One of the questions I’m asked most often in person is how I got started with my insane hobby, which has turned into a full time obsession. I never posted about it, but this seems like a good time to provide some background.
My parents are both from Germany and my dad worked for a German bank in New York for years. I made my first trip to Germany when I was just a few months old to see relatives, so I’ve always loved traveling. When I was about five I decided I wanted to be a pilot, and did all kinds of planning about how I’d be so damn awesome. At the time I decided that when I became captain I would start upgrading people until there were no empty seats left up front because it would build goodwill. I hadn’t realized non-revs would do that part of my job for me. 
Anyway, I was lucky to get to fly once a year in paid business class to Frankfurt on Lufthansa on the company’s dime when I was young. I remember being in the Senator Lounge at JFK with my dad, back in the day when being Senator was truly special. When we entered the lounge they’d take our boarding passes (they knew my dad) and would say “let’s see if we can find you a better seat,” typically resulting in an upgrade to first class. Anyway, eventually that ended, but I still loved airplanes, travel, and more than anything else, Lufthansa!
Another hobby I acquired as I was growing up was beating the system. I remember when an electronics store had a promotion whereby they would buy Play Station games for $10 a piece, regardless of the title. While I didn’t even have a Play Station (what can I say, I was never much into video games), I noticed that the electronics store was selling some games for around $6. I would buy ten games, pay $60, and get back $100. That was an easy way to triple my allowance at the time!
Fast forward to about six years ago or so when I needed to go with my mom to Germany in the summer to visit relatives. My mom had 100,000 Delta miles, but there was no availability for a coach award, which would have cost 50,000 miles. I decided to get creative and looked on Ebay. Hmmm, 100,000 Delta miles for around $1,000! That was basically the same as a coach fare, and for those 100,000 miles I could get a first class award on Air France. And that’s exactly what happened. My mom and I flew together on two Air France first class award tickets to Frankfurt. Of course in retrospect I realize buying miles on Ebay is a big no-no, but at the time it hadn’t occurred to me.
Suffice it to say that I enjoyed Air France first class a bit more than the airline I had been flying before, which was Condor (Lufthansa’s low cost carrier) nonstop from Tampa to Frankfurt, back when they still flew that route. I thought to myself “hmmm, how could I earn miles at such a good rate for myself, and maybe get other benefits out of it as well?” Given that I loved flying, I loved premium cabins, and I loved travel, I decided to do some investigating. One day I stumbled upon FlyerTalk.com, and just a few weeks later I got an offer in the mail from United. While I didn’t really have any airline affiliation at the time (in terms of miles), United was always my favorite US airline. Why? Because they had such close ties to Lufthansa, and Lufthansa was the airline I had such fond memories flying in first and business class growing up. Besides, as a German, I thought of it as “my” airline.
So in United I got an offer entitled “The Great Offer.” Sounds grand, doesn’t it? Well, it was targeted, and as it turned out I received the best version of the offer. They were basically offering 5,000 bonus redeemable miles and elite qualifying miles for every segment flown, up to ten. There were two catches — the ticket had to be in a minimum of a “V” fare class, and only segments beyond the number of segments flown last year counted. That worked out particularly well for me, given that I flew ZERO segments on United the year before. In other words, for 10 segments I would get 50,000 bonus elite qualifying miles and 50,000 bonus redeemable miles. How the hell could I turn down such an offer?
Two mileage runs later, which cost me a grand total of $700, I was sitting on over 60,000 elite qualifying miles and well over 60,000 redeemable miles. Talk about an easy way to Premier Executive! Anyway, at the time I was 14, so I did a few more mileage runs that year, and BAM, I was 1K. It was kind of fun being a 1K without even being old enough to sit in an exit row.
I figured 1K would be a once-in-a-lifetime thing, given that 100,000 miles sounded like a LOT. I had only flown about 50,000 miles that year, and I was exhausted. Then came the next year, when I was certain I wouldn’t requalify. Then came the fall and United offered a double elite qualifying miles promotion. It was like a box of chocolates where you promise yourself you’ll eat just one, but you end up eating the whole box. Well yeah, I requalified in no time. Year after year I flew more and more, although I kept telling myself it was the last year.
As I continued this “game” I got better and better at it. Every year I learned new tricks, and every year I got better deals. While my parents were skeptical about the whole thing at first, they are since advocates for mileage running. I can’t even count how many international first and business class trips we’ve been able to take to amazing destinations thanks to my hobby. I’ve seen places I’d never thought I’d see and have been able to do it all in the relative comfort of premium cabins.
And that’s my story. I’ll probably end the year having flown close to 300,000 butt-in-seat miles and I’ve gotta say, I’ve had a blast racking up and redeeming those miles!
Anyway, if anyone is so inclined, feel free to share what got you started with flying/traveling/mileage-whoring. It’s always interesting to step back for a moment and think about what got us started.
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