“I cherish each of the trips I’ve been able to take with my wife to see places I never dreamed of…”

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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: Gary Leff of View From The Wing

If I had to read only one frequent flyer blog, I’d read View From The Wing, so I was very excited to chat with Gary!

Gary writes the View From The Wing blog on BoardingArea and combines deep analysis of current trends in the frequent flyer world together with some of the best tips on how to redeem your miles for aspirational awards.

But that’s not surprising since Gary has redeemed over 100 million miles for premium class international travel all at the low level and is a co-founder of frequent flyer community MilePoint.  In other words, Gary knows miles and points!

View From The Wing - Gary Leff Interview
Gary Leff & His Wife At El Bulli in Roses, Spain
How and when did you start collecting miles and points?

I collected my first miles on a trip to Australia in 1991.  I flew American Airlines via Honolulu.  I let the miles expire.

Fast-forward to the mid-90s, I’ve graduated college and I started working.  I was traveling for work, flying back across the country to visit family regularly, and making twice-monthly trips to visit my college girlfriend.

I joined the major US frequent flyer programs and started reading all of the materials they sent in the mail.  In my current job I often joke that I read fine print for a living.

But that’s what I did with the program materials, “you mean if I eat at 5 restaurants on this list in the next two months I’ll earn 20,000 bonus miles?  And any purchase, even a soda, counts?

And for just a few more miles than a coach ticket in the US I can go back to Australia in business class?  Wow, these programs are just fantastic!”

Why did you start View From The Wing?  What’s special about it?

I started reading blogs about 10 years ago, saw that you could create an account at Blogspot and start one yourself.  So I did.  The original name of my blog was “More Room Throughout Coach” … borrowing the line from American Airlines when they used to have extra legroom throughout their whole economy cabin, whereas United only had economy plus up front.

Of course American added seats back.  But my idea was ‘creating a better world for all of us’ and the blog had a bit of a different focus then, it was a mix of politics, news of the weird, and frequent flyer miles.  I called it “the blog of free minds and free miles,” also a play on someone else’s slogan (Reason magazine purports to be the magazine of free minds and free markets).  Boy was I derivative back then!

I had some early successes, including media appearances for my “Impeach Norm Mineta: Liberty & Security, Not Bureaucracy” bumper stickers – back before TSA was transferred to Homeland Security.  But I realized that there were plenty of political blogs in the world, and I didn’t really have a comparative advantage.

So I began focusing exclusively on frequent travel and loyalty programs, and I believe I was the first one.  I didn’t have much traffic back then, but I did get plenty of media for it.

I certainly never expected to have a role in Flyertalk and now Milepoint, to help create the Frequent Traveler Awards and now to bring back the Freddies, to be named one of Conde Nast’s world’s top travel specialists.  I’ve certainly received more than my share from this space.  So I like to try to give back to frequent travelers some of what frequent travel has given to me.

View From The Wing - Gary Leff Interview - Gary Leff at the Frequent Traveler Awards
Gary Leff At The Frequent Traveler Awards

In the end there are plenty of great folks blogging about miles and points, and I read most of them myself!  I’ll leave it to my readers to decide if there’s anything special about my blog.

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

It’s more than just one thing, but: sign up for programs, track your miles with a service like AwardWallet or Mileage Manager, pick a reward goal, pick a program to focus on which matches that goal until you have enough miles for the reward and then diversify, strive for elite status, don’t let your points expire.

But if you need just one thing?  Read my blog. 🙂

What’s your most memorable travel experience?

Circling JFK as an unaccompanied minor because the landing gear wouldn’t go down…  More recently, they’re all great, at least my award redemptions.

I cherish each of the trips I’ve been able to take with my wife to see places I never dreamed of (having never left the country before that Australia trip 20 years ago, except when I snuck into Mexico with friends in high school…) and in a manner utterly unbefitting my overall (lack of) station in life.

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

Most love it, because they benefit from it.  Or at least they tolerate it.  But since more than just a handful have taken their own first class trips to exotic places, I’ve built up way more capital than I deserve.

Is there any tool or trick which you’ve found especially useful in this hobby? * Persistence.  When you don’t like the answer you get the first time, hang up and call back. * Patience. Things go wrong, don’t get frustrated, every problem has a solution. * Preparation.  Do your homework, so you don’t miss out on deals or enter blindly without full understanding. What was the least expected way you’ve earned miles or points?

Giving blood.  Getting visa gift cards.  Just asking American Express for points.  Over 15 million miles from stickers.

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

Jump on deals when they happen, don’t hesitate.

That award charts always get more expensive, because miles are just a form of currency without an independent central bank or currency board.  The tendency is to inflate.

The best use of miles is premium cabin international travel.

What would your readers be surprised to know about you?

That I often fly coach for my short-hauls, DCA is so convenient to me and US Airways has plenty of non-stop flights (I’ll re-qualify for BMI Gold primarily off these segments, got to love 600 mile minimums).

That I’ve lived an even more fortunate life outside of travel than I have with miles and points.  And not just because of my ever-patient wife.  I’ve met half a dozen Nobel laureates in economics, I’ve worked with a member of the 9-11 commission, I’ve written under the signatures of two different Majority Leaders in Congress.  I’ve served on several non-profit boards.

Any parting words?

It’s cliché to say that we shouldn’t take this all too seriously, but I disagree: I’m passionate about miles and points.  I practice full contact loyalty.  I love these programs.

I think they offer a tremendous value proposition, and for all of their success I think they’re still widely misunderstood (perhaps because they’re so complicated, though therein lies the true opportunity).

I do my best to honor those programs that work well – for the travel providers and for the consumer, and to criticize those that I think are missing the boat.

Properly understood, the relationship is win-win and for my part my entire worldview has been changed by these programs, I see the world as much smaller and more accessible and I experience the world in a way I never would have thought possible.  And for that, I invite y’all to join me.

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

So if you’re looking to turbo charge your miles and point knowledge, head on over to View From The Wing.

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