Don’t Get Out of the Points Game, Says the Points Guy

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Brian Kelly, also known as the Points Guy, built a small empire out of working the system, so it shouldn’t be a surprise that he’s also an expert at gaming restaurant reservations. 

When the former Morgan Stanley recruiter started the Points Guy blog in 2010, his audience was the equivalent of extreme couponers, but for hotels and flights instead of bulk groceries. “Points people”—competitive, slightly nerdy, obsessive about getting the best deals and eternally online—soon began flocking to the site, which made money through affiliate marketing. Next came an app and a points valuation calculator. In more than a decade at it, Kelly has grown his hobby into a website, online community and consulting business.  According to him he started with a $10 domain and a WordPress blog, so to be what it is now and to still be profitable and growing is incredible.

The typical points person today is what finance professionals dub a “Henry”—high earner, not rich yet—Kelly explains, pointing to the thirtysomethings next to us indulging in lavish meals on a Tuesday at noon. “It’s people who are working in good jobs and want to travel but just don’t have $10,000 to spend on flights,” he says.

But air travel and points these days aren’t just optimizing for that first-class upgrade or bonus resort getaway. Travelers are dealing with melting-down airline technology and crumbling planes. They’re having to contend with travel companies that are pinching them after they’ve spent years accumulating loyalty points—so much so that in September the US Department of Transportation began probing the four largest US carriers’ points programs on the devaluation of earned rewards, hidden or dynamic pricing, extra fees, and reduced competition and choice.

All this chaos and confusion isn’t great for travelers, but it is for Kelly, who’ll publish his first book, How to Win at Travel, in February. There he’ll set out to prove he’s more than just a points evangelist, recasting himself as a consumer advocate helping travelers fight back against an establishment designed to take advantage of them. He’s also taking on Airbnb Inc. with a curated vacation rentals platform as part of a collaboration with former Points Guy exec John Sutton. The venture, called Journey, will feature home rentals and boutique hotels that users can book with points accumulated through its own loyalty program. Journey also plans a credit card for frequent travelers.

Although the 41-year-old describes himself as an “Instagram boy,” he recognizes the importance of meeting consumers where they’re at—and right now that’s TikTok. The Points Guy account, which has about 750,000 followers, is filled with videos of Kelly going on tours of new airport lounges, giving tips like using AirTags to locate bags or discussing how potential credit card legislation would affect consumers.