Turning the Tables: My Approach to Points, Miles and Travel

All the Hacks: Money, Points & Life

Chris Hutchins shares his personal strategies for earning, spending, and maximizing points and miles on the NerdWallet Smart Travel Podcast,

Key takeaways

• Two credit cards may be optimal for most people, balancing rewards without complexity.
• Card-member flight discounts are becoming increasingly valuable and widespread.

Main topics

• Credit card strategy for maximizing points
• Award travel booking for families

Notable quotes

"One of the best points redemptions I've ever made wasn't a flight or even a hotel. It was using my Delta miles to get our wedding video done."

Conclusion

Chris emphasizes that points and miles are most powerful when used str

Transcript preview

Speaker 1 (0:00) One of the best points redemptions I've ever made wasn't a flight or even a hotel. It was using my Delta miles to get our wedding video done. And that's just one of the stories I'm going to share today as I swap sides on this episode and become the one getting interviewed about everything from my strategy for booking award flights, why two cards might be the optimal number for many people, the huge card member discounts showing up on flights these days, and why the should I pay cash or points math most people do is missing a few things. do all this, I am joined by Megan Coyle and Sally French, who are actually interviewing me for their show, the NerdWallet Smart Travel Podcast. And they've graciously let me share it with you here. I really love this conversation, so I hope you will as well. And if so, definitely check out their show, NerdWallet Smart Travel, anywhere you're listening to podcasts. And if you're new here and you want to keep upgrading your money, points, and life, click follow or subscribe. Speaker 3 (0:53) As soon as we started planning to record an episode in SF, I knew there was one travel expert we had to have on the show. Speaker 4 (1:00) It is my fellow Bay Area travel expert, SFO frequent flyer and host of his own podcast, All the Hacks. Chris Hudgin is in studio today with us to record. Thanks for joining us. Yeah, Speaker 2 (1:10) thanks for having me. Speaker 4 (1:11) But first, before we get to the main segment, I want to share our disclaimer, and that is that we will talk about a few credit card companies that are Neuralet partners in this episode. That does not influence how Megan and I discuss them. The benefits, terms, and fees mentioned were accurate at the time of posting, but of course, things can change. Some offers may have expired by the time you're listening. Chris, where are Speaker 3 (1:29) you just back from? I feel like you travel all the time. Speaker 2 (1:32) It's funny. I feel like once we had kids, I didn't travel as much. But the past few weeks have been a little wild. I just came back from Victoria, Canada. Speaker 4 (1:40) Whoa. Okay. Did you go just to Victoria, Canada? I Speaker 2 (1:43) just went to Victoria, Canada. Wow. Speaker 4 (1:45) I went this summer as part of a cruise, and I thought it was very cute. Speaker 2 (1:48) Yeah, it was a little cute. I went for a conference. Oh, conference. I landed in Victoria, went to the conference. Conference ended. Flew home. Oh, wow. So Speaker 1 (1:55) it Speaker 2 (1:55) was not, I didn't get to explore Victoria. You at least walk around the waterfront? Yeah, I got to walk around Victoria and see the lake and, you know, go swimming and all that stuff. But we didn't, it wasn't like a proper trip. We'll have to go back for a proper trip. Okay, Speaker 3 (2:06) sounds good. We'll talk about all the proper trips coming up. But first, talk to us about how you got into Points and Miles. Speaker 2 (2:12) I... Wish that I knew the moment this happened. And I tried to do some homework before coming in. So I know my dad traveled a lot for work. And so I have all these photos of me like sitting in a first class seat, sipping apple juice, flying like to somewhere somehow. I know that I flew on the Concorde when I was a kid, but I don't remember it. No Speaker 3 (2:29) way. So Speaker 2 (2:30) I was kind of surrounded by it. But, you know, when you're five and six, you know, you don't know what's happening behind the scenes. So I like I was surrounded by the travel stuff. Thankfully, my dad was always. created a frequent flyer account. I started accruing miles and points before I knew what they were, just like my kids do. And there was a point, I think somewhere in my first or second year of college, where I'd probably been earning the points, but I didn't really realize the magic until these friends of mine that were probably one or two years older, were all planning like a spring break trip to Cabo. And I was like, they're like, do you want to come? And I was like, well, I don't have any money. Like how am I Speaker 1 (3:05) going Speaker 2 (3:05) to do it? And then I looked and I had enough American Airlines miles from flying on trips with my family or other things because I didn't sound like I was traveling for work in college to buy the ticket to go on this trip that I wouldn't have otherwise been able to go on. And I was like, this is awesome. I need more. But then I used all the points. So like, I need more of these points because I don't want to miss out on another trip like this in the future. So I think that was like when I started. kind of playing things. You know, if I look at Amex, you know, it's like member since, you know, it was 2003. Nice. So I was 19. So I know I got into the miles and points game, you know, before graduating college, but. That's kind of the history that I remember to some level of detail. Speaker 4 (3:44) I love that your parents set up these accounts for you because I think the discourse right now is that parents really need to set up investment accounts for our kids, which they should. I totally agree. But next level, set up frequent flyer accounts for your kids. Speaker 2 (3:55) Absolutely. They're going to earn miles on all their paid tickets. So why not? My secret goal, and I think it might happen, I'm not sure, is like, can my kids earn status? Like, we're taking a couple trips to Europe that if they all happened in the same year. I think there's a world where they might have status. Now, they're never going to need the status because in any world where they have it, I have Speaker 4 (4:14) it. They're not Speaker 2 (4:14) drinking the Speaker 4 (4:14) free champagne in first class. But Speaker 2 (4:16) I think it'd be really funny if like a three-year-old or a six-year-old or a five-year-old had status just for fun. Speaker 4 (4:22) Well, you know, we have someone on our team who recently became a United million miler. So your kids maybe are well on track to at least have that when they're older. Yeah, Speaker 3 (4:30) he said it was because they were doing the same thing that his parents signed him up super early. And so he accrued like hundreds of thousands of miles like before he was like an adult. I love Speaker 2 (4:39) it. I'm at like 560,000 on United. So it feels really far away. And I don't think it's going to happen because all the points tickets don't count. Speaker 4 (4:48) Yeah. So like Speaker 2 (4:49) the only way you really hit it. is if you are paying for lots of flights. And I'm not paying Speaker 4 (4:54) for lots of Speaker 2 (4:54) flights. Speaker 4 (4:54) Yeah, I'm with you. I've accepted I will never have that goal. Like many things, I'll never be an Olympian and I'll never be in a million miler. So a lot of people totally see you as the guru in points and miles. We definitely do as well. Was there a moment for you that was like the, I've made it, I am the guru in points and miles? Speaker 2 (5:12) It's funny because I am leaving in a couple days to go to this like small hundred person conference of a bunch of people that are... equally, if not greater nerds in this space than me. Oh, there's so many nerds. And I would say like in that room, I'm definitely not accruing as many points and miles as those people. So in some worlds, I'm like, I feel like there are a lot of people. I mean, you're only halfway to United Million Speaker 4 (5:33) Miler. I know, I know. Speaker 2 (5:35) So I tried to track, so I had this spreadsheet where I was like, when did I, how many points did I have and across all these programs? It only goes back to 2014. And I was like, when was there an inflection point? There were a bunch of little ones. Like I remember getting the Starwood Amex, which was like... Oh Speaker 3 (5:51) yeah, Speaker 2 (5:51) that Speaker 3 (5:51) was a great card. TBT. Speaker 2 (5:52) This great card. Now you look back, I think it was like a 1x everything card. Like it wasn't actually amazing in terms of anything, but it was amazing at the time. Cards have gotten so much more lucrative now. So there was like the moment where it's like, oh, I took a trip and I remember my wife and I went to Europe and then Asia, like two separate times when we were in college and we did it on points. So like... Did I feel like I made it then? No, but I felt like I got to go on this amazing trip and not pay for it. And then I like watched the progression of points. And it's like, it was kind of like very steady growth. And then in 2025, it was a huge inflection. Oh, wait, Speaker 3 (6:29) that was last year. I know, I know. Speaker 2 (6:30) So I was like, if I looked at the inflection on the points accumulation, like the only time the curve actually started going like linearly up. was last year. What Speaker 4 (6:40) happened last year? Speaker 2 (6:41) I think last year, some combo of like figuring out lots of business expenses, getting like employee and business cards. Like there was just a lot of stuff and opportunity last year that led to a lot more points. Yeah. But I would say it was a steady climb. So there was no like single moment where I Speaker 1 (6:59) was Speaker 2 (6:59) like, this is it. It happened. Yeah. Well, my question Speaker 3 (7:03) is, were you kind of maintaining the steady amount of points because you were using them regularly? So Speaker 2 (7:08) I didn't track the redemptions. I guess I would probably have them all in my email. So that's the question is like, was I earning two million points a year and spending one? And that's why it went up by a million points each year. Yeah. Speaker 3 (7:18) I Speaker 2 (7:18) don't know the answer to that. I like it would be interesting, but maybe not interesting enough to spend the time to find out. Speaker 3 (7:23) Yeah. Yeah. OK, well, then tell us about like a redemption you were the most proud of. The Speaker 2 (7:28) most exciting redemption was when back in 2000, we got married in 2012. So let's say 2011. and we were trying to figure out our wedding. We were trying to figure out, like, okay, do we want a videographer? Like, what do we want to do? And we were like, let's get a videographer. And this guy who I'd known who was, like, a well-known tech founder in SF, he had posted his wedding video, and I saw it, and I was like, his wedding video was amazing. I was like, I want that wedding video. I looked at who made it, and I was like, let's reach out to them. And I don't remember what our wedding budget was, but when we got back the quote, like we went into it just assuming it was in our budget. And I think it was like $12,000. For Speaker 4 (8:04) a wedding video? Speaker 2 (8:05) Yeah. Oh Speaker 4 (8:05) my gosh, it's wild. Speaker 2 (8:06) Maybe it was $10,000, but it was not. In our budget. Wow. Speaker 1 (8:10) It was like, Speaker 2 (8:11) it would have been like the largest line item in our entire wedding. Wow. And I remember having no clue. I did. It's like, it's not like I looked at prices. I had no clue going into this call. Like we had such an awesome time meeting the woman that runs this company. And we were like, we clicked on so many levels. She like travel, everything. And Speaker 1 (8:27) then she sent it back and I was like, oh yeah, sorry. This is like, I Speaker 2 (8:30) wish I could Speaker 1 (8:31) tell you ahead Speaker 2 (8:31) of time, this wouldn't work. But we had. already built a relationship. I remember this like back in the G talk days on like Google, we were Google chatting all the time. And I told her we were going to the Seychelles for our honeymoon. And she was like, I have always dreamed of going to the Seychelles. And she at the time, I don't think played the miles and points game much at all. She's like, I would love to go to the Seychelles. And I told her, I was like, we're going to business class, it's gonna be amazing. And at the time roundtrip tickets to the Seychelles and business class, like $16,000. And I said, how much do you want to go to the Seychelles? And there was this crazy Delta promotion. We booked the flight, Delta points, on-air France. And there was this crazy Delta promotion that just happened to happen. And there hasn't been one since where you could basically transfer your miles to someone else for like roughly a cent a mile and they would double it. We were about to book this flight. And then instead of me booking it, I transferred, let's call it 240,000 points to my wife, became 480,000. And she had agreed. She said, well, if you want to like. Send us to the Seychelles in business class, me and my husband. I'll do the wedding for free. No Speaker 4 (9:32) way. You literally paid your wedding expenses in Delta miles. Yeah. Speaker 2 (9:36) Wait, did Speaker 4 (9:36) you also go to the Seychelles with her? No, no, Speaker 2 (9:39) no. So she was like honeymoon with my videographer. No, thank you. And funny enough, I think for whatever reason, a year or two later when she wanted to do it. They'd like Air France maybe stop flying. There was some reason that it didn't work. So she went to Madagascar instead. Whoa. Speaker 4 (9:54) Oh my gosh. My honeymoon was in Madagascar. And was it Speaker 2 (9:57) great? Speaker 4 (9:57) It was interesting. Okay. Speaker 2 (9:59) That sounds like a story for another day. So anyways, I think we paid maybe like $600 for hotels and stuff to house the videographers because that was an actual expense. But otherwise, she covered the wedding. Wow. And Speaker 1 (10:11) we have Speaker 2 (10:11) this awesome wedding video that is everything we ever wanted. Speaker 2 (10:16) you know, we got it for like 90%. Wow. Speaker 4 (10:17) Chris from all the hacks. The hack is pay your wedding videographer in miles. Yeah. That's Speaker 2 (10:23) a Speaker 4 (10:23) real hack. We could end the show now. I Speaker 2 (10:24) mean, there's this arbitrage where there are lots of people who pay. the $16,000 to fly two people internationally in business. And then a lot of people listening to this show are like, well, I know that like there are ways to accumulate those points and like the street value of those points might be $1,200. Right. And so what can I do there? One is you could take the trip. The other is if you meet someone who is about to pay $16,000 and be like, hey, can I just book Speaker 3 (10:45) this trip for you? You know, Speaker 4 (10:46) Megan has a wedding coming up. Honestly, Speaker 3 (10:47) I'm rethinking how much I should pay the videographer. Well, you Speaker 4 (10:51) have a lot of bill points Speaker 3 (10:52) you're sitting on. Speaker 4 (10:52) Maybe this lady's Speaker 2 (10:54) still looking for travel. Oh, yeah, Speaker 3 (10:55) for sure. Okay, well, I'm... also using kind of Speaker 2 (10:58) a Speaker 3 (10:58) similar hack because there are some people I want to fly for my wedding. And so I'm using the points I'm racking up to basically pay for their flights. Like you said, I think they think they're getting this like $1,000 round trip flight to Hawaii. And I'm like, Oh, yeah, you got like a 50,000 point round trip flight from here to Hawaii. And yeah, it actually didn't cost me that much. So that's great. Speaker 1 (11:19) Yeah, Speaker 3 (11:19) it's perfect. Speaker 1 (11:20) This episode is brought to you by gusto. When I started this business, I can assure you I was not dreaming about payroll, payroll taxes, benefits, yet they are something that every business has to deal with. Fortunately for me, Gusto handles that part quietly in the background, so I don't have to worry about it all the time. Gusto is online payroll and benefits software built for small businesses. It's all-in-one, remote-friendly, and incredibly easy to use, so you can pay, hire, onboard, and support your team from anywhere. They've got automatic payroll tax filing, direct deposits, health benefits, commuter benefits, 401k, and it is quick to switch since you just transfer your existing data and you don't pay a cent until you run your first payroll. I've used Gusto for every company I've started over the past decade, but it's not just me. They have been trusted by over 500,000 small businesses as well. Try Gusto today at gusto.com slash all the hacks and get three months free when you run your first payroll. That's three months of free payroll at gusto.com slash all the hacks. One more time, gusto.com slash all the hacks. This episode is brought to you by Gelt. Most business owners have a CPA who files once a year and then goes quiet. And that's the problem. The moves that actually change what you owe for 2026 close on December 31st. Once the year ends, most things are locked in and April is just the time where you end up having to write the check. Gelt is different. They're a modern CPA firm, real tax professionals backed by a tech platform, and they work on your taxes all year instead of just once in the spring. How you pay yourself, the retirement plan you set up, equipment you place in service, every one of those is still in play right now. And Gelt will run a calculated projection before the end of the year so you know exactly where you'll land while you still have time to change things. I've been working with Gelt for a few years now on both my personal and business taxes, and having one team look at both has made a real difference. Because what you do on the business side directly affects the personal side. If you own a business, right now is when this matters most. Start your year-end review at allthehacks.com slash Gelt, G-E-L-T. Again, that's allthehacks.com slash G-E-L-T. Speaker 3 (13:38) Okay, one more thing I really like about your strategy around points and miles is that I feel like Chris, you're all about things that move the needle. Like you're like, I'm not going to like go through all this extra work to get like one more point per dollar. Would you say that's pretty accurate? Speaker 2 (13:53) Yeah, I mean, there's a lot of cards out there that cover categories that I don't have. Like maybe I earn two points on pet supplies and there's probably a card that earns three. But like practically, how much am I spending on pet supplies a year? Is it $1,000? Okay, so an extra 1,000 points, like that's just, it doesn't move the needle at all. Also, if you factor, if I'm going to open up one card. that card could probably have at least 100,000 point welcome bonus, right? So like if I could get a welcome offer worth 100,000 points, or I could open a card that's going to give me an extra point per dollar on $1,000, it's going to take me somewhere on the order of 100 years for that to break even. So like those kinds of things don't move the needle. Now, if you run a business and you spend a ton of money on gas, and let's say you spend $4 million a year buying gas for a fleet of vehicles. Well, then, yeah, you should get a card that's going to give you a lot more points per dollar in gas. That makes sense. But if you're spending $300 a month on an expense and you could get one more point per dollar, it's probably not worth it relative to what you could get. from a welcome offer on a card. Speaker 4 (14:52) You're speaking my language. In fact, Megan and I differ a bit on this, but I keep it so simple. And I have one card that just earns 2.62 back on everything. And I just commit to that. And that's the way I go. And I don't stress about a ton of bonus categories. But I have a lot of friends who are like, oh, this one card gives me 1 % back more. Should I do it? And I think about not just what you mentioned, which is true, but even the stress of moving all your auto pay expenses, having a new password to manage, having to manage all these different cards. That gives me anxiety. Well, Speaker 3 (15:18) also, I think the signup bonus.