How did you become interested in travel?

I’ve loved flying since I can remember and was always happy to be getting on a plane. My dad was a big business traveler and he was always jetting off somewhere, so that also glamorized a travel lifestyle in my mind and even as a kid, it was a big part of who I wanted to be. In fact, my dad wasn’t very savvy with computers and when he traveled, he would pay me (my allowance) to book it for him and I started keeping track of all his miles for him.

I signed him up for all the frequent flyer programs. One day, my dad was talking about summer vacations and maybe going to Florida. I said, "I think we have enough miles to go to the Caribbean." I'm one of four kids, and we went to Grand Cayman for the first time, and we were basically going there for a lot less than it would have cost if we'd gone to Florida. That kind of cemented my awareness of loyalty programs.

"There are a lot of different kinds of points programs out there – fixed-value like Capital One, co-branded like frequent flyer miles, and transferable points like Amex Membership Rewards or Chase Ultimate  Rewards, which you can transfer to a number of hotel, airline and other partner programs."

What was the first time you used a loyalty and rewards program to further your travel?

When I was thirteen, my dad was talking about taking the family on a summer vacation to Florida, but I said that he had enough miles to get us to the Caribbean. It’s a testament to my parents’ trust and love that they gave me free rein to try booking a trip. There are four kids in my family, so six of us altogether, and I was able to book us all a trip to Grand Cayman that summer for a lot less than it would have cost if we’d gone to Florida. My family was thrilled, and I was hooked on points and miles. 

What are the top three things travelers should look for when choosing a loyalty program?

Flexibility and lots of redemption options. There are a lot of different kinds of points programs out there – fixed-value like Capital One, co-branded like frequent flyer miles, and transferable points like Amex Membership Rewards or Chase Ultimate  Rewards, which you can transfer to a number of hotel, airline and other partner programs. Transferable points are the most dynamic and valuable out there thanks to the flexibility they give you to top up this account or that one when you need a specific redemption, and they should be a part of any savvy traveler’s points strategy.

Lucrative earning and redeeming opportunities. When looking around at loyalty programs, you’ve got to look at both the earning and redeeming side of the equation. By that, I mean that you should pick programs where you can rack up points easily and quickly – through travel, credit cards and other earning partners – as well as being able to redeem them when you want for the travel you want (within reason). The best loyalty programs offer you great opportunities and value propositions on both sides of that equation.

A program that offers perks as well, whether that’s the opportunity to attain elite status, value-added benefits like inexpensive ways to upgrade or just get better seats in economy based on what your needs are. Whatever program(s) you join should offer their loyal members extra perks and benefits that make sticking with them worth it.

Can you tell us about your best travel ‘deal’? How did you secure this deal?

This past November, I got to travel to the Maldives, one of my all-time top dream destinations. I’ve become a big scuba enthusiast lately and the Maldives is one of the top spots on earth to go diving. It’s also one of the most remote. However, with a  little careful planning, I was able to redeem 60,000 United miles and $20 in taxes and fees to fly business class from New York to Taipei on EVA then to Singapore and on to the Maldives in Singapore business class. When I got there, I was able to stay several nights at the Conrad Maldives for free using Hilton points, and I got to spend my money enjoying the diving (and a few nice meals!).

 

What are the top 3 destinations you’ve seen by cashing in your points?

The Maldives for sure, as I mentioned above. It’s like nowhere else on earth, and you feel like you’re at the end of the world when you’re there. On my way back to the states, I stopped in India for several days and relaxed on the beach in Goa then spent a few days in Mumbai. It was incredible, even just scratching the surface like that.

"We’re moving away from frequent flyer and guest programs to frequent spenders. These programs are incredibly lucrative for credit card companies, so we will see more partnerships and integration between airline and hotel programs and credit cards."

I have also traveled to South Africa twice in the past year, and I absolutely love it. The first time, I used US Airways miles to book a roundtrip business class itinerary from New York to Cape Town on South African Airways and had a great time in Cape Town, out in the Cape Wine Lands and along the coast, and then up in Kruger National park on safari. The second time, I actually booked a paid ticket, but had to return early for a family emergency and used my Delta miles to book a last-minute return flight from Cape Town to New York on KLM via Amsterdam.

I also recently had the opportunity to visit Australia for the first time and used US Airways miles to fly from Los Angeles to Melbourne via Sydney in United first class and I actually had to postpone the return due to a work commitment, so I’ll be using that later this year to check out Thai Airways first class from Bangkok to Zurich then on to New York from there – essentially turning my award into a round-the-world ticket. Australia was amazing – the food and wine scene in Melbourne, scuba diving on the Great Barrier Reef off Hamilton Island, and finally getting to experience the energy and beauty of Sydney. It was a great first taste of the land down under.

How has the travel rewards industry changed during your experience as ‘The Points Guy’?

More and more people are smartening up and realizing that  these programs offer huge value. Credit card companies are taking note and offering more products than ever. We’ve seen some airlines, hotels and credit cards devalue their programs – meaning it takes more miles to get the same awards. This isn’t the end of the world, because earning miles through non-travel like credit card sign-ups is as lucrative as ever. As long as you’re earning more miles than they’re inflating, you’re still ahead of the game.

What do you think the next big trend is within the industry?

We’re moving away from frequent flyer and guest programs to frequent spenders. These programs are incredibly lucrative for credit card companies, so we will see more partnerships and integration between airline and hotel programs and credit cards. Hopefully that will mean more ways to rack up tons of points and redeem them for great travel awards.