Frequent Miler on the Air - Should I use points for business trips? | Question of the Week Ep19 | 10-19-26

Episode Date: October 19, 2026

This podcast episode is sponsored by Saily. Saily is an ESIM service app created by the security experts behind NordVPN. Instead of paying absurd daily rates to your home carrier or swapping SIM cards on arrival, Saily gives you flexible prepaid data plans in over 200 destinations worldwide. Download Saily from your app store and use our code FREQUENTMILER at checkout to get 15% off your first purchase. https://saily.com/frequentmilerShould I use points for business trips? Brian wrote in with this question, asking:How do I handle bookings when my small business pays for the flight? I have never used points/miles to book a business trip because it feels like I’m using up my personal miles for what would be a legitimate business expense (even though I earned many of those point/miles from business travel). Every once in a while, I see a very good redemption opportunity but don’t take it because I don’t know how to value those miles as a business expense - if it’s a cash booking it’s very straightforward. But this seems like I may be unnecessarily hurting the business by paying more in cash. How do you think of points/miles in this situation? This could apply to hotel points and FNAs as well.(01:58) - One option is to assert a value for your pointsFind our RRVs here(05:16) - Business pays base rate & you use personal points to upgrade or copaySubscribe and FollowVisit https://frequentmiler.com/subscribe/ to get updated on in-depth points and miles content like this, and don’t forget to like and follow us on social media.Music Credit – “Ocean Deep” by Annie YoderCheck out all of our other travel podcasts from around the worldThis podcast is part of the Voyascape Network, a collection of some of the world’s best travel podcasts. Explore more at Voyascape.com. For advertising or sponsorship opportunities on this show and across the network, email [e-mail] or you can find more information at Voyascape.com/advertsing.

This is a Voyescape podcast. You can find all of our travel podcasts from around the world at voyescape.com. This week's question of the week, should I use points for business trips? Brian writes, how do I handle bookings when my small business pays for the flight? I've never used points or miles to book a business trip because it feels like I'm using up my personal miles for what would be a legitimate business expense, even though I earn many of those points or miles from business travel. Every once in a while I see a very good redemption opportunity, but don't take it, because I don't know how to value those miles as a business expense. If it's a cash booking, it's very straightforward. But this seems like I may be unnecessarily hurting the business by paying more in cash.

How do you think of points and miles in this situation? This could apply to hotel points and free night certificates as well. So I thought this was a fantastic question, and it was a very good question for Greg the Frequent Myler because you obviously have this to contend with, you know, from time to time throughout the course of the year. And so I was curious what your approach is. Yeah, it's a great question. And it's forced me to think more deeply about it than I have before because it's come up repeatedly, of course, over the years where, you know, I need to get somewhere for the Frequent Myler business. And there's a great award price. So do I pay for the flight in cash so that it makes it easy to deduct it as a business expense?

Or do I use points and just forget about it being a business expense? Or do I figure out some way to treat it as a business expense even though I use points? And I've done probably all of those things at different times. So I'm not going to say what is the... right way to go, but I'm going to describe some options that have I've either done or have occurred to me over time. One is to assert a value for your point. So let's say you have a business trip. And of course, we're talking about like where this is your own business. We might want to touch on a little bit when it's someone else's business and you're traveling for them. But so,

so you have a, you have a business flight or hotel, whatever, both. And there's a good points deal where you'd be getting really good value from your points. So what do you do? One way is to just sort of mentally or accounting-wise have your business buy the points from your personal side, basically. So treat it as like the business expense is your business buying the 60,000 points. needed for that flight, basically, from you. So it's an accounting trick, right? And so how do you value those points?

I mean, one way it would be to use the frequent Miler, reasonable redemption values, and that way, if there's any kind of audit or whatever you can point to, you know, this is the page that has the information, this is the value we used. So that's one way to do it. I have not done that,

even though it makes a lot of sense, I think, to do that. do that. Another way, and I have done this, is sometimes there's been really good deals for buying points, like points are on sale, there are aeroplane points on sale for a great deal or avios, whatever. Sometimes I said, all right, I'm going to buy this, I'm going to have the business buy this, because I've used more than that many points from my personal stash for business travel. So it's kind of a way. for the business to make up for the points that I'm using from my personal stash for my business travel. So it's not an exact. I don't try to match it up exactly, but I know that I've spent

more points from my personal point stash for business travel than I've bought for the business. So I don't feel like I'm, you know, abusing that or anything. I don't go out of my way to make sure it's the same kind of points, right? So like I just kind of say, well, there's a great deal on aeroplane points. I will probably use aerial plane points at some point for business travel, but if I'm using some other points for the business travel, I see that as sort of a, it just offsets. And I should back up and say, I'm not an accountant. I have no idea how accounts would treat this. But from my point of view, an accountant would just see, I bought points for business travel and I'm going to use them for business travel.

End of story, really, is how I think about it. Yeah, I mean, to make it clean, you could just buy the points that you need for that trip. If it's cheaper to buy the points than it is to buy the ticket or in the hotel or whatever, then you can just buy the points and save business money that way. You could do that. I just personally have a hard time like buying points when they're not on sale, right? Like, it just seems like a bad deal.

So that's why I do it the more sort of convoluted way that I described. Another option, of course, is to, I shouldn't say, of course, but another option is to use your business, is to have your business pay the base rate for a hotel or flight and use points to upgrade. So in that case, what you're doing is you're having the business cover, sort of the base amount, and then you're using your own points to make that experience better, right? there are I think there are more opportunities to do this in the hotel world than there are in the airline world at least for good value so let me just talk about a few examples one is Hilton so if you have a good if you find a good Hilton value for using your points you know, it's a $600 stay and it only costs 60,000 Hilton points. That's one cent per point value.

That's great for Hilton. Then you might say, well, I wasn't going to spend more than $400 a night for my business. So what you could do is you could actually, or whatever that amount is, let's say $300. You could actually, Hilton lets you, when you're checking out, drag a slider. say how much of this do I want with points and how much with cash? So you could make 300 of it be on your credit card, and that's your business expense. And the rest is your own personal points. And so you're getting like a nicer hotel than you would have gotten if you had just spent $300, right?

Do that make sense? Yeah. I think so. Yeah. So you're using the business credit card to pay the amount that you have allotted or budgeted for lodging from the business and using your points, your own personal points to make up the difference to stay at a nice place. Yeah.

And another way of thinking about, like, let's say you're looking to stay in London or something. And it's like, okay, if my business is paying for this entirely, I'm going to stay at that Hampton Inn. But because I could do this points and cash thing with Hilton,

and there's a really good value at the Conrad, I'm going to stay there instead, right? So you're upgrading your stay, but you're not costing your business more, but you're still getting to deduct that base amount from your business spend. This is one I should mention that can also be done if you're on a business expense. It's not your business, but you're allowed to use your own credit card to pay, and you have like a cap. You know, you're allowed to go to, you're allowed to spend up to $300 a night on hotels or whatever.

You could do this Hilton trick to stay at a nicer place, basically, because you're kicking in your own points. Hyatt, it works a little differently with Hyatt, where what you could do there is, Hyatt's points in cash isn't necessarily a great deal. It can be okay, so you could look at that. But what can be really good value if you want to use your own points to upgrade your stay is use book a cash rate, and that's what you charge to your business for a base room. And then Hyatt lets you pay 6,000 points per night upgrade to a standard suite or 9,000 points per night to upgrade to a premium suite when they're available. So that can be a really good value way of kicking in your own points and still expensing the bulk of it to your business. As far as flights go, I did mention before that it's rare that you can get really good value upgrading with your points.

But there are some, like I know that I've heard people talk about or I've read people write about both British Airways and Virgin Atlantic having options where when the next level cabin is available as an award flight, it's probably available as an upgrade as well, and you might be able to pay an upgrade, you know, amount of points to upgrade from that base cash fare that you paid. I think there are limitations that, like, I don't think that'll work for the cheapest economy fair you can buy, for example. So you have to be at a higher level to start with in order to make that work. Yeah, and I'm going to add to all of that good advice that it also somewhat depends probably on your business and what your goals are for that business. Because I think that going back to the point in the original question, if you feel like you're costing your business more by not using points and paying cash just so you can expense it, you know, keep in mind that expensing something just to reduce your business income, if it's, you know, reducing your income, then whatever tax savings is, you know, there might be, might not be worth it, you know.

So if you got a business where, where that's going to make the difference in the long run over the course of the year, you may prefer to use your points and increase the profits of the business. Of course, if that's, you know, where the margins are, then also maybe the business needs something additional in terms of need to produce some more revenue to make it worth making those trips and doing those things. And I'd say for the first five or six years of this business, you know, I didn't even think about paying from business expenses because it's like, of course, I'm going to just do whatever

is the cheapest and that's usually with points. Right. Right. Exactly. So I think it depends on the success level of your business. But I think when we were talking about buying points, something that comes to my mind is, you know, if you've got a relatively successful business that can afford to fronts of money, when points are on sale, you could just buy points and use those stashes as the ones, you know, Greg obviously mentioned how you might do it by kind of replenishing some points and using other points. But you could also just buy dedicated, these are my business points stashes when they're on sale. If you can afford to float that for your business in order to save your business money on travel in the long run, when life miles go on sale or airplane points or Hilton points or whatever,

you could just do that. And I think that's another pretty valid strategy being the easy thing to expense that. This episode was produced and edited by Carrie Yoder, music by Annie Yoder. If you've enjoyed what you've heard today and you'd like to get more of this in your email inbox each day or each week, go to Frequentmyler.com slash subscribe to join our email list. Follow us on all the various social media. Join our Frequent Myler Insiders Facebook group. And wherever you're watching or listening, don't forget to like this or give it a thumbs up. If you have a question that you'd like to be considered for a future question of the week or a piece of feedback that you'd like to be considered for our giant mailbag. You can send that to mailbag at Frequentmiler.com.

Thank you.