Brian Kelly, the founder of The Points Guy, a website devoted to maximizing credit card, airline and hotel loyalty points, was 12 in 1996 when he booked his first free trip, using his father’s points to arrange for the family of six to vacation in the Cayman Islands. Later, working as a recruiter for an investment bank, he began accumulating his own points for business travel, spending them on annual vacation sprees that so impressed his friends that he earned the nickname The Points Guy. In 2010, he began blogging under the name and, one year later, quit his day job to go full time into points hacking.
Now his site covers travel news with an editorial staff of about 40, and last fall the brand created a mobile app that allows users to track their loyalty points in one place, see their monetary value and get advice on how to spend them.
The process has not been entirely smooth. American Airlines, citing confidentiality, recently sent The Points Guy a cease-and-desist letter. Last month, Red Ventures, which acquired The Points Guy in 2017 and also owns the travel publisher Lonely Planet, preemptively sued the airline, asking the court to rule that consumers can manage their frequent flier accounts on a third-party site. American has countersued.
The app, for now, is carrying on in the service of “educating consumers,” said Mr. Kelly in a recent interview. The following are excerpts from that conversation, edited for length and clarity.
What is The Points Guy app designed to do?
Points and miles have gotten a lot more sophisticated since the old days when you got them from flying and redeemed them for free tickets. The game has gotten a lot more complicated, but consumers can still win if they play it right. The average consumer simply does not have the capacity to crunch what credit card to use, and people are points-hoarding because they don’t know what’s a good use of points.
The Points Guy app has three main tenets: learn, earn and burn. Learn is content. If you have an American Express Platinum card, we want to let you know when there’s a big bonus you need to engage with. The second piece is earning. We crunch the numbers and say, hey, you’re spending a lot of groceries on this card that only gives you one point per dollar. Did you know if you used your gold card, you’ll get four points per dollar on groceries? On the burn part of the app, that’s where we want to help empower consumers. Most consumers don’t know they can redeem American miles on Qatar Airways.
We want to be able to show people their whole net worth in points in one spot because people have a lot more in value than they realize. The point of the app is to get people to engage more in loyalty so that they can use their points and travel again. We also will let you know if your miles are going to expire. A lot of programs have not done mileage expirations during the pandemic, but starting April 1, 2022, American will expire anyone’s miles if they don’t have any activity within the last 18 months.
Your platform has grown enormously. What’s next?
The key plan for The Points Guy in 2022 is to continue to invest in content. We want to reconnect with our readers in deeper ways in online communities, where people can learn about different loyalty programs with the goal of helping people not just think about travel, but actually plan it and execute it and be their go-to guide for the resources they need to explore the world.
Like a travel agency?
I don’t think we’d want to become a travel agency, but we want to help people choose not just what points to use to fly, but once you get to Osaka, how to explore. So, we’re teaming up with Lonely Planet, but also leveraging our community. We believe the time is now. A lot of people have taken off travel, but they’re ready to go back. At The Points Guy, we’re excited for the traveler to get back out there confidently again.
What’s a fabulous free trip you’ve done using miles?
Oh, there’s a lot of them. During the pandemic, my favorite trip was to Tahiti. It was one of the few countries that was open and had a pretty progressive testing stance. It was September 2020 and I used my American miles to fly Air Tahiti Nui business class from Los Angeles. I used Amex points and transferred them to stay at the Conrad Bora Bora Nui for free. It was still peak pandemic and it helped me reconnect. I swam with humpback whales off the island of Moorea, which was completely life-changing. That was my regeneration trip.
Many will read this and say, “I don’t travel much, so his advice doesn’t apply.” What’s your response?
You don’t need to travel to get points. Do you shop? Do you buy groceries? Do you eat out? Most people do those things. The points game is not for the frequent traveler. It’s for people who spend money. The sign-up bonuses for credit cards are massive. A single bonus a year can give you a free trip. And I think that’s when people realize, “I don’t need to be a business traveler to fly for free anymore.”
How many credit cards do you have?
I have 25 credit cards, which I don’t recommend the average person get. However, it is my business. Even if you don’t want to travel, there are cash-back cards you should get. If you’re paying in cash, simply put, you’re throwing money away on every transaction. Because, for the most part, in the United States, points are built into the cost of goods. When you go to Target, you don’t get a discount for paying cash. So, you could be earning super valuable points or cash back.
Do you carry cash?
I do carry cash because I love to tip. I used to be a waiter, and especially frontline employees have been so hard hit these days. But I won’t pay for anything in cash. When you put your purchases on credit cards, there’s an extra layer of protection that you don’t get when you use cash. And when someone steals your cash, good luck. But if someone steals your credit card, you’ll get all of that back. For a lot of reasons beyond points, having a good credit card these days is like having an extra line of defense, especially since so many airlines have had these operational meltdowns. If your flight’s delayed and you use a travel credit card, with a lot of them you have up to $500 in free travel protection to pay for a rental car or hotel. So, using the right card makes sense for points and protection.
Elaine Glusac writes the Frugal Traveler column. Follow her on Instagram @eglusac.
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