By Andy Serwer

Brian Kelly, founder of the travel advice website The Points Guy, has an intriguing entrepreneurial story.

But he's also a font of knowledge when it comes to all things pertaining to credit cards and travel -- and that may resonate with you as you plan your winter or spring break trip.

I spoke with Kelly about shipping, artificial intelligence, and tariffs as part of our At Barron's interview series .

Below is an edited version of the conversation.

   Barron's: You   worked at Morgan Stanley and then The Points Guy thing was a side hustle. Tell us that story. 

Brian Kelly: It was August of '07. I show up ready to make a ton of money. I was in HR, but even my friends in HR back then were making bank, you know, on Wall Street. We all know what happened with the markets. And luckily I never lost my job at Morgan Stanley, but I -- basically there were no bonuses every year. It was, 'Hey, you didn't get laid off. Come back again next year.' And you know, at a certain point I was traveling so much. I was on a team of eight recruiters that at one point were riffed down to one. So I was covering the whole U.S. and Canada raking in tons of frequent flyer miles. I had Starwood, Delta top tier, you know, even though I was making maybe $75,000 a year. I was jet-setting, you know, first class on weekends and upgrades. And my friends were always like, 'You know that that's not normal, right?'

When I would go on a recruiting trip, the managing directors would be in coach, and here's 24-year-old me sitting in first class 'cause I had elite status. So you know, in 2010 I decided to start a little side hustle. I registered it with Morgan Stanley's outside business interests, and they were like, 'Okay, Brian, you and your little blog, you know, good for you.' [...] Within nine months it blew up beyond my wildest expectations.

So when people ask you about travel deals and the best places to go, I mean how do you respond? [...] Do people come up to you at cocktail parties and say 'I want to go on a winter vacation, where do I go?'

Flexibility is key. I say when you're buying flights, the best tool that I love is Google Flights, because you can do -- click the button 'Explore.' So you can put 'New York City,' 'if February,' 'I want to go this weekend and I want to go to the Caribbean non-stop business class.' And it'll show you a map of every non-stop flight and business class from New York or whatever city you want. And that's where you're going to find the best deals. [...] Airline pricing changes by the second, even quicker now with AI -- airlines are changing how they price -- so there's no one best time of day, you know, or a certain destination that's always cheap.

Now I will layer in tips like you know, go where the U.S. dollar is strong, right? [...] The last five years or so have been great for traveling abroad with a relatively strong U.S. dollar. But also, you know, when using your points, it's really confusing. And this is where there are apps like point.me [...] You can use points for those top periods, but there are tools out there that you have to use to get ahead. But let the deals decide where you go on a trip, is what I say.

What about AI, Brian? Is AI coming in and starting to change this whole game? You were talking about search.

Yeah, so on the airline side, I mean Delta has openly said that I think last year it was 1%, but this year they're scaling up the amount of AI for pricing. Instead of having a team of pricing analysts in Atlanta working nine to five or whatever, they now have non-stop pricing.

[...] I'm allegedly a top travel expert, and I'm going to Machu Picchu soon with my two young kids and parents. It's so overwhelming. But guess what? I use Claude quite a bit. Claude helped synthesize down the time of year I'm going. There was still a lot of nuance that was needed, where I then took a rough idea and then took it to the hotel concierge to help flesh it out. But I think AI is, you know, making it much easier to book travel. And I think that'll continue.

Are there still travel agents out there, and is there still a need for them?

Interestingly, the travel advisor -- especially the luxury travel advisors -- are booming. [...] I highly recommend using them in general, especially if you're spending a lot of money.

Never go directly to a luxury [hotel site]. This is one of the biggest mistakes luxury travelers make, going directly to, let's say, Four Seasons. If you go through a virtuoso travel advisor, you generally will get the same rate, but also free breakfast for two, which at fancy hotels adds up quickly, upgrades, credits. So in general, luxury travel advisors are worth their weight in gold. Airline melts down and you can't get through to an agent -- you pick up the phone, your travel agent can click a button and put you on the next flight before the airline.

What about the tricks that airlines [...] do to make things uncomfortable when it comes to your points? And or, what are they doing that's right?

The large issue that people are frustrated about is what I call devaluation. So every year, the airlines make it more and more expensive to go to Europe. When I first started The Points Guy in 2010, I mean Delta: for 100,000 Delta sky miles, you could fly to Europe on Air France, KLM, Delta. And I remember back then you could stop in Paris for a week, and then you could fly to the Seychelles for just 20,000 more miles round trip [...] now that trip would probably be 800,000 points.

So you know, the US airlines have been pretty bold in continuing to raise how many points you need. On the other side, there are also more ways than ever to earn points. I mean, the credit card bonuses are through the roof, even these loyalty programs -- you know, they now reward business travelers based on how much you spend. So if your company is paying for expensive last minute flights to Boston, $500, $600, you're earning way more points today than you were before.

So when you look at all sides of the equation, you know, luxury travelers and people spending a lot of money are actually getting more points, even though it's more points to redeem. So I would say a tip for people is transfer points to foreign frequent-flyer programs. That's where the deals are. You can still fly business class Air France to Europe for 60,000 miles each way in business. Same exact flight on Delta is five times more expensive. So arbitraging foreign frequent-flyer programs is the way to go.

What about miles? Is it better to use them for flights or hotels?

I recommend airline miles for flights, hotel points for hotels. You know, each program has sweet spots. [...] An interesting trend from when I first started The Points Guy is people are now becoming loyal to credit cards [...] myself included. I don't have one airline that I always fly because I found myself getting stuck on a hamster wheel. I was flying less than ideal flights just to get status. And then I came to a realization, 'What am I doing? The status isn't even getting me anywhere.'

However, now I spend on valuable credit cards -- the Amexes and Chases. I give my loyalty to the credit card 'cause I can just buy whatever flight I want. I'm no longer interested in hoping for an upgrade and biting my nails until, you know, you're at the gate staring at the agent for that upgrade. To me, that's stress when you can just spend on the right credit cards and book business class outright. That's the way to win.

What's better, [Chase] Sapphire or [American Express] Platinum?

I would say Sapphire's better for points in general. [...] I will say Sapphire will win on points, Amex on perks.

I have to ask you, is there anything you can do to make Wi-Fi on planes work?

I just flew Qatar Airways, and they have Starlink, and it is game-changing. Absolutely game-changing. United just launched it in the U.S. I mean, shame on all the airlines that have expensive, slow -- it is a solvable problem. So yeah, I'm just a huge fan of Starlink on planes.

So, message to all the airline execs out there: This is what consumers want. And you know, consistent, fast Wi-Fi. Gone are the days -- I know airline execs say, 'Well, people want to disconnect in the air.' No, we don't. So just stop, stop.

Write to Andy Serwer at andy.serwer@barrons.com

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November 29, 2025 02:00 ET (07:00 GMT)

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