Brian Kelly's website, The Points Guy, teaches 4.6 million visitors a month how to maximize their credit cards, bonus miles, and dining points to travel the globe like a CEO. 

How would you like to fly around the world in business or first class, visiting far-flung locations, relaxing in luxury hotels and subsidizing it all for little or nothing thanks to your credit card points and your bonus miles?

Sounds like a dream with too many catches right? Well for Brian Kelly, it's a reality. Founder and CEO of The Points Guy website, he's made a career out of jet-set traveling and advising his four million readers a month how to do likewise.

In an era where flights conjure images of long lines, cramped conditions, demoralized attendants and widespread misery, Kelly insists that it doesn't have to be this way. Your experience can be completely different if you just focus on your goals. Focus is the key.

He started early. “In the '90s when I was 12 years old I was using airline points for my dad to book his flights,” he tells IrishCentral.

“He worked in the pharmaceutical industry so he traveled a ton. We made it a bonding thing that I would book his flights. Every year we would use his frequent flyer miles for vacations to the Caribbean. We were upper middle class but we were taking these fancy vacations for free basically. I grew up in Philadelphia where people take trips to the shore, but we were going to the Caribbean in February for ten days and coming back tanned.”

He got wise early, in other words:  “I lived a champagne life on a beer budget and that followed me through university. I became the student body president at the University of Pittsburgh and my first trip abroad was to Dublin with my best friend and roommate Mike Kelly (no relation). We saw a $300 round trip airfare so Ireland was my first real trip outside the US. I caught the travel bug after that.”

Moving to New York after university, he wanted to make it big. First, he got a job in fashion, then he worked his way up to get a job in Morgan Stanley in Finance in the HR side. He started in August 2007, traveling across the US and Canada scoping out the top technologists.

“That was the month when the markets really started to shatter,” he explains. “Timing-wise, it wasn't the best. 2008 was a horrible year, 2009 was just depressing. I would get promoted but I'd receive no raise. They'd tell me your bonus is not getting laid off.”

Kelly remembers being sick to his stomach every Sunday evening, thinking how does he go back to work tomorrow? What kept him sane was all the travel, in particular, the millions of points he had started raking in for all the domestic flights. 

“I was able to travel personally to places like the Seychelles which helped me get through those Great Recessions times. It was my happy place, a physical and mental escape from a pretty dark time to be in the financial services industry.”

At work, he was already known as the points guy. “I remember when the managing director came up to me and said, 'OK, I want to take my wife to Paris but I'm going to use all my Amex points to buy a grill instead.' I said to him, 'You're a computer scientist, you went to Princeton, here's the math. A thousand dollar grill for six hundred thousand points or would you rather have four business class tickets to Europe?' These were really brilliant people, mathematicians, but they had no idea about what I was really smart at.”

Kelly says he's one of those weird people that read the fine print of credit card terms. “It's like treasure hunting,” he says. “There all these arcane rules, but within these rules lies the opportunity.”

Read more: Meet the Irish woman breaking down barriers in technology education

Now The Points Guy website is hitting over four million unique monthly visitors to the site and he's still keenly focused on service, he says.

“People come to the site to ask if they can use Amex points to go to Tunisia, say. Well, we have content written about that that Google rank us very high. Our business model hasn't changed that much in the seven years since I started it.”

Ninety-seven percent of The Points Guy readers are in the US, Kelly says.  “We are expanding internationally and will have content teams focused on some other countries soon. In general, the points system is a hugely profitable industry.”

“The airlines print money by selling these frequent flyer programs to the credit card companies and they, in turn, are making trillions getting people to use credit cards. Everyone has them in the US and every merchant pays between two and three percent per transaction. If you're paying in cash and not using points you're basically paying for other people’s rewards. That's the system.”

Frequent flyer programs are often the most profitable arm of the airlines but Kelly sees no conflict since everyone is making out: “I love my job because everyone can win. The banks win because people are using their cards more, the consumers win because they get to travel more, and the airlines win because the frequent flyer rewards are often filling seats that would have gone empty.”

If it sounds too good to be true the airlines themselves might agree with him.

“There is a little friction in that some airlines are increasing the number of miles you have to have to travel,” Kelly explains. “So the way you win is that credit card companies are giving away more miles than ever.”

Although he will never need to fly coach again, Kelly has remained true to his Irish roots. His great grandparents came to the US in the early 1900s from County Clare and County Cavan: “Very working class, farmers and laborers. I'm third generation. My grandmother was very into genealogy and has everything written down. I've been to Ireland a number of times – it was my very first trip abroad – but I've never been there to retrace our steps. I'm from a huge family, shockingly, my mom is one of ten children I would like to bring my eleven nieces and nephews – who are all really young now – over in a couple of years.”

Ireland, and Dublin and Galway, in particular, remains dear to him: “I often work with Betty Williams who won the Nobel Peace Prize in 1976 for her work to end the Troubles. She lives in Galway now and she's one of my favorite people in the world – and oysters are one of my favorite foods so I really want to come back to Galway in time for the festival.

“But I've not been to Northern Ireland or Donegal yet,” he confesses. “People assume I've been everywhere around the world but even within countries I’ve been to there are so many facets to Ireland that I've barely scratched the surface.”

Has he flown Aer Lingus? “Oh yes. Funny enough British Airways Avios is a popular program because there are two ways to fly them without paying huge fees that people don't know about. Redeeming them on Aer Lingus is one of them. It's one of the best ways to use British Airways miles where you'll pay twenty dollars in fees rather than nine hundred. Aer Lingus is one of the tricks I've used to fly to Ireland. But I've also flown there with United and maybe one of these days I'll take that Ethiopian flight that flies from LA to Dublin. “

What does Kelly wish more people knew about using points and miles to fund travel?

“People just need to look at frequent flyer miles as money. Once you start looking at points as money in your pocket things change. Yes, it can be frustrating to redeem them but like all things in life, if you put a little bit of effort into something you'll get greater return.

“If you are looking for a mortgage for your house do you say, give me the best one? It takes a little effort. I get that it's complex but just take a minute, set a goal, decide what you want to do. There is a great community to help you on our Facebook group the TPG where people are helping each other all day. Google is your best friend. Once you start, you'll start to see the benefits. It’s not rocket science. The more you learn the better life you will live if you want to travel. Even if you don't want to travel you can still get cashback, to get your share in the rewards ecosystem.”

Being proudly gay, does he think it has made him more adventurous? “It's amazing how many gay people are plane geeks that love to travel. There is some sort of compulsion, I don't know what it is. A lot of the aviation community are LGBT. Travel teaches you that people who are different from you are some of the most fascinating people. It's a good thing.”

Read more: “Ireland for Finance” strategy launched in New York

When I tell him what the top search question for Brian Kelly on Google is – is The Points Guy married? – he laughs. “Oh really? It's interesting because I'm dating. Social media is interesting because I get a lot of propositions from girls. They're barking up the wrong tree. I'm flattered to know that people are asking that. I'm currently taking applications.”

Kelly's housekeeper is more cautious, he admits. “Today she said you need to be careful. But I'm proud, I'm self-made. I didn't come out until right after I graduated university and I live my life very openly. The lifestyle I live is very appealing, traveling the best way possible. I'm not going to go on dates and not tell people who I am. It is what it is. I have a good judge of character. David Geffen once said I'd rather have people attracted to me because I'm successful than because of my pecs.

“In New York, there are so many successful men. I just met some gay guys in Egypt where there's no dating, no family acceptance, everything is under the radar.  I think through traveling I've realized how fortunate I am and I'm not going to complain about things. That's a great problem to have.”

Reviewing flights, destinations, and ways to get there Kelly's website stays in close touch with what his readers want. “I like the model that we have, I think our readers trust us. Our integrity is not up for sale.”

I'm fascinated to know how he plots an international trip so I ask him off the cuff to help me fund one to Tokyo, Japan. He doesn't flinch.

“Tokyo is an expensive city, with hotels and everything,” he explains. “The question is what do you want? Do you want to fly with hotels paid for, do you want to fly business class? Chase Points are really valuable because you can transfer them to Hyatt. I would try to get Chase Points so you can transfer them to United Airlines too and also ANA (All Nippon Airways). I highly recommend JAL (Japanese Airlines Company Limited) and ANA.

“With JAL, American Airlines miles work really well. But the thing is if you're searching forward availability won't show JAL flights. You have to use British Airways to sniff them out then call to book. I would get a Sapphire Reserve card. Being in New York I'm sure you dine out so you'd earn triple points with it. Between Chase Points and AA miles you could plan a gangbuster trip to Japan.”

This is the kind of advice that four million people a month line up for. It's made Kelly rich, but more importantly, it's helped him see the world. Doing what he loves to do and getting paid for it. No wonder he's always smiling in photographs.

*Originally published in 2017.