Bry Keith struggled with his sexuality growing up in a small town in Pennsylvania. He even dated a girl for many years. It was during a study-abroad program in Germany that he started to figure out his sexuality. “Germany, as a culture, is a little more open and accepting,” he says.
After graduating, Keith worked in corporate finance before he started professionally giving advice about loyalty points aka reward miles. A digital nomad who flies about 30 times a year, he’s channelled his expertise into BryGuides, a platform for coaching and consulting travellers into getting more bang for their buck out of their loyalty points. Turns out, most of us are doing it all wrong.
That means he’s a numbers guy, but he’s also got a saucy sense of humour, as those who follow Bry on TikTok and Instagram already know.
Although we know very well that Bry makes a living providing custom advice to subscribers about maximizing the benefits of rewards programs, we still tried to get some free tips out of him. And also find out about his favourite travels.
Right off the top, what’s the best points deal you ever scored for yourself?
My favourite redemption ever was flying Emirates first class to Bogotá for only 60,000 credit card points and $100 in fees. That was just a crazy great redemption. You’re sitting up front eating caviar, being served Dom Pérignon—it’s this amazing experience that you paid almost nothing for. I got my money’s worth out of the champagne alone.
And the best deal you’ve gotten for a client?
I helped a family of four save almost $30,000 on round-trip business-class flights from Austin, Texas, to Paris, France, using between 60,000 and 75,000 points for each person, each way. There was a better deal from New York, so I had them fly to New York for the direct business-class flight to Paris.
Beautiful. So when did you get obsessed with loyalty points?
Travel has been a key passion of mine. I was 18 years old when I had the opportunity to travel and study abroad in Germany. I remember the first time I walked around Munich. It was the night of a Champions League final. The city was electric. There were all of these people in the streets. I had been raised in the United States, where everything was car-based, and realized that there are ways you can build cities and structure reality that works better for people. I have held onto that passion throughout my life.
I started to get obsessed with credit card points and miles when I was living and working in corporate finance in New York. The hours were really intense and I still wanted to continue travelling. And life in New York was very expensive. I had to find a way to save on travel, because New York rent wasn’t getting any cheaper. I realized the key was in using credit card points and miles to save money and unlock perks. Once I started realizing the comfort you could travel in, flying first class or staying in five-star hotels, for a fraction of the list price, I started helping friends and family.
The turning point came when a group of friends and I wanted to go to Rio de Janeiro for Carnival, as well as Patagonia and a few other places. The flights were gonna be $2,000 each. People were saying they couldn’t go at that price. I remember saying, “Sorry guys, let me see if I can find a deal.” I found one and was like, “Does everyone have 40,000 credit card points?” Everybody did. We saved a lot of money. Then I was like, “What would you pay for a service like this?”
Of the people who I know who are obsessed with points, most of them are gay. Is there a connection?
One really cool thing about being gay is the opportunity to see the world a bit differently. Where other people think that you have to do things a particular way, we see opportunity. We’re more creative in how we think about things. And when you look at the statistics, LGBTQ2S+ folks tend to travel more than our hetero counterparts. We spend a lot of our time, effort, energy and, frankly, financial resources on this. So it’s an industry we’re really locked into, and any opportunity that we have to leverage the system and save on something, we’ll try it.
It doesn’t seem so complicated. You get a credit card with some kind of points. When you have enough, you go on their website and redeem them. What am I missing?
It varies depending on your specific travel needs and preferences. I think the majority of people make a mistake of just taking and redeeming their points in their credit card tool. While that is valid and works for many, depending on what card you have, your points can be worth more if you transfer them to external partners. On average I can get my clients five times the value with these strategies. It can also depend on where you live, what your hub airport is. If you say, “I only want to fly business class,” that’s going to change the strategy. If you want to travel to certain places a lot of times, there are other strategies. I’ll work with clients to tailor the strategy that’s right for them based on their needs. Some people don’t have a credit card that aligns with their home airport. Once you understand the landscape, you can have a better experience.
I know it’s hard to generalize, but is it better to use points on longer flights or shorter ones? Are some destinations a better value than others?
I actually find you get the best bang for your buck on long-haul international flights, especially if you fly business class. You can get better value for your points versus booking with cash. Usually for domestic travel, you’re getting a value of one to two cents per point. It’s tough to do better than that. If you take advantage of the right strategies, you can get 10, 12, 15 cents per point on long-haul international flights, but not by using the credit card tool.
There are certain places where it’s tougher to get really great deals. That is, anywhere that’s far from everything where there are not a lot of flights. Competition breeds competing on price. Somewhere like Australia, there aren’t so many direct flights because it’s just so far away from everything and there’s not so much competition.
What’s one thing I could be doing better with my points?
Earn as many points as you can in a transferable points currency, something with flexibility, that’s not tied to one airline. Then, it’s about not booking them in the credit card tool. That’s where working with an expert comes in.
Which destination would you love to see for yourself?
The number one location on my bucket list right now is New Zealand. I love a place that is naturally beautiful. I have a top-five list of places I’ve wanted to go, and I’ve crossed off four of them in the last year: Machu Picchu in Peru; Patagonia; Bali, Indonesia; and the Lofoten Islands in Norway.
How important is it for you that a destination has a gay culture—bars and the like—that you can experience?
My bucket-list destinations are based around nature, but any time I travel, I want to also spend time in a city and it’s important to me that wherever I go is gay friendly. When you look at my favourite four countries on Earth—Spain, Brazil, Thailand and Mexico—the reason why I love them is that they have vibrant cities with diverse and amazing queer communities.
Checked bags or no checked bags?
Never check a bag. I live my entire life out of a carry-on and a backpack. I try to go to only warm places, frankly, so I have the ability with my current lifestyle to simplify, to avoid bulky clothes. I know how to mix and match, rotate things in and out. I get teased by my friends, “Oh, Bryan is wearing that blue shirt again in his video!” Of course, I am. I’m living out of a carry-on.
This interview has been edited for length and clarity.
