A quick word from our sponsor today. I love helping you answer all the toughest questions about life, money, and so much more, but sometimes it's helpful to talk to other people in your situation, which actually gets harder as you build your wealth. So I want to introduce you to today's sponsor, LongAngle.

LongAngle is a community of high net worth individuals with backgrounds in everything from technology, finance, medicine, to real estate, law, manufacturing, and more. I'm a member of LongAngle. I've loved being a part of the community, and I've even had one of the founders, Tad Fallows, join me on all the hacks in episode 87 to talk about alternative investments.

Now, the majority of LongAngle members are first generation wealth, young, highly successful individuals who join the community to share knowledge and learn from each other in a confidential, unbiased setting. On top of that, members also get access to some unique private market investment opportunities. Like I said, I'm a member and I've gotten so much value from the community because you're getting advice and feedback from people in a similar situation to you on everything from your investment portfolio, to your children's education, to finding a concierge doctor.

So many of these conversations aren't happening anywhere else online. So if you have more than 2.2 million in investable assets, which is their minimum for membership, I encourage you to check out LongAngle and it's totally free to join. Just go to longangle.com to learn more. And if you choose to apply, be sure to let them know.

You heard about it here. Again, that's longangle.com. 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 find all the hacks to optimize my life.

I've been asking you all to share any questions you have so I could do a Q&A episode, and that's exactly what today will be all about. Also, I'm going to be putting a lot more time and effort into the All The Hacks newsletter in the near future. So if you want to hear about all the cool stuff I'm learning about, some new hacks I'm finding, please make sure you subscribe at allthehacks.com/email.

Okay, so by far the biggest questions were all around earning and redeeming points for maximum value. So I'll spend a lot of time there. I'll also share my top two to three cards for 2021 and how you might want to think about accumulating points with your partner. Aside from points, we'll talk about investing questions like whether to invest in alternatives like wine or art, how to think about saving for college, and automating your investments.

Finally, I'll break down the full stack of tools, services, and software I use to optimize my life, my finances, and our home. But first, I want to share a cool listener story that's also a great hack. So I've been dealing with this ant problem at home. And no matter how much of that liquid ant bait I put around the house, they just keep coming back.

So we had some termites last year and it cost hundreds of dollars for someone to be here for like 45 minutes. So I just couldn't bring myself to pay hundreds of dollars for pest control to come out because it seemed like such a racket. Anyways, I started doing some research and I found this product called Pesty.

They offer a DIY version of the same pest control the pros use for under $50. They even ask for your zip code so that you're getting a formula for the pest in your region. So last month, I tried it out. You walk around your house, you spray for about five minutes, and since then, no ants.

So I thought it was cool and I reached out to the company and small world, one of the founders who replied was a guy named Dylan, who actually had already emailed me. He's an All The Hacks listener who emailed me in June after listening to episode one. So I told him how much I loved his product.

He said that he loved the show and I told him I wanted to mention it. And he said, if anyone on the show is a listener and wants 10% off, he set up a promo code. So you can go to AllTheHacks.com/Pesty and get 10% off. So thanks to our listener, Dylan, for setting that up.

All right, so let's jump in. But of course, I still always have to remind you, I do work at Wealthfront. All the opinions I'll express are solely my own. They do not reflect the opinion of Wealthfront. This podcast is for informational purposes only and should not be relied on for investment decisions.

All right, so with that out of the way, let's jump in and start with a great question. Ross emailed me and asked, if you had to pick the two or three cards to have in 2021, what would they be? Amex Gold and Sapphire Reserve, that was his guess. And I'll say, you got it half right.

I do think the Chase Sapphire Reserve is the best single card. It's the card I carry with me all the time. And I think for most people, travel and dining is a bulk of their spending and getting three points per dollar on that is fantastic. Now, if you want to save a little bit on the annual fee and just get two points per dollar on travel, but now you still get three on dining, you can go for the Chase Sapphire Preferred.

The only thing I'll point out is that the Reserve comes with a $300 annual fee credit. So even though you're paying a pretty high annual fee, you get $300 back off any travel purchased on the card. You don't have to use a portal or anything like that. The other real big benefit of the Reserve is that every Chase Ultimate Reward Point is worth 1.5 cents if you want to redeem it in the portal.

And that's across any Chase card you have that earns points. So I actually think the best second card for most people, if they have the Chase Reserve or Preferred, is the Freedom Unlimited. And the reason I think that is because it's an everyday card. It's one and a half points per dollar on everything.

So I think a great one-two combo is Reserve for travel and dining, Unlimited for everything else. And then all those points can take advantage of the fact that the Reserve gives you points value of one and a half cents if you redeem in the portal or if you want to transfer it to other airlines, which I'll get to in a little bit.

You could do that with all those points as well. So that's my favorite kind of one-two combo. If you're in the Amex ecosystem, I do think the Gold card is a great card. You're getting 4x on restaurants and 4x on groceries, but there's not a great earning on flights, which is something that I spend a bunch of money on.

So I think to make the Amex combo work really well, you need the Gold and the Platinum, and that's just a lot of annual fees, unless you're really able to take advantage of the perks that the Platinum card has. That said, if you do spend a lot on flights, five points per dollar on flights is really unheard of.

And every now and then I've planned a group trip and I've been responsible for booking like 10, 15 flights all at once. And the number of points you can earn on a Platinum card is so huge. So I do think for that reason, if you find yourself spending a lot on flights, it could make sense.

I also think Amex, while they have way more transfer partners, as you're getting into points, I think if you're not ready to jump all the way into finding the airline to transfer the points to, it's nice that the portal on Chase gives you one and a half cents, whereas on Amex, it's only one cent per point.

So I think for most people, Sapphire Reserve combo with the Unlimited is a great two cards to have. If I were going to add a third card, instead of trying to go for another ecosystem, I would really look at whether there's a place you spend a lot of money or have a lot of loyalty to.

That could be an airline that you fly all the time. That could be a hotel that you stay at a lot. That could be Amazon. I know for me and my wife, we spent a lot on Amazon, both for Amazon Fresh delivery at Whole Foods and just buying stuff on Amazon.

So I would say the Sapphire Reserve, the Freedom Unlimited and the Amazon Prime Visa are like our three core cards. And yes, we have a Bonvoy card for when we stay at Marriott and we have other cards, but those are the three that I really use a lot. Okay, so that's my favorite one, two, maybe three card combo.

But Danielle and Dennis sent a question asking about whether signup bonuses are really the place to accumulate points. And I'll say, I do spend a lot of time talking about the cards that I use day to day to maximize the points I'm earning on my spending. But if you ask me how I got a big portion of the points I have, it's all from signup bonuses.

I've almost never signed up for a new card without a massive bonus. And sometimes when I see a huge bonus, that's really the time to strike. I do keep track of my credit score. And I think the most important thing to think about with these signup bonuses is you have to hit the minimum spend.

One time I think I signed up for a card and this was a poor lesson to learn, but I didn't hit the minimum spend in time and I only got half the signup bonus. So I would keep track of that. I would keep track of your credit score. I would keep track of rules.

Chase has one where you can only open five cards in a 24 month period. So you'll know that you'll just get declined if that happens. And as you do this a lot, you'll find out that different credit companies, Chase is another good example, will only extend a certain amount of credit.

So if you sign up for a fifth Chase card, you might get this message that says we're reviewing your application. Now, the good news is you can call the reconsideration line. There's a number, just Google Chase or Amex reconsideration line and talk to them. Oftentimes they'll let you say drop some of the credit on one card, transfer it to another card.

So I think there's a lot of options there. I would say the subreddit churning, that's r/churning, is a great place to go look up all of this information. There's so much stuff there. But right now, 2021, when I record this in September, there are some massive signup bonuses. So I just want to run through a few of them because it's really unusual to have so many.

So on the Chase side, the Chase Sapphire Preferred card, even though I wouldn't use it right now because I have the Chase Sapphire Reserve, it's a 100,000 point signup bonus. So if you figure you're getting, even on the Reserve, three points for travel and dining, you'd have to spend $33,000 on travel or dining to earn 100,000 points.

So these signup bonuses can have a huge impact on how many points you have. The Reserve, although not as big, is at 60,000. There's two United cards, the Explorer at 70,000 and the Quest at 100,000. These are some really big bonuses from Chase. On the Citi side, there's a card I've never had and I've always kind of thought about, but for me, I didn't necessarily want to add yet another place to collect points is the Citi Premier card.

It's 3x points on gas, groceries, restaurants, and travel, and they have a huge 80,000 point signup bonus right now. Amex has a bunch as well. The Platinum card, depending on where you sign up, could be 100 to 125,000 points. The Gold card is 75,000 points. The Delta cards range from 75 to 125,000 points, and the Hilton cards range from 150 to 200,000 points.

There's just so many huge bonuses right now. So I will say, if any of those sound like places you want to accumulate points, signing up for a new card can be a great way to get points. And I definitely look into it, assuming you can meet the minimum spend and assuming that that minimum spend is spend you already need.

Don't go spend money that you don't need to spend just to meet the bonus. It kind of reminds me of going into debt and paying interest. It's never worth it to get those extra points. But if you already spend enough to meet these minimum spends, the signup bonuses can be huge, and they're the reason I've taken so many free trips.

Finally, if you do decide you want to sign up for any of these cards, I put together a page with all my card recommendations, as well as the top signup bonuses right now, including some big ones for business cards. And I'd really appreciate it if you use those links.

You can find them in the show notes on your podcast app or at allthehacks.com/cards. As you know, I don't have sponsors on the show right now, but I will earn a little bit from those links. So if you find a better bonus somewhere else, by all means, go wherever the best bonus is.

My number one priority is you get the most points and take the most free vacations. But if it's all the same and you want to get a new card, I'd love it if you use those links. It seems like with every business you get to a certain size and the cracks start to emerge.

Things that you used to do in a day are taking a week and you have too many manual processes and there's no one source of truth. If this is you, you should know these three numbers. 37,025, 1. 37,000. That's the number of businesses which have upgraded to NetSuite by Oracle, and I'm excited to partner with them for this episode.

NetSuite is the number one cloud financial system streamlining accounting, financial management, inventory, HR, and more. 25, NetSuite turns 25 this year. That's 25 years of helping businesses do more with less, close their books in days, not weeks, and drive down costs. And one, because your business is one of a kind.

So you get a customized solution for all your KPIs in one efficient system with one source of truth. Manage risk, get reliable forecasts and improve margins. Everything you need to grow all in one place, which I can tell you from all the companies I've run, makes everything so much better.

So right now, download NetSuite's popular KPI checklist, designed to give you consistently excellent performance, absolutely free at allthehacks.com/netsuite. That's allthehacks.com/netsuite to get your own KPI checklist. Allthehacks.com/netsuite, N-E-T-S-U-I-T-E. You all know I love credit card points, so I'm excited to be partnering with Card Pointers today, which is one of my favorite tools for travel hacking.

It's a free app that helps you manage all of your credit cards in one place and makes it easy to find the right card to maximize your category bonuses on every purchase. You can also load it on your partner's phone, so they always know the best cards to use.

The app automatically tracks every category bonus and recurring credit from over 5,000 cards, and they also track and help you use your Amex, Chase, Bank of America, or Citibank offers to save even more money every day. And with their browser extension, you can actually activate every single Amex and Chase offer in just one click.

And because of that massive credit card database, you can do all of this without having to give up any personal or banking details. The app is free to download, and many of the features are free as well, so you can download them as well. But if you want to try out the pro version, there's a free trial.

And if you decide you want to sign up after the trial, which you probably will, you can go to allthehacks.com/cardpointers to get 20% off. Again, that's allthehacks.com/cardpointers. Another question from Christopher, which is actually kind of in the same vein, was about how to optimize points for wedding expenses. It's true of a home renovation as well, or any time you have to spend a lot of money, but that money's not really in a category that often earns really, really high bonuses like travel or dining or gas or groceries.

And so I think there's really two things to consider. One is if you want to get some of these big signup bonuses for new cards, a great time to do it is when you already have a lot of spending coming up. Some of these big bonuses come with $5,000, $10,000 of spend.

And if you have a business card, sometimes it's even higher, but the bonuses can be higher as well. And so I think that that's a time where you say, look, I've got a lot of money to spend on my wedding. I've already budgeted for all this spending. That could be a perfect opportunity for you to sign up for a new card and be able to meet that minimum spend and get that huge signup bonus.

But one thing that happened when we were getting married is I realized that, yes, I could get a couple points per dollar paying for a lot of these things on my credit card, or maybe it was only one and a half because I was probably using the Freedom Unlimited.

I actually offered to pay cash to a lot of vendors and asked them if there was a better deal. And some vendors gave anywhere from 5% to 10% off. And in that case, it was just a way better deal for me to use cash than it was to earn one or two points per dollar because 5% to 10% off is like an instant no-brainer.

And so I would say negotiate for a cash deal. And if you can't get it, and by the way, if you don't have to pay a fee to pay by credit card, then I would consider signing up for a card and using these expenses to meet the minimum spend to get a huge bonus.

Or maybe, you know, depending on how expensive your wedding is, two or three huge bonuses. Okay. And if you're getting married, then you're probably already starting to think about how you might want to optimize points as a couple with your partner. And this was the second most popular question.

Charlie, Brendan, Daniel all sent in asking about this. And the big piece of it was, are you using separate cards or are you using authorized users or how do you do this with your partner? And so I'll say for all but one card, we just are authorized users on each other's cards when it makes sense and when it's free.

So my wife happens to be the Freedom Unlimited cardholder. So I'm an authorized user there. I have my Chase Freedom card. She's an authorized user there. I've got a Bonvoy card. She's an authorized user and so on and so on. The one exception to that rule is that we each have a Chase Sapphire Reserve card.

And while to some people that might not make any sense, for us, it's the card we use the most, so we both want one and we wanted to have one card where the other person wouldn't log in and see the transactions each month. So if we wanted to buy gifts for each other, we could kind of keep it a secret.

And if you take the annual fee and you subtract off all the travel credits, the Peloton credit, the DoorDash credit, and you consider the fact that if one of us were an authorized user on another person's card, they do charge $75. For us, it ends up being worth spending a little bit extra to have two cards so that we each have at least one credit card that's totally our own, that we can put something on that the other person doesn't see.

It's often gifts. It's often around the holidays, but that's the one exception to that rule. One thing that was a follow-up question someone asked that I think is really important is if you make someone an authorized user on your card, let's say you've had the Chase Sapphire Preferred for a while and your partner has been on that card, that does not preclude them from getting a sign-up bonus.

So right now, they could very easily go sign up for the Sapphire Preferred and get that 100,000-point sign-up bonus right away. I think that it's very important to consider that because I think one of the ways we've accumulated so many points is that I played the whole points game for a few years, and I was kind of bummed out because there weren't dozens of new cards each year.

And then I talked to my wife. I said, "Hey, what if we do this on your side?" So then we just started opening up a lot of these same cards on her side, and we were just doubling up the bonuses. So we've both had a Sapphire Preferred. We've both had a Sapphire Reserve.

We've both had an Amex Platinum. I think we've both had an Amex Gold, and that has allowed us to accumulate a lot of points. And funny enough, we have most of those cards today. We might not have two of them, but we've kept a lot of them, and we've been continuing to rack up points ever since.

When it comes to the authorized user thing, I will say, consider what the purpose of the card is and whether it even matters. For us, the Amex Platinum is a great example where almost all of the spending goes on that card for flights. And we don't buy flights in person, so we don't really need our own Amex Platinum.

Another perk of that card is that you get access to the Centurion Lounge at a lot of airports, but we don't travel independently enough to make it matter because you get a guest for free. So we don't need to both have a Platinum card for that lounge. So again, think about whether it even makes sense to get an authorized user if that's a card you use exclusively online.

We store all of our credit cards in one password. We have a joint one-password account. I'll talk a bit more about one-password at the end of this, but I can't say more about how much it's been helpful to be able to have all of our logins for all of our mileage accounts, all of our credit card numbers in one place where we can both access it.

And because we have all these cards, we have points in a lot of places. So we do keep a spreadsheet to track all of it. That includes where they are, whose they are, when they expire. And while nobody asked this, I will point out that miles do expire with some programs.

And if you want to make sure they don't expire, there's a few things you can do to keep them around. If you have a flight or a hotel coming up, that's an easy one. If you have that credit card, you can just spend money on it. But let's say you happen to have a random old airline or hotel account where you don't have a credit card and there's nothing going in.

You could always just transfer some points there. So if they're a Chase or an Amex partner, you could move some points over. You could make a small redemption. I don't know if this is as common anymore, but you used to be able to spend like 100, 200 points to get a magazine subscription.

You could always just buy $10 or $20 worth of points to top up the balance. Anytime that points balance changes, that almost always qualifies to extend the deadline. A few others are most rental car companies like Hertz or Avis will let you credit that rental to almost any airline.

So you could do that. Or almost any airline and hotel has a shopping portal. And if you click through their portal, it's kind of like Ebates and Rakuten where you can make a purchase online and earn a few more points. So that's what we do to make sure that all these points that are all over the place never expire.

But yeah, that's our strategy as a couple. So David wrote in asking, "Is it even worth dealing with points and miles if you only fly once or twice a year?" And I'll say it really depends on where you travel and what class you want to travel in and what kind of hotel you want to stay at when you get there.

So I think points really come in to be valuable when you're staying in really luxurious hotels or when you're flying business class, when you're flying international or maybe even if you're flying domestic, but to obscure airports where there might only be a couple of flights a week. So if none of those things apply or if the amount you spend on travel each year is only a few hundred dollars, then honestly, you might be better off just using the Citi Double Cash Card and getting 2% cash back and just using that cash to buy flights.

OK, so one of the hacks that I talked about before is that if you have a credit card that gives you a lot of points per dollar on grocery store purchases, you can actually buy gift cards at the grocery store to spend elsewhere. And so David wrote in and asked, "Is there any downside to buying gift cards at the grocery store and specifically buying prepaid Visa gift cards?" I'd say there are two reasons this might not be as good as it sounds.

On the prepaid Visa card or Amex card, anything where it's not actually a specific retailer gift card, one of the reasons I don't like them is that you usually have to pay a fee. So if you get a $100 gift card and you got to pay a $4 activation fee, you might be getting a lot of points per dollar, but you're paying a 4% fee and chances are that doesn't make up for it.

So I typically won't use a credit card to earn points to buy a gift card if I have to pay a fee to get that gift card. The other challenge with these prepaid cards is that it's sometimes tricky to get the balance down to zero. And if you ultimately have a $100 card and you only spend it down to $4, that's just like having a 4% fee on the card.

And I don't love that. And one of the reasons it's tricky to get the balance to zero is there's not that many retailers that will let you split purchases on multiple cards. However, a restaurant is a great place to do this. And there's one hack that I've learned along the way.

If you tell someone to put $100 on a card at a restaurant, but it's a prepaid card that only has a $100 balance, it often won't go through because the restaurant might preauthorize an amount greater than you tell them to leave room for the tip. So what you can do is you can say for a $100 gift card, can you put $80 on this card and then tip $20 to get it to the full $100?

When it comes to buying retailer gift cards, if it's already a retailer that I have a purchase in mind, let's say I need to spend a lot of money on something at Home Depot, or I don't have a travel card and I want to buy some flights on Southwest, I think these are great opportunities to get a lot of points, assuming you earn a lot of points at the grocery store.

But the one caveat I'll give is that Visa, MasterCard, Amex all offer some amount of purchase protection with their cards. And I've used this purchase protection for a few different things. But oftentimes, if you buy something and it breaks or you lose it within the first 90 days, they'll refund you up to a certain amount.

And so a great example was I bought an SD card and I immediately lost it a week later and I was able to get that completely refunded. Warranty extension is another one. And so sometimes if you buy something, it has a one year warranty. The credit card company will actually give you an extra year warranty.

So if you buy an iPhone and it breaks in the second year, Visa or Amex might actually cover the cost of repair that second year, even though Apple won't. But when you buy gift cards, if the purchase wasn't on the original credit card, then you don't get a lot of those benefits.

So if I'm buying something on Amazon or anywhere and that purchase is of something that I think could break or might be easily lost or that I might need to repair, those are purchases that I often won't make with gift cards. OK, and now for the big question that Steven, Brendan, Ryan, Michael all wrote in asking about, how do you redeem miles to get the maximum value?

So as much as I love the fact that the Chase and Amex travel portals make it really easy to use your miles, use your points to book travel, the way you get the really, really big values for your points is when you can book directly with airlines and hotels.

And to do that, you either earn points in those programs or you take Chase points or Amex points and you transfer them to those airline or hotel partners. And don't forget, you're not limited to flying on just the transfer partners. You can use miles with those partners to fly on their partner airlines.

So you could transfer Chase points to United and fly on any of the 26 different Star Alliance airlines like Lufthansa or Asiana or A&A, and you could transfer miles to British Airways and fly on any One World partner like Japan Airlines or Qantas. And you could transfer Amex points to Delta and fly on Korean Air or Alitalia.

And that's how you get really, really outsized value from your miles. And like I mentioned earlier, the biggest outsized value usually comes from flying business class, flying to obscure destinations, flying international, staying at luxury hotels or doing all. If you're trying to take a long flight to an obscure destination in business class, that can sometimes get you 10 cents per point or mile, which is really, really crazy compared to what it would cost otherwise in cash.

A great example of this is a flight that my neighbor Joe recently booked. So he was looking to take his family of four to Europe and was trying to do it in business class, was sitting on a lot of miles and managed to find that if he transferred 440,000 miles from Chase to Air France, he was able to book four round trip business class tickets to Europe.

Now, those tickets would normally cost somewhere on the order of four or $5,000 each, but if he had used 440,000 miles in the travel portal on Chase, he would have gotten one and a half cents per mile and he would have been able to book $6,600 worth of flights, which wouldn't have even gotten him two tickets.

So he got crazy value. So the question isn't really, how do you get the crazy value? It's clear that it's from luxury travel, luxury hotels, international trips. The real challenge is how do you find the availability? And I'll give you three ways to do it. There's a DIY approach, there's a premium paid search approach, and then there's paid award booking services that will do it all for you.

So you could do all this for free with a DIY approach, which basically involves going to the websites of all the airline partners and searching for the flights you want yourself. So Chase has, you know, 10 different airline partners. You could go to the United website and search for flights.

You could then go to the Flying Blue website or the British Airways site. And the downside is that it's a lot of searching and the more flexible you are with dates, the more searching you have to do. And depending on the airline, you might actually have to go in and create a mileage account with each airline you're searching, but it's a hundred percent free and it totally works and in general, I always say it's a great starting point.

If you have a bunch of Chase points, maybe just go to United's website and see if you find the flight. If you have a bunch of Amex points, maybe it's Air Canada, maybe it's Delta and just search the sites just to get a quick glance, but if you don't see what you want at the very beginning, you might want to consider paid sites because they make the searching a lot easier.

So I used to always recommend JuicyMiles.com because it was easy and fantastic, but it seems as of a few weeks ago, they're transitioning to a new brand, which is Point.me and while it does appear that they finally put the search on their site, I think it's still a little broken.

So maybe by the time you're listening to this, it's working. I really hope it does because it's a fantastic product when it was working, but right now it's really hard to recommend because it doesn't work. Another paid search site is ExpertFlyer. It doesn't support every airline, but they do let you search plus or minus three days so you can search a little bit more and so you can go in and search by airline.

Or I think one of the best products with a couple caveats is KVS Availability Tool. Now you need a PC and you need to be comfortable using an interface that looks like it was made 10 or 20 years ago, but they support more airlines than anyone else and if you do have a Mac, you can use it with an emulator like VirtualBox, but it definitely has a learning curve.

So I wouldn't recommend it if you don't want to go deep down the rabbit hole. And I really hope for your sake that the Juicy Miles to Point.me transition is made by the time you need it because it's just such an easier product to use. One thing to keep in mind with any of these searches, whether you're doing it manually on the airline websites or using a tool, is that you're only going to find availability when it exists for your entire trip.

So I'd say it's worth looking for flights to major cities and buying a paid ticket for a short flight at the end. So for example, we recently tried to go to Santorini in Greece and there was basically no availability, but we looked for flights round trip to Athens and got them in business class with points and then we just bought a $50 30 minute flight to get to the island.

So if you're flying to Thailand on an island, maybe you just search for flights to Bangkok or Kuala Lumpur or Singapore instead, or if you're going somewhere in Europe, maybe search for London, Paris, or Frankfurt if you don't find your original destination right away. This is also true for departing cities.

So I live right near SFO and while my preference is always to fly directly from here, one time we wanted to go to Tokyo and there just wasn't anything. So we took two business class flights from LA and we just bought a cheap $75 ticket to LA and flew direct from there in an amazing lie-flat business seat on ANA, which by the way is fantastic.

Finally, if all of this sounds like a lot of work, but you're sitting on lots of points and want to take an epic trip, there are award booking services, which are basically like paying someone like me, but better, who has access to all these tools and knows the ins and outs of everything, promotions, what's going on right now, who's got the right availability, and they will go and find all of your travel for you, depending on which site you use, they can cost anywhere from $100 to $200 a person.

Some of them just charge a fee to get started and if they don't find you anything, they don't actually end up charging you. I know that Juicy Miles ran a service like this and now Point.me has their full service concierge. I've heard great things about it, so check that out.

Or if you just search award booking service online, you'll find dozens of companies that do this. Hey everybody, I just want to interrupt because I've partnered with Point.me, my favorite award search tool, to give you a special offer of only $1 for your first month of their standard plan, if you go to allthehacks.com/pointme and use the promo code HACKS.

Again, allthehacks.com/P-O-I-N-T-M-E, or find the link in the show notes. So definitely take advantage of that if you're planning a trip with Points. So that's all flights. We didn't talk at all about hotels and that's because they're a little easier. If you already have hotel points with a specific program, then great.

Just search on their website and there really isn't much more to do. And while Chase and Amex each have hotel partners, other than transferring Chase points to Hyatt, I don't think you should waste your time. That said, I think some of the best points redemptions I've ever had are booking through Hyatt.

For Christmas in 2019, we stayed at the Park Hyatt Kyoto. It was a 30,000 points a night, which probably would have gotten me four or $500 booking through the portal, but that room was almost $1,300. So it was a fantastic redemption. If you do really want to take epic trips to hotels and for whatever reason, Chase Points or Hyatt is not interesting, the way you're going to want to do it is to get a credit card with a hotel chain.

And the reason why is that so many of the transferable points, Chase, City, Amex, they transfer one-to-one, but for almost all hotel chains, except Hyatt, the value of hotel points is about half to a third the value of airline points. So you're just always going to get a better deal transferring your Chase or Amex points to airlines.

That said, credit cards for hotel companies have much higher earnings. So if you want to earn hotel points, you're better off getting a hotel card that earns five, six, maybe even seven points per dollar on different categories and really helps you rack up points on a hotel program like Marriott's Bonvoy or Hilton Honors.

Okay. I know that was a lot, but so many of you asked that question. So hopefully that was helpful. If I missed anything, please reach out. I'm happy to help clarify. I probably should just write a big guide to this and I probably will at some point, but for now, I hope that helps.

So there's still a bunch of other questions people wrote in. I'm going to start next with investing because we got a lot of questions there. There is nothing I love more than learning that something I enjoy is actually so good for you. And nothing showcases that better than Pu-Erh tea.

It has so many health benefits and I think one of the best and easiest ways to consume it is from our sponsor today, Peak Tea. Peak's Pu-Erh teas are all cold extracted using only wild harvested leaves from 250 year old tea trees, rich in minerals, theraflavins, and catechins. Then everything is triple toxin screened for pesticides, heavy minerals, and toxic mold commonly found in plants.

And Peak's products are so easy and zero prep because they're all in pre-measured quantities that dissolve in cold or hot water in seconds and are so travel friendly. They have so many products, but lately I've been alternating between the green Pu-Erh for mental clarity and energy and the black Pu-Erh, which helps kickstart digestion and metabolism with a rich earthy flavor that is so good and probably one of my favorite things to drink, and if you need another reason, search for all the amazing research backed benefits of polyphenols for your gut microbiome, heart, blood sugar, and more, and then be happy that Pu-Erh is more concentrated in polyphenols than all other teas in the world.

But you don't even have to take my word or do any research because Peak offers free US shipping, free returns, and a money-backed guarantee. And for a limited time, you can get up to 15% off and a free Quiver with 12 tea samples at my link at allthehacks.com/peak, that's P-I-Q-U-E.

So check them out today at allthehacks.com/peak, P-I-Q-U-E. Sometimes the smallest changes make the biggest impact and Trade Coffee is a great addition to your new year routine, and I am so excited to be partnering with them today. Trade is a subscription service we've been using for over a year that sources the best coffee across the country and brings it straight to your doorstep.

They've built relationships with over 50 local roasters so you can enjoy their craft from the comfort of your own home at a fraction of the cost of going out for coffee. There's multiple ways to experience coffee with Trade, sign up for a subscription, or try one of their starter packs today.

It's been so convenient for us to have coffee just show up exactly when we need it, and over the past year, we've gotten so many great coffees from Trade, but this last bag of beans from Drink Coffee Do Stuff in Tahoe, it's called Bark the Moon, and it's so delicious.

So jumpstart this year by signing up for a Trade subscription. Right now, Trade is offering a free bag with select subscription plans when you visit allthehacks.com/trade. That's allthehacks.com/trade for a free bag with select subscription plans. allthehacks.com/trade. Before we get back to the episode, I just want to thank you for listening to and supporting the show.

Your support of our advertisers is what keeps this show going. To learn more about all our partners and get links to all their deals, you can go to allthehacks.com/deals where the URLs, codes, and discounts are all right there. So please consider supporting those who support us. So Josh wrote in and asked what type of setup I have for my 529, and Swarupa wrote in asking about investments and planning for kids coming into the world.

So I'll just share a little bit about what I do. So I set up a 529 at Wealthfront, and at first glance, I thought, even as an employee, do I really want to pay a fee for my 529 given that tax benefits of the automation aren't as relevant when you have tax-free gains like you do in a 529?

Ultimately, I did some research and I came to the conclusion that most 529s that you sign up for online don't have as much opportunity for diversification as Wealthfront offered. And so for me, the extra risk-adjusted return I thought I would get from that diversification made up for the fee.

And so that's what I went ahead and did. Now, last week, I talked to Andy Ratcliffe, and he brought up a really important point about liquidity. I would say one thing to consider is that when you put money in a 529, that money needs to be used for educational expenses.

Now, the good news is it doesn't just have to be college. It could be for private school. And if you don't end up needing it for your children, you could pass it on to their children, and there are even some circumstances where you might be able to withdraw it if your children get scholarships.

But I will say you can't use it to buy a home. You can't use it to pay for medical expenses. So do make sure you have enough liquidity outside of a 529 to be able to cover things like that that might come up. And realize that the value of not having to borrow or pay fees if you do need that money is probably going to be greater than the tax advantage you'll get from a 529.

So as for trying to predict how much you need to contribute, there are lots of tools online, we've built one at Wealthfront where you can go in and pick whether it's a state school or a private school and kind of get a sense of what that's expected to cost and how much you need to contribute and then just start making contributions.

One other financial thing when it comes to planning for kids is making sure you have the right insurance plan. So when you're young and healthy, it might have made a lot of sense to get a high deductible health plan with an HSA and contribute each year because you weren't going to the doctor that often.

But it turns out if you haven't looked up, having a baby is quite expensive. And if you're using a high deductible health plan, it's very likely that you will go through that entire deductible and it will probably not have been your best choice that year if you had access to a PPO or an EPO.

One of my favorite plans, assuming all of the doctors and facilities you want to use are in-network, is an EPO. Usually it's the cheapest cost for you if you're in-network, but the downside is you can't go out of network. I was fortunate that the EPO my company offered had all the facilities we wanted it to go to in-network, and so I signed up for that and my wife had an EPO through her plan, and the entire cost of pregnancy and childbirth was less than $500.

Another question that I get a lot, and specifically this time from Josh, is how do you think about allocating to alternative strategies? This could include things like crypto, wine, art, angel investing, etc. The way I think about it in general is that I keep a small amount of my portfolio on things that are exciting, things that are fun, things that I think I might have an edge on, but at the end of the day, I keep the vast majority, 90 plus percent, in a long-term, diverse, passive investment strategy.

And so as my net worth has grown, that kind of small less than 10% piece has gotten big enough that I've been able to do some extra things. So some of that was buying some Bitcoin. I've invested in a few companies I was really interested in, and I've made a few other small investments in projects I was excited by, but at the end of the day, I haven't actually really purchased a lot of alternatives.

I haven't gone and purchased any fractional art or any wine other than the wine I buy to drink, but if you want to dive a little deeper, definitely check out the episode I did with Andy Ratcliffe, or keep an eye out for an upcoming episode of the Modern Finance Podcast, where I talk about how much to consider allocating in your portfolio to cryptocurrency.

Finally, Jeremiah asked me, "How can I send money into an account and automatically invest it?" Now, this is a fantastic question because it's just something that seems so broken. There are so few brokerage firms that will allow you to do any kind of recurring purchases, and almost none that will let you do it with a portfolio.

Instead, you're forced to deposit money and set up a trade every time you want to make an individual investment. So, I might sound like a broken record, but I use WealthRent for this. In fact, when I joined, I spent the first 18 months working on building automated investing so that you could say, "I want to deposit money, and I want it to automatically go here and do this," which could mean keep a certain amount in cash, then transfer $200 a month into my IRA, and then invest the rest in a portfolio that looks like this.

And you can customize that portfolio to whatever types of investments you want. I do think there are probably a few other brokerage firms that allow this. I know that Vanguard allows you to set up direct deposit, but you still have to set up the individual trades. I also believe that Robinhood lets you make recurring purchases, but you have to set it up for each individual security or index fund.

So, I really think this is one of the things that RoboAdvisors and WealthRent specifically have put together to make this really easy. So, if that's interesting, definitely check it out. And last episode, Andy shared that if you go to wealthrent.com/andy, you can get your first $5,000 managed for free.

All right, that's it with investing. I want to jump into the different tools and services I use to optimize everything I do. And Josh wrote in specifically asking about financial and investment tools, so I'll start there. When it comes to tracking my points, my budget, spending, net worth, there's really three tools I use.

I track all my points, and I create a budget in Google Sheets. It's as simple as that. I do use Mint to sync all of my transactions from all of my credit cards so I can try to get a good sense of how much I'm spending each month. I don't love Mint, but it's free.

Although I have heard really fantastic things about Copilot, Jesse from YNAB really lured me in that direction. And Tiller is a really cool product that lets you sync data into Google Sheets. But at the end of the day, I think Mint being free works for this very specific purpose well, and I'll be honest, I oftentimes just export all the data out of Mint and just bring it right into another spreadsheet.

And then finally, I use Wealthfront for tracking my net worth. I sync all of my accounts there, and I can just see how it's going. I can use that for planning for the future. I go in and say, "This is how much I'm going to save each month," and I can project my net worth, slide around my retirement age, and all that.

When it comes to insurance, I am not loyal to any particular insurance company. In fact, we use Geico for car, we use Lemonade for our home, we use Travelers for my wife's engagement ring. So honestly, every year or so, I just go on, I do some quick searching on different providers to see if one is cheaper, and I'm happy to switch at any point in time.

Taxes, up until a few years ago, I used TurboTax for everything. And then it just got to a point in life where the different types of investments, the different businesses, everything was just enough that I was done doing it myself. And I used a firm called Anderson. It's not cheap.

But if you are in a situation where your taxes are complicated enough that you want to spend a few thousand dollars a year at minimum, definitely encourage you to check them out or email me, and I'm happy to make an introduction. Once we had a child, we really started to think about estate planning, trusts, wills.

One hack here is that some big employers offer a legal benefit where you can pay a small amount of money each month, and it gives you access to free legal services. So our first estate plan and will and trust and health care directives and all that good stuff, we set up with a lawyer through the legal program that Google had.

Recently, after having a child, we decided to update everything. And I went ahead and set everything up with Trust & Will. I got a chance to meet the founders of Trust & Will. I thought they were fantastic. I'm not an investor. I'm not an advisor. I'm not a shareholder.

But I just think the product's great. And if you want to get 15% off, I emailed the founder, Cody. He set me up with a promo code, allthehacks.com/trustandwill, and you'll get 15% off when you sign up. And I'll put a link to that in the show notes. Finally, when it comes to brokerage, it's probably no surprise that almost all of my investments are at Wealthfront.

So I use that for my taxable brokerage, my 529, my Roth IRA. I have 401(k)s wherever they are. Wealthfront happens to be at Vanguard. And if I do trade any individual stocks, I do that at Interactive Brokers. I would not recommend Interactive Brokers to most people. I would much prefer or recommend something like Schwab or Vanguard.

But the reason I love Interactive Brokers is that they do offer the ability to borrow against your stock positions for, right now, I think it's 0.75%. So there have been a couple of times where I've wanted to do that. And that rate makes it worth the fact that they have one of the worst user interfaces I've seen in my entire life.

Finally, one other one, HSAs. I do have an HSA from a few years ago. And one thing I didn't realize until recently is that you can actually transfer your HSA to a new provider. And many of the HSAs that I've seen or that I've personally had through my employer are terrible and ridden with so many fees.

I love this startup called Lively. I transferred my HSA there. They set you up with a Fidelity account. You can invest your HSA however you want. And again, I have no affiliation with this company other than I think they have a fantastic product. So I moved my HSA over to Lively.

I think that covers all of the kind of investing and financial things. But I got an email from John asking how I use an app called Alfred. And instead of diving into that right away, I thought I'd just give a high-level overview of the types of apps and software I use to make everything more efficient.

So the biggest thing that I think I couldn't live without is Gmail keyboard shortcuts. If you haven't turned those on, I don't even know how I would operate without being able to fly through my inbox without shortcuts. They aren't the most intuitive shortcuts, but I promise that as soon as you figure it out, it'll make email so much faster.

For storing stuff, I just use Google Drive and Dropbox. For some reason, I have both of them. I'm not really sure. I've decided to use one of them for kind of podcasts and all that stuff and Google Drive for everything else. On my Mac, I use an app called Alfred, and it's probably the most important app I have.

It replaces the spotlight search when you press command spacebar. I use that to find any file on my computer. I use that to look for contact information. I use it for snippets where I can create a shortcut for longer pieces of text like a known traveler number or an address.

And I can just type in a couple of letters and automatically expand that to what I want. I actually use that for emojis so I can spell out an emoji like S space. Thumbs up will immediately give the thumbs up emoji so I can use those faster. I use it to do calculations.

It actually stores your clipboard so I can search things that I've copied and pasted days or even weeks ago. And then finally, I use it for custom web search. So things like Google Drive, I have it set up so I can really quickly just type in, you know, like S G and then just search Google Drive straight from there.

It'll pull up a website and search Google Drive. So Alfred is a fantastic product. I gladly pay for it myself and I use it probably a hundred times a day. Another app I use a lot is called Rectangle. I used to use an app called Spectacle. I actually think I have one on each computer, but I love that Rectangle is open source.

And really, all it lets you do is very quickly and easily with keyboard shortcuts, move things around your screen. So it'll let you quickly take one window and jump into the right half of your screen and then take the other window and you can jump into the left half or the top and bottom halves just to kind of manipulate things and move them around quickly.

And 1Password is a fantastic piece of software. I use it every day. We have a family plan that my wife and my parents are on. I store credit cards, passports, logins for every website. I use it to create a unique login for every website so that I don't have any passwords that are duplicated.

I store a lot of two-factor codes in there instead of Google Authenticator. It's great because you can access those codes from your computer or your phone. I'm a huge fan of 1Password. I've been paying for it since 2013. And if you go to allthehacks.com/1password, you can try for free for 14 days.

I think it's fantastic. All right, Notion is another piece of software I use a ton. It's a web app, but I use it all the time to organize my thoughts. We have a whole Notion setup for our home and, you know, just keeping track of everything there, our child care schedule.

I use another Notion doc for our podcast. So where Google Docs, everything is a doc and you have to link to another doc. This has a bunch of hierarchy. And so I use it to organize thoughts on so much. Another new one is an app called BlueStacks. It's a Android emulator for the Mac.

And I don't really do any Android development. But why I think it's fantastic is there's always a handful of mobile apps that just don't have a website, don't have a web version. And a great example of that is our baby monitor. We use an app called Nanit, and there's not a way to access the camera from your computer.

But when I'm working, sometimes I want to check and keep an eye on our daughter. And so I just pull up BlueStacks and I'm able to do that there. So it's a free piece of software that basically gives you access to everything on Android on your computer. So I think that's the core of the apps I use on a day to day basis that really help me be much more efficient with my life.

I think that wraps up this listener Q&A episode. I hope there was a lot of information that was helpful and there will be links to everything we discussed in the show notes. If you were one of the people that wrote in, hopefully you got a great answer to your question.

If you have other questions, please feel free to reach out. Chris@allthehacks.com, ask away. We'll do this again and I'll try to get to as many questions as possible or I'll respond to you on email. This was a lot of fun for me. I really enjoy hearing from you guys.

So please keep that up. Finally, I'll just say it again. If you haven't signed up for the All The Hacks newsletter, that is going to be the primary way outside of this podcast that I communicate, send hacks and give updates. So please head over to allthehacks.com/email and you can sign up and I will get that next issue out shortly.

Thank you so much for listening. I really appreciate it. We'll be back with a guest next week. See you then. I want to tell you about another podcast I love that goes deep on all things money. That means everything from money hacks to wealth building to early retirement. It's called the Personal Finance Podcast, and it's much more about building generational wealth and spending your money on the things you value than it is about clipping coupons to save a dollar.

It's hosted by my good friend, Andrew, who truly believes that everyone in this world can build wealth and his passion and excitement are what make this show so entertaining. I know because I was a guest on the show in December, 2022, but recently I listened to an episode where Andrew shared 16 money stats that will blow your mind.

And it was so crazy to learn things like 35% of millennials are not participating in their employer's retirement plan. And that's just one of the many fascinating stats he shared. The Personal Finance Podcast has something for everyone. It's filled with so many tips and tactics and hacks to help you get better with your money and grow your wealth.

So I highly recommend you check it out. Just search for the Personal Finance Podcast on Apple Podcasts, Spotify, or wherever you listen to podcasts and enjoy.