In an ever-expanding internet kingdom of travel-reward nerds, Gary Leff reigns supreme. He has penned the blog View from the Wing for 23 years while maintaining a full-time career as a chief financial officer at a university research center. But miles, points, and rewards are not merely a side hustle or a second job; they’re a lifestyle.
“I couldn't tell you how long I spend on the blog, because I’m doing the things that I enjoy anyway,” says Leff. “I’m enough on the spectrum that I forget anyone’s reading.”
Speaking with Leff gives the impression of a human spreadsheet with a brain full of open tabs, continuously performing a complex calculus to extract maximum value from every flight, hotel stay, and credit card purchase. We asked him for the methods to the madness.
WIRED: First, give us the scoop. How many credit cards do you have?
Gary Leff: I do not know the answer to that question. I've got a drawer here next to my desk with a stack of them. When it's time to evaluate the future of my relationship with a card, I put that reminder into my calendar. I have a system for managing it. I know how I use each card. For anything that I do, there's a very specific value proposition attached.
Do you know how many loyalty programs you belong to?
For travel-related loyalty programs—that’s airlines and hotels but not individual credit cards—it’s probably somewhere in the 70s.
How did you become interested in the power of points?
I earned my first points as a teenager, flying to Australia to visit family. Those were points that I ultimately let expire, which I'm ashamed to admit. But the airlines would send you things in the mail, and I would read the fine print and say, gosh, there's some interesting offers here. Like, if you dine at these three restaurants, you can earn a whole bunch of bonus miles. Well, wait a minute, it doesn't say anything about minimum spending at these restaurants, so I can walk in and get a soda to go, right? The math worked out pretty well.
What’s been your best triumph?
I’m always on alert not just for deals and discounts but mistake fares, too. Those used to happen much more frequently than they do today. I once took advantage of a currency issue where a hotel on the beach in Thailand published their room rate in Ugandan shillings instead of US dollars. We had the presidential oceanfront villa with its own pool for $33 a night, inclusive of breakfast and tax. I paired that with a deal through American Express Travel where you could book the Conrad Bangkok presidential suite for $51 a night.
Oh my God.
Another time, I was looking for flights within French Polynesia for my honeymoon. I knew that domestic flights were running around $330 round-trip, but Travelocity priced it instead at $33 due to a currency conversion issue. It’s just a matter of paying attention, looking at the fine print, and meeting other people and sharing opportunities with them.
Is that how the blog started—a passion for sharing the fine print?
When I lived in Washington, DC, in 2002, a bunch of people I knew were starting political blogs, but I didn't feel like I had something unique to say that nobody was saying in that space. I thought, what is it that people ask me about? So I just started writing up travel tips. One weekend in May I set up a free account at Blogspot.com and started writing for, you know, 30 people reading it, and then 500, and then 1,000. Last month, June, blog traffic dipped a bit to 5.5 million visitors, but in March it was up to 7.5 million.
All right then, let’s talk numbers. Every point system feels a little different than the last. It’s hard to know what, say, 100,000 miles is really worth when it comes to any given loyalty program. What’s your method?
So, I have a close idea of the value of each currency. I value a Marriott point at 65 basis points, for example, and a Hilton point at around 40 or 45, which is about where I value an IHG point, whereas I value a Hyatt point at 1.4 cents, which is around what I'm valuing an American and a United mile at. I'm valuing a Delta mile at about a penny, a Virgin mile at about nine-tenths of a cent.
Using those metrics as a rule of thumb, how do you make the most of your miles?
You want to think about the value of miles as a private currency. There's no central bank, and it’s going to be subject to a given price level. The simplest model for this is the same sort of analysis you would do with inflation for a government-issued currency. Take the simple monetarist formula, MV equals PQ. The amount of money in the economy times velocity, or the speed at which it's spent, is going to be equivalent to the amount of Q, quantity, the amount of goods in the economy, and P, the price level, right?
Yes, right. I knew that.
Price is affected by the quantity of seats on planes. Airlines have gotten quite good at what they call capacity discipline and not flying flights that aren't selling. They're printing a lot more miles than are being redeemed in a given year, and there are a lot more ways to earn the miles.
How can a newbie get started?
Don't leave miles on the table. Sign up for programs. Track your points. I use AwardWallet, but keep track of your accounts however you want to do it. Grab your account number when you're buying something online and go through a shopping portal. Maximize it by comparing portals, whether it's something like Savewise or Cashback Monitor.
You sound like someone who, like any good points hacker, knows their way around Microsoft Excel.
I don’t really use spreadsheets. I have a really good memory, and I've been paying attention to this stuff for almost 30 years.
