Meeting Brian Kelly, The Points Guy
Meeting my Heroes is an occasional essay series from Matt Carmichael.
I suppose I could have been The Points Guy. It’s the funny thing about getting into something before the internet really existed. Sometimes I forget to go back now that there is an internet and do the internet things. But when do you, you often discover that there is a community around something you thought was just a thing you did on your own? That was true with Taylor Welden and Carryology and it’s true with The Points Guy.
Like wait, there’s advice? There’s a subculture? There’s a fandom? Who knew!
It’s a weird generational thing I think.
But back in the 1990s I started earning frequent flier miles from credit cards. At that time, and man I feel old having to explain this, you could also get points from your long distance telephone service. They had sign-up bonuses just like the credit cards. Changing your long distance service wasn’t that hard or inconvenient, like changing your cell provider is now. And I had two phone lines at my apartment. On one I actually made calls so I cared about long distance pricing on that and would try to find the cheapest provider. But I also had a line for my modem and never called long distance on that. So I’d flip the service every six months and get a new sign-up bonus. Which meant as a 20something I flew to Europe First Class, for free. And I was hooked.
Again, it didn’t occur to me that anyone else might care about this. But I was wrong.
Now, of course, fandom is everywhere on the internet. Connecting communities large and small. There are good things about that, and also darker things like disinformation. And for every harmless or helpful community, there seem to be dozens of groups of people you hope would never find each other and organize and support.
But I’ve both participated in, and built communities (Prodigy message boards, usenet groups, listservs and more) since the early days. I just didn’t always go looking for them for everything.
Brian Kelly built a hobby of collecting travel loyalty points into a blog and then into a juggernaut. His site, The Points Guy, is a content machine and community wrapped into one neatly referral-linked package.
I knew I wanted to interview him for WTF so I did what I often do: I reached out, did some favors, made some friends by giving interesting people interesting challenges (in this case, some polls we did together). And eventually worked my way up to interviewing Brian himself.
And then I did the other thing I like doing, after an interview that was done via Zoom, I went out to meet him in person, too.
He was speaking at the Travel and Adventure show, a trade show in Rosemont where destinations come and try to convince you to spend your vacation dollars with them. You can learn about everywhere from the Bourbon Trail, to Alaskan rail adventures to Costa Rica rain forests. And they have speakers. That’s how we met Rick Steves, too.
Brian told the story of how he got his start and offered tips for travelers and other points collectors. During the Q&A I drifted over to the table where he was going to be signing autographs. Conveniently, I could still listen to the Q&A while also jumping the queue.
Brian seemed kind of new to doing public appearances like that. He didn’t have a book, or anything obvious to sign. I had him sign my Admirals Club card, which seemed as appropriate as anything. I thanked him for the interview and told him it was nice to meet in person and suggested a couple of other things we could work on in the future.
He hung out until he’d signed everything for everyone and we got a family pic, too.
Here’s what I wrote in What the Future’s Vacation issue:
Brian Kelly a unique perspective on the lucrative intersection of travel and financial services. When he thinks What the Future, he’s thinking about how shifts in ways we pay for travel will shape how we travel.
Matt Carmichael: 2020 was a big year of change in how we traveled. What changes do you think will stick?
Brian Kelly: The notion of only getting two weeks of vacation a year to go somewhere has now changed. Many more people are working from home and are thus able to travel longer, combining work with the vacation. Even for myself, The Points Guy is much more digital, which allows for a lot of different ways to travel without having to worry about vacation days.
Carmichael: Do business travelers who are on the road all the time, vacation differently than others?
Kelly: Yes. Business travelers who have huge points balances and elite status wrapped up with their loyal hotel chains tend to redeem those points for amazing trips with their families. I was on the road all the time and was frankly burned out. So, I have actually been able to reset and travel much more methodically and meaningfully, and I anticipate that will be the same for a lot of other people. Instead of doing a trip to the office for face time, I think there will be larger and longer meetups, creative strategy sessions, etc.
Carmichael: How do you think the no- longer-road-warriors will change their personal travel habits once they start losing status and those big banks of points you were talking about?
Kelly: For the next couple of years, the culling of the herd will happen. It is a good time for frequent flyers. You can get top-tier elite status cheaper than ever before. For elite travelers, there are a lot of treasures out there for those willing to make the trek.
Carmichael: We asked people in a survey about their dream destinations and Europe narrowly edged out staying here in the U.S. Do you think that dream destinations for people have started to shift?
Kelly: It depends on the segment of the population. I think there’s a lot of fear with leaving the country—if you get sick abroad, new testing procedures for coming back into the U.S. In 2021, most people want to just get to a beach and get the heck out of their house or go on a road trip.
Carmichael: Do you see that type of vacation and the format of vacation changing too?
Kelly: No, I think the summer of 2021 will look similar to 2020, but with more people going on those trips now that they’re pretty confident that these vaccines are very effective.
Carmichael: How are people spending on vacations and budgeting for vacations? United States Australia / Pacific Islands South/Central America Asia Canada Mexico Africa Arctic/Antarctic Middle East Other Don't know
Kelly: The positive side of the pandemic is a lot of people have saved up and paid off their credit cards and are willing to splurge for the nicer room. It’s like, “I haven’t taken a vacation in a long time,” so it’s revenge travel.
Carmichael: It was a big year for the points economy shifting from travel rewards and perks to credits and points multipliers for food delivery, groceries and streaming services. Will we continue to see a flexible future in terms of how people gain the rewards?
Kelly: Flexibility is key. Perks like lounge access are not enough to keep people paying hefty fees on premium credit cards. I hope the industry continues to make their travel points more flexible in terms of valuable redemptions that are not flights or hotels. I’d like to see the credit card industry partner more with travel insurance products that give consumers peace of mind to get out and travel again.
Carmichael: Do you think there’s going to be a big points spending boom or will it in the end be harder to redeem because of that?
Kelly: In the short term, there’s amazing award availability. As people get vaccinated and are more comfortable and countries open up, we’re going to see a boom. That’s why getting ahead and booking flights for the future now will lock your travel in at the best rates
Carmichael: This also was a transitional year for vacation rentals. Will they get into the points and loyalty game more?
Kelly: I could see more partnerships with the credit card points being able to redeem for Airbnb, etc. But I don’t anticipate any big news in 2021.
Carmichael: How does the travel industry survive this decline in business travel, which has always propped up the airplane and hotel economy?
Kelly: Traditional airline pricing is crazy, where last-minute, one-way travel costs $20,000. They had those rules to gouge business travelers, and they made a lot of money doing that. Consumers will benefit as airlines try to get more value out of those middle-of-the-road travelers— people who want to splurge—and get away from gouging.
Carmichael: And the points game will survive, too?
Kelly: Airlines are going to survive because they sold billions of dollars’ worth of frequent flyer miles to the credit cards. Loyalty programs are more important than ever. They literally help the airlines survive. A lot of airlines make more money from their loyalty program than they do flying planes. But there are only so many flights you can offer. We’ll see more ways to use points for more parts of the travel experience.