When Brian Kelly was just 13, he booked his entire family on a free trip to the Cayman Islands.
How did he accomplish this as a teenager? It turns out that his father, a travel consultant, racked up lots of frequent flyer miles. When the statements arrived in the mail, he had no idea what to do with them.
“My dad didn’t know how to use a computer at the time,” says Kelly. “So I was just like, ‘Let me see what we can do.’”
Kelly figured out how to get all six members of the family down to the Caribbean—four of them on one airline, two on another. The whole trip cost them just a bit more than a trip to Disney World.
Being such a whiz at finding deals, it’s no surprise that Kelly went on to be founder of The Points Guy, a guide to finding the best airline rewards.
Kelly started tallying his own travel points while in college. When he studied abroad in Spain or spent spring break in Ireland, he banked his miles. He began flying first class, amazing all of his friends.
“I was travel points rich and cash poor,” says Kelly, who by this point had graduated and was enduring a “dismal” job at Morgan Stanley. “That’s when I realized my passion was in travel and loyalty programs.”
In 2010, Kelly launched The Points Guy, blogging in the persona of a busy travel consultant living in New York City. By the end of the year, the blog generated 50,000 unique monthly visitors. He even got recognition at a party.
“I was at my first cocktail party, and someone said, ‘Oh my God, are you The Points Guy?’” recalls the WeWork FiDi member. “It was an unbelievable feeling.”
Since then, Kelly has become one of the most recognized names in travel. His website has increased its monthly readership to more than 3 million, and keeping up with the latest news requires 10 full-time employees and a stable of about 15 regular contributors. Besides airline miles, The Points Guy also covers the best credit cards, issues alerts about hot deals, and covers news about the travel industry.
Kelly also shares business travel tips with up-and-coming companies. Next week, he’s hosting two Small Business Week events—one at Chicago’s WeWork Kinzie and the other at New York’s WeWork FiDi—where he’ll share advice on how businesses can best utilize travel points and learn how this will help with their bottom line.
“I hope we can expand this to other locations like D.C. and San Diego,” Kelly says. “I love doing what I do and love helping people, so it’s going to be successful.”
Brian Kelly is hosting two events focusing on business travel: the first event is at 5 PM on Nov. 15 at WeWork Kinzie, and the second event at 5 PM on Nov. 22 at WeWork FiDi. Reserve ahead, as space is limited. The events include a Q&A session and private consultations.