December 13, 2014

How I Got Started - Part One

A few readers have asked that I provide a bit of background on how I got started with this hobby.  It's a bit lengthy so I broke it up into two parts.  Here's part one:

It all started in college.  I didn’t realize it at the time but I was about to embark on a life long obsession with traveling for free (okay for cheap).  I did what typical college juniors do.  I flew home a few times a year, I visited friends at other campuses, and I studied somewhere else (Washington D.C.) and I took a random trip to New York to see my college roommate Dana on "Who Wants to Be a Millionaire?”  Dana would get the third question wrong (although he would later return to show without me and win $64,000) because we were out late the night before partying but the frequent flyer miles I racked up during the year made me a newly minted United (what is now Premier Silver) frequent flyer for flying 25,000 miles in a calendar year.  It was 2003 and that was my first taste of elite status.

The next year, I graduated from college and worked on a political campaign.  I mailed in a copy of my college transcript proving that I graduated (unfortunately the program has been discontinued) and United gave me 10,000 MileagePlus miles.  Seriously.  Emily (now my wife) was still in school at Lehigh University.  One fall weekend, we met in Philly for a weekend and I had to ask my parents to borrow some SPG points to pay for the hotel and they were kind enough to help out.  The next year, I moved to Washington, D.C. and started a job at the Corporate Executive Board and picked up my first Starwood American Express.  I worked with a guy who had previously sold Westin timeshares and he told me this was the best credit card I could get.

In 2006, I was promoted and started a job as a traveling outside salesman.  I spent over $100,000 on my corporate credit card in one year.  I stayed nearly 100 nights in hotels.  I met Emily in Europe while she was studying abroad and we had a wonderful long weekend at the Westin Paris courtesy of all those SPG points.  I flew over 100,000 miles and made United 1K in 2007 for the first time and gifted “Premier Associate” status to my 21 year old girlfriend.  Upgrades were easier back then and I flew first class most of the time at 25.

Emily and I moved to Denver in 2007 and I started a new job in 2008 at PaySimple with little business travel.  We used up the remaining SPG points and United miles to go to Vancouver, Mexico, Las Vegas, New York, and Washington, D.C.  I applied for the occasional credit card.  But looking back on it, I was a novice.

We bought our first house a few years ago and I had a stash of over 100,000 American Express Membership Rewards.  We needed things like light bulbs, screwdrivers, and hand towels.  So I redeemed those MR points for gift cards to Bed Bath & Beyond and Home Depot.  In doing so I received $.01 per point.  Oops.  I could have used those MR points for a one-way ticket to Asia in Singapore Suites.  Double Oops.

Why didn't someone tell me that they have ice cream on the upper deck??

It wasn’t until we were planning our honeymoon that I started to read travel blogs consistently.  It started with The Points Guy, then One Mile at a Time, then the entire suite of Boarding Area blogs became daily reads.  We debated on where to go.  Somewhere warm?  Somewhere new?  Somewhere exotic?  We finally decided on Southeast Asia and found decently priced tickets to Hong Kong.  I figured out how to upgrade them to business class using miles (terrible use of miles BTW) and somehow figured out how to book our hotels and a few intra Asia business class flights using points and miles.  Our luxurious honeymoon was not going to cost very much and my new wife seemed to really be pleased.  Maybe I’m not a novice?

Honeymoon in Hong Kong

I had read about mileage runs but never been on one.  In hindsight, it really made no sense for me to start mileage running without status.  But it seemed like a fun thing to do and I’ve always found flying fun.  So I booked a very cheap fare with 4 segments and headed to the airport early one Saturday morning for a day of nothing but flying.  It was 2012 and 2012 United and Continental were completing their merger.  What better day for my first mileage run than that day?  Needless to say the day was a mess.  I flew almost 4,000 miles in one day and since I had no status, I earned 4,000 miles.  But my first mileage run was complete and I was hooked.

Later in the year, I flew on another handful of mileage runs.  I was flying a lot of business and was inching closer and closer to 1K status on United.  I even convinced Emily to join me on the final mileage run of the year.  We flew from Denver to LA to Houston to Baltimore where we spent the night (on points) in an airport hotel.  The following day, we flew back to Denver via Houston and I was 1K for the second time in my life!  Earning 1K status meant upgrades north of 75% of the time for the next 16 months.  We used our GPU/RPU (United upgrade instruments) to fly business class to Hawaii, Mexico and London.

So what to do with all those points and miles?  Until our honeymoon, we had not been on a long haul flight together.  We had been to Alaska, Hawaii, Mexico, and Costa Rica.  But for whatever reason, we traveled a lot domestically and our international trips were closer to home.  We both wanted to see more of the world and see a lot of it before kids...

Come back tomorrow for part two!

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