[00:03:02] Robert Leonard: When we’ve chatted in the past, we mostly talk about podcasting stuff and how to grow our shows and some of the just other creator type businesses that we have going on.

[00:03:11] Robert Leonard: And we haven’t really talked too much about what you’ve done in the startup world, specifically your two companies, Grove and Milk. So I want to talk about those real quick. Tell us about Grove, what the company did, how it all played out, and how you ultimately sold to Wealthfront. 

[00:03:26] Chris Hutchins: Yeah, so I had, you know, I think anyone listening, I’m on the older age of millennial, but like every time I had a conversation with someone in this cohort, this demographic, and was like, Hey, how are you feeling?

[00:03:36] Chris Hutchins: Everyone felt stressed out about money. And it was crazy that no matter how much money you had or how little money you had, everyone was stressed out about money. So I was like, how do you solve this problem? It’s not like nobody’s tried, right? Like there’s lots of startups and you know, companies and content to try to help people feel less stressed out about money.

[00:03:51] Chris Hutchins: And so I was looking for, is there anything that people that felt good about their money had done or did differently than the people who didn’t? And it felt like almost everyone I met the closest thing I could track those two groups, people that felt good and people that didn’t were that they’d gone through some type of financial planning process, which was basically looking at the life they wanted to live, how much it cost, how much they had, and like charting a path to get there.

[00:04:16] Chris Hutchins: And when they’ve gone through that process, they felt tremendously better about their finances. However, that process is a pain and it is unclear what the best path is. And so I was trying to think, okay, how do you do this? It turns out that there’s a whole designation that you can go through a curriculum to become a certified financial planner and there’s actually like very concrete steps you can go through that are well thought out about the financial planning process.

[00:04:40] Chris Hutchins: But it seemed to be all wrapped up in human financial advisors that cost thousands of dollars to work with to do this financial planning stuff. So we were like, what if we built software to make that process more efficient so that people could do financial planning for less money and. The unfortunate truth and the fortunate truth.

[00:04:57] Chris Hutchins: So the fortunate thing is it was true when we put people through that process, they spent less money and they came out the other side feeling much better about finances, whether they had a lot or a little amount of money. However, there is just no easy way to sugarcoat the process of financial planning such that people want to do it now.

[00:05:14] Chris Hutchins: You know, we met people that were really excited to do it, and then we were like, so we had a wait list early on, and so they would pay a hundred dollars to wait in line. They waited in line. We were like, it’s your turn. And they’re like, I don’t want to do it. Now. We’re like, you’ve been waiting in line. Don’t you want to do it?

[00:05:26] Chris Hutchins: They’re like, not now. We’re like, well, we’ll we can give you your a hundred dollars back. They’re no. I don’t want my a hundred dollars back. I want to do this. I just don’t want to do it now. And that process would just go on for months and months and months, and people just were never ready to get started.

[00:05:37] Chris Hutchins: And so it made acquiring customers really difficult because people never wanted to get started. We tried millions of things and then ultimately we got to this point where we realized the knowledge we had about financial planning and making it better and what we could do. Would be better served in a company that already had a different way to start building a relationship with customers because financial planning probably wasn’t the best front door for personal finance.

[00:06:02] Chris Hutchins: Similarly, I had gotten introduced to Andy Rachleff who started Wealthfront and they’d learned almost an identical lesson with a similar financial planning product that they built, which was, it’s not the best top of funnel way to get in the door, but they had an amazing investing product and a high interest cash account that was doing really well.

[00:06:20] Chris Hutchins: And so they had a different front door, and so we realized it would be a great combination to kind of work together. We brought over some of the team from Grove and we started working on what are ways that you can kind of build financial planning into a more seamless process that was actually less hands-on with humans and more built on technology and automation.

[00:06:41] Robert Leonard: So what does that look like today? What does it, what does the end result at West Front now? 

[00:06:46] Chris Hutchins: So the thing that I worked on first was called autopilot and we didn’t actually, so Wealthfront had this vision of self-driving money, but we weren’t sure what that looked like. So we spent a lot of time with customers and we realized that kind of one automation can make everything so much easier.

[00:06:58] Chris Hutchins: And two, a lot of financial planning was a little bit rules-based. So we’re like, okay, what if we just help you automate it all? How much money do you need in your, say, emergency fund? Okay, well, you could choose two to, or one to six months. You could choose whatever you want. Okay, so now I have my emergency fund goal.

[00:07:13] Chris Hutchins: What is your kind of stack rank priority of what you want to do with your money and how much do you need to pay your regular bills? So we built this product called Autopilot that would just monitor your external kind of checking account or your Wealthfront cash account. And anytime you had more money than the amount you wanted to keep, like let’s keep $8,000 in my account at all times.

[00:07:32] Chris Hutchins: We’d sweep the rest over and we would follow a series of rules of let’s make sure first we always have three months of savings in your emergency fund. And then next, let’s make sure we always max out your I r A. And then next, let’s make sure we max out the 5 29 that you’re saving for your kids. And then next, let’s save in a taxable brokerage account.

[00:07:50] Chris Hutchins: And so we just automated all in the background. There was no, let’s meet regularly. Let’s talk about what to do. It was, let’s come up with a series of best practices, have it work in the background and you can focus on other stuff. And for people who were Wealthfront customers, it was awesome for people who weren’t Wealthfront customers, just like we’d always learned it wasn’t the thing that was going to get you in the door and get you to sign up for a new product.

[00:08:11] Chris Hutchins: It’s the thing that once you’re comfortable with a financial institution, it’s going to make your experience with it so much better. 

[00:08:17] Robert Leonard: So after Grove, you did Milk. Another company, it was before?

[00:08:21] Chris Hutchins: Ofcourse my trajectory was worked at a startup, ended up joining this small company called Milk. And the idea was we had a bunch of ideas and we were just going to like try them out and see if any of them stuck and turn that into the company.

[00:08:35] Chris Hutchins: So it was a small team. There were seven of us. It was like three engineers, two designers, two kind of product, business, et cetera. And so we were all, we played around with a bunch of ideas and none of them really stuck, but we liked working on kind of things related to social. And so about a year into that company, we were like, none of the ideas we’re working on seem to be working.

[00:08:57] Chris Hutchins: And we had a great conversation with Google where they were like, we’re launching Google Plus, do you want to just come work on this? And we were like, that seems like a pretty good idea. And we sold the company to Google about a year in, on one hand success. On the other hand, failure. Like we didn’t build the thing we set out to build, but we had a good outcome.

[00:09:13] Chris Hutchins: And I ended up spending the next four years at Google. Unfortunately it didn’t work out at Google. Plus, I think they did. The stars weren’t aligning on our vision and the team’s vision and it was a very big team. And ultimately that the vision they had not saying my vision would’ve particularly done well, but nobody’s vision seemed to work out.

[00:09:30] Chris Hutchins: because I don’t think Google Plus, if it even does exist, is something anyone’s using. But I got this great opportunity to transfer within Google to Google Ventures and I spent about three and a half years doing early stage investing at Google Ventures. And I probably learned more in those three years about everything from investing to building to teams like just a, so much getting like a full crash course in early stage investing.

[00:09:57] Chris Hutchins: And it was such an awesome opportunity. 

[00:09:59] Robert Leonard: I absolutely want to dive into Google Ventures a bit, but before we do, what is with the name Milk. And the reason I ask that is because you guys were called Milk and then I’m pretty sure you know who Perry Perry is from my first million, he had his company, the Milk Road, and I’m like, what is going on with this?

[00:10:15] Robert Leonard: What is, what’s going on with Milk? And why are people naming their companies after? 

[00:10:18] Chris Hutchins: I’m honestly, if we were just, we were talking about like, what’s just a clean, simple, easy name for a studio? I don’t know where, I honestly don’t know where the idea came out of. It was just like a simple, easy, clean word.

[00:10:30] Chris Hutchins: We ended up getting the domain mi lk, which was like awesome domain, right? Like, you know, does it get much shorter than that? We saw the guy that had Milk.com and his, I don’t know if his website still says this, but he’s like, I’m interested, I would be willing to sell this for a number greater than seven figures.

[00:10:46] Chris Hutchins: You’re like, okay, well he has like one buyer at that price and it’s like the Milk lobbying association that ran all the got Milk ads. So basically like he wasn’t interested. So I don’t really know where it came from. We had this beautiful cursive font and it was just like a simple clean design, but at the end of the day, it was a studio.

[00:11:02] Chris Hutchins: And so the product we launched, the first product we launched was called Oink, and it was an app that helped you like find the best things in any city. And so Milk was really just like alphabet in terms of like a holding company name that it didn’t really matter what it was because none of the products were branded with it.

[00:11:18] Robert Leonard: Alright. So I feel better knowing that I didn’t miss any some trend or something going on. Yeah, some secret connotation. Yeah. Yeah. There’s no secret about mill. It’s just an easy, simple word. Yeah. Okay, cool. Tell me a bit more about Google Ventures. You said you learned a lot. Tell me some of the biggest things that you learned and also maybe tell us some of the successful investments you’re a part of Google Ventures.

[00:11:36] Chris Hutchins: Yeah, I learned a lot of things. So one was in my time there, we probably did about 200 early stage investments, and there were only two or three of us doing those early stage investments. So, and for every deal we did, we probably saw a hundred other pitches. So like thousands of pitches over four years, and a turn that gets thrown around in venture capitalized pattern recognition because there’s no perfect rubric.

[00:12:00] Chris Hutchins: You can’t like codify the principles of how you pick a deal. And so you almost need to learn, like you learn this pattern recognition of like, oh, these are the things that founders exhibit that create deals that we like as a company. And you kind of figure that out over time. But it’s very hard. It’s something that you almost have to learn to become an instinct than something you can just write down on paper as a set of checklists or rules.

[00:12:23] Chris Hutchins: Everyone kind of determines their own version of that. So for me, the thing that I was always really interested in at the earliest stage of startups was not the idea necessarily, because most companies end up changing their ideas significantly. So my wife was fortunate to join Lyft before it was even called Lyft.

[00:12:42] Chris Hutchins: It was a company called Zimride, and they were doing long distance ride sharing, kind of like the board that if anyone’s on the older edge of millennial, like we had in colleges in the basement, where it was like, I’m going home to spring break and I’m driving to Tucson. Does anyone want to drive home with me for spring break or Thanksgiving or Christmas?

[00:12:59] Chris Hutchins: And they were building that. But the founders were so obsessed with finding ways to make it easier for people to share rides together. It was like they were obsessed with that. And so when you meet people like that, it’s not necessarily about the specific idea they have now as much as it is about their passion and excitement for what area or industry they’re tackling.

[00:13:21] Chris Hutchins: And so one of the first deals I did was a company called Clever. And at the time they were building a product that made it easy for schools to sync their database of students with educational learning apps. And it seems so obvious that something like this would exist, but at the time, the most frequent way that like a piece of software that students had access to would know who the students were, was that the teacher for each classroom would email a list of students to the software company and they would load it in.

[00:13:53] Chris Hutchins: And the reason why is that it was so fragmented how many different student information system databases there were. There was like no clear leader with market share, so nobody did anything. When I met these guys, I was like, no, this is kind of boring. Like I’m not particularly in love with education. I have no idea how big this thing went.

[00:14:09] Chris Hutchins: But the three founders were so obsessed with making the educational world more efficient that they were going to give up at nothing to try and solve this problem. I didn’t invest because I was like, Ooh, this idea could be this big and it’s going to generate this much revenue. It was purely that and this is true of their first stage, right?

[00:14:26] Chris Hutchins: When they raised future rounds, it was very much about revenue projections and how the company is doing. But at the earliest stage, it was all about are these founders massively obsessed with this thing? And how much opportunity could the space have? Like is it a big market? Yes, educational software is a big market, but I don’t like what they were doing.

[00:14:45] Chris Hutchins: I didn’t really try to correlate what they were doing to a market size at that stage. And then the third thing, so I was cared about like, is there a big market? Like is there something they could do? How passionate are they about the thing? Can they do the thing. So like, did they have a team of people that could build the software?

[00:15:01] Chris Hutchins: Like was there an engineer on the team that could do the thing? Like that was really important to me. And then maybe did they have some traction? And if they had all four, the deal probably would’ve already been done. And if they had none, nobody would’ve done the deal, or at least no one on our team would.

[00:15:15] Chris Hutchins: And the more of those things they had, the faster I wanted to move. And ultimately they sold the company for about $500 million, which was an incredible outcome that no one would’ve expected. And you know, when we wrote a check, it was, you know, a couple million dollar company. So that was a good outcome.

[00:15:30] Chris Hutchins: And something that because of, I ended up like building a vertical of education tech as an investor, which was not something I was particularly knowledgeable about, but I had to get knowledgeable. And so then I ended up doing a lot of those deals. So that was one example of both what I looked for in a company that did well.

[00:15:45] Chris Hutchins: And then over time we just did so many deals because we were just like trying to find exciting founders doing interesting stuff and it kind of, It’s funny because I was able to be both very risk tolerant in my career, but when I look at my own particular investing portfolio, especially now that I’m not a venture capitalist at all, I was able to separate that risk tolerance from a personal and professional level.

[00:16:08] Chris Hutchins: So I think a lot of people look out at Silicon Valley and all these startups and they think, oh man, if I could have access, I would just, that’s how, why would I invest in index funds? And I’m like, I dunno, I have the access, I have the experience and like my portfolio is 90, 90 some plus percent index funds.

[00:16:21] Chris Hutchins: So I think just because I like it might seem like a sexy market, but I’m not convinced personally having been deep in it that it’s how almost anyone should be investing any meaningful amount of their money. 

[00:16:34] Robert Leonard: How does someone even get in the room to pitch Google Ventures? Like how does that work? 

[00:16:40] Chris Hutchins: We got a lot of cold emails just like, Hey, I want to talk to someone.

[00:16:43] Chris Hutchins: It’s not hard to find someone’s email address. Like one of my favorite hacks in general is if you’re looking for a job, don’t just go apply on the website, like find some way to get connected with the company. Like in many companies, there is a way to do this, and it might not be the most obvious way, you might have to guess email addresses, but between some browser extensions, there’s a browser extension called Lucia that I really like that when you’re on LinkedIn, it just tells you people’s email addresses.

[00:17:07] Chris Hutchins: You can just guess and search people’s email addresses with quotes. And there are, I would say like 50% of the people I’ve ever wanted to email have done something on the internet where they’ve had their email address published, whether they’ve posted it on Twitter, whether it’s in some PDF, like something.

[00:17:20] Chris Hutchins: So find someone’s email address and send them a note that shows how interested you are in that particular person. So when I would get an email that’s like, dear Future Investor, we would like to work with you. It’s like, eh. But when someone’s like, Hey, I saw you got, you led the round at this company and I love what they’re doing.

[00:17:38] Chris Hutchins: And I feel like for you to have spotted that means you probably have a lot of experience in Industry X and we’re building in this industry and here’s what we think we’re excited about. Could we share a little bit more about what we’re doing now? I’m interested, but the more generic it was, the more, I just think you’re kind of blasting everyone, but the reality is the deals that every VC wants to get in are like the hottest deals.

[00:18:01] Chris Hutchins: And so the more desperate the founders are for money, it’s almost like inversely correlated. So. I would say the best way to get an introduction is to get someone, another founder, who that company’s invested in, to introduce you. If you have a startup and you want to raise money, find some founder that’s raised money from an investor and get them to be like, this company’s awesome.

[00:18:19] Chris Hutchins: You should talk to them. And I think any investor will take that meeting every time. 

[00:18:23] Robert Leonard: It’s like a bank. They’ll give you a loan when you don’t need it, but not when you actually need it. It’s just the way it always works. So we talked, we spent the first quarter or so of this episode talking about what you’ve done in the past.

[00:18:35] Robert Leonard: I want to spend the rest of the episode talking about what you’re doing now and really all about the hacks and the optimization that you do. So first, before you get into that what led you to even wanting to optimize your life and specifically all the different types of points that you do, and what does it mean to be a quote unquote life hacker?

[00:18:52] Chris Hutchins: Ooh, lots of good questions. I think my general premise is there’s kind of three ways to operate, and I’m making these three ways up, but I think I’ve thought about it enough that I can make up a framework on the fly. You can either spend money to do things that you don’t and you don’t have the money and go into debt.

[00:19:08] Chris Hutchins: I’m not a big fan of that option. You can, the two options most people think is I either spend all the money to do all the things I want and I go into debt and it’s a problem or I sacrifice and I don’t spend any of the money and I don’t do any of the things I want and I don’t go into debt, but like I don’t get to do all the things I want.

[00:19:26] Chris Hutchins: I think my entire life premise is based on the fact that you can find something in the middle and that if you really like, dissect and optimize some area, and you can do this with almost any area of your life, you find a way to have the experience that’s much closer to the experience that you wish you could have a cost that’s much closer to not doing it.

[00:19:44] Chris Hutchins: And so for example, if you find the right resources and the right podcasts or blogs or whatever, you can get a lot of the information that you would otherwise need to hire, you know, an expensive concierge doctor to get. And there are also products and services out there that kinda make that easier. When I met a couple friends of mine that had a lot more money than me, they were like, oh, I’ve got this awesome doctor and I pay tens of thousands of dollars a year, and they do all these diagnostics, and like, I feel like I know so much more about my health.

[00:20:13] Chris Hutchins: And I was like, I want that. I was like, how much is that? And so I was like, well, the one I use like $50,000 a year, I’m like, okay, well I’m not, there’s no chance on Earth I’m paying $50,000 a year to have a doctor. Like I have insurance. So like my doctor should be like a $20 copay. So like we’re off by like multiple orders of magnitude.

[00:20:30] Chris Hutchins: But I was like, okay, what are they doing? And they were like, oh, here’s a list of stuff. And if you start googling around, you’re like, oh, these are the kinds of health diagnostics that people do. Who have these doctors do? Some of them are even covered by insurance. So like you can take that into your own hands and you can go pick up the right book or listen to the right podcast to understand a little bit more about those things and use services online that do biomarker analysis and all that kind of stuff.

[00:20:52] Chris Hutchins: And now all of a sudden you’re getting that experience for a fraction of the cost. So that’s an example. In health, I feel like I’m probably more well known for in the travel world. It’s like, do I want to fly on like a nice bed when I’m crossing the ocean on a 10 hour flight? Absolutely. Like, do I want someone bringing me like a nice meal and like, you know, whatever.

[00:21:11] Chris Hutchins: Of course. Who doesn’t want to fly business class at first class around the world? Am I ever going to spend five to $10,000 for a 10 hour flight? No. That’s to me and my personal financial situation, that’s crazy. Like if it were up to me, I would never spend that amount of money and it is up to me. So I don’t think I’ve ever spent a thousand dollars or more on a flight.

[00:21:30] Chris Hutchins: But if you play the points game and you optimize it in the right way, you can get that business class flight for a fraction of what it normally would’ve costed, and in some cases, less than you would’ve paid if you paid out of pocket for the coach flight. And so I think I’ve dedicated a lot of time because I really enjoy traveling to finding a way to have the five star luxury travel experience at the kind of, I dunno, maybe two or three star backpack re price.

[00:22:00] Chris Hutchins: And maybe it’s a little bit more than the, you know, a hostile, but like you’re able to find ways to get that experience for much less. And that’s what I’ve kind of focused on, is how do I do the research and dig in to find all the tools, the tips, the strategies, the tactics, to have those experiences for less.

[00:22:16] Chris Hutchins: Because I want to live like that amazing life. I just don’t want to pay the money to do it. 

[00:22:20] Robert Leonard: People like Dave Ramsey as an example, say that credit cards shouldn’t be used at all regardless of the points. And then other people say that credit card users spend more because they’re using credit cards than they would if they had paid in cash, which basically negates or webs away any benefit that you’re receiving from those credit card points.

[00:22:38] Robert Leonard: I personally use credit cards for everything. Every single purchase I use a credit card. I don’t think I’ve ever even used the debit card I have. I very rarely ever use cash, and I’ve never spent a penny on interest. So I never carry a balance. So I feel like I keep it in control, but I could see it being true that I maybe spend more money because I’m using a credit card, not cash.

[00:22:57] Robert Leonard: because the few times it’s rare, but the few times that I do have to use cash. It kind of hurts. Like it doesn’t really hurt. It’s just like, oh man. Like, I don’t know, it just feels different than when I’m using my card, either entering it online or even just entering the chip at a store. So I think I could be potentially spending more money just because I’m using a credit card and maybe that’s even offsetting the amount of points I get, even though I probably get thousands and thousands of dollars a year in points.

[00:23:21] Robert Leonard: So, yeah. I’m curious how you kind of balance these ideas and I know you obviously think it’s worthwhile, but why do you think it’s worthwhile? 

[00:23:29] Chris Hutchins: Well, first off, if anyone has any high interest debt and I’ll, I don’t know what the right threshold is now in this high interest rate environment, but I’d, let’s say like over 8%.

[00:23:37] Chris Hutchins: Normally I’d say like over 5%, but now that mortgages are kind of tipping over 7%, say more than 8%. So if you’re carrying a credit card balance, if you have a really high interest car loan or a title loan or anything like that, this is not for you. Like you are never going to earn credit card rewards that make it worth that debt.

[00:23:54] Chris Hutchins: So step one, I’m sure there is another episode of this podcast that would be an incredible listen, and you could put a link in the show notes about how to think about debt, how to get on a payoff strategy and build your credit and all that. That’s more important. Now, let’s say you’re past that, and so for Dave Ramsey, maybe his audience is entirely filled with people that given access to unlimited amounts of spending beyond their means.

[00:24:15] Chris Hutchins: They will just do it. And if you’re the kind of person that would spend more money with a credit card, yeah, it’s not a good fit for you. Like that’s just clear. But if you’re the kind of person who isn’t going to spend a lot more money, like if you’re going out to dinner, whether you pay with cash or your credit card, If the fact that you have the credit card in your wallet means you’re going to order three times as much or a nice bottle of wine, you should pay with cash because the points aren’t going to make up for that.

[00:24:37] Chris Hutchins: Like the point value is like at max maybe a 10% return. And if you’re not that optimized, maybe it’s a 2% return. So like the window is two to 10% back. So if you’re going to spend 20% more bad deal, if you’re going to spend 1% more, probably a good deal. And you could probably a AB test this like why don’t you take a month and just spend cash?

[00:24:58] Chris Hutchins: You might find that there are a lot of things that are very hard to pay with cash. Like maybe use your debit card. I don’t know if that’ll burn as much, but like you could try to test this and be like, am I actually spending more when I have a credit card for me? I don’t think I am. because I’m just making this decision of do I want the thing or not?

[00:25:13] Chris Hutchins: Or do I need the thing or not? And then paying for it. And like for me, I’ve never felt the burn of using cash. If anything, I feel the burn of using cash is actually that I like tracking my spending. So I do it all in Copilot. And with cash is just so hard. With a credit card, I can actually see where I’m spending money.

[00:25:29] Chris Hutchins: So I could actually make a case that because it’s so easy for me to track my spending using a lot of different apps, I personally use Copilot. Like by using a credit card, I’m able to track my spending and see where the money’s going. And I can’t remember the stat. So I just started, I have working with Copilot because I reached out to them.

[00:25:47] Chris Hutchins: I was like, I love your product. Can we work together? Can we come up with a deal for my audience? So if you go to all the hacks.com/deals, by the time you hear that, hopefully we’ll have a good deal for Copilot and I love it. But I think they found that people save some meaningful amount, like more than 10% of their spending get, their spending gets reduced by more than 10% just by tracking it.

[00:26:08] Chris Hutchins: And I could tell you that tracking your spending if you’re still using cash is so much harder that I imagine most people listening won’t do. For however much more you might spend by using a credit card. I wonder if that’s negated by the fact that if you track your spending, it’s so much easier to do with a credit card because your transactions could get imported automatically versus you manually needing to type in, how much money did I spend with cash?

[00:26:28] Chris Hutchins: How much money did I spend here? I guess you could still do that with a debit card, but I don’t know, like most of the studies I’ve seen comparing credit card to cash is actually like physical green dollar cash. So for me, I don’t think that I’m spending more by using a credit card, but I am getting two to 10% back when I use that credit card.

[00:26:47] Chris Hutchins: So it’s a no brainer. Like, and the difference between two and 10% isn’t just picking a card that aligns with your spending, which is part of it, right? If you spend all your money on dining and groceries, well there’s cards that earn four points per dollar on dining, and so like that is probably the card you should use.

[00:27:04] Chris Hutchins: If you spend all of your money on travel, there are cards that earn three points per dollar on travel, or if it’s all on flights, five points per dollar on flights. Like you can pick a card that aligns best with where you spend your money and that’ll maximize your return. And then the second piece is using those points in a way that gets the most value.

[00:27:23] Chris Hutchins: And so if you have a million points on Chase and you decide to get gift cards with those points, you’re probably going to get a fraction of the value as if you wanted to use those points for travel. And so you might get two, three times as much using them to get travel by booking in the travel portal on Chase’s website, but you might get another two to three times more points if you take those points and transfer them to an airline or a hotel group like Hyatt or United and book directly with those airline and hotels.

[00:27:53] Chris Hutchins: And then you might be getting, gosh, I’ve had instances where each point’s worth 10 cents. Let’s take an example of you have a card that earns three points per dollar on dining and you’re able to get 10 cents per point out of the value. That’s like 30% cash back every time you go out to eat, which is pretty cool.

[00:28:09] Chris Hutchins: Now those 10% examples are few and far between, and I think you could make a case that had I not had those points, I wasn’t going to stay at the hotel that would’ve otherwise cost $1,800 a night. You know, maybe they’re not really worth that much. If we’re being like totally honest, then I’ll be totally honest.

[00:28:25] Chris Hutchins: Like, I’m not going to spend $1,800 a night. So are they worth that? No, but they’re certainly worth more than I would’ve gotten buying a gift card with my points. Buy a huge margin. 

[00:28:35] Robert Leonard: There’s a lot there that I want to talk about, but first, why Copilot? And I think it’s funny you mentioned that because I didn’t know that you used them.

[00:28:42] Robert Leonard: I downloaded their app, I don’t know, a couple months ago, maybe. Maybe even longer, maybe last year. It’s been a while. I didn’t love it. It was hard for me to get into it. So I’m curious, what am I missing? I use Mint right now. I really like Mint a lot. It’s free, super easy to use and I can do a lot of things that I need to do with it.

[00:28:59] Robert Leonard: So I’m curious. I’m always looking for something better though. So why Copilot? 

[00:29:03] Chris Hutchins: So there’s a lot of options and when I wanted to decide what to use, I used Rocket Money, Monarch Money, Mint, Tiller HQ and Copilot. So I tried all of those. Are there other ones I should have tried? I’m sure someone listening has ano Oh and Yap.

[00:29:18] Chris Hutchins: I tried Yap. The like the tried and true thing. So for me there’s kind of two styles of budgeting, if you will. And I hate the word budgeting because I’m not budgeting as much as I am spending tracking. One is budgeting, right? I want to say this is how much I’m going to spend in a category and I want to really hold myself to it.

[00:29:35] Chris Hutchins: My style is more I want to understand where I’m spending money and I’m pretty good if I feel like I’m spending too much at course correcting next month. So I don’t really need to set a budget per se to say I only want to spend $300 this month on going out to eat. I want to say, how much am I spending going out to eat?

[00:29:53] Chris Hutchins: Do I need to ratchet it back? So why NAB is really good if you’re the kind of person that wants to set budgets and try to stick within them. That was not me. Why NAB wasn’t the right product amongst all the other ones. I put a high value in my world at products that just like look beautiful, like I like des well designed products.

[00:30:12] Chris Hutchins: I have an iPhone, like I enjoy Apple’s design. And I think that Mint for as much as it has many features, is filled with like, go get this ad go get this thing ad like get, there’s just lots of ads. All the monetization of the product is ad supported and it just, it’s like so overwhelming. And the ease at which you can customize things was not as simplistic.

[00:30:38] Chris Hutchins: So like, Hey, every time there’s another transaction with this name, do this thing. And it just kind of happens Automagically. So Mint was just like a little bit frustrating and like the UI of like looking at how your spending was happening wasn’t great for me. Monarch Rocket Money were similar in that I just felt like they were slightly less easy to use.

[00:30:57] Chris Hutchins: And I’m a crazy person when it comes to this. So I actually went back and imported 18 months of transaction history to Mint, like to all six of these apps and went through and like recategorized every transaction in every single app. And so if you listen to my show on All the Hacks, like that’s the kind of thing that I do.

[00:31:15] Chris Hutchins: I’m like, I’m going to spend 40 hours testing out eight budgeting apps to try to figure out which one I think makes the most sense for me. And if you’re like me, you might like a certain one. And I’ll tell you what I thought that Rocket money was the best option. If you don’t want to pay a subscription.

[00:31:30] Chris Hutchins: When it comes to something that’s a combo of like easy and has enough automation to kind of do things quickly for you, but also had enough flexibility that you could create your own categories and, you know, kind of design it in a little differently way. So that was my favorite free one. And then, but Copilot was a better budgeting, spending tracking app for me, and I love that I could just pull it up and look at categories, look at them over time see all the recurring transactions I have going on, see where I’m spending the most, see where I’m on track on a month by month basis.

[00:32:04] Chris Hutchins: Looks like this month I’m way over. I’m trending to have July be a huge month. because my wife and I just took a really big, expensive vacation. And so, I don’t know, I’ve never been as excited to track my spending as I have the last like six, seven months using Copilot. Like I’m opening up every day and it’s really easy to categorize a transaction.

[00:32:23] Chris Hutchins: I felt like Mint to pull out your phone and see if I had any transactions in the last couple days and like categorize them in two seconds, just felt like a lot of work. And the Copilot is just like, just so easy. And they have a couple cool things like they’ll sync with Amazon and pull in your purchases so that when you’re looking at your transaction on Amazon and you’re like, God, what was this?

[00:32:42] Chris Hutchins: How do I categorize this? Was this home? Was this Kids? They’ll just show you the purchases you made. And same thing with Venmo. They’ll like, there’s a way to integrate Venmo such that you actually see what it was. It’s not just a Venmo charge. So it’s a little easier to categorize stuff. I dunno, that’s a few of the reasons I like it and everyone should know, like, like I said, full disclosure, I am now working with them like they’re a partner of the podcast.

[00:33:03] Chris Hutchins: But it all started the way almost every one of my sponsors in the podcast has, which is I love this product. Like right now, unintentionally, I’m wearing two articles of like my Pants and my shirt are both Vori. So I was like, I love Vori. I already own them all. I wear them all the time. Can I partner with this brand?

[00:33:20] Chris Hutchins: And so I’m regularly doing that for my partners. It’s just like partnering with brands that I already use. So, but full disclosure. 

[00:33:28] Robert Leonard: Yeah, maybe I’ll have to give a Copilot another try. I literally just this morning was working on my mint budget. Not really budgeting. I’m kind of in the same spot as you.

[00:33:35] Robert Leonard: I don’t really do the budgeting, but just kind of tracking my spending, seeing where it’s going. And I had a couple Amazon charges and I didn’t know what they were, I didn’t remember. So I had to open Amazon in a, my other bra, my, not my other browser, my other screen and just had to enter it in because I didn’t remember what it was.

[00:33:49] Robert Leonard: So that might be a cool feature of pilot for me to try out. 

[00:33:52] Chris Hutchins: Quick thing though, for you and anyone that does any type of budgeting and an expense tracking on Amazon, if you go to Amazon and you hover over the accounts thing and you click your account and you click account and you scroll down on the left, there’s a link to something called your transactions.

[00:34:07] Chris Hutchins: And instead of ordering everything by orders, it orders it by every charge that’s hit your credit card. That’s super annoying too, how they split it up. Yeah, so sometimes it’s hard because you’re like, ah, Amazon hit my card for $23, and you go in, you’re like, I haven’t ordered anything that’s $23. It’s like, oh, well I ordered this thing where half of it shipped, so they charge my card differently.

[00:34:28] Chris Hutchins: When you go to the your transactions page, it just shows you like, charge for $5, charge for 34 72, charge for 31 93, and then when you can link out to the order and find it. So I’ll say whether you’re using y a or just a spreadsheet or anything, if you are trying to figure out and categorize what you spent money on Amazon, find the transactions page, it’s so much easier than the orders page.

[00:34:51] Robert Leonard: Yeah, that’s a good hack. I am going to have to do that because that is always a problem for me. I’ll buy like four or five things and then two will be in, in one order and three will be in the other and one will be in, like, it never adds up. So I’m definitely going to have to do that. I didn’t know that was there.

[00:35:03] Robert Leonard: Getting back to the credit card points for someone who uses credit cards, they’re interested in it. They’ve kind of maybe always wanted to do more with their credit card points, but they’ve just never spent any time on it. Where do they get started? Give us the 101 version of getting started with optimizing credit card rewards.

[00:35:19] Chris Hutchins: I’ll give the two part. The op, the 101 for earning and the 101 for redeeming. So 101 for earning is look at where you spend money and it doesn’t I feel like some people think this has to be a science. You don’t have to go use Mint or Copilot and be like, did I spend $3,008 on dining over the last three months or was it 3010?

[00:35:35] Chris Hutchins: No, like roughly. And most credit cards will give you an annual spending report where you could just like download the spending report from Amex or Chase at the end of the year and be like, where did I spend money? Look at where you spend money. You probably already know this answer and think, okay, let’s try to get a card that aligns with where I spend money.

[00:35:54] Chris Hutchins: And that’s my primary card. I will say I did an incredible amount of. I don’t dunno, analysis is the right word. So I built this spreadsheet that had the top, I dunno, 20, 30 cards in it. And if you want it, you can go to allthehacks.com/card value and you can get it for as little as a dollar. And I, you basically check a number of cards and put in how much money you spend in different categories and it’ll tell you how many on average points you’re earning.

[00:36:19] Chris Hutchins: So if you spend all your money on dining and you get a 1% cash back card, you’re going to get 1% back. But if you get a card that has points on dining, you’re going to get more. What I found, which kind of is counter to what I do personally, is that you get a ton of value with your first and second card, and once you get a third credit card, you’re not really adding that much extra value in terms of like optimization and more earning.

[00:36:43] Chris Hutchins: So getting the right two card combo is really valuable. 3, 4, 5, 6, 7, 8, 9, 10. You’re really diminishing returns. So it’s finding the one or two cards that are going to most align with your spending. And the only exception I’ll give there is if you have rent, the Built card is just like, I would almost go as far as to say must have because it’s the only card out there that lets you earn points on rent and you don’t have to pay a fee to do that.

[00:37:08] Chris Hutchins: So up to a hundred thousand dollars of rent a year, you can earn a hundred thousand points highly. They’re not a partner of mine, they don’t pay me any money. But if you go to all the hacks.com/built, it’s my referral link and I would love you to do that. But I think that’s the one exception is like there’s a two card combo and then if you have rent and you want to add a built card or make it your primary card, highly recommend.

[00:37:29] Chris Hutchins: That’s the earning side. Then on the redeeming side, I think you have two options. You say, I don’t really want to go deep down this rabbit hole, and you redeem your points in the portal, like go to the Chase travel portal, redeem points, and you’re going to get somewhere between one and one and a half cents per point.

[00:37:47] Chris Hutchins: And is it the best possible use of your points? No. Is it really easy to do? Yes. If you want to go a little bit further, you get a tremendous amount of value by having what I’ll call flexible points, which is chase points, Amex points, capital One points, city points or built points. And they’re flexible in that they’re able to be used lots of places you could transfer them to different airlines all over the world.

[00:38:12] Chris Hutchins: So I’ve gotten tremendous value transferring points to Air France and not because I’m necessarily going to France, but Air France is a partner with KLM. They’re part of the same mileage program. So if you’re going to Amsterdam but you can also book flights using Air France points on any of the Sky Team airlines.

[00:38:29] Chris Hutchins: So Delta and other things, British Airways there. I’ve gotten some great deals booking flights within the US on American Airlines using British Airways points. I get a ton of value transferring points to other airlines. A really concrete example was I was trying to go down to San Diego, which is like normally a cheap flight from San Francisco, but for whatever reason it was like $250 and it was pretty last minute.

[00:38:51] Chris Hutchins: I transferred some points to Avianca, which is a, you know, Latin American airline. I think you’re based in Colombia. And I got the flight for 6,000 points. Like if I were to book a flight in the portal, 6,000 points is going to get me like 60 to $90, but the flight was almost $300. So finding the right way to do this point, transferring stuff takes a little bit of effort and results in a tremendous amount of benefit.

[00:39:17] Chris Hutchins: And so there are a lot of tools that help make it easier. There’s a tool called Point Me that makes it easy to search for award flights and there’s a tool called Seats Arrow. I’m going to do an episode soon about like all the tools and how they all work and what the pros and cons of each of them. But there are a bunch of these different tools.

[00:39:34] Chris Hutchins: If you search, award search tools is kind of the industry term, you’ll find them. Seat Spy is another one that focuses on one route at a time, gives you a year of availability. But if you play around with these tools, you can find really great deals. And so I’d say that’s the answer. And if you really want to, you know, if you’re on the higher end of the points earning spectrum, there are services where you could just pay someone.

[00:39:56] Chris Hutchins: It usually costs about $150 per person to maybe $200 and they’ll just do it all for you. And so I think at sometimes you’re like, why would I pay someone that sounds crazy? And you’re like, okay, well how much is like six hours of my time worth? And if I’m not going to, if I’m otherwise not going to get this much value, is it worth it?

[00:40:12] Chris Hutchins: And usually you only have to pay like $25 and then the rest only if they find something. If you’re really excited to take your honeymoon and you want to fly in business class to Europe and those tickets are 10 grand for two people and someone can get them for you for the points equivalent of a thousand dollars and you gotta pay them $300 to find those flights for you for two people, yeah, it’s actually like a lot better deal.

[00:40:33] Chris Hutchins: I think sometimes we get caught up in like paying other people for time, but at some point I think we all cross this threshold where we’re like, oh my time is valuable and if this person can save me a lot of it or do it better than me and save me money in the process, it’s worth it. So I think you have a lot of options.

[00:40:48] Chris Hutchins: But I think learning how to get value out of transferring points to airlines and hotel groups is where you go from unlocking some value to unlocking a lot of value, but just using the right card is going to unlock a ton of value. 

[00:41:02] Robert Leonard: Yeah, I think that’s where I need the most work, is learning how to transfer between things and we’re going to talk about a couple more situations, but also for anybody listening, I know Chris is mentioning a lot of like really great resources from personal finance tools and resources, his own resources to a bunch you just mentioned in that response.

[00:41:18] Robert Leonard: So I’ll make sure I put all those in the show notes for everybody listening. And also, just to clarify the seats.aero is dot A E R O, not A R O W, which I spelled it wrong the first time. So again, I’ll put all this in the show notes for everybody, but just wanted to clarify that. Now, is there anything better than Southwest Companion Pass?

[00:41:35] Robert Leonard: Is there anything better than that? And we can dive into more specifics of my situation if we need to. But I’m just curious, generally speaking, is there anything better than the Southwest Companion Pass? And for people who don’t know what that is, maybe explain quickly What that is. 

[00:41:48] Chris Hutchins: Yeah, so Southwest, almost every airline has some type of, you know, kind of like elite status program.

[00:41:54] Chris Hutchins: You fly enough on the airline and you get different tiers, and they’re often like silver and gold and diamond, and platinum, and Southwest is a little different in every possible way. The primary way that they’re the most different is if you go to any search other than southwest.com. You can’t find Southwest prices.

[00:42:10] Chris Hutchins: So if you’re new to the travel hacking game, I would, or even just saving money on travel Game one, I think Google Flights is the best place to search for flight prices, but two, Southwest never shows up on Google flights. The flights do, but the prices don’t. Unfortunately, you probably always need to do two searches.

[00:42:26] Chris Hutchins: It’s like Google Flights and then Southwest. But Southwest has a-list, a-list preferred, which are their kind of tiers of status. And then the third one, and I think now it’s 135,000 points a year, you get what’s called companion pass. And with companion Pass, you can nominate one person and you can actually change it three times a year.

[00:42:44] Chris Hutchins: And that person flies for free. Anytime you buy a ticket and you don’t even have to buy the ticket. If you use your points to buy a ticket, they can still fly free. You just pay taxes and fees, which on most domestic flights, it’s like $5 and 60 cents. If you have a partner and you guys want to travel a ton domestically, Mexico, Caribbean, Hawaii Southwest Network isn’t too international, outside of kind of North America, Caribbean.

[00:43:10] Chris Hutchins: But every single flight you take, someone gets to come for free. It’s incredible. And like, if you want to do that and then on the summer you know your spouse is tied up with work, you want to travel with a friend, you can nominate, switch it to the friend, travel with them for a few months and switch it back to your spouse.

[00:43:25] Chris Hutchins: Like it’s an incredible thing. The extra incredible thing is that almost every single elite program makes it very difficult to earn their status without flying. Southwest is a rare exception where you can earn companion pass just from the points you get from a credit card, including the points you get from a signup bonus on a credit card.

[00:43:46] Chris Hutchins: So if you need 135,000, you might have to spend $135,000 on a credit card. But if you open up a credit card at a time where Southwest has a 60,000 point signup bonus, and by the way, if you open up two Southwest credit cards at that time, you’re already off to the races. If you hit those two welcome bonuses, you’re at 120,000 points.

[00:44:07] Chris Hutchins: Chances are those credit cards had a thing that was like, you know, spend $5,000 in the first 90 days and get this bonus between the points you’re going to get from that spending and the welcome bonus. You might already be there. I think within the industry, the way to hack companion pass, and by the way, whatever you earn it, You get it for the rest of that year and the next year.

[00:44:27] Chris Hutchins: So the real hack is get the card in like December, spend some money on it, but make sure you don’t spend enough to hit that welcome bonus until January. January statement closes. You get those welcome bonuses posted. Now you’ve got it for the rest of that year and the next year. So if you’re thinking about this coming into 2024, make sure you know you could open a personal card and a business card and all of a sudden by January, 2024, you spend the welcome bonuses.

[00:44:58] Chris Hutchins: You get there. You’ve got two years of BRI nominating someone to fly anywhere you fly for free. It’s absolutely amazing. And so a people will do for two years and then if partner switch. One or two Southwest cards get that welcome bonus. Then they’ll do it for two years. Now, four years later, maybe the first partner’s now downgraded or closed their Southwest card.

[00:45:20] Chris Hutchins: They do it again. And I know people that for, you know, the better part of eight years have been cycling between their partner to have companion past for eight years. So the short answer is, if you’re in a relationship, you don’t have kids where you know, if you want to do kids, you and your partner could do at the same time, nominate your kids.

[00:45:36] Chris Hutchins: Like, but no, there’s not much better than companion Pass. I think I’ve done it twice. And so we’ve had it for probably four years and it’s great. I think that is an ultimate hack if you want to travel in North America. But if your goal is I want to go to Europe or Asia, it’s not, you know, it’s not going to help you much there.

[00:45:58] Robert Leonard: So this is my second time with the companion pass. The first time I earned it, it was totally by mistake. I didn’t know anything about really credit card points. I knew I was like earning some cash back, but I didn’t really know, I wasn’t optimizing like you, you’re talking about here. I opened a credit card with the rewards bonus, so I got like 80,000 I think points like maybe in May-ish.

[00:46:16] Robert Leonard: And then, so I earned it like later that year. And so I think I earned it in September or something. So I got it for that year and then the following year and I realized, okay, well now that I get it for a year and a half, I, next time I do this, I can do it well or properly. And so now I earned it in January or February of this year, and I have, so I have it until December of next year.

[00:46:34] Robert Leonard: And I fly about 50 times a year with my girlfriend and we fly only in the US so we fly companion pass. And so we fly almost 50, 52 weeks a year. And we do that by one, get one free. And so I didn’t think there was going to be anything better than that. But I had to ask because like I said, I fly a lot, but I’ve never flown first class until like two weeks ago.

[00:46:55] Robert Leonard: I flew first class for the first time ever. The only reason I did it was because I had bought like a normal general admission ticket or coach or whatever you want to call it, and they upgraded when I was doing checkout. They’re like, okay, upgrade to first class for $47. And I was like, yep, done. I will absolutely do that.

[00:47:12] Robert Leonard: So I did it. And the downside there though is now I feel spoiled and I’m like, oh my god. First class, even though it was a pretty short flight, I was like, oh my God, first class is awesome. So much better than any seat on Southwest. And so I’m like, ki I was like kind of hoping that there was a way that I could still use a non Southwest rewards system to get something equivalent to the Southwest companion pass.

[00:47:33] Robert Leonard: But given that I get 50 ish flights a year, buy one, get one free, I figured there’s probably nothing better than that. 

[00:47:39] Chris Hutchins: No, I think the best option for you is just make sure you’re diversifying your points so you have some points in a program like Chase or Amex or Citi or Capital One or built, and then save that business class for when it really matters.

[00:47:52] Chris Hutchins: If you’re going we took a trip last December and we went to London and Paris and it was me, my wife, two kids, and we have an au pair from Spain and the five of us are going to Europe. And it was like, let’s drop all of our points. Not all, but we dropped about 420,000 points and we all did business.

[00:48:10] Chris Hutchins: And it was like everyone got to sleep a little bit on the plane and one of the baby, one of the kids was only like six months, so we only needed four tickets. But it was amazing and it just like made the whole travel experience so much better versus if I’m flying business class to LA it’s like, yeah, it’s like, it feels nice and, but it’s like save it for when it really matters.

[00:48:31] Chris Hutchins: And by the way, I was looking right now on Southwest. The personal cards right now are at about 50,000 point welcome bonus, but the business cards are at 80, and then the, it’s not a cheap card. The Rapid Rewards Premier Business card right now is at 120,000 points. Now, granted, you’ve gotta spend $15,000 in nine months, but if you started using that this year and just hit that nine month mark in January, hit that 15,000 mark in January, you’d get 120,000 points.

[00:49:00] Chris Hutchins: Now, caveat, I stand corrected reading this. After you spend 3000, you get the first 60, and then after you spend the next 12,000, you get another 60. So you want to make sure you don’t get that first 60 in one year. So maybe ho, maybe hold off or wait until you, you can hit it. But that’s a huge way to get there quickly, right?

[00:49:18] Chris Hutchins: 120,000 points from the card. You gotta spend 15,000 to get it. You’re already going to be at 135 by the time you’re done. And a couple hacks here. If you’re trying to earn a welcome bonus, whether it’s Southwest or Chase, or anything, I have too.

[00:49:32] Chris Hutchins: I’m not an advocate of, Ooh, I need to hit this bonus. Let’s go spend money. I don’t need to spend. That is not what you want to do in this circumstance, but some things that you can do if you’re trying to hit the minimum spend to get a welcome bonus without spending more money. A favorite of mine is just buying gift cards for things you know you need, assuming you can support it with your cash flow.

[00:49:52] Chris Hutchins: If you shop a lot at Whole Foods, you can go to Whole Foods and you could buy Whole Foods gift cards. So if you know you spend $500 a month on groceries, you could potentially buy four, $500 gift cards for the next four months. You buy all your groceries on Whole Foods gift cards, but you’re able to front load $2,000 on your card.

[00:50:08] Chris Hutchins: Now, if you spend a lot of money on Amazon, you could do the same thing. So I would say one way to kind of front load your spending is to go prepay for things on gift cards that you know you’re going to spend. Don’t go buy a thousand dollars Home Depot gift card if you don’t have a thousand dollars Home Depot purchase coming.

[00:50:24] Chris Hutchins: Like, don’t do that, but that’s an option. I’m not ever a fan of paying fees to put money, anything on your credit card. You know, like if you gotta pay 3% fee to send your friend money on Venmo, I don’t think it’s ever worth getting those fees. But if you’re towards the end of a welcome bonus and you’re not going to hit it, it probably is.

[00:50:42] Chris Hutchins: So if you’re like, in this case, it’s like if you spent 15,000, you get 60,000 points and you’re at 14,500 and there’s nothing you need, like maybe send your partner 500 bucks, pay the 3% fee, which is only going to be like $15, and make sure you get your 60,000 points absent. You’re on the cusp of getting a bonus, not a fan of paying fees.

[00:51:02] Chris Hutchins: So that’s one. And then on the business card side, I think a lot of people think in order to get a business credit card, you need to be running a company with employees and all this stuff. And that’s not true. You do need to have a business, but a business can also mean a sole proprietorship, which means you’re not, you don’t have a tax ID number for the business.

[00:51:21] Chris Hutchins: It’s not necessarily a legal entity. It could be I drive for Uber every now and then, or I sell stuff on Etsy, or I have a blog and I don’t monetize it yet, but one day, you know, one day I want to monetize my blog or I want to monetize my social media account. Like anything that could be a business that you’re starting to work on now would qualify if you tutor someone, if you consult on the side, if you do some freelance work, a lot of times business cards have tremendously larger welcome bonuses and could help accelerate points of earning very quickly, and you can sign up for them with your own social security number.

[00:51:58] Chris Hutchins: You don’t have to have a business tax id. And so I would just say, look into that. If there’s anything you have in your life that could potentially kind of fit the mold of business income or future business income, because I’m looking, it’s like Southwest Card. The personal ones are all 50,000 points and the business ones go up to 120,000 points.

[00:52:19] Chris Hutchins: There are a lot of Chase cards that are 50,000 point for personal. And then you go to the business side and, you know, some of them are a hundred thousand points. So you can really accelerate points earning with welcome bonuses. And you can also accelerate it with business cards. So I have a list of all the cards in all their bonuses now@allthehacks.com slash cards if people are interested.

[00:52:40] Chris Hutchins: The links on, there are links that are partner links, so obviously you’ll be supporting the show, but just know in advance. But there are a lot of cards there and, you know, all the bonuses there as well. 

[00:52:51] Robert Leonard: One other thing I love about the Southwest Card is that it’s with Chase. I have cards with Barclays, South American Express, capital One.

[00:52:58] Robert Leonard: And for me personally, I like Chase the best. I just, they’re just my personal favorites, so I love that the Southwest cards threw them as well. 

[00:53:05] Chris Hutchins: I used to say that. I used to say that. 

[00:53:07] Robert Leonard: Why? To change. 

[00:53:08] Chris Hutchins: I got a Capital One card. 

[00:53:10] Robert Leonard: I hate it.

[00:53:10] Chris Hutchins: And it’s so good. 

[00:53:12] Robert Leonard: You know why I hate it? I can’t pay ahead the balance.

[00:53:15] Robert Leonard: So if I charge 50 bucks on the credit card and I go to try to pay it on capital, like it’s pending as 50 bucks, I can’t go to Capital One and pay 50 bucks. If I do that on Chase, I can pay anything that’s pending because it recognizes that as a charge already. And that drives me nuts with every, the only place I’ve been able to do it is Chase and that’s why they’re my favorite.

[00:53:36] Chris Hutchins: So for me, I’m like, I don’t want to pay the card off before the statement’s due because it’s like a free 30 day loan. But the few things that Capital One started doing that are really impressive. And so I have a Venture X card when I did my analysis of the two cards that for the average American spending pattern get you the highest return, it was the Amex Gold and the Venture X.

[00:53:56] Chris Hutchins: Amex Gold’s four x dining and groceries, and Venture X is two x on everything simple. There’s no like secret categories, just everything is two x and. I was playing around on the Venture X site. So one thing, they have a browser extension that anytime you’re checking out, they’ll create a virtual card for you and you could put that virtual card in and then set it to auto lock.

[00:54:20] Chris Hutchins: So if you’re buying something on some website that you’re like, I don’t really know about this website, you could buy it with a virtual card that’s not your regular card number. Set it to auto lock the next day. And know that if someone ever were to get the credit card number that you paid for that transaction with, it would never work again.

[00:54:34] Chris Hutchins: Or if you’re signing up for like a seven day trial, you could put a virtual card in there, lock it the next day, and know that if you forget to cancel that trial, they’re not going to be able to charge your credit card. So that feature is so easy to use on Capital One. I know a couple other banks and issuers have it, but it’s just, it’s not as easy.

[00:54:51] Chris Hutchins: The second one, my wife got this email and it was like, Hey, We’ve noticed you got two charges for the same thing. Is this correct? She clicked a link in the email and within 30 seconds they disputed and refunded the charge. Like it wasn’t, it didn’t require her to go look at her statement. They noticed it reached out to her and fixed it all automatically, which was awesome to see.

[00:55:14] Chris Hutchins: There’s a handful of things like that where I feel like Capital One is just really pushing the envelope on what you can do with software and technology when it comes to a credit card, and I just really love it. I just hope everyone follows suit. Where I don’t like Southwest is that they only let all these budgeting tools like Copilot and Mint import 90 days of history.

[00:55:32] Chris Hutchins: So unlike Chase, everyone will pull in a year of history if you’re going to go try out Copilot or Mint or any of those apps. You’re going to get a full year of transactions that can really just make it easy to go back and see how you were spending. And Southwest is only going to give you, or Capital One is only going to give you 90 days.

[00:55:48] Chris Hutchins: So you can go into Capital One’s website and export a year of history if you have a Capital One card. But you can only pull in automatically 90 days of history, which is frustrating. 

[00:55:57] Robert Leonard: It’s funny, we both have these small things that like really, neither of them are big. Like my thing, being able to pay it right away is not really that big of a deal.

[00:56:03] Robert Leonard: I could just wait till the transaction posts, it’s a couple days and then I could pay it. Like it’s not really a big deal. Your stuff’s not really that big of a deal either. But we both have our preferences, so that’s kind of funny. Do you know on the Southwest cards they have, if I remember correctly, three I believe Southwest Personal Cards?

[00:56:21] Robert Leonard: Do you know, can you only earn that intro bonus one time? So like, let’s say, could you get all three cards and earn the bonuses three different times, or can you only earn it one time? 

[00:56:30] Chris Hutchins: I mean, you definitely can’t usually open up a card if you already have the card. 

[00:56:36] Robert Leonard: Well they have three different ones. So like they have a priority card, a premier and a plus.

[00:56:40] Robert Leonard: Like if I already have priority, can I open the Plus and still get the bonus? 

[00:56:44] Chris Hutchins: Yeah, you can definitely do that. A lot of people’s strategy is to open two cards and get South Companion Pass. I would need to do some homework. I know you could definitely have multiple cards because that’s what I did. But I don’t know if you could do two personal, I know you could do a personal and business, you can even do it maybe on the same day.

[00:56:59] Robert Leonard: I’ve done the personal and business, but that’s why I’m cur so I’m kind of like out now. So that’s why I’m wondering if I could do a second business and a second personal or not. 

[00:57:06] Chris Hutchins: So I know that Chase’s rule is that you can’t be a current card member of the card or have gotten a bonus in the last two years.

[00:57:18] Chris Hutchins: Business card excluded. So I think you can only get a personal card. You, I think you can only get a bonus on a personal card every two years. 

[00:57:26] Robert Leonard: But do they count as different cards though? That’s the thing. Like 

[00:57:28] Chris Hutchins: they have the plus and the priority. Think you can’t be a Southwest rapid rewards card holder and haven’t got a bonus in the last 24 months.

[00:57:35] Chris Hutchins: So you might have to, every 24 months, you might have to close the card. So one thing when it comes to card closing, a lot of people think, oh I, you list this episode direct. Why am I using this stupid Bank of America credit card don’t necessarily go close every card. Your credit score is really impactful for a multitude of things from getting good interest rates on loans in the future to getting approved for credit cards.

[00:57:58] Chris Hutchins: And one of the factors is, how long have you had most of your lines of credit? If you have a card that you’ve had for 10 years and you’d realize it’s not the best card, you might not want to get rid of it. because it might be that anchor, you know, kind of bringing the average number of years you have on your credit report up.

[00:58:13] Chris Hutchins: And so the thing that you’ll want to do is you’ll want to either, this is my sequence of events, is one, if there’s no annual fee, just keep it open. You don’t have to close it. You could just keep it open. And I try, every year my trigger is the holidays. Like if I’m going out on the holidays and I’m buying like a stocking stuff or a small gift, I just cycle through the old cards to make sure I put a transaction on that card every year.

[00:58:34] Chris Hutchins: And for some reason, the holidays is like my trigger. Oh, it’s the holidays. I gotta, I’ve got two or three cards that are old. I’m going to go put a couple bucks on these cards. Another option is put like a small recurring subscription on each one, like your Netflix bill or something. If it does have an annual fee, you can one call up the card issuer and ask them, say, Hey, I like this card.

[00:58:53] Chris Hutchins: I’m not spending a lot of money on it. The annual fee’s just a little too high for me right now. Some cards will say, oh, we’ll waive the annual fee next year. Great. You can punt the down the line or, oh, if you could spend $3,000 on the card in the next three months, we’ll give you 50,000 points or some crazy retention offer.

[00:59:09] Chris Hutchins: So if you Google around for card name retention offer, you see a bunch of blog posts of people that are like, oh, here are the retention offers people have recently gotten for this card. Third option is you can downgrade the card. A lot of cards have a free version or a free card in the family. So the Chase Sapphire Preferred you could downgrade to the Chase Freedom or the Freedom Flex or the Freedom Unlimited.

[00:59:29] Chris Hutchins: That’s true about United Cards. There’s a free version. You could downgrade them. So if you’re like, gosh, I have this card, it has an annual fee, they’re not going to gimme any bonus. Instead of canceling it, you could just downgrade it to a no annual fee card. You can call up or even use like the secure chat and just say, Hey, can I downgrade this card to a version with no annual fee?

[00:59:46] Chris Hutchins: If none of that works and you have the card open for 12 months, you can cancel it. And the only hacks there are one, I try to wait over 12 months because there’s some language and a few of the card kind of terms of service that say, they basically say effectively like we can do things. If it looks like you’re the kind of person that opens up a card, gets a bonus, and cancels it in the first 12 months.

[01:00:06] Chris Hutchins: But most issuers have a rule that you can get the annual, this annual fee refunded if you cancel within 30 days of it hitting your account. So you can wait till the 13th month, even 366 days and cancel it. And then you will like never be on the list of person canceled within 12 months, which is a place to you don’t want to be, is like seen in the issuers as opens a card and cancels it right away.

[01:00:30] Chris Hutchins: After you get the bonus, they look down on that. So those are a bunch of options there on Chase. If you ever cancel a, if you do get to a point, you have to cancel a card, and that card had a pretty high credit limit. You can actually move the credit between cards. So if you had a card with a $20,000 limit and you’re going to cancel it and you have another card with a $10,000 limit, you could call Chase and say, Hey, could you move $19,000 over to the other card, which will now have a $39,000 limit, and then cancel the card after you’ve reduced the limit to a thousand dollars.

[01:00:59] Chris Hutchins: So if that limit is important to you, you can move it around. 

[01:01:02] Robert Leonard: When I was commuting into an office for work, I listened to a ton of podcasts. But with me working from home these days, I don’t really listen to many podcasts. That said, yours is one I tune into when the guests or the episode topics are interesting to me. 

[01:01:17] Chris Hutchins: Which is all the time, right?

[01:01:19] Robert Leonard: Yeah, everyone, every single one. I am very picky these days like, because I don’t have a lot of time to listen. So like I really read like before your show would be one, I’d listen to every episode just because I like the show. So I’d listen to every episode. There’s very few podcasts that I do that to these days.

[01:01:32] Robert Leonard: So I just look at the title and the guest and see if it’s something that’s really relevant to me right now. And yours is frequent but not always. And one that was, it’s kind of recent, kind of odd, it’s been a few months now, but it was with Bill Perkins and it was the author of Die With Zero. And I want you to tell us a bit about his book and his philosophy.

[01:01:48] Robert Leonard: I think it’s fascinating and I think it’s one that the audience will want to learn a lot more about. 

[01:01:54] Chris Hutchins: First off, thank you for listening. Second off, I’ve started doing something recently. I’ve realized that some people just don’t have time for every episode. And so I write a newsletter where I try to summarize some of the conversation in a newsletter.

[01:02:08] Chris Hutchins: So if you’re listening to this and you’re like, gosh, I just can’t do another podcast, but I could do another newsletter. I try to write like two, 3000 word newsletters to hit on a lot of the main points. It’s never going to be as comprehensive as a podcast. It’s never going to be as timely as the podcast, but backup alternative for someone who maybe has time for a newsletter and not another podcast, but Bill Perkins was such an interesting conversation, probably changed my perspective on money more than any conversation.

[01:02:31] Chris Hutchins: I’ve had this since starting the podcast, and his philosophy is you shouldn’t just aimlessly go down life trying to increase your net worth every month because you should really be trying to increase your net fulfillment in life. And there will be times where you might be better off doing something now than saving money and trying to do it later.

[01:02:54] Chris Hutchins: So if we, a lot of us, if we look at our parents and we are wonder, could my parents run a marathon? Definitely not. Could my parents climb Machu Picchu right now? Definitely not. So there are things that when you’re older, you just don’t have the time, energy, health physique to do. And so if one of your goals is one of those things, you really should be prioritizing it earlier.

[01:03:13] Chris Hutchins: And a lot of the data he shares is super fascinated about the fact that a lot of people have more money in retirement than they think, and they spend less than they thought. And so his case is make sure you’re not waiting till you’re old to spend money and then not able to use it the way you want. And when I left that conversation, I was talking to my wife and she was like, We have X dollars of net worth.

[01:03:33] Chris Hutchins: And she’s like, I think the goal for this year should be a little bit more. And I was like, I think the goal should not be a little bit more. I was like, what if our goal has nothing to do with increasing our net worth? What if our goal this year is to not increase our net worth? What if our goal this year is to not decrease it, but to spend the money that we otherwise could have saved and spend it on life, right?

[01:03:53] Chris Hutchins: Like there’s only so many years where our kids are going to be young enough, they’re not in school. We can take them places. Like maybe this is the time, maybe it’s not. But let’s not just default into the assumption that all we should do with our money is just save. And right now, my wife and I are both working full-time on All the Hacks.

[01:04:11] Chris Hutchins: We’re never going to have as much flexibility with where we live and work as we probably will. Maybe we’ll do this forever and we’ll continue to have this, but if this ever stops or if she ever decides she doesn’t like working with me and wants to do something else, you know, she’ll have to go to work.

[01:04:24] Chris Hutchins: She’ll have to go to an office. For right now, we have a lot of flexibility, so maybe we should use that flexibility. Go live abroad. Maybe we should do longer term travel. I don’t know, but I don’t want to assume that the best use of our savings is to just keep increasing our net worth. Now I realize I saved this from a place where I feel like we’ve saved enough to kind of cover our retirement.

[01:04:46] Chris Hutchins: Obviously those priorities will be different for everyone, but I think a lot of people wait till they’re 50, 60, 70 to start spending their savings and then they leave a bunch of money to their kids because they couldn’t spend it all. And even if that’s going to be you, bill argued, give them money to your kids earlier.

[01:05:02] Chris Hutchins: Like if you’re going to leave money to your kids, give it to them earlier because you actually get to see the joy they get from it, right? If you want like it, it’s just so interesting. You get no joy. If you want to donate your money to charity, great. Donate it to charity when you’re younger so you can see the impact it has.

[01:05:16] Chris Hutchins: It just totally changed my whole perspective on how I want to think about money and what I want its purpose to be. And I was just aimlessly going down to maximize my net worth path and now I’m like, do I want to increase my net worth right now? Maybe I do. Maybe we decide we want more of a cushion because we don’t have the stability of full-time kind of jobs with salaries.

[01:05:37] Chris Hutchins: Maybe we do want to focus this year on building up more of a, you know, a buffer in our kind of checking account if you savings account. That’s our goal. Everyone’s goal could be different, but reframing the conversation on how do I get the most out of my money? How do I maximize life, is I think the thing we should all be trying to achieve.

[01:06:00] Chris Hutchins: And so that was episode 91. You can go to allthehacks.com/nine one, you can find in the show notes. But I think that episode, I think it’s like number one episode I’ve done in terms of downloads. And I think anyone would go listen to that and have an amazing new perspective. You don’t have to adhere to all of it, but I would be shocked if people didn’t listen and say, I want to do something different than I thought I did.

[01:06:22] Robert Leonard: I put the link in the show notes For everybody that’s listening on our show currently, just slide up in your podcast player or go to the investors podcast.com and look at the show notes the link to the episodes there. Like Chris said, I highly recommend you listen to it. I haven’t read the book yet.

[01:06:35] Robert Leonard: I really want to, but I think Chris’s episode did such a good job covering it that I almost feel like I don’t even need to read the book. I feel like I kind of got the gist of it, but I’ll still read the book. But even just the episode itself has really changed my philosophy a lot, and I love to combine this concept from Bill with another concept from Alex Ramey, where he talks about seasons.

[01:06:53] Robert Leonard: He says, okay, well, like if you have five different things you want to do, just do one. For right now, you’re in that season. And if you want to do a second thing, now you’re in that season and if you want to do something else, you’re in another season. Like you don’t have to say no to things, you can just do them in different seasons.

[01:07:06] Robert Leonard: So what Chris was saying is maybe right now, this year is a season where you’re spending money rather than saving. And maybe next season is all about saving. And so I think it’s be really powerful for me at least, to combine those two concepts. And it’s really, I’ve been, I’ve, it is made a big difference in, in my personal life and how I’ve been spending money, how I’ve been saving money and I’ve been trying to enjoy it a bit more recently than I had been.

[01:07:27] Robert Leonard: I had been very, I don’t want to say I’m quite a penny pincher, but I was more on that side than I was in terms of like being, spending a lot of money. So it’s recently I’ve been spending a bit more than I had been in the past. And it feels good. 

[01:07:39] Chris Hutchins: I definitely was in that side. You were a penny pincher. I was being irrational.

[01:07:44] Chris Hutchins: So I had this conversation towards the end of the episode where I’m like, I want to take this trip. And I just feel like there’s not a good deal on the points right now. And he’s like, what are you optimizing for? Are you optimizing for getting the best deal? Your points, are you optimizing for taking the trip?

[01:07:56] Chris Hutchins: What is the thing you care about? If the thing you care about is taking the trip with your family, maybe there’s not a good deal with points, so maybe you spend money on it. Maybe you just accept that you’re not going to get the best value of your points, but you’re going to go on the trip. And it was so funny because we were talking about what to do.

[01:08:09] Chris Hutchins: It was the holidays. My wife had never been to London, she’s from the mountains. And so she was like, we live in California, we’re not going to experience something cold. And even though London is not like the quintessential like snowy winter destination, you know, it has a very holiday charm. And so we were like, you know what?

[01:08:27] Chris Hutchins: Screw it. We ended up booking the flights. It turns out that we actually ended up also getting a good deal, but we committed to go before we knew whether there was a deal to be had. And that year, which is very rare for London, it snowed while we were there. It was like everything that we got that perfect experience that we were looking for.

[01:08:44] Chris Hutchins: And my old version of me would’ve been like, well, if there’s not a good deal, let’s maybe we go next year. And. It was just been the same thing happened. Not quite as great on the deal side. A couple weeks ago, my parents told us that in 2023, there was like one week where we were free and they were free to help watch our kids.

[01:09:04] Chris Hutchins: And so if we were going to take a trip without our children, there was a week to do it. And we were like, great, what are we going to do? And we started looking and we couldn’t find anything. It was a great deal that week. And we just bit the bullet and we paid for a not great deal. Like we just paid the extra money, probably 50% more than we wanted to.

[01:09:21] Chris Hutchins: And granted, it didn’t put us into debt, but it was like I was looking for the deal. I didn’t find the deal. And I thought back to the episode, like literally this moment with Bill Pers, where he is like, what are you optimizing for? Are you optimizing for the deal or taking the trip? And I was like, we. And if we don’t do something awesome, we’re going to look back and say, we wasted the one week where my parents offered to watch our children.

[01:09:41] Chris Hutchins: Like what are we doing? So we just took the trip and we paid the extra money and I have no regrets. Like it was amazing. And that’s what I want to do more of. That’s what I want to use my money. And maybe that means I’m going to spend less money on other things in the future, which is also okay. Like I can also just say, you know what?

[01:09:58] Chris Hutchins: I’m going to like ratchet back somewhere else. And you know, based on my Copilot spending for this month, maybe I should do that over budget. Maybe next month you’ll notice us cutting back a little bit somewhere to kind of feel better about it. And I guarantee the satisfaction we got from that trip we’ll be worth cutting back on.

[01:10:15] Chris Hutchins: Going out to eat for a couple months.

[01:10:17] Robert Leonard: It’s funny, July must be a spending month because I am way over budget this month as well. I had some home improvement stuff that I had to get done that I’ve been just kind of putting off that I finally got done, had to fix my truck a little bit. So it’s been yeah, it’s been a heavy expense month for me.

[01:10:30] Robert Leonard: But Chris we’ve had a great episode. I’ve really enjoyed it. We could keep going for hours and hours. We’ll have to have you back again soon before we wrap up. Tell everyone listening where they should go to find you. Listen to your podcasts. Everything you got going on. 

[01:10:42] Chris Hutchins: Everything’s All the Hacks, so you can search that.

[01:10:44] Chris Hutchins: And the podcast player you’re looking at listening to right now, you can go to all the hacks.com, you could go to Google, you could go to whatever your favorite search engine is, anywhere you look for All the Hacks. I’d be surprised if I wasn’t the first result. And we got a lot of great content. It’s not just about points and miles.

[01:10:58] Chris Hutchins: We spend a lot of time talking about money. We spend a lot of time talking about life, everything from negotiating to family to, gosh, we did an episode on meditation, and then we do these cool travel guides. So about once every one to two months, we’ll pick a destination and we’ll go really deep on that destination and do a whole.

[01:11:18] Chris Hutchins: I don’t want to make it just about one type of optimization, because I think you can kind of go too deep. I love the 80 20 rule, so I’m trying to break down that 80 20 stuff for you so that if you’re thinking about insurance, we got an episode that’ll give you everything you need to know about optimizing your insurance policy.

[01:11:34] Robert Leonard: Links to all of Chris’s resources will be in the show notes. Like I said, throughout the episode, I’ll split a links to some of my favorite stuff as well below. So guys, if you’re interested in checking it out, go there. Chris. Thanks so much. I really appreciate it. 

[01:11:45] Chris Hutchins: Dude. Thanks for having me. This is awesome.

[01:11:47] Chris Hutchins: I agree we could go on and on, so I’m glad you finally put a stop to it. Otherwise, we’d end up with a three hour episode. 

[01:11:53] Robert Leonard: All right, guys. That’s all I had for this week’s episode of Millennial Investing. I’ll see you again next week. 

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