(upbeat music) - Hello, and welcome to another episode of All The Hacks, a show about upgrading your life, money, and travel, all while spending less and saving more. I'm Chris Hutchins, and I'm excited to have you on my journey to optimize and upgrade my own life. Now, a good portion of the emails I get from you all are about how to best use all the points and miles you've racked up for travel.

And while I've covered parts of that in at least a dozen episodes, I felt like it's time to have an episode solely focused on booking or travel. So for the last few months, I've been trying to track down someone who is truly world-class at this, and I did. So today, I'm joined by Tiffany Funk, who knows this game in and out.

For the past decade, she's produced, written for, and been the managing editor of One Mile at a Time, the largest independently-owned travel and loyalty blog, and she also ran operations at one of the top award-booking services, Points Pros, for nine years. Then, she took all that experience to co-found Point Me, one of, if not the best award-searching product out there.

So today, we're gonna break down the why, when, and how to search for award travel, talk about some of the philosophy about how to think about travel with your points and with your miles. We're gonna get tactical, so you can confidently put your points and miles to good use.

I'm also gonna try to get a few travel hacks and tips from Tiffany, because after visiting 80-plus countries, I'm sure she has plenty. So let's get started after this. Tiffany, welcome to the show. Thank you for being here. - Of course, thank you. - Before we actually talk about the process of booking award travel, I just wanna talk about why people should even think about award flights.

I know I get a lot of people that always email me in and say, "Wouldn't it just be easier "if I just redeem all these points for cashback "or book in the travel portal?" And I know you've thought about this more than anyone. How do you think about that trade-off?

- Yeah, that's actually really interesting, because my answer three years ago would've been different, and I actually think as we talk today, there's going to be a lot of things where I will say, "My answer three years ago would've been different, "but for right now, this." In general, everyone has points, though, and no one knows how to use them.

And I think there's an intimidation factor, and people just think, "Okay, it's hard, "but the portal is easy." So I think it's worth knowing what the options are and how to explore your alternatives, and just do that comparative shopping, even if you do ultimately end up booking through the portal because the nonstop flight isn't available using a traditional miles and points award, or you decide that actually for this trip, the economy is fine, and so the value is better through the portal just because of the way the economics have changed in the past couple of years.

But ultimately, there is tremendous value to be had by leveraging these loyalty programs and their partners and what we refer to as distressed inventory. The goal of an airline executive who works in loyalty management would be to take all 150 of those seats on a 737 and sell every single seat on the plane for the maximum amount that each passenger was willing to pay.

So that might be a $49 WebSaver special, it might be a 65,000 mile redemption, but at the end of the day, if the seat goes out empty, no one gets anything. So because of that, there's this very complicated interaction between the airline, their alliance partners, other partners, where everyone is collaborating in the background to make these seats available in different inventory buckets, and that's where the magic of miles and points comes in because there's frequently opportunities to use points that you didn't even know you had or had access to, but they're one of 25 partners that your credit card or your hotel points can transfer to.

You can move them to that program, you can get a seat on the same flight you were going to purchase otherwise, and you're spending a fraction of the points that you would have. - Is there a kind of rule of thumb fraction where using points by transferring them to partners can be two to three times as valuable?

One of the scariest things is if you Google online, you'll find someone who writes a post about, I got 25 cents per point booking this crazy thing. I don't wanna set the bar there, but is there a place where you're like, look, even this feels like a win? - Yeah, for sure.

On average, over the time we've been doing this, I typically find that people who are transferring their points to a program and redeeming through the loyalty program charts and those methods, they're getting six to 12 times the value of someone who redeemed through their credit card portal. And I like to make that comparison because when people talk about the value they got for flights, it's frequently not reality-based.

- And what do you mean by that? - Because ultimately, and this gets into the economics classes that maybe it's been a while since anyone's taken, the ultimate value of a thing is only what you or a comparative consumer is willing to pay for it. So that flight from Los Angeles to Abu Dhabi is only worth $25,000 if you were ready, willing, prepared, and able to purchase a $25,000 flight to Abu Dhabi and I don't have anyone in my life for whom that's true.

So you can't really say, okay, I traded in my 70,000 advantage miles for this $25,000 flight because those 70,000 points are not worth $25,000. You would not have paid $25,000, right? What you would have paid might have been $4,000. You know, if it was a special occasion or something, even still, I don't know a lot of people who are buying $4,000 flights to Abu Dhabi.

So I like to base it off of what you would have paid booking through the credit card portal because you would probably, if you were in the credit card portal, seen that price for that flight to Abu Dhabi and been like, I'm not spending that many hundreds of thousands of points, but 70,000 points is a bargain.

- Yes. - And sort of looking at it that way and framing it a little bit more practically. - And are there types of travelers for whom that huge multiple is not as valuable, whether it's people flying economy versus splurging for business, only flying domestic, international? - So it used to be that the best value for your points was very consistently international premium cabins, where you were going to get tremendous outsized value if you were booking, especially a partner, and booking the front of the plane versus if you were trying to use your points domestically.

There's so many occasions where I'd see somebody be like, oh, I booked tickets from Phoenix to Orlando and they were 50,000 per person each way, but it was first class. I'm like, oh my gosh, you're paying first class on a terrible, terrible product. There's nothing first about a Dallas to Orlando experience regardless.

And 50,000 points per person, that would have been enough for you to go to Europe. But I've tempered that a bit as I've matured in the space. Some people just really want to go to Orlando and so that's the best value of their points. There's no value for them in Paris.

It is what it is. And I don't wanna be disparaging of other people's travel plans and dreams and things like that. The other thing is that the combination of dynamic pricing and the huge change in airline routing and capacity that we've seen since COVID began, means that domestic awards can actually be a phenomenal value.

Your flights are very full, they're very limited. And again, everyone is playing the same game of not having seats go out empty. So there are frequently times where I've seen domestic flights where if you go to buy them last minute, they're setting them at 450, $600 for an economy flight, but you can get them for 7,500 miles.

That's a great use of your points, no matter how you slice it. - And is that domestic economy or business? If domestic economy can be a good deal and international business could be a good deal, it seems like there's probably something good along the whole spectrum. Is there any gap where you're like, "Whoa, if you're interested in this, not a good fit." - Yeah, so I generally would say that domestic first or business is still not a good deal, for the most part when using points.

And that has gotten worse since COVID because we don't have a lot of people traveling for business anymore. So the cadence of inventory is different. There's a lot of leisure travelers though, and there's a lot of people who haven't traveled for a few years, and so they're willing to just buy up and pay the extra $100 when they're booking their ticket to have domestic first.

And that sort of becomes the thing, is the buy-up price might not be very high. It might be 100 or $150, but the award price is probably at least double of economy. And maybe that's fine if you're going from 7,500 miles to 15,000 miles, but if you're going from 25,000 miles to 50,000 miles, that's just a huge premium for a recliner.

- First off, like you said, it's a recliner. There are very few other than San Francisco, LA to New York, very few of the routes domestically have a quality business class product. Internationally, you said maybe it's 100, 200, $300 buy-up. I kind of always had this mantra of like, I'm never gonna pay for business class.

That'd be crazy. I've had times where I've looked and it's like $100 more. And it's like, wow, we have kids, we're traveling with bags. The bag fee's $30. - Exactly, just adding that up by itself. It's like, okay, this actually makes sense. - But internationally, whenever I look, it still seems to be like three to five times more expensive to buy a business class ticket than it does a coach ticket.

So that's where I think you can get another bulk of value. Does anything change now pre-pandemic? It was me and my wife, just the two of us. Now it's me and my wife, two kids and an au pair. - So everything has changed. - Everything has changed in more ways than one.

But when it comes to travel, if you're playing a game trying to look for five seats, I wanna get in, by the way, to the actual meat of this conversation, which is how do you do this? But someone emailed me the other day and said, well, we have four kids.

We're looking for flights with six of us. Like what kind of expectations should someone like that have because I think looking for one seat is so much easier than looking for four, at least in my experience. And if it's more than-- - So many things are different when you're single than when you have a family.

And this is actually one of the things that has long bothered me about the miles and points space, and especially a lot of the influencers are pretty consistently younger people with not a lot of ties. And they come from a pretty high socioeconomic status. We're guilty of this. Ben and I, at one mile at a time, so much of when we were doing our things, we had partners, but we had a lot of flexibility.

We were both digital nomads. So it's very easy to be like, yeah, Buenos Aires for the weekend, why not? Once you have other responsibilities and other people in your life, things change, right? So I'm very sensitive to people who have kids. I will say in your case, it's much easier when they're the size that they are and you don't have school schedules to contend with.

Once you get into school schedules, I think the expectation needs to be adjusted on the earning side of the equation. For your listener who has the family of six now, and if they know that they're going to be traveling over comparatively peak dates, you're either going to be going over spring break and everyone in your area has spring break at the same time, or you're going to be going like when school gets out or things like that, like that's just the natural cadence of family travel.

You need to solve that ahead of time and earn more points either in a specific program or that can be transferred to a specific program from a variety of sources. And we can talk about some of those because ultimately for a price, these airlines are willing to accommodate any lack of flexibility that you have.

You just need to prepare for that early and just know that like your awards might cost you more in terms of points, you could quantify, okay, what is the cost of a connection? What is the cost of mid-con red eye with toddlers, right? There's huge costs that aren't the points cost for doing that.

But if you can stack up a bunch of points in flexible programs, Capital One and Chase and even Built Now, and then transfer those points to Flying Blue, like Flying Blue will absolutely have six seats for you from California to Europe during peak dates. You're going to pay some fuel surcharges, but you can know that and you can plan for it and you can budget around it and you can still get a tremendous redemption.

It's just different than what a tremendous redemption might've looked like when you were unencumbered. - We're looking at a trip in February to Belize, which it's so crazy because it's not that far. It's like just a tiny bit further than Cancun, but getting there is like 10 times more complicated because there's no direct flights.

So we were like, man, it's going to cost us like 70, 80, 90,000 miles to get there, which in our mind seems crazy for such a short trip. But the week that my daughter doesn't have preschool is the week that all the schools are out in February. - Exactly.

- And the flights are like $1,500, $2,000. If you don't want to fly to Dallas and sit at the airport for seven hours and then get in at 11 p.m. and leave at 5 a.m., it's actually still a good value to use the points. It's just a lot more points than it would have been if I was like, oh sure, I'll take the red eye on Wednesday and I'll hang out at an airport for five hours.

It's just a different calculus. So my takeaway has been the value is still there. It's just more points. And now that it's more points because of the flexibility, the desire to not change planes as much or long layover, you just need more points. - Right, but I will also say that there is a benefit in thinking outside of the box with family travel.

Any trip that you would take within North America, including upper or Central America and things like that, Belize is a perfect example, is going to be expensive because a lot of people think that it's close and it's easy. If you were to look instead those same dates and look at going to Thailand, I would wager that your travel time is not much longer.

You would spend far fewer points. You're still getting to beach. You're getting vastly better food than anything Belize has to offer. And you might be surprised, right? It might be something to think about. And I know a lot of parents, especially newer parents are hesitant. They're like, "Oh my gosh, it's a long flight." Okay, but is it?

It's probably the same travel day. I did this. I'll actually send you some pictures, Chris, 'cause they're adorable. We took my sister's family and her kids. We went to Thailand for a couple of weeks over Christmas and all in, everything done, we spent about $2,000 per person for 10 days, including the value of the points.

And granted, I had the points to spend and not everybody has points to do seven people in international first class. Again, you can plan for that. And it was great. My nephew was seven at the time, which is a very precarious age for travel because they can't sit still, right?

And they're very busy, but he was great. And he loved the flight. He laid down in the bed. It was fantastic. We worked through the jet lag and we didn't have to spend 12 hours in DFW, which we would have had to do and did the next year when they went to Costa Rica.

- In this case, the family has decided this is the family trip. So there's a little bit less flexibility. - Yeah, so you didn't get a vote. That's the other thing about being a parent, right? Is your vote share diminishes tremendously as you. - But we're gonna start planning more family trips for our extended family.

This is an extended family trip where we're like, hey, this is the plan this year. This is where we're going. Let us know if you need help booking it. But I think we can agree. Getting your points and transferring them can be a lot of value. There's almost 30 different airlines.

You can transfer to amongst all these flexible points programs. I went this morning, I was like, okay, if you sum up Amex and Built and Chase and Capital One and Citi, there's 30 airlines. And if you look and include their partners, it's almost double that. Where does someone start to think about this?

And I know you guys have a product to do this. So I wanna cover both with and without tools. But if someone's like, all right, I've saved up the few hundred thousand points I need to take a family on a trip anywhere in the world. But like, what do I do?

The Amex probably has like more than a dozen places you could transfer those points to. How do you think about that if you're someone new to this? Okay, so the very old school way. So I would actually take it back a step and I would think about this before deciding whether I'm going to get an Amex card or a Chase card or whatever other card.

Because while they do have a lot of partners and there's a lot of leverage, there are some unique situations where you can't get Amex points to United and you can't get Chase points to American Airlines. And because of how airline inventory management has evolved in the past few years, there may be times where you do need points with that domestic carrier because they are making space available only to members of their program.

So if you were talking before we started recording, you mentioned French Polynesia. So if you know that you wanna go from San Francisco to Papeete and the only carrier that has a points program that flies in nonstop is United, that's a trip where I would probably look at paying cash for the flights because they can actually be pretty reasonable in comparison and because they are considered South Pacific, the award prices are bonkers.

But if you know you're going to want to use miles, you know you're going to need United miles in that case because they're not gonna make space available to their partners very, very rarely. So you probably, in that case, wanna get the Chase card versus the Amex card. So that's my setting the table for that.

Otherwise, what I like to do, if we're doing the old school way, I like to go to Wikipedia and look at the destination that you're going to and literally put in CDG for Charles de Gaulle Airport Wiki and go through and look and see like, who are the airlines that fly there and where do those airlines fly to?

This is the most manual way possible that you can do it, but I think it's really helpful 'cause you can look at it and you can be like, oh, okay, I didn't know that Air France flew there from Salt Lake City or whatever. I actually don't have the Wikipedia page open for the Paris Airport, so I hope that's still true.

But you can look at that and if you cross-reference that to then the list of partners for your credit card, you can see like, okay, does Air France fly in blue? Oh, they are a partner of my program. Okay, so that's a good place to start. That's sort of the baseline.

You could go from there. When you get into the more advanced ways, it's like, okay, well, what other programs are partners of Air France and is there an arbitrage opportunity by moving my points to some other SkyTeam carrier or some non-Alliance carrier and looking at their award charts? And at this point in time, you should have 30 to 70 browser tabs open and that's how you know you're doing it right.

- I wanna go back to this example of maybe it's better to have points in the domestic program. So I will say, I got lucky. We were flying last minute and it was actually cheaper to book through Air Canada's aero plan for the flights to Papiete. - Right, but you were booking last minute, which is not how most people plan their trips to Tahiti.

- Totally. - That's sort of that give and take, right? If you were like, oh, maybe we can go to Tahiti or maybe we'll go to somewhere else. - Yeah. - Then that's fine, but. - Are there programs in general where you're like, okay, Flying Blue, I think is a great example because they're a partner of most flexible point programs.

They have pretty reasonable award prices. Is there a, okay, I wanna go on a common route. I wanna go from New York to London. There's probably a quick version of, I would say like maybe it's check Air France, check United or Air Canada and check British Airways. And like start there, maybe you find something great before you get to the 60 browser tabs.

- Well, you said if somebody was brand new and wanted to know, right? So like they don't necessarily know where to look. So if you're going New York to London, I would look first at Virgin Atlantic. And I would also look at the travel time for New York to London.

I've been on a New York London flight that ended up clocking in at three hours and 45 minutes. I don't need business class for three hours and 45 minutes. That's something to consider too. And Virgin Atlantic will frequently have nylon for like 10,000 points in economy. And that's an incredible bargain.

It can be a four hour flight. We think of like, oh, it's international. But when you're already in New York, it's not that far. But again, I think if you were looking at the Heathrow Airport Wikipedia page, you would have been like, oh, Virgin Atlantic and they're a partner of all of my credit cards.

I can look there. So it's the same method. You don't have to memorize these things. - I just didn't know if you had like a, before you get to 60, here's three or four to start with to see if you find something good. - I think it depends where you're going.

People always want me to say like, well, this is the best program. And this is the best partner, so we should go. But it really depends. And as we see this trend where loyalty programs are making more and more inventory available exclusively to members of their own program, it's better to keep your points flexible than necessarily go all in on that one program.

Because what if you can't book something with their partners that you would have expected to be able to book? Like back in the day where we moved maybe a billion points from membership rewards to AeroPlan to book Lufthansa First Class when it was a 16 seat cabin with no fuel surcharges through AeroPlan.

And like, it didn't even matter. Frequently I would tell people, no problem, there's space. And then I would go and actually look to see if there was space. Because there was always space. There were 16 seats in the First Class cabin. Of course there was space. - And to be clear, these were client points.

You didn't actually have a billion points yourself. - Correct, these are other people's key points. Yeah, and so things evolve and they change. One of the great evolutions in the miles and points space in the recent comparative years from when I've been in the game has been the advent of these flexible points.

So you don't have to commit to a single program early on. - It's funny, I always use the United card as the example. People are like, oh, I live in the Bay Area so I have this United card. And I'm like, well, even just a chase card might actually earn you more United points than the United card itself.

And then those points actually could go to a bunch of other airlines and you don't have to decide until you're planning the trip. - Exactly, if you live in the Bay Area, you should have the United card and you should not spend on it unless you are purchasing tickets on United.

You need the baggage benefit because you're flying economy. In that case, it makes sense because getting triple points from another card doesn't offset the $150 that you would pay in baggage fees. But yeah, don't use it at the grocery store, please. - Or maybe even for buying United flights.

- Does United still have that limitation where you only get the baggage benefit on your credit card if you purchased the flight using a United credit card? - That is a question I don't know the answer to. - Yeah, I don't know it off the top of my head anymore, but it used to be the case.

And so that was then my exception of like, this is the time when you would use that United card. Otherwise, for the Delta and American cards, have them if you check bags, but don't use them. - It's funny, I used to be in the like, why would you ever check bags camp?

And it's like, oh, because maybe you have children. - Now you have kids, yeah, yeah. - Hi again, it's Chris's wife, Amy. Do I need to keep saying that? Anyway, Thanksgiving is always a time where I reflect on the things I'm grateful for and think about ways I can give to others, which is why I'm so excited to partner with Daffy for this episode.

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And for a limited time, if you visit that link, you can get a free $25 to give to the charity of your choice. Again, that's allthehacks.com/D-A-F-F-Y. - So I am quite comfortable right now, which is actually true almost every day, and that's thanks to Viore, and I'm excited to be partnering with them for this episode.

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So, you should definitely check them out at allthehacks.com/viore, or in the link in the show notes. Again, go to allthehacks.com/v-u-o-r-i, and get yourself some of the most comfortable and versatile clothing on the planet. - You mentioned the flexibility was probably the reason I found such a good deal. If someone's thinking right now, "Oh, I wanna take a trip," do they wanna start looking right at one year out?

Is there a sweet spot that you've seen of when someone should start actually looking for a trip they're planning, if they know long enough in advance that they could search any time? - If you know that you're traveling someplace a year from now, look and book right now. You can always cancel it.

You can always change it. Award tickets are super flexible. There's frequently not even a penalty. It depends on the program, of course. But it's so easy to change or cancel them, and you're not going to necessarily find something better. It used to be that within 10 days of departure, we'd see a lot more award space.

Again, the goal is for seats to not go out empty. But with COVID and the social commitment to not having non-vaccine precautions, the reality of that is flight attendants and pilots are getting sick, and they're not at work. And so if you are managing operations for an airline, you used to comfortably be able to say, "Okay, 10 days out, this is probably "what our flight loads are going to look like.

"These are the seats that are going to have occupants." And then we feel good about it. And inventory management could say, "Great, we're gonna release these seats into inventory. "We'll let partners book them. "Maybe we'll have a last-minute sale." There was some degrees of confidence. Now, we're seeing that inventory get held until sometimes two hours before departure, because on any given day, if you have one flight get canceled between San Francisco and Minneapolis, you now have 150 passengers that you have to do something with.

So if you don't have a crew, you have to accommodate those passengers. And so we're just not seeing the near-term inventory dumps that we used to see. That could get better. So if you're booking a year out, you might get lucky. And within 10 days or three days, you might see a better itinerary.

You might see a nonstop. You might see a nicer product. And you can change to that. But in the current environment, if you see something, I would book it. - Okay. What about flexibility with where you go? This is a question that I know you've gotten and I've gotten a lot.

It's like, "I just wanna take a trip "that lets me get a great use of my miles "and go somewhere in Asia next year." And I know from using basically any search tool on the internet, Google Flights is probably the closest, but it certainly doesn't have any miles and points component.

But just to be like, "Okay, from San Francisco in July "or next year, where could I go that's cheap?" Is there a points and miles equivalent? Or what do you tell people that have a little bit more flexibility but don't wanna run 1,000 searches? - In general, I think that the best use of points is always going to be something that provides you with a great experience.

But when you're very flexible with destinations, I actually don't think starting with Google Flights is a bad option. Just to sort of see what the routings look like and the timings and to sort of get a sense of what the carriers are that are operating those routes. As long as you know that that doesn't match over to award availability or even award routing rules.

There are things that you can do with miles that you can't do with money and vice versa. - Can you give us some examples? - There's a lot of nuance to fair combinability. So if you're in California and you wanna go to Sydney, obviously there's the direct flights that are going to be expensive.

Qantas or American or Delta or United now has nice seats going to Australia. But you could also route via the Middle East. And you could do something like from California into Doha and fly Qatar's Q Suites and then go first class from Doha to Sydney. And you can't really book that with money because it's not a legal routing when using money.

Qatar might sell it to you as part of a round trip, but then there's different partners and things like that. But if you call Advantage and you say, okay, I need to book two awards, but I want them on one ticket, they can book that for you. And it's business class in Q Suites on the long haul.

So you get that nice flat bed. If you're traveling with a family, there's a suite that can basically be for four. It's a lovely experience. You can go to the museum and enjoy Doha and then go on to Sydney and it's like 100,000 miles. And that's a great value.

It's a really extended trip. It's a fun routing that you wouldn't necessarily do. And it's frequently fewer points than doing like an LA-Sydney direct. Because carriers charge a premium for that in both miles and money because they know that that's what people want to do. - So you can be flexible with routing and sometimes points and miles lets you do that.

What about just destinations? Like if someone said, I kind of want to go to Asia or I kind of want to go to Europe, I'm not sure where I want to go. Is there an argument to be made of just like searching the major hubs to try to find something there first to see where it might be easiest to get to or?

- Yeah, no, I think that's a perfect example. In general, it still makes sense to search hub to hub and just to get a concept of things. Let's talk about Europe because Asia is very complicated with COVID still. But we can go back to Asia. The thing that I think we don't think about because travel within the US is really unpleasant.

Travel within Europe isn't necessarily unpleasant and there are a lot of low cost carriers, there's a lot of trains, there's a lot of ways to get around. So if you really want to go to Amalfi, you don't need to look at tickets to Naples. You can look at tickets to Munich and then there's a bajillion ways per day to get from Munich to Naples that you can't use points for, but it might be like a $45 ticket.

So I think looking at a major hub in Europe as a starting point that you wouldn't mind spending a night in if you needed to or a day is a great place to get started with that. For people starting in the US, I think it's important to recognize that the closer you get to the ocean you're going to cross, the more flight options you will have.

So if you're in Miami and you're trying to go to Tokyo, good luck, you're not going to find seats. There is a Korean Air flight, or there used to be from Miami to Seoul, which would have been a good option, but realistically you're connecting in California or at least in Chicago or possibly in Texas.

And the same thing goes the other direction. If you're in California and you want to go to Europe, you could luck out and get a nonstop flight in business class at a good price point at the saver level. Or you might need to pay a few more points to have expanded availability.

And you could plan for that. Or you might need to make a connection. And that's where it gets into that sort of trade off of like, okay, if you're flexible and totally flexible, you still benefit from determining what is most important to you. Is it the in-flight experience? Is it the travel time?

Is it where you connect? Because overnighting in Frankfurt is not as fun as overnighting in Munich. Everybody has their own things of what matters to them. And the airports that they like to transit through and not. And I think if you consider all of that as part of your flexibility, it makes it a little bit easier to narrow down your travel plans and your flight options.

- And one thing we talked about before we got started was the flexibility of dates. People are like, oh, I want to go next year. One thing you pointed out that I was like, okay, well, are you really that flexible? I was kind of thinking about it for myself.

I was like, well, I might be flexible to go somewhere next year. Maybe I actually really only want to go on Saturday to Saturday or something so that we're not taking more than one week off of work or school or something. It's like, well, now you just narrowed 365 days down to like a hundred.

And you pointed out like, what about weather? - Right, there are places that are super muggy in the summer. And I love Japan as an example because everyone is like, oh, I'll go anytime. Like, but you don't actually want to be in Tokyo in July. It's very hot. They turn the escalators off.

You could still go and have a great experience, but like, it wouldn't be my preferred time. - What are the local holidays when you're going? If you're like, oh, okay, I'm going to try and time it for cherry blossom season, but do you want to be there during golden week?

Pros and cons to that. That should be a conscious decision. There's also a bit of just the human psychology of it where we all have this fear of missing out. And in decade plus of doing this, I think every single time, and I could check with my colleagues, but I'm pretty confident saying every time that we've had someone say, I'm totally flexible.

If I give you an itinerary, your natural instinct is going to be like, okay, but what about this instead? What about this alternative? So you aren't actually totally flexible. You do have opinions. You do have priorities and things that you want to consider. So when you're booking for yourself, I think just going through that triage list and thinking about what are school schedules?

What am I willing to accommodate? Do I want to have a night in a cool city on the way to my destination? Or do I want to just have a shorter layover and just plug through? Am I checking bags? If so, am I concerned about if my bags get lost?

One of my colleagues, their daughter and her husband were doing this hiking backpacking trip in rural Scotland last summer. And they did almost everything right in their planning, except they didn't plan enough time in Edinburgh at the start of the trip in case things go wrong. And so when inevitably with the Heathrow baggage meltdown of last summer, their bag was delayed.

They're like, we're in Edinburgh and we have nothing. We have just the essentials that we need in our carry-on, but we obviously didn't carry on our tent, right? So you need to think about that too. With the type of trip that you're taking, that may matter or it may not be an impact at all.

If you're planning on spending a week in Paris with your kids, having a lost checked bag is not a big deal. You're in Paris. You just go to Carrefour and buy whatever you need to buy and get it reimbursed through your credit cards, trip delay and coverage and move on with your life.

- The other thing I've just been thinking about is, okay, even if I was like Japan flexible next year, there's probably an ideal month or an ideal period of time. And I don't know if you have any stats on this, but I imagine if you're like, I wanna go to almost anywhere and you're flexible within a month, you're probably pretty likely to find something that I don't even know if you need a year's worth of flexibility to find a good deal.

- No, no one needs a year's worth of flexibility is my general sentiment there. Other than that year's worth of flexibility helps you rule times out. So like I personally have done it a couple of times and will probably in future avoid traveling to Asia during Lunar New Year.

It's a really fun experience in ways if you haven't done it, but I think for most people, if you're not actively setting out to do that, it's just frustrating, it's too crowded. All the places you wanna go, everyone else also wants to go and a lot of things are closed.

In Vietnam, they don't refill the ATMs during the holiday. So there's just like one very specific difficulty for traveling during that time period. So there's things like that that you can rule out. But in general, I would say there's always a word space and I don't wanna say that that means there's always good award space or there's always this thing that you saw on Instagram that you're going to be able to book, but there's always something and finding something that is good for you has a lot of nuance.

- Are there a few either routes or destinations that if someone's truly like, I just wanna go on an amazing trip with my points that you see more frequently than not popping up with better availability that could inspire someone and save them some points? - I would generally say, if you're going further, you're going to have better availability.

Like domestically, North America, even South America, flights are so full that there are just not the point bargains that people might want. And so I do think that if you're looking for some kind of like aspirational fun trip, it makes more sense to go further afield. You also have the benefit of when you're going further of getting those international products that are much nicer.

Qatar has their Qsuites product and availability is pretty good, not necessarily from all cities. Like it's not great from LA right now because it's very popular, but they also have it to Seattle. So if you're willing to do like that short hop up and then connect, then that opens up all of Africa and the Middle East and Southeast Asia to some really phenomenal options.

I think if you're doing that, I also like to look at places where hotels are reasonable. A lot of people have like the pinnacle of their trip as being like, I'm going to use my points. I'm going to fly business class or first class. I'm going to go to the Maldives.

And that's great. I personally don't love the Maldives, which I know is sacrilegious, but it's just a difference in what I'm looking for in travel at this point in my life. But I think that there's things like that that you can look at. Like we took my niece to Egypt when she graduated from high school as like her senior trip.

And that's not something that she would have picked or that she would have thought of, but it was very much like, okay, well, we're going to go during this time, what's available. Okay, there's easy space to Europe. And then we can connect down to Cairo and then to Luxor.

And I don't think she would even put Egypt on her radar as somewhere to go, right? And it's not like it's that exotic in the space of exotic travel, but it's very exotic if you're 17 from a smaller town. - How did you come to the conclusion that that was a place that was easy to get to?

Was that just trial and error or? - In general, Northern Africa is not difficult to get to. - Meaning availability. - And just their flight routings. And I think one of the reasons for that is it's well served by both European carriers and Middle Eastern carriers. And so you have that sort of combination of inventory and space.

Because you can fly to Abu Dhabi or to Dubai or to Doha and then connect up, or you can fly to Paris and connect down. So it's just, you have more flights there than you would think. It's also less competitive because it's not a place that as many people think to go to as like Florence.

I feel like the entire internet went to Italy this summer. I don't know about you, but I feel like every time I opened Instagram, it's like, okay, you're in Italy and you're in Italy and you're in Italy. So like a word space to Italy is very bad because people are just buying tickets to go to Italy.

Not as much travel to some of these other destinations. Also my bias is that I tend to like to go places that people don't think to go. That's just sort of where I'm at with travel at this point in time. Like once you get to the close to 100 country mark, I think you start looking for different things than you did in the first tranche of countries and destinations.

- You mentioned hotels, making sure that you don't get this amazing redemption to a place like the Maldives and then find out, okay, now I have to spend thousands of dollars a night. - Literally thousands of dollars. Yeah, even if you're using points, you still have to pay for that seaplane.

- But how do you feel about points used on airlines versus hotels? My advice has often been, if you have points in a hotel program, by all means it can be great. But if you have flexible points, other than Hyatt, on the luxury side, at least it can be tough.

I have heard a lot of people point out, no, no, no, there are some really good sweet spots in Wyndham and Choice Hotels and IHG. But I'm curious, you live and breathe this space. How do you feel about using your transferable points at hotels? - I struggle, I struggle.

I think I struggle for a different reason than maybe some other people struggle. 'Cause it's not that there aren't values, it's that my brain is full. And at some point in time it's like, okay, I recognize that there's this great value for choice points if I move it here and move it here and move it here, but I don't actually want to stay there.

That's a factor too. And the min-maxing of points to have a completely free trip is super fun. It's super rewarding. And also something that I don't think that most people have time for in their lives. So I generally have taken an approach where, okay, here's a great points redemption for hotels.

It's a fifth night free situation with a Hilton or a Marriott. Or it is one of these really niche properties where it's just ridiculous that you're able to use choice points to stay there, but it's this incredible castle, great. And if I found that and locked in availability there, then maybe I find myself being more flexible with my flights and not trying to have the ideal redemption for flights because I already have this great hotel redemption.

And I sort of ladder it personally. The flip side being, of course, okay, we found these incredible flights. I took my mom on a trip once. It was literally just an airplane ride trip. We did Emirates, A380s the whole way through. And it was like, okay, these are the dates that we're going to be in Dubai.

Or you know what, mom, let's go to Abu Dhabi and we'll stay at the Park Hyatt there in Abu Dhabi. That's fine. But then we're going to have a couple nights in Singapore and I'm not trying to get everything perfect. It's like, well, this is where I want to stay with my mom because I know that she'll enjoy this.

And I can use some points or I can just book it through the travel portal. And it's still a really good value, all things considered. And the experience outweighs the value in those cases a little bit. - There's only so many airlines that fly to a place and almost all of them, not all, but almost all of them have some type of program that you might be able to book directly or through a partner.

Whereas hotels, there are so many hotels that you can't book with points. And similarly to you, I find myself prioritizing the flights just so that I have the mental freedom to be like, where do we actually want to stay? - And that's, I think, sort of just a great way of saying it in that sort of mindset of, I got a phenomenal deal on the flights and I didn't spend $25,000 for my family of four on these flights and we're still having this incredible experience.

And I wouldn't have spent $25,000 on the flights, but I would have spent 6,000. And do I consider I need to save the 6,000 or do I invest that back into this vacation and the experience that we're going to have and go ahead and book the suite rather than having to try and worry about finding the one property in Paris that will allow you to have connecting rooms?

That's about to be your life. - No, no, I know. But I did see that I think Hyatt in Europe has a pretty good deal where at a bunch of properties, you can get your second room as a family at like 50% off or something. Which is so necessary because those hotel room occupancies are frequently two people in a lot of places in Europe.

It's the fire codes. You can't even find room for three even if the third is an infant. So finding things like that that accommodate the way you need to travel in your life is I think ultimately the best travel hack. - I found, and people have heard this before, this isn't just because you're here, you're not paying me to be here, but like Point Me was this tool and I remember when it came out as Juicy Miles and I was like, I hope one day they change the name of this and thank you.

- You're welcome. That's ultimately my contribution to all of this. It's not actually the decades of knowledge or like my ability to deconstruct things and then reconstruct them. It's that we got to change the name guys. - Yeah. (laughing) But I'm so fascinated because it seemed like so many people tried to do this and it just stopped working.

Airlines hate it. First off, why do airlines make it so hard for people to use their points? And how are you able to make it so much easier? - I don't think airlines make it intentionally difficult to use their points. It depends on the program. We have a lot of loyalty program managers that have been playing on easy mode recently.

We're about to see this in a lot of aspects of the economy. When we had the last recession, loyalty programs had to get really innovative and they had to get really creative because ultimately the job of a loyalty program is to fill seats on planes or fill hotel rooms.

It's to avoid perishable inventories. That's why you have a loyalty program. And we saw 15 years ago, really a lot of creative promotions and really interesting engagement and really honing in on who the customer was and how to leverage their interests and emotions in order to get seats filled on planes.

That hasn't been a challenge recently, the past couple of years not withstanding, but the latter half of this decade, everybody's on easy mode. We saw a lot of loyalty programs go to, we're basically running a coupon program. It's buy nine, get one free, just like at your local coffee shop.

And that's as innovative as they were getting because people had a lot of money to spend on flights and so it wasn't as much of a priority. So I don't know that programs don't want you to use your points. They do because they want you to be engaged with the program.

They want you to be a repeat customer. They want you to have that satisfaction of redeeming your points because then you're going to commit to earning more points. Like those are, that's what loyalty is. All those things are important. But they are burdened by using computer systems from like the Apollo era in some cases (laughs) where literally they're using DOS-based systems still in some cases.

I think one of the most public examples of this, and I think it's to the credit of the program that they shared this, was Aeroplan with their Aeroplan 2020 project, which they started in 2016, knowing that they were going to buy back their loyalty program. They were going to modernize their technology and move off of Resy 2, which was their old reservation system, which Resy 2 because it came about in like the 1980s rather than what they had before.

So moving from that technology that's literally older than us into something more modern took them five and a half years. So it's these huge technical lifts and that's the case with a lot of this. There are still airlines where they are taking their award inventory, and it's a CSV file that they're uploading from time to time into their other inventory system.

Their revenue management systems aren't tied with their airline inventory systems. And if the person who's in charge of uploading the CSV isn't there that week, then award inventory doesn't get added that week. You have to wait until the next week. Fortunately, that's rare. But when you talk about why is this so hard, that's why it's so hard.

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So please consider supporting those who support us. I remember a handful of companies trying to make this easy. Like there were plenty of people that were like, "We're gonna help you find the award flights." How did you guys end up making it work? Was it relationships with airlines? Was it just software?

How is that possible? - Ultimately, I think what it is, without getting into like secret sauce and things like that, although of course we can talk about some of that, but ultimately I think it's the experience and the knowledge. Other people have tried this, but most of the time it's been people who are parachuting into the space, and they're looking at it and being like, "Oh, here's an opportunity.

"I love opportunities. "I'm gonna do this." But they don't have the decades of really deep knowledge of airline inventory systems, and especially as they relate to loyalty management. And that's not repeatable. No one else has that. It's just a handful of people who would have had it to begin with, and we're all working on point me.

So I think that's the thing. It is not an exaggeration when I say that even people who work at airlines don't understand how their systems work, in many cases, as far as it relates to their business rules or their routing logic or their partner relationships. They don't know. We know.

And so we were able to take that knowledge and build out all of those data relationships and those ontologies and those different structures that allow you to then create the business logic and the tool itself. But you have to have all that knowledge to give it to the software, right?

You can't just make an app. - And for people who haven't heard me talk about it before, you can correct me, but I'll give my pitch for it. - Okay, your pitch is probably better than my pitch at this point. - Basically, you've built this tool where I can go in and say, "I wanna go from destination A to destination B "on these dates in business or economy "with this many people." And you'll go out and run the 30 browser tab search on your side and come back in a couple minutes with here's exactly what's available across all the airlines.

And because you've gone in and said, I have Chase points or I have Amex points or Capital One points, here's the cheapest way to book it. And I'm pretty sure it's also like, and here are the instructions on how to transfer them and book it. - Yeah, step-by-step. Here's how I would book it myself.

I think the thing that is worth noting and maybe goes into what you were talking about, how airlines make this difficult for themselves, not just for us, but for themselves. We're not just going out and doing 30 searches. You know, we're pulling inventory from like 35 different places at this point in time.

And we're continuing to refine our data sources. We're also applying all of the routing rules and the logic. So things that airline websites themselves don't always show but we know to work. And then there's things that like, we know that the airline website doesn't show it either. And we're still trying to figure out how we best present it without causing frustration.

And I can give a real-time example. Delta is partners with China Airlines, which is a Taipei-based airline. And I don't know if it's political reasons or technical reasons, but you can't find routings on delta.com connecting through Taipei on China Airlines very easily. It requires a lot of manipulation of the website in a way that no other airport code requires.

So ultimately those things generally have to get booked over the phone if they're bookable at all, but we know that they're there. And so that's something that Point Me can do is we can look at, okay, well, we know the slide is here. We can combine this and we can tell you what the price should be.

And then it's here's the instructions because you're going to have to call. And this is the magic word that you're going to have to say to the airline agent in order for them to be able to find the inventory. And so sometimes we go through that and we decide that this is actually too complicated.

Let's pause this for now. Let's maybe not show this result. So we do a lot of that triangulation, a lot of that verification. If we see something that's available on Airplane's website and on United's website, but it's not available through a third Star Alliance carrier, we go through this whole check process of is this space actually available to Star Alliance?

Is it phantom space? Which is when one of these airline websites is just making things up and they display a flight that's not bookable. So we try and go through and filter that as well and apply our knowledge. So people aren't getting frustrated by trying to book things that aren't there.

- The reason I reached out to you originally to say, hey, is there any way we can get a deal for listeners was because I was like, this is the tool I want to recommend. And so anyone that does the standard monthly membership can get the first month for a dollar with the code, all the hacks.

And that's what I tell people to do. And I would tell them to do it if you didn't have a discount code, but it's nicer for them to get one. - We did want to do that and just make it easy for people who have points because everyone has points and no one really knows how to use them.

And I can teach you how to do it by hand. We have 30,000 blog posts on one mile at a time if you want to do this by hand. I don't know who has time to read 30,000 blog posts though, but if you want to, like there's an option available to you.

You don't have to pay anything to learn how to do this, but there is a market for people who don't want to do that. They don't want to open 30 or 60 browser tabs. They just want to see what their options are, get a sense of what the prices are so that they can do their goal posting as they're earning their points.

And just to be like, wow, great to know that I can do San Francisco, Paris with Flying Blue on the nonstop. Didn't realize the fuel surcharges were going to be $450 a person. I'm going to think about that and be informed and then be able to make a decision and discuss and contemplate their travel plan.

That's really what we wanted for Point Me was to just help people not feel like the space was completely opaque and impenetrable, that they could be informed and make travel choices. - The advice I often give people is, look, if you want to do a quick search, pull up like the main three domestic carriers, pull up United, pull up Air France, pull up British Airways, you could do three searches.

That's not going to get you a comprehensive view. Like by all means, I've done that three airline search and then I've gone to Point Me and I've gotten results that I didn't find. But sometimes you find exactly what you're looking for on search one and you don't need the other 59 browser tabs.

- And that is why I like to say, like start with the Wikipedia page of the airport you want to go to, because it gives you some bounds for your browser tab experience, right? And you can look and be like, oh, okay, so I'm looking at this list. There's not a single Star Alliance carrier.

Granted, you also have to open the tab for Star Alliance carriers. So you're two tabs, but there's not a single Star Alliance carrier that flies here. Maybe there's not a benefit of even opening United or Aeroplan, but like, oh, there's three different one world carriers that fly here. So I can just use the Alaska tool or the American tool or the Qantas tool or the British Airways tool or whichever one I'm most familiar with and most comfortable using.

And I can look at space there. - I can't speak to this product because I haven't used it, but someone emailed me from a company called Flights From, and I pulled up the product and I just looked at it. You can go in and say, all nonstop flights from Paris filter by Star Alliance.

And it actually shows you all the flights there, days of the week, what airlines they are. I'm not getting paid to promote this product, but for someone who wants something more visual than Wikipedia, which by the way, Wikipedia was also my path. I'm always like, Wiki, CDG, go look and look at the airline.

I feel sometimes you get like, oh, this is seasonal. It's not going to start till next November. Whereas if you just search a flight connection- - The seasonal thing is so helpful because I always get people who are like, oh my gosh, you know, I want to fly nonstop to Nice.

It's like, okay, there is one freaking flight from the US to Nice and it's seasonal. And they're like, oh, but my friend just took it. Yes, in the season, right? It's November, it is not the season. - But I did play around on this site for a little bit.

And I was like, oh, this is a tool I would like. I can look at a routing map filter for where does it go? So throw it out there. If anyone uses it- - Yeah, I'm looking at it now. I think that's really fun. The one thing that I would caution with looking at this, 'cause you know I have to have a caution, is that it looks like it includes a lot of low cost carriers, which is phenomenal for thinking about how you can be flexible, but is not going to be good for using your points.

'Cause you generally can't use your points on those low cost carriers. - My hack there was I went in and I just checked like Star Alliance. - Yeah, the same thing that you can do on Google Flights then, where you can just be like, just show me Star Alliance or just show me One World.

- Yeah, I guess Google Flights just does all this also. I don't know why I was looking for a new tool. It's just sometimes I'm like, what airlines fly here? - I actually do think that the low cost carrier feature is super helpful 'cause you often don't see those and they matter.

We used to live in Sicily and like, yes, there were a couple of Alitalia flights, but mostly it was going to be EasyJet or Ryanair or Air Malta or things that you couldn't use points on and you weren't going to find searching other consolidators, unless you knew to look for them.

Knowing where to look is hugely valuable. - Are there any other tools in the space online that you use or recommend people check out when they're trying to think about award travel? - I think it depends on what you want to do. I don't want it to be a plug, but this gets into why we built PointMe because there are things like, I use ExpertFlyer every day, but more for schedules and upgrade space potentially and things like that.

You can use it for award inventory, but ExpertFlyer, like if you know that A space is first class in Alaska and W is economy, you can pull up ExpertFlyer, you can search for it that way. But it requires a lot of knowledge to be able to use it effectively and requires you to know the routing rules.

It can find you space, but it doesn't tell you the combined ability. So if you are getting deeper in the rabbit hole and you're really interested in those kinds of things, I think you get to a point where ExpertFlyer is indispensable for sort of cobbling those things together and be like, oh my gosh, I should actually book premium economy on Virgin Atlantic on this route and then I should upgrade because then I'll get my extra MQMs for Delta.

When you get into that level, you definitely need some of those more technical tools that aren't necessarily as user-friendly, but do have really great information. - Yeah, I will point one thing out that you just brushed over, which is just because you find award availability between two cities doesn't mean that you can always combine it.

So I've had times where it's like, oh, I can go from San Francisco to Paris and Paris to Athens. And I like looked at each individual leg happens to have an award flight that's reasonably priced, but when combining them, it doesn't always work. I know you guys do that in your search, but I would just caution people.

I'm curious what you think about this. Sometimes I'm like, okay, I wanna get to Europe. So let's not look at the ultimate destination. Let's just look at like the transatlantic flights. And that's like how I sometimes narrow it down. I'm not gonna take two stops. So like, I wanna get from San Francisco to Athens.

If you're willing to say, I'm only gonna change planes once. And ideally it's not a six hour flight to the East Coast. You can kind of narrow it down to like, maybe there's only seven routings you could take or 10 routings. You could just kind of systematically check those seven to 10, but just make sure that you check them all together by the end.

Otherwise you might end up finding out that it doesn't actually work. - Right, and the altogether at the end will also matter based on what program you're booking through. That phenomenon you're describing is referred to as married segment itineraries. There are many cases where, let's say it's Lufthansa 'cause they do this a lot, where they'll say, sure, if you are coming from San Francisco, of course we'll make sure that there's space all the way through to Athens for you or vice versa.

And they'll say, this isn't necessarily combinable on a ward because we don't need to make inventory available on the Frankfurt Athens route. It's going to sell out anyways. So there's a lot of that. And it can depend because even within an alliance, some partners have better access to those married segment itineraries, or they are willing to pay a little bit more to their partner to have access to that space.

Or sometimes, especially in the US, this segment is only available to members of our loyalty program. So Delta or United or American might even be able to give you a great discount on that flight from San Francisco to Salt Lake, but they're not gonna make it available to their alliance partners.

So you wouldn't be able to combine it if you then saw space on flying blue. - If someone's thinking, okay, I want to take a trip. Is there an easy way to just get a good sense of like how much it might cost? It used to be years ago, there's just an award chart.

It's like, okay, I could go pull up the award chart for a few airlines. I remember United, it was like every domestic flight was 25,000 points in coach and 50,000 points in business round trip. And it was just so simple. It's like, you want to go to Europe? This is the cost.

I think some airlines still have that. But for the most part, it seems like everything is a mixed bag. How could someone get a sense of what might it cost a family of four to go to Europe without necessarily having to go through all the searching? - So many programs still have award charts.

American Advantage still has an award chart for their partners. And I think that's actually probably a good place to look. They still publish it. And a lot of things are in that range. So if you're like, I have no idea, ballpark, what I should be spending, that gives you a sense.

It gives you a starting place. And Delta or United or Aeroplan may charge more or less, but at least you have the right number of significant figures for the most part. The flip side of not everybody having award charts is that with the dynamic pricing, sometimes you can see really low prices that would never have made it onto an award chart just based off of inventory capacity.

I mentioned earlier Virgin Atlantic will have just bargain flights from New York to London, 10,000 miles in economy. And if you stack that with a transfer bonus and where you're getting a 30% bonus when you transfer your chase points to Virgin Atlantic, it's just a steal. That would never show up on an award chart.

It's not a consistent price necessarily, but it happens often enough that I can speak to it because it's not like a one-off, right? It happens with some consistency when they have extra space on a plane. So the dynamic inventory is hard, right? Because we all like to know how much things are going to cost and be able to work towards them.

I think that's such a key component of loyalty programs. But the little bit of the crumb that you're getting there at least is that there are sometimes some really great values on the other side, especially domestically, I think where you get some prices that you wouldn't have anticipated. - When people listen, you're like, okay, I now get it.

I feel confident about how I could start to plan this trip and book this and find availability. But now I gotta go get those 300,000 points. We've talked plenty about, okay, well, you can get the card that optimizes where you spend your money. You can get some signup bonuses and keep on top of what they are.

And I try to share that. Any other hacks or tips or tactics that you like to share with people who are trying to get to that mileage goal so they could take the trip? - Yeah, that's really a fun question. So I think in general, I like to encourage people to be opportunistic.

And there is a great signup bonus to take advantage of it. I'm also at a place where I recognize that people who are doing this also have full-time jobs. And so you don't necessarily want to be in a situation where you have so many cards and they're hard to manage and things like that.

But I think it's important to think about it. And if you're planning like an extended family trip, maybe you have that conversation with the extended family and say, "Hey, this is the trip we want to take. "It's going to be this many points. "In our household, we're going to get that "because we're both going to get this card." That might be an option for you.

You don't want to be in charge of your family's finances overall. It's a bad, bad life choice. But to think about that and to be sure that as you are getting credit cards, that your points are ultimately combinable. I think this is especially important if you have a family or if you're more than one person in general, is, okay, it doesn't help you to have 50,000 points here and 60,000 points here and 70,000 points here.

You may find yourself in a situation where you have half a million points and you don't have enough points for a single round trip international ticket because they're not combinable. So that's, I think, the second level thing is don't just get the Chase Sapphire Preferred because it has a big signup bonus.

Like, that's great, do that. But then when you go to get your next card, look at, okay, well, where could these points move to? I want to make sure that my next card, I can also move those points to the same places or it bolsters one of those balances there.

And just make sure you have a couple hundred thousand points in a program or able to get to a program before you move on to the next thing. - My advice has been, you can now, for most airlines, book one-way awards. I always say, instead of trying to book like, oh, we're two people and we have enough points in two programs, book the one-ways together, both be on the same itinerary with one program, and then the return with the other program instead of trying to book each person separately.

- Yeah, absolutely. Especially if you have one person who's not as confident of a traveler or you have extended family members. I always talk about, like, when we're traveling with our moms, it's totally different than when we're traveling just with each other. And I think that that's key, like, staying on the same itinerary.

And again, are you getting points in a program? So maybe it's more thinking of like, am I getting points in an account, right? Because if you have 50,000 points in United Mileage Plus and your partner has 50,000 points in United Mileage Plus, you still neither together nor separately have enough points to do what you wanna do.

If you have 100,000 points in one account, you have more options. - Alyssa actually reminded me, I know Capital One, you can share points with anyone. So if you have Capital One points, you can. With Chase, I think it's within your household. So if you're both accumulating Chase, you can share within your household.

Amex, most of the actual airlines though, make it incredibly difficult and costly to share points. So another bump to the transferable points game is that it is very hard. If you have American points and someone else has American points, combining them for a trip, a few of the international carriers have programs for this, but it's very hard.

- Yeah, you should combine them before they get to the airline. The nice thing though, is that for the most part, all the airlines will let you book tickets for someone else. And we hear this all the time because we have the grandparents who wanna pay for a honeymoon and they're like, "How do I get my Amex points?" To my granddaughter, it's like, "You don't.

"We'll take your Amex points "and we'll move them to maybe your AeroPlan account "and then we'll book the flights for her from your account." You don't have to transfer them to other people and pay transfer fees. - But if you and your spouse both have, let's call it 50,000 Amex points and you wanna book an award that's 100,000, there's no good answer.

You can't combine Amex points. But my version of a hack, which I think is still possible, is that if you add your spouse as your authorized cardholder, then you can transfer points from Amex to their accounts. - Correct, yeah. If it's an authorized user, then you can transfer them to the same account.

- So you can't combine the membership rewards balances, but if you're transferring to Delta, you could transfer them both to the same Delta account and book from there. - Right. I would say if you are going to do that, and you know you're going to do that, there is a high potential for the airline to put a fraud alert on the account if you're getting back-to-back transfers from different accounts in short succession.

They'll resolve it. It's not going to be actual fraud. It's just going to be something that needs manual approval. So if you are in a situation where it's like, "Oh my gosh, I know that I'm going to book this flight," or you find this diamond in the rough award space that you would never have been able to book, and you're moving all these points all around to temper expectations, because it might be 72 hours before those points are cleared for you to book it, in that specific example.

I don't want to dissuade anyone from earning points. - No, no. (laughing) - It's good to know that there can be pitfalls. - One important thing, actually, that came up with another listener was there are a lot of mileage programs where it's like you can't transfer points in for 72 hours, or there's some rules about how long the account has to be open before you can book something.

So one suggestion I have is if you have Chase, it doesn't cost you anything to go to a dozen or so Chase airline partners and go open all of those mileage accounts now. - Yeah, why not? - I don't know if you know exactly which ones, but I know there are at least a few airlines where it's much better to have had the account open than open it when you need it.

- Yeah, I would actually say with almost any of them, it's better. And again, this is just security checks are all driven by algorithms. It's obviously more suspicious to have a brand new account that was just opened and now is receiving points from non-flight activity from multiple sources in 90 minutes.

Like if you're a computer, you flag that too. So you can just avoid some of those triggers by opening the accounts early on, maybe make a purchase through the airline shopping portal early on. I don't want the takeaway from this though to be that like airlines are super concerned about fraud and that you're going to run into problems when you're reviewing your points.

This gets into like the edge cases of it. Most people are not going to have these problems. It can happen. So you might as well season the accounts a bit. - But there are some airlines where I think you can't actually do anything. Even if they don't flag you for fraud, they just have a rule.

It's like your account has to be open for a week or that kind of stuff. - Yeah, and there's others where can't search award space unless you have a couple of points in the account. And if you can't search award space, that means you can't book award flights, but you don't necessarily need to have the full number of points.

But if you have two points in there or five points because you bought something through their shopping portal and posted the points there, then you can have full functionality. - And the other one is I've had some issues. I can't remember exactly why, but my name is long enough that sometimes when I try to add an airline to my Amex account to transfer points out, it's like, ah, it didn't work.

So I would also say, if you go and create an airline mileage account for all these airlines that you can transfer to, you can also go and link those accounts to your Amex, Chase, CapOne account as well. And the thing I'm ultimately trying to help everyone avoid is you don't wanna go and find a flight and be ready to book it.

Finally, I found the availability. - Right, and now it all falls apart. - Now I need to wait three days for my account to be active or my account was active, but now that I linked to Amex, there's like some error and I have to get Amex to help resolve the error before it works.

So I like to put all those pieces in place. - That's actually maybe the next level of things is when you are applying for credit cards to apply for them with the name that is on your secure flight information. And this might seem obvious to people. Like American Express will issue you a credit card as C.

Hutchins, but Flying Blue won't allow you to create a Flying Blue account with C. Hutchins. It needs to be Chris or Christopher or whatever is on your passport. And so when you go to transfer the points, they won't match. And so Flying Blue will send the points back. And I think a lot of us with like shorter names or I have two middle names, so I just never include them on anything because it's too complicated.

But it's like, oh, I'm just applying for this credit card. I'm not thinking about using my full legal name as it is on my passport. Just to add something else to make it a little bit more complicated for everybody. - Any other travel points, miles, broad speaking, tactics, tricks, hacks to share before we wrap?

- I think the biggest thing to think about is that you can absolutely use your points. People get so overwhelmed. They get so wrapped up in trying to optimize and find the very best example, or they see influencers who are doing things and they think that there's only one way to redeem their points.

At the end of the day, the best use of your points is one that allows you to have an experience that might have otherwise been out of reach. Whether that's a trip that was expensive or a trip that was difficult or a trip that was super aspirational and lovely and to just not be afraid to go ahead and book it.

It's not a contest, it's not a race. And there are some tremendous ways to improve your life through these experiences, just go for it. If it's not perfect, then maybe the next one will be better. And you learn so much going through that first process of booking an award flight that you didn't apply to the second.

But I find so many people are too intimidated to book the first one. - And hopefully, I think people can leave this saying, "Okay, I feel like I understand how the system works so I can do some searching myself. I know of at least one tool that you guys have built that will make this a lot easier." When do you think that actually makes sense for someone?

- The reason why we set a point up the way that we did and why we're happy to, for certain audiences like yours, give a really significant discount to use it for a month is because we are pretty evangelical about using points as an option. So for a dollar, you can spend a whole month clicking around and just sort of seeing what the options are.

And we have the instructions laid out for you step by step by step. And I do truly think that for most people, if you just try, maybe even take a theoretical trip, one that you're not emotionally committed to yet, but you've just thought about wanting to take and go through the steps, and maybe you're not actually transferring your points, but you're sitting there and thinking, "Okay, this is the point where I would go to my credit card company and I would transfer the points.

And okay, I see now how I would book." And just play with it and build that confidence in doing it because it doesn't have to be overwhelming. There's a lot of information. There's a lot that you could do. There's a lot of ways that you could maximize the heck out of it.

At the end of the day, it's not that much more difficult than other things that you'd successfully do every week of your life, right? You're just applying that skillset and those abilities to something different. And you only are able to do new things when you practice them. We work really hard at Point Me to give you all the tools that you need to be successful.

We're checking to make sure that it's actual flights that you can actually book with the points you actually have. And we have step-by-step instructions, including little videos of like, "Here's where you go to click." So ideally, anyone should be able to do this. And I laugh because we say this, but it's true.

Like we've tested it with our moms who are not the most tech-savvy group of ladies out there, although we love them. So I do really hope that by using the self-serve tool there that for a very moderate price, you're equipped and you can book travel. If you are somebody though, who has a lot of points and a lot of different accounts or with different family members, or you're planning something that is complicated, but you know specifically what you wanna do, it's just too complicated and it's too intimidating.

We do have a team of people that can book that for you. It's obviously much, much, much more expensive than the self-serve tool, but that is an option that's available as well. - Cool. I feel like we covered a lot. I'm sure I'll have some questions. I'll do the next Q&A as a follow-up to this.

If people have questions, I might even send you some. But one thing I like to do before we wrap up every time is you've been to a bunch of countries, more than me, more than probably most people listening. Are there a couple of places that you think might not be on someone's radar?

Like you mentioned earlier, your new focus on travel isn't just the place everyone goes. Are there a couple of places that you'd say people should check out and maybe something interesting they could do while they're there that might make it an exciting destination? - I think that Malaysia is really underrated for people who are looking for a trip to Asia.

Incredible food, really welcoming people, fantastic beaches on a lot of the islands. I think that that's some place that people should really consider. And then I'm, of course, biased because I've lived in Sicily and people go to Italy, but they don't really go to Sicily to the same extent.

And I think if you are an independent traveler or you're open to, again, having to work for it a little bit, that there's some really incredible experiences there, some agriturismos that you can stay at where you're getting a much warmer experience than you'd find on a lot of mainland Italy.

And it's an interesting history and archeology and all those things, too, that not as much on the tourist trail. - Cool. Tiffany, thank you so much for being here. This is great. I appreciate it. - Of course, thanks for having me. I hope it was helpful and demystifying for people.

(upbeat music) - I really hope you enjoyed this episode. Thank you so much for listening. If you haven't already left a rating and a review for the show in Apple Podcasts or Spotify, I would really appreciate it. And if you have any feedback on the show, questions for me, or just wanna say hi, I'm chris@allthehacks.com or @hutchins on Twitter.

That's it for this week. I'll see you next week. (upbeat music) (electronic beeping) (electronic beeping) you you