The backstory: How Nick got into miles and points

Unlike many people who blog about airline miles and hotel points, I’ve never had a job (before this one) that included business travel. As a kid, my family vacations consisted of fun road trips to amusement parks within a few hours’ drive of home. Until my mid 20’s, I had only been on an airplane a couple of times. And yet somewhere between there and here, I’ve managed to see 59 countries (and a lot of far-off territories) and earn a living writing about how to travel more for less. We’ve written before about our first reward redemptions and I’ve explained why I travel with my kids, but I’m not sure I’ve ever shared how I specifically got into the world of award travel (or at least not in much detail). This story won’t help you earn more points or discover a hidden sweet spot or open Qsuites availability for your family of six to the Maldives, but after a recent reader email asking about how we got into this world, I figured it might be fun to pull back the curtain a bit and share some of my miles and points story.

My wife and I met through a mutual friend in the mid-aughts while she was finishing college. She spent a semester studying abroad in Australia and then when she graduated from college, we both had “real world” jobs that we didn’t enjoy for a couple of years. Even before graduation, she had expressed a desire to take a year off and travel sort of “backpacker style”; it just took us a while to realize that what we were doing wasn’t making either of us happy and to build up the courage to pack it in and throw caution to the wind.

We each took a course to get certified to teach English as a foreign language abroad. We didn’t know where we wanted to go, but in a stroke of luck there was someone in my course who was from Ecuador. Johanna strongly recommended that we try teaching in Ecuador because it was easy to get a job and cheap to travel there. She said she’d be happy to help us find a job and a place to stay. Truth be told, I didn’t even know where Ecuador was on a map (the equator, yes. Ecuador, no). I barely knew Johanna (the course was maybe 60 or 100 hours or something?), but she seemed genuine about her offer to help and we figured it might be wise to move abroad to a place where we had some sort of local connection, so we decided to give it a shot. As crazy (and full of youthful exuberance!) as it sounds, on the plane from Miami to Quito was the first moment it dawned on us that we really didn’t know Johanna at all. We had emailed with her several times, but hadn’t spoken on the phone to reconfirm pick up details. What would we do if she just didn’t show up at the airport? Did we know enough Spanish to find and get to a hotel? We were so, so underprepared.

Johanna was waiting at the airport when we walked out and she turned out to be a saint; she became one of our best friends and was a bridesmaid in our wedding almost a decade later! We spent almost nine months in Ecuador, teaching ridiculous hours during the week and then taking off every weekend to explore part of the country (often with Johanna). Buses were about $1 per hour — so a trip 8 hours away costed $8 each way. Meals were cheap. We were staying in hostels for $5 or $6 per person per night (sometimes less). As someone who had only been abroad once before that, it was eye-opening for me. We both quickly caught the travel bug and wanted to travel more.

Over the next five or six years, we worked hard, often 60 to 80 hours per week for 8 or 10 months, and then took off to travel for a month or two. We still didn’t know anything about miles or points, we just chased the cheapest airfare deals and Pricelined hotels (or also stayed in hostels and even did some Couchsurfing).

Having begun working online in 2009, we wanted to take advantage of our mobility. A friend from Vienna who we had met on top of a volcano in Ecuador recommended Berlin for its low cost of living (at least at the time) and youthful vibe. After finding a furnished apartment in Berlin for less than $400 a month, we spent months working online from the apartment Monday to Thursday and then bouncing around Europe on weekends on cheap Rynair flights, continuing to feed our travel addiction.

At some point, a friend of mine changed careers and went to medical school. He spent part of a semester in India, so we went to Asia and then met up with him to spend a few weeks traveling together in India. Again, we did those things working on a shoestring budget, often staying in very basic accommodations — sometimes too basic. I’ll always remember the straw-filled mattresses and unflushed toilet in a hot and dirty hostel room we stayed in one night…..and the downright luxury of the Holiday Inn we booked via Priceline the next night.

During the early part of the 2010’s, I started reselling merchandise. That began because there was a tablet I wanted called an HTC Flyer. I knew my wife (girlfriend back then) would think it was a waste of money (and she wouldn’t be wrong), but I saw it on sale so cheap that I thought that if I bought three of them, maybe I could sell 2 of them and make enough money to cover the cost of the one I wanted to keep. I did just that and she said, “Maybe you should buy ten more of those!”. I took her up on the suggestion, and when that went well, we began reselling more and more. At the time, we only had a Capital One Venture card, but we were earning our 2 “miles” per dollar spent. My wife’s sister really wanted to take a cruise for a milestone birthday and we were able to generate enough miles on the Venture card that the cruise didn’t cost us anything out of pocket, which felt awesome.

Then, in 2013 or so, we decided that we wanted to settle down and get married. We figured that we’d soon after have a family and live a “normal” life and we probably wouldn’t be able to travel much in the future, so we wanted to have one last hurrah before we got married and we wanted it to be big. We had heard of round-the-world airplane tickets (I’m talking cash tickets, still nothing with miles). While researching those tickets, I stumbled on stuff from The Points Guy and Million Mile Secrets. I started reading about credit cards and miles and I was intrigued. I had built up to reselling over $100K worth of stuff per year, so the prospect of meeting spending requirements seemed really easy. I wasn’t making a lot of money on resale items, but it was a small profit and a bunch of points. That led to the realization that maybe we could build this round-the-world trip with miles by piecing together awards. I dove in and spent every day for about a year just reading and learning, not applying for anything. In 2014, I started applying for credit cards.

Then I had a really fortuitous thing happen: that friend we traveled with in India and I had decided to run the 2014 Chicago marathon together. He knew I was getting into points and said he had a friend that I should meet who was kind of obsessed with miles. I met his friend Lance and we hit it off right away. Lance knew a lot more about miles and points than I did, but he said that his dad was really a master of the game, having been playing it since the 80’s. As fate would have it, that year the marathon and the Chicago Seminars (which I had never heard of at that point) were the same weekend, so Lance’s dad was in town and came to the after-marathon party. I got talking to him and he pulled out his iPad and started showing me notes from the Seminars and talking to me about things that were on another plane of existence beyond what I’d learned from reading TPG and Million Mile Secrets. Soon thereafter, Lance told me about an FTU (Frequent Traveler University) that was coming up in Washington DC in December 2014 and he recommended I go. I had been excited enough about some of the things his dad had explained that I convinced my wife that we should take a ride down to DC for an FTU.

At that FTU, none other than Greg, the Frequent Miler spoke about “extreme stacking” — using various shopping portal and gift card techniques to earn more miles. By that point, I had been doing resale for a few years and I thought I knew everything I needed to know about shopping portals and stacking. I attended Greg’s presentation in large part because I didn’t have much interest in whatever the other presentations were in that time slot.

That was lucky for me because Greg absolutely blew my mind. I had been going through a portal to make purchases, but I had known nothing about double dipping and triple dipping. At the time, it was often possible to click through a shopping portal to buy a merchant gift card and earn portal rewards and then click through the portal again to buy merchandise using the gift card and earn rewards again, essentially doubling your return on that purchase. In some cases, you would earn store rewards on your purchase and you could then click through a shopping portal and use your store rewards, earning rewards a third time. That mostly doesn’t work anymore. But back then, I went from earning let’s say 10x on a resale purchase to earning 20x or sometimes even 30x. To illustrate an example: I would click through a portal at 10x and buy a gift card for $1,000, earning 10,000 miles. Then I would click through the portal and use the gift card to buy $1,000 worth of resale merchandise, earning another 10,000 miles. At the time, Sears was notorious for selling items where you could get as much as 100% back in Sears Rewards, so sometimes I would use my $1,000 in gift cards and get both stuff and $1,000 back in Sears rewards. Then I’d click through the portal a third time to use the rewards and earn another 10,000 miles — ending up with 30,000 miles and $1,000 worth of stuff bought with the gift card and another $1,000 worth of stuff bought with the rewards, having only spent $1,000 total out of pocket. Even if I only resold that $2,000 worth of merchandise for $1,000, I was ending up with the $1,000 in cash that I had started with (losing nothing) and walking away with 30K “free” miles. In many cases, I was actually making a profit on the resale items. As a reseller, it was a huge game-changing boon.

One night soon after, I earned my first Southwest Companion Pass while sitting at the end of a hotel bed doing exactly what I just described: Sears was at 12x on the Rapid Rewards shopping portal, so I went through the portal and bought $4500 in gift cards (earning 54,000 Southwest Rapid Rewards points) and then immediately went through the portal and used the gift cards to buy $4500 worth of stuff to resell (earning another 54,000 Southwest Rapid Rewards points). I earned Sears rewards points on enough of those purchases to go through the portal again and earn the remaining 2,000 points I needed (at the time) to secure a Companion Pass to go along with the ~$1500 worth of Southwest points. Again, even if I ultimately resold the merchandise at a loss of 10 or 20%, it was still a terrific deal (I can’t remember what I bought now).

I began reading everything Frequent Miler published and going after tons of new cards and various offers and we almost immediately signed up for the next FTU in Las Vegas a few months later (where we met and introduced ourselves to Greg). We spent about a year from the time we started collecting cards in 2014 until our wedding in 2015 and earned enough points and miles for us to take a 4-month honeymoon around the world, flying mostly in business and first class and staying in hotels we never would have dreamed of before. I think we visited 18 countries on that trip and just couldn’t believe any of it. We leveraged a lot of tricks to reach destinations that in some cases we had never even heard of before planning the trip just because we could. We had never flown in a premium cabin before that trip and the whole thing was just wildly eye-opening.

When we got home, it was kind of like when we had moved to Ecuador back in the aughts, which is to say that we had the bug all over again and didn’t want it to stop. So we continued to dive in head first and collect more points, reselling larger and larger items and continuing to consume as much Frequent Miler as possible.

Then, at the beginning of January 2017, Greg posted that he was looking for a full-time employee. At that time, my wife and I had online jobs and we were comfortable. I had just barely gotten started on creating a blog of my own (I had only written four or five posts and I hadn’t even shared a link with family or friends yet, thinking that I wanted to build out a library of some content before going public with it). I saw Greg’s post advertising the job, but I wasn’t immediately confident that I could do it justice (Frequent Miler was something I valued very much!). I also hadn’t been thinking about changing careers. To some extent, I was content enough with life and I was afraid to take a risk.

However, my wife was also a dedicated Frequent Miler reader at that point. She saw Greg’s post advertising a full time position at Frequent Miler and asked me if I’d seen it. I said I had. She paused for a moment, waiting for me to go on. When I didn’t, she impatiently asked, “Well you’re going to apply, right?”. When I told her I wasn’t sure, she looked at me like I had three heads and said, “What do you mean you’re not sure? You have to apply for it.” She was convinced that I could do it and I would love it and that I should do it. As has often been the case in life, she was right.

Later that same month, we were on our way to South Africa. We had gone to Kruger National Park and Cape Town during our honeymoon and loved it so much that we booked another trip only about a year and a half later (at the end of January 2017). The moment we landed in Johannesburg, I got the email from Greg offering me the job (I still very much remember that Priority Pass lounge in Johannesburg and just sitting there in disbelief).

The rest, as they say, is history. I don’t think we could have anticipated where it would go, but the ride hasn’t stopped. Before Frequent Miler, I don’t think my wife nor I imagined that we would be able to continue traveling as much when we had a family, but we haven’t yet wanted to stop traveling and we have been fortunate to be able to continue to earn enough miles and points to support the trips we want to take. Neither of us traveled much growing up (I had only been on an airplane thrice before college….once with my grandmother for a trip to Puerto Rico when I was 8 or 9 years old; once for an international leadership conference I was chosen to attend (which is a story for another day as I trace my interest in travel to that event); and once as a finalist for a college scholarship when I was 17. My wife had a little bit more travel experience, having flown a few times to visit a family member in the military. Neither of us grew up in a world like this miles and points one we inhabit today, but it has been phenomenal to enjoy it and now to share it with our kids and with the people who read the site and listen to the podcast, etc.

Along the way, I’ve learned a lot. From award chart sweet spots to elite status quirks to the magic of a Greg Davis-Kean spreadsheet to the joy of working with and for truly good people, the job has been chock full of lessons. And that’s to say nothing of the freedom I’ve had to dive into what interests me or to work from wherever I may roam or to write a story about how I got into miles and points.

I often marvel at the chance of circumstance and the influence it can exert in a domino effect. Had we not quit our jobs and moved abroad, had we had a terrible experience in Ecuador, had we not reconnected with that friend in India, had he not introduced us to Lance, had the Chicago Marathon not been the same weekend as the Chicago Seminars, had Lance not sent me to FTU, etc — any one of a number of puzzle pieces cut out and I don’t know I’d be here doing this. When I say I feel lucky, it’s not a feigned deference to fate but rather a purely honest recognition that the convergence of my interest in travel with my stumbling on miles and points and being directed to an FTU all happening simultaneously was not the result of a skillful strategy but rather serendipitous. I didn’t come into this award travel world as a battle-tested road-warrior, but rather I came into this as someone who wanted to travel more than my means would allow. As I got a taste of that, my appetite for it grew until it became a full-time obsession job. The ability to turn my interest into a career has been nothing short of awesome. I love what I do and I look forward to continuing to do it for a long, long time.

That’s my story, and I’m sticking to it.

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