Interview with The Points Guy founder Brian Kelly

The day has finally come — The Points Guy’s founder Brian Kelly has published his first book, “How to Win at Travel,” and it’s now available in bookstores and for online orders.

It seems hard to believe that this is Brian’s first book. After all, he’s been dispensing travel advice to the public for nearly 15 years, first as a lone blogger and then with a growing team of writers and editors, not to mention through social media and video.

In fact, I was one of the first members of that team — I became the first full-time employee of TPG’s writing staff and the site’s first managing editor when I joined in 2011.

It’s been over a decade since then, but like Brian, I am still maximizing my credit cards and traveling the world thanks to the points and miles I’ve accrued.

To celebrate the book release, I sat down with my old friend and talked to him about the path to this moment, how TPG has evolved over time from a one-man blog into one of the country’s leading travel publications, and some of the many changes we have seen both in the loyalty landscape and the travel industry in general since he launched the site. Note that the text has been edited for clarity.

Here’s what he had to say on those topics and more during our recent conversation, plus some details at the end about where you can catch him on his book tour and how to order a copy of “How to Win at Travel” for yourself.

An interview with The Points Guy founder Brian Kelly

Eric Rosen: Going back about 15 years to the start of The Points Guy when you and I met, you had started the blog and were booking award tickets for friends. Even back then, we were talking about a book, and now it’s finally coming out. Congratulations! But let’s start with the question I always ask about a story or idea: Why this book, and why now?

Brian Kelly: Eric, what a trip it has been. I am so proud of what TPG has become — it’s such a cultural centerpiece in the travel industry, and our work has impacted so many people, but I still say to myself that we have so much more work to do.

We have so many posts and articles, but the problem becomes that there is now so much information out there and the industry keeps changing dramatically — the average person simply can’t keep up with this cycle.

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It can be very intimidating popping into a blog post and trying to understand the foundation of what’s being talked about, and if you don’t understand a term or two, you might not feel like it’s meant for you.

Sort of like the beginners guide we have on the site, this book is like a curated version of what folks need to know about travel. I tried calculating it, and there are around 1,000 solid, in my opinion, money-saving trips in the book, so even if you absorb just a small percentage of them, your fluency will improve.

And it’s not just about points and miles; it’s a good primer about travel in general. There are a lot of different messages out there, on different sites, social media, mainstream media — it’s hard to know where to start, so I wanted to create a great resource that anyone can use to make the most of their travel.

And if you’re already an expert traveler like me, I found myself learning a lot even as I researched it, so I think there is something for everyone in it.

ER: As you mentioned, there’s so much to keep up with in terms of points and miles, so my next question is a two-parter. First, how do you explain to people why it’s even worth trying to keep up with all those changes? And second, what are some of the biggest loyalty trends that we’ve seen in all this time?

BK: It’s true, people have asked me, well, isn’t this book going to be outdated in a month?

And the answer is no because this book is not just a collection of the latest promotions. The reason it’s not called “How to Win at Points” is because this is really a travel book that teaches people the foundations of how to win at travel and about personal finance.

I talk about core principles like how transferring credit card points to airline and hotel partners can maximize your value, for instance. That lesson has not changed since 2010 and will be evergreen for years to come.

The point of the book is that points aren’t going away. They are extraordinarily valuable and are such a core part of profitability for the travel industry. If you’ve been ignoring them, you’ve basically been throwing away money, so consider this book an intervention.

ER: You’ve always said, since I’ve known you, in fact, that if you’re not earning points on pretty much every purchase possible, you are essentially throwing money away. On the flip side, what type of calculations do you do in your head to determine whether a specific redemption is a good value or whether you’d rather pay for a trip instead?

BK: Of course, it varies from program to program and card to card. But I have the Business Centurion Card from American Express, so I can essentially redeem the American Express Membership Rewards points I earn at a rate of 2 cents apiece for flights. So, my frequent flyer miles benchmark is around that value. If I’m not getting more than 2 cents per mile from a redemption, I just pay or use Amex points instead. Because hotel programs have devalued quite a lot over the past few years, I aim to get 1 cent or more in value per point, and if I can’t do that, I just pay.

ER: One of the other trends that we’ve talked about is the proliferation of new credit cards, points programs and perks over the years. So, folks need to remember that change isn’t always a bad thing.

BK: Absolutely. I think about, if it were 2010, and you showed me the current list of rewards credit cards from today and how many points you can earn for different spending categories, I would have probably fainted. Remember, back in 2010, certain cards like the Chase Sapphire Reserve didn’t exist. The Bilt Mastercard didn’t exist.

ER: Chase Ultimate Rewards had only just launched in 2009!

BK: That’s right, and they hadn’t even promoted it yet. I remember when I first started blogging, I had to Google “Ultimate Rewards” and then was incredulous that you could transfer those points to United Airlines and Hyatt. And that’s just one example. I really feel like from 2010 onward, this has sort of been a loyalty rocket ship taking off.

Of course, some pessimists say that it’s not like it used to be, and that’s true in terms of certain redemptions, but that’s only a third of the story because the level at which you earn is equally important, and then you get to the perks credit cards offer, which is the third facet, and they have gotten tremendously better than when I started The Points Guy.

ER: Before we turn to perks, you mentioned there have been major evolutions to the earning-redemption formula. Talk about those a bit.

BK: Sure, the dynamicness of awards these days is the biggest story. Back in the day, you could find 50,000-mile business-class tickets to Europe, but they were rare, they were static and once they were gone, they were gone. That boxed a lot of people out of the travel game.

These days, you see a lot of mid- and high-tier awards for flights and hotel stays where you are paying more in miles or points, but you can travel pretty much any day of the year. And we see airlines and hotels making seats and rooms available at a much more frequent (albeit more expensive) level.

That makes a huge difference for folks without a lot of flexibility in their travel schedule. And for those who do care to invest a little bit more time and are flexible, there are still some super-valuable redemptions to be had.

At its core, the point of the book is that a lot of people still have a 2010 mindset when it comes to their points strategy, but it’s 2025 and a whole new world with a lot more opportunities to earn across a lot more partners and spending categories, and I hope to inspire people to think a little differently about that as well.

ER: A lot of this book, and a lot of what we do every day on TPG, is helping people understand how points, miles and credit cards can make a difference to their personal strategy. You call this the “Platinum Age of Travel” in the book, saying it’s possible to travel to more places more safely and inexpensively than ever. How can someone think about their own personal strategy to travel the way they want?

BK: It starts with how you book travel. Airlines now, more than ever, are penalizing you for booking through online travel agencies, for instance, whether it’s fewer included benefits or less flexibility when things go wrong. To take another example, you might be using a credit card without travel protections, or if you do have a card with trip insurance, you might not know how to use it. But people need to lean on their credit cards and the perks side of things when things go wrong.

ER: As anyone who has gotten their rental car insured through a credit card when there’s been a ding or dent on the road knows, that can save you hundreds or even thousands of dollars. But it’s gotten a lot more complicated to keep track of credit card perks, and then also with some of the premium cards out there, some folks might not feel like they’re getting enough value to justify annual fees that can be nearly $1,000, especially if they’re waiting in line for airport lounge access, for instance. What are things issuers are doing or need to do to keep customers interested in their cards?

BK: American Express, for instance, is adding incremental perks and discounts. For me, as a busy dad and person in general, it’s a lot to keep track of getting all your credits. However, for people who do have the time, those benefits can be worth thousands of dollars each year.

Or, consider the Chase Sapphire Reserve, for example; yes, its annual fee is $550, but you’re getting $300 a year off the bat in travel statement credits.

The Delta SkyMiles Reserve American Express Card comes with an annual companion certificate for a round-trip domestic ticket, and you can even use it for first-class tickets, so that could be well over $1,000 in value right there.

Or, maybe you travel a lot and your card gets you into your preferred airline’s lounge so you can have a place to work and get a meal. That’s real dollar value right there. So don’t just look at the sticker price of the annual fee. Really add up all the tangible and intangible perks you might get from a card and decide whether it’s worthwhile for your needs because other cards might be cheaper, but if they don’t come with those money- or time-saving perks or comprehensive travel protections, they can end up costing you more in the long run.

ER: One of the other things you say in the book is that loyalty programs, and travel in general, is kind of like a sport where practice makes perfect. You’ve got to keep brushing up on your skills and putting them to use. So, what are some of the skills that you, Brian Kelly, The Points Guy, use when it comes to travel every day? And what are some that other folks should undertake on a regular basis?

BK: I think it helps a lot to understand even just a little about how the travel industry works and what you might be entitled to or what you can ask for in case your trip plans go wrong, whether it’s because of a winter storm or unforeseen circumstances. Just knowing those things and knowing how your credit card can help with trip delay insurance or lost luggage insurance can help tremendously.

One of my other favorite tips is an acronym: HUCA, which stands for “hang up, call again.” If you get an agent at an airline or hotel who can’t help you find that award redemption or who isn’t able to rebook you for a legitimate reason, just hang up and call back. You might get someone with a lot more experience the next time.

And, above all, remember that airline agents, front desk reps and folks like that are all frontline employees. They don’t want you to have a bad trip, so think about how you treat them. You won’t get anywhere by throwing a fit or screaming at anyone.

ER: Like we always say, you’re your own best advocate, and being armed with information is the greatest tool in your arsenal. I’m also surprised you didn’t say this because it’s something that you’ve said since I’ve known you, Brian, which is just to ask nicely. It can get you so far.

BK: I was dancing around that, but it’s so true. Even back in the days when I was broke and trying to fly places as cheaply as possible, I remember getting upgrades as a lowly Delta Silver Medallion just by sweet-talking gate agents. So, it never hurts to ask nicely!

One of the other skills I encourage people to practice is using all the new award tools out there, like Point.me and Seats.aero. It can take some time to master them, but they allow me to search for award availability on various routes over the course of a year in one fell swoop, and that saves me a ton of time. So, as the book will teach you, it’s worth paying for some tools like those because they can save you hundreds or thousands of dollars a year.

ER: There are only so many credit cards out there and only so many loyalty programs to toggle between. How do you keep your points and miles strategy fresh?

BK: For me, it’s about maximizing my spending since, for better or worse, I have to spend a lot these days, whether it’s for business spend or expenses for a growing family.

I put a simple strategy in place to try to earn the most points or miles in the major categories I spend in. For instance, I use my American Express Gold Card to earn 4 points per dollar spent on grocery orders. Or, we spend a lot on Amazon for convenience, so we use that cobranded card for cash back. For nonbonus categories, I put everything on my Capital One Venture X Rewards Credit Card since it earns 2 miles per dollar spent on every purchase, and I don’t have to think about it.

ER: That’s so relatable … so let’s make you even more relatable, Brian! What are some of the biggest points and miles mistakes you’ve ever made?

BK: I’m just like everyone else! I make mistakes all the time. I’ve had miles expire, and I’ve made the wrong transfers at the wrong time. I haven’t read some very specific program rules, so I didn’t realize I couldn’t book an award ticket for someone who wasn’t a family member with a certain airline, or I didn’t know I couldn’t change an award ticket with another airline’s partner once it was booked. It’s a minefield!

ER: Speaking of booking tickets for others, you’ve gotten a lot more practice doing that lately it seems, since you’ve just had your second child. Congratulations, by the way!

BK: Thank you!

ER: So now you’re a family man and a family traveler. How has that changed both the way you travel in general and also the way you’ve been thinking about points and miles?

BK: The rules around what kinds of car seats you can bring on board in different countries are wild, and traveling with a lap infant has certainly been a learning curve (and expensive at times).

ER: Oh, we have so many articles on this because it can be so complicated.

BK: But no, I’m really proud of the family travel chapter in this book. I dedicated the book to my son, Dean, and it has given me so much more vigor to travel and see the world through his eyes. And travel with small children doesn’t have to be scary. Even long flights will be over before you know it, and a lot of destinations are very family-friendly — for instance, we’ve been pulled out of long airport lines in Portugal and allowed to pass through more quickly.

ER: What lessons do you hope that travel instills in your children? You’re obviously giving them some extraordinary experiences. What do you hope they take away from them?

BK: I want my kids to grow up meeting people of all different types and being compassionate and curious about the world. I want them to try new foods, experience new cultures and build a foundational outlook that the world is inherently a good place. After all, travel has changed me for the better. So, I hope that they are explorers, that they are inquisitive and that they will be a net positive for society.

ER: Let’s end with a look back. If I can just rewind for a second and take us on a little stroll down memory lane: It’s the spring of 2011. You’re still working at Morgan Stanley but you’ve been blogging for a while and booking award tickets for friends and family. At a certain point, you decide to make The Points Guy your full-time career. What was going through your mind at the time, and could you picture what TPG has become 15 years later?

BK: I remember at the time I knew how much joy I got from helping people, and I still feel as passionate about that as I did back then — it brings me such extraordinary joy, and I love hearing from our readers every single day about differences our content has made in their lives. I am so proud of what the brand has become.

Did I ever think that we would get to this level? No. But it has been an extraordinary journey. I’m excited to see where TPG goes from here with really talented people like yourself who help the brand keep reaching new heights. It’s just such an honor to still be part of the journey.

For those of you interested in picking up a copy of “How to Win at Travel,” you can purchase the hardcover on Amazon.

Upcoming book tour dates, including those in New York, Chicago, Coral Gables, Florida, and Los Angeles (100% of the proceeds from this particular even will be donated to the Los Angeles Fire Department) have sold out already, but there are more cities and dates to come, so be sure to check the tour website for a chance to meet Brian and have your book signed.