“Pick a Place, Then Figure Out How to Get There…for FREE!”

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Welcome to the next installment of our interview series where folks share their thoughts about Big Travel with Small Money!

Miles & Points Interview:   The Reward Boss 

Jeff started The Reward Boss to share award travel tricks and deals.

The Reward Boss - Interview With Jeff
Heading Directly Into a Storm in the Jungle of Peru (Puerto Maldonado)

How and when did you start collecting miles and points?

I started collecting about 6 years ago.  That’s when I was traveling for work and lived in hotels for 3 years straight.  I got rid of my apartment and car because I didn’t need or use them.

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

After figuring out ways to get free travel for myself, I was often helping others do the same.  Many colleagues would flock to 1 hotel or another to grab bonuses and other perks.

At 1 point, I had a team of about 20 colleagues who were all driving luxury Cadillac rentals to the client’s office.  All free upgrades I negotiated through Avis.

I started writing to share these tricks and deals with friends and colleagues.  My site is geared towards beginners and I often receive questions and help people figure out how to get their next trip for free.

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

For the typical beginner, finding the right credit card bonus is the fastest way to get more miles.

What’s your most memorable travel experience?

The trip I just returned from: Vietnam, Malaysia, Singapore, and finally Maldives.  It took a crazy amount of planning but I managed to book Business Class award flights for this trip.

Why Maldives?  I had a honeymoon to plan and a million Hilton points which were being devalued.  I thought what better time to find 1 of the most expensive hotels in 1 of the most difficult places to find award flights to.

I decided not to hotel hop and stay in each place longer, which is a big change.  I got to experience some amazing places, views, food, hotels, islands, and wildlife.

The Reward Boss - Interview With Jeff
Incredible Views at the Conrad Maldives

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

Friends love it and do the same.  My family usually teases about never staying put and asking which country I will be in the following month.  I have offered to help but they are not too interested.  I don’t understand why.

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

Staying organized with AwardWallet has helped keep up with all the different miles and award programs.

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

Using my Chase Ink card to buy something at Staples (on clearance) and getting 5X points and ~3% cash back through BeFrugal.com, and another 5% in rewards through Staples while working towards the sign-up bonus.

The Reward Boss - Interview With Jeff
Snake & Bird Wine in Hanoi, Vietnam

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

I used to think I would never accumulate enough miles and points to get anything, and that whatever I did collect would expire before I got to use them.  With a little bit of effort, the payoff is huge!

What would your readers be surprised to know about you?

I have traveled to many places around the world, but I am terrible at packing!  It’s often a mad scramble 1 to 2 hours before I have to leave my apartment.  Otherwise I may spend many more hours.  Checklists are very helpful!

The Reward Boss - Interview With Jeff
Low Tide at The Andaman Hotel, Langkawi, Malaysia

Any parting words?

Live to travel.  I think everyone needs to get out and travel more.  Pick a place then figure out how to get there…for free! Jeff – Thanks for sharing your thoughts on having Big Travel with Small Money!

If you’d like to be considered for our interview series, please send me a note!

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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