The flight that cost me 100,000 miles…

As I mentioned a couple of days ago I’m in Barcelona at the moment, and flew here “the long way.” My journey from Tampa to Barcelona routed me via Chicago, Las Vegas, Los Angeles, Miami, and New York. As usual, the flight between Las Vegas and Los Angeles was an interesting one, though taught me two important lessons:

a) Don’t judge a book by it’s cover
b) Don’t make a bet with someone that looks clueless

Let me explain. I boarded my flight from Las Vegas to Los Angeles, and as usual the crowd was an absolute disaster. As I Tweeted about, the lady sitting next to me was easily over 50, though wearing fishnet stockings and “stripper boots.” Sadly she was one of the more “normal” people in the cabin. The last two rows of first-class were taken up by an Australia family. One of the six kids was wearing a tiara and sash that read” BIRTHDAY PRINCESS” (I’m embarrassed to admit I’ve seen enough episodes of “Toddlers and Tiaras” to know those two terms).

As boarding finished up the lady seated next to me said “do you smell fertilizer?” I quickly responded with “sorry, it’s probably me, I’ve been flying for 24 hours.” Not amused, she pushed the call button and called over the flight attendant. “I smell fertilizer, I think someone boarded with it, could you look into this?” He also quickly responded with “all I smell is an MD-80.” I was laughing my rear off, though my seatmate obviously wasn’t.

Then we started talking about travel, and she started telling me about some great hotels. I still figured she was pretty clueless for whatever reason, and eventually, she stated a fact about a hotel, so I said “oh wow, I had no clue about that.” She sensed my doubt, so responded with “you wanna make a bet?” and I said “what do you have in mind?” She said “let’s bet 100,000 miles.” I asked her miles in which program, and she said “it’s your choice.” We settled on American Express points. As soon as we passed through 10,000 feet I turned on my laptop ready to collect my 100,000 Membership Rewards points, only to find out that she was in fact right.

So yes, friends, I lost 100,000 points on a travel-related bet. I think that’s the end of the road for me. I’ve lost my edge.

But the bigger surprise was that she was actually one of the most interesting people I’ve sat next to. She was the CEO of one of the most unique companies I’ve heard of, and she flies just about as much as I do (though actually pays for first and business class with cash).

So as much as it annoys me when people assume I don’t belong in first or business class because of my age or how I dress (what beef do people have with pajamas again?), subconsciously I find I still do the same thing to others. Time to force myself to stop doing that, and time for me to make the painful points transfer to her account…

Filed Under: American, Travel
  1. Was she blond and works in construction? I think I have seen a story about her on TV. Based on the vague description you gave, I bet it is her. I don’t recall her name though.

  2. I bet my 8th grade social studies teacher 50 points of my final semester aggregate, over the derivation of coconut milk. I’m surprised that he took the bet, but it was very satisfying to end up with a 130% average or something like that. 🙂

  3. You guys are like Romney’s $10k bet. Most of us are like “WTF, 100k miles, that’s a crazy high amount!!!”

    Something tells me though that she’ll appreciate your honoring the bet, and you’ll get some business out of it. At the very least, losing the miles will ensure the lesson learned sticks.

  4. A few years back, I bet Cactus-King Doug Parker an Envoy upgrade that CLT-HNL would last <6 months. He bet me he could ground the flight I tried to use the upgrade on if he lost the bet.

    Lesson learned: CEO's always win bets.


  5. Hi Ben, Very happy to hear that you are honoring the bet, but you are stand up guy so not surprised at all. Hope you enjoy Barcelona. What’s going on with Brownell? If you are accepting new clients please let me know.

  6. You basically lost 100k MR points going from LAS-LAX, the same as going to europe in J, but there no YQ. Haha

    What was the fact you lost on?

  7. Rule of Thumb: People who talk about how much money they have or dress as if they have money probably don’t.

  8. Like others, I’m curious about the details of the bet. But I’m also wondering why you decided to preface your trip to Barcelona by flying back and forth across the country.

  9. I think more shocking to me is that you watched “Toddlers and Tiaras”…I saw clips from the Soup and was horrified by the parents.

  10. My hero let me down today :)… j/k!

    So will we have a heroine joining this blog as a guest contributor? Am sure she will have equally interesting stuff to share about… or a different perspective since she pays cash for all the nice stuff you experience in your premium travels!

  11. I love PJs when flying! I ALWAYS fly in my scrub bottoms (I’ma nurse) and a tshirt! way more comfy then jeans or anything else! Off to the Philippines tonight in KE biz class in m scrubs!

  12. Hm. She might have looked clueless, but when she responded “pick a program” for the 100k bet, I might have backed down. Why?

    1. She has a 100k miles. Although that doesn’t sound like much to us, it is to the uninitiated.

    2. She has 100k miles in multiple programs. Figure at least three, because if it was only 2, she would have listed them as choices.

  13. @worldtraveller2

    That is who I think it was as well. I couldn’t remember her name though.

    @Dan – well put!

  14. I first read about Lynn Tilton a few years ago in Forbes, I think.

    Given that Ben once wore a ‘Glen’s Gotta Go’ T-shirt, maybe he has a thing for Tilton’s….

  15. You may not believe it now but this is one of the best lessons you will ever get. Nobody can believe they aren’t the best at what they do or that anybody knows more in their chosen field until they get bit and bit hard.

    Knowing you are good, great even, but not the greatest, or perfect is the key to being the best. You know you are good, but always careful to realize the possibility the possibility you are wrong. This is the difference that separates a young Bill Gates or Steven Jobs from the older one. Its absolutely critical to lifelong success.

    Savor this lesson. It will serve you well.

    And thank your lucky stars you got it cheap. Not too cheap because then it loses its meaning. But cheap enough you can say, phew I dodged that bullet.

    Just image if she had offered you 200,000 or even 500,000 miles, you were a bit greedy and decided to take the bet knowing you were right.

    That really would have smarted.

  16. Ya never know who you’ll meet on a flight.

    I once had a seatmate strike up a conversation about airline operations, the age of the NW DC-9 we were on, etc. After I had a few responses to his comments, he stated “you know a lot about this stuff, where do you work ?”
    When I told him, he said “oh, you must be steve64” (I had already given my 1st name).

    My jaw dropped as I’m just a nobody (well … other than at the time being the Lead Programmer on the Sabre/AA Flight Planning System .. but that was a Lead over a grand total of 4 folks). He was a contract Project Manager for my previous VP and stayed in touch with the VP even tho he never made the transfer to Flight Ops himself.

  17. At this juncture is it safe to assume that Ben’s not going to give us the full story? If yes, Ben would you please let us know as I keep checking back to hear more. Thanks. 🙂

  18. Oh wow!!! That wasn’t what I was expecting to read at all. We would like to know though, what the hotel fact was that you bet 100k points on. I mean surely it must have been good!

  19. @ Despina — Fine, fine, fine, I give in. 😀

    Yes, I’m rather embarrassed. The bet was over the Hotel Arts in Barcelona. She thought it was a Ritz Carlton property, and I didn’t think so. That was the basis of the bet, and I lost… and even more than the miles, I lost my pride. 😀

  20. @Lucky, didn’t mean to badger you into revealing anything, but I was checking back constantly and just wanted to know if you had moved on and so should I 🙂

  21. @ Despina — Whoops, sorry. Shared some details in post 39, though what else would interest you? It wasn’t Lynn Tilton, and I don’t think she’s high profile enough for me to mention her name here.

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