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. 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. Gary Leff belongs to 70-plus travel loyalty programs. Photograph: Liz Moskowitz 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.