Navigating Your Money, Points, and Career + More Listener Q&A with Kevin Rose
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From navigating tricky financial decisions to optimizing points and miles to managing your life and career, today I am teaming up with my good friend Kevin Rose to tackle a bunch of your questions. So whether you're looking to improve your travel game, dial in your life, or even just get a few new podcast recommendations, this episode is packed with insights. I really hope you love it, and thank you to everyone who sent questions in. If

If you're new here, I'm Chris Hutchins. If you enjoy this episode, please share it with a friend. And if you want to keep upgrading your life, money, and travel, click follow or subscribe. And if you want to submit a question for the next one of these, head on over to allthehacks.com slash AMA. Now let's get into it right after this.

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allthehacks.com slash superhuman. Kevin, thanks for helping me do this.

Dude, I'm glad to be here, man. I'm bummed we couldn't do it in person, but thanks for coming on my show and doing my AMA. These are fun. Always learn a lot about the hosts and you have so much great knowledge to share here. So I'm excited to learn some stuff as well. Yeah. So I thought the way we do this, some of these questions were ones that actually your listeners asked you. Many of them are ones that my listeners asked. And so maybe you can help kind of interview me a little. I'm going to bring up some of the ones that I think I'd love your take on too, because

One of the questions is actually about advice. And I was like, I get a lot of advice from you. So I think it's going to be valuable for everyone listening to get my perspective and your perspective. The feeling's mutual, man. I think we're really good at that. For people that don't know, you and I have an ongoing text thread and then phone calls all the time. And we're always picking each other's brains on all different kinds of things. So this will be fun. Yes. And if you're listening and you enjoy this,

Send me an email because Kevin and I have an idea of making this kind of a recurring thing where people can send in questions on any aspect of life. And we'll do a show where we answer questions across both audiences and whatnot. So send that in.

I broke the questions down into a couple categories. We'll start with money and then travel points and miles stuff. Maybe that's one where I'll take most of them. Yeah, you are the points master. So I defer to you on all things points for sure. Perfect. All right, let's do it. All right. So let's start off with the money category. Robert wants to know, many of us who bought a home pre-pandemic are benefiting from great mortgage rates. I definitely miss those days.

As we consider our next home purchase, they have a growing family. There is a big decision as to whether we rent our current home to hang on to this cheap debt. What do you think? Yeah, so this is something that we faced, right? We had a place in San Francisco. We had a growing family. We had a daughter and we decided to move. And it was like, what do we do? We have this low mortgage rate. We also had a pretty low cost basis in the house. And for me,

I just don't want to be a landlord. Yeah. That's what it ultimately came down to for me. I think it would have been profitable to keep the house and rent it out. I think at the time we probably had the income where we could have gotten the second mortgage without an issue. But at the end of the day, how much incremental money is that going to be? And do I want to be a landlord? And...

The math for being a landlord works really well if you have full occupancy, but the margins on it, at least when I was doing the math, seemed to be like, oh, you know, 10, 20%. But if someone's not there for a month, like someone moves out and then you got to fill it, it just felt like all that headache, getting the call that the dryer breaks, something's flooding. I don't know. I just didn't want to deal with it. So as much as I felt like I had this great asset, I

I just said, I don't want to be a landlord. I will find other great assets to buy or invest in or do something with my time. And I sold it. Yeah. One question for you there, because when you're thinking about this, I was in a similar situation where I had a house, beautiful home in Portland, Oregon that I could have rented out, but I decided against it as well. And I had a very insanely low, like two point something ish interest rate. So definitely could have made money. But when you think about, okay,

If you take that capital and you put it into the public markets, are you thinking like, I'm just going to put this in an index fund and expect to get 80% return eventually or annually? And then also, what can someone expect to make on a home rental, not just monthly, but with the appreciation like net, with everything combined? Do you know what that number would be? I don't think I know the number off the top of my head, but historical home appreciation, I want to say somewhere in the 2% to 3% range. So...

The difference though, is if you own a home and you have a mortgage, you're levered up. So you don't have to, when the stock market, you put in a dollar and if that dollar grows 8%, great. If you know in the house, you get the appreciation of the value of the home, but you only put in oftentimes 20%.

I'm going to step back a little bit. When I made the decision not to keep our home, interest rates were still very low. So we got a very low interest rate on a new home. So the math I was doing was keep holding versus renting as a landlord. That math might be very different now, right? I don't know how much rents have changed.

given the interest rates, but your mortgage rate, given current interest rates, might be so low that it's a no-brainer that you really should be renting this out, right? If the profit margin wasn't 20%, but it was 50, 60%, I probably would have kept the house and rented it out. But I wouldn't be looking at it as an investment in the growth of the asset of the home. I would be looking at it as a cashflow business that will require my time and will probably have some unoccupancy, some wear and tear costs and all that kind of stuff.

The other thing that I should mention is in the US, I think if you've lived in a house and talked to an advisor for, I believe it is two or three of the last five years when you sell it, you get the first $250,000 tax-free or $500,000 if you're married. And so if you're in a situation where your home is appreciated a lot and you decide to rent it out,

know that if you rent it out for more than three or four years, you're going to lose out on that tax-free gain because it's only for primary residences. So that's just one important consideration. If the house hasn't appreciated at all since you bought it, not a consideration, but there is an element of tax-free gains that you might be giving up to rent it out.

But I didn't have to think about this with regard to interest rates when I did it. And that might change the calculus. A lot of people say, hey, I like a little bit of real estate exposure. You know, maybe I don't want to own a second home directly. Obviously, this is not a financial advice, but do you ever consider like REITs or anything else when you're looking for some of that exposure? Honestly, if you want exposure to the asset class, investing in one single property as a rental property is probably not very diversified.

The downside of REITs as an investment is that they're taxed as income. So you don't get the long-term capital gains benefits. So maybe you could make a case that they're better suited for a retirement account where you're not making that distinction. REITs are something that I've had in my portfolio in the past. And given that I have such a large chunk of my net worth in my primary residence, I've kind of said, you know what? That's enough real estate for me. I don't really think about it.

All right. Let's move on to the next question from Tyler. You've talked about learning the skill of spending. What things have you been happy to spend more money on? Yeah, so this is interesting. I've had a couple of friends, you being one of them, that have encouraged me to say, you know what, as you make a little bit more money, maybe don't be so frugal or many times cheap is a word that's often been thrown around. I don't associate it with it.

Listen, I thought you were going to get a divorce for a hot minute there. I'm joking. But also at the same time, like you were being so cheap. I was like, how is your partner dealing with this? And so I was like trying to get you to unlock a little bit of that fun and just not worry about every little expense because you were doing so well. But anyway, yeah, continue. Yeah. So there are a handful of things that as we've had more money, I've thought, okay, let's spend more money. And one of them is just food. Right.

right? Like just good quality food. I think the more research I've done, the more I've talked to people. I did an interview with Dr. Casey means at your house. I think it might have come out by the time this episode comes out to

talking about food and processed food. It just feels good to spend money on your health. That can be food, that can be a doctor, that could be a medication you think will improve your health, but your insurance doesn't cover. It takes a lot of different forms. Maybe it's diagnostic tests that your insurance doesn't cover just to kind of baseline how you're doing. I know I've done DEXA scans and CO2 max tests and that kind of stuff.

That's one big bucket I feel good spending more money on than I used to. We have children, things related to their growth and education, whether it's an extracurricular class, whether it's school, whether it's some other program, that's one that's been easy to spend on.

One that I feel like we finally, and maybe kids pushed us over the edge, but just nonstop flights. And I mentioned in a previous episode, not taking budget carriers, right? Nonstop flights on carriers where if something happens, you know that you're going to be taken care of and not be told there's a flight in two or three days. I think we all remember what happened on my bachelor party when...

Spirit Airlines just stopped flying to Columbia and they were like, sorry, go stay in a hotel. We'll figure it out in a few days. And we all had to scramble. So that's just something that's somewhat a non-negotiable. Like we were looking at flights the other day. It was like $300 on a major airline and like $59 on Frontier. And it was like, you know what? I just don't want to be stranded at the airport. And

I really struggled with that one because that was a pretty big delta, but we made this money rule of we're not spending money on budget carriers unless it's the only option. And if we are, we're just going to pay for all the extras. In this particular case, it was a flight that if something happened and we needed a flight two hours later, it'd be okay. But if it was the next day, it'd be a problem. And so we just said no. I've never been one to spend a lot of money on clothes, but upgrading from the H&M $10 clothes that fall apart to like...

more like just quality clothes, not designer clothes, that kind of stuff, but just like quality brands. That's been one that I really like. And then just paying for convenience and time. Amy and I, and funny, you mentioned whether it would be the end of our relationship. I now play this role with Amy sometimes where she's like, you

you know, I'm driving to Daly City tomorrow. And I'm like, well, it's like 20, 30 minutes away. Why are you going there? And she's like, well, you know, they want $5 to print a return label for this package. And I'm like, no, let's just pay the $5 and save the hour of our time. And Amy and I go back and forth on this all the time. But we've really, I think, in the last year gotten better at if this thing's going to cost $5, $10, $15, $20, $30, and it's going to make our lives better, pay for it. If it's not,

Absolutely not. I'm not going to throw around $5 just because it's possible. It's got to be worth it. But if it saves you half an hour, I think I've gotten much better at valuing my time. So those are some of the things. I'm curious what your take is here, because you're someone who I think, you know, you've been a little bit more the yin to my yang, I guess here, maybe more opposing forces. I think there's a couple of things here. Like you can stack rank and take the top five pain points that you have in your life.

and say, if I apply a little bit more capital to these pain points, would they get easier slash go away? And so for me, I hate flying. I really do. I hate it. It's like my least favorite things to do. So, you know, for me, a first class ticket is quite nice and gives me a little less anxiety, a little bit more room to kind of spread out. So I treat myself to that. And I would say,

If you can kind of go down that, whether it's childcare or you name it and just kind of check those things off, that's huge. And then also I would say the kind of spontaneity of doing one luxurious thing for yourself or partner that you wouldn't normally do is a huge unlock.

it's kind of a fun forcing function to say okay we're going to go out to dinner tonight and we're going to buy a $200 bottle of wine or just something that you would never do you know maybe once a month or something and say I heard about this crazy region in Italy these super Tuscans if you're a wine person I'm just making this up fill in the blank for whatever yours is here you know doing that one kind of big bold thing can feel a little bit wild kind of very exciting moment to have with a shared friend or partner right so that's kind of my key things yeah I

One of the things I like doing in that camp is invest in a thing that will force you to do something you want to do more. So we actually asked for them for gifts, which I think gifting is a great place to push yourself here because sometimes...

You know, it comes to holidays. My parents say, oh, what do you want for Christmas? What do you want for your birthday? I'm like, I don't really need anything. And they're like, well, we're going to get you something. So if you have any ideas. And one year we were like, why don't you get us some inflatable stand up paddle boards? It's like, I don't need this. It felt to me like what you were saying with the wine, a couple hundred bucks for something that you like don't need at all. But now we've used them all the time.

take the girls out in the bay or there's a couple like down by Foster City and there's like a bunch of little inlets with water. When you buy something that forces you to do a thing you want to do, I think that's cool. If you have the personality that I remember my parents had a Nordic track in the house, which I think they bought because they thought it would force them to work out. But it basically just sat in the basement. If you don't have the right personality for this, do not buy something. But if you do, I think it can be pretty cool. Yeah, it's a great point.

All right. Krishna would like to know, where would you invest your money to maximize earnings if you have a less than six month horizon? This one's actually a pretty easy one because I wouldn't invest my money in the traditional sense. There isn't a stock or index fund that I'm excited to invest in. Now,

If you consider investing in US treasuries or into a high yield savings account and investment, then absolutely. For me, if it's less than a three year horizon, I want to invest that money in something that I will not have to sell if the market's down. I have no idea if six months from now, the market will be up 20% or down 20% or down 40%. And like, I see a real possibility. This would be true any day of the week, any day of the year. So this is not a comment on the economy, but

But it's very possible that six months from now, the market's down 40%. And if I need money in six months, I don't want that money to be down 40% when I have to sell. And so reasonably, I think if something has a three to five year or longer horizon, I'm totally fine putting that money to work in the market

in an index fund, probably VTI for me. If it's short term, it's either a high yield savings account, or you could go buy treasuries, or you could just buy like SGOV, or if you're in Vanguard, VUSXX. There's a lot of mutual funds and money market accounts and treasury ETFs that kind of are yielding anywhere from, yeah, I'd say a little over 5% right now. But there was another question that I'll just jump into, which is what are you doing differently after the Fed rate cut?

The short answer is nothing. I expect all high-yield savings accounts by the time this is out will now just be 50 basis points less, and we'll probably see all interest rates on short-term things down 50 basis points or half a percent. But I think...

At that point, whether it's four and a half or 5%, my answer still holds. I'm investing in cash or short-term US treasuries and nothing else. My answer here would differ probably a tiny bit in that I would, and I know we're both investors in wealth front, full disclosure, but I'd probably just do a simple little bond ladder.

over the next six to eight months and just kind of lock in those rates and still have access to some of the liquidity if I needed it. Yeah, that's fair. Yeah. I mean, you could just, there might even be an institution out there with like a six month CD with a really high rate. Yeah. I guess if you know the exact duration, locking it in might make sense.

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All right, let's move into points. You had some questions from several people here asking about points, which you are, of course, an expert in. Jay wants to know, what is the most overrated hack in the credit card points world?

So I thought a lot about this. I think the one for me, I hear so many people talking about how awesome it is that certain cards earn 5X or 6X or something in a category or rotating categories that are all capped at $500 a month or $6,000 a year, depending on the card. If you compare that to a card that's earning 2X on everything, you're getting an extra three points per dollar, which is not nothing, but on $6,000, so it's about 18,000 points a year.

If you consider that like a great signup bonus is probably somewhere on the order of 100,000 points. Then if you just opened one extra card every four to five years, you would have about the same outcome. And so I think,

When I go to start optimizing all of my spend and how I'm earning the most back on everything I do, I try to not play in the margins where it's not that impactful. And I think the downside with a lot of these cards that have rotating categories is not just that you're capped in your upside.

But it's that you hit the 500 and then you have to switch cards. So it's like, this is my grocery card up to $500. And then the next time I go to the grocery, I have to remember this other card. And by the way, if it's groceries, you get 4X on the Amex gold card. So if that was your category, the delta isn't between three and five, it's between four and five. So I just think that there are bigger opportunities than that.

Look, if you have one of these cards and you want to spend on it, great. But targeting one of these cards to try to add to your game doesn't make as much sense to me. Now, the flip side of that, which wasn't asked, which is what's underrated, is probably two things. One is retention offers. And I bring this up because it juxtaposes the previous one so nicely.

I called for my Amex Platinum card and said, look, fees high. I don't know if I'm using all the perks. Is there anything you can do? And they said, well, if you can spend $3,000 in the next three months, we'll add a bonus. And in the past, that bonus has been anywhere from 15 to 25,000 points. These offers change almost weekly. So I would say if you're looking for one of these and you don't get something you like, wait a week and you could do it all on the chat in the Amex app or on the website.

So here's a case where you could be earning that same level of bonus points you would get from having to maximize $500 a month in one go. Seems like a much better use of time. So that's one of the underrated things. Anyone who's not trying to negotiate retention offers, especially from Amex, I think that's a big opportunity that most people aren't doing.

And then the second is around business cards. And I think most people assume that they don't own a company, so they can't have a business card. And business cards are pretty lucrative. There are a lot of great cards with great earning and really great welcome bonuses, and even welcome bonuses with really low annual fees or no annual fees. And the qualification for a business card does not mean you own a profitable business. It could mean...

you have any type of business income or a business plan, or let's say you have a blog that you're looking to start in the future and it might become a business. Let's say you've done some consulting, you've sold something on eBay, Etsy store. Like if you do anything that could be considered business activity that's not working for an employer,

that qualifies and you can get a business card under your own social security number as a sole proprietor. I was going to say, when you start these business cards, though, I'm pretty sure they ask you for an EIN and a business entity name. Yeah. So you could do your EIN or you can put your social and say, I'm a sole proprietor. Because many people with big million-dollar companies operate them as a sole proprietor under their own social. They don't have an EIN. So that is on the list. But I'm

I think I got my first business card a couple years out of college. I was like, you know what? I did consulting for one company on the weekend, like a project. Anything you do, you want to sell something on eBay. Now you've got some business income. You have a rental property. We talked about earlier, you have some business income. So I think business cards are pretty lucrative. And if you go to our website and click on cards at the top, there's a list of all the card offers. And the best card offers are often business card offers. So something to consider.

One last quick question about this genre of things. And I have a really hard time because it is that mental switching, like you mentioned earlier of like, okay, shit, I'm at the grocery store. Which car do I pull out? I'm at dinner. Which car do I pull out? And has this offer changed?

If someone is listening and say, hey, Chris, I love all the advice that you give, but the points thing is just a lot of context switching in my brain. I just want to have one card to rule them all and just be like, cash back. This is the best. What is that today for you? So I built this optimizer tool, and I'm actually going to bring it up in a little bit because I used it to answer some of these questions. But there's a huge bump to your ROI when you go to two. So I'm going to say...

I think anyone listening to this show can probably handle two cards. And the mathematically most optimal for points earning for the average kind of household spending, I think like $100,000 a year in America, it was the Capital One Venture X or the Venture. They're kind of the same card depending on perks and the Amex Gold. That model is you have one card for dining and groceries and you have one card for everything else. You only have two things to remember. If you truly only wanted one card,

A pretty interesting one, which doesn't earn points, is the U.S. Bank Altitude Reserve. They have this real-time rewards program that basically allows you to earn effectively like 4.5% cash back on transactions

travel and mobile wallet. So any Apple Pay, Samsung Pay, Google Pay, that kind of stuff is an interesting one. And then if you want just a simple proposition, Bank of America's preferred rewards card, if you can put $100,000 in a Merrill Edge brokerage account, which could be like a Roth IRA or some stocks you own, it doesn't need to be something you don't already own. You get a 3.5% on travel and dining, 2.625 on everything else in cashback.

So it doesn't get you the points, though. I did this episode on points versus cash back and realized like a lot of times you can buy points. So if you want something simple, those are kind of the choices I would go. Last question in this vein, and only because I'm personally curious, I spend a crap ton on Amazon. And when I use that Amazon card, I'm getting 5% back. And then if I say, hey, deliver this package a couple days later, because I really don't care, I get 6% back. Is that worth doing?

So Amazon card for sure. I've always seen Amazon say like, deliver this a little bit later and you get like a dollar reward in your Amazon. Right. I have not seen the 1% back. So if that is an offer, I feel like that is a huge deal. Is that a thing that regularly happens? So for me, and I get that they could be beta testing this out on a small pool of people or whatever it may be. But when my Amazon card is plugged in as the payment method, it says, hey, we're going to give you 5% back or...

Or if you bundle this with your weekly delivery for me is on a Friday, we will give you an additional point. And so they give me 6% back on it. And so I always say bundle it with Friday. I always use the Amazon card on Amazon and I will immediately after this, like I'm fighting the urge to go check it while we're talking because the fact that I've overlooked this or not seen it makes me disappointed in myself. I'm just bringing you some alpha, dude. I'm sorry. Yeah. So amazing. That's great.

All right, let's move on to the next question. Chad wants to know, how do you think about a broader long-term strategy for obtaining multiple welcome bonuses each year when accounting for all the various card program rules? And there was another message from D-Turn on Instagram about how often me and my wife are signing up for cards each year to get a bonus. This one's interesting because I'll link in the show notes to this great tweet, or I guess X post now is what we're supposed to call it maybe, where

Where someone and his wife opened like 22 cards over the course of the year, racked up a couple million points, and their credit scores went up.

And so it's interesting because a strategy for a few welcome bonuses each year, you can push it even harder than a few. I think in the question, Chad had like three to four. We don't push this hard. There are people out there who push this really hard, go for 10, 20 cards a year, opening up tons and tons. I don't push this as hard as can be pushed, but...

But in general, I think there's a little bit of sequencing to think about. So one, a very popular bank is a 524 rule. You're not going to get approved if you've opened up five cards in the last two years. So that would be a good place to start. Capital One's kind of a little bit more sensitive around how many cards have you opened. That's a good place to start. Amex, on the other hand, less sensitive. So maybe end there. S4C.

As far as the specific rules, I probably should just do an episode on this because I'm not going to go down to every nuance of, you know, how many charge cards you can have and how many of this. So definitely read those rules. So you're not applying for a card you can't get approved for. But for me personally, I think I'm at the point where anytime there's a really big, interesting offer, we'll jump on it.

So Hilton has a bunch of increased offers right now. But earlier this year, they had increased offers that also threw on an extra free night certificate. Jumped on that. Things like that are cool. Some offer crosses 100,000 points. That's pretty exciting for me. But we're probably at the four to five a year camp, not the 20 year camp. And so maybe once a quarter, we'll sign up for something. Because at the end of the day,

you are probably going to earn somewhere between 10 and 20 X points on hitting a minimum spend on a welcome bonus. Right? I think as of the time recording this, there's a business card where it's 90,000 points. I think you have to spend four or $6,000. So like you spent four or $6,000 on any other card. You're not even getting 30,000 points. So like huge opportunities and welcome bonuses, but like,

I think you just have to really dig into the rules to get to that second level. And I just, I don't have the time to think through the nuance of like which card here, there, but having a second person, a player too, which again,

you know, sorry to the negative review that left us that said they're leaving the podcast. They loved it, but they didn't like that I called my wife a player too. This isn't a video game. And I'm like, yes, in this industry, that's just the term. So if you hear me refer to Amy as player too, it's not out of anything other than trying to use standard industry terminology. That's amazing. So somebody got really pissed off that you said that. Somebody left a review that's like calls his wife a player too. And it was like, show has good content, but it's not a video game. And I'm like,

All right. Which, by the way, there's another question about ads that we'll get to at the end. If you're the listener who sent in that question, we will get to it.

And if anyone actually knows you as a couple, everyone would know she's player one anyway. So that's absolutely true. All right. So we got a couple other questions that are in the very similar vein. You're hitting on something here that a lot of people want to know about, which is, you know, Christian is asking about how do you think about recycling and canceling credit cards to be eligible for bonuses again? And then Jonathan also says there's so much talk about credit card signup bonuses, but you never talk about what to do after you get them. Does everyone cancel their cards? Yeah.

The products change. How does this affect 524? Lots of questions about signing up and canceling. Yeah, so...

I have like a pretty quick process I run through. If the card is not a card where I'm regularly spending on it and I've gotten the welcome bonus, I always wait until after 12 months, a full one year, because there are some programs that kind of monitor people who open cards and cancel them within a year. So I always wait a year. Almost every, if not every credit card issuer will refund the card

annual fee if you cancel within some period of it posting. So usually have like a year and one or two months to cancel and get that feedback. So even if your goal is just cancel and get the feedback, do it 366 days later. That said, retention offers. I've had times where my Amex Platinum retention offer was we'll just waive the annual fee, right? There's enough perks on an Amex Platinum card that

if you could get it with no annual fee, you would make money every year. So if I can't get a retention offer, which I try for every time, then I'll try to product change. And so within almost every issuer, there's a set of cards that you can change to. And so you could go from your platinum down to a gold. You could go from many high annual fee cards down to no annual fee cards.

So those are options. And then if it's a high annual fee card and I'm not getting any perks from it, I'm not spending any money on it. Can't get a retention offer. Can't product change it. Yeah, then I'll cancel the card. Depending on how long you've had the card. I think maybe the only exception is if you're new to this and it's the one card you've had for 30 years or something, you know, it's going to have a big impact to lose that history on your credit score. So I'd really try to find a way to do one of the former product change or retention to make it work.

As far as how it affects 524, the rules around 524 are just how many cards you opened. So whether it's active or not, it's going to count towards 524. So canceling or not doesn't change that at all.

One thing with just my product hat on is I'd love to see from you, Chris, is eventually an app from you that is a push notification. I can turn them on and it's like, Chris is making a move. You're getting into this new card. You're exiting this one card. And then a little rationale behind it would be so killer to have that in real time. Because I feel like this is something that you like people that really want to do it. They have to be on top of it, right? Like that's the problem, at least for me is like, if

If I miss one of your podcasts, I may miss a very important insight. But like, have you ever considered doing anything? Or is there a way for people to consume kind of the moves that you're making in a more real time fashion? The challenge of the podcast is a few things. One, we're recording this right now, September 20th. It probably won't come out till early October. So that's a challenge. Two,

As a lot of people who've listened for a while know that recently, I've been asked to not use the name of a very popular bank that if you've noticed me not using, you'll know why. So that makes it a little tricky. On the flip side, with email, when I send a weekly newsletter on Saturday morning, I can add to it Friday night or Saturday morning. And so when Amy and I got those Hilton cards with the free night certificates, we put that in the email multiple times.

So I would say for the more real time, here's an awesome deal I found. Here's a card I'm getting. You know, at the time of recording this week's newsletter tomorrow morning, there are 18 credit cards that have an increased welcome offer in the last two weeks. 18 cards bumped the welcome offers. So that's going to be in the newsletter tomorrow. I could tell you about it now, but by the time you hear this, Right.

they might be gone. So if you haven't subscribed to the newsletter, it's just a once a week, Saturday morning email that is all the best deals, fines, recommendations, everything from the last week. And you can do it at allthehacks.com slash email. Awesome.

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All right. Anonymous is writing in. I'm looking for ways to earn points beyond what I do with my regular spending. What options do I have? I looked at a buying club and I'd be good to clarify what a buying club is for people that don't know, but they are willing to pay less than the cost, sometimes 50 to a hundred dollars less. It doesn't make sense for me. What am I doing wrong?

Yeah. So for those who aren't familiar, right now is a particularly special day for buying clubs because it is iPhone delivery day. And so buying clubs, basically, there are people and mostly in other countries who want to have access to products that you can only get in limited quantities in the U.S. So on iPhone delivery day, there is basically an unlimited number of people who will buy your iPhone at cost.

and probably often give you a shipping label so that you can ship it to them. And so what you do is you get to buy the iPhone and keep the credit card points or cash back if it's a racketing cash back portal, and then sell your phone. Most of the time, these products are not at a profit. And if it is at a profit, it's maybe a dollar. So buying groups are often people who are buying things so that they can earn cash back

or credit card points or hit minimum spends on welcome offers. And so they're willing to pay or take a 2%, 3% loss. So depending on the price of the item, if you're buying a brand new iPhone that's $1,500, losing $50 to be able to put $1,500 on your credit card might be worth it.

I'm curious here. Let's take the $1,500 example. $1,500, if I'm getting 3% cash back on that, let's just say through some finagling or something, that's $45. That's an awful lot of time for $45 to go pay, have it shipped, get the label, put it on, ship it back out. Is that just the delta people are looking for here? I'm looking right now, just for fun, at a buyer's group website that I'm in, and I'm just seeing what the iPhone offers are.

Right now, I don't see an iPhone offer. But there is, for example, a Google Chromecast with Google TV 4K. It's $41.50. Though they're offering $41.50, it costs $40. So it might make sense if it's the difference between hitting a welcome bonus or not. But I think that you've really got to decide that this is a business you want to do. So there's really a question about like, do you want to get into a business? There's a lot of risk. I know people have done this and a package doesn't show up. You got to figure out how to deal with that. It's kind of like...

We talked before about renting your home, like it becomes a business. If it's just about trying to meet a bonus where you need to spend $10,000, that could make sense. If it's about a long-term recurring thing, I think you got to put more time and energy into it.

There are a lot of other ways people do this, things like gift card reselling. I'm going to be honest, I'm probably not going to go into a lot more detail about this publicly just because a lot of the things people don't want shared in a wide audience. But it is a topic right for discussion in our All The Hacks community. And so if you really want to go deep on this, head on over to allthehacks.com join.

All right. Next up, Randy wants to know, now I have so many Pepper points, which I have no idea what these are. What do I do with them? When we were talking about this, you're like, I don't even know what this is. Amy has a note in this doc because she reviewed some of these questions. She's like, I don't know what this means. There's an app called Pepper, which similar to the question before, is a place you can go buy gift cards. You can use a credit card to buy gift cards.

speculation is that Pepper's raised so much venture capital money that they're subsidizing gift cards at a pretty aggressive level. You earn Pepper Points when you buy gift cards, and you can use them to buy more gift cards, which just saying it out loud sounds ridiculous. But you can earn upwards of like 12% back on Amazon buying Amazon gift cards, but you earn it in the form of Pepper Points. And so the answer is like, what do you do with them? You buy more gift cards. That is the only thing I know you could do with Pepper Points.

But if you're looking at trying to offset when you buy things so that you can get a better deal and you're willing to take on some risk that the extra points, these bonus points, sometimes they say we'll pay out 4% now and another 8% in two weeks.

Obviously, if Pepper goes out of business in two weeks, you're not going to get that 8%. But yeah, Pepper is an interesting app for buying gift cards. And if you need a referral, I'll put my referral number in the show notes. Awesome. All right. Tyler wants to know Alaska plus Hawaiian merger thoughts. There's a lot of people that are talking about this as if it's this huge deal. And I think part of the reason it's a big deal is that

We've had just an administration that has been a little bit allergic to allowing deals to go through. The other part of it was that Alaska points are very hard to get and super valuable. We're leaving tomorrow to go to Iceland. On Alaska, it was 27,500 points for a flight to Iceland from San Francisco in economy, but pretty good deal for points. And the only transfer partner for Alaska is Built, which...

which there's one card. And unless you pay rent, you know, it's reasonably challenging to rack up hundreds of thousands of points.

The reason this is super exciting in the points world, and the reason I'm excited personally, is that for now, Hawaiian is a transfer of Amex. So if you have a bunch of Amex points, you can transfer them to Hawaiian. They've announced that by the end of this month, so by the time this episode's out, Hawaiian will support transfers to Alaska. And so there is now a way to go from Amex to Alaska. So I speculatively transferred a few hundred thousand Amex points to Hawaiian a few

a few weeks ago when they had a transfer bonus, hoping this would be the case. Now that it's kind of locked in, there's just a lot of chatter of people saying, is Amex to Hawaiian to Alaska the best use of Amex points? And I would say, if you have a trip planned, yes. It's not worth transferring your points to Alaska if you don't have a trip planned or you don't have any way to know you could use them because maybe the trip you want to take, the best deal is on Air France. And like now you're stuck with a bunch of Alaska points.

But can you get a tremendous amount of value from Alaska points? Absolutely. So people are just really excited, myself included, to have another fantastic transfer partner. Realistically, I expect that at some point Amex will drop Hawaiian and this will not be allowed. But...

The Department of Transportation issued some pretty aggressive guidance on this merger that was like, you can merge, but you can't devalue any of the awards on any of your frequent flyer programs, and you must allow points to transfer one-to-one. And then there was a separate thing I sent out in the newsletter a couple weeks ago, which, by the way, the past newsletters are all on the website as well, where the Department of Transportation is saying,

I don't know if it's like investigating or sent a letter to a bunch of frequent flyer program like American United and said, hey, you need to explain why you're devaluing. You need to explain this. So for whatever reason, the current administration is taking a big interest in making sure frequent flyer programs are

are not doing anything to hurt consumers. And so maybe they will in some way, shape or form not let this get canceled. I don't know how it will all unplay once the merger is done. If it ends up being Alaska at the end, it'll probably be pretty easy for Amex to drop. But for now, pretty good use Amex points.

All right, let's move on. Lisa wants to know, when playing in two-player mode, what's your take on applying for authorized slash secondary user cards when they're available for free? Yeah, so the biggest caveat here is that being an authorized user on someone else's card shows up on your credit report for most issuers. So if you're player two or if you make your player two an authorized user, that's going to count towards things like the 524 rule. Now, if you cancel that authorized user card, you can usually get that removed.

So the way we've done it is it's not really that necessary. So if I have a card, I can put it in our 1Password and Amy has access to the number at any point in time. She can add it to her Apple Pay. So the only times you really need the card and to be an authorized user would be one, if you need to use the card in person a lot.

And by the way, where you're using it cares. I think we've all probably been in a situation where we've either borrowed or lent our card to a spouse and it had the other person's name on it. I'd rarely have ever heard of anyone having an issue. So the only case where I would probably add someone as an authorized user is if there's benefits there. So if you have a card where authorized users get lounge access,

and you don't have any other means for that, then that could make sense. One thing, being an authorized user doesn't prevent you from getting that card. So if you've been the authorized user on a Capital One Venture Card, and then later in your life, you wanna get the bonus, I would remove yourself from the authorized user before you apply, but you're not gonna be prevented. So to me, only if there's a benefit that you really need from the card, would I say it makes sense.

almost every case, I would say you don't need it. Or the signup bonus is probably good enough that instead of being an authorized user, have your player to go get the card also is another option.

All right. JJ wants to know, is there a search tool that shows Hyatt availability by occupant slash kid count? Yeah, so this is just like the biggest frustration traveling with children is that there are just so many hotels in the world that only allow two people or three people to a room. And so I went and looked. Points, yeah, and a ways.

have the ability to add the number of guests. So you could say three or four, but nothing specific to kids like most of the hotel websites do. So I don't have a great answer here. What I would probably do, which

which is not a great solution, is go to each hotel's website to do the hotel searching if you have kids so that you can find out at least whether the region you're in is one that's pretty restrictive. If you find that almost every hotel where you're going, similar to how the US works, like all allow four people, if you're a family of four, then you can go use any tool you want. But if you're going to Europe, you're probably going to need to check with almost every hotel and you're probably going to find that four doesn't work most often.

All right. Kelly wants to know, what is your favorite website to get points info from?

I don't have just one. I think some of my most frequent followed sites are FrequentMiler, Doctor of Credit, and One Mile at a Time. I usually follow those accounts and maybe a couple others on Twitter. And I kind of scroll from time to time to get my news. And that's what I try to do in the newsletter. I try to filter through the five, six, seven sources I read every week to the stuff that is most relevant. But I'm going to leave a lot of stuff out. So if you don't want to miss a single piece of news about Points and Miles world, I would check those sites out.

All right. Emil wants to know, what is the best card to pair with CSR? Yeah, another one. If you don't know what that is, you could search because I can't say it. If you want to stay in the same ecosystem, meaning under the same issuer, there's a couple no annual fee cards that I think pair really well. One that gets one and a half percent back. And so that's where I would focus my time on.

That said, what you're really missing is a card that earns on everything that isn't travel and dining. And so your two options outside of that issuer are the Capital One Venture X, 2X on everything, or the Venture card, both 2X on everything. Or if you go the cash back route, the Bank of America Preferred Rewards card or the new Robinhood card. Now, I've heard a handful of reports on the Robinhood card about it just being really strict around purchases that...

aren't standard. And the X1 card, which was the company that Robinhood bought, had lots of problems here. So people go to Costco, buy some gold, shut down saying, hey, that's not an eligible purchase. We're not paying rewards on it. I imagine if you were to buy some gift cards, you might run into similar issues. So, you know, I've kind of held off on the Robinhood card for that reason, even though I got my invite because I've just heard a lot of pretty negative reports there. Yeah, there's another one where someone asked about what to do after the Venture X and the Sabre 1.

So it sounds like you're pretty deep. You have two Capital One cards. You've got the Everything card. You've got a Dining and Grocery card. So you're kind of pretty well covered. And earlier when I said a best two-card combo, if you wanted to stay in one issuer, Saver One and Venture X is a pretty good two-card combo. So if I were adding on to that, I'd be looking either at whatever had a really big bonus right now. If you pay rent, I'd be looking at the Built card. And

And then I actually ran through the card tool I talked about, which you can find on the website. I added a little products camp at the top and the best cards to pair with that. Surprisingly, which is one of the cool things about building a tool to optimize this is I would not have guessed these cards had I not done it. But the Wells Fargo autograph and autograph journey cards paired really well. And the city premier card paired really well. So those are the ones I would look at. You like a wine someone you ever like.

credit cards. You're like finding pairings for these cards. Okay. Mr. Smith wants to know, hey, Chris, can you talk more about the services or consultants you know that help maximize credit card points? So there was a lot more context in the question, but it seemed like I realized there's value here. I don't have a lot of time. What are my options? When you've accumulated a lot of points, there are award booking services like Point.me and AwardCat and 10X Travel has one where you can pay a couple hundred dollars and they'll do all the booking for you.

There are a couple people out there who have businesses that cost somewhere around, let's call it $1,500 to $3,000 a year, where they'll just tell you which cards to sign up for. And then, hey, you hit the bonus, switch to this one, switch to this one. I think you could probably do that pretty well if you just said, I'm going to do this three times a year and follow the newsletter and be like, okay, there's a really big opportunity.

Lee Rowan's been a guest of the podcast a bunch. He has this company, Savanti, and there are a lot of other travel agencies. Most of them work on more of a retainer model than a commission model if you want them to also do the points and miles stuff. And the reason for that is there are no commissions when someone's managing all your points and miles. So if a travel agent is going to book your flights and your hotels with all of your points as a kind of

consistent service instead of a one-off service, you're going to want someone who is getting paid because otherwise they're probably not going to be very good at their job if they're willing to do it for free. So those are the options out there. There's not a perfect do-it-all for you. Maybe that's a product I should build one day, but I haven't built it yet. And we'll probably talk about why in a couple minutes.

All right, let's move on to travel. So Ifran wants to know, even on vacation, I feel like I need to fill up the agenda to get the most out of it. I bet a lot of your listeners have a similar mentality. Do you have rules on relaxing and being present or even vacationing at home? Yeah, so this is one where I really want to start switching the conversation. So you're back more involved, Kevin, because I feel like for the rest of these, you're going to have some good opinions.

I think it's tough as someone who wants to get the most out of life. You go on vacation, you're in a new country and you're like, I want to see all these things. We were also on vacation to relax. And so I try to remind myself on every trip,

This isn't the last opportunity I'll ever have to go somewhere. It's helpful that I have a couple examples like that in my life. We've been to Paris and Japan a few times. So I know, you know what? I don't have to do everything this trip. If it's really awesome, we can just come back another time. So that's one. The other is really just thinking about

about the whole sunk cost fallacy, yes, you might have booked a tour. And yes, it's going to hurt if you pay for it and don't go. But if at the end of the day, you want to just sit in your bed and relax and you don't want to go on the tour, like...

Forget the fact that you've already paid for the tour. It doesn't matter whether you sit at home or go on the tour. You're going to pay for the tour. Do the thing that you want to do and learn next time. Maybe we shouldn't book as much. I try in general to not book as much when I'm going on a trip either. Most things can be booked last minute. You're in Hawaii and you want to go on a snorkel tour. Very rarely do you need to book that snorkel tour two months in advance. And very often you could book it the same day or the night before.

So I would absolutely try to leave a lot of extra time, remind yourself that it's not your only trip and, you know, that you don't have to fill every minute of the day. What do you do? Yeah, for me, it's always like, what's the one big thing I'm going to do today? And,

And typically, if you're going on a trip where you want to do some fine dining or you want to eat at a more popular spot or do an adventure at a more popular place, you'll want to lock in those things ahead of time. So the key for me, especially in countries where they don't speak English, is working with the local concierge at your hotel and getting that stuff done months in advance. Because, you know, if you are saying, okay, listen, I'm going to go to Japan and I want to do a one Michelin star sushi restaurant.

or higher, you have to really work on booking that stuff up ahead of time, working with the concierge so that they can actually call and make those bookings for you. And then the rest of the time is like choose your own adventure. I love a lot of spontaneity. So for me, it's like going out and just seeing where the day takes you is a lot of fun for me. And to your point, that can be sometimes the day takes you to a great, you know, traditional Japanese breakfast in your hotel room, right? And you sleep in till 11 because you're jet lagged. That's kind of the way I roll. Yeah.

Yeah, I guess I would say those major things I will try to book in advance. I probably am not as cavalier as it may have sounded at the beginning. But in general, I'm trying to avoid trying to plan too much. It sounds like you are also.

There was one quick question that I'll just read because it kind of detours from, I'm pretty sure you won't know the answer. When you're booking a rental car on points, Julie asked, where and how do you think about the rental car protections? And I actually went back and read the guide to benefits for major issuers. And a major issuer that I won't mention,

which will make sense when you hear the ones I do mention, you are covered. But Capital One, there's actually this line that says your credit card and account and rewards programs need to be used. And in Capital One, that line, even though it's written by, I think the language was the same, is not there.

And then on Amex, it also says if you're booked with your card or your membership rewards points. So I would say major issuer that is not Amex, Cap One, or Citi, good. Amex, good. Cap One, no. And I didn't get a good answer for Citi either.

So the general answer for all cards is go search the name of the card and guide to benefits. And there's usually a PDF you can find that will give you the language. And when you read it, you'll see exactly what's there. But the short one is capital one. I would not feel confident booking a car with points and being covered based on the way it's written.

It's so funny. Very rarely do I book actual rental cars anymore. For me, especially if it's in a denser city, it's almost always just Uber. And you turned me on to this, but you can go to Costco and get Uber cards, $100 worth of credit for $80, which is an amazing discount. Apply those. And then when you're traveling internationally, just boom, pop it out and you're good to go. Yeah. DoorDash, Uber, Instacart seem to always be at Costco. Every time we're checking out,

Grab an Uber gift card, max it limits to grab to load in the account. You can usually get another one the next day. So we'll just log in online. Oh, and Southwest, we bank a lot of Southwest credit when Costco has it on sale for, I think it's about 16% off, not 20% off. We just bank it because we know we're going to use it. So love it. Amazing. All right. Next question, your favorite business class product and one you haven't flown, but want to. So the haven't flown, but want to, there's a lot.

Q Suites, Etihad apartment, ANA first class. I'm going to expand your ask from favorite business to also include first. Singapore first class, which we'll get to when I reverse this question to you. Haven't done any of those. Favorite cabin I've done with you was Emirates first class. We also did business class on Emirates, which was really nice, though first class much better.

Honestly, if I'm limited just to business and not first class, the Air France flight, we went in a new cabin on Air France a couple of weeks ago, and it was really nice. And I think the reason why I have recency bias is that probably been five, seven years since we've done an international trip where we didn't end up just flying United or Delta or some American carrier. And

Look, do I really need the fancy everything? No, but I really like to be able to lie down and sleep on a plane and wake up rested. So, you know, United and Delta might not have the experience of a lot of Asian carriers that are such a better in-flight experience, but I can lie down and go to sleep. And so if those are the flights I find, I'd rather do that direct. But yeah, I would love to be able to find one of these incredible products direct for our next trip to Japan and do that.

What about you? I mean, Chris, you're crazy if you're thinking to go to Japan in anything but business class. Like, come on. We're old enough now. You've banked away enough money. Just bite the bullet. Would you do Japan non-business class? Be honest. I don't think we could pay for it. I

I think that's my answer. I don't think there's a world where for like five grand a person we would ever pay for it. Because when I look at the dollars per hour for traveling with a family of four or five, depending on whether our au pair is coming, like, I don't think we would do it.

But I also think because of the flexibility in our schedule, because the way we play this game, I don't worry about not being able to go to Japan in business class, but I don't think I'd pay for it with the exception of Zip Air, which is basically like Southwest business class. Like you get the

bed, but like even your meal is not included. So let me ask you a question that I know many people can consider this controversial. Like would you split the kids and the au pair into a separate class and you and your wife do a little mini vacation flight and do the lay flat business class, get the proper sleep, be better prepared to take on the day when you do land with the kids in a new time zone?

It's a good question. I think I've got an out to not even be able to answer it because the au pair program has a hard requirement that au pairs can't work for more than 10 hours straight. So you couldn't legally, at least according to their terms and service and what the Department of State puts out, like actually have them work for a full flight to Japan. But the higher level question of like, would we have the kids in the back when they're old enough?

I don't know. I haven't had to make that question or decision yet, but it's definitely one where I brought this up at the lunch table at a startup and I was surprised at how people were so far on two different spectrums. There were people at the company I worked at that were like, that would be the worst thing you could ever do to like, I can't believe you wouldn't not do it. Like it was just one of the very few things I've ever had a polarizing, but completely non-political conversation about. So haven't really thought about

doing that or not. But I do think in the one time we did do business class for all five of us, watching a two-year-old in a seat that like they could have had the same experience in a coach seat felt ridiculous. But I guess when you're using points, it feels a lot less ridiculous than if we were spending $25,000. I know this is a controversial topic and I will say this. If you are going to go on a long flight and you have a nanny, forget the au pair, but you have a nanny that's going to get overtime and is watching the kids anyway, right? And

And if you can, and this is oftentimes the case, if you book far enough in advance, say, hey, listen, I'm going to be one row removed. And granted, my seats are going to be a little bigger. I'm going to be out there with my partner. I'm going to get a chance to get better rest, better night's sleep, wake up a better parent in that new time zone. And my kids are literally seven feet away, but they're going to be

cackling and having fun and watching movies and all that stuff anyway, and I'm paying the nanny anyway, like, I don't know, seven feet removed and to give you and your partner a little mini flight vacation and not have to drop an additional 15 grand on business class tickets for the rest of the family. It seems kind of like a no brainer, but maybe, you know, I'm going to get hate mail for this. Who knows? I don't know. The one thing we have thought about, and I've actually done some research as to whether airlines would allow it.

is putting four people in coach and one in first and swapping some flights. Like, you know, if you're going New York to Singapore, I don't really need first class the whole flight. I just want to get a nap. Could Amy and I take turns getting a nap? But there are some airlines that explicitly will not allow family members to swap flights

who's sitting in the premium cabin. Interesting, because I have gone back when I did do that similar situation. Of course, I'm not going to sit there and say, hey, I can't see my kids for an eight-hour flight or whatever. I'm going to go back there and sit down and sit with them and relieve the nanny and let the nanny walk around the cabin and go do whatever and hang out with my kids for extended periods of time. That's a no-brainer. Yeah, the concern is letting another person sit in the premium cabin.

That's interesting because they let us do it, but I could see that would be a big no-go because I do want to be able to go back and hang with my kids for a bit of that flight, obviously, right? But to loop back to the first question...

What's the best business class cabin you've flown on? Yeah, I mean, the Singapore Air where they actually merge the two seats and then create a little private cabin for you is amazing because they make it very romantic. If you're with a partner, they shut the doors and you have a little pod that is all your own. They put like rose petals on the bed. They want you to throw down in there and they bring you champagne. They kind of just set it up like pretty awesome. Chris, we never did that together. We did the Emirates first. Yeah.

Yeah. There's always some good champagne, no rose petals, no rose petals for us. But you know, when I took my wife to Japan and we did that, it was a ton of fun. And yeah, you always get the slightly upgraded experience. And especially like when you did it with me and we paid all on points, you feel just like, it's amazing. It's like, you're getting this luxury experience all on points. It's, it's crazy. It's so much fun. Okay. Zach wants to know how do you earn globalist each year? And how do you think about opportunity cost?

So this is funny because I've actually not earned globalist before, which is Hyatt's top tier status. But this year I've kind of been trying to, but I've been asking myself whether it's worth it. So I'll share exactly how I think about it. So one, the thrill of the chase for some of these statuses is real. And globalist is an interesting one because it's,

It's definitely the best hotel status out there compared to any other chain. Hyatt does it really well. However, there are these things called guest of honor awards where someone who has globalist status or has earned one can just apply to your reservation globalist status. So basically, you could have no status on Hyatt, but for one stay, be treated as if you had their top tier of status.

So for many people, if you're just going to do one stay a year, it's probably better to find someone or some marketplace online where you can get globalist status for depending on the forums you're looking at. It could be 50, 100 bucks, something like that.

That said, it's one of those things where I'm like, well, I just kind of want to try this and see how it goes. And so I actually built out, and probably no surprise, a kind of pricing spreadsheet to see what would it take to buy your way to 60 nights on one of the Hyatt cards. And on the business one, for every $10,000, you get five nights at a Hyatt, elite nights, and you need 60 nights.

So if you assume you at least have five nights at a Hyatt each year, which if you don't have five nights already, you're probably not staying at a Hyatt enough to care about this status. You got to keep in mind, like, yes, it would be cool to have globalist status. But if you stay at a Hyatt two nights a year,

Pay for a suite and buy yourself breakfast. Don't worry about it. But if you go do the math, which I did, at each level along the way, you get some perks. So when you get to 20 nights, you get two club upgrades. When you get to 30 nights, you get a category one to four free night.

When you get to 40 nights, you actually get one of those guest of honor certificates. So just getting to 40 nights gets you globalist for one stay up to a week. And then I looked at all the perks, the value of the points you earn. If you spend all your way to 60 nights, it's about a 3.25% return on spend in terms of value you get. So 3.25% over a 2% cashback card. Yeah.

Like spending $110,000 on a Hyatt card and getting all those things is worth it. If you value Hyatt points at one and a half cents, because you'd earn for that $110,000, at least 110,000 points. You know, my assumption on all this was earning one point. But if you're spending money on dining or other categories, you can earn two and

And so, you know, the opportunity cost is really just that. Like, what would you spend this money on? Obviously, you have to have $110,000 of spend a year. So if you're spending that on your taxes or other spending, you're not going to get the points you would have gotten. You're not going to get the signup bonuses you would have gotten. So I would say spending your way to Globalist, if you're not already a decent way there, it's probably not a game that most people should play. But it's

If you're halfway there, the personal card gives you an extra five elite nights just for having it. So, you know, maybe it's worth it. I think it's tough because I want it for no reason. And so I'm like excited to chase it down. And then I'm looking at him like we might stay at a high three nights next year. We should just spend 50 bucks, buy a guest of honor certificate online and all today. Yeah. All right. Let's keep moving on. We got a bunch more to get through. Jared wants to know tips of optimizing vacation rentals or extended trips.

So, Jared, I'm going to point you to episode 86, which was all about vacation rentals. So I'm not going to try to answer the question about vacation rentals because I went through almost every option I could think of or find and every way to get it. As for extended trips, I haven't really done a lot of extended trips with the family. So I don't know if I have some great tips for you other than don't over plan. Some of the tips I'm excited to put into place...

A few friends of mine, one of which is a mutual friend of ours, was in Croatia this year, and he enrolled his kids in this cool summer camp, and they were stoked. They were so excited about it. So if you're doing extended travel, I would look at, if you have children, options for finding ways for them to do things that are a little bit more integrated to wherever you are.

Another friend of ours spent a month in Paris and their kids went to ballet class and art class and all these different day summer camps and classes, which one exposed them to a lot of people that they wouldn't normally get exposed to. Gave the parents some time to go explore the city and kind of made it a little bit more like a regular routine instead of go, go, go every day. But once we actually take one of these extended trips, I'll report back.

Awesome. All right, moving into the life and work category. Sarah wants to know, what are your favorite podcasts? All right. So my list, Frequent Miler on the Air is a frequent one. Animal Spirits. Recently, I've started listening to Howard Marks' The Memo. I shared in the newsletter an episode he did with Morgan Housel, which was really good. Sam Parr hosts a podcast called Money Wise, which is pretty cool because he interviews people many times anonymously about how they spend money. And like they go into a lot of detail and share a lot of numbers.

Peter Attia has a podcast called The Drive about a lot of health topics. I like about half of them. The other half, I feel like go too far down a rabbit hole. And then a good friend of mine, you have just revived Dignation, which was a video podcast, I guess, that I listened to for many years, almost a decade or so ago. Yeah, it's been off the air for like 12 years or something like that. Yeah, but it started how many years ago? Yeah, so 2006 or five. Yeah, so almost 20 years. Yeah.

So I was an early fan. There's something nostalgic about watching a show that you watched almost 20 years ago. And that's been fun. But you and Alex have fun reports. I enjoy watching shows where the hosts have a lot of good banter and give each other crap and have a good relationship and all that. So I tune into All In also. And those guys have a pretty good relationship and ability to give each other crap. Yeah, I was...

I was looking at my list here as well. You know, obviously like all in is a fun one. I would say I second the drive. I think Peter Tia has some of the absolute best advice out there on the longevity and health side of things. Human podcast is great. Rhonda Patrick's podcast, Alquot, you can find it at foundmyfitness.com. She is a fantastic scientist that just covers all things, health span, wellbeing, cognition, performance, everything.

I would put her right up there with Huberman in terms of like just awesome scientists. She even, I would say, goes a little bit geekier than he does on some things. She only puts out one episode a month. So that's what's really cool is like when you know when you get her episode, it's going to be an insane deep dive. She has one coming out. I can say it because it'll be out by now, but it is not yet on microplastics that is just insane.

mind-blowingly scary. But anyway, foundmyfitness.com. Rhonda Patrick was probably my top go-to longevity and health one. Nice. Now, a couple of these questions we're going to get to now are some of the ones I stole from your AMA because I was like, that is just such a good question. So shout out to the people that asked. So I thought about some of my answers, but I'm going to bounce back to you for yours as well. Great. Let's do it. Do you want me to ask the first one or? Yeah, go for it. Okay. Let's see here.

First one that came in here is you've reinvented yourself several times over your career. How do you know when it's time to leave your job or venture for something new? You go ahead and start this one off. I've had to do this a few times. Ultimately, like a lot of times you just know. And it's really less about do you know it's time and more about how can you get yourself to accept that it's time

And so I try to always put myself in the shoes of what would I tell a friend who has the same situation? And oftentimes, it's about six months ahead of how I'm feeling personally. I think some of the risk in a lot of these moves is financial. So I'd say if you can set aside an emergency fund, or even just set aside three, six months of living expenses in a way that you just feel like it's not going to be a problem if I don't have income or something like that.

That's a little bit how I try to think about it. But you just know, like when you don't enjoy what you're doing on a day-to-day basis, it's time to figure out what's next. And it's really hard to be creative about what's next when you're not happy. And so I oftentimes think you might need to take three months off. And some companies will give that to you. So you could take a month off even. Like you might need space to even figure out what's next, which is tough.

But I think taking that time, I would have never imagined where I would end up now. Like if you had asked me out of college, the turns I made were all a little bit of gut, a little bit of risk, a little bit of getting laid off and just kind of being willing to chase down something I'm excited about.

Yeah, I think you have to ask yourself like a really hard question, which is, is this truly where I want to be? Meaning, are you in the right place but have the wrong role or set of responsibilities? And if the answer is yes, like I love the idea and prospect of this career slash organization that I'm at. I'm just not where I want to be career wise or I'm not where I want to be in a certain position that I'd actually like to eventually have. And if that's the question, like, have you asked for that?

Have you given yourself enough time? Have you had those honest, you know, really transparent conversations with whoever your boss is and said, hey, this is where I'm looking to be. What do you think my prospect is here over the long term? What can I do to achieve or hit certain milestones that would make me eligible for this increase in role or responsibility here inside of this organization?

Now, often other times you'll say, hey, I know this isn't the place for me long-term. It's kind of a filler job, or I thought it was the place, but the industry is going sideways and I don't want to be in this industry anymore. In which case you just kind of have to bail. And I've done this a couple of times in my career where you take a step backwards to move forward, meaning that you may be making a certain salary and you're like, hey, I can get another job in an industry that I think over the next decade is going to have a lot of value for me, but I'm going to take a 20% haircut on my salary. You might have to do that. And oftentimes that's okay.

And then the other question is, am I an entrepreneur? Do I want to start something new? Do I want to go off and build my own thing? And that's a whole nother can of worms that probably we don't have time for today. I think one thing that's helpful to remember, I talk to people sometimes that are like, let's just use a round number. I make a hundred grand a year and gosh, living on zero a year is going to be really hard. I don't have millions of dollars. And it's like, well,

you're not going to do it forever. So maybe that means you're going to quit your job and you're not going to have a job for six months. Well, now you only need 50 grand, but you would have normally paid taxes on that income. So your 100 grand is really more like 60. So six months is more like 30. So if you can set aside 30 grand, now you've got yourself covered for, let's say, six months.

that feels a lot more attainable than trying to replace 100 grand a year. And so think about how many months you need before you might have another job. Think about what the after-tax cost actually is and all the ways you could mitigate it in the meantime. If you truly had no work

What other things could you do to add $1,000 a month, $2,000 a month, that kind of thing? And all of a sudden, it becomes a little bit more approachable. Yeah. So we actually have a ton of questions in here and a lot less time.

So I'm going to propose that we jump into one of them and then I'm going to preview them. And if people like this format, let's come back and finish it. We'll add more questions. Definitely want feedback, whether we focus more on the life, the travel, the points, that kind of stuff. I feel like I'm cutting off some of the part where I feel like you bring the most. So definitely going to have to bring you back for the follow-up. But

But right before we go, let's talk a little bit about how you think about these decisions of changing careers, being more ambitious, pursuing harder things. There was a question that you got that I really liked about how do you think about that differently during a time of your life where you have small kids and there's a lot more demanding stuff personally? And so I'm gonna let you start with this one because I know you've thought a lot about it. This like drive to do more and this drive to be present with your family.

Yeah, this is a challenging one because there's only so many hours in the day, as we all know, and you have demands from your partner, your kids and your existing job. So especially if you have that entrepreneurial spirit in you, how do you peel off that time to actually go and pursue your dreams? And oftentimes that is not what your day job is. Right. I mean, yeah.

It's especially challenging when you have a certain dollar amount that you have to hit every month to cover the family's needs. Right. So for me, what I would say, and I've seen a lot of entrepreneurs do this where they start off and say, OK, I know I've got my day job, but.

I have X number of hours outside of that work. How do I divide it up? So one, I don't get burned out and two, I can really check off those other really important boxes and have that adequate family time. And I think what it is coming down to a couple of things, um,

One is making sure that you always have that work-life balance. So there should be a set of non-negotiables that you have in your life on the personal side that are take care of me first, which is for me, that's health and wellness. It's exercise. It's getting in, you know, that hour maybe of working out or that 15 minutes of meditation per day, whatever that special mixture is for you. That is the most important factor that will help offset any burnout. And the second thing is,

take a good hard look and be honest with yourself. If I catalog my day, I just say, okay, for the next two weeks, I'm just going to write down everything I do throughout the day.

what can be cut and what can be repurposed? Meaning most people do have that Netflix hour or two, right? Or that time when they spend on the weekends, just, you know, dicking around on stuff that they could cut out and repurpose for other pursuits that are more entrepreneurial kind of driven. And so oftentimes, like for example, when I was at tech TV and I went off to start dig,

I was working a full-time job and then my nights and weekends were dedicated to going and finding a freelance engineer and building a small little prototype and setting myself some goals where I said, hey, by this number of weeks out, I'm going to have a working prototype and saying, I actually have to get this to a certain stage and get it off the ground because the

There is this thing where this tinkering can turn into just analysis paralysis and a fear of launching something new. Or, you know, I see a lot of entrepreneurs that say, well, I just can't give up that day job. And my prototype isn't quite thought through or well-baked. And you kind of have to force yourself to actually ship something, get something out the door. And granted, I'm leaning at this from a technology slant, but my point being is that

Cut out the frivolous stuff. Make time for family first, obviously. Set aside that date night once per week with your partner to get out there and make sure that you give them your undivided attention. And then the rest of that free time, go and pursue those passion projects with the aim of actually having a measurable deliverable of launching something so you can see how the market reacts to it. Yeah, I like that. One of the things that has been really helpful for me in the last few years

has been seeing a lot of people older than me building stuff and like making really aggressive, ambitious moves in their career and realizing that like,

it's not over, right? Like I say this in a way that I'm sure people who are older than me are going to be like, you're ridiculous. Like, of course, it's not over. You know, you just turned 40. But I think a lot of times you think, gosh, am I going to have this drive? Am I going to be able to launch this thing, build this thing in the future? Or do I need to do it when I'm a little bit younger? And it's been really nice to see people

one, two decades older than me launching and building really interesting stuff and doing it in a way that I'm really impressed by because they've got more perspective. Or if you go back and listen to the episode I did with Arthur Brooks, he talks about crystallized intelligence. They've just learned a lot. You mentioned earlier, I should go build this product to do this thing. And I think I have some really exciting things I want to build, but I just know how much

building a company takes out of you. And I just don't want to do that right now in this time with young kids that are home a lot more and want to hang out with us. And so I'm okay with the impact that could have on the business. And I'm like, that's a trade-off I'm willing to make.

But it's been easier because I've seen a handful of people who've been able to do the kind of stuff I want to do 10, 20 years from now. And I know that when kids are off in college, I'm going to have a little bit more free time. And maybe that's a good time to go pursue those things. Yeah. I will say one thing to add to that is it's important to let people know that obviously most startups fail. I'm a venture capitalist for my day job and expect 90% of our companies to go to zero. And I...

I have prototyped multiple things where I've gotten them down to the stage of like ready to launch and looked at it and said, eh, I don't like it now. I built it. I don't like it now. And I've scrapped it, never launched it. And that's okay. Like you learn something new and you move on. So that's kind of the beauty of being able to say I'm nimble enough to go out and build something on the side, hack it together. And I'll get a lot better.

better sense of feeling and gut when I both use it internally on my own and then send it out to a handful of friends to use and get collect feedback from. And oftentimes that'll lead you to a no and you don't even launch it. But then, you know, you're back to your day job and said, hey, I scratched that itch. And should the next big kind of tsunami of excitement come over me, I can always go and prototype something again.

So we had a bunch of other questions. I'm just going to highlight them so people know what's coming. A great one about we wake up with no plans and commitments. How do you spend your day? Another one about general routine practices. What are we doing? How we give up time and where we focus on it.

Tyler asked, when do we get rid of an au pair? And I'm curious how you think about that. So we're not going to get to all of these at all. You know, the bridge between technology and kids. How do we think about screen time? How do we think about introducing our kids to technology? Last one was TV recommendations. Man, I'm wrong. I'm like, look at the list. I was like, things must have come in since then. There was a great question about now that we're doing things that we could do from anywhere. Why are we living in high cost of living cities?

Why haven't I moved? Oh, that's a great question. I'm in the same boat, you know? I'm in LA. It's crazy expensive and there's a lot to unpack there. And then finally, the one question I did promise I would answer, so I'm going to hit on it this time and we'll save the rest for next time. Frank asked, why do we have so many ads in the show? It's a funny one because there are a lot of podcasts that have no ads. But I went to a podcast movement and I saw this slide where they were like, here's the average number of ads in a podcast. And it was six to eight. And I was like, well, we're less than six to eight. And

And the amount of time it takes to produce this episode takes a lot of time. And I couldn't possibly have a day job doing it. And I only work with brands I love. So it doesn't really feel like I'm shilling products I don't care about. So...

We have ads because the podcast is free. We have ads because I want to do this full time and it takes a lot of time. And you can skip them if you want. There's a button on almost every player app to do that. I hope you don't because they're all brands I like. But I'm curious, you've worked in an industry supported by ads doing shows like this forever. How do you think about ads? And do you have anything else to say to Frank?

Yeah. I mean, I think, listen, like there is that balance, right? Cause you don't want to just have a blanketed podcast with a bunch of ads, but to me it's always been, and Chris, you can speak to this because you helped me with a lot of the ad sales stuff. I've said no to a lot of advertisers. And I know you're in the same boat that when you actually talk about something on your show, you personally use it. Like you love it. Like you would stand behind it no matter what. And I

And I think that authenticity is the most important part because if you're dealing with like some kind of like random dynamically inserted ad as just an ad, like, yeah, screw that. But like, if I talk about a product, like it's actually something when you come to my home, you will see me using it, which I think is the most important piece of the whole thing is only work with advertisers that you actually believe in. Yeah.

Okay, this has been great. If anyone listening likes this format, doesn't like this format, shoot me a note, podcast at allthehacks.com. Very curious whether we should make this a more regular thing. Kevin, where can everyone go deep on everything you're working on? Yeah, awesome to be here, man. Thank you for having me. If people want to check out my stuff, kevinrose.com, got my newsletter up there. You're more the kind of optimization points and hacks guy, and I'm more of the health and wellness optimization side and definitely a little bit of finance as well. But we do have a lot of overlap.

But yeah, thanks for having me on, dude. And it's always great to be here and we should do more of these. Yeah, absolutely. Thank you so much. This has been fun. Really appreciate it. I really hope you enjoyed this episode. If you want to add any questions for the next one, please submit them at allthehacks.com slash AMA. Thank you so much for listening. Email is podcast at allthehacks.com. I will see you next week.