The Path to Becoming an Expert in Points & Miles with Devon Gimbel

00:00:00.000 | What if the way you've been thinking about points and miles is the very thing holding you back?

00:00:04.380 | Today I'm talking to Devin Gimbel who has a perspective that as soon as I heard it I knew

00:00:08.600 | I needed to have her on the show. So we're going to break down her four-step framework for points

00:00:12.460 | and miles. We'll explore some tactical ways to overcome analysis paralysis and why using points

00:00:17.700 | for maximum personal value beats trying to optimize the wrong things. We'll also cover a

00:00:23.040 | few new tactics for accumulating points, scaling point strategies for families, and a lot more.

00:00:28.360 | The best part about this conversation is that I think it will be just as valuable to someone early

00:00:32.620 | in their points journey or a little bit further along feeling stuck as it is to someone who's as

00:00:37.240 | far down the rabbit hole as I am. Speaking of me I'm Chris Hutchins and if you enjoy this episode

00:00:42.060 | please share it with a friend or leave a comment or review and if you want to keep upgrading your life

00:00:46.560 | money and travel click follow or subscribe. Devin how do you think you think about points and miles

00:00:52.580 | differently than others in the space? I think that there is an absolute use for looking at points

00:00:57.580 | and miles as how do we use these to essentially get free or as close to free travel as possible.

00:01:03.040 | I think that's an amazing use of points and miles. So I'm not necessarily looking at how can points

00:01:07.420 | and miles keep my travel costs as low as possible. What I'm looking at is how can I take this travel

00:01:13.160 | budget that I've allocated? How can I expand it at exponentially using points? And when that's the

00:01:19.760 | actual question then I think that automatically informs kind of everything that comes downstream of it.

00:01:24.200 | So some of the I think mainstream advice about how to earn points while I think that it's useful and

00:01:29.960 | valid depending on what your background is it's not applicable necessarily anymore for me. So I'll just

00:01:35.960 | give you one example. When I was learning about points and miles I felt like a lot of the information out

00:01:40.440 | there was essentially always be working on a new welcome bonus offer. Allocate all of your expenses

00:01:45.140 | to a brand new credit card and then just rinse and repeat. And again I think that there are scenarios where

00:01:50.120 | that makes amazing sense. And there are scenarios where it doesn't, you know, fast forward a couple

00:01:55.000 | years. My husband is self-employed. I am now self-employed. We have businesses that have expenses.

00:02:00.780 | Our expenses are now at the level where it is not practical for us to have an approach where all of

00:02:06.980 | our expenses should automatically go on a brand new card in order to earn a sub. The number of cards that

00:02:11.420 | we would have to be applying for on any given day makes me even as a points enthusiast start to sweat.

00:02:17.580 | It is just not possible. And so I think there are areas where a lot of traditional points and miles

00:02:22.020 | advice and education are phenomenal. And then depending on what your background is, your context is that may

00:02:28.160 | not hold true anymore. I will gladly and enthusiastically pay a processing fee in order to pay certain expenses

00:02:34.820 | with a rewards credit card to earn points, even if I'm not earning a welcome bonus on that specific

00:02:40.640 | expense. And it's only because I have run the math and it makes sense given my kind of specific scenario

00:02:47.580 | is that there's no one right way to do points or miles. There's no one right way to earn them or to use

00:02:53.380 | them. And once you have kind of a foundational amount of knowledge and experience, then you can start

00:02:58.860 | getting really critical and curious about, okay, but what about me, right? What about the way I want to earn

00:03:04.060 | points and use points or what about my specific situation might actually call for a deviation from

00:03:09.940 | what is actually really conventional and sometimes amazing education and advice out there?

00:03:14.660 | This reminds me of an email I got and I shared it with you where someone said,

00:03:18.260 | Chris, you give so much information, but it's really hard, at least on the point side for me to put it to

00:03:23.400 | use. I feel like I've unlocked this magic. But now when I think about trying to maximize it,

00:03:28.180 | you've taught me the scope of everything that can be done. And now I'm convinced I'm just going to screw it

00:03:33.300 | up and I'm almost paralyzed. And I feel like the reason that I first thought I had to invite you on

00:03:39.180 | You've got a way of thinking about this that I think would be really helpful to people, not just at that

00:03:44.900 | stage, but throughout the journey that would make it a little easier to think about how to get out of

00:03:50.740 | some of that paralysis, how to feel better about learning a lot. I know as a podcast host, I like

00:03:56.500 | dumping lots of information. I don't want that to be too overwhelming. So I thought we could walk

00:04:00.840 | through that framework you have and then talk about a bunch of tactics that people can fit into it at

00:04:05.680 | different stages. Let me talk about what is this framework? Some people may be familiar with it,

00:04:10.240 | people might want to Google it. So there's this one very specific graphic. It's a curve. It's called

00:04:16.380 | the Dunning-Kruger curve. So we can link to that in the episode show notes. You can, like I said,

00:04:21.160 | pull this up on Google. And kind of where this comes from is that they wanted to see was,

00:04:25.720 | okay, how do people experience kind of themselves based on how much knowledge or skill they have in a

00:04:32.440 | specific area. So they ran these participants through, you know, the study, all of these tests

00:04:36.960 | to assess competency in certain areas. And then they also surveyed the participants and actually asked

00:04:42.200 | them, okay, how well do you think you did? And a lot of us, when we know nothing about something,

00:04:47.720 | we're like, yeah, I don't feel very good about that. And once we know a lot about it, we feel very

00:04:51.900 | confident. But what was really interesting that Dunning and Kruger found is that this very kind

00:04:56.940 | of first stage of learning their first stage of competence in something, where you're actually very

00:05:01.840 | bad at something, or your level of knowledge in it is very, very small, a lot of us tend to have a lot

00:05:07.040 | of confidence at this time. Now they have a term for this kind of phase of learning or this phase of

00:05:14.160 | competence. And I don't know exactly what they say. But I call this sort of the peak of Mount

00:05:19.120 | ignorance. Because when you look at this curve, if you want to pull it up online, you'll see that with

00:05:23.460 | just a tiny, tiny little bit of movement in terms of your knowledge or skill, your confidence skyrockets.

00:05:28.460 | So it goes way, way up. And I think when this relates to award travel or credit cards, I think

00:05:33.700 | we've probably all gone through this experience at some point. You know, we laugh now when I talk to

00:05:39.360 | friends who know about points and miles, someone will text me and be like, Oh, you're not going to

00:05:42.360 | believe this. You know, I was out at dinner. I was treating, you know, my family to this dinner,

00:05:47.080 | the guy next to me made a big show about pulling out his Amex personal platinum card to pay for

00:05:53.420 | dinner. Basically, wow, there's so many other credit cards out there, you know, that are so

00:05:57.480 | much more valuable in terms of earning points for dining than this one specific one. But that guy in

00:06:02.380 | that moment is like, I have this amazing credit card, you know, I'm earning all these points is

00:06:06.940 | probably only because he doesn't actually know what he doesn't know yet, right? Maybe he doesn't know

00:06:10.860 | that there are other amazing rewards credit cards that are going to get him so much more points for

00:06:15.540 | dining than an Amex personal platinum card is. But when you don't know what you don't know that

00:06:20.780 | really, really fascinating thing about this is that you don't feel bad about it, right? You the amount

00:06:26.680 | of knowledge and skill that you possess, you're feeling pretty, pretty good about it. And that is

00:06:32.280 | the fascinating thing about this first phase, there's a different way to do this. And that's where

00:06:37.020 | actually I encounter so many people in this hobby, which is they're no longer at that first stage of

00:06:41.400 | learning where their confidence is really high, even though their competence does not match it

00:06:46.580 | yet. Instead, they've already moved on to the next phase of what happens when we tend to learn, which

00:06:51.800 | is that as high as you get with your confidence initially, when you don't have a tremendous amount

00:06:56.660 | of knowledge or skill in this area, you get just a little bit more knowledge, you gain a little bit

00:07:02.060 | more skill. And what Dunning and Kruger found happened confidence in the second phase is that it

00:07:06.620 | plummets, like it goes very sharply downward, very, very fast. So many of us, I think, go very quickly

00:07:13.640 | from Oh, my gosh, this sounds so amazing. Or I want to dive in, I want to learn about this, to I am

00:07:19.460 | doing it all wrong, right? They realize, wow, I've missed so many opportunities. I signed up for a credit

00:07:25.380 | card and didn't even earn the welcome bonus, because I didn't realize that was a thing, right? People tell

00:07:29.220 | me, you know, I used all my points, and I redeemed them for what I now realize was incredibly,

00:07:34.120 | incredibly low value. Like, the refrain of this phase of learning is basically, I did it all wrong.

00:07:39.000 | And this is why I think when you understand the way that we learn, and you realize, Oh, no, this is

00:07:46.060 | just a phase. My hope is that people will realize like, No, no, this is not the end. This is not where

00:07:50.480 | you say, Oh, yeah, it's too hard. And they give up. When you understand this is how we learn. This is how

00:07:56.160 | we experience building skill. Then you can understand, Oh, wait a minute. Now there's more that comes next

00:08:02.340 | and not give up. You've also talked about this as like unconscious incompetence. And now you've moved

00:08:07.680 | to conscious incompetence. It's like now you know what you don't know. And I feel like I've been there.

00:08:14.300 | The email I got was about someone who was there. And honestly, I feel I'm sorry to everyone who I have,

00:08:22.000 | you know, introduced from their unconscious incompetence to their conscious incompetence.

00:08:27.340 | But I will say that for every email I've gotten every story I've heard of someone who feels

00:08:32.540 | overwhelmed. There's five more emails of people who made it through this this kind of valley of despair,

00:08:38.540 | and have started to master these things have started to apply them and gotten one win. And

00:08:45.780 | the knowledge of I now can do this better. The knowledge of that one win is it brings you up this

00:08:53.720 | this journey to amazing things. And I know it can feel tough. I know it can feel hard at the beginning

00:09:00.140 | because we've all been there. But but but how do you get out of this valley of despair? And what does

00:09:04.440 | that look like?

00:09:05.120 | Yeah, this is I think the question that everybody wants answered. Okay, what now is like, you could

00:09:10.300 | give up? Hopefully you don't. And Chris and I are here to tell you, you know, so many people have

00:09:14.300 | learned how to do this, you absolutely can learn how to do this. But what do you do when especially you

00:09:19.200 | notice that you're in this phase of feeling like there's too much to learn, or you don't have enough

00:09:25.320 | time? One is when you actually do just allow yourself that moment to recognize, wait a minute,

00:09:29.900 | what's actually going on, is that I have learned more than I knew before. It's just that my confidence

00:09:36.580 | has gone down actually no more than I did a month ago, a year ago, 10 years ago. It helps to reframe

00:09:43.560 | and remind you, wait a minute, no, I am actually getting better at this in terms of my knowledge

00:09:47.760 | base. And what follows knowledge is skill. So as long as you keep learning, you keep practicing,

00:09:53.520 | you keep trying, your skill is going to catch up with that knowledge. And so in the beginning,

00:09:58.440 | it really is just reminding yourself, no, no, no, no, no, it doesn't feel easy right now. But there

00:10:03.580 | is value in continuing to work on this. Because what happens next is that as you continue to gain

00:10:09.480 | knowledge or skill or competence, you know, in this specific area, your confidence actually does start

00:10:14.680 | going back up. So it doesn't shoot straight up the way that we initially see kind of at the beginning

00:10:19.420 | zone of learning. But now it starts a really strong and steady climb upwards. And this correlates with

00:10:25.180 | a transition between becoming what's called consciously incompetent. So you stink at this,

00:10:29.340 | but you realize how bad you are at it, to actually transitioning into conscious competence, meaning

00:10:34.460 | that now you're actually getting better at this thing, even if it takes concentration and hard work.

00:10:40.980 | And what this means is that, you know, I think you if you're in the world of points and miles,

00:10:45.460 | if you listen to Chris talk about all of the amazing things that he does with points and miles,

00:10:49.940 | he doesn't probably seem like he has to work very hard for it, right? He could probably walk

00:10:53.620 | around with 10 credit cards in his wallet, and know off the top of his head for any given expense,

00:10:57.820 | what's the best card that he wants to use for that expense. I bet if you asked him,

00:11:02.520 | hey, I want to take a trip, I have a family of three, and I want to travel from the East Coast of

00:11:07.440 | the United States. And I want to visit any major city in Europe, what should I do? I bet that off the

00:11:14.540 | top of his head, he could probably rattle, oh, here are a couple airlines you might want to check or

00:11:18.140 | here's the first step, right? The only reason he can do that is because he continued to learn

00:11:23.780 | and practice and he moved out of conscious incompetence into conscious competence. And so

00:11:29.200 | all you really have to do, and I'm not trying to minimize this at all, I'm really trying to break it

00:11:33.540 | down and make it simple is that you just learn one thing at a time, you just try one thing at a time.

00:11:39.380 | I think one of the biggest mistakes we can make in this hobby is thinking, I need to try to learn it

00:11:44.380 | all immediately, or I need to try to implement 20 things at once. You don't start with where you are

00:11:51.280 | for some of you that's going to be saying, look at the credit cards that are already in your wallet,

00:11:55.100 | how confident are you that you're using them very well to their highest advantage right now?

00:12:00.280 | Maybe you're walking around with points earning credit cards that you didn't even know are earning

00:12:04.520 | points. And so where you want to start is familiarize yourself with the cards that you have,

00:12:08.620 | how can you use those cards a little bit better. And I think when you look at it that way of what

00:12:13.560 | is just the one next skill or one next aspect of earning points or redeeming points, that is going

00:12:19.840 | to be the highest value for me. Once you start there, then you've removed that expectation that you're

00:12:25.260 | going to try to learn or execute or be expert at 100 things all at once. And then every time you take a

00:12:31.280 | step forward, I think it's so important to really, really acknowledge for yourself. Wow, I just learned

00:12:37.560 | one thing. I think we have this tendency to downplay it, right? Like, oh, well,

00:12:41.400 | I learned how to use an Amex personal gold card to get more points on my grocery spend than what I was

00:12:47.380 | getting before. And we say, but that's not that big a deal. Because look at all these other things I

00:12:51.600 | don't know yet. And I think that that's a really big mistake. And I think what we need to do is not

00:12:55.580 | compare where are we standing today with what is that ideal goal? What if I was like Chris, you know,

00:13:00.920 | with my points and miles? Instead, you have to compare yourself to where you are coming from. And I think that is

00:13:06.420 | one of the ways that you can really, really actionably begin to move from that valley of

00:13:11.600 | despair from feeling terrible, or overwhelmed about points and miles to really truly beginning to build

00:13:16.720 | up your skill. And as a byproduct of that your confidence and how you feel about it is naturally

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00:15:36.080 | job for free and connect with top talent ready to help your business grow. It's funny because completely

00:15:41.600 | aside from points and miles, a couple weeks ago, we went to Colorado and I have snowboarded since early

00:15:48.720 | elementary school and I went to school in Colorado and I would say I have not found a run on a mountain where I didn't

00:15:56.320 | feel very competent in my and confident in my skills. Now, we were taking my two daughters who are under five and I

00:16:07.120 | thought two things. One, teaching kids how to ski is much easier on skis. And let's put aside the fact that I

00:16:15.680 | probably could have taught them how to snowboard, but let's just shelve that. And we were using these

00:16:19.600 | harnesses and it's just so hard to do on a snowboard. And I thought, well, why don't I just ski?

00:16:25.680 | Like, we're not going down these difficult runs. We're going down the easiest runs on the mountain.

00:16:30.560 | What if I rent some skis and we go and experience this? And thankfully, we were in Steamboat Springs,

00:16:35.680 | Colorado. And there is a massive, beautiful, huge resort. And then there's a local resort downtown

00:16:42.080 | that on all but Sundays is only $50 for adults and it was free for the kids. And then on Sundays was free

00:16:48.240 | for everyone. So I rented some skis. Now, I wouldn't advise anyone learning to ski for the first time to

00:16:55.120 | try and also take their toddler on the chairlift. But first time off the chairlift, both of us fell,

00:17:01.680 | slid down. And I was like, I went into this thinking, how hard could this be? Well, first

00:17:07.680 | of all, I never even thought about skiing. It didn't even cross my mind. I was totally fine

00:17:11.040 | that I didn't know how to ski. And we went for two or three days and it was just brutal the first day.

00:17:19.120 | And at one point I was like, maybe now I'm good enough to help my daughter. And all of a sudden,

00:17:24.000 | she's going down and I can't control her and I'm falling over. And it's like, I went from a very

00:17:29.920 | competent snowboarder to an absolute clown. I wanted to video some of the kids, but I was like,

00:17:36.560 | I have to focus so hard on skiing that I can't even make a video. Whereas on a snowboard,

00:17:42.720 | it would be just be completely unconscious. It was just so easy to do. And so I just stuck at it.

00:17:48.640 | And to make everything worse, my kids are progressing incredibly fast. My nephews are like

00:17:56.080 | pros jumping off the sides of the mountain. And over two days though, I could feel the confidence.

00:18:03.680 | And I think unfortunately, something like skiing, it's very easy after 10 runs to be like, wow,

00:18:11.120 | I came down this mountain better than I did before. And there was no part of me that thought,

00:18:18.480 | but why can't I go down that mogul run over there? No part of me was looking at that run thinking,

00:18:24.400 | I wish that I could do that at this stage. But in the points of miles world, it's so easy to see

00:18:30.320 | someone redeeming around the world ticket in business class for four people, which is the

00:18:35.360 | equivalent of that double black run with moguls and think, I want to do that right now. And I don't

00:18:41.200 | know why, but it just made me think, why is it so much harder for someone learning a skill that's online,

00:18:49.120 | that is less physical to be comfortable not trying the really hard thing out the gates. Whereas for me,

00:18:58.000 | know, it was so easy. In fact, by the last run, my nephew was like, let's just try this easy black run on on day

00:19:06.000 | two of skiing of my, you know, my life. And I regret doing that. But but I had no injuries. So I guess it was okay.

00:19:13.920 | Yeah, I think too. It's so fascinating your experience with the skiing where you're like,

00:19:18.960 | it didn't even occur to me to say, Oh, my gosh, after, you know, five minutes, yeah, let me go jump on this incredibly grueling,

00:19:23.600 | potentially physically dangerous course based on your current level of skill set. But when we're learning

00:19:28.000 | something like points and miles, you know, I think a little bit of it is just that bias of what we're

00:19:33.760 | all just exposed to, on the internet, you know, on podcasts, maybe from our friends, if they're really

00:19:39.280 | active in points and miles. And I think that a lot of times, like, what is fancy, what's exciting,

00:19:44.960 | right? It is those stories. It's those stories that are at the far end of the spectrum in terms

00:19:49.600 | of somebody's ability or interest or expertise or skill level, where we say as someone, you know,

00:19:56.080 | who's learning a new thing, well, I want that, right. But I love your analogy so much. And I actually think

00:20:01.600 | how much better would a lot of our learning experiences be if we held that example in our

00:20:07.200 | mind, you know, to go from very beginner to very, very expert overnight, maybe I can just release that

00:20:14.320 | expectation of myself. Now we're climbing this this slope of enlightenment as it as it's called.

00:20:20.240 | And what is the process of going up that slope kind of stage three to getting to the final stage?

00:20:27.520 | Yeah, so I think the best feeling transition when you're learning a skill is when you move from that

00:20:32.560 | second stage, the valley of despair, where you are consciously incompetent, to then that slope of

00:20:38.000 | enlightenment, where your confidence goes up, your competence goes up, you're consciously competent.

00:20:42.880 | That is that transition where you start to see, oh, wait a minute, I am actually doing better,

00:20:47.360 | and I feel better. But that's not the actual endpoint of learning or skill or confidence. That third

00:20:53.040 | phase, when you're consciously competent, you are better at this skill, but it still requires

00:20:57.440 | a lot of energy and focus and attention. Maybe you're getting a little bit more skilled

00:21:02.000 | at using more than one rewards credit card and really deliberately and strategically picking,

00:21:06.560 | which is the one I'm going to use for any given expense, because I know it's going to give me the

00:21:10.720 | highest bonus points earning for this activity, or maybe you're starting to learn how to do stacking,

00:21:15.680 | right? So you already feel really confident with which credit cards you're using. But now you also

00:21:21.120 | want to say, how can I optimize and maximize my points are even earning even more, maybe I'm also going to

00:21:26.000 | utilize an online shopping portal. But the whole point is that when you're in that third phase of

00:21:30.960 | learning, it still requires a lot of deliberate focus and attention. So nothing is really automatic yet.

00:21:36.720 | But you can see that when you are paying a lot of attention, when you are trying to, you know, remind

00:21:43.200 | yourself, what am I not supposed to forget, you know, at this stage, wow, you're getting a lot better at it.

00:21:47.440 | And then what happens as you continue to just learn more, and practice more things you do over

00:21:53.360 | and over again become routine things that you once had to pay a lot of attention and focus and energy

00:21:58.400 | to in order to do it well, they become unconscious for you. And I think this is the step that so many of

00:22:05.920 | us aspire to get to, we want to get to the place where points and miles feels easy, right where we

00:22:11.440 | can walk around with 10 cards in our wallet, and we know exactly which one is going to be best for any

00:22:16.720 | specific expense, where it is easy to sit down in front of your computer and say, I want to take you

00:22:21.760 | know, my family of three from point A to point B, I actually know exactly where to look to find the

00:22:26.080 | best deal, I know automatically whether or not a given points rate for an award flight is a good

00:22:32.000 | deal or a bad deal. All of these things become easy and very routine over time, only as a reflection

00:22:39.840 | of the amount of times that you've practiced it. And so, so many of us that want to get to that stage of

00:22:46.160 | unconsciously competent, what I want you to hear and understand is, we are all on our way there,

00:22:52.720 | we don't get there at our as our second step, unfortunately, but if you continue to learn,

00:22:58.160 | if you continue to practice, then a lot of these things that require a lot of energy or a lot of

00:23:03.200 | attention to do the first time or the second time, they become incredibly, incredibly easy over time.

00:23:09.520 | I'll just tell everyone, it never stops, right? I think about this for myself, and we're trying to

00:23:14.800 | book for four people now instead of two. And, you know, we're starting to plan farther and farther in

00:23:21.040 | advance. And, you know, we're planning a trip to Asia next year. And I'm like, I have to relearn this

00:23:27.200 | whole process because we were always just booking last minute. Now we're starting to learn about when

00:23:32.400 | do schedules open, what airlines release, how many seats at the certain days, these are all new things

00:23:36.800 | to me. And then the other thing I just want to remind everyone listening is that sometimes I'll do

00:23:41.760 | an episode and I'll talk about how I did a thing. And I've probably spent 30 or 40 hours going deep

00:23:48.480 | on that thing before I talk about it. And so hopefully two things are true. One, you know that,

00:23:54.480 | but two, hopefully some of my synthesis saves you the time of needing to go through some of that work.

00:24:00.240 | But it doesn't mean that it's always going to make sense. You might need to practice it,

00:24:03.200 | you might need to approach it practically, you might need to, you know, do some reps.

00:24:06.880 | But one thing I think would be really fun to do is there are a handful of areas that I know you've

00:24:12.240 | dealt with that as we think about that, that slope in stage three, getting to stage four, maybe we could

00:24:18.800 | spend the second half of this kind of running through a few areas and hearing some of your learnings.

00:24:24.640 | I can jump in if I have any, uh, in various areas that will help people kind of build a little bit

00:24:29.680 | of knowledge from the experience you've had. Yeah, I think that's great. And I think the other thing

00:24:34.160 | that is always fun to do is I think there can be this misunderstanding that if someone does seem

00:24:40.720 | like they're good at something that they made no mistakes along the way. And I think that that is

00:24:45.200 | entirely untrue. Like you said, you may have spent 30, 40 hours researching something before you actually

00:24:49.840 | present it to your audience. I know the reason that I can relate to people who sometimes find

00:24:55.120 | points and miles hard, especially in the beginning is because I've made so many mistakes in this hobby.

00:25:00.000 | I continue to make mistakes in this hobby. And I think that that really helps to remind folks that,

00:25:05.280 | oh, wait a minute, this is not, uh, you know, like you start on one day, you learn a couple of facts,

00:25:10.960 | and then you do everything right from there on out. So absolutely. Let's kind of walk through what

00:25:14.880 | you think is going to be the most high yield for everybody.

00:25:16.640 | I'll give you the one example from just two days ago where I had that exact thing. I was looking

00:25:21.440 | for a flight. I was trying to book something from the US to Europe. And I was like, well,

00:25:26.160 | it's this many points on British Airways. And then I saw it pop up on Alaska. And I was like,

00:25:31.040 | oh my gosh, it's even cheaper. And I booked it. And I was like, wait, I didn't, I didn't check American.

00:25:35.360 | And then I looked and American had, I was already in the checkout flow. I'd already booked it.

00:25:41.520 | The price on American was like 20% less. I had miles there, but there was only one seat

00:25:46.320 | and it was too late. I couldn't book it using the cheaper option because I'd already used the seat.

00:25:52.000 | And I was like, I could cancel it and hope it goes back, but will it? And so I'm messing up all the

00:25:57.840 | time still. Like I, you know, sometimes that's, I got excited. I didn't think to look somewhere else.

00:26:01.840 | But one thing that helped me was I looked at it and said, well, this is still a way better deal than I

00:26:07.200 | would have gotten otherwise. Could it have been 20% better? Absolutely. Did I even look if there

00:26:11.840 | was some shopping portal that I could have added? A lot of times, no. I had a conversation with my

00:26:16.480 | wife the other day. I was looking at expenses. I was like, you know, I looked at this purchase and

00:26:20.560 | I was like, was that you? And she's like, yeah. I was like, do you look at buying any gift cards

00:26:24.560 | for that? Because they would have been like 15% off. And she's like, no, I forgot. And we forget all

00:26:30.720 | the time. So I might share the stories that are most relevant to people to save and maximize.

00:26:37.280 | But I probably could also share some of the stories where, you know, we didn't take the advice that we

00:26:43.840 | talked about, you know, in the episode of the week, we just forgot, we missed, we were moving too fast.

00:26:48.880 | And, and I think that happens to all of us. So you just mentioned high yield, like,

00:26:52.560 | what are some of these high yield opportunities that you often talk about when it comes to maximizing?

00:26:57.760 | And, you know, how do you find them? So, you know, in terms of high yield things,

00:27:03.040 | I think, again, my approach to earning points might not look like everybody's, I think there are people

00:27:08.000 | for whom always trying to have a brand new card open, so they can put all their expenses on that

00:27:13.520 | card. So they can always be working towards a welcome bonus. I think if that is the scenario,

00:27:17.600 | that's most high yield for you, I think that makes so much sense. I very rarely open new cards now.

00:27:22.400 | And part of it is, I've been doing this for a long time. So I have all of the cards I consider to be

00:27:26.400 | actually, actual foundational points earning cards that I want to use on a regular basis,

00:27:31.200 | but also because it no longer makes sense for me to constantly be trying to open cards. And so

00:27:37.280 | I think the first step is really looking at, again, what, where am I going to get kind of,

00:27:42.720 | no pun intended, the biggest bang for my buck. And so for me right now, it's things like having

00:27:48.400 | credit cards that give me really, really great bonus points earning for my everyday suspense

00:27:53.760 | spend when I'm not actually working on a welcome bonus. And so I have personal cards, I have business

00:28:00.000 | cards. And part of that too, is also looking at what are the points currencies when you are ready to kind

00:28:05.600 | of expand beyond one type of points currency. If you feel like you're in the phase where you're ready to

00:28:10.400 | get into a second or a third points currency, at any given time, what is the highest yield points

00:28:15.440 | currency that I'm trying to earn? Because I think people can get very, very kind of confused or in

00:28:21.040 | the weeds when they do start to have more credit cards and saying, wow, I've got five different

00:28:25.040 | options of cards that I could use for this one particular expense. How do I prioritize it? Should

00:28:29.520 | I prioritize that just card a gives me more points than any other card? And I think that's one way to do it.

00:28:35.440 | But I think it's also really valid to ask, huh, for what I want to do with my points right now,

00:28:40.560 | what's going to be the highest yield for me? So being really comfortable, not always doing again,

00:28:46.480 | whatever you think everybody else is doing with their cards, but being really clear on what are

00:28:51.200 | you trying to accomplish? And then what are the tools you have available to you that's going to

00:28:54.800 | help you accomplish that? Yeah, I think about this a lot of times. And you know, I recently opened up a

00:29:00.880 | city card. And I have a little bit of a struggle here, because I just wanted to get into the

00:29:05.360 | city ecosystem. I hadn't been able to talk about it on the podcast. So I probably have a business

00:29:09.360 | reason to go. But now I'm like, oh, this card might be better for this purchase. But I don't

00:29:14.560 | have enough city points to really do anything. Versus if I put them somewhere else, they can

00:29:18.880 | contribute towards a trip. Now, I think that's just an example of there might be some card that

00:29:24.720 | earns an obscure amount of points that's higher than other things. But if you don't spend enough in

00:29:29.440 | that category for that total number of points accumulated to be meaningful, or if you're going to earn

00:29:35.280 | some obscure number of Wyndham points on gas, but you don't even need Wyndham, or your total

00:29:41.520 | gas spend is small enough that it's not enough to even book a vacation, think about whether that

00:29:46.240 | matters. So I like that approach. And let's get really tactical with a few things. You mentioned

00:29:53.600 | earlier, paying a fee towards using your credit card. Let's talk about that and break that down,

00:30:00.320 | because I get a lot of questions about that. Especially right now. It's around tax time.

00:30:05.120 | But but I don't know if this will come out before the 15th. So broader than that.

00:30:09.280 | What what how do you think about that decision?

00:30:12.240 | Yeah, I love thinking about this so much. And again, as I will probably preface everything I say,

00:30:18.400 | it's that you always want to hear whatever it is that someone offers, and then put it on yourself and

00:30:23.760 | say, Okay, does this actually apply to me? Is this useful for me? Because the answer may be no.

00:30:27.840 | And when I think about certain expenses, in my life, the expenses that I think offer oftentimes

00:30:36.000 | really, really amazing points earning opportunities, because they tend to be high, usually one time,

00:30:41.680 | or only a few times a year expenses are ones that don't take a credit card directly without my having

00:30:48.080 | to pay a processing fee. So in my life, this looks like things like tax payments, my husband and I are

00:30:52.800 | both self employed, we have the lovely advantage of having quarterly tax payments. So we're paying taxes,

00:30:57.600 | you know, every couple of months. And when we look at the things we spend money on over the year,

00:31:01.680 | our tax payments are probably our single highest expense category compared to something like

00:31:06.960 | dining out, you know, or compared to something like even online shopping. And so one of the things that

00:31:12.000 | I think is helpful is to first look at, in your life, do you have expenses, where you could pay them

00:31:17.520 | with a credit card, but they would incur a processing fee in order to do so, and get a very good sense of,

00:31:23.440 | okay, but what impact would that make on your overall points earning landscape, if you could earn points

00:31:28.720 | for that, right? Is that 1% of your overall annual spend? Or is this a significant amount of your annual

00:31:34.080 | spend? Because for folks who have a significant amount of annual spend, whether it's personal

00:31:38.800 | or business spend, or both, where they could pay with a credit card, but would have to pay a processing

00:31:43.440 | fee. I think that's the first question that needs to be answered. Like, what is the impact of this going

00:31:47.440 | to be right? I love to optimize points, but I am not a maximizer, I will not chase every single points

00:31:53.600 | earning opportunity, it has to be high yield. And so first, you want to get a general idea of what is

00:31:58.400 | the scope of the yield of this activity going to be. So other things that I know folks can pay using

00:32:03.040 | a credit card, but also get charged a processing fee that could potentially be very high yield

00:32:07.760 | points earning opportunities for them. Many, many people, if you have children, and they're in a

00:32:11.920 | daycare, perhaps they go to a school that has a tuition, maybe there is some sort of activity that

00:32:17.840 | a child is involved in. In my area, there's a lot of summer camps that people could theoretically send

00:32:22.640 | their children to the camps charge a processing fee in order for you to enroll your kids in them using a

00:32:28.640 | credit card. You know, we can talk about other opportunities, too. There are a lot of vendors

00:32:32.960 | or services that may not accept a credit card outright. And so you may be looking into a payment

00:32:38.960 | platform, something like plastique, or milio or zill money that basically allows you to pay a specific

00:32:45.920 | service or vendor. And then you have to pay them, you know, processing fee, so that you have the luxury

00:32:51.520 | of using your credit card. So one of the first things that I always want to look at is for any given single

00:32:57.120 | big expense. And we'll take the tax payments as an example. But again, this could be daycare,

00:33:01.280 | it could be tuition, could be you're doing a home renovation, and your contractor does not accept

00:33:06.320 | your American Express business platinum card, and you want to earn the sub. So you want to go through

00:33:10.880 | one of these payment processing platforms. The first thing I always look at is what is the actual amount

00:33:15.520 | of this expense itself, you always, always want to know what is the exact processing fee that you are

00:33:20.960 | going to be charged if you do want to pay by credit card, because this can vary, right?

00:33:25.520 | Sometimes it can be something like 1.7% or 1.8%. Depending on the service or vendor that you're

00:33:32.080 | using, it can be much higher, it can be 2.9% or over 3%. But you have to know what that processing fee

00:33:37.840 | is, because you are going to pay that percentage of your total bill amount, in addition to your total

00:33:44.560 | bill amount. So let's just pretend you know, you have a $10,000 bill that you want to pay. And the processing

00:33:50.720 | fee that you would have to pay in order to use your credit card is 2%. Right? So you're not just

00:33:56.160 | paying your $10,000 bill, you're paying $10,000 plus the 2% processing fee. So once you know that,

00:34:02.080 | you know, the total amount of points that you would theoretically earn for this expense. But here's,

00:34:07.040 | for me, the critical part of evaluation is that I don't think any of us would ever consider using a

00:34:12.800 | credit card to earn points and pay a processing fee, if we were not going to come out net positive on the

00:34:17.360 | other end, right? None of us wants to just spend money that we don't have to spend. So the question

00:34:21.440 | is always going to be the number of points that I earn by using my credit card for this expense.

00:34:26.880 | Am I going to get significantly more value out of these points out of the way I use them,

00:34:31.520 | then the cash cost of that processing fee. And this is where the answer is going to be variable. I do not

00:34:37.840 | recommend for folks who are beginning in this hobby to take this approach because I think it's very

00:34:43.200 | challenging for them to be able to break even and my ideal is not to break even it's actually do much

00:34:49.200 | better in terms of the value of these points. But for people who are feeling a little bit more

00:34:53.120 | comfortable, maybe they're a little bit more experienced in using their points, you look at the total number

00:34:57.760 | of points that you would have earned for that expense. And you probably have a sense of how much value do you

00:35:03.280 | tend to get out of your points, right? If you're only using your points to book travel through a credit card portal,

00:35:08.560 | that may look like something like one to one and a half cents per point. I'm not saying that's a terrible

00:35:13.200 | use. But that's why you have to know what percentage fee are you paying? What is the actual cash cost of

00:35:18.240 | that processing fee? Are you going to do better than break even, you know, one to 1.5 cents per point,

00:35:23.360 | you're probably not going to. But let's say that you feel a little bit more experienced using your

00:35:28.960 | points. If you're really confident that you know how to use your points, you're familiar with transfer

00:35:33.520 | partners, you know, you're really comfortable searching for award flights, let's say, and you

00:35:37.840 | feel pretty confident that you're going to be able to get four or five cents per point or more out of

00:35:42.880 | your points, that can be so much more value than the cost of the processing fee. But the last little

00:35:49.200 | variable that you always want to take into consideration as well is when we're paying any

00:35:53.360 | expense by credit card, of course, we have tons of options of what card do we want to use to pay

00:35:58.080 | that expense. And we have cards, of course, they give us different levels of return on our spend.

00:36:04.800 | So the other thing that you need to know is not just what is the cost of the bill and what is the cost

00:36:09.600 | of the processing fee, but in terms of the number of points you could potentially earn, that's going

00:36:14.000 | to depend on the card you use and its earning rate. So are you going to be using a card that earns

00:36:18.560 | one point per dollar spent and only earn effectively one point for your expense when you're doing this?

00:36:25.680 | Or do you have a card that actually offers you one point five or two points for every dollar you

00:36:30.480 | spend? You know, interestingly, some of these payment platforms that I talked about, depending

00:36:34.400 | on which ones you use, and which card you use, you can actually get three points per dollar spent,

00:36:39.680 | you know, if you're using a payment platform that codes as shipping, and you have a business card that

00:36:44.960 | has a shipping bonus category, potentially, you're going to be earning three points for every dollar you

00:36:48.960 | spend on that expense, and especially want to factor in if you are going to be able to earn a welcome

00:36:53.280 | bonus by paying that expense as well. And so I think for everybody, one of the things that I

00:36:59.200 | think is really important, the more you get into this hobby is to realize that there's probably some

00:37:04.160 | foundational kind of basic teaching and guidance on everything in points and miles. I think it's great

00:37:10.320 | to learn that first. And then you can start looking at the nuances, then you can start looking at the

00:37:16.160 | exceptions. So I never tell people, you should always pay a processing fee in order to use your

00:37:21.840 | points just because a lot of times I do. I also don't tell people you should never pay a processing

00:37:27.120 | fee in order to use points. Because I don't actually think that's true either. I think what makes a lot of

00:37:31.600 | sense is start with what is kind of the safest, most conservative approach you can take. And then when you

00:37:38.880 | kind of understand the basics of this, and you can understand how to evaluate it for your own personal

00:37:43.360 | scenario, then you can start looking for those exceptions. And so it starts with math, but it

00:37:48.800 | also comes back to what are your goals? And what is your comfort level in earning and using points?

00:37:53.920 | I love that. There's two things. One, to the extent that this is a question related to a business,

00:37:59.760 | it is often that that processing fee could be treated as a business expense. So keep that in mind for any

00:38:05.040 | business owners. But two, since I'm guessing you've done this a few times, are any of the more common,

00:38:11.360 | you mentioned plastic, milio, do any of those transactions actually code as anything interesting

00:38:17.840 | that earns multiples? Yeah. And that's why I think this is so valuable to know. And also take this with

00:38:22.480 | like a huge boulder of salt. Because if you've been in the points and miles world, you're probably aware

00:38:27.440 | that this is a very dynamic landscape, things can and do change overnight. So one thing I always,

00:38:33.200 | always, always tell people is, if you hear something that I'm about to say, if you hear

00:38:37.280 | something on another, you know, platform, please do your due diligence and double check because these

00:38:42.640 | are the types of things that can change overnight. So as of the time that we're recording this,

00:38:47.520 | I have been told I have not tried this personally, but I run a Facebook group of about 28,000 people.

00:38:52.000 | So we have some good data points in there that Plastique, which is one of these online payment

00:38:57.040 | platforms that it can code when you use specifically the chasing business preferred card. This is one of

00:39:03.520 | several chasing business cards that chase offers. The chasing business preferred card has shipping as one

00:39:09.440 | of its bonus categories, you can earn three times points on it, up to about I think $150,000 spent over

00:39:15.760 | a calendar year. So again, for business owners, this can be a really great option for a card to have,

00:39:21.120 | I have been told that Plastique can code as shipping, even when the vendor the service that you are trying

00:39:26.560 | to pay is not FedEx or is not UPS. And so that can be a very interesting way to leverage your shipping

00:39:33.040 | bonus category on chase. Now, the third platform that I mentioned is called Zill monies, Z I L money.

00:39:40.960 | This is specifically for business owners. It's a really fascinating payment platform. It is probably

00:39:46.320 | the most dynamic one. And I mean, changes all the time. So by the time we even finished recording this

00:39:51.760 | conversation, this may be different. For a little while, Zill money was coding also is shipping, meaning that you

00:39:58.320 | that you could earn 3x using your chase Inc business preferred card. And Zill money is a fascinating

00:40:03.440 | platform because not only does it allow businesses to pay services or vendors for their business,

00:40:07.760 | you can pay payroll for your business through Zill money, you can pay commercial rent for your business

00:40:13.680 | through Zill money. So some of these expenses that some business owners may be encountering that right

00:40:18.880 | now we don't have a lot of other avenues to easily earn points like we love built right for residential

00:40:24.080 | rent. Most business owners cannot get away with paying commercial rent on their built card to earn

00:40:29.600 | points. And so it is always really fascinating to find out about some of these avenues for points

00:40:34.080 | earning. And also, I want to throw it again as a word of caution, just because it worked today or it

00:40:39.280 | worked yesterday may not guarantee that it works another time. But that is an example of a way that you can

00:40:44.080 | really leverage one specific bonus category on a credit card for some of these payment processors.

00:40:49.920 | Yeah, I have not played with Zill. But given the fact that we have a business and we have expenses,

00:40:56.880 | if you treat an expense as a deductible expense, the fees often are lowered enough that you really

00:41:05.600 | could make a case for putting 100% of your expenses on a credit card. I haven't played with the payroll

00:41:10.880 | one yet. So we typically run our payroll like once a year. But I so I have some months to figure this

00:41:17.600 | out. But it's on the docket right now. This episode is brought to you by NetSuite. What does the future

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00:41:57.040 | backwards and more time planning for the future with actionable data, which is exactly what I'd want as a

00:42:03.200 | CEO. Speaking of opportunity, you can download the NetSuite CFO's guide to AI and machine learning at

00:42:08.880 | chrishutchins.com/netsuite. The guide is free. You can go to chrishutchins.com/netsuite or click

00:42:15.120 | the link in the description. This episode is brought to you by Built Rewards, which is an amazing points

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00:42:50.720 | points on rent, my question is why not? Start earning points on rent you're already paying by going to

00:42:56.400 | chrishutchins.com/built. That's chrishutchins.com/built, B-I-L-T. Make sure to use our URL so they know

00:43:04.320 | we sent you chrishutchins.com/built or the link in the description to start earning points on your rent

00:43:10.000 | payments today. Okay, so I generally adhere to a similar philosophy of trying to make sure you're earning

00:43:15.840 | enough to make it worth paying this fee. The tax payment fee has gone down. So it's among

00:43:21.520 | one of the most reasonable. In a way, you could argue that you're kind of buying points. And so if

00:43:26.880 | you figure out the rate at which you're buying, you can figure out whether the rate at which

00:43:30.160 | you're earning them makes sense. You've talked about how you took a couple trips with children.

00:43:35.680 | One of the questions I get a lot is how does this game change when you have multiple people?

00:43:41.200 | And now when I'm looking for flights with four people, it's gotten so hard. So I'm wondering if

00:43:47.600 | you are a few years ahead of me in that process, how do people looking for three, four, or more seats

00:43:54.560 | start to better be able to take advantage of award travel, especially if they're looking for premium cabins?

00:44:00.880 | Absolutely. And I was actually going to couch this entire answer, like with that caveat specifically,

00:44:05.280 | I think if your priority is to find economy seats for domestic or international flights,

00:44:09.920 | you are going to have an easier time than if your preference is to find international premium cabins.

00:44:15.360 | So I'm not even going to talk about first class because oftentimes you are not reliably easily going

00:44:20.080 | to be able to find more than one first class award seat on many international airlines, but

00:44:24.400 | business class is possible. It's definitely not as easy as if you are a solo traveler or traveling with

00:44:30.240 | two people, but it is definitely possible. So I will kind of tell you what my approach has been,

00:44:36.080 | which again, sometimes it works and sometimes it's a little bit less reliable, but it's a really good

00:44:40.400 | starting point. So first things first, you know, we talk a lot in award travel about when it comes to

00:44:45.440 | getting potentially as much value as you can from your points, using them to transfer them out of your

00:44:51.360 | transferable points currencies and into specifically airline transfer partner accounts for flights,

00:44:56.320 | that there is so much importance that we place on flexibility, right? That you need to be aware of

00:45:02.640 | kind of what are your zones of flexibility, because you might be able to get a lot of what you want, but you

00:45:07.360 | probably are not going to be able to get everything you want. And what I mean by that is, if you're looking

00:45:11.120 | for multiple premium cabin international flights, you may not be able to say I want to fly on these specific

00:45:16.320 | days, these specific Saturdays, right around my kids spring break, or my kids winter break, you know,

00:45:21.200 | you may not be able to say, Hey, I want to fly from my local airport all the way to my destination.

00:45:26.800 | And I'm not willing to look at any other departure airport, especially if your local airport happens

00:45:31.280 | to be more local or more regional. And you may not get the best absolute bargain basement deal price.

00:45:38.160 | If your priority is to find, you know, four or five or even six premium cabin flights together. So the

00:45:44.560 | first thing is actually not strategy in terms of go to this airline or do this thing. It's I always

00:45:49.920 | really recommend to people know where you can be flexible and know where you can't be. You don't

00:45:53.840 | have to be infinitely flexible, but you do have to be aware of where are you willing to bend if it's the

00:45:58.800 | difference between finding a good flight option and no flight option. And for me, what that looks like

00:46:04.960 | is I'm lucky. My local airport is a huge international airport. So I naturally have a

00:46:09.440 | lot of options for international flights, but I have a family of four. And when we travel with our kids,

00:46:14.880 | we do try to travel around their spring break, their winter break, when many other people are traveling

00:46:19.760 | and probably want to go to similar places that we want to go. And so inventory may not be very high.

00:46:24.720 | And so first of all, along with flexibility is I tell people, if you can, I get it. Maybe it's a

00:46:30.880 | milestone trip, or maybe you just don't want to be flexible about your destination and you want to go

00:46:35.120 | to one specific place. I can understand that. But if you do not have your heart set on one specific place,

00:46:40.640 | then allow yourself to follow where some of the best opportunities are instead of saying,

00:46:46.160 | Oh, I know I specifically only want to go to destination a for this trip, because award

00:46:51.520 | availability can and will fluctuate. There can be times there's no award availability,

00:46:55.520 | let's say to Japan that has been so insanely popular recently. But you can actually find award

00:47:00.480 | availability to somewhere else that you would also love to go. And then let's talk about actual tips,

00:47:06.160 | actual strategies, where to look. I think there are certain airlines that reliably have more business

00:47:12.560 | class, especially award space than other airlines. And so I think it's best start where you have the

00:47:17.360 | highest chances of success. That used to be Air France flying blue, especially for flights between

00:47:22.800 | North America and Europe. They used to have amazing award availability for multiple people in business

00:47:27.600 | class. One discouraging trend this year is that that has not been the case recently. And so now I'm

00:47:33.840 | telling people, okay, don't depend on Air France flying blue to get your family to Europe. But there are

00:47:38.720 | other airlines that do still reliably have multiple business class awards that are available. And so

00:47:43.760 | maybe just the fact that these are available will help determine where you're willing to go. So one

00:47:48.240 | airline that tends to have really, really good award availability on specific routes is Emirates. So

00:47:53.840 | Emirates is an amazing airline is based in Dubai. Maybe you never thought about going to Dubai. It's an

00:47:58.560 | incredible city. But specifically on flights that Emirates operates that don't start or end in Dubai,

00:48:05.600 | there is amazing award availability. So these are known as fifth freedom flights, they actually operate

00:48:10.560 | I think three, they operate four from North America. A lot of people are familiar with the routes that fly out of

00:48:16.960 | the New York area. So Emirates operates a flight from JFK specifically to Milan. They also operate a flight from

00:48:23.200 | Newark to Athens. So people are familiar with that, that can have amazing award availability over to Europe. But one of the

00:48:30.480 | the fifth freedom flights that I think is underrated underutilized for getting to Europe, especially

00:48:34.800 | depending on where you're based in the United States, is that Emirates operates a fifth freedom flight that

00:48:39.520 | leaves out of Mexico City, and flies directly to Barcelona has amazing award availability in terms of the

00:48:45.200 | number of seats they make available to book using points. And with Emirates, if you're booking round trip,

00:48:50.960 | specifically, the points price of those flights can be incredibly, incredibly competitive. So that is one

00:48:57.120 | airline that I think it makes sense to actually price flights out round trip rather than looking

00:49:00.560 | at them as one ways. But Emirates can be fantastic for families. And again, if your goal is to get to

00:49:05.920 | Europe, okay, great, maybe you fly if you're East Coast based, maybe you fly to Milan or Athens, and then

00:49:11.280 | separately, you take a train somewhere or a more, you know, local or regional flight, you don't have to get to

00:49:16.080 | your end destination all in one go. But another airline that I love in terms of award availability,

00:49:21.280 | this is another one for folks who are interested in going to Europe is Condor Airlines. And that's

00:49:25.920 | an airline that not a lot of people talk about a lot. It's based in Frankfurt, it used to be more of a

00:49:31.760 | leisure kind of airline versus, you know, a heavy business type of airline, but they have incredible

00:49:38.160 | routes. If you look at the number of airports that are serviced in the United States by Condor,

00:49:42.320 | I think you would be shocked because it's not just the huge big international airports you would expect like

00:49:47.520 | JFK and you know, Chicago, things like that. They also service a couple of smaller regional airports. They

00:49:53.600 | have amazing award availability through Alaska Airlines, not only good award availability, but good award

00:49:59.120 | availability for multiple people. And this can often be the crux for families or for groups. You know, it's great if an airline

00:50:05.920 | releases one business class award seat. But if you're a family of four, especially if you've little kids who need

00:50:10.880 | supervision, it doesn't matter if there's one award seat, you can't book it for anyone in your party.

00:50:16.160 | So knowing where some of these high yield places to find multiple business class awards can be great.

00:50:21.200 | And so Condor, I recommend to so many people trying to get to Europe, and they've got a great route

00:50:26.080 | network even beyond just their base in Frankfurt. It was one of the airlines my family took when we,

00:50:31.760 | the family of four, took a trip to the Maldives just a couple months ago. We flew on Condor from

00:50:36.400 | Frankfurt to Malay. Fantastic use of points.

00:50:39.680 | The one thing I'll add on Condor, a lot of people hear Alaska and think, okay, well, I don't have

00:50:44.640 | Alaska miles. Yes, you can get there from built, but I don't have a lot of built points. At least right

00:50:49.680 | now, you can transfer from Amex to Hawaiian. And no one knows how long Amex will allow transfers to

00:50:56.240 | Hawaiian after the Hawaiian-Alaska merger completes. But for now, you can transfer up to 999,000 Amex

00:51:04.960 | points at a time to Hawaiian and move them over to Alaska. We just did one transfer and cashed out that

00:51:11.200 | full amount, 999,000, because I've just been seeing more and more incredible uses of Alaska points.

00:51:17.920 | It's how we got to Iceland last year. It's how we are getting to Hawaii on Hawaiian. And we've seen

00:51:24.240 | these Condor flights for flights this summer. And so, if you're sitting on a stash of Amex points,

00:51:31.120 | I normally don't like to speculate. And when I do, I normally like to speculate with huge transfer

00:51:37.200 | bonuses. But transferring from Amex to Hawaiian and thus to Alaska has been a speculation that,

00:51:44.720 | I have a lot of Amex points, just to be clear, so it's not like I'm burning all of them. But I think we

00:51:50.640 | put about a big chunk, a double-digit percentage of Amex points into Alaska this year because of that

00:51:57.520 | opportunity. I'm so glad you brought that up because I wholeheartedly agree with you. Going

00:52:01.520 | back to the very first question that you asked me about, what are some of the things that I think

00:52:05.200 | are due with points that maybe aren't traditional? I'm all for speculative points transfers, again,

00:52:09.840 | with very, very certain parameters. I also speculatively transferred about a million of our

00:52:14.400 | Amex points way back in September when that pathway first opened up from Amex to Hawaiian and then

00:52:20.640 | Hawaiian to Alaska because I have not had access to Alaska miles easily from any other pathway.

00:52:26.800 | And they do have some really, really wonderful award redemption opportunities. And so I think

00:52:32.560 | that that can be, again, for certain people under the right circumstances, a great use of points.

00:52:37.360 | But the last kind of idea I'll mention for people who are really looking for multiple premium business

00:52:42.720 | class award flights is if you are based on the West Coast or you don't have a problem getting to the

00:52:47.760 | West Coast, I love Singapore Airlines for their award availability. You know, they operate out of the

00:52:52.720 | major international hubs on the West Coast. They tend to have really, really fantastic award

00:52:58.240 | availability for multiple people. You may not be getting the absolute kind of quote,

00:53:02.880 | lowest price you could theoretically get for a given route by going through Singapore. But one of the

00:53:08.160 | things that I think we always have to take into consideration is, okay, if your priority is the

00:53:12.480 | is the lowest price possible, may not be your best option. But if your priority is I want multiple

00:53:17.840 | business class flights tickets together on the same flight, and that I can reliably find and not have

00:53:23.680 | to spend days or months, you know, tracking down manually a bunch of potential awards, Singapore is

00:53:29.520 | just a really great reliable place to go first. And so clearly, if you have an interest in Singapore,

00:53:34.640 | wonderful, that's their main main hub. They also operate a flight that you know about Chris that

00:53:39.040 | goes from LAX straight directly to Narita to Tokyo. So that can be a great option. I also recommend

00:53:45.440 | Singapore for a lot of people who are really interested in going to Australia or New Zealand

00:53:51.120 | to find a direct flight using points on business class for a competitive i.e. not extortionist points

00:53:57.600 | price directly from the US to New Zealand or directly to Australia from the US can be really,

00:54:03.760 | really, really challenging. And so if you are willing to be flexible and take a longer itinerary,

00:54:08.720 | getting to Australia, New Zealand from Singapore on Singapore Airlines can also be an incredible way to

00:54:15.760 | be able to make your points stretch pretty far and to have a wonderful flying experience when you're

00:54:20.800 | trying to go somewhere that's quite quite far away. So those are just some of the, you know,

00:54:25.600 | really specific places that I look that I recommend people look, because I think it can be very confusing,

00:54:31.200 | especially if you have multiple points currencies, maybe theoretically, you've got 25 airline transfer

00:54:36.240 | partners that you have access to that doesn't mean that all 25 of those potential airline partners

00:54:41.120 | are going to be high yield based on what specifically you're looking for.

00:54:44.720 | The one that we're kind of exploring, which I know you have a worksheet on that we can link in the show

00:54:49.680 | notes is when do airlines open up their schedules. And this is one where I had to start learning,

00:54:54.880 | because I didn't do this. But certain airlines might release award inventory reliably at the

00:55:02.000 | schedule open, but you might need to book it right when it opens. And so I can't off the top of my head

00:55:07.600 | talk about all of the airlines and their rules. But some airlines release things reliably. And so I know

00:55:14.000 | that Japan Airlines is pretty reliable at releasing two business class seats. So one of our plans is to

00:55:19.760 | book two business class seats on Japan Airlines for me and one child, my wife and another child,

00:55:25.600 | and they fly two flights a day to Tokyo. And so one of the things we're going to be willing to do to make

00:55:31.680 | this work, because instead of being flexible on route, we'd rather not be that we'd rather fly direct,

00:55:38.480 | but we're flexible that maybe we'll split up and take two flights. Then what we will do is we'll try

00:55:43.520 | to find an award search tool with alerts, set those alerts so that we have almost an entire year for

00:55:49.840 | two more seats to open up. So the other parenting kind of large family travel strategy is book something

00:55:57.920 | that's doable, and then set lots of alerts throughout the year to make it better. And so for us, we're going to book

00:56:06.400 | something we're okay with. For other people, it might be booking two seats in business class and two in premium

00:56:13.040 | economy. And you know, waiting to see if two more open up. So it's like no matter what we can get there. But this doesn't

00:56:20.000 | work. Booking a route that's less ideal, set the alerts and all that. And obviously setting alerts and using all these tools we've

00:56:26.640 | talked about in the past, it's it's another skill to learn. But I would encourage people that want to learn

00:56:31.920 | it. Even if you don't have a trip in mind, pick a route, set an alert and see what happens before you

00:56:36.720 | need it. And you can start to learn that that tactic. Absolutely. It's such a low pressure way to start

00:56:42.240 | really getting more comfortable with some of these approaches. I can tell you it can be quite stressful

00:56:46.400 | when you're actually in the heat of the moment when you know you're ready to book a trip, you have the points

00:56:50.800 | there. If you've never run one of these searches before. So do yourself a favor, right?

00:56:55.360 | Like how can you maximize your ability to be successful in this? I don't enjoy working under

00:57:00.800 | pressure. And so to take some time before a trip even exists in reality to say, hey, how could I

00:57:06.320 | potentially get you to this destination? What are some of the routes that I could be searching?

00:57:10.560 | It's so much more enjoyable to do that when you're not actually panicking that all those seats are

00:57:14.720 | actively getting booked up at that very moment when you need them. So I'm a huge fan of running practice

00:57:19.840 | searches. And you don't have to do this for hours on end. You know, you can do this for five minutes,

00:57:23.440 | for 10 minutes when you have little breaks in your day.

00:57:25.680 | Yeah. I also love volunteering my time sometimes to help friends because I don't mind telling my

00:57:32.000 | friends, hey, you wanted to go to Italy in the fall. Let me see if there's any award flights.

00:57:36.880 | And I'll look and I'll be like, couldn't find any. Sorry. Like this is, you know, for myself,

00:57:42.080 | if I can't find it, I'm stressed out. I want to try other ways, but at least for them, I can at least try.

00:57:47.360 | And if I find them something awesome, great. And if not, you know, then I can say, sorry,

00:57:52.320 | I didn't find anything. You know, here's the tool I used. You could try again later.

00:57:56.960 | And it's a little bit low pressure. I did an episode on all the award search tools

00:58:01.280 | with Greg from frequent miler. So I'll link to that in the show notes.

00:58:05.280 | One other one that I think we've talked about stacking and using shopping portals,

00:58:10.720 | but I loved how you talked about using Rakuten bulk ordering as a way to really maximize those returns.

00:58:16.960 | How do you how do you think about using Rakuten as a way to earn flexible points in really large quantities?

00:58:23.440 | I think this is going to depend on what is your actual reality? What is your scenario?

00:58:27.360 | Admittedly, my family is personal spend. We have high personal spend. My husband and I,

00:58:31.040 | we both own businesses. We have high business spend. So I feel like that is a luxury when you

00:58:35.120 | just have higher spend. It's easier to earn points, but you can still inject specific strategy into this.

00:58:40.000 | And one of the things I do, I love Rakuten. They pretty reliably have certain time

00:58:44.480 | points throughout the year when they will have really elevated bonuses on that shopping portal.

00:58:49.280 | They tend to be around traditional holidays. One of the most popular and reliable ones is,

00:58:53.920 | you know, that sort of end of the year holiday shopping period around Thanksgiving.

00:58:58.560 | That seems to be extending, you know, Black Friday, Cyber Monday, but

00:59:02.320 | you can usually expect to get 10, 15, 20 times points earning opportunities, you know,

00:59:06.560 | around that time of year from Rakuten. And so I'm also a planner. If there are things that I

00:59:12.160 | know I kind of need on a regular basis, but I don't need them immediately and they are not perishable,

00:59:16.880 | I will specifically just have, you know, like a note in my phone, a running note of things that I

00:59:21.760 | know I will want to buy by the end of the year. And as much as I can concentrate my buying of those things,

00:59:27.600 | when Rakuten is having a huge bonus, I will absolutely do that. You know, my kids grow.

00:59:32.320 | I know they're probably going to need snow boots every single year because we live in a place where

00:59:36.000 | it snows. I know they're probably going to need the next size up in clothing for a certain amount

00:59:39.920 | of clothes or for two bathing suits, you know, for the year. And so I'll just keep this running list.

00:59:44.560 | What are the things we need around the house? If there are things that I know we will get through

00:59:48.800 | in terms of inventory and they're not going to perish, so I can just keep them somewhere in my house,

00:59:54.080 | then we will go ahead and we will will strategically wait to buy things or buy multiples of things that

00:59:59.360 | we know we will get through at a certain point when we can really capitalize on those shopping portal

01:00:04.960 | payouts. And that can also be really helpful for trip planning for anybody who likes earning extra

01:00:10.640 | points through Rakuten. I've also seen this through Capital One Offers. If you have a Capital One

01:00:14.880 | points or miles earning credit card, you log into your account, scroll down to the bottom of that first

01:00:19.760 | page. And hopefully you'll see an area. This is Capital One Offers where you can actually shop at

01:00:24.720 | stores online and get rewarded in points. So this is totally different than the Capital One shopping

01:00:29.280 | portal that's actually rewarding you in cashback. Capital One, when they first started offering their

01:00:34.800 | offers, which was very recently, they had incredible points earning opportunities that were very competitive

01:00:41.200 | with Rakuten and actually out earned Rakuten for a lot of things like sixth car rental. You can get

01:00:46.240 | sometimes 30 times Capital One miles for a sixth car rental via tour, which is very popular also on Rakuten for

01:00:53.760 | booking tours or booking activities when you travel. My favorite thing is that you may have a trip planned out

01:00:59.120 | nine months from now. But if you're looking around on one of these shopping portals, and you see that via tour or

01:01:04.960 | sixth has a really, really high bonus offer at any given time, you can book a tour nine months out, right? You can book a car

01:01:12.240 | rental eight months out. And then when you're finished with your trip, you're still going to earn all of the

01:01:17.440 | points as of the day that you reserved that car or that activity. And so I think to the extent that someone

01:01:23.680 | enjoys or wants to be intentional about planning, there are ways that you can really turn some of

01:01:29.120 | these shopping portal offers into just thousands and thousands of points without it being super labor intensive.

01:01:36.240 | Yep. I've recently been playing around with save wise, which is another similar to cashback monitor,

01:01:43.360 | where you can kind of look at all of them, except they have alerts. And so we were in the market for

01:01:49.600 | a Peloton tread. And I just went in and said an alert when when some cashback or points earning opportunity

01:01:56.720 | crosses this threshold, let me know, because I'll go purchase it then. I think by the time this comes out,

01:02:02.720 | maybe I will have done an episode on that exact Peloton purchase and how we thought about it.

01:02:06.560 | But I did get an email from the founder of save wise. And I believe I have to check my email,

01:02:11.680 | but I think there is a promo code he gave for people who want to sign up. I will put it in the show notes

01:02:15.600 | if I find it. And, but it's, it's really cool that you can set alerts to be able to say, I know that I

01:02:22.240 | need to purchase from whatever the retailer, let me know when it crosses that threshold. I don't know

01:02:27.040 | if they have Capital One Miles, but I will find out. And if there is, then I'll definitely be setting

01:02:32.160 | alerts. And for people who missed it in the past times we've covered it, the reason Rakuten is so

01:02:37.600 | interesting is that you can link your Rakuten and your Amex membership rewards account.

01:02:41.680 | And instead of earning cashback, you can earn points. And so it might say 5% cashback,

01:02:48.480 | but that would be 5X Amex points. And, and like you, we have earned a ton of Rakuten powered Amex

01:02:56.400 | points by doing similar things, but I've never really kept the running list. And I'm like,

01:03:00.880 | we have two kids. They're going to need another, you know, a jacket, a snow boots, shoes, all this stuff.

01:03:06.400 | So I want to come up with a list. And I'm sure when my wife hears this episode, she's like,

01:03:10.240 | I'm going to make that list and we're just going to bulk order it. And, and we're probably going to

01:03:14.960 | buy, get the gift cards and stack the gift cards and all of those things. So I love that.

01:03:19.360 | Such a great point too, is that there are stacking opportunities. So it's not just,

01:03:23.520 | Oh, Rakuten might be 20 X for a store. It's like 20 X for the store, but then you can also,

01:03:27.760 | like you said, go out, get a gift card on discount or purchase a gift card for extra points from a

01:03:32.240 | different location and add those things together. And I think that's why it is so really interesting

01:03:38.560 | that there's so many different ways to earn points. It doesn't just have to be one way.

01:03:42.480 | And depending on what your spend patterns are, and also depending on your personality,

01:03:45.840 | where do you want to put time? Where do you want to put effort into certain things?

01:03:48.960 | You identify the ones that are the highest yield for you. And for sure, Rakuten Capital One offers,

01:03:53.600 | those have been enormously high yield for our points earning.

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01:05:02.080 | first box plus two months of salads for free. Any other final tips for people who fall into that

01:05:08.800 | camp of high earning, high spending that really want to optimize their earning and travel?

01:05:14.720 | Yes. I think one of the things, you know, in terms of the earning side of it is, I think there are so

01:05:19.920 | many things that people just automatically assume they can't earn points for. If they've had the

01:05:24.320 | experience where they go to pay for something and that service or vendor says, we don't accept credit

01:05:28.800 | card. A lot of folks in my community pay for things like malpractice insurance. They might be self-employed

01:05:32.960 | physicians or just other forms of insurance. What I want to say in terms of points earning is really be willing

01:05:39.200 | to challenge and be curious about any time you're spending money, especially for represents, you know,

01:05:44.240 | a decent amount of your monthly or your annual spend. If the vendor or the service says they don't accept

01:05:50.080 | a credit card, that may absolutely be true. But get really curious about what are alternate pathways where I

01:05:55.680 | could still use a credit card in order to pay this expense in order to earn points. And does that actually make

01:06:02.160 | sense for me? Is that actually justified? A lot of our points earning that comes over the course of a year,

01:06:06.560 | it's not from our online shopping. It's not from our groceries, even though, of course, we spend money

01:06:11.200 | on that, right? It's on these more single, but very, very high expense items that we have figured out these

01:06:16.880 | alternate pathways for earning points. So that is what I would say on points earning. And then on points

01:06:21.200 | redeeming, this is not a specific strategy. But this kind of ties into what we've been talking about

01:06:26.240 | this whole episode, which is that I think that there is conventional wisdom in terms of points

01:06:31.120 | earning, and points redeeming, that makes a lot of sense. And I know that sometimes people can take

01:06:36.800 | what is intended to be a really good piece of advice and use it against themselves. And I will

01:06:40.320 | say this on the points redeeming side is that so many of us who love points who love teaching about it,

01:06:45.440 | we, of course, want to teach you methods where you can get more than one or one and a half cents per

01:06:49.680 | point of value from your points, we want to share with you, what are the ways that you can get just

01:06:54.080 | extraordinary value. But I think one of the things that sometimes can get lost in that conversation is that

01:06:59.920 | what people hear is because it's possible to potentially get some crazy amount of value from

01:07:04.400 | your points. Anytime they decide to not do that, again, they're doing it wrong, or they're making a

01:07:09.120 | bad decision around points. And one of the things I really like to tell people is, no, no, no, learn all

01:07:14.720 | the potential options out there for you. Is it really, really fun to book a first class flight on JAL

01:07:20.880 | through American Airlines for 80,000 points and fly first class from the States to Tokyo and quote,

01:07:26.240 | unquote, save, you know, $20,000? Yes, that's amazing. If you want to do that, I will applaud you the whole

01:07:31.600 | way. I've done that. And it was incredible. And also, I've made quote, unquote, bad redemption where I'm

01:07:37.200 | trying to fly somewhere specifically with my family, or I'm not that flexible. And I've booked a redemption

01:07:44.080 | that got quote, just, you know, whatever 1.7 2.1 cents per point. I don't beat myself up about that

01:07:51.000 | whatsoever. So in terms of points redeeming, I really want to encourage you all continue to learn

01:07:56.160 | continue to understand what is possible strive for that if that's what you want. And also,

01:08:00.800 | if you love the way that you are using your points, I really don't think that there is a horrible or a

01:08:06.800 | bad use of points. So please don't think that it has to look one way in order for you to be doing this

01:08:13.140 | hobby the right way. Because I just don't believe in that. Yeah, on the high, high earning high spending

01:08:17.980 | side, something I've noticed recently is there have been some really competitive business class

01:08:23.200 | fares. And historically, I would always tell people, hey, you know, you can get better than

01:08:28.340 | the portal if you transfer your points to airlines. And depending on the portal, right on Chase, if you

01:08:33.780 | have a Chase reserve, you can get one and a half cents. If you have an Amex business platinum, you can

01:08:38.440 | actually get a 35% rebate. And I mean, if you had a Amex Centurion, you'd get even higher rebate. But I

01:08:44.420 | don't think we have a ton of black cards in the audience. And that ends up being 1.54 cents.

01:08:50.260 | There are some business class flights where I've seen round trip from the West Coast to Europe for

01:08:56.600 | $3,000. And if you're getting one and a half cents per point on a $3,000 fare, that's 200,000 points.

01:09:04.520 | And that's the equivalent of 100,000 points each way, which sure, have I gotten 50,000 points on Air France?

01:09:12.400 | Absolutely. But when you're looking for a family of four, 100,000 points for a flight to Europe is not that

01:09:18.760 | unreasonable. Add on the fact that there's no extra taxes and fees, which oftentimes you're looking at, well,

01:09:25.180 | it's 70,000 points, but plus $250. Add on the fact that those flights you're booking in the portal are earning

01:09:31.800 | points. And depending on the airline and the way they calculate earning, a $3,000 flight could earn

01:09:38.220 | you 20,000 points. There are a lot of cases where that's true based on the earning rate or the distance

01:09:43.400 | flown. And so if you say, wow, I'm going to spend 100,000 points each way to get a flight that's going

01:09:50.680 | to earn me 20,000 points and have no taxes and fees, it might not actually be a bad redemption.

01:09:56.620 | And somehow in my mind, spending 100,000 points on a flight seems more reasonable, but I've trained my

01:10:03.900 | brain to say, but using the portal, I can do better. But at this point, it's about taking the trip we want

01:10:09.960 | to take. It's about having the experience we want. And I'm increasingly being more comfortable

01:10:15.360 | burning points at really like portal level redemption. If it lets us take the trip we want

01:10:21.340 | in the class we want, you know, to the place we want, I really like it. And so I'm just going to

01:10:26.240 | challenge everyone to also think that way themselves and be more flexible with what they're doing.

01:10:31.680 | And the only little tip I'll give that adds on to what you said about asking people who maybe say

01:10:36.920 | they don't take cards to do it. One of the most lucrative things I've found here is setting up a

01:10:42.480 | business profile on Venmo is very easy. And obviously things change. But at present, when you

01:10:49.240 | pay someone on Venmo from a consumer account to a business account, and you use a credit card,

01:10:54.960 | the current fee as someone who's received is 1.9%, which is a really reasonable fee. So if you need

01:11:02.520 | to make a payment to a tutor, a nanny, like if they can set up a business Venmo account, and you can make

01:11:08.700 | that payment and offer to cover the cost of the fee, there can be a really great opportunity at much

01:11:14.720 | lower than the typical 3% fee. So that's the one I'll add there. But I really wanted to close on the

01:11:20.460 | note of, you know, don't beat yourself up, try to find the thing that works for you be happy with that. And if

01:11:26.760 | you're getting any value out of this, it's awesome. We could keep going. You know, we recorded back to back.

01:11:32.260 | So we've been going for almost three hours at this point. For anyone who wants more, where can they find

01:11:37.360 | all the stuff you're working on?

01:11:38.500 | My name of my business is point me to first class. It's a little bit of a misnomer. I will happily,

01:11:42.920 | happily teach you all how to fly in first class. But my belief is that points and miles can make

01:11:47.380 | any travel experience come true. And what's first class for me doesn't have to be literal doesn't

01:11:51.960 | have to be literal for you either. But at any rate, you can find me on my website is just point

01:11:55.680 | me to first class.com. And I also have a podcast by the same name point me to first class. And this

01:12:00.100 | is where I talk about all things points, miles, credit cards, especially for folks who do tend to

01:12:05.140 | have high business, high personal spend, what the game looks like sort of a different level and how you

01:12:10.480 | can continue to really leverage your expenses, turn them into unforgettable travel experiences. So those

01:12:15.880 | are the easiest places to find me. Awesome. Thank you so much for joining me today.

01:12:19.480 | Thank you for having me. It's been an absolute pleasure. I appreciate it so much.

The Path to Becoming an Expert in Points & Miles with Devon Gimbel

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