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This Week Marks 20 Years in Points and Miles!

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This week marks 20 years since I first redeemed frequent flyer miles — and look how far we’ve come. As a 12-year-old boy, if you had told me that I would have a career in points and miles, I probably would have laughed hysterically and said there was no way because I was going to be a lawyer. Oh, how times have changed!

Someone recently asked me on Facebook how I got started as The Points Guy, and it really dates back to 1996. Growing up, my dad was a healthcare consultant and traveled all the time. I was always really good with computers — when I was eight years old in 1991, I taught myself Microsoft DOSused dial-up Prodigy when computer modems would screech out loud and vividly remember connecting to the good old World Wide Web from a behemoth desktop computer. When my dad was hired by a start-up in California and worked from home, he didn’t really know how to use a computer because he’d had a secretary for his whole career up until that point. From there, I kind of became his administrative assistant and learned how to book his travel.

This kid would help his dad book work travel online.
This kid would help his dad book work travel online.

Back in those days, Travelocity was a new and unique concept. The site launched in 1996 and between booking my dad’s travel and my interest in the internet, I immediately became a member. In fact, I still have a Travelocity username that is just six letters long because I’m one of the original members of the site — talk about a throwback. As a result, I really became acquainted with booking his business trips, so much so that I began charging him $10 a trip to find him the cheapest flights, get him the best seat and make sure that he would have the best experience possible when traveling. That is where The Points Guy really began.

Over the years and with all the traveling at his new job, my dad accrued a ton of frequent flyer miles — a bunch on American Airlines and, at the time, a different airline that went by the name of US Airways (remember that?). One day, he proposed that the whole family go on vacation to Florida and I remember being a little bit of a precocious preteen saying, “Eh, Florida is king of boring and we’ve done it before. Why don’t we go to Grand Cayman?” I’d only heard about Grand Cayman because I’d just read “The Firm” by John Grisham and was obsessed with it — blue waters, a safe island in the British West Indies and high-flying international finance. It sounded amazing!

I loved every minute of family time at Grand Cayman with my family.
I loved every minute of family time in Grand Cayman.

At first, my dad thought I said the Grand Canyon not Grand Cayman, which also wouldn’t have been a bad trip, but he just wasn’t familiar with the Cayman Islands. For some reason my parents trusted me and I convinced them that we should make the trip. So I started planning — and it ended up being much cheaper than if we had gone to the Jersey Shore, which is what most families who lived outside of Philadelphia usually did. We ended up renting a house on VRBO called Maiden Plum Kai. My dad and my three siblings would fly nonstop on US Airways from Philadelphia to Grand Cayman while my mom and I would use my dad’s AA miles to make the trip. Back then, the two airlines, which are now one, weren’t even in the same alliance, as the first major airline alliance, Star Alliance, wasn’t founded until 1997. My mom and I would fly from Philly to Miami, have a layover for several hours where her friend Mike from high school (who was then the AA Latin American operations manager) took us around town in his convertible and showed us South Beach. I was pretty obsessed with the city at the time — who would have thought that 20 years later I’d be living there?! After our layover, we hopped on a plane from Miami to Grand Cayman. I vividly remember flying over Cuba and thinking how cool that was — I never thought that in my lifetime I’d be able to visit the beautiful country.

Our family's trips to Grand Cayman are some of my fondest memories.
Some of my fondest memories are of our family’s trips to Grand Cayman.

That being said, I also remember being mortified. What if the vacation that I planned went terribly wrong? What if the house was nothing like I’d imagined? We got off the plane – of course, there weren’t any cell phones back then — and I was still so nervous. We went through customs and my dad, whose flight had landed much earlier in the day, had a beaming smile on his face. I eagerly asked him “How is it?!” to which he replied that it was awesome. Success.

Our house, Maiden Plum Kai, was in the Rum Point area of Grand Cayman, and our next seven days on the island were incredible. We were right by the beach with picturesque crystal clear water that perfectly fit what I’d imagined in my head from “The Firm.” We visited Stingray City and spent a day on Seven Mile Beach, but we really spent most of our time snorkeling together and hanging out, playing cards and bonding as a family. Our week together at Maiden Plum Kai really made up for the fact that my dad was gone so much for work and it was great being able to spend seven amazing, quality-family-time days together.

Each trip to Cayman became a great family bonding experience.
Each trip to Cayman became a great family bonding experience.

After that amazing trip, vacationing in Grand Cayman became an annual tradition for the Kelly family. Every year when we would go to Grand Cayman, it was a bonding experience for all of us — we’ve gone back to Grand Cayman seven other times over the years and even took a trip to Barbados together. And then we tried Florida, but once you get a taste of the Caribbean, Amelia Island and Marco Island just aren’t the same. I even surprised my parents with a trip to Grand Cayman for their 60th birthdays — and the trip was just as incredible.

Poor Maiden Plum Kai!
Poor Maiden Plum Kai!

Last week, I was lucky enough to be in Grand Cayman for the Ritz-Carlton-sponsored Cayman Cookout, which was incredible (stay tuned for a full review coming soon!). As part of my time in Grand Cayman for this event, I wanted to take a trip down memory lane and find my beloved Maiden Plum Kai. I had heard that over the years the house was knocked out by Hurricane Ivan, but part of me was still wondering if they had rebuilt it. I ventured down the familiar roads and after a little bit of searching we found it and unfortunately, it’s still knocked down. The Driftwood Bar & Grill, which was an amazing beach dive bar that we used to go to right down the road from the house, has also been out of business since 2011. Part of me wants to open up a beachfront dive bar — stay tuned for that (ha ha)!

Maiden Plum Kai
The gorgeous view from my beloved Maiden Plum Kai.

It was cool to go back to where it all started and it actually hit me while I was there that it’s 20 years ago this week that the first points and miles trip took place. What made the trip even funnier is that I flew to Grand Cayman for the Cayman Cookout from Miami on the same leg that I did 20 years before — and this time I only used 4,500 Avios (don’t forget to make use of this fantastic redemption before they go away on February 2!), which is less that what I had used 20 years ago. Who says that better deals don’t come along? Granted, it’s comparing apples to oranges because I flew Miami to Grand Cayman and Avios awards are distance-based, but you get the drift that even 20 years later, I still got an amazing deal.

The original TPG home-page header in 2010 — look how far we've come (but we still love that boarding pass!)
The original TPG homepage header in 2010. Look how far we’ve come — but we still love that boarding pass!

So, that’s where my story in points and miles started, but I’m also often asked how TPG began. Fast-forward to 2004-2005 when I was Student Body President at the University of Pittsburgh. I started traveling a ton for that and all of a sudden, I had US Airways Gold status. I discovered FlyerTalk in 2004 and that’s when it hit me — there was a whole other world out there. I really immersed myself in the points and miles hobby from that point on, and in 2007, I got a job on Wall St. and started traveling nonstop. I was earning tons and tons of miles during the Great Recession when pay wasn’t going up, but I was a 20-something-year-old in Manhattan trying to get by so I started TPG in 2010 as a way to make some extra money. I would get paid for a favorite hobby of mine — booking award tickets for other people. I started blogging about it in June 2010, and by April 2011, Seth Kugel of the New York Times wrote about the site. At that point, advertisers started coming on board because a true community was built during that first year of readers. And then it happened — in 2011 I left my job and decided to become a full-time blogger and TPG as we know it was born.

Five years later, we’re still here and better than ever! Luckily for me, I installed Google Analytics from the first day, so I’ve had pretty solid tracking numbers of the site since it first started. I’m happy to report that our traffic growth has increased steadily for the past five years. Whereas when TPG first began in 2010, we had 9,887 unique visitors in December, and that number has increased every year since — 165,272 in December 2011; 295,035 in December 2012; 654,394 in December 2013; 1,200,154 in December 2014; and 2,516,447 in December 2015. Of course, I have you, my readers, to thank for that — TPG would not be anywhere close to where it is now without you. I’m more excited than ever for the future of TPG — with TPGtv launching on February 1, the charity work we’re going to be announcing soon and by continuing to share news, deals and tips on a daily basis. So, thank you all, and here’s to another 20 years of points-fueled travel!

(Whoops, we previously used the wrong data — updated now!)

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