Totally Booked: LIVE! In this special episode of the podcast (in-person at the Whitby Hotel with a live audience!), Zibby chats with Brian Kelly, better known as The Points Guy, about HOW TO WIN AT TRAVEL. Brian shares his journey from tech-savvy teen booking family vacations to building a travel empire that helps millions maximize their points and miles. Whether you're a frequent flyer or a credit card newbie, Brian’s insights—from choosing the right cards to turning miles into five-star travel—are packed with practical tips, fascinating anecdotes, and the infectious thrill of gaming the system.

Transcript:

Zibby: Welcome back to Totally Booked with Zibby. I am so excited to be here with Brian Kelly today, the points guy to talk about how to win at travel.

So exciting. Congratulations. 

Brian: Thank you so much. 

Zibby: Oh my gosh. I have so many questions. I travel all the time and this is on my mind constantly in every way, shape or form. But first, how did you become the Points guy starting the whole company? Take us back. I know you write about in the book, but 

Brian: Yeah. Before I was the Points guy, I was the points kid.

So in the nineties I was just that, 11-year-old who was on the internet. My parents knew nothing about technology and I became the kind of computer genius of the family. I was on AOL those days when you used to have to put a modem in a computer and a phone line. The kids these days have no idea what we went through to get on the internet.

Zibby: They don't, they have no respect. 

Brian: And long story short, my dad, I grew up outside of Philadelphia, he ended up getting a job for a startup outside of in Chatsworth, California. So he was going back and forth La Philly Road Warrior Travel, and one day he came to me and said, I have all these frequent flyer miles.

I have no idea how to use them. I'm too busy, but I guess he just, his 12-year-old son who knew everything. Technology was like, if anyone can figure it out, it's Brian. And that's a tip I give a lot of parents these days. Maybe not plan the entire trip to young kids, but giving them a portion of the trip to plan itinerary.

I think so many of the skills around travel and planning, good trips and research are great for kids. So I took that and ran with it and I booked, I'm one of four kids. I booked our family of six. We went to the Cayman Islands for free. And I just remember thinking, how incredible is this? My dad had to miss so many basketball games, but every year on his points, our family of six took this epic trip to the Caribbean.

So that's where I got my stripes in the in points. Never in a million years did I think many years later I would turn this into my business.

Zibby: But it was all because of your dad's pride in you being the original points guy, like pride in you. Did it look at this trip? 

Brian: Oh, he loves coming to the book events.

He will tell people that he's the original points guy. But yeah, so that's where I learned the basics. And then in 2007, after I graduated college, I ended up getting a job at Morgan Stanley where I was basically my dad. I was traveling nonstop. I learned very quickly how to maximize my corporate card.

Choose the, I was Delta. I was Diamond when they first came out with that. And that was interesting time because during the Great Recession, I luckily had a job that I was still traveling and most, business travel went off a cliff. I all of a sudden had super elite status, and the airlines and the hotels were giving out tons of free flights.

But interestingly, because I, I had all this business travel, but they weren't, I wasn't getting paid money because I was in HR for a bank in 2008, and every year the banks were like, congratulations, your bonus is not getting laid off. Come back again next year. So I'm in my twenties, but I had all these miles.

So it was a really interesting time in my life. I was living a double life 'cause I had so many frequent flyer miles, elite status. I was leaving on the weekends to fly, to stay in hotels where I would get the penthouse suite. So I'm in my twenties. I'm broke, but my points it was cheaper for me to fly first class to London for a weekend where my breakfast and afternoon lounge at the hotel would get most of my meals and on the plane than it would be for me to stay in New York and have that dreaded, going out to dinner with friends where everyone splits the bill and I'm like really running tight.

So I was points rich, cash poor. And finally in, in 2010, my ex at the time was like, you're a genius with this point stuff. You should start a business on it. So the Points guy started in 2010, and originally it wasn't even a blog, it was just, I was a travel agent for points. So I would work at Morgan Stanley, come home and as the points guy I would charge you $50 a ticket.

So people like you would come to me and say, I am busy. I have all these Amex points. I wanna take my family to Italy. But when I go on Delta's website, it says nothing available. And in 2010, that was the years of, it was feast or famine. So nope, it was blackout dates. So you really had to be an expert.

There were all these super expert tools that I knew, so I would, that was my side hustle. I would come home book people trips and for me, and to this day, booking award trips it's a crossword puzzle. It's like doing the crossword and it, the satisfaction you get. When you can beat an airline, like the airline beating the airlines at their own game is just so joyful.

When they, give us fees nonstop and change fees, but like when you can use their program against them. So that's how the points guy started. And then a friend quickly told me this. He's this is 2010. He's I beg you to start a blog. He, this is when travel or fashion bloggers were starting to sit front row at fashion shows.

It was this, I didn't know it at the time. I could sense there was something changing in media. But the way my friend looked at me, he was a very smart friend, he goes, I urge you blog every day. The same time and you will build the audience because, and it was true everywhere I went, people would be like, I have points.

I don't know how to use them. So there were plenty of other points bloggers out there. People think I'm like the first one to make this mainstream, but it was true. June of 2010, 

Zibby: You were just the best. 

Brian: Yeah. There are plenty of smarter people out there. But what I learned to do very quickly is leverage media.

So the New York Times had reached out to me, 'cause the common media narrative in 2010 was, points are useless, blackout dates, you can't go anywhere. And there was huge frustration. And so I was the voice saying, okay, in the media, stop writing these articles that are just points are useless.

What if they're not? But, and I told you how. So the New York Times wrote a piece about the Points guy in 20, early 2011, and that, that post changed my life because unbeknownst to me that New York Times link to a, up and coming little blog just shot me into stardom in, in the sense that Google's main, in 2011 the algorithm if a blog had a link from the New York Times, it meant, so all of a sudden my traffic just went through the roof and at the same time the credit card company started approaching me because I knew their products as a road warrior in and out. So when I.

Authentically talked about the Delta credit card you need to have for the companion ticket, and I'm using this companion ticket to fly to Hawaii. First class was much more effective than them running a full page ad in the Wall Street Journal on just the credit card ad. So this was the new age of affiliate marketing, which most media publishers, it felt a little spammy at the time.

All the major travel pubs, they had huge traffic. So it was all display ads, but. I came in and started a business around, I had a smaller audience, but very engaged and I figured out very quickly that in the media I could be a new voice for, this counter narrative and it's pro-consumer.

At the end of the day, I, to this day and why I wrote this book is there's still so many people leaving money on the table and points and miles, this whole loyalty ecosystem. It is the future. If you look through the pandemic, every single airline exists today because they leverage their loyalty programs to sell billions of dollars worth of miles to the credit card companies.

These credit cards are not going away. In fact, especially with the softening economy, now the airlines more than ever are doubling down on loyalty. So my, if there's one message you get from the book, it's. There's never been a better time. Get in now. Stop the narrative in your head that this game is over.

'cause a lot of people think, oh, it's everyone's doing it now. Therefore, I missed the boat. And that couldn't be further from the truth.

Zibby: You are so impressive. I want you to come in and help me with the book industry, if you don't mind, during your spare time. You can, can.. 

Brian: I have learned a lot about the book industry.

Zibby: I bet. We need to have a good meeting. 

Brian: As a data and analytics person every day. Yeah. It's very interesting the the pipes or lack thereof in the industry to, to get realtime signals, but I am happy to see book events. I, from what I hear, books are back and it was so cool to be able to go to so many independent shops like yours.

And Santa Monica and having standing room only crowds. So kudos to you for creating a really special community. 

Zibby: Oh, thank you. That's so nice. Okay, points. So do I need the Delta credit card? 

Brian: Credit cards are the foundation of any good point strategy and there are like three simple flavors of credit card.

The one that you everyone needs is a transferable points credit card. So that's not a Delta credit card. 'cause when you use a Delta credit card, you're earning only in Delta miles. Whereas with these transferable points credit cards, this is the Amex Gold card. The Amex Gold card gives, for example, four points per dollar on all dining and groceries.

And those are two categories. We all spend a lot of money. And the beauty of getting an Amex point is that you can transfer to Delta one-to-one as if you had used a Delta card or 32 other partners. So when you have these bank points that allow you to transfer to a number of carriers, it gives you so much more flexibility.

'cause while Delta's great. Say you want to fly air, not Air France 'cause they're partners, but Air France actually, you could transfer Amex points to Air France and fly the same flight that you would fly with Delta for 50,000 points. Whereas Delta now charges 350,000 to go to Europe.

So one seventh the price for the same exact flight just by using different loyalty programs. I know it sounds confusing, or if you want to ever fly the Emirates, A380 with the shower in the sky, you can transfer Amex points to Emirates and all these different partners. So in order to get the most value outta your points these days, you need to have a, a diversified currency.

So that's Amex membership rewards, Chase ultimate Rewards the Chase Sapphire preferred. And reserve cards are amazing. Capital One, venture X, that's two points on every dollar you spend. Now, I'm not saying you shouldn't have a Delta Amex. There are the airline co-brands, the hotel co-brands, and these cards are good, not really for points, because you're earning one simple currency.

And as much as I love Delta miles, just keep going down in value because every month, they're increasing the amount of miles you need to go anywhere. But they do have really valuable perks. So I have co-brand cards, but I, they're not my workhorse cards that I'm spending most on every day. The free check bags, the lounge access perks, like that can absolutely make sense on spending on those Delta cards.

But in the book, I teach people the overall economics. And you should understand as a consumer, there's an opportunity cost. So some Delta Flyers may say to me, Brian, I understand I could be earning way more valuable chase points, but by spending on a Delta card, I'm able to just barely get diamond status and that diamond opens up $10,000 a year in value. 'Cause I get to use those upgrades. To upgrade to Europe or Tahiti, which is fine, but I, what I want everyone to do is there's no one size fits all answer. And I want people to understand the value of the perks they're getting and understand that if you're gonna get perks from a hotel credit card, just make sure that they outweigh the value of the points you could have had.

By using much better cards for points earning and in general you should probably have a couple different credit cards. I know people, this is where people start to get uncomfortable. I have 28 credit cards in a near perfect over 800 credit score. And this is the beauty of this game and the US is the global epicenter for points and credit cards.

This is what I wanna let people know that we are living. If you talk to any of your friends in any other countries, they are jealous 'cause they only have a handful of points, cards, and. In the US we've got probably 25 amazing credit cards, and the joy of it is you can get signup bonuses for a credit card that are worth well over a thousand dollars, especially if you're married.

I, we call this two player mode. Don't just have one person getting a credit card. But the biggest thing is your credit score goes up, and I talk about this a lot in the book, and this is the joy of the Points game is when you play this smartly and you have to pay your credit cards off in full every month to avoid the interest.

If you're paying interest on your cards, you're losing at the points game. But if you know how to budget your money, you put point, purchase on a credit card, you get the points, you pay it off, you avoid the interest. And FICO, the number two factors of your credit score are paying your bills on time.

So just make sure you pay them on time, which and your available credit to debt ratio. This is your utilization score. So the more credit cards you have open, the more available credit you have and you're not using it 'cause you're being very responsible and paying it off in full, your score goes up. So this is the joy of the points game for consumers, especially consumers who you know, in this time of inflation, we're finding it hard to make ends meet to do that family trip. You can get credit cards, get the huge signup bonus, and then start earning points on category bonuses. 'cause a lot of these credit cards will get four x here and your credit score goes up. So when you want to get a mortgage, your actual mortgage rates go down. So I have this saying like, winning at travel, winning at points is winning at life.

'cause I firmly believe it engages you in our financial system. It gives you that mentality of understanding how the system works and how to get your fair share out of it. 

Zibby: Is there an actual points game? Is there a board game or a computing? 

Brian: There should be. 

Zibby: Why is there not? 

Brian: Yeah. Because the game itself is the game, like people, it is, just understanding and.. 

Zibby: But the game that you are playing Yeah.

Is at a level that like, I'm like, I'm following, and I, what if there was just a game? That was like really easy. 

Brian: That's good to just to get people used to it. Like a monopoly of points. Yeah. That's a good idea. That's as writing and promoting a book as a full-time job.

Zibby: Yes. 

Brian: So once this is fully done, then I'm gonna, I'm gonna create the game. But it's, this is a game. Like I joke that this is like crossed, some people have cross words and I love the New York Times games every morning. That's my ritual to do my. But the beauty of the Points game is your prize isn't just like bragging to your family friend group on text that you got Wordle in three or two.

The winning at the points game is saying, I'm going to Florence, and it was $29 in business class. And that's what I just tell people is that endorphin rush you get when you finally crack it, you know the code. And it's not always just first class trips to Italy. I want everyone to understand points are an insurance policy when you have a bunch of points, because one of the best things that come out of the pandemic is that the airlines now let you, every, all the major US airlines, you can cancel your points, reservations up until departure for free, and you get all your points back.

And so follow me here. You're at the airport, you're flying an airline, and all of a sudden you're delayed. I talk about, I have a whole chapter on when things go wrong. I want people to think. When I, you have points and a big points currency, and you've really gotta get. To Salt Lake to see family and, there's a flight on another carrier.

What I do is I instantly will just check to see what other flights on other carriers later that day and I book it just so I have peace of mind that I'm getting to Salt Lake today. 'cause I need to be at that event. If your flight goes out on time, you can just click one button in the app, you cancel and get your points of miles back.

But this is why people expect the airlines to take care of you and you're gonna wait in an hour long line, you're gonna get a surly agent who's no, you can fly standby tomorrow. And you're like no. That's not how it's gonna work. But instead of fighting with that agent, you have to become your own best advocate.

And when you have points, and when you're on a family trip in Europe and you get a call that a family member's sick and you need to come back to the us, if you call the airline on a paid ticket, they're gonna fleece you. They're gonna charge you. $5,000 a ticket to get that last minute trip. But what people don't know is that airlines are also releasing tons of first class award tickets at the lowest levels last minute.

Procrastinating. Last minute bookings are some of the best times to use points to get home. And so if you ever have to come home or you want to come home early, you really miss your kids. You call the airline to change your ticket and they're gonna be like, it's gonna be $6,000 a person. You're like, okay, I don't really wanna get home that much.

But when you use points, you go on the app and you'll say 60,000 points to fly Swiss Air business class done. Points and when you get this world, it will, it'll change your mentality and give you more confidence in traveling because the feeling of without breaking the bank or spending a fortune I can get anywhere I need in the world or fly my family members here on a minute's notice without it throwing my budget for the year outta whack is pretty incredible. 

Zibby: I am just always afraid that if I spend them, there'll be a time where I really need them later. 

Brian: Yeah. So that's a part of our points hoarding epidemic. And I'm sure there are some points hoarders here. I'm a points hoarder. Yeah. So I can see you.

Yeah. 

Zibby: Okay. Hoarder. Yeah. 

Brian: Look, I get that. It feels good to see these big balances, but there is a downside to that FOMO of a later deal because in general, as I mentioned, these frequent flyer programs, I want everyone to understand like there's airlines these days are essentially loyalty programs that have some planes that fly.

Airlines make way more money printing these frequent flyer miles and selling them to banks than they do actually flying planes. Almost every airline in America would be unprofitable if it were not for their loyalty and their credit card program. Delta leads the pack. 1% of total US GDP goes on a Delta Amex card.

But what does that mean? That means every single day, billions of new delta miles are being printed by everyone using their credit cards. Delta it doesn't have that many more planes. They actually can't get enough planes. So the capacity on flights is staying the same, but so many more miles are being, since the start of this podcast, billions, more miles.

So how does Delta, and it's a brilliant business model, Delta can click a computer and say, okay, that flight from LA to JFK, that used to be 40,000 miles. It is now 50. So that overnight, they're what call devaluations, where the airlines just keep increasing the amount. So for all of you who are holding points for a future date, just understand this would be like putting your retirement funds in a checking account.

You would lose all day, every day to inflation if you did that. So by just letting your miles sit there in accounts that don't earn interest and that are being devalued every day, you're doing yourself a disservice. So that's not to say go out and just, burn them on gift cards or something. Put them to use.

Take the money off the table today, even if it's for domestic tickets for your kids or whatever. Instead of spending this 600 bucks or whatever, just take that money today. Think about that money saved. You could put it in investment account, but it is a losing proposition over time to save them for an unknown future use.

Zibby: Okay. Why are you not like the CEO of United? 

Brian: That would be no fun. I much prefer people are always like, why do you want to become a pilot? I'm like, no. I like drinking champagne in the life. Flat bed. Like I couldn't drink champagne and enjoy myself. I, I. Love working for consumers like, and I have the best job in the world.

I truly like when I get to walk through the airport and people come up to me and their eyes light up because I'm teaching people how to get value that's in front of them today. And there's no greater joy when it clicks with people. And that's why I wrote this book. The Points Guy started 15 years ago, actually this week.

And we have so many blog posts over time and it's really confusing. So to me, this book is like the on-ramp for everyday people. Like you can't have an excuse. I made it pretty simple. It can still get a little complex in the book, but what I tell you about this, like with anything financial, you can't just Google what's the best mortgage for me right now, just give it to me.

I don't wanna do any research, right? Like we all have to do a little bit of. Taking time to understand these systems and how to get the most out of us. There is no best one mortgage for everyone. 'cause it depends on where you live and your credit. And that's the same for the Points world.

But once you get it, and then once you start flying, and I will warn everyone listening, the points will allow you to start flying business class when. You might not otherwise be able to afford it, but I will warn you now, once you start turning left on a plane, it is very hard to go back. So if you fly economy today and you're like this, I'm fine with it.

Stay there. 

Zibby: Yeah. Because the seats for us. 

Brian: Yeah. No, but and, yeah, so I love being in this in-between, of being able to like, help consumers navigate this crazy, constantly changing space and, yeah, no, I wouldn't wanna work for an airline. 

Zibby: Okay, great. All right. You keep doing you. Brian, thank you so much.

Thank you for all you do to help all the rest of us live better lives. 

Brian: Thank you so much for having me. 

Zibby: Thank you.