our frequent mylar insider's group like you said it was pretty new I think maybe six or eight months, but you had consistently been posting deals to stack and I don't remember actually the staples free after rebate once at all. I do remember

that you had posted a deal for stacking on a laptop on an HP laptop from HP with an Amex offer and a shopping portal and I don't remember the details of it, but I remember that I bought a laptop because of you and it was a great deal. And it reminded me of one of the questions from the application when I applied, because Greg had asked something about like, how would you stack to get a great deal on a laptop at Best Buy or something along those lines

when I had applied was on the application. And I was like, oh, well, here, this guy just passed the test, he gave me such a good deal that I bought it. I, this is the best laptop I'm using now. So, and I think if I remember correctly, and my memory does fade a little bit as I get older, but I remember that being in November, and I had probably met you at Chicago seminars in October.

So like, this was just a perfect storm of things. I remember being very impressed with your stacking skills and I thought that's exactly what you need. If you're in right quick deals, meet somebody who looks at things and you've, how did you develop that? The whole like love of stacking. Cause I feel like you're kind of the king of stacking, which at the time I felt like I had claimed to that type of title. But, but, but then you just had all these great stacks. How did you get into it? Cause you've also written our posts about how to stack card linked offers between different programs and whatnot. How did you get into that? Because you've also written our posts about how to stack card linked offers

between different programs and whatnot. How did you get into all the stacking? Yeah, like going back 20 years back in my kind of like original origin story. But we had some shopping portals back in the UK. And so they used to be like opportunities to earn things there that were never really an opportunity in the US. So I guess it's not really stacking as such, but back then if you got contents insurance,

which I think is what you guys call vendors insurance, then through certain companies, then you could get say like a hundred pounds cash back through the shopping portal. And the policies were only like 50 or 60 pounds. And so you could get your vendors insurance for a year, included that we wanted anyway, and make a profit off it. And so we just like switched providers every single year. I'm picking up like all this cash back and like profit and stuff like that. And so I'd always been interested in shopping portals

back then. And so yeah, like getting to the US then having like things like Amex offers and other card linked offers. And I feel like the HP deal. Yeah, it was like an Amex offer. It was a shopping portal. I think you could buy the gift cards. I feel like there may have been like HP award points that you would earn through the portal when you were deemed to the gift cards or something like that. And so yeah, that's exactly what it was. Yeah. Opportunities like that. Yeah. Yeah. And I think there were there were Amex offers, right, as well. So like you'd buy the you'd buy the gift card through the portal, save, you know, get money back from Amex, get portal rewards, and then you use it and get even more rewards. Yeah. And that's exactly what it was. That's why I bought it, because I had, I hadn't been looking at an HP laptop,

but that's what it was. It was the double dip that it got me. I was like, oh, he's double dipping the gift cards and using the MX software, slicing and dicing. And I was very impressed. And not only with that, you had posted other stuff like that too. So I thought you had exactly what we kind of needed,

but we had no idea whether you would be interested in doing it. So I was excited when you were. So I know you're a little hesitant, maybe player to kind of convince you to do it. What did you think when you got started working for Frequel Mylar? Did you enjoy it? How did that first part go?

I mean, it was gone for a while. It was absolutely a relief that I had said yes in the end because I think I would have regretted things big time if I hadn't. And so, you know, it was fantastic straight from the off. So yeah, you were on paternity leave. So I was just covering some quick deals for Greg. At the time, I think I was just doing them like here

and there. So like I was writing part-time, but I would do a couple of hours one day, a couple of hours the next, and things like that, just helping to fill in for each day. But it was fantastic, just because I guess it's kind of a fairly autonomous job. Like Greg just kind of leaves us alone for the most part to write about these deals and any way we see fit and things like that.

He's not just like overseeing and micromanaging or anything like that. So it was really nice. I've been really fortunate over the years to have decent bosses. So for the last like 20, 25, 30 years or something like that, I've had like a really decent time with that. So yeah, I've been fortunate that Greg's been such a fantastic boss in this latest jobs. So it was really great when Nick was off on paternity leave and you started, but did it get bad once he came back from paternity leave? No, it was even better. It was just like really great to have that kind of interaction. And then like with Cavi kind of joining the team more. And then Tim as well. Yeah, you've managed to, I mean, well, I was going to say you put together a fantastic team. I guess that's kind of like blowing my own horn as well,

saying I'm part of that team. But like it is a fantastic group to, um, to be a part of. And yeah, it's just been awesome. Sure has. Uh, all right. Well, thank you so much, Steven. Um, I'm afraid we ran over the 20 minutes a little bit, I think. So, uh, you will have to pick up the tab on paying everyone back because of that

So, thanks again, thank you awesome Don't forget if you've enjoyed this and you'd like to get our email list You want to go to frequentmiler.com slash subscribe to join our email list follow us on all the various social media and check out our Frequent Mylar on the air episodes dropping every Friday. Hey, I'm DeAndre Koch, financial advisor, world traveler, and host of Revolutionizing Your Journey. If you're ready to unlock luxury without the luxury price tag, this show is for you. Each week, I sit down with experts to reveal

how to fly in $10,000 business and first class seats for 90% off and stay in five star resorts for nearly free using the power of points and miles. From insider tips to real traveler stories, you'll get the tools to travel smarter and see the world differently. Find revolutionizing your journey at voyascape.com.