“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!

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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