The World’s Most Outrageous ‘Travel Hacker’… Evil, or Evil Genius?

Lucky at One Mile at a Time writes about Justin Ross Lee today, a character in frequent flyer circles who much amuses me.

Lucky likes ‘JRL’,

I know Justin Ross Lee pretty well, and while the “act” is no doubt pretty extreme, he’s actually a nice guy underneath it all. He genuinely gets enjoyment out of making people laugh & smile…

I’ll concede that I’ve met him only once, at the first Frequent Traveler University event New York at the Sheraton LaGuardia in April 2011. So I don’t know him well enough to understand the man, I can only judge his public persona.

I think he’s a smart guy who never grew up and who turned that into a persona for himself that isn’t who I would want to be. He’s a train wreck reality star without the television gig.

The occasion for the post is a really funny video showing JRL buying refundable tickets to use the American Airlines Flagship Lounge at New York JFK as his office, declaring a starter pistol from Target as a firearm in his checked luggage, and printing business cards for companies he doesn’t work for to get their hotel corporate rates.

I think he’s a character, sort of the class clown who never grew up but spent a lot of hours on frequent flyer forums learning the tricks and he just doesn’t have the ‘filter’ most of us have — he has the nerve to push each ‘scheme’ to the extreme and desperately wants attention.

So far, so good — I think it would be a terrible thing if everyone was like him, which I suppose is an indictment from a Kantian standpoint. But he gets away with it and it’s his schtick.

That said I don’t think he’s at all the guy he portrays himself to be and I don’t think he’s as successful at his ‘travel hacking’ either. He gets first class award tickets — that’s not a feat worthy of the gossip pages. His business is ‘haberdashery’ but his line of pocket squares doesn’t actually make many sales.

A shameless New York self-promoter and velvet-rope gadfly — who snootily brags about copping freebies while flying only first class and sporting custom-made clothes — is flat broke, according to court papers.

In bankruptcy documents filed in Manhattan last month, social hustler Justin Ross Lee, who regularly boasts about his luxe lifestyle to his 5,000 Facebook fans, claimed that his aptly named “Pretentious Pockets’’ silk-pocket-square business is a dismal failure, raking in just $12,250 to date.

And that’s left Lee with a measly $100 in the bank, nearly $160,000 in debt and unable to cover the rent on his $2,700-a-month apartment in Murray Hill’s white-glove Anthem building, court documents say.

..The preppy party boy — who crows that he never buys “off-the-rack clothing’’ and struts around town in custom monogrammed shirts, custom-made suits and Hermes belts — was cut off by Barneys New York for a nearly $5,000 credit-card bill he couldn’t pay, documents show.

He owes more than $700 to his swanky Manhattan gym, Club H Fitness, too.

Citibank, to whom Lee also owes $80,000 in credit-card bills, recently sued him for breach of contract, according to the filing.

Financial troubles notwithstanding, he managed a spot on Millionaire Matchmaker — and wound up set up with a porn star who apparently lied about her age.

In the video Justin says, “If 49% of the people love you and 51% of the people hate you, you’re doing something right.”

Do you love him or hate him?

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. This reminds me of that blog post by the Dutch girl who faked a trip to Thailand on social media…it’s all about perception. Of you follow his posts, you’d think he was a successful entrepreneur who jetsets in style…clearly not the case

  2. LOL Millionaire Matchmaker. Most are Millionaire wannabes. Some dont have a regular job and little money. Many years ago a guy who worked for me always bought from Nieman Marcus. When he left we would get at least a few calls per year from debt collectors looking for him. That continued for years 🙂

  3. I am trying to figure out why anyone would spend 2 seconds thinking about an utter failure.

  4. I was about to say Who gives an F? And then remembered where I am posting this. So instead I will say Who gives a flying F… see what I did there

  5. um, um, um, I just don’t know how to feel now. But I do like the peanut trick!

    shake yo’a$$!

  6. Very interesting. That bankruptcy filing was from August 2011, but that YouTube video is recent. When I watched it, a super majority of those newspaper articles are of his face superimposed on the actual person. The most obvious is with the Cathay Pacific cabin crew—that is not him, his face was pasted on top of the actual person.

    The video is hilarious, though. Especially with the chick showing her boobs in 1st Class, where’s the uncut edition?

  7. Count me in as a fan of the video. He is to “normal people” what churners and MS’ers are to butt-in-seat flyers.

  8. This is the post of the day that you should remove. Please STOP giving this guy publicity.

  9. This guy is the modern day Jerry Rubin. The Who said “We won’t get fooled again”, but I guess Justin is of a different age, appealing to a way younger clientele.

  10. In answer to your question – I neither love or hate him. I simply ignore him as unworthy of my emotions.

  11. The part where he prints business cards in different companies’ names is outright fraud. I’m surprised these companies don’t care enough to go after him. Or the hotels he’s swindling.

  12. I am with “toomanybooks” above, I really don’t want to waste anytime or emotion in ‘love or hate’, just to forget this person.

  13. @Keith

    The Cathay Pacific cabin crew with JRL is a superimposed picture. It is someone else. Look closer. In fact, in the video, that same picture is close enough to see a mismatched neckline. Simple Photoshop technique.

    I still think that video is pretty funny, though. He should try to vouch Kevin Trudeau out of the slammer too.

    AA might get pretty PO’d if they find their aircraft and lounge as part of his promotion. He blurred the AA on the craft, but he forgot the tail.

  14. He might be a nice guy away from a camera but the problem is that his persona hangs over him. I can’t see any hotel believing that he actually works for one of these companies, his FQT-profile will be noted for sure. So if someone with such a high profile checks into your hotel and claims he works for Raytheon, yet has nothing to do but bullshit around for 4 days… I don’t know. Are these hotels to scared to go after him because they fear bashing in the media? As for the companies, that’s another story. If he indeed falsly claims he works for Raytheon ‘Missile Defense Systems’ that would be a sensitive issue. Maybe sensitive enough to revoke his Global Entry that he is bragging about. The year old bankruptcy case… not a big deal in my eyes. In America companies shed themselves of liabilities all the time, heck every major airline did that.

  15. @AS with IBM it may not be fraud, it sounds like he may have joined their free partner program (he mentions what he does with them)

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