No one likes a bargain like Brian Kelly, a prolific air-mile collector and the CEO of thepointsguy.com — at least when it comes to first-class flights.

Kelly, who used to work in HR at Morgan Stanley, has turned his side hustle and passion for flying premium into a revenue-generating lifestyle brand that has become a mecca for anyone trying to get their head around how to start collecting air miles.

Now he spends most of his time, or at least two weeks a month, flying around the world in some of the fanciest first-class cabins, virtually for free.

Business Insider caught up with Kelly to hear about his journey from a Morgan Stanley cubicle to becoming a macro-travel influencer.

Scroll down for a look at how he did it.


Meet 34-year-old Brian Kelly, aka The Points Guy. He left his job in HR at Morgan Stanley in 2011 to build his air-miles blog.

Now he spends at least two weeks a month flying around the world in some of the fanciest first-class cabins — virtually free.

Recent feats include Hong Kong to San Francisco with Singapore Airline for 92,000 Singapore Krisflyer miles and $78 …

And JFK to London Heathrow with American Airlines for 62,500 Alaska miles and $18.10 (£13.70) one way.

His career certainly takes him to some pretty amazing places, like Africa.

He told Business Insider: “I’m a huge Africa lover, and South Africa is my favourite overall great. I love the animals, the wine country, the people and the food — it’s unbelievably beautiful, you really can live like a king even on budget.”

He’s also been diving in Thailand.

Kelly’s enthusiasm for airline points began when he was 12. He credits his career to his dad, who he calls “the original points guy.” His dad travelled with work, and Kelly started to book his travel for him via Travelocity, earning $10 a reservation.

He started collecting his dad’s frequent-flier miles. The same year, he used them to book his family’s first holiday to the Caribbean, in the Cayman Islands.

“The rush you get from your first redemption will drive you for the rest of your life,” he said.

By the time he was a student at the University of Pittsburgh, he had gold status on US airways. “I was a college student with no income, but all of sudden I’m getting first-class upgrades left and right,” he said.

He soon realized that there was a whole community of people just as obsessed with points as him, both within travel blogging and gay communities, both of which he was a part of. He would fly to events and socialize with people who were just as mad about premium class as he was.

Still, he hadn’t yet figured out how to make this into a career. At 22 he moved to New York and got a job in retail, which offered just two weeks holiday a year. “I was earning $45,000 a year and struggling to make ends meet. I’d used up my miles, and spent years not even traveling — just making my rent, and living in poverty in Manhattan, rinse and repeat.”

He was hired by the Morgan Stanley tech recruitment team in 2007. He said he thought: “I’m gonna be rich!”

But it was also just before the global financial crisis hit. “The week I started the markets started to crack,” he said. He managed to hold on to his job because he was hiring employees in the tech department, but at one point his team of six was reduced to just him.

“Work sucked it out of me, I had to lay off so many people. Every Sunday evening my stomach would be in knots and I’d get the email about who I had to fire next. I’m 6’7″ and would have to escort ‘lifers’ down the elevator and out the door. I realized no one was irreplaceable.”

He said he started to “fly like crazy to escape New York and the depression there. At the time the travel industry was giving away crazy bonuses. I was getting over 1 million points a year, and me and an ex flew first-class to the Seychelles.”

Over the next two years, Kelly started selling his travel and points advice online and over the phone, making a small commission from the savings each booked trip made.

Eventually he turned it into a blog and began furiously posting points advice each night after work. He told Business Insider it eventually frayed his then long-term relationship because he was so busy.

At the same time he began to achieve a bit of fame. “I was at a cocktail party in New York in the fall of 2010, and some guy came up to me and said ‘Hey, you’re the points man!'”

It was shortly after this meeting in 2011 that Kelly said he had a eureka moment and, persuaded by a friend, realized he could monetise his site through affiliate advertising.

“At that time I was, like, a micro influencer, but I was sitting on a goldmine and had no idea,” he said.

His first post that went viral made him $30,000 (£22,700) in one day, he said, and overnight he began earning cash from his blog. Several months later, in June 2011, Kelly said he quit his cubicle at Morgan Stanley after receiving a six-figure check and off he flew to Asia.

And it’s apparently been “crazy” ever since. Kelly decided to sell his website in May 2012 to bankrate.com, but he said he maintains creative control of the company.

“It means I don’t have to deal with all the stresses of a startup, like legal and accounting, but get to do the fun things like design the floor for our new office space,” he said.

He added that “revenues are crazy” and traffic continues to grow by 50% each month.

His favorite airline is Emirates, he says. “Simply because I love the A380. It’s a quiet, beautiful plane, with two showers in first class. And they really put the passenger on a pedestal, even in coach.”

Domestically, it’s JetBlue and their Mint business class all the way, he says. “It’s amazing — I fly New York to LA and you get seats right close the door and tapas-like small food plates.”

Kelly said the biggest mistake people make with air miles is “giving up before they even begin.”

“Google’s your best friend,” he said. “Teach yourself over coffee on a Saturday morning if want to take that trip to the Maldives.”

“People get overwhelmed — no one teaches us this stuff,” he added. “But once you arm yourself with information, set a goal and work back from there.”

“No one wants to change a credit card, but you do it in the context of, ‘This is taking me 1%, 2%, or 3% closer to that trip to Hawaii’ or ‘Shopping for the holidays on this credit card will get me 10% there.'”

Ultimately, Kelly credits the success of his site to the millennial way of living.

“These days if a millennial pays for dinner with a debit card they look dumb — it’s the same as paying in cash,” he said “Ask yourself the question — do you want your bachelor party in Atlantic City or do you want to take all your friends to Ibiza?”

This article originally appeared in Business Insider.

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