Rolling Stone is an icon of pop culture and a barometer of hipness in American life. Not surprisingly, a recent issue has self-proclaimed diva Kim Kardashian letting it all hang out on the cover. Flip past that though, for an incredible article centering on Ben Schlappig, author of One Mile at a Time.
It’s a marathon-read — written in that typically Rolling Stone style — but well worth your time. What this article provides is not just a look at Ben, but a look into our world of miles and points and a remarkably clairvoyant overview of what drives many of us to play the game of miles and points.
I’ve known Ben for a decade and herald him as the superlative inspiration of my own pursuit of miles and points. We used to mileage run on United and nine years ago — I was 19 and he was 16 — it was already quite apparent that he was going to do something very remarkable. In total honesty, that was my assessment then, not just me looking back in hindsight now. And everyone who knew him then will tell you the same thing.
I met him for the first time in United’s Terminal 7 Red Carpet Club at LAX. We were both headed to Washington on UA946, the 777-200 flight United used to run each morning to IAD. He was the 15-year-old with the club card and flying in business class. Thanks to him and others on Flyertalk, I soon gained club access and began to consistently fly in premium cabins too.
He spearheaded frequent flyer events, in-flight “Dos” and built the groundwork for the immense following he enjoys today by being the guy who made things happen and the one who really went all-in to the sports of mileage running and luxury air travel, evidenced by his infamous Flyertalk thread entitled, Six Transpacs in Five Days. HELP ME!
There was a glitch on united.com that allowed routing from Osaka to Seoul via San Francisco for only 20K miles each way in first class, meaning four transpacific first class flights ran only 40K miles.
When asked why he would subject himself to such a thing, Ben responded:
Well, that is a good question which I have asked myself all day. At the end of the day, I am only down about 10K miles (or less), and a little over $1K. Actually, it may even be cheaper, since I have absolutely no expenses. When it comes down to it, I am a minor, and usually like to travel with my family. I am actually going to ICN in June anyway, so I will have a chance to “preview” the airport. This is just a nice way to enjoy the F suite, and to have an out of the ordinary experience. Like I said, this is something which I will remember for a long time, and must be close to setting a record.
I guess the eccentricy of it just intrigues me…
Not your every-day attitude, but I love it and if you look at his initial post it is filled with questions — Ben was not always the expert, but became an expert through relentless dedication and corralling the expertise of others to build up an arguably unparalleled knowledge database of his own, which he imparts to others through his blog. This is a classical hallmark of a successful businessman.
#AvGeeks at a United event at Chicago O’Hare with Captain Denny Flanagan
Back in the quieter days of Ben’s blog, when he was still flying United, Ben had this stalker named Josh that used to comment in every single post that he wrote and even followed him on a mileage run we took together — Ben wrote about the mileage run here (with a special post just for Josh) and I wrote about it here. The guy sat across the aisle from us, eyes transfixed on Ben the entire flight from San Francisco to Seattle and then on to Washington Dulles. Can you say awkward?
And yet does it offer a bit of perspective, perhaps, on why Rolling Stone eventually wrote about him? There is a certain ironic gravitas around the self-effacing, yet scrupulously exacting persona of Ben. He does sort of just draw people in — it’s a gift. And as his career grows exponentially each year, I’m incredibly proud of him and what he has built.
The RS story ends on a bit of a sad, note:
“I want what I can’t have. There’s nothing gratifying about that. It’s crazy, and it’s f—– up. I’d still like to think I’m a reasonably happy person.”
But I think everyone who knows him will attest that Ben can have what he wants and what he has taught me beyond the tricks of the trade is to be a more joyfully generous person.
We happened to be in Paris in the same weekend in the summer of 2011 and met up for lunch. Ben paid the tab before I even knew what was happening. We were at a Flyertalk event in South San Francisco on another occasion at a restaurant where everything was charged to one bill and attendees were supposed to contribute cash to Ben, the event organizer. When the dust settled, though, there was a ~$400 deficit. Only a few of us were left and Ben waived off our money, putting the entire amount on his credit card. This was before the blog — Ben’s only income was in the form of United vouchers and this had to hurt. But through the years, over and over again, he is always the one who lunges for the check, the one who orders drinks for 100 people at Frequent Traveler University on his own dime, and the one who will always get back to you, no matter how busy he is.
This is the real Ben, an unbelievably generous person with his time, money, and efforts — look no further than his gracious replies to the jealous bile spewed by so many in the comments section of his blog.
A Real Housewives .gif in honor of Ben
The RS reporter grilled me for four hours for the story and I did not even get a mention in the story beyond this lovely blurb on my role at FTU–
A disheveled former White House staffer leads a seminar titled simply “Hacking United.”
He spent more than a hundred hours with Ben and still managed to fudge the headline — we all know that travel is not free. But I love the article overall and while Ben’s life is not for everyone — living out of a suitcase and flying 400K miles per year is not even for me — you cannot help but to marvel at the niche empire he has built and wonder where is he off to next.
Me with Ben at the 2015 Freddies in Atlanta