[Tuesday Conversation] Gary Leff Talks Travel

Today we are proud to introduce a new feature on Jeffsetter that I am hoping will catch on and become a regular feature. We are calling this feature the Tuesday Conversation and I plan on conducting more travel interviews with travelers who inspire me.

When I first hatched this concept, I knew that I wanted the first interview to be with Gary Leff, the longest tenured points and miles blogger I know and the person I have turned to the most over the years in order to learn how to use points and miles to help me realize my travel dreams. Gary has been blogging for over 10 years and you can learn something new from him every single day on his View from the Wing blog. I have been reading Gary’s blog for the past 3 years and credit his writing as the main reason why I got into travel hacking and blogging myself. It’s only fitting that Gary be my first interview on Jeffsetter.

Thanks to Gary for taking the time to answer my questions and thank you for reading as well. Since this is the first interview, I would love feedback on the format, content, etc.

1) You do it all: Travel the world, write about travel, found companies, participate in newspaper articles, mentor bloggers, have a day job and much, much more. What keeps you motivated to continue to grow in your areas of interest?

 [Gary Leff]: We all have hobbies and passions. This, for me, is both. Some people do fantasy football in their spare time, or watch HOUSE. I think about loyalty programs and travel.

2) If you sat next to the director of the TSA on a trans-continental flight from New York to Los Angeles, what would you talk about? Would it be 5+ hours of constructive criticisms or would you simply ignore them and get your work done?

[Gary Leff]: The problem isn’t that the TSA hasn’t ever heard the arguments. Jawboning the current TSA director won’t help. The TSA has tried a few small steps towards sanity like stopping the search for minor objects at the checkpoint, but the reaction is a political nightmare. Think about it: If they were to move forward despite the backlash and anything visible were to get through, it’s their fault. The bureaucracy has to appear to “do something.”

Meanwhile, doing something lines up with entrenched interests that make big money on government contracts, so there’s intense lobbying there as well.

It’s little wonder that as soon as Kip Hawley was out of government he denounced current security theatre. Of course he was way too self-congratulatory about how efforts, but the mea culpas I think were sincere.

Pistole knows better, they all do, it isn’t about convincing leadership – it’s about convincing the people writ large and ideally aligning those interests which benefit with better policy.

Remember: the TSA has never, ever caught a terrorist.

3) You share most of your secrets in a transparent manner on your blog. Is there anything that you are holding back for a tell-all memoir in the future? What would you name your memoir?

[Gary Leff]: Goodness, I only share the things that (1) I believe will be sustainable, (2) that I think are on the path towards elimination anyway. There are plenty of things that I don’t touch on, largely because they’re either too obscure to be of broad interest to a fairly diverse reader base, or because I don’t think readers would have the chance to benefit if I wrote about it; since it would be quickly pulled.

I don’t always get it right, but my working model is that I don’t ever write anything that’s shared with me in confidence. I rarely break “true tricks” *first* but once they’re out there on the interweb I’ll go ahead and share them with readers.

Nonetheless, I do try to be as forthcoming and transparent as I can be. But I’m always much more forthcoming in person, after a glass of wine or a cocktail.

There won’t ever be a memoir though because the best titles have already been taken — “Instead of a Book, By a Man Too Busy to Write One” and “Memoirs of a Superfluous Man.”

4) Your blog name View From the Wing is just about perfect, but is there anything you would change about it if you could do it all over again?

[Gary Leff]: When I first started my blog it was titled, “More Room Throughout Coach” and the idea was getting a roomier travel experience for everyone. I’m sure glad the name changed early, since not only was I probably infringing on one of American Airlines’ marks, but they pulled the product and the name became pretty anachronistic pretty quickly.

I don’t think the name of the blog much matters, except that it does not change once established. It mostly stands for “me” and that’s what you get with View from the Wing – what I happen to be interested in on any given day.

Note from Jeff: Thank goodness Gary didn’t decide to name his blog Leffsetter! I would have had to adopt a totally different persona if that were the case… 

5) Are there any destinations on your bucket list that you haven’t visited yet? Is it because the destinations are not points and miles redemption friendly?

[Gary Leff]: My biggest constraint is time. There are plenty of places to go and I have to fit it all in with work and other travel obligations. Good deals keep coming up that I can’t pass on, either, and so various destinations tend to “jump the queue.”

But I also don’t worry too much about the order in which I see places, or squeezing in everything I possibly can while I’m there — it’s a big world but there’s time, little by little I’m seeing what I expect ex ante to be most interesting to me. I’m learning as I go, getting better at making those estimations, and I also have a long lists of places to go back to.

6) Speaking of bucket lists, do you have one? Does your bucket get bigger over the years or are you slowly running out of new places to see?

[Gary Leff]: When I first started I didn’t know enough about the world to have a bucket list, and now I’m more or less just along for the ride…

7) Many points and miles fans learn how to earn and redeem miles from you. Who do you learn from?

[Gary Leff]: It all started for me just by reading the fine print of the newsletters and advertisements that programs sent me when I first started my professional career about 16 years ago. Much of the learning has been through trial and error, and most of the learning about redemptions has been through deep practice — redeeming hundreds of millions of miles worth of premium cabin international awards for clients.

My inspirations are:

• Steve Belkin, also known in online forums as “beaubo” — Scale the deal. Go big or go home —
• Mark Love aka “PremEx” who hasn’t been active in frequent flyer forums for years but who taught me more than anyone about how to *approach* travel. He taught me how to think about my interactions with people working for travel providers on a day by day basis (to understand them as people, and with individual motivations) in order to have the very best outcomes.

If there’s a single blog I enjoy and find valuable it’s Lucky’s at One Mile at a Time. More broadly, I learn from the very giving community of folks at Milepoint.com.

8) Outside of traveling the world, do you have any interests that readers would find surprising?

[Gary Leff]: I’ve written direct mail fundraising under the signatures of two different Majority Leaders of Congress. I’ve been cited in multiple law review articles. And I’ve served on multiple non-profit boards of directors.

 Thanks for your time today Gary! What did you think? I’d love to hear your thoughts in the comments.

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