On a Wednesday afternoon in June, Brian Kelly, better known as the travel guru the Points Guy, left his office, on Park Avenue, and boarded a helicopter on East 34th Street. Six minutes after takeoff, he touched down at John F. Kennedy International Airport, and approximately seven minutes after that, with the help of his T.S.A. Pre status, he was through security and perched at the bar of a lounge inside Terminal 5. When I arrived, twenty minutes later, still flustered from maneuvering a rolling suitcase around a packed A train for the better part of an hour, he was sipping a complimentary glass of Sancerre and chatting up a male model he had ushered into the lounge with a guest pass.
Kelly has made a career out of flying first class around the world, subsidizing his trips with a seemingly endless supply of credit-card points and airline miles and, on his Web site, ThePointsGuy.com, advising his readers on how to do the same. His site, which attracts around four million readers a month, reviews first-class cabins and V.I.P. lounges, and breaks news about credit-card offers with enticing sign-up bonuses and rewards. Despite airlines’ reputation for uncouth treatment of passengers—dragging them off oversold planes, threatening jail time, forcing them to squeeze into skinny seats like so many chickens into a coop—Kelly insists that we’re actually in a “golden age” of travel. You just have to know how to game the system.
Maxim No. 1, Kelly says, is “get the right credit cards.” “Not only are the sign-up bonuses really high, the competition is so fierce,” he told me. The Points Guy is an avid collector—he currently has twenty credit cards, down from thirty. Credit-card companies also pay him now, via affiliate marketing—he gets a nominal fee when someone clicks through his Web site to apply for a card, which is explained in a disclaimer posted at the bottom of every ThePointsGuy.com page. (Last year, after reading the Points Guy’s iPhone app, my fiancé convinced me to get the Chase Sapphire Reserve card, which at the time came with a hundred-thousand-point sign-up bonus.) “I used to really worry, Am I a snake-oil salesman?” Kelly told me. “I’m asking people to get these financial products, but as long as you’re smart about it and pay your bill off in full—which, everyone knows, it’s your responsibility—I’ve never gotten a single e-mail that said, ‘I got points and I wasn’t able to use them.’ ”
While we were talking, a guy in a black leather jacket approached Kelly, roll-aboard trailing behind. “You’re the Points Guy, right?” he asked.
“Yeah! Hey, how’s it going?” Kelly replied.
“Thank you so much, man,” the guy said. “You got me into points so many years ago, and I just got in here,” he gestured around the lounge, rife with coveted electrical outlets and little bowls of Chex Mix. “Thanks a lot, I appreciate it.”
I asked Kelly what most people don’t know about maximizing their points. “Link your credit or debit card to shopping or dining programs,” he said. “The dining programs are crazy. Link your account, it takes two seconds, and, anytime you dine at a participating restaurant, you get points in your account in addition to the points on your credit card. It’s like double dipping.”
Then there are frequent-flier miles. “Last minute is the best time to use them,” he said. “Most people think you should redeem eleven months in advance, but that’s an old adage. The airlines now have better computer systems. Within the week of departure, or even the same day, tons of award seats—tons—the very best, open up. If you have a little bit of an appetite for risk, wait until the week of or a couple of days before.”
To prove it, Kelly whipped out his phone and pulled up the Alaska Airlines app. More tech savvy than many of its competitors, it allows users to search for award fares on partners such as Emirates, which has ultra-luxe amenities including functioning showers and an onboard bar. “Let’s go to Sydney—that’s always the hardest,” Kelly said, tapping his screen. “Right now, tonight, we could go economy for forty thousand miles and forty-one dollars. It’s nothing.”
Instead, we’re off to Los Angeles (home for me, meetings for Kelly—to brainstorm a possible Points Guy television show). He checked his watch and said, “We actually have to board.” He shrugged on a cardigan and sauntered to the men’s room. At six feet seven, he doesn’t do well in airplane lavatories. “I joke that that’s how I’m going to die, just a little bit of turbulence and. . . .” He mimed the side of his head crashing into a wall.
Kelly’s fascination with airfare deals started at the age of twelve, when his father, a pharmaceutical consultant, got a job at a California startup and asked Kelly, the family’s resident computer whiz, to book his flights back and forth from Philadelphia, where the family lived. Kelly would use Travelocity, which was new at the time. “I used to call it Travel-oh-city, because I had no idea,” Kelly said. “My dad paid me ten dollars per booking because he thought I had called the airline.”
In college, Kelly attained his own élite status and discovered FlyerTalk, an online forum of mileage-and-points enthusiasts. One of his first jobs after graduation was in human resources at Morgan Stanley, where he’d fly between colleges to recruit I.T. professionals. When the 2008 financial crisis hit, he took on an additional role: “Every time we had a major layoff, because I’m so tall, I’d wait outside in a suit to escort people to the lobby,” he told me. “It was miserable.” Many times a day, he’d soothe himself by checking his frequent-flier accounts.
In 2010, at the suggestion of friends, Kelly turned his hobby into a serviceable Web site. “At first, it was just a smart form—tell me your name, where you want to go, and how many miles you have,” he said. “I’d figure it out, like a crossword puzzle, and you’d pay me fifty dollars via PayPal. It was a little travel agency for points.” Kelly promoted the site on Facebook and began blogging about credit-card offers. One day, a college friend who worked at Chase asked him to meet for drinks. “I thought he was asking me out on a date, and I had no interest,” Kelly said. “Finally, we had a glass of wine in Times Square, and he said, ‘You’re the dumbest person I know. You’re direct linking to credit-card companies and they will pay a stupid amount of money for that.’ ”
During his first month of affiliate marketing, in February of 2011, Kelly made five thousand dollars. Two months later, he published a post about a hundred-thousand-point bonus offer from Chase and British Airways. Hundreds of readers applied for the card. He made thirty thousand dollars in twenty-four hours and gave notice at Morgan Stanley the next day. Today, his sway has grown so strong that many banks consult him before releasing new credit cards to the public. (Since 2012, the Points Guy has been owned by Bankrate, a consumer-finance company.)
We were somewhere above Ohio, noshing on taro chips and eggplant dip, by this point in Kelly’s origin story. He grew contemplative. “I’m a middle-class kid, my parents put me through college; I fully understand my privilege,” he said. The nature of his job—chastising a first-class lounge at a Chinese airport for using plastic cutlery instead of silverware—used to make him feel guilty. So, last year, he started Points for Peace, an initiative that partners with the nonprofit Peace Jam to fly Nobel laureates to children who might benefit from their guidance. “Everyone looks at charities, like, ‘Oh, they have too many administrative costs and travel,’ ” Kelly said. “I said, ‘What if I come in and help?’ ” Kelly now travels every few months for Peace Jam events in sub-Saharan Africa. Last June, in Ghana, he held a “Shark Tank”-style competition with three hundred and fifty teen-agers, awarding micro-finance loans to the most entrepreneurial of the group. He told me, “When I see talent, I want to develop it.”
Prior to boarding our JetBlue flight, Kelly received a text message from the airline’s publicist: Did he know that there was a thirteen-year-old boy in Pakistan marketing himself as the Points Guy, Jr., e-mailing various airlines, asking for free flights and discounts? Kelly did know. He had plans to meet the boy, Shailen Verma, in New York the following week, as part of a birthday present organized by Verma’s parents. On the plane, Kelly told me, “I’m going to sit him down and tell him how great it is that he’s enterprising, but he’s got to come up with a different name.”
