Get in touch

Postlight joins Launch by NTT DATA! Learn more.

Money management has always been a money-making business, so why are so many money-tracking apps not up to snuff? This week Chris and Gina talk about their love of personal finance tracking and the problems with many finance apps out there today. They share the programs they currently use and envision a future of better personal finance apps.


Chris LoSacco: Nothing to hide here… 

Gina Trapani: We’ve got nothing to hide! We’re gonna come outta the closet as just being the—the finance people in our—our family.

Chris: The finance nerds we are.


Gina: Hello everybody. Welcome to the Postlight Podcast. I’m Gina Trapani. I am the CEO of Postlight, and as always, I’m joined by my partner in this business, president of Postlight, Chris LoSacco. Hey Chris. 

Chris: Hey Gina. 

Gina: We’re gonna talk about a pet topic today. Something that we, both, our little hearts just love and glow with warmth whenever we talk about it together. But we usually talk about it together and alone. So we’re gonna talk about it like on the show today. We’re gonna–

Chris: We don’t, we don’t need to have shame around this 

Gina: [unclear]. I say, I love this. You’re so healthy about it. [laughs] 

Chris: I just want—let’s put it out in the world. 

Gina: Let’s just say. Let’s just come out of the closet about this. Okay? I’m gonna set this up. So, in many households, where families or couples, let’s say, share their money or have joint financial concerns. There’s often one person in that partnership or relationship or family who takes the lead on the money, on the family finances. Pays the bills, and makes sure the paycheck is hitting the checking account and like makes sure that the 401k contribution is right, blah, blah, blah. There’s that one person who kind of does that. And in both of our households and families, you and I are that person. 

Chris: Are the people. Yeah. 

Gina: Is that—Yeah. Does that, does that ring true for you?

Chris: Mm-hmm. 

Gina: My life partner—I’m just distinguishing between business partner and life partner. My spouse, my wife and I, we—we make joint decisions. We talk about it together, but I am the one who is like, “Hey, do you wanna look at the spreadsheet?” [laughs] Like, I am always the one who, like, initiates that conversation.

Chris: I just wanna point out, because people, this is an audio only podcast. We don’t have, like, a video. When your face—when you said “spreadsheet,” you lit up like a thousand Candles.

Gina: [laughs]

Chris: It was like I could see the joy, the personal finance joy. 

Gina: Oh, spreadsheets are so cool. They let you put information about your life in small boxes and organize it and make you feel like you have the illusion of control. That’s what spreadsheets are, and that’s why my face lit up. And it is an illusion, but it is such a powerful drug. [laughs] it just is. 

Chris: There’s more to unpack here than we will have time to do. 

Gina: There is. This may….

Chris: One podcast episode… 

Gina: ….beyond the scope of our personal finance—love of personal finance.

Chris: Right. Right. 

Gina: So I’m that person in my household. I read personal finance books in my, like, free time. I like, you know, go on the Reddit and read all the forums, like, for fun. Like, it’s my way of relaxing. And she’s like, “I’m so grateful to you.” But then also there are times when I’m like, “You wanna look at the spreadsheet?” And she’s just like, “No, no, not this weekend. Like some other times.”

Chris: Yeah, like “Please, no.”

Gina: Yeah. “Please no. Not right now. I’d rather watch the sports.” Or whatever, and I totally respect that. So you and I are both this person and then we go to work together and I’m like, “Oh, did you see this app or did do,” like, I will be like, “Did you see like the rate on I bonds?” Like, you know, “Did you see that like this—this savings account interest rate, like, went up?” And you’ll be like, “Oh yeah…” 

Chris: These are not hypothetical exhibits. This-—these are actual conversations that have happened between us. 

Gina: We’ve had every single one of these conversations. You know, you being the, just one of the—the best product person I’ve ever worked with. I love being like, “Hey, did you see this app? And like, what do you think? And like, what do you use?” Right? Because I know that you are incredibly discerning about the kind of tools that you use, the experiences that you wanna have, especially for things that are close to your heart, like personal finances. And I wanna talk about the tools that we use and what we like about them, what we don’t like about them. And I also just really believe that there’s so many opportunities in the personal finance space. 

Chris: Yes.

Gina: That could help people manage their money and by extension, you know, a lot of aspects of their lives better. And they’re just not there. And I’m not totally sure why.

Chris: It’s a complicated question. I mean, I think that’s part of why. I, and I completely agree that there’s a ton of opportunity here and I’m not sure where it’s gonna go. I’m not sure how this market is gonna evolve. I’m not sure what kind of options are gonna be out there because there’s no one right way to do it. And there are all of these sort of various, like, kind of levels of abstraction that you can think at when you think about how to manage your finance. Because there’s budgeting and saying, you know, “I only wanna spend X amount per month on dining out, and I know my utility bills are around Y. And so I just need to, like, lay that all out in the table and then make sure that I’m making good decisions.” and that is a particular kind of, like, day to day approach. I mean, really, it’s like you want that information at the point of decision, right? 

Gina: Yes.

Chris: So that you can say, “I shouldn’t actually go out to dinner right now,” or “I need to make sure that I only. $30 because I’m, you know, close to my cap on my budget” or something like that.

Gina: Mm-hmm. 

Chris: So there’s budgeting tools. Then there’s like wealth management and what’s the right, like, investment strategy, what’s the right allocation, you know, which is a whole other sort of approach to things. And then there’s also just, like, making sure you understand where your money is going, which is not real—I mean it’s related to budgeting, but it’s also not really budgeting. Right. It’s. You know, analysis, if you want to think of it that way, and making sure that you are making good future decisions based on what’s happening day to day. And there’s no one tool, I think, that nails all of these things. And maybe it’s unrealistic to think that it is one tool? Maybe this, maybe this is gonna be like, A suite of tools or, or a different kind of setup based on what you’re, what you’re going after? But I think one of the challenging things, and thus exciting things about this market is that there isn’t—There’s no one right way to do it where it’s like, “Oh, it has to look like this and it has to function like this.” There are a lot of different approaches. 

Gina: Yeah. I mean, I’m typically in favor of, like, one tool that does one job really, really well. But the thing about finance is that everything sort of relates to the other thing. I mean…

Chris: Exactly.

Gina: One aspect of personal finance that you didn’t mention was, like, just debt management. You know, I’ve got credit card debt, student loan, a car loan, so Right. So I think a natural question is, “Should I contribute to my 401k when I should be paying down the sort of high interest?” Like they’re all sort of tied together. And like cash flow and like, did I hit my, you know, budget? Like they’re all kind of related. So I think on some level I’m really still holding onto the dream that, like, an all in one solution is, is the right one because everything sort of touches, you know, Each other, like, I’ll often see people be like, Should you know, what should I put my money toward? Should I pay down my mortgage early? I have this good interest rate, or should I invest it, or should I pay down my credit cards and should I do, You know, there’s like the snowball method of paying off credit cards versus the avalanche method, you know?

Chris: Mm-hmm. 

Gina: There’s all these different approaches. I mean, we, we won’t even get into like all the gurus, you know, the Dave Ramseys and the, you know, there’s Susie Armon. There’s these personalities that have just built it to..

Chris: Have their particular way.

Gina: … their personality around their particular methodology, and here’s what you should do. So I tend to think there should be kind of an all in one. I go into the finance section of the app store. And I scroll through the, like, beautiful candy store of all these like app icons of, like, the one job things. And I’m like, this looks really nice and slick and modern. And I’m like, I can’t start use—I can’t invest time into this thing and I need, like a—a holistic approach. I mean, I started using back in, I think like 2002, I think it’s like the early two thousands. I started using Microsoft money, which was kind of the standard for people who, you know, enjoy and wanted to track, you know, all their transactions and see all their accounts in one spot. I was very much, I was much younger in the early two thousands. But it was this point in my life where I was like, Oh, I have multiple accounts. I have a checking account, retirement account, mortgage account. Like, I now I have multiple accounts. I wanna see them all in one place. I think I was also just like freelancing at the time. So like I didn’t have a steady income month to month and, And I used Microsoft Money. Microsoft Money is a great piece of software. I loved using it. Absolutely loved using it. 

Chris: It’s wonderful. So I have—I have a confession to make. Yeah. I still use Microsoft Money . This is my. Preferred. I am not advocating this approach. I don’t even think you can download the installer anymore. I do have the E… 

Gina: You have it saved. You showed me… 

Chris: So that if I have to spin up a new machine, I have that piece of software. But I have—I’m the same way. I started using it in August of 2002, so I have 20 plus years of financial data stored in this piece of software. And I gotta tell you, Microsoft money is, it’s like a pickup truck, you know, that you bought 20 years ago and it’s still running. Like it is just bulletproof. Like it keeps chugging along and it keeps doing its thing. And there are, there are things about it that no longer work, like you can’t auto sync transactions anymore, which is kind of crazy. The way that I sync, I do electronic reconciliation is I go to my credit card or I go to my bank, and I download..

Gina: Oh! 

Chris: OFX files.

Gina: OFX files! What does it stand for? I don’t, I don’t know. It’s like..

Chris: Open, Open Financial Exchange?

Gina: Exchange or something. 

Chris: Yeah. 

Gina: Mm-hmm. 

Chris: Which—thank God most banks still support them. Eventually, they’re not going to. 

Gina: They do. 

Chris: I know. There’s something to be said for, you know, a great piece of software that—that just works. There are things that it does not do, like it is not a great budgeting tool. 

Gina: Mm-hmm. 

Chris: It is not a great investment management tool. Like it—it will keep track of transactions and do that really well. And I have a really good sense of where our money is going because I keep track of, you know, every credit card transaction. I mean, even ca—I rarely use cash nowadays, but like cash transactions, I track there too. 

Gina: You’ll go in and like enter, I can’t—like manually enter cash Transac—oh! I’m—It’s so impressive. So can you just say what the name of Microsoft Money, like the official name of the version Microsoft money that you use right now? Because listener, this blew my mind when Chris shared with me that he used Microsoft Money. You told me this like years ago. We’ve been working together for like almost seven years. You said it to me and I, like, walked around in the world and in the back of my mind, just every once in a while I would think Chris uses Microsoft money, still. [laughs]. And then I would come back to you and be like, Are you sure? And how? And like what, what computer are you running it? Like I would, and then you would tell me, and then I’d walk around in the world and then, and a few months later I would, like—just like sort of clang inside me. Like Chris. Yeah. 

Chris: It’s a little ridiculous.

Gina: It—it became sort of like a little bit of mythology at Postlight.

Chris: Yeah. 

Gina: Amongst the partners at Postlight. So what is the official name of the version of Microsoft Money that you use right now. 

Chris: Microsoft Money, Sunset Edition. They wanted it to be very clear…

Gina: This is the…

Chris: “This product is end of life.”

Gina: ….the last version. Sunset. 

Chris: “You should not be using this.” 

Gina: And when? When did they officially sunset… the Sunset Edition?

Chris: My God. 

Gina: I mean, it’s been like almost a decade? 

Chris: I think more than 10 years. Let me look at the date on the installer. Just—Just for—because why not? I got this installer in 2017. So.. 

Gina: Okay, so you downloaded it off the internet in 2017. 

Chris: I downloaded it off the internet five years ago. 

Gina: And you are a Mac—Like how are you running this thing? This is a piece of Windows software, right? 

Chris: Piece of Windows software. You know, God bless Microsoft because backwards compatibility is, like, at the top of their list. 

Gina: Yes.

Chris: You can run software from the eighties, like on Windows machines from Windows. 3.1 or whatever, and it still just fires up just fine. 

Gina: Right. Right. 

Chris: So for a long time I ran a virtualized machine on my Mac. So I used Parallels. 

Gina: Parallels, mhm-hmm.

Chris: Which is a virtualization software. You can also use Virtual Box or VMware. 

Gina: Mm-hmm. 

Chris: And then I got a Mac with Apple Silicon. And Parallels wasn’t supported at the time. You couldn’t run Windows, so I bought a PC. And I set it up, and it basically runs Microsoft money for me. It’s a modern pc, it runs Windows 11 and I remote into it to use Money and it’s, you know, again, it’s pretty hacky, but it works just fine. 

Gina: Yeah. 22 years of data. I mean, this is a—just a testament to how powerful it is to have invested—especially you have done a lot of manual entry like this represents hours, days, weeks of your life…

Chris: Oh God, yes. 

Gina: …that you’ve invested into this, right? So I’m an incredibly lazy person and I really enjoy personal finance, but I really don’t enjoy hand entering transactions. And I got to a place where I was like, I can’t do this manually. Cause I was also downloading the OFX files because at that time Money wasn’t connecting with all my banks and it just became a data entry session and I was like, I don’t want the data entry session. I just wanted to see the charts. Right. I wrote a piece about this on, On Life Hacker. I mean it was like 2009, it’s called “Why I stopped being paranoid and started using Mint,” but I switched over to Mint. 

Chris: Mm-hmm. 

Gina: Which still kind of upsets and galls me because the way from Mint—

Chris: Why?

Gina: Because—So Mint automatically downloads all your transactions. Like I don’t, I do very, actually little—at the expense of being more high resolution, like I don’t, you know, like split my paycheck into like taxes and retire—like I just take the net amount and just roll with that because I’m like, I don’t wanna do this state entry. But in order for Mint to download all my transactions, It is unbelievable to me that we have not, that we don’t have, you know, safe and secure off for banks. Like I have to enter—anyone who uses Mint knows this or something like Personal Capital. You have to enter your bank’s username and password. 

Chris: And password. I know. 

Gina: It is unbelievable to me. And it’s unbelievable that I did it. Cause I am the person, you know..

Chris: I know. 

Gina: ….who uses two-factor and has safe and password—like—I’m like paranoid.

Chris: Yeah, you’re very… 

Gina: I’m pretty….

Chris: … into online security.

Gina: You know, if someone emails something with my social security number, I freak out and then immediately never interact with them again. Like I—it just—I’m—I’m pretty paranoid about my personal information and yet I was like my laziness, my utter laziness or game—my, it was, it was the, the quintessential sort of convenience over privacy, you know, trade off. So is this changing because it’s 2022 and there still isn’t a safe way for most banks to create an API key, which is read only, you know, that you say this is for Mint and it’s read only, right? Like the fact is that Mint has my bank logins and if something went—went wrong and into it, they could theoretically with this, these login credentials, like, execute transactions on my accounts. And that does definitely keep me up at night. Now that I’m saying this, I’m—I’m really wondering why I made the choices. 

Chris: Yeah, it’s kind of freaky. 

Gina: It’s kinda freaky. 

Chris: My, and I’m speaking as a consumer, not an expert here, but my understanding is that this is changing and more and more banks are adopting modern O off, like ways to exchange credentials without having to pass username and password. And Mint, you know, at least back in the day, they must have been storing username and password because they had to go log into the bank. 

Gina: Yes. 

Chris: But what’s interesting is, you know, like two factor being adopted more widely, which has really happened in the past five years or so, has pushed the banks to solve this problem because you can’t—like, it’s not just using password anymore to get into your bank, right? You’ve gotta authenticate on the app or get a text message or do a security question. So Mint and Personal Capital and the like, they had all of the—and by the way, I’ve tried many of these platforms just to see what they’re like. They all had hacky ways to, like, get around, you know, Please make sure that you put in your security question, answer so that I can submit it on your behalf when I log into your bank, right?

Gina: So now Mint has your security question answer. So that—that’s awesome.

Chris: Right? But—but I think what’s happening is that more and more banks are adopting modern authentication ways. So—so if you wanna log into Capital One from Personal Capital, then it will prompt you to log into Capital One, and then Capital One will generate a token and give it to Personal Capital to use. 

Gina: This is—is the way to do it. 

Chris: Which is how it should work. 

Gina: This is how it should work. Here’s the problem. The incentives are all misaligned, right? The bank doesn’t want to give you a safe and secure way to let a third party app access your data because the bank wants to show you their own little dashboard of your transactions.

Chris: Exactly. 

Gina: You know what I mean? And they wanna own that data. So at some point I was like, well, the amount of fraud that happens because people have to share their username and password will—will increase to the point where the banks feel compelled to create, You know, it’s actually a safe, secure. And I’m happy to hear that Capital One does it. A lot of my accounts that I’m still doing use the username and password thing.

Chris: It’s been a slow adoption. But you are so right that what, what happens is that the, the banks and the credit card companies and the like, they want you to see their dashboard. I don’t know if you’ve logged into your credit card recently. I do it all the time. 

Gina: I have. Yes.

Chris: Because I download my transactions. 

Gina: Yes. And they have the chart of your spending and… Yes. 

Chris: Well, the chart of your spending. Cool. That’s in theory that’s useful to me. Or you know, a typical credit card user. But what you also get is like, install this browser extension.

Gina: Yes. 

Chris: Because we’re gonna save you money. And did you know you can book dining through us because you get five x points and all of this nonsense, frankly, that is like, this is not helpful to me. And even if there are some good offers in here, they’re being drowned out by all this other crap that’s like, I don’t, I just wanna see what I’m spending my money on. There’s a reason for that, right? They want to get affiliate fees or they want to get your data so that they can anonymize it and sell it to somebody, and it becomes this whole secondary ecosystem around you just using your credit card or using your bank. Yeah. It’s just, it’s really frustrating and it makes me, you know, wanna avoid going and logging in as much as possible.

Chris: Yeah. 

Chris: The mobile apps are a little bit better, but even the mobile apps have 

Gina: Problems themselves. 

Chris: …Like, lot of popups and ads. 

Gina: Yeah. Yeah. I mean, I noticed that my credit card started to do some of the, you know, charting and about spending and stuff, and I was like, Oh, they’re trying to be kind of like a mini, a mini Mint. Here’s the thing. Mint’s business model. It’s an ad business. Like they also, also, they recommend credit cards. They kind of try to sign you up for loans. Like it’s, you know, the reason why it’s free is that they can make you those offers. And I’m sure that there’s affiliate fees and the whole thing, right? It’s just on a, it’s just across all of your accounts versus just your credit card account. And look, I mean, you know, on some level I’m like, you gotta make money, right? You have to earn rep—like there has to be a business model here and you know, Mint’s business model is advertising. Personal Capital is interesting though, like Personal Capital is, is..

Chris: They’re trying to sell you advisory services.

Gina: They—Yeah, it’s an upsell for their in-house advisory services. So when you log into Personal Capital, you’re not seeing offers for credit cards and loans and—and other things. But they’ll call you or they’ll prompt you and they’ll literally show you like, “Here’s, you know, the advisor’s calendar.” 

Chris: “Schedule your call.” 

Gina: “Schedule your call.” Like pick, you know, Thursday at 10 45. Personal Capital also has this, and I think that this is true of a lot of financial services and apps, is this, is this like fear based sell. Like they’ll be like, “Look at your account.” 

Chris: “You’re missing out.”

Gina: “You’re gonna be down to $5 when you hit 76. Like, look at like, you really need some help. You seem really weighted.” and this—and you know this, the fear based thing, I remember when we had the folks from the 401K plan come speak to our employees at, at Postlight. 

Chris: This was a couple years ago. 

Gina: This is a couple years ago. And you know, we have relatively young employees and, and this person. He went from zero to like, “Do you wanna be eating cat food? You know, when you’re 80? If you—then you’re not contributing to your 401K.” and I was like, “Whoa, whoa.”

Chris: Whoa. Yeah, that was pretty intense.

Gina: It was intense and it was dark, but it is this fear based sell. Like, are you, are you gonna be able to support yourself? What if we have a health, you know, catastrophe. What if someone dies? What if you can’t send your kids? I mean, it’s like . It’s scary. And so and so Personal Capital doesn’t go to the cat. There’s no mention to cat food as—as far as I remember. I used Personal Capital for a little while, but it definitely is this like, you know, your asset allocation looks a little off for your age. Like you should really talk to somebody. And so also, I get it, that’s their business model, right? They wanna upsell you into their advisor services. There’s other, I mean, there are other apps, right? Like Quicken, I think ,is a subscription. Things like You Need a Budget is a subscription. It—it’s a little product that people who are trying to ostensibly pay down debt, save and invest are gonna agree to, like, pay a monthly or annual fee to use software. Like I think the days of Microsoft Money, when you purchase this, like, desktop app, download it and use it for 22 years..

Chris: Those days are gone. 

Gina: Those days are gone. Those days are gone. The market mustn’t have been there. 

Chris: I feel like I got the deal of a lifetime.

Gina: [laughs] Yeah! 

Chris: Because I’m—I paid once for Microsoft money at some point back in the distant past, and I’m, I’m gonna use this thing until the wheels off.

Gina: Until the wheels fall off. Yeah. Yeah. 

Chris: It’s funny because you said that, you know, is there not a market like the—Quicken is interesting, right? I haven’t looked at Quicken in a long time. They have a—an ecosystem. They do have a—a subscription service it looks like. Right? That start—starts as low as $3.50 a month, which is not that bad, I don’t think it’s unreasonable to think that people are going to put in a little bit money.. 

Gina: For value. Yeah.

Chris: For value. And you know, depending on what you’re getting out of the tool and if it’s influencing your habits, I mean, it could be worth it many times over if you are, you know, making smarter decisions because you’ve got a good setup in place. But I still feel like no one’s cracked it. You know? And we’ve been circling around the fact that all these incentives are misaligned. And I, and I wonder if there’s gonna be, you know, an upstart or one of the big players who says, We’re gonna right size this so that people are paying for value, and we’re not trying to shoehorn in all of these things that are not really in their best interest. So, I don’t know, I, It’ll be very interesting to see how it evolves. 

Gina: Do you only use Microsoft Money? Meaning this is a leading question cause I know there’s something else. So in addition to Mint, I also have a spreadsheet. Do you also have a spreadsheet? 

Chris: I do have—I do. I have a set of spreadsheets and I want to hear about your setup. The one thing I will say for me that has been very helpful is tracking cash flow for projected spending, which Microsoft money does not do well. So if I know that I have a big expense coming up or a credit card payment that I want to make sure that you know, my paycheck has hit before something is going out.

Gina: Mm-hmm. 

Chris: I do that in a spreadsheet and that’s been very helpful. And again, that goes back many years. I also track, like, I thought check writing was gone and then, you know, for the past few, like little while I’ve been writing a lot of checks. 

Gina: Really? 

Chris: It’s kinda weird. Yeah. 

Gina: Yeah. It’s weird. I, like, forgot how to write a check and how to write one. It felt so weird and I was like, wait, I put the stamp like I, I, yeah. I was like, oh, this is strange. 

Chris: Just send me a QR code or something. I don’t want—I won’t have to write a check. 

Gina: Yeah. 

Chris: But something that’s interesting about a check is that you’ve gotta make, you gotta make sure you keep those funds around because you know it might, if someone doesn’t cash it for a couple of weeks, like you need to make sure that you have that money in your account.

Gina: Nightmare.

Chris: It’s a nightmare. So tell me about your spreadsheet set up. 

Gina: Well, I mean, I also have a spreadsheet because, you know, at some point I was like, Mint is good at tracking actuals and what happened in the past and what is done. 

Chris: Yeah. 

Gina: Mint is very, very good—like it learned very quickly how to, it auto categorizes everything. So once a month I, like, just go and I go in a Mint. I look through things and everything—you know, and I like to see like, how are, you know, how are we spending our money? Like, there’s, like, some shame about how much Seamless was there. You know, you know, how much did we save? That kind of thing. And it worked like that for a long time. Just always looking back. Backward at actuals, were doing well in the budget. And then I got to a place where I was like, like—like you said, I wanna project. I have, I have this big payment coming and I just wanna make sure that like what’s in my, you know, checking account is gonna cover it, that, that kind of thing. I wanna project cash flow, but then I also just wanna project like over time, you know, if I do, you know, contribute a little bit more to this account, you know, my retirement account versus, you know, my investment account, you know, what would that look like over time? So I have a—I have a spreadsheet that is my sort of projections forward, right? So like I’ll, you know, grab all the balances of my account for that past month, not the transactions, none of that. I just, the—the balances the account. And then, You know, and then I project forward. “Okay, I have this kind of interest rate here. I’m expecting, you know, this, you know, hopefully conservative, you know, return for my investments here.” and, and then I can see, okay, well where does this put me, you know, in the next couple of years. You know, my—I—I’m gonna have my kids tuition for this many years. That, that kind of stuff. 

Chris: Yes. 

Gina: And Mint and Personal Capital—there are very few apps that actually do this. This—this is the realm of financial advisors. Like..

Chris: Exactly. 

Gina: There’s a whole ecosystem of finance apps like eMoney that are b2b. They’re advisor dashboards. 

Chris: What’s e—Sorry. What’s eMoney? 

Gina: So if you’re a financial advisor, a financial planner, you essentially get a license. This is my—my vague understanding, not being a financial advisor or financial planner. But you get a license to a platform. I think there’s one called eMoney. There’s a bunch of them, and you essentially make it available to your clients. So then you sit down, you’re, you’re an advisor planner. You sit down with your client and you take down, you know, Okay. Expenses, income, investments, and then you entered into this platform and then if you’re an active customer, you can log in and like look at your stuff. Some places like, like Vanguard, I know, like, has their own sort of, you know, financial planning sets, you know..

Chris: That makes sense.

Gina: …on their website. But I think then there are these other platforms because then you can hang a shingle as an independent financial advisor, but then also have, like, software. Cause I think these days people expect that there’s gonna be sort of planning software available to them. I found this one consumer, one called On Trajectory, which kind of lets you do this, like as a—as an individual. And to be totally frank, it didn’t do much more than my spreadsheet. Like I can make a—a line chart over time in my spreadsheet, like in Google Sheets, which is what, which is what I do. So that’s the main thing that my spreadsheet lets me do is this projection. And this—running scenarios, you know, And if I made a—a decision about my life that’s gonna affect my finances. If we take that big vacation, whatever it is, like then I can see how this is gonna affect my life going forward. That’s been my setup.

Chris: It’s so surprising to me that all this stuff lives just at the, like, financial advisor. I mean, I guess it’s not surprising, right? But you shouldn’t have to get a financial advisor to get this kind of, you know. And setting up a spreadsheet is easy enough, but it does take, like, some ongoing maintenance and there are some people like you and me who like investing that time and saying, I want to get my tooling just right. And I want, you know, I appreciate the flexibility of being able to tweak all the knobs and dials and stuff, but a lot of people just want, they want the same outcome without, you know, or 80% of the outcome without all the tweaking and the knobs. And if you could make a reasonable guess or put a few options in front of people and say, Just like you’re describing, here’s what, you know, a $10,000 vacation would look like and how it would affect your next couple of years. Like, that would be really helpful and valuable and wouldn’t require, I think, a lot of like specialized algorithms, you know, to plan out. 

Gina: It wouldn’t. There’s actually, there’s this product that caught my eye recently. It’s called Tiller, and it’s an add-on for Excel and for Sheets. And so you added onto Excel sheets and then you off to your bank accounts the way that you would use like Plaid. You know how Plaid is like the… 

Chris: Oh yeah. 

Gina: …the Connector API? Uses Plaid. It connects your bank accounts and it downloads all your transactions into your Excel or Google sheet. And you know, there’s a couple of add-ons for, like categorize, okay, if this piece of joint should be restaurants or whatever. So it essentially just pulls in all your transactions into a spreadsheet. And for a spreadsheet nerd who wants to just design their entire financial management application inside a spreadsheet, which I have to tell you is incredibly tempting just because I truly enjoy working with spreadsheets. 

Chris: Yeah.

Gina: It’s, you know, that can be kind of your all in one. And I’ve spoken to in my, in my travels, you know, it’s a really hardcore personal finance folks who are just like, The spreadsheet is the answer. There’s no app.. 

Chris: Spreadsheet is the answer. 

Gina: …that’s ever gonna do what you want it to do. The spreadsheet is the ultimate configurable, programmable, you know, finance. And with—with tiller automatically downloading those, you know, So I’m not like uploading a CSV or whatever I would need to do. OFX. Like it really is that that lazy part of me that doesn’t wanna do data entry, it kind of solves that. So I haven’t used to learn myself because I was like, I will literally sink months of my life into perfecting—like recreating inside a Google sheet or Excel sheet. And this is not a good use of my time. I have a child to raise and a company to run. And as much joy as this would bring me, like, I shouldn’t do this. I should not do this. [laughs] 

Chris: well, in a few years, if you want to, you know, take some time away and this is like a passion project, then maybe, 

Gina: But what if Tiller breaks. I got, you know, there’s just, there’s all these, kind of, you know—But it’s a really interesting idea. Like I love the idea. I was like, okay, this is taking control of your data. You are sharing your passwords for that auto download. I mean, there’s that trade off no matter what. Although again, I hope—I hope that two-factor authentication, like you talked about, it will be a reality soon. But I think that is for the extreme, do it yourselfer. 

Chris: Listen, this is cool by the way, and the sort of community feel to this where you can share ways that you’re using Tiller is really interesting. There are levels, right? And this, this is not extreme in my view. Like this is like, okay, I connect to the idea that like the spreadsheet is kind of the general purpose workhorse that’s gonna get you a lot of the way there. Yeah. And if you can build on top of that and say, I’m going to make it easier to, for example, get your transactions or use a debt pay down template to get you on sound footing with your credit cards or something.

Gina: Yeah.

Chris: That makes a lot of sense to me. I don’t know, I, I, maybe this is. The future of where this market is going, The personal finance market. I don’t know. It’s interesting. 

Gina: I have actually seen, like, finance bloggers be like, I’m selling my—my Excel template for, you know, $50. Like this is what I use with Tiller. You know, and it’s a multi tab, super—you know, with a few entry points. So it’s sort of like a, a marketplace of—So you have to start from a blank spreadsheet. And so I’m curious about your spreadsheets. You said you managed cash flow there. Do you also do kind of just projections into the future, like scenarios running? 

Chris: I do. I do scenarios running. I also do some budget reconciliation that pairs with Microsoft money.. 

Gina: Right.

Chris: …around certain things. And then I also had some debt pay down stuff that lived—The transactions were tracked in Money and then some other stuff was in a spreadsheet. But yeah, I mean, it’s like a, you know, it’s like anything, You have the right tool for the right job. 

Gina: Yeah. Yeah. So I’m curious, when you tried Mint. You said you tried Mint and personal capital. What did you think? I’m curious, like, I mean, obviously it didn’t stick because you’re, you’re still using Money, which again, I think is amazing and data. 22 years ago. 

Chris: Amazing in quotes.

Gina: “Amazing.” [laughs] but I’m curious what you thought about—about those apps. Were they just not enough or you were just sort of like I, I have my system, I’m happy with my system and I just wanna keep using my system and a tool that I know?

Chris: It was kind of more that. Which is not a great answer. I acknowledge that, but I have, for better or worse, I have developed some, you know, control freak tendencies around how transactions get entered.

Gina: Mm-hmm. 

Chris: And reconciled and lined up. And it all, it sort of—all—sort of orbits around the interface and the flow that’s defined by Microsoft Money.

Gina: Mm-hmm. 

Chris: And so I, I wanted to try Mint and Personal Capital and the like to see if it—it felt as or more natural. And I haven’t found that tool yet. 

Gina: Mm-hmm. 

Chris: But I’m gonna keep trying them and hopefully I think one will…

Gina: Click at some point?

Chris: One will stick. Yeah. But it is again, I keep making this point, but it’s like different needs for different people and different use cases. Right. And I think I am of the mind that, you know, a little more control like that feels good and doesn’t feel like an extra burden, even though it does mean like a little more work for me. But I appreciate that because I want to, I want to know down to the dollar where everything is going.

Gina: Yeah. 

Chris: Not everybody is like that.

Gina: Not everybody is like that. You gotta do the thing that works for you. Also, some chores, kind like—I, like, I, I enjoy washing dishes. It’s an end place. You kind of go to this like, and I think if you enjoy it—like also if you’re doing that manual entry and you’ve got a system, you, you’ll catch stuff. Like it’ll be closer. You caught something recently. You’re like, Did something change about our paychecks? And I was like, What? No. And I, and I consider myself someone who, like, keeps a close eye on things and I missed it. but you caught it because you were doing sort of your, your normal, like, let me enter, you know, what’s..

Chris: Breakdown.

Gina: …going on? Yeah. And I was grateful for it. To you. I was like, Oh, this is, you know, and then I was like, maybe I’m too loosey goosey with this stuff. Which my wife would not agree. [laughs] 

Chris: This is the thing. I do catch things, but it’s rare. It hardly ever happens. And so, Is it worth—Is it worth the time investment to get this like minor payoff every now and then, like again, everyone’s gotta make that choice for themselves.

Gina: Yeah. Yeah, absolutely. You must have some amazing, like 22 years worth of charts, like you must have just like a picture of your financial life for most of your adult life is incredible.

Chris: It’s actually fascinating.

Gina: Is it? 

Chris: Yeah. To look back year over. and see how—how things evolved. I mean, also the value of a dollar changes..

Gina: Yes. 

Chris: …when you’re looking over that time scale. It is fascinating to see, you know, where like, you have a kid and then where, where your money’s going is like very different changes. 

Gina: Yeah.

Chris: Or like spending on our pets has evolved over time has been really interesting to see it just, it’s, you know.

Gina: Renting versus ownership. And to daycare, like yeah. It really is fascinating to see, like you really can see a picture of your. In the numbers. Well, I’m so glad that we finally had this in depth discussion about all this. I feel, I feel better, I still feel unsatisfied. I feel like there’s opportunities in this space to make some better from some really good experiences and some better experiences. But I, and I do think that the—that the incentives in the market are misaligned. It just—it hurts me when I see people are, like, I just don’t know what to do. Like, I don’t know what to do. And, you know, and there’s so many different approaches to things, and I don’t feel like I have control. And I think for—for me, keeping track of this stuff is again, and maybe this is healthy, maybe it’s unhealthy, but it is just a little bit like I just wanna know where things are. Cause that helps me sleep at night. And I feel like a little bit more control over, you know, and a little bit more informed when I make decisions in our lives. You know, especially when you become an adult and a parent and a business owner and all those things, like you have to make big, weighty decisions and it’s, I like to be data informed.

Chris: That’s perfectly said. I will add one more thing as we sort of leave by looking ahead. Very often, financial decisions, especially as you get later in life, are not just or, or earlier in life, frankly, are not just you. 

Gina: Yes. 

Chris: Like it involves your partner or your family. You know, at varying times in your life, it could be your parents or your roommates, or you know, when you’re a kid and you’re sort of maturing into spending money, It’s like, you know, that’s a whole different thing where it’s not all your money necessarily. I would love to see, Tool or a system that allowed for multiple collaborators. 

Gina: Oh, interesting.

Chris: You know, to talk about money things mm-hmm. and let, and, and have the tools support these complex, you know, relationships and, and decision making hierarchies that exist and make them easier. Just to your point before about how being informed can make these decisions feel better, like how great would it be if you could ease some of the stress and pain that people feel around making tough financial calls if you gave them better data about what they were doing? Right? 

Gina: Yeah. 

Chris: And whether it’s a married couple or roommates or a family or whatever like that. There’s just so much opportunity, I think to—to make this less scary for people who, who, you know, I mean, we all have to make decisions about money every single day. 

Gina: I completely agree, and I think data is like step one. I mean, the thing about the data is like, We’re like, what are the stories that, that we’re telling ourselves about what the numbers mean? And, and this is actually a big leap that my wife and I had to make, where she’d just be like, I don’t wanna, I don’t wanna look at a spreadsheet. We went through this at Postlight, you know, when we were doing our sort of regular financial performance meetings, you know?

Chris: Oh yeah. 

Gina: We’d bring up a big spreadsheet on the screen and we’d be like, ” but what does this mean? Like what do we think? What are we telling ourselves? Why do we think this happened?” And like, that’s the conversation…

Chris: Great point. 

Gina: ….and this is such a good and important conversation to have. It’s also I found, and I like to be like, “why did we make this decision? Oh, right, here’s what we were thinking. Here is the assumptions that we made that we had. And this is the reason why we went down this path.” And so that when you’re like, “Ah, this actually isn’t, kind of, isn’t working out.” You know, can, we can change our minds here. And so I think in my household, like the numbers are the starting point, but then it’s, It’s a conversation of like, here’s what we were thinking. Here’s what we’re thinking now. Okay, now here are the adjustments that we made. Or like, you know, we really overspent this month on like this one particular thing. Like why did that happen? Oh, well, you know, there was the birthday party and that special dinner and blah, blah. Oh, okay. Those things are actually really valuable to us, and we’d spend that money again.

Chris: Hundred percent. 

Gina: Oh, we’re spending on this budget. This is wonderful. Good for us. We’re using our money in meaningful ways. Versus like, Oh, we DoorDashed three times that week because it was a hell week and we didn’t plan well and we didn’t feel good about it afterwards. If we wanna change, we might make a different decision about how we schedule our lives. Like those are two different—but the spreadsheet will just say, You overspent your budget. 

Chris: Right. 

Gina: And that feels like failure. 

Chris: Red cell. 

Gina: Red, you failed. You set a budget and you failed. And I’m very much just like, well, let’s use our money for, like, things that make us feel good in our lives. Right?

Chris: Exactly. 

Gina: So, I don’t know if an app can do this. [laughs] I mean, you can’t, right, like the way you interpret the stories. But like Mint has this thing, this little box on the dashboard that’s like insights. And I keep looking at it and it always says, “We don’t have any insights for you.” And I keep waiting. I want, like, I’m waiting, waiting for the insight. I wanna hear something, I want.. 

Chris: Give me the good stuff.

Gina: … it to tell me something that I didn’t think about or I didn’t know.

Chris: Yeah. Yeah. 

Gina: And I want the insight to be something more than you overspent, you know what I mean? Like on—on this category. I would love it if Mint was like, Oh, you know what? You and your daughter’s birthday was this past month and you had a couple, you went into a restaurant a few more times. Good for you. Happy birthday…

Chris: Exactly.

Gina: …. rein in your restaurant spending next month or whatever it is! [laughs] like, And here’s the thing, it has all the information to do that but I don’t think that’s where the—the effort goes in the product. But having those insights and like telling those stories and correcting those stories and recording those stories and revisiting them and, and reframing them, I think is the ultimate sort of personal finance application. Now, I kind of wanna take a crack at this!

Chris: Totally! 

Gina: [laughs] 

Chris: Yeah. It’s a human humanized—human centered approach to how this all comes together as opposed to, you know, data. This is where the spreadsheet falls down. 

Gina: Absolutely. 

Chris: The spreadsheet is good at so many things. 

Gina: Absolutely. 

Chris: But it falls down when it comes to the storytelling. You’re a hundred percent. Yep. All right, we gotta wrap this up so we can compare interest rates on our savings account! 

Gina: Oh, they’re going up so fast! They’re going up so fast, but not as fast as mortgage interest rates. The bank takes the difference. 

Chris: That’s the economy! 

Gina: That’s the economy. I really enjoy talking about this with you. If you are listening and think that we are insane control freaks, we’d love to hear that. If you—you know, have found a finance app that is—works and is amazing for you, we would like to hear from you if you use Microsoft Money Sunset Edition. My God. We want to hear from you. Please. 

Chris: Oh, please reach out.

Gina: Please reach out. If you work on a finance app, we’d love to hear from you. We love this stuff and we have a ton of opinions. Send us a note We may need to do a part two of this conversation at some point in the future. Cause I, I enjoy this one. 

Chris: Mm-hmm. This is great. 

Gina: Thanks Chris. 

Chris: Thank you so much. 

Gina: Thanks for listening everybody. 

Chris: I’m gonna go remote into my PC. I’ll—I will talk to you later. 

Gina: I’ll check the interest rate and we can continue our competition of which—which of our banks increased their rate faster. 

Chris: [laughs]

Gina: [laughs] Thanks everybody. Bye.

Chris: Bye bye.