How to travel for less: The Points Guy takes 3 Pressing Questions

24:49Okay, well, my value is material to this business. And, you know, it's 2026 now. It's been, yeah, that was 2017. So we're coming up on nine years. And I stepped down as CEO in 2020 because then it just became back to your original question of a hundred some employees. That was never my intention. My talent in life is not people management. And I kind of realized I need to be in front of the camera with clients, with our consumers. I believe in the brand and our content, but managing people is a fully different skill. And I was so busy traveling. I'm doing our charity work. Like I'm so like, you know, taking the time to have a, you know, an exec team of like six senior executives and then spending time with each of them and new employees.

25:35Like I was not the best boss and I 2020 hit and I realized I was so burnt out. And but that's the beauty. Red Ventures, I went to them and I was like either, you know, it's been 10 years of the points guy. I've had my earn outs and everything. Is it time for me to go? But I just can't do this, you know, being in HR meetings all day, every day. It's so refreshing to hear about what it took for you to kind of push through to learn what your worth was, because I think a lot of founders struggle with that early on. I'm so curious as well. Obviously, now a lot of your job is talking about how to travel hack and make the most out of your trips.

26:11One of the things that I have gotten so many questions about for your interview today is obviously about the airfare prices to kind of turn here a bit. They seem to be all over the damn place right now. So anecdotally, I recently saw a$700 ticket from London to Ibiza, which was just shocking for a short haul. So the big question, I suppose, is when do you realistically see airfares coming down, if at all? We're in a crisis. I think we're just starting to really understand it. I think we're all, as humans, like, oh, this will be over. The Strait of Hormuz is going to open up. And, you know, in six weeks or so, it'll fix it.

26:47It's not. Like, I think we need to start understanding, like, this summer is already, even if right away, you know, it's fixed, there is no immediate fix. And we're seeing there's going to be consolidation. So I think we're going to see, you know, United has joked kind of about buying American. What was your take on that deal, by the way? I did see you spoke about that. Yeah. United isn't buying American. I think the odds of that are very low. I think there were several tactics there. Number one, Scott Kirby. The CEO of United. See, he's on a high right now. I mean, United had good first quarter results, and he's really coming for Delta.

27:24He wants to position himself as the dominant force. For so long, United has lived at number three. Then it scratched its whites to number two. And so I think he just saying that and leaking that clearly he or someone at United leaked that information for a reason. And I think really they'll probably buy JetBlue because JetBlue hasn't turned a profit in years. And the fundamental, when JetBlue has doubled the price it was January 1, all of these airlines, which have been struggling for years, it just dramatically exacerbates the problem. So JetBlue's an issue. Spirit is an immediate issue. And the problem is once they start merging or going away, airfare's going to go up even more.

28:04Not only airfare, but fees. So all the airlines have increased baggage fees by 30 percent. And that doesn't go back down. You have been talking about that, that there's this de-bundling happening. Can you explain what that is for those who don't know? So the airlines basically just need to maximize every single square centimeter on the plane. And so de-bundling is a great way to convince the consumer, OK, I still got a cheap fare, but we're not going to give you free check bags, which Southwest got away with. You're going to now have to pay for that. But so what, because the consumer focus is so much on the fare, but fees are where the airlines make so much money.

28:42So instead of raising airfare, which will make people stay at home and not travel, what they're saying is you can still travel for cheap, but we're going to nickel and dime you and charge you for your seat. On everything else, basically. Yeah. When you're buying your ticket, you may say, I don't care about my seat, but then you're like, oh, I don't want to sit in a middle seat. So then you eventually end up later paying$60 more. So you wouldn't have paid that$60 extra at the time of booking. But when all is said and done, you're paying the airline more for what used to be all included in one price.

29:09And I think I've heard you talk about this just like as one of the most common pitfalls you see when it comes to booking travel, right? What are some of the other things that you would say to avoid other than, you know, just making sure you're not just trying to get the cheapest airfare, period? Well, on the cheapest airfare, so these basic fares do not have any flexibility in terms of even changing your flight. And one of the best things that came out of the pandemic was most of the airlines now will let you change flights for free. And changing flights pre-pandemic used to be really expensive.

29:35So that's now free when you buy a standard fare. Now, even business class United just launched their basic Polaris, which is our basic business class. So you can pay a$5 ,000 business class ticket, not earn any miles, not be able to change it. But spending maybe$400 more, you get tons of flexibility, free changes, et cetera. So cheap is expensive these days, especially if you do need to change your flight sometimes, if you have kids, if you have a sick family member. Do not go for those cheapest tickets. You will regret it when you get zero back when anything happens. And we all know life comes in the way.

30:10Secondly, I would say travel insurance, really, if you've always shrugged it off, now is the time. I have a yearly policy. But never get it through the airline or hotel. always go through like insuremytrip.com is the independent sort of marketplace so we can compare and contrast. And why not though? Why not through the direct platform? Because the airlines will sell you a really inflated policy. And most of the time it's not even insurance. It's called travel protection. So they're selling you at the price of travel insurance for a far inferior quality product. You're paying for the price of a Lexus and they're giving you a Dodge Neon.

30:44So at the same price, just go to the independent dealer marketplace and just buy it there. A lot of people have been saying, book all your flights now because it's just going to keep going up. Is that something you think? Absolutely. Even private jets. In Europe this summer, I'll use my miles to go to Europe, but around Europe this summer, especially because there's the new EES. Not to add more drama to an already chaotic system, but the EU is rolling out this new electronic entry exit, And that's causing four-hour delays in many airports where you have to use a kiosk now. Americans will have to go.

31:16The first time you go to the EU, fingerprints and biometrics. And they're causing huge lines. So I'm booking a private jet. And I'm booking it now months in advance just because availability can be down and prices will most likely raise. I've been sounding that alarm since the beginning of the year to just book in advance this summer. And I haven't heard of a single person who said that they're upset that they got tickets in advance. So, yeah, in general, do not procrastinate. Although procrastinate, if you have frequent flyer miles, it can be the best time when airfare is really high. The airlines are still releasing a lot of award availability.

31:54They want every single flight seat to go out full. So you can still use points even when airfares are really high and even last minute. That's a great tip. So it really depends on what you're trying to go for. Let's talk about the future of our... Hey Chicago, class it up with Crocs. You know back to school is coming in fast. So why wait to find your new fave footwear? Step into a local Crocs store and step into your new look. Try it, style it, make it yours. Because the right pair doesn't just show up, it shows off. First day fits, handled. Walk out ready for whatever's next. Visit your nearest Crocs store today.

32:37This episode is brought to you by Accenture. When your advertising operations fall out of sync, everything else follows. Spotify and Accenture are working together to reinvent the rhythm of ad sales, using automation, analytics, and smarter workflows to simplify campaign delivery and access better data across the business. The result? Less time spent on operations, more time connecting brands with the moments and fandoms that matter most. Learn more at Accenture.com slash Spotify. Travel. We're starting to see new cabin concepts emerge in economies such as United's Relax Row, where three economy seats can convert into a couch-like space.

33:16And obviously, we know that Air New Zealand was one of the first to come out with this, right, the so-called sky couch. Do you think this kind of hybrid economy product will become the norm, or is it still more of a really niche experiment? And why haven't we seen it been picked up more? Yeah, it's just a really brilliant concept. Some airlines like Lufthansa will sell empty seats that we all get lucky on a flight and you've got the road to yourself. Well, now the airlines are saying, we're not just going to give that away for free. We're going to sell that. And it's brilliant because the airlines, once again, I mean, to their defense, they're in a really tough time with these rising costs.

33:49And airfares are not increasing as much as their costs are. So, yeah, I see that they will roll out more options because the economy cabin, they can actually make more selling those couch seats where they're taking people who are in the same row and basically just reshuffling and maximizing. It can be more efficient than business class because a single business class seat can take up six seats and they can actually make more revenue per square foot on the plane by maximizing. And especially because most empty seats that go out are an economy. So basically just turning money from wasted space that would have went out before.

34:27So, you know, the relaxed row requires some extra equipment in the row and the sky couch. But I see more and more airlines should at least do the day of departure, upgrading people to their own row so that they can lay down versus just giving it away for free to the lucky person who ends up in that row. Yeah, no, exactly. I was just so curious because it would seem like there's lots of demand for something like that. Obviously, most people do fly economy. So I was just surprised that it's not become more of the norm already. It's just interesting because people are cheap. And I will be interested.

35:00I think the reason why they haven't rolled it out because these products, you know, I don't know. Most people paying, you know, there's a new bunk bed concept on Air New Zealand. It's$500 to get four hours of sleep. I think a lot of people would say, all right, I'll just stick it out. I don't know if there's going to be a ton of people saying, let me just depart with$500 that I could use on four nights of hotel or something in my location. So it'll be interesting. I definitely think there is a business there. But I just don't know how many. People are still really cheap when it comes to flying and we'll just grind through.

35:37Yeah, that's true. Well, on the flip side, I have to confess, I really love following you because I like my own high-end travel and I like having nice things. Obviously, we all want to always get the best deal, though. So, you know, I'm curious when it comes to the luxury space, where have you found some of the best value? Who's standing out to you right now? In value for luxury is really tough because we've talked a lot about airlines, but hotels are just wildly priced. Like, you're, you know, planning to be in Italy and Croatia this summer and Portugal. I mean, normal hotel rooms in Italy, the five-star hotels that used to be$1 ,000 a night pre-pandemic, now they went to two.

36:16Look,$4 ,000 a night is the new norm for a normal room in Lake Como and certain places in France, the Four Seasons, normal room,$5 ,000 a night in Cap Ferrat. And there still is this huge demand. And we're seeing it in the luxury cruise space too. Four Seasons just launched their yacht. Amman is next year. or an express, I actually think the best value is almost cruising these, you know, you can actually get a, because when you're spending 4 ,000 a night, 28 ,000 on a room that then you have to pay an exorbitant amount for food and beverage, a lot of these cruise lines, um, it's cheaper to go on a floating cruise ship and see five different ports.

36:58And the rooms are actually really nice. I, I, I haven't taken the Ritz ship or whatever, but I hear great things. And to be able to, you know, in the Mediterranean, go see four different areas without having to deal with airports, which are dramatic cancellations. So I do think that all the investments in these luxury ships will pay off. And some people will say, well, for$60 ,000 a week, just rent your own boat. But you don't realize the boating industry has gone up, too. I mean, it's a quarter of a million dollars for like a decent boat, plus provisioning, plus, plus, plus. It's exorbitantly expensive.

37:33So for$50 ,000, you're not getting a yacht experience. You know, you could get a small sailing boat maybe, but it's nothing like getting the Four Seasons or Amman experience. But I would say if you're booking luxury hotels, never book directly. Always book through – I highly recommend through luxury travel advisors, so Virtuoso agents, you know, the Amex fine hotels or chase the edit because you get early check-in, late checkout. A travel advisor will charge you the same amount for the hotel, but you have this expert who can, if they have a relationship with the hotel and the GM, they can get you upgraded.

38:09And if something goes wrong, instead of, I hate going to the hotel and negotiating for what I want, you call your agent, a high powered agent. If you got a bad room is calling and saying to that hotel, you better make it right for my client because I have tons of other wealthy clients. So that's a trick I think a lot of people fall into. Never go to fourseasons.com, use an agent who the hotel pays them, and then you have them as a concierge. That travel agent, not just for a hotel, can also organize the VIP person to pick you up at the airport and just make everything seamless. And often at no extra cost.

38:43Is that right? Yeah. That's something people don't realize because I'm saving for my honeymoon right now. So on a personal note, and I've heard you say this, if you're going to safari in Africa, which is what I'm trying to do. Don't just book direct. You can actually do it for the same price, but more perks. Totally. And have the expertise of someone, you know, Roar Africa is one of my favorite travel agencies in Africa, female owned, and they've been to all the camps and can give you the perspective because having that inside knowledge can make all the difference. I do think a lot of people have bad hotel stays because they were never supposed to visit that hotel.

39:16because right now discovery on hotels is through Google. Who's paying Google or Expedia the most to get seen? And I think a lot of people are not getting matched to the right property and that can make all the difference. So having an advisor who specializes in safari or specializes in Mediterranean cruises and can say, you know what, based on what I know about you, you'd actually love this ship that you may not have heard of. And oh, by the way, we can get you special pricing. Like they can pay, luxury travel advisors will pay for themselves many times over. On that note, for the average traveler, where is the best place to look for flights and book?

39:52You know, when it comes to platforms like Google Flights, Skyscanner, I feel like my friends are always like, what is the difference even really? Yeah. So, I mean, I'm a big Google Flights fan. It's 90 % accurate. Like there's some airlines that aren't in it, especially internationally. There's a feature called ExploreMap. And if you're really looking for the best deal, you have to be flexible these days. So if it's March and you live in New York City or Chicago and you want to go to the Caribbean, you can go to the explore tab and put in your home city and then put in Caribbean certain dates or four days over this month or whatever.

40:24And it'll just show you a map of the region, whether it's Europe, Caribbean, and it'll show you the cheapest islands, the cheapest countries. And you can sort by nonstop, by certain carriers. and that's where you save money is when you can look at tons of different options all at once instead of having to click one by one. The same, there's a tool called seats.aero. So if you have points, seats.aero will actually look at the entire year. And so if you're flexible and you just wanna go LA to Tahiti on Air France, you can actually pull up an entire year's worth of what days they have business class or premium economy.

41:00So like using technology to give you the big picture and then sniff out the deals for you. What is one of the biggest steals you feel like you ever stumbled across? Well, I would say this summer, I mean, Air France Flying Blue, frequent flyer program, which transfers in from Amex, Chase, Cap One, all of them, they have 60 ,000 point business class awards to Europe on tons of days this summer. So to put it in perspective, like United, it's 200 ,000 minimum, 300 ,000 most days, one way business class. Delta's 450 ,000 points, you know, American. So 60 ,000 points one way or 120 round trip is a steal, especially when round trip business class six,$7 ,000.

41:42So currently I think, you know, flying blue is probably my favorite loyalty program of the moment. There's also a lot of like travel domestically. You don't have to travel in first class. There's a lot of programs, Alaska Airlines, which is now one world. you can fly American Airlines flights, even flights, last minute flights from Miami to Philadelphia can be$500 and you can get them for like 7 ,500 miles. So there's a lot of like short haul, short distance based award programs like Alaska where you can get outsized value, especially if you're a last minute booker. And once again, last minute, the airlines open up a lot of award inventory.

42:22So you don't have to be flying business class internationally to get good value from points these days. Hey Chicago, class it up with Crocs. You know back to school is coming in fast. So why wait to find your new fave footwear? Step into a local Crocs store and step into your new look. Try it, style it, make it yours. Because the right pair doesn't just show up, it shows off. First day fits, handled. Walk out ready for whatever's next. Visit your nearest Crocs store today. This episode is brought to you by Accenture. When your advertising operations fall out of sync, everything else follows. Spotify and Accenture are working together to reinvent the rhythm of ad sales, using automation, analytics, and smarter workflows to simplify campaign delivery and access better data across the business.

43:17The result? Less time spent on operations, more time connecting brands with the moments and fandoms that matter most. Learn more at Accenture.com slash Spotify. Yeah. And speaking of international, I will say one of the big things that I always think about is why do U.S. airlines often seem behind certain international carriers when it comes to the more premium product? Because we all know Emirates, Cathay, they really pamper you. This is my hill to die on. I mean, the U.S. carriers got to get their act together. There's a lot of issues going on here. But, you know, simply put, it's capitalism 101.

43:50one. They drive as much to the bone. They give as little as possible. They spend so little on food. You know, they're not saying, Asian carriers like Singapore will say, what cuisine can I offer that will enhance the experience? Like the U.S. carriers are how much, what's the lowest level of quasi dog food I can give you so you're not going to not book because I know you're addicted to the loyalty program because I know you need elite status. Is there a structural issue here though? Is it because there's so much competition? Or what is it really, genuinely? It's just that the US airlines are just chasing profits more than the others.

44:24You know, the Middle Eastern carriers aren't as, you know, incentivized to give quarter to quarter results, you know, because they're backed by the governments largely. The Asian carriers, you know, the sense of pride and brand, there's just different cultural differences where, you know, the US carriers are all about profit. So sheer greed, basically. I mean, essentially, and how long can I possibly take before I have to renew the cabin? And I hate to say it. I mean, there are certainly great U.S.-based flight attendants. But the flight attendant, I almost always avoid flying U.S. carriers. I have had so many experiences of aggressive, mean, spirited.

45:01Like, I hate that energy when a flight attendant screams. Like, on a U.S. carrier, it's normal. They don't even say hello. They come up. What do you want? Chicken or fish? Tell me now. And they're like, my adrenaline gets going. I'm like, what is going on when you fly foreign carriers that have pride? you know and the same thing in the middle of the night u.s flight attendants screaming in the galley screaming complaining like clanking dishes it's almost like in a business class where people are trying to sleep so i've had so many weird experiences and i know i'm not alone um so yeah i think there's like labor issues to figure out which uh u.s airline to build loyalty with when i moved back yeah yeah i want to ask also you know on a personal note you recently crossed a milestone lately which i just talked to you about where your son cooper just became the youngest person ever to visit all seven continents.

45:48Tell us about this journey and what inspired you to take him on this. I didn't, you know, start off thinking that we would do this. You know, when he was born, my book came out last year, How to Win a Travel. He was born in December. My book came out February 4th. So I had extreme parent guilt because I was on book tour and I was not spending as much time as I would have liked with him and my other son, Dean. You had three babies. So I have two babies. Yeah. Oh, three babies. Yeah. I had two new babies, my book and Cooper. So basically what I said was in April, I'm going to take the month off.

46:19We're going to go to Thailand. And we did. So we went to Thailand and that summer went to Europe and I was invited by National Geographic to go to Antarctica. And I said, well, I'm not going without my kids. And they said, well, you can now fly the Drake. So you can fly over the Drake Passage, which is like the world's most dangerous waterway. So instead of having a day and a half of rocky seas, you just take a plane two hours you land and kids as young as one at the time were allowed to go um you know with doctor approval my kids are healthy there's doctor on the ship and funny of my friend uh who worked for national geographic his husband is a doctor pediatrician so there were pediatricians my son's healthy the ship has stuff so i felt good about going and so once i had australia book when i was in europe that summer i was like well let me just pop down to morocco we got we went to tangier which is beautiful for a day.

47:10And, um, and so, yeah, uh, and we flew to South America to get to Antarctica. So the last was Australia. I would say, I mean, the trip to, we went to Machu Picchu and then Antarctica and I'm a single gay dad. I have an amazing nanny. Well, we'll not, I'm very transparent that I don't pretend to do this all myself. I have an incredible nanny who used to be a flight attendant and a Montessori teacher. So she's like my dream. She loves to travel. She, her attitude is good. Everything traveling with kids is your attitude. I mean, everything in kids, in my opinion, they pick up on, you are their Northern star.

47:46Kids are born not knowing what the heck's going on. So they look to you for everything. And with travel, you can plan. I like doing night flights when they're sleeping, always having games, food, just plan for the worst, but also your attitude and having a good traveling partner and just going with the punches when things go wrong. And I think, you know, there were definitely had flights with the kids were crying and, but it's just like, don't panic. Parents get panic, like, oh, you know, I'm in business class and then you, it's a spiral. And I think just having the strong attitude of like, you're doing everything possible.

48:23Take your kid, go on a walk on the plane, go to the galley, do what you can to not disturb other passengers. But at a certain point, like we were all kids and you know, they deserve to be here as much as anyone else. It's so refreshing because I do know a lot of young parents that get scared to fly with their kids. So it's so great to see that you're trying to bust through that. I guess lastly, you know, what is your endgame here? If we were to sit back down in, let's say, 15, 20 years, where would you want to be? I love where I'm at now where I'm able to do the points guy. I think there's a lot still at the points guy I would love to do in terms of technology using AI to help people better maximize their points and track their points.

49:01The technological underpinning of the loyalty world is based on very old technology. So how do we use blockchain? But that's like a larger industry. The industry has to come to the 21st century because a lot of the technology behind airlines is so dated and credit card companies. But I also, you know, I've been an angel investor and I've had some really huge wins there. Built, you know, was an idea that Ankur Jane, the CEO, came to me in 2020 when I wasn't traveling and I and, you know, helped him create Built, which is now, you know, an$11 billion company and growing rapidly. So that's been really, I love being able to invest and advise startups who are attacking parts of the industry that I know need to be fixed from a consumer perspective.

49:49And so, yeah, I think my goal now is to, you know, be an investor, but also like I'm very cognizant. My kids are one in three now. Being at home with them, especially while they're young, pre-kindergarten, traveling with them still is my number one priority now. So I try not to plan too far in advance. But I think, yeah, me continuing to invest and, you know, keeping the doors open. Who knows? Maybe there will be a time in the future to get more involved in the day-to-day of the points guy. But for now, I have this really great period of, you know, doing what I love at the points guy, investing my own money on the side in really innovative companies, which keeps me engaged.

50:31The AI play is really interesting. I can see you're eyeing another new category to create there. Brian, thank you so much for breaking all this down. Now we're going to end with a quick rapid fire round. Don't overthink it. Just say whatever comes to mind. Favorite airport in the world? Singapore Changi. Ah, yes. So beautiful and quick. That's true, the jewel. Yeah. Most underrated city to fly into? Hmm. I will just say, well, my most underrated place to visit is Guatemala. I think it's so stunningly beautiful. Culture, Mayan, energy. It's like highly recommend. I've been multiple times. Yeah.

51:04Pet peeve when it comes to travel. My pet peeve is people screaming at frontline employees. I see it all the time. It is so rude. These employees don't want your flight delayed. They're not doing it. And so misplaced anger in travel really grates me. Big issue. Best airport lounge in your view? I love the Chase Sapphire lounges are really nice in terms of like main lounge. But the Air France La Premier Lounge, I love the most because they pick you up in a Porsche at your plane and take you from the lounge in a Porsche to your plane. So the ease of just not even having to navigate the airport is Air France does the ground experience the best.

51:45We recently had on the CEO of PS, which I'm sure you can do it with. That's very similar, right? I love, yeah. What PS is doing is incredible. I love that product. Another fun one for you. Very insightful. Brian, thank you so much. Thanks for having me. Safe travels. Thanks for joining us on Behind the Business. For more stories on business and leadership, follow us on Apple Podcasts, Spotify, YouTube, or wherever you get your podcasts. See you next week.

52:29old styles, cool kicks, backpacks, and even dorm room essentials. All the prices that won't hurt your wallet. So don't sleep on Dee Dee's. Whether you've got a second grader or a sophomore, Dee Dee's has your whole family covered. Find a Dee Dee's discount store near you and go check it out today.