“I visited over 20 countries and worked as a bartender, english teacher, and bought and sold stuff on eBay.”

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Welcome to the next interview in our interview series where renowned mile and point gurus share their insights on having Big Travel with Small Money!

Miles & Points Interview:  Award Booking Service

Bobby runs Award Booking Service and has earned over 3 million miles and points, so I was looking forward to our Friday chat!

Award Booking Service – Interview with Bobby

Bobby in Key West, FL

How and when did you start collecting miles and points?

I earned my first miles from flying to Europe and back for a study abroad course in college.  That got me hooked on international travel and I began taking trips as often as I could and banking a few miles along the way.  Then I got a miles earning credit card and worked my way up.

I quickly learned the value of miles and points and dove right in!

Why did you start your blog?  What’s special about it?

I started AwardBookingService to help others use their miles and points to take amazing trips for very little money out of pocket.  I saw the opportunity to leverage my knowledge of multiple airline programs to earn a little extra money to fund more travels.  I now help people book their awards on a daily basis!

Airlines’ frequent flyer programs have complex rules and subpar websites.  This makes redeeming miles for the average person quite difficult.  I help make sure people are getting the most out of what they have.

What’s the one single thing people can do to get more miles?

Use mileage earning credit cards with large sign up bonuses and focus on bonus categories that matches their everyday spending habits.  For most this is gas, grocery, and restaurant spending.  Find a card that works best for your travel needs and boost your earnings!

What’s your most memorable travel experience?

Award Booking Service – Interview with Bobby

Lazy Beach, Cambodia Sunset 2011

In 2006-2007 I took an 18 month around the world journey.  I spent the entire time outside of the United States.  I visited over 20 countries and worked as a bartender, english teacher, and bought and sold stuff on eBay.

I learned more about myself, other cultures, and the world than any classroom could have taught me.  I intend to do at least 1 more trip like this if not more!

What do your family and friends think of your miles & points hobby?

Most of my family and friends are amazed at the trips that I take each year.  They are even more surprised by how little it cost me.  I am sure a majority of them think I am a little crazy for some the things I do to earn extra miles and points: buy and sell things, reloadable prepaid cards, constant credit card sign ups, and so on.

Is there any tool or trick which you’ve found especially useful in this hobby?

Since most of my travel is covered by award tickets using miles and points I find Expert Flyer to be invaluable to me.  This paired with in depth knowledge of all of the major frequent flyer programs allows me to stretch my miles and points to the maximum value.

What was the least expected way you’ve earned miles or points?

I once earned 5,000 miles for a hair loss exam at age 23–with a full head of hair.  I also did a life insurance consultation for 25,000 miles that I did not need in college.  I also visited 11 Delta SkyClubs in one day when they were handing out paper coupons for American Express Membership Rewards points!

What do you now know about collecting miles and points which you wish you knew when you started out?

I really wish I knew about all the major transferable points: American Express Membership Rewards, Chase Ultimate Rewards, and Starwood Preferred Guest points from the beginning.  They offer the greatest flexibility and are more shielded from devaluation than miles and points tied to one specific airline or hotel.

These are now the focus of my spending points earning. I encourage anyone else to do the same.

What would your readers be surprised to know about you?

I am 30 years old and have visited over 40 countries since age 20.  I have earned and redeemed over 3 million miles and points for trips all over the world in the past 3 years.  I also have a long term goal of permanently moving and residing in southeast Asia–my favorite region of the world.

Any parting words?

Award Booking Service – Interview with Bobby

Tikal, Guatemala

Always remember that when you are looking to redeem your miles and points:

1) Be very flexible with your travel dates

2) Plan as far in advance as possible (a year is ideal)

3) Be prepared to fly on non-direct flights

4) Miles and points are designed to fill seats and hotel rooms that would otherwise go empty–they won’t always be available on your ideal dates or flight routings.

5) Travel during low season makes using miles and points much easier.

Bobby – Thanks for sharing your thoughts on having Big Travel with Small Money!

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14 responses to ““I visited over 20 countries and worked as a bartender, english teacher, and bought and sold stuff on eBay.”

  1. D – I love you man, but maybe this segment has jumped the shark. Talking about other blogs is one thing, but doing an advertising piece on a site that is purely a commercial venture is a bit much. Just my 2 cents

  2. How can one visit 11 skyclubs in one day?

  3. Good points about award travel redemption. # 2 – planning a year out is good but sometimes F and J seats come up at the last minute because of cancellations.

  4. Emily, No visit to Tampa is complete without a visit to Bern’s Steakhouse. Darius will earn lots of miles and points eating there. The winelist is awesome. They offer multiple ‘good’ wines by the ounce.

  5. Traveling around the world while buying and selling on eBay? How’d you manage that? Hah.

  6. I’ve enjoyed Bobby’s posts on The Mr. Pickles blog, so it was cool to read this interview and learn more about him.

    This part resonated with me: “I also have a long term goal of permanently moving and residing in southeast Asia–my favorite region of the world.” I once spent five months backpacking around that region, lots of fun. Once you’ve enjoyed that combination of high quality of life and low cost of living, it’s hard to go back to anything else.

  7. Amol (@PointsToPointB)

    @James — I disagree… Many of the bloggers already featured have Award Booking Services as well, and many blogs are commercial ventures in and of themselves.

    @Bill H — ATL has 9 clubs and JFK has 4. You could potentially visit 13 Sky Clubs when flying that route.

  8. @ dhammer- Thanks, it sounds delicious! We’ll have to check it out the next time we are in Tampa.

  9. @ Bill H: I was on a mileage run and visited all the clubs in ATL and 2 in DTW. I maximize where I can!

    @Rom: I didn’t do a ton of eBay but I did have family help me. I would have items shipped home and then they would mail them for me when they sold. I gave them a small cut for their troubles.

  10. Pingback: Check out my interview with MillionMileSecrets! | Award Booking Service

  11. How can Key West be the southernmost point of the continental United States? It’s an island!

  12. What did you sell on ebay that funded your 18 months out of work vacation? Quite awesome…wish I can take 18 months off without the need to pay bills and put food on the table…

  13. @ Joe: It has a road connected to the mainland and is therefore considered the southernmost point as it has a direct ground link. That is my understanding at least.

    @ NYC Guy: I would buy and resell things that were way underpriced on eBay. Mostly electronics. It was not my sole method of funding my trip but I made an extra couple thousand dollars to keep me on the road longer. I also stopped in a couple of places for a few months and worked too. A great experience!

  14. BEST ‘least expected ways you earned miles’ EVER! Hilarious.