This year's spring break in Hawaii turned into one of the most strategic and rewarding travel experiments I've ever done, mixing points, promotions, and perks to pull off an epic vacation, which included what might be the best hotel experience we've ever had. So I'll walk through every detail of how we made it happen so you can use these takeaways on any trip you're planning.
But that's not all. I'll also dig into a few new ways I've been earning a lot more points recently, some big airline program changes, a way to save on flights, a few last-minute Mother's Day gift ideas, and more. I'm Chris Hutchins. If you enjoy this episode, please share it with a friend or leave a comment or review.
And if you want to keep upgrading your life, money, and travel, click follow or subscribe. So I got such great feedback from tons of you when I did the episode a few weeks back about, it was a little bit off the cuff, it was a little bit last minute, and it was about a few things that were just happening recently going on.
It was a little bit of a mishmash and people loved it. So I'm going to do that again today. And I'm going to try to do it once a month or as often as there are things to talk about. First, I'm going to talk about our recent spring break trip to Hawaii.
There are a lot of lessons in here on travel, getting upgrades, saving. So I think it's gonna be really helpful for anyone, even if you're not planning on going to Hawaii or repeating this trip. For whatever reason, we didn't have any plans for spring break. I'm not sure this was only a few months before we were leaving.
And so we decided we wanted to try to do something. And we had so many options for how we could do the trip. We had lots of points and miles. But when it came to where we were staying, we actually had a handful of Hilton free night certificates from Hilton cards.
We had a bunch of Hyatt and Marriott points. We had this fractional home with Picasso that we could swap either through Picasso, or we actually have this third party network of vacation homes called third homes. And we had some keys there. And then we'd actually we've bought into exclusive resorts membership, which is like a private vacation rental club.
And our initial idea was, let's find a place we can go that we're excited. But let's use the things that are expiring soon. So maybe those were our third home keys or Picasso nights or Hilton certificates. And so we started with third home because we have the ability to book a really nice property anywhere in the world.
But we have to book it by May 23. That's when our all of our keys, their virtual currency expire. And we couldn't find anything for spring break. So if anyone's looking for a nice villa or a home, and you're really flexible on dates, take a look at what's on third home, shoot me an email, maybe we can make a deal.
So we moved on. And we were like Hilton, Marriott, Hyatt, what should we do? And it was impossible, but not because it was hard to find availability. There was a lot of availability all over the world. But it was impossible because there were just too many options. And it didn't feel like we were choosing our vacation at all.
So we did a hard reset. Amy and I sat down and said, okay, it's spring break. We have two young girls. What do we want to do? Where do we want to go? And the requirements we had were we just wanted a direct flight somewhere warm, where we had some pools or beaches, because we just didn't want to be doing a bunch of city activities when we had to come back for naps with young kids who, by the way, are really excited to swim all the time right now.
So we were like, it looks like the best options are Hawaii and Mexico. So now that we scoped it back really, really tight, it felt like it was a much more manageable search. Now, because we have kids, we were looking for places that had room for four people. And yes, we could do one hotel room with two queen beds.
But our kids throw their arms around at night, no one can share a bed with one of them when they're sleeping. It's kind of a mess. And there's actually a whole episode coming out soon about kids and travel. But we were looking at our exclusive resorts thing. And we found five nights at a three bedroom place at the montage in Kapalua Bay in Maui.
Now, we've never been to Maui with the kids. We've only been to Maui once ourselves had an amazing time. It seemed like that was such a great option. And funny enough, we were like, well, we don't really need three bedrooms. And I was talking to my parents and they said, Oh, like, who's gonna stay in the third bedroom.
And you know, there's been a laughing joke about whether they invited themselves or we invited them. But at this point, they were kind of excited to come with us. Girls were excited to be there. We thought if they were here, maybe we could slip away for dinner one night.
And they could help with the kids. And so we thought, great, we could just go for five nights to Maui lined up during the week of spring break. But right in the middle of all this, I heard Robert from Milenomics talking about how his stay at the Four Seasons Lanai was literally everything you could ever want a nice hotel to be.
And so I immediately checked it out and thought, you know, I've had some friends that have been to Lanai. They thought it was amazing. Maybe we should go. Four Seasons is usually pretty out of our budget. You know, we can't use your points. You can't use your miles. There's not really a deal to be had.
However, maybe that's not the full story. So we looked and it was out of our normal price range. The initial price was about $1,400 a night, which depending on your budget, maybe that's cheap. Maybe that's astronomical. But that price wasn't the full story. And I want to break it down because I think sometimes you could find a hotel and say, wow, that hotel is 800 bucks a night.
That's way better than this $1,400 a night room. But when you start to peel back all the things that might come with that $1,400 a night room and the end cost you'll pay to stay there. In this particular case, I think you're going to be very, very surprised. So first we were looking at booking the hotel through the All The Hacks hotel upgrade program.
Thanks to our partnership with Savanti, we're able to offer anyone access to a ton of perks and benefits and upgrades at luxury hotels, over 5,000 of them around the world. So if you go to hotels.allthehacks.com or find the link on the website, the password is perks. You can go and you can just search for any hotel.
So for example, I'm searching right now and I see the Four Seasons Lanai. And the one thing I'll tell you as a way to know how to use the site is there's a list of rooms and rates for each hotel. Make sure you click the full description for any of those rooms.
And if you're looking, it usually says refundable, breakfast included, and then some phrase, it could be virtuoso, cadence preferred, inspirato, like there are different rate codes that are our partners. And so those will dictate what benefits you get. But usually the benefits are upgrade, early, late check-in, early check-in, late checkout.
Most of those are subject to availability, but sometimes for the right stay at the right dollar amount, you can confirm them in advance. But it almost always also includes free breakfast and a property credit. And as you're scrolling through, you can see what it includes. It'll say free breakfast, one spa credit available at this spa, or it'll say early check-in or $100 property credit or anything like that.
So in addition to all of that, because of the relationship a lot of travel agencies have, you even get usually an even higher upgrade likelihood than booking through something like Amex, fine hotels and resorts. So for the Four Seasons Lanai, you know, it said upgrade was going to be a thing.
And when you look through the description of the room type, it also said you're going to get free continental breakfast for two guests, category upgrade spa credit. Now, sometimes if you look at these rates, they say virtuoso, which is a travel conglomerate, you know, collection of hotels, you can go to the virtuoso site and get even more details.
The virtuoso site said daily breakfast, $45 per person, up to two guests, $100 resort credit can be used anything, anywhere, and early check-in, late checkout, and an upgrade. There was also another rate for Cadence, which is another travel group, and it said daily breakfast for two, hotel credit, upgrade, free transportation, and then $100 credit.
So it's basically the same thing. So if you could book either one, it doesn't really matter which one you book. Rates are usually cancelable. So we ended up booking this, reached out to the hotel, asked them about the upgrade. Sometimes you can do this in advance, and they will confirm your upgrade if there's enough availability.
Maybe they'll wait till you check in. But definitely, if you're doing a booking here, and the value of the booking across your stay is in the, let's call it thousands of dollars for the stay, then reach out to us. And we'll try to do what we can to see if we can help you secure an upgrade in advance.
One trick here is the upgrade is often, you know, one, maybe two categories. So if you book the cheapest possible room, you might go from garden view to ocean view. But if you were to book, you know, the oceanfront room, the only real thing above that might be a suite.
And so a one category upgrade could be really, really lucrative. We ended up getting upgraded from a garden view to an ocean view, which was a huge jump, right? That $1,400 room, if we had booked an ocean view was $2,300. We knew we were going to get at least a partial ocean view in advance.
And then we found out, you know, when we checked in that we got an ocean view might have even been actually, I think it was an oceanfront. I'm not sure because they didn't say oceanfront, but the ocean was right there. But that's just one of the things that you can layer on to make this a better deal.
The rest of them come with the specific property. And you have to look at the website of the hotel to know this. But if you look at the Four Seasons Lanai website, you'll see that until December 31st, 2026, all of the room bookings also include round trip flights from Honolulu to Lanai.
And that's on a public airline that really feels a lot more like a private airline called Lanai Air. They have two different planes. I think one of them has six or eight passengers. One of them has more like 20. And it's a true VIP experience. And those flights are all included.
So I'll talk about the review of everything and that experience. But that was part of the stay. Then there's a bunch of packages on the Four Seasons website if you click offers. And one of them was the Discover Lanai package. And so it's basically good from, I think it's the rest of this year and all of next year except Christmas and New Year's.
If you book a three-night minimum, you get an additional $200 a day credit or $400 a day if you're in a suite. So there's that credit. And then last, right now, one of the restaurants is closed. And they're doing a little bit of construction at the front of the hotel.
Honestly, I'd be surprised if you even really noticed it audibly. You know, it's visually you can see the entryway to the hotel outside as being redone, but it affected our stay in zero possible way. But until August 31st, 2025, they say to thank our guests for their understanding. Each guest will get a complimentary daily activity to enjoy the island.
That includes horseback riding, hiking, target sports, aerial experiences at the adventure park. And they also have a separate restaurant they're setting up where Malibu Farm, which is normally just lunch, is also doing dinner. So if you tally everything up, we ended up getting free breakfast for two people every day, which was $132 credit that we could use.
We got inner island flights that I would value at about $100 a person. Plus, we got $200 a day credit. Plus, we got $100 per stay credit from the All the Hacks Upgrade program. We got the upgrade, which I'm not even going to include in this value. Plus, we got a free activity every day.
So my daughter got to go horseback riding one day. And then we went to the adventure park, which is kind of like a ropes course one day. So when I added up all of those extras, the total price of the room was a lot less. So all those extras divided by the number of nights was about $700 a night, which means that our $1,400 a night room included $700 a night of benefits.
Now, maybe you don't value all these benefits the same way we did. But we certainly spent all the credits, we would have done a few activities, we would have had to fly to the island, and we did our best to eat massive breakfasts. Though I will say, kids breakfasts were also included, and the kids could order whatever they want.
I'm not even including that. So when you factor all that in, if it's really only $700 a night room, is that expensive? Yes. But is it a lot less expensive than $1,400? Also, yes. And so I thought overall, it was an amazing deal. We booked it. And I will get to the review of it in a couple minutes.
But preview, it was amazing. So once we booked our flights, we had three nights in Lanai, then we had, we reduced the stay at the Montage to four nights. And then we were just going to take the ferry between the two. So, you know, we could fly from Honolulu to Lanai, take a short ferry, and then fly back home from the island of Maui.
So now we kind of had the infrastructure of where now we had to get there. Now, flights seemed a little daunting at first, because it's spring break, we looked at the dates, and it was pretty expensive, right? Each way to Hawaii, whether we were flying to Honolulu or Maui was like five, six, as much as seven or $800 for direct flights, which was not ideal.
And certainly not something when you're booking four seats that you're really excited about. So I looked at using points and miles, as I always do. And it turns out that some of those flights that were five, $600, I could book on Hawaiian Air using Alaska points for just 26,500 points.
So, you know, let's call that ballpark, you know, $300 of value, way, way better deal. So found that and book that on the outbound. On the return, it was a little less easy. We did find that same price, 26,500 miles for flights that were normally $600 or $700. But it was only one stop.
So we couldn't fly direct from Maui to the Bay Area on any carrier on the day we wanted, even if we stayed an extra day without spending $700 or $800. So that was off the table. So we looked, we said, okay, we could spend 26,500 miles per person, fly through Honolulu, not the end of the world.
But when I was doing this searching just for fun, and I don't know what made me think about it, I looked at searching from Honolulu home on the off chance that maybe there was an inter-island flight that was really cheap and we could get direct home cheaper. And it turns out there were four business class flights on that same Hawaiian air flight going home.
But when I searched for Maui, there were only two. Now, this sometimes happens. It turns out the flights inter-island from Maui to Honolulu only have two seats for business class award space. But the larger flight from Honolulu back to Oakland had four seats in business that you could book with points.
So we ended up booking two flights, one on the like, let's call it the 9am flight from Maui to Honolulu and one on the 945. So my wife and I were going to split with one kid each, fly to Honolulu separately. And then on the way from Honolulu back to the Bay Area, we'd all be together.
So that was the way we were able to get four business class seats for 40,000 points each. And the limiting factor was just flying from Maui to Honolulu. Now on some airlines, you can just call and you could say, hey, could you just book us an economy for this leg?
And no problem. But in this particular case, we couldn't do that. Hawaiian and Alaska, whatever way their systems work, they didn't allow that kind of mixed award booking. And so we had to book it separately. But if you find this scenario on other airlines, it is often possible to call them or even sometimes use the multi-city search and book a economy first leg connecting to a business class second leg.
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But right now, you can transfer from Amex to Hawaiian, and Alaska and Hawaiian are in the middle of a merger, which is why a lot of this availability exists, and you can transfer from Hawaiian to Alaska. So for the time being, and I'll cover that in a couple minutes, going from Amex to Alaska is possible.
Now, unfortunately, you know, we have two young kids, we try to do bedtime in the, you know, 7:30 range. That flight arrived in Oakland at 8:30, and there were no other good options to get home earlier, except for these direct flights that were eight or $900 from Maui straight to the Bay Area.
However, we did try a backup tactic. We booked a separate flight using Southwest points for 26,000 points from Maui through Honolulu back to San Francisco, but we would have much preferred to take one of those direct flights. But like I mentioned, they were $800. However, I did have one idea, and that's based on the same day change rules of Southwest.
So Southwest had plenty of seats on the direct Maui to Oakland flight, and we would love to have taken it, but at $800, it just didn't seem worth it. I'd rather fly through Honolulu in business class for 40,000 points than pay $800 to fly direct. However, there was a Southwest flight from Maui through Honolulu back to Oakland with terrible times and layovers, but it was only 26,000 Southwest points.
So I booked us on that with the goal of checking at midnight on the day of departure whether that space was still available on the direct flight. And if so, Southwest allows you, if you have the right fare class, to transfer to another flight on the same day between the same two airports.
So going into the trip, we had a plan of direct flight to Honolulu, change to Lanai Air, take a ferry over, and then coming home, we had two options. We could either fly business through Honolulu, or maybe we would get lucky and we'd be able to change it to direct.
And so that was the plan going in. So let's talk about the experience. About three, four, five days, I can't remember exactly before, I got an email from Hawaiian that said, "Hey, do you want to bid on an upgrade from the Bay Area over to Hawaii?" And I thought, "Oh, I wonder how much do you have to bid, right?
Like there's some price at which I'd pay for that upgrade." And I looked in, and there was no way to bid any less than $325. And I thought, "Gosh, if they're looking for us to bid, there must be a lot of seats." And I looked, and there were four seats available in business.
So I went on and said, "Were there available in miles?" And two of them were. So it was a bit of a dice roll here, because you never know what will happen. So I thought, "What if I book two of those seats in business and hope that those other two seats show up and I can book them before the day of departure?" Because at the end of the day, the difference between 26,500 points and 40,000 points was way less than paying $325 for an upgrade.
We didn't really need the upgrade. And normally we don't like to separate on the flight. However, we did have our youngest, and we did have a hypothesis that she might nap better on a lie flat in business. And I personally had never flown Hawaiian in business. So I thought, "Get to experience it.
Daughter might get some sleep. Only an extra 13,500 miles a person for two of us." So unfortunately, those other two seats never did open up. So it was just me and one daughter. I did offer my wife to take it. But she said, "I would rather you take our youngest and deal with her trying to nap on the plane.
And I'll stay back here with our other daughter." So I'll speak to the business class experience. But you know, wife said the coach experience was also great. So business class, great food. I wouldn't say it was anything to write home about, but good options. There were not a lot of amenities for a, what was a daytime flight.
You know, I didn't lie down to go to sleep. But I did notice that in coach, they were serving actual meals. You get a full, I think it was a breakfast sandwich. So that was nice. I feel like a lot of times, you know, if we were on the Southwest flight, we might've gotten a few snacks, but we wouldn't have gotten a real, real kind of meal sized thing.
So that was great. But the real highlight of the entire flight was Starlink. This was my first flight on an airline that has Starlink. And I cannot explain how incredible it is. It seems so unnecessary and not that exciting to have Starlink on a plane, right? Like it doesn't seem like it would change your experience, but it literally just felt like you could actually work as if you were at home, work as if you were in a high speed internet anywhere.
And I was so productive. And about a week before, a friend of mine told me he actually opted to change planes on the way home from Hawaii, so he could have Starlink. And at the time I was like, that's crazy. I would fly direct over changing planes every day of the week.
And now I'm like, if I had no children with me, I would definitely consider changing planes for a long flight for the quality of the productive work I would get done. With kids, I think it's a different story. But I'm just, I'm so excited for the day when Starlink is on all the planes.
I know United's announced it's coming. It's going to be incredible. So land in Honolulu. Right as we land, we got a text from Lanai Air from someone saying, we're ready to meet you by baggage claim. We're ready to help you move your bags over to a private car. We got in a town car.
It was actually a suburban, drove us over to the private terminal and waited for maybe one hour. We actually landed early and our Lanai Air flight was about two hours later and they were able to move us to get on an earlier flight an hour earlier. And it really does feel like you're flying private.
I will say, unfortunately, they have these six passenger planes that look like they are truly private that I thought would have been a fun experience. But would I rather have gotten to the hotel earlier and gotten on the 19 passenger, I think, flight that was leaving earlier? Yes. And so the only thing that felt a little less private like was the fact that it was a larger plane with more people.
But you know, you get to the plane riding on a golf cart out to the tarmac. It just was such a amazing experience to be included in the cost of your hotel room. So really, really awesome. Obviously, no real service on the flight. It wasn't very long. I think, you know, maybe 30 minutes landed, got picked up by the hotel and and headed off to the resort.
For anyone not familiar, Lanai is a very interesting island. It's about 140 square miles, about three or 4,000 people. But the most interesting thing is that it is almost entirely owned by Larry Ellison, who founded Oracle. He owns about 98% of the island. It used to be a pineapple plantation, almost the entire island.
And the family or company that owned it, when the pineapple plantation shut down, they had to find a new owner, and he bought the island effectively. He doesn't own 2% of it, which is kind of the downtown Lanai city where a lot of people live. There's two main hotels, there are two Four Seasons hotels, and there's one smaller hotel downtown.
One of the Four Seasons, we didn't experience it at all, is called Sensei, and it's adults only. It's more in the middle, is a much more wellness-focused resort. It looks amazing, but it's adults only, and we had our children, so it wasn't really a thing we were going to experience.
And as soon as we got to the resort, it was about a 20-minute drive. From that point forward, it was everything you could ever want in a hotel. The staff was incredible. The room was incredible. Every little detail was just perfect. It made you see things in other hotels that you've stayed at differently, thinking backwards, and unfortunately probably thinking forwards, because they just really care about every detail.
So, so great with kids. I can't even explain how great it was. They'd asked about our kids' names and ages, and in the room were small robes and small slippers that fit them. They lined up sponges with the letters of their name in the bathtub. Every place you went had coloring mats and stuff.
It was dialed in for kids, but it was so relaxing for adults. I think my wife said somehow they managed to like make an adult and kid experience magical for both sets. And it was just, I haven't experienced that before. The food was amazing. If you do go, the smoked wagyu dumplings at Nobu, which is one of the restaurants there, are just amazing.
And within the $132 breakfast credit, you can get this salmon caviar breakfast spread that was also amazing. Pretty much everything was amazing. I don't want to list it all, but highly, highly recommend lots of cool free things just to do walking around. You know, they have cultural activities from ukulele classes to palm weaving.
They have really cool birds that they've adopted that were kind of rescue birds all over the property. They are walking around with them from day to day. They have a couple koi fish ponds and you can pick up some food at the front desk. We probably fed koi fish a hundred times.
Um, they really try to be sustainable. So they give you two Four Seasons Lanai water bottles, um, in the room, really nice Yeti ones, uh, that you can use throughout the property where there's water filling stations and free sunscreen and free aloe. And God, I just can't express how awesome this hotel is.
Like, I think it is very likely that we will go back because it was just everything you could ever want in a hotel. Like the description that we were sold on is exactly what we got. And then within about a 20 minute drive, all of these activities that for right now, while one of the restaurants is closed are free were really great.
So we went and did an adventure ropes course with the kids. Um, my wife took one of our daughter's horseback riding. There was so much to do. And interestingly enough, probably not what you're expecting as far as activities. The island of Lanai actually has a lot of invasive axis deer, similar to Maui.
If anyone remembers, I've talked about Maui Nui Venison, which was a sponsor from the show a while ago, still a brand I love and their products are incredible. And so if you are interested in Venison, check out Maui Nui Venison. But at the Four Seasons Lanai, there were actually people there for hunting trips, which is not what you typically think of at a Four Seasons.
So it was really interesting to just see people walking through the lobby in their full camo gear, carrying their bow or rifle cases, you know, checking into their room, uh, or, or having just gotten back from a hunt. And then the next day, see them just relaxing at the pool.
So if you enjoy hunting, but also need a family friendly vacation, this would also be a great place for you to go. We had an amazing time. I just can't say more about how great the property was shout out to the entire staff there. And this was not a comp to visit.
We paid for this visit, uh, out of our pocket. So, um, I wish it was, if anyone listening wants to comp our visit anytime we'd love to go back, but, uh, I think we would even pay for the trip again. It was just such a great experience. When we finished, we took the ferry over to Maui, which was about an hour boat ride.
Really nice boat ride. Um, little bumpy, but not enough to stop both of our kids from falling asleep. And where it comes into the harbor, there's a little bit of an area with the little shops and an ice cream store and, um, maybe a couple of restaurants. We grabbed a snack, hopped in a lift and went up to the montage and also incredible property.
This was a little bit of a different experience, right? This time, one, my parents were already there. They got there about an hour before us and met us there. And it was a three bedroom condo at a resort property. And there's something interesting about the montage in Maui is that my understanding is it used to be the Ritz vacation club.
I didn't fact check this, so I could be wrong, but because of that, it was historically a place where most people staying there were owners and a lot of the condos have kitchens. And so it kind of was missing some of the kind of restaurant options you would see at a big resort like this.
I think there's just one restaurant and poolside dining. And so we did go to the restaurant one night. It was great. It was expensive, like you would expect, but it was good food. The rooms were excellent. So we had this three bedroom place with ocean view. I love how at least exclusive resorts, I don't know if their villas are different than others, but you know, every room has a Sonos, they have a full kitchen, they have laundry.
It just was really dialed in. But because it was on the resort, you could still order room service if you needed to. You still had daily house cleaning. And so that was awesome. The experience of being able to have multiple bedrooms with kids and in our case with my parents, but also be at a resort where you can just walk very close to massive pools and lounge chairs and get poolside service was really, really great.
The pools are awesome at the montage in Maui. I want to say there's four tiers of pools. There's like the adult pool and then three tiers of kids pools with little waterfalls between them with rocks that kids can jump off of, weird little water features and multiple hot tubs, shallow section for younger kids.
It was definitely more of a family vibe than some hotels I've stayed at, but we were there with our kids. So that was exactly what we were looking for. And this was also true at the four seasons. But you never felt like there weren't chairs. At the montage, they told us explicitly they had this policy.
You could go down seven o'clock, you could sit in chairs. And if you don't use them by nine o'clock, you lose them. So I appreciated that they had a policy that was stated. So but because there were not so many people there when we were there, at least they had enough chairs for people never felt like it was too crowded.
There were some cool other things to do. So I'd highly recommend if you go to the montage, there are these tide pools that you can walk to not very far of a hike. And it was really awesome. It was like a little rock scrambling down to some tide pools.
That was great. The beach is right next to the property. All the beaches in Hawaii for anyone who hasn't been are public. So they don't operate quite the same as some of the beaches you might have been to at a resort in Mexico, where the resort is kind of really operating the beach.
And so in this case, I think the montage, you could check in at the beach shack and you would get, you know, two chairs and an umbrella free for staying at the hotel. But they also had a place where you could rent snorkel gear and paddle boards or even wetsuits if you wanted them.
Our girls do not love the ocean and are a little bit shy when it comes to big waves. However, in this particular case, the waves were pretty calm here. The waves in Lanai were a little bit bigger. The waves in the montage were calm enough that we actually got our girls out a bit, but not nearly enough to go snorkeling.
It looks like there was some awesome snorkeling. Didn't get to do it on this trip. Hopefully, maybe next time girls are more excited. The other cool thing about this location location is there's a restaurant called Merriman's. It's pretty well known. I think they have multiple locations on different Hawaiian islands and excellent restaurant.
And it's, you know, five, 10 minute walk from the hotel. And if you walk a little bit further, there are a few other restaurants. And so really nice that you could walk to a great restaurant. Now, Merriman's is also so popular that it's very hard to get a reservation.
And we did not plan in advance and it's quite expensive, but they actually have an outdoor part of the restaurant called On The Point, which is no reservations, walk-in only, and honestly, I think better views because you're out right on the water. We ate there twice. It was excellent.
Great happy hour menu, which times very well for having children. For breakfast, we walked to this Island Vibes acai shop one day, which was great. And for the most part, we ate breakfast in the room because we had a full kitchen and it was just easier. We did take one trek one night to a restaurant called Monkey Pod, which is operated by Merriman's, also a big restaurant conglomerate in Hawaii.
It was awesome. Live music, really fun, great cocktails, would highly recommend it. That said, it's in the middle of like a shopping center and shopping center vibes is not exactly what I was going for with a relaxing Hawaiian vacation. It kind of felt a little chaotic, but the food was great.
But it was really easy to get to because one of the perks that I think is a little underrated at the montage and why I think anyone listening should always dig into the details of all the perks at your hotel, because I brought this perk up to multiple people we met in the pool and no one had heard of it.
But they have a Cadillac XT6, which is an SUV that seats six or seven people. And you can just borrow it anytime you want for free for four hours. You couldn't book it, but they kind of told us no one's ever using it. So we picked it up, went and got groceries.
We picked it up, we drove to dinner, had a nice dinner and came home. So really, really underrated perk that you would have found on the website, you would have found if you asked the front desk, but you definitely wouldn't have found if you had just hoped that they gave you a brochure when you checked in that said, here are all the perks.
So I find that always ask those things, both the Four Seasons Lanai and the Montage had kids clubs also, which is an awesome perk, except for my understanding insurance reasons, almost every kids club needs all their children to be over five unless you stay with them. So we're not quite at that age yet.
So overall, Montage was fantastic. Service was a little lacking. I think they must either be understaffed or just, you know, not put as much of an emphasis on it. Like the service at the Four Seasons was 100% perfect. And the service at the Montage was slow at times. When it happened, it was great.
People were kind, people were awesome and helpful. But it just felt like, you know, you would be waiting for a while. If you wanted to order some lunch at the pool, it might take 20, 30 minutes for someone to stop by and another 30 or 40 minutes for your food to come.
But overall would stay there again. The three bedroom condos that exclusive had were amazing and highly recommend for families. So end of our trip, everything was great. Set my alarm for 12am, wake up and quickly go look for is that Southwest flight still available? Can I switch? I could.
So I immediately switched all four seats. We're now on a direct flight back. That $800 flight we ended up getting for 26,000 Southwest points, which is about, you know, three ish hundred dollars. So amazing savings. And then we canceled our Hawaiian flights, because Alaska lets you cancel up to honestly, up until the time of boarding.
And we got all those points back. So to whoever was flying home on Hawaiian and thought they had no chance at an upgrade, um, you know, morning of, we opened up four business class seats. So hopefully four people got really lucky that day. That said, I would have loved to fly on that Hawaiian flight direct.
The Hawaiian experience was fantastic. Everything, the flight attendants were amazing. Um, really big fan of Hawaiian, excited that they're partnering with Alaska, excited that I now have a ton of Alaska points, uh, actually transferred in the max, which was, I think either 990 or 999,000 Amex points. So I took a huge chunk of my Amex points and moved them all over to Alaska, primarily because we were booking this trip to Hawaii and we booked a trip to Europe, um, for the summer that we may end up needing to cancel, but really flexible cancellation policies.
And so many partners, we've been really able to find a lot of opportunities to use Alaska points. So honestly, if we end up keeping the summer trip, I might move some more in the rumor is that a lot of the things happening with Hawaiian and Alaska are going to be finalized after June 30th.
So my guess, and I have no inside information is that that Amex to Hawaiian transfer partner will probably end by June 30th. That said, if you want to transfer points into Alaska, I would do it now. I wouldn't wait. Um, I, I, I don't know how long it will last, but I do know that it will be gone at some point.
And I don't anticipate Alaska being a, uh, Amex transfer partner. So if you're interested in Alaska points, I would do that. A few other ways to get them are, of course you get Alaska cards. There are two Hawaiian credit cards right now with 60 to I think 75,000 point signup bonuses.
Those are probably eventually going to go away. They're issued by, uh, Barclays, but you can still get them now. So there's a way to add a few extra Alaska points. If you want, they have pretty good earning relative to the minimum spend. And if you hold a Hawaiian card, you can actually transfer points between any other person for free.
So honestly, I want one of them, either me or Amy to have just because we have a ton of Alaska points in each of our accounts. I'd love to be able to move them freely between each other. There's also an Alaska premium card coming soon. My guess is it will probably launch around the same time.
They kick off all of the finalization of these mergers. So that was our trip to Hawaii. I know that was a lot, but I think there are some tactics in there and some perspective in there and some suggestions in there for, uh, that are super valuable. And I hope you agree next.
I have a bunch of things to run through. So I'm just going to get through it. So first, um, a couple of weeks ago, there was an episode on lounges and accessing them. Two things that people sent in that I didn't mention. One, there is a card that you can't get directly called the Ritz Carlton card from Chase.
But if you do have one of the Bonvoy cards from Chase, you can change to it after a year. And the reason I brought it up now is that people reminded me that it gets free authorized users and every card holder has unlimited guests on priority pass. So that is a really cool lounge card we didn't talk about.
And then the next thing is, I hope this isn't a trend, but it looks like a few of the priority pass lounges are starting to charge a fee on top of, you know, just having the priority pass membership. I think the first one was the Virgin lounge at LAX, but I just hope that's not a trend.
So that's a quick little follow up to the lounge episode. Next, um, big shout out to Patrick, who heard me talking about VPNs and flights and wanted to put it to the test. And I've often heard that using a VPN can be helpful for international flights, but he was actually testing it domestically.
And so he was looking for a nonstop flight from Washington, DC to Houston, Texas. And he pulled up a VPN for each city, ran it once on in DC, ran it once in Texas, and actually found that a United flight was about $30 cheaper booking it in Houston, the destination city than it was booking it in DC.
Now he ran the search a few times for other cities and couldn't always replicate it. But really interesting that even sometimes domestic flights are priced differently based on where you are. So if you do have a VPN, um, I would suggest if you're about to buy a flight, at least quickly check whether that flight is cheaper, maybe open up an incognito window, check Google flights.
If it is maybe worth buying, if it's not, you know, proceed as normal. Um, on the VPN front, uh, we don't have any sponsors that are VPNs, but, uh, we did in the past have Nord VPN. It's the VPN I use for things like this. I tried to get them to be a sponsor.
Sounds like it wasn't, uh, it didn't perform as well for them as I had hoped. I still use it and pay for it myself. So if you need a suggestion, that's it. And I think there might be a deal still that works from that. I'll put it in the show notes.
So that was one thing. And then the other thing was there's an article and I'll link to it where people found that searching for award inventory on United in some areas, you actually saw more award tickets at lower prices in different countries. So if you go to the top of the site and say, I'm not in the U S speaking English, I'm in, you know, France or Vietnam speaking English, you would actually see flights that weren't available on the U S site.
I hope that's just a glitch, but maybe read the comments of the post. I'll include, but it's just goes to show that you never know what kinds of variables you tweak and you might end up finding better deals. So am I going to try that tip on United every time I search for flights?
Probably not. It's a hassle, but you could be for sure. If I'm trying to book a really big international trip, that's going to be hundreds of thousands of points. I'm definitely going to probably mess around a little bit on whatever side I'm on just to see if something else is there.
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I've got a shirt on. I've got the core shorts on. I love Viore and I love that they bring a new perspective on performance apparel. It's so versatile. It can be used for just about any activity, whether it's running, training, swimming, yoga, or even lounging or running errands or going out to dinner.
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That's V-U-O-R-I. Again, that's chrishutchins.com/viore to discover the versatility of Viore clothing. Exclusions apply. Visit the website for full terms and conditions and find the link in the description. Okay, next, Amex. Speaking of being on sites, I was on the Amex site logged in, and I was looking at the Hilton cards.
And I noticed that we'd currently downgraded our Hilton Aspire card to a Surpass card. And there was some language saying, "Hey, do you want to upgrade?" And similarly, we had another upgrade offer to go from the Amex Business Gold to the Amex Business Platinum. So one, make sure you're checking on the Amex site just to see if those offers exist when you're logged in.
If not, you can also call in and ask. But we ended up getting a bonus for both upgrades. So on the Amex Business Gold and the Amex Business Platinum, we got 120,000 Amex points after 10k spend. And that's just on an upgrade. We didn't have to open a new card.
And then on the Surpass to the Aspire, we were just doing that so that we got back to the Aspire to have diamond status on Hilton. We didn't even think there was an offer, except we did that. And we recently put some spend on that card. And all of a sudden, we ended up getting another Hilton free night certificate that was labeled as the Amex upgrade certificate.
So we didn't even know we were getting a bonus and we did. So I would say recommendation to anyone, definitely with Amex. I haven't heard of this working anywhere else. See if you're targeted for any offers. Call in to ask if you're targeted for any offers if you're looking to move cards within different programs.
So it's probably only within Bonvoy, only within Delta, only within Hilton, or within Amex's cards themselves. But definitely, if you're trying to change, see if there are any deals and they can be lucrative. A few other changes in the airline points and miles world. So one, something weird is going on with Emirates.
Citi just recently said that transfers from Citi to Emirates are going down. Instead of transferring one to one, you're going to get one to 0.8. So that's a bummer. I don't often use Emirates to book anything. If I, in fact, I've never done it, but a few days later, Chase and Amex said from the end of May to the end of June, transfers to Emirates won't even work.
So I don't think anyone knows what's going on with Emirates and their award program, but something seems to be happening. And so expect some changes, hopefully not bad, but the city change makes me think that it's probably not a good change. Um, next, uh, there's some rumors that JetBlue has announced some big partnerships coming up.
Uh, rumors seem to be that it's going to be some kind of partnership with United by the time this episode comes out. Maybe that news is there, but, uh, that seems to be something coming. And then if you use the point.me award search tool, they finally added alerts. So I love setting up point search alerts.
I currently probably use them on seats.aero and the award tool the most, um, for things like, Hey, notify me. If this Maui to, you know, the Bay area flight opens up, it didn't, but I definitely set those alerts up. So love setting up alerts. And if you're already a subscriber to point me, um, they have alerts.
The other big change in the points and miles world, we kind of knew this was coming, but a lot more details were shared about what's going on with Southwest and all the new changes coming because it's going to be a totally different experience. So starting May 28th, any new reservations, or if you have an existing reservation and you change it after May 28th, you're no longer going to have free check bags unless you're business extra.
They're also launching on that same day, the basic fair, which is effectively the want to get away fair rebranded, but you're no longer going to be able to make any changes or earn more than two X points on those fairs. So they're kind of adding their basic economy. They are not changing the cancel fees.
So even with that basic fare, you'll be able to cancel for a flight credit. But remember Southwest flight credits now will be expiring within, I think a year. So that also sucks. So a lot of the things that we all maybe loved about Southwest are disappearing. The other big changes they say are coming in Q3, but haven't.
So I think flights starting in 2026 are going to have this whole different seating layout. And so typically, if you've been on Southwest ever, you know that all the seats are kind of the same, except except exit rows. Starting next year, the first five rows in the front are going to be extra leg room, as well as three rows around the exit row.
And then everything between the extra leg room in the front and the exit row is going to be preferred seats that are really the same as the rest of the plane, just in the front of the plane. And then everything behind the exit rows are standard seats. And so you're going to have to, you know, pick those seats or pay for those seats or get them based on your fair class.
And, and so that's something that's coming. And so those, those preferred seats in the front and those extra leg room seats, it looks like are going to be about five extra inches of leg room. So kind of compared to main cabin extra or economy plus, they're going to be able to start booking flights where you're going to need those assigned seats in Q3 for flights beginning in 2026 in Q1.
A couple of the changes as far as who's going to be able to book them. Well, there are now the same four classes of service as always, except they're renaming all of them. So want to get away becomes basic want to get away plus becomes choice. Anytime becomes choice preferred and business select becomes choice extra.
And depending on which one you book affects what kind of seats you can choose. So if you choose basic, you only get standard and you don't get it till you check in. If you book choice, you get standard and you can select it a booking. If you choose choice preferred, you get a preferred seat.
And if you choose choice extra, you get the extra leg room. Um, you also don't get any checked bags unless you book that choice extra. However, there are still two other ways to get free bags and even some free seating options. Um, and that's by either having status or by being a Southwest card holder.
So if you have a list, which is their base status, you get one bag free and you can select a standard or premium seat at booking on any of the fair classes. And then 48 hours out, you can pick an extra leg room seat if it's there. And then if you're a list preferred, you get two bags and you can pick any seat regardless of what fair class you booked.
And then if you're a Southwest card holder, you get one checked bag on any fair class. But then depending on your card, you also get some seating preferences. So if you have plus or plus business, you get standard seats, 48 hours out. If you have the premier or the premier business card, you can choose standard, but you can also choose preferred seats at 48 hours out.
And then finally, if you have the most expensive, the priority or the preferred business card, you get the same perks as a list. So you can choose a standard or premium seat at booking and you get extra leg room at 48 hours out. So there's a lot of changes.
I'll put a link in the show notes to a page that details out all of them. But the short version is if you have a card or you have status, you still get a free checked bag. And if you book anything other than the basic fare they're introducing, you can still do your same day changes and standbys.
And so that's pretty nice. And you can still transfer your flight credit. So yes, you get a flight credit, but it doesn't have to be used by you. So I'll probably never be booking that basic class in the future, which is a bummer. But hopefully the kind of choice or what is now want to get away plus fares will be, you know, somewhat reasonable still.
So another pretty interesting piece of news came from Built. And if you have the Built Rewards card, which I do and I love, you can earn points for paying rent and up to $100,000 of rent a year. You earn 1x points with no fees. You can set it up with a rental portal.
You can mail a check to a landlord. So anyone that has rent, I highly recommend the Built card. It's just if you're paying that rent, you might as well be earning points. And Built points are fantastic. They have amazing transfer partners. Like I would trade my Amex points for Built points if that was an option.
But you don't actually need the Built card to use Built points program. In fact, you can join Built Rewards for free and start earning points through all the various other things they do. They partner with tons of restaurants. So there's a bunch of great restaurants in the Bay Area and I'm sure in almost every city where when you dine out at that restaurant using any credit card you have, you can end up earning any plus 2, plus 3, plus 4 Built points on top of that.
They have a bunch of partnerships with places like SoulCycle. They have a partnership with Lyft where when you get a Lyft ride, you can also earn Built points. You know, if you refer someone who opens up a Built card, you get Built points. So there are a lot of reasons to join the Built Rewards program and I think it's pretty reasonable to rack up Built points without even having the Built card.
But they've just launched another way to do it and that is paying rent not through the Built card. So as a Built Rewards member, you could have always used any credit card to pay rent, but they charge a 3% fee and they weren't awarding you any points. So it was kind of an expensive way to pay your rent.
Now, they've added earning Built points on top of whatever you get from your credit card for that same fee. So if you were to use any card that's not an Amex to pay your rent, you'll pay a 3% fee. You'll still get all the credit card points from that transaction and you'll also get 1x Built points.
Now, is this as good a deal as using the Built card? No, but if for whatever reason you don't have or want the Built card and you need to pay rent, this could be a good way to earn more points if you're willing to pay that fee. And if you think about it from the perspective of there are cards like the Capital One Venture or Venture X cards that earn 2x on everything, you're going to get an extra point from Built on paying your rent.
So you're kind of getting 3x points. You're paying a 3% fee. There are cases where that might make sense. You're effectively going to be buying points at a penny a point. Depending on the program, maybe that's worth it. Now, I'm not usually one to suggest paying a fee to use your credit card to earn points.
But in the case where you're going to not only get your points, but you're also getting another set of points. In this case, 1x points from Built. I think it can make sense in some cases. Note that if it is an Amex card, you only get half a point from Built.
So much less appealing. Now, another circumstance where paying a fee might make sense is with services for your business to turn business expenses into credit card charges. There's two companies out there, Melio and Plastique, that allow you to basically turn any of your business expenses into things you can put on a credit card.
And then they will send an ACH, send a check, send a wire, even internationally. Now, they do charge a fee. And that fee is 2.9%. But what's super interesting, obviously, if you have a signup bonus to hit, this can be helpful if you don't have the spend. But when I started thinking about the fact that those credit card fees are expenses as well, and so depending on your tax bracket, your marginal tax bracket, if your business is profitable and any dollar you're no longer taking out as profit because you have more expenses would be taxed at a pretty high rate if you took that money out instead, you can kind of tax adjust the cost of using a service like Melio or Plastique.
So depending on your tax bracket, that could bring that 2.9% fee down to a maybe more effective 1.6%, which is all of a sudden really interesting. And there are unlimited numbers of cards that earn more than 1.6%. Now, if you don't have any state income taxes or you're in a really low federal tax bracket, maybe this isn't interesting at all.
But if you're in a higher tax bracket, it could be pretty interesting. There's even another company called Zill Money that will let you put your payroll for your business on your credit card. So recently, I've been looking at this as a way to have more credit card spend on things that don't normally accept a credit card.
I don't think it is as easy to do as a consumer. I have not tested how this works for non-business things. Let's say you need to pay your contractor and your contractor doesn't accept a credit card, but you want to, this could be an option. I haven't looked into how that would work.
It's primarily targeted for businesses to use. I will try to put some links to any deals I can get. I don't know them. They're not paying me to talk about them, but I'm going to see what I can do. And I'll put links to those in the show notes if I can find anything.
Speaking of large business expenses that you might be able to turn into a credit card, there is a really lucrative business credit card deal that if you have a ton of spend, could be really valuable. But when I say a ton of spend, maybe the most I've ever seen in a signup bonus.
So the VentureX business card is offering 350,000 points in the form of 150,000 points after spending $30,000 and then an additional 200,000 points after spending $200,000 all within the first six months. Now, obviously, if you don't have $200,000 that you need to spend on a card in the next six months, you know, this is not as exciting of a bonus.
But if you run a business and you have tons of expenses that you're always putting on a credit card, it works out to an effective 3.75% back on $200,000 of spend. After that $200,000 of spend, you're getting 750,000 points, which is a pretty good return for that spend. And there aren't a lot of other cards that can match, you know, 3.75% back on that much spend.
Finally, it is last call on the Chase Sapphire Preferred 100,000 point bonus offer after spending $5,000 in three months. There is some nuance to how you're eligible for it. To be eligible, you can't currently hold a Chase Sapphire Preferred or Reserve card, and you can't have gotten a bonus on either of those cards in the last 48 months.
That said, if it's been longer than that, or you've never had the card, there are ways to make sure you're eligible. I'll link to a post that I wrote in the show notes that walks through some of that. I know it's been a great offer for a lot of you, so I just want to flag that it is kind of last call for that.
That offer will probably be gone for, I don't know how long. Sometimes they come back a year or two later, sometimes you never see them again. A couple quick last things. First, Mother's Day is this weekend. Congratulations to all you moms. You're awesome. You power the world. Shout out to my wife, Amy, and my mom, and my mother-in-law.
You guys are all amazing. I just wanted to share a couple quick gift ideas for any people who have waited this long and need a last-minute suggestion. One that we recently got in our home, which I've talked about in the past before, saying I wish I had it, is the Ratio Coffee.
It is a coffee maker that's basically like a pour-over coffee machine. It's incredible. I don't even love coffee that much, and it just makes a perfect, delicious cup of coffee. My wife uses it literally every day. It is an amazing device. It's a little on the pricey side, but it's also beautiful.
And if you compare it to the cost of actually having coffee at a coffee shop, it's probably a steal. Next is StoryWorth, which basically it sends your loved one an email throughout the year collecting stories. When did you grow up? What was your childhood like? And builds them all into a book at the end of the year.
Really cool. I've done this with my parents. It's awesome. They are a sponsor of the show, not of this episode. So I do have a discount in the show notes. Another company that we've actually used for many years is called AuraFrame. They're this great digital picture frame. We have one in every family member's house.
And you can send photos to them from your phone to all of the picture frames in your family. And it kind of is a really great UI UX for sharing photos to anyone, but in this particular case, mothers. They are also, after many years of pitching them to sponsor the podcast, have become a sponsor.
So I think we have another discount in the show notes. A couple years ago, I got my wife this really cool puzzle on Etsy where they basically took pictures of her and our kids. Really more just described height, hair color, age. And created this kind of really cool superhero best mom puzzle that she didn't really know what it was until she put it together.
So looking for cool Mother's Day puzzles on Etsy is awesome. Though I realize that by the time you hear this, that will be too late. One year, I used an app called Zeal to schedule an in-home massage for Amy. And she said it was amazing. I'll put a link in the show notes.
It's totally my referral link. But I think you get $25 off. So that's a cool last minute idea. And then finally, I asked Amy for her suggestions. And there's these 2 necklaces she loves that are initial necklaces. And I'll put some links in the show notes there. She has some with her initials.
You could do it with your kids' initials. But she really loves it. Wears it all the time. And so that's another one that I think is a good suggestion. Finally, I believe this episode is coming out on May 7th, which is the deadline for real ID to be the requirement at TSA for traveling in the US.
And so if you don't have a real ID, remember that starting today, you will need one at the airport. So if you don't have either a black or a gold star or, in California, a bear with a star in it, you probably don't have a real ID. And you may not be able to board a flight or go through security without it.
And so you can bring your passport instead. You can bring a passport card instead. Some states have enhanced driver's licenses, which are also acceptable. If you have your global entry and you've got a global entry card, you can use that. I'll link to the TSA page that says all of the different things that are eligible.
But just know that, as of today, if you don't have a real ID, you need one to go through security. This episode is brought to you by Element. Now, I love Element and I use it all the time because it helps anyone stay hydrated without the sugar and other dodgy ingredients in popular electrolyte and sports drinks.
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Get your free sample pack with any Element purchase at chrishutchins.com slash LMNT. This deal is only available through that link, so support the show and go to chrishutchins.com slash Element or click the link in the description and get hydrated. Last thing I want to mention before I wrap, I got a few messages from listeners about last week's episode on oral health with Dr.
Mark. And they really came in two flavors and I just thought the nature of my personality and this show, I thought I'd address them. So one is about guests who pitch products and the other is about fluoride and his opinions of that and fears that the show was getting a little political.
Well, on guests pitching their own product, it seems like everyone has something to sell, whether it's their book, their blog, their Instagram, their toothpaste, their ideas. So there's no escaping the fact that if I have a guest on, there's probably a thing they want to promote and that's kind of the currency in which they're willing to give up their time to come on the show.
But what I try incredibly hard to do is, first, pick guests that I want. I'm not just looking at who emails me and having them on the show. In fact, when we wanted to find someone to come on for oral health, I asked my dentist for a recommendation. I cold messaged him and I tried to get him to join.
And then two, I ask all my guests not to spend their time pitching in the episode. And if they do, I remove it. And then I give them time at the end to say, where can people find more about whatever you're talking about? And I also try to make sure you all know if me or any of my guests have some kind of interest or bias in whatever is being discussed.
So I did that for Dr. Mark last week. The funniest thing about Dr. Mark is that he didn't even mention the name of his toothpaste at all in the entire episode. And we did a retake of the outro of the last question because I was like, you've talked about it, but you didn't mention what it's called in case someone wants to find it.
So I hope you know that this show is not a platform for people to pitch and sell things. That's not the purpose of me having a guest on. I don't accept money from guests to come on. And almost every guest is because we sought them out. So I just wanted to clear that up.
Second, I wanted to talk a little bit about fluoride. I understand that for some people, this is a very controversial topic. I don't know if I knew the extent to that going into this, but I did try my best given the limited knowledge I have to kind of push back in the interview and challenge some of those opinions.
At the end of the day, from all my interactions with all of you, whether it's an email or in the real world, I know that you all are incredibly smart. And I feel like I can trust you all to do your own thinking and research if you ever hear something you might not agree with.
I also think it's healthy for all of us to hear things that challenge our own beliefs from time to time. And I get that that might mean that not everyone likes every guest or everything I say or everything a guest says. But even if you disagree with Mark on fluoride, I would be shocked if there wasn't actually something in that episode that was a valuable takeaway for you.
Also, don't assume that if I bring a guest on and they say something you disagree with, that that's necessarily my position at all. As for being political, I honestly did not think fluoride was a very politically charged topic. I could see where people who feel that way are coming from.
If you've listened to the show long enough, I think you know this show is about upgrading and optimizing your life, money, and travel. And while we all have political thoughts and opinions that might be different, I don't think they're relevant to the purpose of this show. And so I do my best to avoid politics on this show.
There are tons of places, apps, shows, social media, where you can go to have that conversation. This just is not a place where I'm trying to make it a part of the show. I hope that the episode with Mark, whether you agree or disagree with him, at least was interesting to hear and brought to light some things about oral health that I think are really valuable.
I know it was for me. That's all for this episode. If you have questions, topics, or anything you think would be good on another episode like this, I'll be doing them monthly. Please send them to podcast at allthehacks.com. Thank you so much for listening. I will see you next week.