“Don’t just earn the most points for the sake of earning them.”

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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:  We Fly Free 

Justin writes We Fly Free to show folks how to travel around the world without paying a lot of money!

We Fly Free - Interview with Justin

Visiting Hawaii with Cara

How and when did you start collecting miles and points?

I started collecting points 3 years ago with a single American Express Zync card (no longer available).  I still remember my first “big” score was when I was in Vegas with a group of 10 friends and I convinced everyone to let me put our whole bar tab on my card.  They just re-paid me in cash.

Bottle service in Vegas can get quite expensive and I got 2x points on restaurants, so it was quite a haul for me!

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

We Fly Free - Interview with Justin

Popping over for a long weekend to visit a buddy in London

Three reasons.  First, it’s been a great creative outlet for me and spared my girlfriend from continuous questions about flying (“would you mind if we stopped in Houston on the way to Germany?”).  I just love this stuff so much that it’s hard to get off my mind and flushing things out on [virtual] paper helps me accomplish other things.

Second, it’s forced me to learn about (so I can post about) different programs than I’ve ever used for myself, and writing about different things has spurned other ideas.

Finally, I really wanted to do an award booking service, and I thought it would be a good compliment.  I honestly would do award bookings for free if they didn’t take any time, I love doing them so much.  Generally I’m more over-eager than my clients are!

I’d like to think one thing that makes it special is that I try to write from the perspective of a young professional couple.  I try to write about trips that we might enjoy and ways to earn miles that are usually available to younger people.

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

Keep your head in the game.  If you’re out at Nordstrom Rack and see some stuff on the clearance aisle marked down 75%, check Amazon and eBay and see what they’re going for.  You might even be able to turn a small profit.  I’ve earned a few thousand miles re-selling iPad cases and such.

What’s your most memorable travel experience?

Breakfast in Thailand with my girlfriend Cara.  We got a great Amex Fine Hotel & Resorts rate at the Four Seasons Bangkok for around ~$170 and probably got at least half of our money’s worth in the free breakfast.  I remember sitting outside during a beautiful Thai morning (it wasn’t too hot yet at 7 am) and enjoying the best breakfast we’ve ever had… we still talk about that breakfast 2 years later.

We Fly Free - Interview with Justin

Christmas in Hong Kong

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

They think I’m absolutely out of my mind.  My dad in particular just can’t wrap his head around the fact that there really is no catch to it.  Of course I just booked them on their second annual free trip with his Delta miles, so we’ll see what he says when they get back.

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

Reading trip reports is super useful and a great escape from reality.  I really like knowing what to expect the second I step on board or get out of a taxi at a hotel.

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

A hotel waitress spilled water on me one time in view of the general manager.  I didn’t even make a stink about it, but he came over to apologize and dropped 1,000 points in my account anyway.

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

This might be an obvious one, but keep your travel goals in mind.  Don’t just earn the most points for the sake of earning them.  I found myself at one point with over 500,000 airline miles and barely any hotel points.  The reason is that airline miles are so, so much easier to earn that I was just taking the path of least resistance.

I think I just lost track of the fact that I actually need to use them for travel at some point.

What would your readers be surprised to know about you?

I don’t actually get to travel all that much.  I own a business in the Washington DC area, and other than a hard-working spaniel mix, I’m the only full time employee.

Any parting words?

We Fly Free - Interview with Justin

Me in the Supreme Court Judge’s chair in London

Don’t forget to sign up for dining programs with all your credit cards.  I don’t usually go out of my way to eat at a restaurant on the lists, but it’s always a nice surprise to see some extra miles in my account courtesy of a dinner a few weeks ago when I didn’t even know I was earning any.

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

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These responses are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.

17 responses to ““Don’t just earn the most points for the sake of earning them.”

  1. Great point about having travel goals – you need a plan.

  2. I wonder if one could tip a waitress to spill something on them?

  3. Cara is cute.

  4. more pics of Cara please

  5. How many points to get Cara?

  6. ^^Creepy

  7. Gotta love the internet. Friday interviews have taken on a life of themselves within the comments sections.

  8. More pictures of the sexy Cara…please !

  9. cara’s using you for your miles

  10. @Alex she earns her share too…

  11. Who’s that Hunk your with in the other pic?

  12. Cara! More, please!

  13. I like attractive women as much as any guy but, in my opinion, this isn’t the place for remarks and wisecracks on that. I hope Daraius will remove them as it cheapens the blog, and I am sure will make some hesitant to be interviewed in the future.

  14. Are you from Texas by any chance?

  15. Nope… DC by way of South Carolina and Virginia

  16. You make a good point about having travel goals. With all the credit card signup bonuses since the end of the Great Recession, I’ll admit it is a lot easier to travel than before. I was hesitant myself to apply for some of these credit cards with huge bonuses until I knew beforehand of some travel I needed to do (i.e. travelling to India for a friend’s wedding.)

  17. Laurel Ann

    Great post! Very good tips on setting goals for where you really want to travel. I like your website and will likely be contacting you for award redemptions in 2014.
    And yes… Cara is very pretty.
    (silly boys)

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