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.
This story is part of The New Era of Work Travel, a collaboration between the editors of WIRED and Condé Nast Traveler to help you navigate the perks and pitfalls of the modern business trip.
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