CHAPTER 1: How it All Started

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I’m not an expert, nor a maven. I don’t claim some special knowledge on this issue – I learned it all from travelers much savvier and better-travelled than I. But they taught me well, and this is the story of how I first soaked up their knowledge.

I don’t remember how exactly I first came across the points blog-world – probably late at night, unable to sleep, wasting time on Google. But once I discovered it I was hooked.

Since I was a kid, I had been a sophisticated traveler. I was fortunate to travel a ton. I was on four continents before my 13th birthday, and had even sat up front a few times. I was always obsessed with airplanes – the bigger the better – despite my absolute certainty that I would one day die in a plane crash (more on that later). Over the years I had developed a basic understanding of airlines and reward programs and was a member of just about each and every one. But while I had been able to accumulate mighty sums of points, I was always left with the feeling that I wasn’t maximizing value to its fullest.

I wasn’t.

I was a graduate student, living off of government loans. My loyalty program memberships saved me hundreds if not thousands of dollars, to be sure, but I was redeeming points for less than a penny a piece, throwing them at opportunities to save a few hundred dollars here or there on domestic travel. And despite traveling tens of thousands of miles each year, I was still vexed by the lore of airline status, unable to ever focus more than a few trips on a single airline. I was an economy traveler, and I didn’t want to be one any longer.

So, it was in December of 2011, that I started reading the few blogs I’d come across – OMAAT, Points Guy, a few others – and was hooked immediately by the dream of aspirational travel, the dream of big seats taking me to far away places with free flowing alcohol and all at a cost of almost nothing. Here were guys my age who had found ways to hack the system and go around the world in style all for, more or less, free. There’s a whole universe, hiding in plane sight, where people spend hours a day discussing the best programs, the best airlines, the best systems to be gamed. Who knew? Big planes, big seats, caviar and alcohol and delicious food. It all seemed too good to be true. But it wasn’t. It was possible, and I’d found roadmaps from other travelers to show me the way.

I immediately began taking steps that would set me up to rack in hundreds of thousands of points, but knew that that process would take time, and patience is not a virtue the Lord blessed me with. So I decided to tackle the other pillar of this travel-hack world – status – immediately.

Early January 2012, before the resumption of classes, I travelled to Amsterdam to visit friends for the weekend on a super cheap ticket, nonstop from LAX on KLM. Upon my return, I was 15,000 miles closer to status with Delta.

Why wait for my next travel needs? I thought. Let’s speed this up!

Air ticket prices were collapsing, and I came across a roundtrip fare from LA to New York for only $149. I ditched classes the next day and spent 12 hours flying coast to coast and back, turning my seat into a mobile office where I pounded out my rabbinic thesis at 40,000 feet.

The sheer absurdity of the whole exercise was what made it so exciting. Want to go to New York for 2 hours? Why not? And now I was one step closer to my sought-after status. Sure, it cost me a few hundred dollars, not to mention the many hours sitting in coach, but this was fantastic. I was still in the air somewhere over the country’s heartland when I bought a second ticket to go from LAX to Kansas City to Atlanta and back to LA in one day for $120. This would put me over the top to Gold.

I was now an elite traveller. Whatever that means.

But my status was on Delta, and I suddenly needed to be in Washington DC three weeks in a row for job interviews, and the best nonstop flights from LA to DC were on United. Damn.

The story could have ended there, but I was determined to put the status that I had worked so hard to achieve to use. So, before booking the three trips, I got United to match my Delta status – most airlines will match competitors’ status, with limited frequency, to steal your business. It was super easy, and just took an email. I had status now with two airlines. Not to be outdone, and to maximize the possibility that my newfound status would actually earn me something in the form of free upgrades to the front of the cabin, I booked my trips back and forth on a 777 with an international configuration flying the domestic route.

For three weeks that spring, I flew back and forth and back and forth and back and forth again between Los Angeles and DC, in what should have been the most stressful, exhausting period of my life. But I did it in style. And with such a large business class cabin as was found on the 777, my upgrades cleared each and every time. On a cross-country trip I was able to enjoy a flat bed – my first in the air! – and free alcohol, and a sundae bar, to boot.

They call this work?

I was hooked.

This was hardly the most aspirational achievement. Status made travel infinitely more comfortable, and, I was proud of the “accomplishment”, but my long game was all about something of a different sort entirely. I was proud of what I’d accomplished, but I still had work to do.

That would require collecting points, a ton of them, which to do in an achievable time frame – remember, I’m impatient – would require strategy.

Big league.

More on that to come.

Next, on #PointedOut: collecting the currency, quickly, without destroying my financial future.