How I got started mileage running…

I’m asked all the time how I got obsessed with the mileage game, especially since I started quite young. I’ve told the story dozens of times in person, though I don’t think I’ve ever posted about it, so here we go.

I’ve always been obsessed with airplanes. I remember being seven and having my mind set on being a commercial pilot. Beyond that, most of our family lives in Germany, so even as a kid I was constantly traveling back and forth between the US and Germany to visit family. So I’ve always been obsessed with airplanes. Beyond that, I’ve always enjoyed beating the system. I remember being about 12 and seeing an ad in the local newspaper for an electronics store that was willing to buy back any Play Station games for $10. I went to the store and noticed they sold games for $6. So what did I do? I bought ten games and sold it right back to them and made $40. That was about four weeks allowance at the time.

So I loved flying, travel, and beating the system. Could there be worse symptoms for someone about to become obsessed with the mileage game?

Maybe in 2003 or 2004, we were working on our travel plans to Germany for the summer, as we did every year. My dad had 100,000 Delta miles, and we intended to use those for travel to Germany for the summer. There was no coach award availability for anything below 100,000 miles, though Air France first class was available for that amount. Yes, back then you could still use Delta miles for Air France first class. And yes, Delta miles were still worthless on Delta metal awards back then.

While I realize in retrospect it wasn’t allowed, at the time we went to Ebay and noticed someone was selling 100,000 Delta miles for around $1,000, which was about the same as a revenue coach fare to Germany over summer. We almost instantly purchased the miles, and days later we had two seats booked to Germany in Air France first class. Suffice it to say, after the trip, I was addicted.

So being the “how do you screw the system” kind of guy I was, even in my early teens, I started doing some research. I read FlyerTalk.com, and started signing up for every mileage program. At the time it was all a bit confusing to me, so I didn’t actually start mileage running. But I remember reading posts by people who were doing mileage runs with envy.

The following spring, the perfect opportunity presented itself. I believe I was 14, and it was the year that I would make 1K. One day I got home from school and my dad had an offer in the mail addressed to me, entitled the “Great Offer.” I was a critical SOB back then, even, and figured it was some marketing gimmick, but it wasn’t. It was the most lucrative promotion from United I had ever seen, and likely ever would see.

The offer was simple. The promotion was targeted and there were several variations of the offer out there, but I lucked out with the most lucrative version. Untied was offering 5,000 bonus elite qualifying miles and 5,000 bonus redeemable miles for each segment flown within the timeframe of the promotion. You heard right, 5,000 bonus elite qualifying and redeemable miles per segment.

There were two catches. First of all, it was an “incremental” promotion, so the idea was that you only get those miles for each segment you fly more than you did during the same time period last year. So if you flew 30 segments last year in the second quarter, you would start earning the bonus with your 31st segment. Lucky for me, I had zero segments the year before, so I was earning it starting with my first flight. The other restriction was that the ticket needed to be booked in at least “V” class, which wasn’t too high of a fare class. The promotion was also limited to earning the bonus for ten segments.

So I was set. I wasn’t great at setting up mileage runs at the time, so I set up two runs, each the same routing. They were both Tampa to Chicago to San Francisco to Los Angeles to Washington Dulles to Tampa. They were $350 each, for a grand total of $700. For that I would earn over 60,000 elite qualifying miles and 60,000 redeemable miles.

And the runs were a blast. I was already an elite after my first run, and remember my second trip, where the second segment was to be from Chicago to San Francisco on a 747. My upgrade had cleared to the upper deck (yes, back then not everyone was a 1K), and I was so excited. The night before I noticed the aircraft was downgraded to a Ted A320 (yes, going from a three cabin, flagship product, to an all coach product), so I decided to call United. At the time the thought of bumping off the flight hadn’t even occurred to me. On the phone, because I was so nice, the agent said she had rebooked me on a flight an hour later, which was a three cabin 777. I expressed my disappointment in not getting the upper deck, since I was really looking forward to it. Because of my grave disappointment the agent had rebooked me in a first class suite on the next flight. Life was good!

And that’s how it all started. By the time I was 14 or 15 I was a 1K, and at the time, flying was great. Even though it was around the same time that most people thought United wouldn’t survive, the employees all seemed very united and gave 110%, for the most part.

I figured there was no way in hell I would requalify. 100,000 miles seemed like a ton. But the game is addicting. And profitable. And there were more promotions.

So every year I say I’ll fly less, but every year I fly more.

And that’s the story behind how I got started!