How to Actually Use Money Apps the Right Way (According to FinTech Pros) SB1764

What if you could sit down with the people actually building the future of personal finance and just… ask them everything?

That’s exactly what happens in this episode. Joe Saul-Sehy gathers three FinTech insiders around the basement table—Peter Polson (founder, Tiller), Aaron Froug (founder, Grifin), and Ryan Ruff (longtime FinTech pro, Array)—for a rare look inside the industry that’s reshaping how we handle money.

This isn’t about pitching their products. It’s about understanding how FinTech actually works, where it’s headed, and how everyday people can use these tools more effectively. Peter and Aaron share what they’ve learned building companies from the ground up, while Ryan pulls back the curtain on the infrastructure most people never see but rely on every single day.

The conversation goes deep: What are most people getting wrong about money apps? How can you get more value from the tools you’re already using? Where is AI actually making finance easier (versus just adding complexity)? And as creators, how can they design tools that genuinely help people instead of just creating more digital clutter?

You’ll also hear their take on what’s coming next—the innovations that’ll matter in five years, the trends that are overhyped, and the blind spots the industry still needs to address. Whether you’re a FinTech skeptic or an early adopter, this conversation will change how you think about the apps sitting on your phone right now.

What You’ll Walk Away With:

• The insider perspective on how FinTech tools are actually designed—and what builders wish users understood

• How to get more value from the financial apps you’re already using (most people only scratch the surface)

• Where the industry is headed: what innovations are real and what’s just hype

• Why some tools work for some people but fail for others—and how to find your fit

• The infrastructure that makes your financial apps work (and what breaks when it doesn’t)

• How AI is changing personal finance in practical ways, not just buzzword ways

• What FinTech creators are trying to solve—and where they admit the industry still falls short

This Episode Is For You If:

• You’re curious about what’s actually happening inside the FinTech world

• You want to use your money apps smarter, not just download more of them

• You’re wondering what’s coming next in personal finance tech and whether it’ll actually help

• You’ve felt like financial tools are being built for someone else, not for you

• You want the insider perspective without the sales pitch—just honest conversation from people who live this every day

Before You Hit Play, Think About This:

What’s one thing you wish your money apps could do better? Drop it in the comments—these are exactly the kinds of insights that help creators build tools that actually work for real people.

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at ⁠https://www.StackingBenjamins.com/201⁠

Enjoy!

Our Topic: Deep dive into Fintech

FinTech past and future
Tracking money simply
Spreadsheet-based budgeting
Microsoft partnering with Tiller
Griffin’s dollar investing
Investing where you spend
User behavior psychology
Reducing clicks in apps
Decision paralysis issues
Automation for better habits
Gamification with intent
Sports betting danger
Bank data access
Plaid connection failures
Open banking friction
Security and data privacy
Checking accounts weekly
Notifications vs. batching
Micro-investing impact
Family financial conversations
FinTech community importance
Red flags in apps
AI as support tool
Fraud risks with AI
New features from each company

Our Contributors

A big thanks to our contributors! You can check out more links for our guests below.

Peter Polson

Another thanks to Peter Polson for joining our contributors this week! Learn more about Peter and Tiller by visiting Peter Polson – Tiller.

Aaron Froug

Another thanks to Aaron Froug for joining our contributors this week! Learn more about Grifin and investing in the companies where you do business by visiting Grifin – Stock Where You Shop.

Ryan Ruff

Another thanks to Ryan Ruff for joining our contributors this week! Learn more about Ryan and the financial, identity, and privacy protection tools offered by visiting array at Embedded Finance Products Platform | Array.

Check out StackingBenjamins.com/vault to get access to tools that can help you shed unwanted subscriptions, check and understand your credit, and lock down your identity.

Mentioned in today’s show

Make better financial decisions starting today by visiting Stacking Benjamins Upstairs

Join Us on Monday!

Tune in on Monday when we welcome the woman who every year helps us shine a light on the best of the best…from SlickDeals, it’s Regina Conway.

Miss our last show? Check it out here: How to Actually Listen (Not Just Wait to Talk) SB1763.

Written by: Kevin Bailey

Episode transcript

[00:00:00] opener: You heard of this thing, the eight minute abs? Yeah, sure. Eight minute abs. Yeah. The uh, exercise video Uhhuh. Yeah. Well this is gonna blow that right out of the water. Listen to this seven minute abs.

[00:00:20] Doug: Live from Joe’s mom’s basement. It’s the Stacking Benjamin Show.

[00:00:34] Doug: I am Joe’s Mom’s Neighbor, Doug, and on today’s show, you know all those cool gadgets on your phone that make your financial life. Easier today. While those other shows bring you a one, we’ll bring you two. What we’re going bigger. This just In Will apparently bring you three FinTech insiders to talk about the past, present, and future of those tools we all increasingly rely on to make better money decisions.

[00:01:03] Doug: And let’s say hello to the captain of this special episode. It’s Joe SA ci.

[00:01:13] Joe: Hey there, stackers and happy Friday. Welcome to the weekend before big Thanksgiving week, which means while you’re getting ready to go spend money on Black Friday stuff, we’re gonna help you keep some of that money in your pocket. Know exactly where it went, because we’ve got three big names in FinTech who are gonna help you do that today.

[00:01:32] Joe: So let’s meet the people that are going to be on this special episode. First of all. Let’s start with this guy. He’s a spreadsheet fan, a guru who believes that tracking beats guessing. From Tiller, Mr. Peter Paulson’s here. How are you man?

[00:01:48] Peter: I’m good. Thank you, Joe. It’s great to be in your mom’s basement again.

[00:01:51] Joe: Good. Glad you have. It’s been a while. We haven’t done as much stuff lately about FinTech, but when I thought FinTech, I thought, Peter, so thanks for joining us.

[00:01:59] Peter: Glad to be here.

[00:01:59] Joe: And then second, the guy who says you spend, so wait a minute, instead of just wearing it, why the hell wouldn’t you invest in it?

[00:02:07] Joe: Aaron Rega is here from Griffin. Griffin with one F, by the way. How are you, Aaron? Good.

[00:02:14] Aaron: I didn’t, I didn’t expect the joke from Peter, so that was funny. That was good. I’m glad to be here.

[00:02:20] Joe: Aaron, have you heard the show? I mean, come on.

[00:02:23] Aaron: Yeah.

[00:02:24] Joe: And then rounding out our triumvirate of FinTech insiders. This guy’s the bridge builder between FinTech tech and real people’s habits between banks and FinTech.

[00:02:33] Joe: From Aaron? From Aaron. What am I talking about? Aaron, he is not from you. From Array, Ryan Ruff is here. How are you, man?

[00:02:41] Ryan: Doing great. Doing great. Glad to be here.

[00:02:44] Joe: Well, let’s talk about what all three of you do first to give people a scope of really the three things I mentioned, Peter, uh, getting back to you.

[00:02:51] Joe: I mentioned that you’re all about tracking, but for the three people here that don’t know about Tiller, if they go to tiller.com, what are they gonna find?

[00:02:59] Peter: If you come to Tiller, you’re gonna find our service, which connects all of your financial accounts. Credit card checking account mortgage 401k student loan, and brings it all into your own private spreadsheet, be it Google Sheets or Microsoft Excel.

[00:03:13] Peter: And it keeps it updated every day where you can see all your transactions and balances in one place. We have a community where you can engage with others. We have helpful templates and our community does too. And it’s all wrapped in a subscription policy and a privacy posture that ensures that your data is just that.

[00:03:30] Peter: No ads, we don’t look at your data, we don’t see your data. Your data goes into your sheet where it’s helpful and insightful to you. So that’s what Tiller is.

[00:03:38] Joe: We’re gonna talk about tracking and about security today and really what’s important there, Peter, but what I find really fun is that when, uh, Microsoft money went away, didn’t they kind of point people toward you going, Hey, hey, if you love Microsoft Money, go use Tiller.

[00:03:56] Peter: Yes, yes. Well, the original Microsoft Money was a competitor to Quicken in the nineties. I was actually an intern at Microsoft back then. And then the new money in Excel was their second foray into personal finance. And it was a way to get your banking data into Excel. And it was a competitor for a few years and had us shaking a little in our boots.

[00:04:15] Peter: ’cause Microsoft is known to be a serious competitor. And then they called one day and they said, you know what? You’re doing a better job than we do. We’re gonna stick to our knitting with Excel. We’d love to send our customers to you. If they want their bank data in Excel, would you be our partner? And that was, that was a incredible fortuitous partnership for us.

[00:04:32] Peter: And we continue to have a ton of customers that we’ve won through Microsoft’s promotion, uh, who have come to Love Tiller.

[00:04:39] Joe: I can just imagine when you got that, was it an email or a phone call?

[00:04:44] Peter: It was an email that led to a phone call and I went into it. Honestly, I usually presume good intent and so, and, and I have a great history with Microsoft, but I will be honest, I didn’t necessarily presume good intent.

[00:04:57] Peter: And I said, I’m not sharing a single detail about Tiller, our operational model. There’s no way that this can go well without thinking about it. They can mistakenly as an elephant like squish us.

[00:05:07] Joe: Sure.

[00:05:08] Peter: And I was suspicious until maybe the second or the third call and then I realized that they actually, they, they say what they mean and uh, they’ve been great partners and they continue to help us as partners with Excel and to make sure that our services kick tail and works really well for Excel customers.

[00:05:24] Joe: Aaron, one of my favorite, one of my favorite of all time TikTok videos is this minister standing in front of his church and he’s talking about, you know what you’re bragging to your friends about your Air Jordans, you’re bragging to your friends about your coach purse. You’re bragging to your friends.

[00:05:39] Joe: He goes, you know, it’s real money not wearing that stuff, but actually owning it. And then to see that that’s exactly what you guys decided to do when it came in investing. Where did the idea originally come from for Griffin?

[00:05:51] Aaron: Yeah, I just wanna say also with that point of that view, it’s always give up this, to have this, I definitely think it’s a lot more positive.

[00:06:00] Aaron: You can say like, Hey, you can have both

[00:06:02] Joe: and

[00:06:02] Aaron: yeah. And instead of. I wanna take credit, but a lot of the time I give credit to my sister. So the, we were at a, a Starbucks and the barista said, that’ll be $12 for two cups of coffee. And she laughed and said, I should own stock for how much I shop here. And I think that’s kind of where the light bulb went off of like, why can’t investing just be connected to real life and fun and make sense to people?

[00:06:23] Aaron: That’s, um, and so yeah, that’s really, we, we would try to do a bunch of different ideas before and so it kept changing and that’s how it came to this one.

[00:06:31] Joe: You know how cool I’ve done that before when I’ve been shopping though, Aaron, I’m like, I didn’t wanna buy the fricking company.

[00:06:35] Aaron: Right.

[00:06:36] Joe: But really make the, I did wanna buy the company ’cause I wanna be on the other side of that transaction.

[00:06:40] Joe: So for people that don’t know Griffin, how does Griffin work?

[00:06:43] Aaron: I guess I’ll just give like a quick 30 seconds. Sure. So Griffin stands for the greatest revolution in finances. Now we built an app that automatically invests people where they spend their money. So if you go and buy a cup of coffee at Starbucks and invest you in a Starbucks stock, if you shop at Whole Foods, they invest you in Amazon.

[00:06:59] Aaron: Our whole purpose is there’s 180 million people who are still uninvested. Uh, we believe it’s mostly due to psychological reasons, like money’s tough for a lot of people. And so things like this, like I’m glad to be on this podcast. It helps people, you know, we wanna say You’re good enough, smart enough, confident enough in your own skin.

[00:07:14] Aaron: Like what if we brought joy and fun into investing and just connect it to real life? The simplicity of how it works is it just, I dunno. You download our app, you connect your favorite cards that you use every single day. Uh, you go about live your day and then our app automatically invests for you in the background and you can set a dollar per transaction or however much you want.

[00:07:34] Joe: That’s what I was gonna ask. Could it be even roundups?

[00:07:36] Aaron: So we went around and we interviewed a bunch of people and we found that setting it at $1 per transaction was actually a lot more comfortable for people than doing spare change.

[00:07:47] Joe: Yeah.

[00:07:47] Aaron: Which I was surprised by.

[00:07:48] Joe: Yeah.

[00:07:48] Aaron: But it was like, oh, okay. I made five or 10 purchases today.

[00:07:51] Aaron: I’m, I mean, this week I’m putting away five or $10. And so at least like at that $1, it just felt easier. And so we allow people to, it’s called multipliers. So you could say like, Hey, I wanna spend $5 every transaction, or $10 or 25. But one of the things that we are hoping to release probably earlier next year is sort of a, if I wanna put away like 10% of my purchase, or if I wanna set like $25 per week and allow people to customize more, or, I really, really like this company and I wanna set a certain dollar.

[00:08:20] Joe: But it’s interesting what you’re saying because I remember like, you know, often as a creator, somebody creating something new, we think, well this is what I like, or this is what I think is best. And I remember the, I remember hearing some guys at Google talking about this. Who cares what you think? Go test it.

[00:08:34] Joe: And you actually did that. You went and tested it and saw that people rather do a dollar.

[00:08:37] Aaron: We’ve been wrong a lot. So unless it’s, it’s very interesting that you like go interview, ask your customers questions, and it makes it. Wild depress.

[00:08:47] Joe: I was gonna say, I think that’s all of us in all this

[00:08:49] Aaron: stuff

[00:08:49] Joe: we do.

[00:08:49] Joe: Yeah,

[00:08:49] Peter: for sure. We’re shocked how often we ab test something and it’s, I think I have great intuition and I’m proven wrong all the time.

[00:08:56] Aaron: What is it? It’s, it’s like, but I think intuition’s great and it’s positive and like lean in with that and did just validate with data.

[00:09:02] Joe: Yeah.

[00:09:03] Peter: I was looking at Peter Lynch because you reminded me.

[00:09:06] Peter: That Peter Lynch said, invest in what you know, and that feels like it’s at the heart of what Griffin does. And you know, he was the famed money manager who helped everyone feel like they could be an investor. And he said, if you, if you’re shopping at Toys R Us, ’cause your kids are buying toys there, and this is of course back in his era, then you should invest.

[00:09:24] Peter: And I, I love it. Uh, Aaron. ’cause that’s what Griffin’s doing.

[00:09:27] Joe: I was gonna say, good analogy there, Peter, with a company that went bankrupt, by the way.

[00:09:31] Peter: I know that’s a bad, okay, that’s a

[00:09:33] Joe: What do you do? Whatcha doing here?

[00:09:37] Peter: If I, if I had doubled down and bought a Apple stock with every iPhone I bought, I would have more money in the account.

[00:09:43] Peter: So there we go.

[00:09:43] Joe: Yes, absolutely. Ryan, let’s transition to you where people have heard of Griffin or they have heard of Tiller, most of our stackers will never hear of array. And yet you’re in the background a lot.

[00:09:58] Ryan: Yeah. Yeah. Um, so array is, like you said in the background, if you ever. Go into your mobile banking app and you can check your credit score or manage your subscriptions and things like that.

[00:10:12] Ryan: A lot of times that’s array. Array builds these tools that helps extend the reach of credit unions. Um. Banks and, uh, fintechs and even podcasters and, uh, content creators.

[00:10:30] Joe: We may have an announcement about that later on in this particular episode, something that will unveil here today. But let’s not do that.

[00:10:39] Joe: As you guys can see stackers, we, we’ve got Peter, Aaron, Ryan doing three totally different things in this beautiful area of FinTech, helping you manage your money better. We’re gonna dive into exactly how to use the FinTech that you use better today. What’s the future of FinTech? Where do they think that we’re headed?

[00:10:56] Joe: We’re gonna talk about all that more, but we have a couple sponsors who make sure that we can keep on keeping on, and you don’t have to pay a dime for any of this special episode. So let’s hear from them and then we’ll be back with Aaron, Peter, and Ryan in just a minute.

[00:11:17] Joe: Peter, let’s start with you because I’d like to talk first about tracking your money and getting your money together in one place, and then let’s go invest and talk to Aaron more in the spotlight. Although guys, I want you all to, to chime in ’cause you guys know about this, not just as creators, but also of users of FinTech.

[00:11:34] Joe: But then we’ll talk to Ryan about, because Ryan’s looking at a lot of different people’s FinTech kind of about, you know, which app should you be looking at? What, what should you be worried about that maybe the average person just opening up their browser has no idea. The app store has no idea what some of the.

[00:11:51] Joe: Cautionary tales are that they should know. But Peter, it strikes me when it comes to tracking, you know, a lot of the time we think about these 500 mil, like as users, I think about 500 different things. And what strikes me about Tiller is this simple win, right? Just getting this, if I can get this one simple win, which is I can set up my budget however I want, and I press one button, right?

[00:12:19] Joe: I press one button and now all my numbers are securely downloaded. How important was simplicity when it came to designing? Tiller?

[00:12:28] Peter: Simplicity is at the core, and you’re absolutely right. There was a day where our financial lives were much easier, let’s say even before we used credit cards, and maybe when we used checks or.

[00:12:39] Peter: Checks and cash, and there was a checkbook register and there was cash and it would be really easy to keep track of it all. But now the average financial life is a bit more complex. There might be a few cards, there might be a few banks or money’s in a few places. And so keeping it simple by bringing all that information into one place has been a core part of Tiller, because if you can see it all, and, and this is even, this precedes tracking and even budgeting and there’s so many things you can do once you have it in one place, but simply seeing all your data in one place is an enormous win for a lot of people.

[00:13:11] Peter: They haven’t had that before. And that on its own, creates a level of awareness that makes everything else easier. And even if that’s the only step, that awareness is gonna make them a more thoughtful agent of their own money.

[00:13:24] Joe: It strikes me too, that simplicity’s kind of at the heart of Griffin, Aaron.

[00:13:28] Aaron: Yeah. I, I think that’s super important thing as well. It, it’s actually funny, even hearing Peter, you talk about. The importance of budgeting and like making sure you can see everything out there. ’cause it, it gives like a sense of, um, I dunno, it’s like it’s stabilization. It’s, it’s very cool what you do as well.

[00:13:45] Aaron: And I think for us it’s, it’s the ccam razors concept, like the simplest idea is usually the best with everything. And like how to just, I, and I think for us, everything that we do and build and design is also like trying to be really, really connected to real life. And so there’s a, I think the highest paid role at Apple is like the VP of Human Design and that’s because it’s like how can you take technology and make it feel real in human and like real life?

[00:14:11] Aaron: And I think money is the probably the most human thing that we like all deal with every single day. I’ve met people with the most amount of money and like other the least, and everyone still has problems and, and how they connect to it. So anything that helps make people’s lives financially better.

[00:14:28] Joe: Yeah, and I wanna ask both of you guys, and Peter, I guess I’ll start with you.

[00:14:32] Joe: You know, when you’re, when you’re designing, are you sitting like Aaron’s talking about just working through, okay, somebody sits down with a cup of coffee, what do they do next? What do they do after that? What do they do after that?

[00:14:43] Peter: One of the design principles I have is counting clicks, and I count clicks as customers sign up as as they go through their first journey.

[00:14:49] Peter: And how, because a click, not all clicks are equal, but a click reflects some decisions, some action, there’s usually some processing that they have to do. And so how can we reduce the number of clicks to get a new user from the motivation? I’m coming to Tiller and I want to get started to the ahas and the insights.

[00:15:08] Peter: That’s one of the fundamental principles we think about a lot. Because you’re right, people are busy and also when it comes to money. As they get into it, sometimes there’s a lot of things they’d rather do, you know, suddenly that laundry, they’d rather fold, which is insane because they’re like, I, I, I do, I really want to see it all.

[00:15:24] Peter: Do I really want to take this next step? And then once they do, they feel incredible satisfaction and success. But helping them through that, which means, let’s keep it simple. Let’s just get you, let’s get you through this and let’s help you book this win.

[00:15:37] Joe: Yeah. How many people, Ryan, in your experience, quote, abandon the cart halfway through signing up for apps?

[00:15:43] Joe: Are you guys able to track that?

[00:15:44] Ryan: Yeah. You know, I really like how Peter talks about these clicks. Each click is a potential failure point because people, you know, when they have to make a decision, sometimes they get decision paralysis. They don’t know if they want this or they want that. So if you can make it super intuitive, you know, automate things like, I really like how Aaron automates the fact that like, Hey, I, every time I swipe my card.

[00:16:07] Ryan: Automatically, I’m getting access to stock in the places that I love. That automation and reduce of clicks is very, very important because every point that you have to make a decision is a possible failure point. So this isn’t just for apps, but just in your own lives, you can be looking at it and saying, okay, how can I reduce my potential failure points?

[00:16:30] Ryan: Right? Like 4 0 1 Ks, opt in versus opt out. The companies that say, Hey, you are enrolled in the 401k, unless you opt out, that reduces a click, right? It’s not a decision that you have to make. So I think it’s, it’s fundamental. It’s the most important thing.

[00:16:48] Joe: Yeah. It strikes me, Aaron, that this is happening on both sides while you’re helping people by reducing the number of clicks to become investors and think about themselves as investors.

[00:16:58] Joe: You’ve got Klarna on the other side. You’ve got, uh, sports gambling apps on the other side that are also making it easier for people to lose money outta their wallet.

[00:17:09] Aaron: Yes. You know, it’s interesting ’cause that ends up being a tougher conversation. ’cause you, you look at companies like Klarna, I guess it has helped people make bigger purchases in some ways and break that down into smaller increments.

[00:17:20] Aaron: But the question is, is how much debt is that increasing on people’s side? So, yeah, I don’t know. I think for us too, it’s one of the tough things is like you’re opening up a brokerage account and you’re linking your bank and, and your credit cards as well too. And so as much as you try to make as little clicks as possible, it’s like how do you think of like building a, a good user experience?

[00:17:41] Aaron: Like it’s a real financial app that like, requires a lot of information for the government to protect people and so to make it feel trustworthy, but at the same time to make it fun and connect to people’s lives and do good things. So. I don’t know. I also like, I think, Peter, you said like earlier about like assuming good intent with a lot of these things.

[00:18:02] Aaron: I struggle when it comes to apps that I view as gambling and I don’t think that that helps people at all. But they’ve gotten really good at converting people,

[00:18:12] Joe: so Good. I wanna talk about gamification a little bit later, Aaron, but you brought up something ’cause I think gamification is a huge piece of this, right?

[00:18:19] Joe: Whether you’re helping people save or you’re helping people spend gamification. Just that that user experience is huge. But you mentioned the idea of. You know, people, when they use Griffin or Tiller or any of the array products, they’ve gotta trust you enough to take out their credit card, their bank statement, their whatever, and hook this thing up.

[00:18:38] Joe: I know talking to other people, I talk to, uh, Jesse Comb Peter, a guy that you know over at, uh, YAB consistently, he worries about something. I’m sure that you, Aaron and Ryan all and it’s plaid, kind of sucks and makes your life hell, according, according to Jesse. And I know as a guy that uses your platforms, you know, you’ll go on and all of a sudden it’s been unhooked and then people get mad at you, Aaron, because it unhooked.

[00:19:07] Joe: And, and it’s not, it, it isn’t necessarily your fault. Like what’s, what’s going. Can you explain to our stackers what’s going on in the background when you’re trying to work with these third party providers to get money? Where I want it is a stacker and you want it as the guy trying to help me invest, but these middle people are driving us crazy.

[00:19:27] Aaron: Yeah, it’s one of those like, I don’t know if double-edged sword is the right answer there. Yeah. But it, it’s sort of the thing where it’s a, we are heavily reliant on it, especially like when you’re a startup in a tech company and, and trying to grow, like, for example, to, to do what Plaid is doing and then to do what our broker dealer and clearing firm does in the background, we need to have hundreds of millions of dollars and be a multi-billion dollar company.

[00:19:50] Aaron: And so a lot of companies in the world, even if you connect to Vanguard nowadays, you can use Plaid to like connect to your accounts to fund it. But we have definitely learned that no matter what goes wrong, it’s Griffin. It doesn’t matter any third parties that we have. But Plaid is like basically a, a large institution that genuinely has built their business around being able to connect to bank accounts, to get transaction information and to link banks in sorts.

[00:20:18] Aaron: But they have to build a solution. Like say there’s like 7,000 credit unions and banks. They have to build a solution. Every single one of those banks has a different technology. And that bank can say, I wanna make sure that this connection for like purposes of protecting data, ’cause I don’t trust this connection, it’s gonna delete and de-link after six months.

[00:20:40] Aaron: And another bank could say two years and another bank could say one month. And so then that ends up happening. And then Plaid has to send us information that says this de-linked. And then we have to go to our customers and be like, Hey, this de-linked, you have to reconnect it. And then the customers say, why doesn’t your app work the way that it’s supposed to?

[00:20:58] Aaron: And it’s,

[00:20:58] Joe: you’re saying it’s not even necessarily plaid’s fault. It could be the institution on the other side’s fault

[00:21:03] Aaron: 100%. And a lot of them are, I’ll say this nicely, very outdated in their technology. And most banks don’t want to have in the US. Open data and transaction, they don’t actually wanna give data back to the users or for other third parties like ours who are trying to help people get invested.

[00:21:25] Aaron: Um, I, I’m not trying to talk poorly about it, it’s just true. Yeah. I’ve been to conferences and that’s all that they talk about is like how scared they are. But then you also have to think about it from another end that those banks are scared that if their data comes out, that the larger banks, like Eva Peter was saying earlier about, you know, building a product that’s, that could be competing with Microsoft, that the larger banks get access to that data and then they steal their customers in these small community banks that are trying to, so I think everyone’s just trying to survive.

[00:21:53] Aaron: But the problem is, is that like the things that we are reliant on, so example, like our broker dealer in clearing firm, if let’s say a user has an a CH return and our broker dealer in clearing firm decides that that’s a risk, then they will limit an account. And then we have to go and then say like, Hey, let’s.

[00:22:14] Aaron: Unlock this and like make sure it’s not a risk. ’cause they’re like, oh, but what? But is this return because there’s fraud. And so you try to protect people.

[00:22:22] Joe: Yeah.

[00:22:22] Aaron: So it’s a lot.

[00:22:24] Joe: I wanna define a couple of these terms because I realized even before I ask you the question, Aaron, I realized I didn’t tell people kind of what’s going on in the back end.

[00:22:31] Joe: So stackers, there’s this, there’s this company called Plaid whose job it is to connect Peter’s errands and Ryan’s products to your app. And so Aaron, you said it nicely, you know all these thousands of banks and plaid is one company trying to get them all to interface nicely with a solution that you’re trying to use on the other end.

[00:22:52] Joe: And so you’ve got all these different moving parts because of that. And then when it comes to the broker dealer, which is these are the people that actually hold your stocks or your funds for you. When it comes to them, they’ve got a bunch of rules they have to follow. So when Aaron said a CH, which means if they go try to get the money, the money’s not there, and it bounces.

[00:23:12] Joe: They freak out that this is a fraudulent account, and so everybody’s protecting themself from the bigger banks and their competitors, but they’re also protecting the stacker from other fraud outages. I know Peter, you guys decided to go kind of next level with your security. Was that just to try to get around this whole mess or why the, the move hopefully away from plaid, if at all possible.

[00:23:36] Peter: That’s a great question. Yeah. At the core, we want our customers to have really easy access in getting all their data in one place. We realized it was so important. We actually support two aggregators. They’re the two leading aggregators. We support Plaid and Yodlee. So we give customers a choice and we also support CSV imports.

[00:23:54] Peter: So if they have a bank that’s not supported by either Platter Yodlee, they can download the CSV and throw that into Tiller, and we make that easy. There are a few things going on for Tiller. We have read-only access, so we can’t move money. We don’t want to move money. We just wanna show you what is happening with your money.

[00:24:11] Peter: There’s a move afoot that JP Morgan started this summer and they announced that they were going to start adding fees if aggregators like plaid and, and services like Tiller wanted to access Chase banking data. And it’s really upsetting because. It is certainly reflects the banks having a fear that if there are apps that have easy access to that data, they’re gonna be disintermediated.

[00:24:37] Peter: The reality is Chase is a great bank. They do a great job holding customer money. They have their own apps and services, but customers sometimes want other apps and services. You know, when we have our. Phones and we take a photo. Sometimes we want that photo just in the photos app on our phone, but sometimes we wanna share it.

[00:24:55] Peter: And sharing with your iPhone or your Android phone is simple. It’s free. And it works effectively with thousands of apps that can take those photos and do cool things with it. And Apple and and Google do not add surcharges if you want to take your photo out of their ecosystem and share it with another.

[00:25:12] Peter: And so for JP Morgan, the largest bank in the country, 800 billion market cap, for them to say, we’re going to start adding fees and friction. If customers want their data on their money, I think it’s a huge step backwards and it’s concerning ’cause it is not in the interest of customers. Ultimately, customers are gonna be served by easier access and more transparent information.

[00:25:34] Peter: It’s a step backwards, so it remains dynamic. And we are pushing hard to make sure customers have access for their data on their money.

[00:25:43] Aaron: I was just gonna say, I’m sitting here, my body’s getting hot. I like, I, it’s literally, it’s your data. Also, the biggest thing of me is like I’m putting my money in a bank where that bank is federally protected of how they loan out my assets, that they make money on, that when I, that I’m earning zero interest on when the federal funds rate is high enough that I could be earning a few percentage points on the money that I’m saving.

[00:26:12] Aaron: And I think that’s one thing with our app as well too. We are, I’m, I feel very, very fortunate. So I’m, I’m gonna show off a little bit, but, but at, by the end of this year, we should have like over one and a half million installs on our app. And like, to me though, that’s an indication that this is genuinely something that people want and can like, help them.

[00:26:31] Aaron: And I think like the same thing Peter, with like what you’re doing as well too, and Ryan, like powering the back end of all of these financial apps is like in taking away the power of people to get help, to manage their own money, to feel invested, to feel safe. Like at a time when we all need to feel safe financially.

[00:26:49] Aaron: It shouldn’t. And like I think in like many other countries, there’s open data when it comes to the financial institutions and that’s like a really big thing for people. I don’t know, I don’t know why that gets me so bad. I just feel like people deserve better in all of this.

[00:27:04] Joe: I, well, you know, I mean, this is nothing new, right?

[00:27:06] Joe: I’ve said for a long time that when. I was failing with money. My bank, bank of America was there handing me a shovel so I could get even, even worse. Trouble like, Hey man, you can dig faster than this. Not dig my way out, but get in even worse. There. There’s something else. Ryan, let’s talk conspiracy theories for a minute.

[00:27:22] Joe: We were joking actually before we, before we start talking about a different conspiracy theory, which will not make the air unfortunately, although it was a lot of fun. This one was something, Peter, that you said, and Peter, you said this nicely, but I’m gonna put some snark on this. All right, I’m gonna put a little tension on it.

[00:27:37] Joe: You said that Chase is great at holding your money, and I’m wondering, Ryan, how often is this really protecting the customer as much as it’s messing with plaid, so that, and unhooking these apps on purpose so that maybe Chase gets people to stop using them so much.

[00:27:57] Ryan: I mean, one takeaway that I would have as a stacker is how am I evaluating the bank that I’m banking with?

[00:28:04] Ryan: And it used to be that you evaluated your bank by all, it’s down the street from me and, and you know, they have this checkbook program or whatever. But one of the things that people that are smart are looking at when they decide where they want to bank is how well does this bank play with other tools?

[00:28:20] Ryan: Like, are they promoting open banking? Are they detractors from open banking? Because there are other banks out there that are saying, Hey, we play nice. They’re directly connecting with Plaid. They’re directly connecting with Yodlee, and they’re making it easy for their customers to get the data out. So they’ve taken this different approach where they’re saying, Hey, we want our customers to have access to their data.

[00:28:44] Ryan: And the banks that are doing that. The, the play there is if we make our clients happy and provide these other tools, they can potentially build goodwill and have better relationships with their customers. So it’s absolutely true that this is a big problem and it’s, I’m just as frustrated as Peter and Aaron that, that some of the banks are dragging their feet and trying to add friction.

[00:29:07] Ryan: But the silver lining is there’s other banks that are taking an opposite approach. And you can really get ahead when you’re working with a company or a bank that’s gonna help you connect to other apps.

[00:29:20] Joe: Yeah, it seems very short term and obvious, and a mentor of mine told me a long time ago, guys. He said, uh, always think long term and not so obvious.

[00:29:28] Joe: Don’t think short term and obvious, and that is paid mightily and hopefully over the long term we stick with these partners that actually respect us. Alright, the second half of today’s discussion, we’re going to focus on investing and really habit building, which also goes for what Ryan and Peter are focused on.

[00:29:47] Joe: But I wanna talk about this, this idea again, that every little bit matters. Does a dollar matter? How do you convince somebody that saving just a dollar is going to help them move forward when we know as people have been in this for a long time, it helps a ton when you help people change these little behaviors.

[00:30:03] Joe: We’ll also talk more about behavior sciences. We’re gonna talk about ai. How’s AI changing the game for all of you? We’re gonna hear the one more time from our sponsors than the rest of this podcast is sponsor free. So we’ll hear from them and we’ll be right back.

[00:30:19] bumper: Hey, this is Joe Crane, host of Veteran on the Move Podcast.

[00:30:22] bumper: And when I’m not helping veterans transition to entrepreneurship, I’m Stacking Benjamin’s.

[00:30:28] Joe: Well, now that we talked about security and locking down y your money, actually, Peter, before we move into investing, I wanna ask you one question that I had in my docket here that I really need to ask. You get to see lots of data.

[00:30:42] Joe: You said it’s read only, but you get to read and look at the data. How are people using, not just Tiller wrong, but when they’re either trying to track their expenses or they are setting up a budget where they making a big mistake that we could help ’em fix? Right now,

[00:30:57] Peter: when you say, uh, you see the data, that’s really you’re referring to the customer.

[00:31:01] Peter: ’cause again, at Tiller, the team at Tiller, myself, the rest of the team, we don’t see our customers transactions and balances. But when a customer sees their data, that’s when the magic happens. Of course, the biggest mistake is not staying engaged and it’s really simple. But the biggest mistake is. Letting everything else in life get between you and an awareness of what’s happening with your money.

[00:31:22] Peter: The fact that that subscription’s renewing this week, the fact that that your spending is light or is heavy, just an awareness of what is happening. And it’s so easy to just get distracted by everything else and check out for an A week, turns to a month and a month turns to several months, and you get to the end of the year and you don’t actually know where your money’s gone.

[00:31:42] Peter: You know actually very well what you’ve made. Most people have a very precise sense of what they’ve made, but then at the end of the year, you’re like, why is there not more in my account and why have I not made progress towards my goals? If they do nothing else but just stay engaged and get into their data once a week, they’re gonna make progress.

[00:32:00] Joe: Back when I was a financial planner, I’d have people guess, how much money do you think you spent on restaurants last year? Then we’d go and we’d look at the number and it was often three x what they, what they thought they spent. Even better yet, I would ask them, how much money do you think you paid in taxes last year?

[00:32:17] Joe: Because you could see that, you know, right at the year end. And that was generally, they would guess about a third of what they had paid in taxes. That’s interesting. You know, Ryan, that brings up for me the idea of notifications, right? Like as a. Provider. Then I hear what Peter says and I think, okay, if I’m a creator who’s doing my job, I’m gonna notify my end user to say, Hey, you know, it’s probably time for a good check-in.

[00:32:43] Joe: And yet I know in my life more I turn off notifications, the better, the better my life is like the interrupting pattern. How in FinTech do we get around the annoyance of notifications, but still set up reminders to check in? Assuming you agree with what Peter’s talking about?

[00:32:59] Ryan: Yeah, I do agree with what Peter’s talking about, and I think that with technology, and we’ll get into AI and some of these other things later, but I think batching is really important when it comes to behavioral psychology.

[00:33:12] Ryan: Like setting aside a certain time each week that you’re going to do X or certain, you know, and you talked about, you know, even just investing a dollar. I think that works in a lot of things like in health and fitness. If I tell myself I’ve gotta wake up and run five miles, I’m probably not gonna do it.

[00:33:29] Ryan: But if I’ve committed that I’m gonna run a hundred yards, I can do that. And then that first a hundred yards at when I get done with it, I’m like, okay, I can keep going. But to address your specific question here about notifications, that interruption it is difficult. But I think if you batch these things, and it depends on, you know, we talked about reducing clicks, but when the clicks do have to happen, if you can batch them all together, I’m gonna make this decision, this decision, this decision, and then I’m gonna automate a couple of things here so that it’s going to, over time, it’s, I can start automating some of these processes and I make these decisions once a week or you know, every few days.

[00:34:12] Joe: So important to have that type of, to just think about our own, uh, anatomy and how switching tasks is such a bear, so batching. I’m a hundred percent. Uh, love that. Aaron, let me ask you the question you, you must hear at Griffin. Okay. So I save a dollar, I invest a dollar. That can’t be that big a deal. What do you say to that?

[00:34:34] Aaron: Yeah, so I’m just gonna show my own account. This is a dollar at a time. I’ve been using our app for like three years now. And

[00:34:42] Joe: by the way, for people that are audio only 19,000, $95 and 69 cents.

[00:34:47] Aaron: Yeah. So I’ve been able to put away $19,000 for myself. I own 137 companies and I’m at a 320 weekly streak. It adds up.

[00:34:57] Aaron: You can see like the transactions that you use, all the, the time and the places that you’re shopping at. I’ll say you, you asked a question earlier of like sometimes what can get people. I will say the biggest thing is, one of the differences, like especially when you’re using the app as well, is I use Chase as my funding source, but my main card is an American Express.

[00:35:17] Aaron: So a lot of times we’ll see that like customers will only connect Chase on our account and then they’ll be like, why is Chase not working? And it’s, but they realize that like, well, you know, later on American Express is the main card. So it’s to making sure that it’s like to use an app to the best of the abilities is to connect the things that you use every single day.

[00:35:36] Aaron: But it adds up over time. And also for a lot of people, it just feels good to like set money aside. And some people use it for, I mean I, my hope is long-term investing. They use it for like long-term and life events and those sorts of things. Like that’s sort of the intent of this. But I don’t know, you’re putting away $25 a week.

[00:35:55] Aaron: That can add up as well. A lot too.

[00:35:58] Joe: You bring up something. To me that’s something I think that a lot of people avoid while you guys are helping people reduce clicks. I often have gotten then into the, the spirit of, okay, I’m gonna do a couple clicks and then Aaron, your app is just gonna work marvelously on its own.

[00:36:12] Joe: But this American Express versus Chase point, I don’t even realize, I haven’t hooked up the account where I’m spending all my money, so nothing’s moving the way that I, that I want it to move. How important is it for somebody who’s using Griffin to go in and use, I noticed you have a whole education area on your website, I would guess that’s hellishly underused.

[00:36:35] Aaron: Yeah. A lot of the times it is.

[00:36:37] Joe: Yeah.

[00:36:37] Aaron: So I know we’re gonna talk about like AI and stuff, but I think we’ve made like over a hundred plus articles help articles on through our entire website that people can use and we have a, we have like a 16 day educational campaign when people sign up and you get emails coming in.

[00:36:51] Aaron: One of the jobs that we need to do better at also is to put this information within the app itself, the educational app. ’cause not a lot of people reach out and we’re looking to create, uh, customer service, AI and a chat bot AI so that you can just call in and instead of having to read through a hundred articles, just ask a questions.

[00:37:08] Aaron: It’ll read through the a hundred articles for you and like help give out the answers. But it’s really underutilized.

[00:37:13] Joe: But if my goal, Aaron, I mean I understand you’re taking responsibility and your goal is to reduce friction. Yeah. But I don’t know having the other side of this, if I’ve decided that I wanna use Griffin in my life, I mean, let’s actually use it.

[00:37:26] Joe: Let’s open up the 16 emails and figure out how the hell to use it best from the people that make it Whose goal is the same as mine? Your goal is the same as mine. I want more money in my account. You want me to have more money in my account? Let’s actually use the things that creators put out there.

[00:37:42] Aaron: It is very underutilized.

[00:37:43] Joe: It’s so frustrating. And I know Peter talking to Alice from your team at FinCon, who’s a badass, by the way, one of the newer members of the Tiller family talking to Alice, her job is kind of to hopefully get more people involved in the Tiller community. Not because, I don’t know, sell ’em more stuff. It’s It’s because you’re gonna use Tiller better if you are surrounded by people that are using the product Well,

[00:38:08] Peter: no, it’s true.

[00:38:09] Peter: And if you share stories and you share templates, you share ideas, you help each other. A lot of people feel alone. They have a lot of emotions around money, and they also feel like they don’t know as much as they should, even though they actually are likely better than they’ve assessed. I was thinking of a story that actually connects Tiller and Griffin because our son was.

[00:38:26] Peter: SA has been saving money. And so we check his tiller sheet. We meet each week and he’s been seeing his balance grow. And then he recently, and I’ve been, I’ve been enjoying the satisfaction of seeing him grow as a saver. And then he recently, he said, I’m gonna make a purchase. ’cause he was at a friend’s house and his friend had a one wheel, which is this $700 electric little, little scooter thing.

[00:38:46] Peter: And I’m like, oh boy. First we have a waiting period. If it’s $50, you wait a night. If it’s so $700, you’re gonna wait 14 nights before you spend it. It’s his money, he can spend it. He went through the waiting period and then I was trying to throw more friction into the process. So I’m like, Hey, hey, do you know what this would be when you’re my age?

[00:39:04] Peter: If you spend that $700? And he actually. To my surprise, he guessed it, it would be $10,000 at a 7% annual return, and so that was more friction, more conversation. He ultimately made it. It’s given him a ton of joy and I see that. I think for him, this was the right purchase. But I love what Griffin’s doing because it is that, it’s the corollary.

[00:39:23] Peter: I have my money to spend, I have my money to invest. I can do both, and how do I want to spend that next dollar? Understanding the trade offs and how we think about our money is a huge unlock. We have choices. I can not only spend on something differently. I can not spend entirely. I can put it in a savings account in an investment account, and you have that money grow in 10 years or 20 years or more.

[00:39:44] Peter: It’s

[00:39:45] Joe: funny, Ryan, we’re talking about these little things, but truly. As a creator, how do you get people into the community? If you’re a creator, how do we convince stackers that, you know what, these people that don’t want, I don’t have time to go at any meetings. I’m thinking about the comedian talking about I don’t have time to join a club, and yet if we actually use it.

[00:40:05] Joe: I feel like to some degree, what you guys do separates people. It doesn’t naturally build community because I feel like I could do it myself with my thumbs. How important is it for you to build community?

[00:40:18] Ryan: Community is huge. It’s everything Jim Rohn said. You are the average of the five people you spend the most time with.

[00:40:24] Ryan: People have said, you know, the suit makes the man, right? The thing is, if you have a community of people that are all doing something, you’re more likely to do that thing. I think that that community doesn’t necessarily need to be homegrown within the FinTech. Like right now, we have the stackers community, right?

[00:40:45] Ryan: And we’re learning things about how to use. Griffin, we’re learning about how to use Tiller better. This is the community. And you look at companies like, um, you mentioned Jesse Mecu with YA Man. They’ve got a great community of people that are just.

[00:41:01] Joe: I, I think it’s called

[00:41:01] Ryan: a cult about why,

[00:41:02] Joe: think it’s called a cult, right?

[00:41:03] Joe: That’s

called,

[00:41:04] Ryan: you know, cults aren’t all bad. Maybe that’s my hot take, right? You know, if you join the right cult, but no, um,

[00:41:10] Joe: that’s what we’re gonna call this episode. Cults are All Bad just to get Clicks.

[00:41:15] Ryan: That’s a good title. But no, I think that you look at, um, companies like Monarch have done a great job of partnering with coaches and content creators to have this community, and the community teaches you how to use the tool.

[00:41:29] Ryan: So I think that, you know, you’re doing it right and people are joining their favorite podcast. They’re getting linked in, and I think that the, the real future is somebody that’s got a trusted voice that builds a community like the Stacking Benjamins community, and then they partner with cool apps that help their community get from point A to point B.

[00:41:52] Joe: I wanna switch over to talk about gamification, which, uh, Aaron, you brought up a little bit later. You know, Robinhood got in big trouble for gamification by having confetti come down every time people did the wrong thing by putting more money on margin, which was just drove me crazy. But how much, Aaron, do you think about if my app is more fun, people are gonna use it more often?

[00:42:13] Joe: How does a creator think about gamification?

[00:42:16] Aaron: Yeah, so I’ll, I’ll kind of give an example of some things that we try to use, because I think what I was talking about earlier on was that we try to connect a lot of things to real life. I think gamification can be very positive when it’s like you learn through action.

[00:42:29] Aaron: ’cause that’s one of the biggest things I always say is that, you know, when I was younger, my dad would always try to tell me every single way to ride a bike. But the one way you learn how to ride a bike is you ride it and you’ve, you figure out how you do and you make mistakes. And that’s sort of how all of this happens.

[00:42:42] Aaron: And so, like in our app itself, for example, the stock market’s closed right now and that’s why it’s night mode. There’s stars in the sky. So like you can learn about things through real life. And when the stock market’s open, you know, it’s a bright blue sky with clouds and everything. And the gamification of the weekly streaks.

[00:43:00] Aaron: Like we, we only try to do positive things. If you’ve invested for yourself this week, we take that off of Snapchat or du lingo, things that people already recognize, like you earn a streak. A lot of this comes back down to intent. And so like, if it is to get people to put and invest a ton of money that they don’t have, I’m a big, big believer still that that’s our whole thesis is like, if, if you’re gonna be spending anyway, at least take care of yourself a little bit.

[00:43:26] Aaron: But the incentive of gamification and, and for this is to create long-term investing. How do you reward good behavior? But it is important because it, it’s what makes things more engaging and connecting and educating. Like even if you do a walkthrough in the app. At the very beginning, that’s gamification.

[00:43:46] Aaron: But that teaches people things. Like we’re trying to record a video that’s like a, uh, I don’t know if you’ve ever seen the, like the safety videos when you get on a rollercoaster, we wanna do something fun like that and then like gamify the process of setting up your account the right way. So, I don’t know, I, it’s a word that to me, it’s based on intent.

[00:44:07] Ryan: I wanna second that and I wanna say, so I spent some time at Duke in their behavioral psychology research lab, and I got to, I, an incredible experience. I got to work with Dr. Dan Arieli, one of the world thought leaders specifically in this space. And I asked him point blank. I’m like, I, I saw how powerful gamification really is.

[00:44:26] Ryan: I said, is this ethical what we’re doing? We’re we’re basically manipulating people. And I said, is this ethical? And he said, whether we do this or not, however the product is designed, it’s going to trigger people’s biases and it’s gonna trigger ’em one way or another. Coming to Aaron’s point, he said, it’s all about the intent.

[00:44:47] Ryan: You know, people are out there in the world and they’re being manipulated by the way, the government’s structured things. They’re being manipulated by way, the way the marketers are structuring things. And if you have good intent and you’re building your thing to gamified towards the gold, that’s gonna help a stacker or help someone to, to get to their goals.

[00:45:07] Ryan: That’s the important thing. And so I want second one, Aaron saying about the intent. And so if we, we know what that intent is and we know what that gamification is leading us to, that’s the important thing,

[00:45:18] Joe: which is a struggle. Then. I mean, knowing what the founder’s intent is, are they helping, are they not helping What you’re saying, Ryan is, I mean, Klarna is out there gamifying how to spend more money more quickly.

[00:45:28] Joe: The sports betting apps are helping us. I mean, my relatives, I was saying on Peter’s podcast that we recorded a few days ago, I’m watching my relatives bet on how long the Star-Spangled Banner’s gonna go. They’re betting on the coin flip like stuff that just drives me. Yeah. A hundred percent crazy. I’m like, are you just trying to give money away?

[00:45:47] Joe: What are you doing with these bets? And they think it’s really fun because you know, DraftKings has gamified it so much. Seems like a blast. It seems like a great time.

[00:45:58] Ryan: And the way we think about that at Array is it all comes back to, we don’t even call content creators, content creators anymore. We call ’em Trusted Voices.

[00:46:06] Ryan: That’s what we’re calling. The podcasters and the content creators because that’s, we believe is their job and their role in the ecosystem is to be that trusted voice and to be someone says, Hey, here’s a cool app. Here’s I’ve vetted it at for my community and this is what it does and here’s why it’s great, right?

[00:46:24] Ryan: So that’s where we believe that the content creators come into this space as being that trusted voice to help the community know, try this app, not this one.

[00:46:33] Joe: How did we pass that test, Ryan? Like, what the hell happened there? You used to get like an exception.

[00:46:38] Ryan: I think it was one too many drinks at FinCon, and then we just kind of add on one thing led to

[00:46:42] Joe: another.

[00:46:42] Joe: Oh, what the hell? Let’s let them in too. All these other people are trustworthy. Aaron, I asked Peter this earlier about budgets and about tracking and where people get it wrong when it comes to investing and what you do at Griffin, you get to see a lot of data. Where are people getting it wrong?

[00:46:58] Aaron: Are you saying like using the app or

[00:47:00] Joe: either one

[00:47:01] Aaron: using in general and,

[00:47:02] Joe: and yes.

[00:47:02] Joe: Either one of those.

[00:47:04] Aaron: I think after seeing this for a really long time, I’m gonna go maybe a little bit deeper here. I believe a lot of this is systemic. I think there’s only five states that require financial literacy courses. The average person develops a relationship with money at 16. If you look at still the average person who starts getting invested in the us, it’s a 3-year-old white male with a $60,000 salary.

[00:47:28] Aaron: It leaves a whole lot of people out. And when you’re already starting off with not feeling good about something, that’s why a lot of the time people don’t want to be connected to it. What I’ve had to realize, even for myself, even for our company, is like knowing where you stand as scary as it is, is really helpful.

[00:47:51] Aaron: And so again, like Peter, like what you’re doing, I think that’s really, really great for people. ’cause it allows them to know where they stand because at least when you know where you stand, it makes a difference. So I’d say like what we’re trying to help with. That’s why it’s like bringing joy and fun into it.

[00:48:05] Aaron: It’s like, and it’s not really gamification or negative, it’s just like, can you enjoy something that normally sucks? Because if it’s fun and it’s positive, then maybe you’re more willing to spend more time with it and then allow it to see, have a different feeling about it. And so a lot of people use our app to just set it and forget it.

[00:48:24] Aaron: It is true, our app is fully automatic. It’s connected to real, like the lives that people live and they’re automatically investing. I would say people will be more successful in their personal experience if they are able to like be more engaged and learn and read the articles. But the question is, is like how to build that positive relationship.

[00:48:45] Joe: Well, that’s interesting because I love how your answer models Peter’s or is really similar to Peter’s, which is the check-ins. The check-ins are important and, and I can imagine for a lot of people, Aaron just saying, no, I am an investor and letting people go from this is all bad, or this doesn’t connect to me or my community.

[00:49:03] Joe: And, and the fact that it’s a dollar at a time can make it so easy for people to change that.

[00:49:09] Aaron: One of the things that we’re trying to do is communicate ownership and what ownership means. Like you’re already spending money. Somebody once said to me that it’s the concept of owning the world that you’re helping build, like you’re putting your money towards there every single day.

[00:49:24] Aaron: Like why not have a, a benefit and be a part of it as well too. And so we’re trying to create some AI videos right now. We’re trying to keep it human. We’re trying to do both. But where it’s like we have somebody walking into a McDonald’s and they’re given a robe. And some slippers and they’re getting a massage and they’re saying, you know, thank you for being an owner, but I genuinely hope we create that world.

[00:49:46] Aaron: I want one day, like somebody sitting in 35 B at the very back of an American Airlines flight in the middle seat and they get a blanket ’cause they have stock that like we are all treated better because we we’re all helping moving this world forward.

[00:50:01] Joe: That’s so fun. That’s so,

[00:50:02] Aaron: yeah, it just comes with it all.

[00:50:04] Joe: That’s so, so fun. I think AI stuff, definitely helping brands make their points better. We’ve had some, some real fun brainstorming with AI’s help.

[00:50:13] Peter: Ryan, I appreciated your, your inquiry when you were in the lab at Duke. It goes back to the question too about. Which bank are you using? And does this bank have my interest in mind?

[00:50:23] Peter: I think as operators, as founders, I think we have to ask ourselves deeply what are we trying to do here? And I know F Tiller, that’s crystal clear. We’re very mission driven. Everyone on the team is very mission driven. We wake up and think about our mission, and that ends up being a superpower for attracting the right team, but also for serving our customers.

[00:50:44] Peter: But I think as a consumer, you’ve gotta make that decision yourself. If you’re a stacker, you’ve gotta look at each company and each bank and say, what is their mission? Are they gamifying with my success in mind, or are they gamifying with their success in mind? And you ultimately, and that’s, that’s something I actually think a lot of snackers are pretty well equipped to do.

[00:51:06] Peter: And it’s increasingly important because if you’re playing someone else’s game, you better opt out. But if you’re playing a game that’s helping you succeed, that’s pretty powerful and you have to make that call yourself.

[00:51:18] Joe: Ryan, let’s focus on a couple of things that I think, ’cause you get to see, while Peter is hyper-focused on Tiller, Aaron’s hyper-focused on Griffin, you are focused on a lot of different companies stuff.

[00:51:30] Joe: What are some of the red flags that you’ll advise people to watch out for when it comes to either downloading FinTech apps or diving into the next, uh, product in their browser?

[00:51:42] Ryan: It depends on the person. You know, if you’re an early adopter and you’re looking to try the coolest new thing you can maybe try out a new app that is, uh, not as proven.

[00:51:52] Ryan: But what I would do is I would look at the reviews in the app stores, look at those, but then also. Piggyback off of somebody else’s trust. You know, to me it always kind of comes back to community. And so I would say join a community, be engaged in that community and see what apps that they’re recommending and using and having success with.

[00:52:15] Ryan: That’s if you’re a general person, but if you’re a pioneer and you’re going out and trying new apps that are a little bit out there on the cutting edge, you need to make sure you gotta read the fine print and make sure that they’re, um, properly following the SOC two compliance and, and some of these protocols.

[00:52:34] Joe: Is there something specific we’re missing in the fine print?

[00:52:37] Ryan: Um. That’s a tough one. That’s why I push back to the community. ’cause there are a lot of FinTech apps out there that are operating kind of in the wild west and they just haven’t gotten caught yet. And to some degree that’s okay. You look at early startups like Uber, in the very beginning they were breaking rules around having these crazy taxis out there that weren’t regulated.

[00:53:04] Ryan: You look at the founders of, uh, Venmo, they were having massive, massive fraud problems in the beginning and they ended up getting bought by a company for 25 million. Uh, it’s called Braintree was the company Brian Johnson. He started Braintree, they got bought for 25 million. He cleaned up their whole process, all their fraud and compliance issues, turned around and sold them to PayPal for 300 million like a year later.

[00:53:31] Ryan: Right? Because he had cleaned up so. There’s not one thing. You’ve gotta trust your community and probably not be an early adopter of things unless you are familiar with the space.

[00:53:44] Joe: Let’s talk about that big elephant in the room before we say goodbye, which is this idea of ai. I’d love to hear how are you using AI to change the game?

[00:53:53] Joe: And Ryan, since you’re, you’re front and center, let’s just stick with you. Where are you using AI and kind of where do you see it headed in the, in the FinTech space?

[00:54:03] Ryan: I think that AI is going to make. Huge changes in the space, but I think that because this is such a regulated area, it’s more gonna be in personalizing tools rather than completely reinventing tools.

[00:54:17] Ryan: So like, you know, if you’re trying to understand how to use a tool, things like that, maybe like chat bots and things like that, that are gonna get smarter about answering questions. But I’ve vibe coded, I guess you call it three or four apps myself, that you, you, you can complete an app in a weekend, but these apps are not compliant.

[00:54:38] Ryan: They’re not, you know, gonna, could really change the game. I think where I see ai, it’s just an information tool that’s gonna make it quicker and easier to get up to speed in using apps.

[00:54:51] Joe: Peter, how are you guys using AI at Tiller and where do you see it headed?

[00:54:55] Peter: We use AI extensively to just allow us to do our work faster and better.

[00:55:00] Peter: Internally. We use it with our customers. If you call in and write in for support, AI is often gonna give you a faster answer. And if you are categorizing your transactions, a big thing about Tiller is we want you to categorize your transactions your way based on your unique categories, and AI’s been really helpful for that.

[00:55:20] Peter: So there, there are a lot of future unlocks. For us. AI is an incredible way for people to feel savvier when they feel stuck. So if they are deeply in debt or if they’re figuring out how, where should they invest their money now that they can start investing? Or if they’re wondering, should I be paying off my mortgage faster or should I be putting that money into an investment account?

[00:55:43] Peter: AI is actually one way to democratize some personal finance information and to give people some good sound advice based on generally sound principles. You have to treat everything with a grain of salt because you, you’re not always gonna get a great answer and you need to be suspicious if, if it’s not.

[00:56:01] Peter: But in general, for people who are, want to get smarter, whether you’re a really confident learner or whether you don’t feel very smart about money, I think it’s also a big enabler there as well too. And we’re continuing to look at ways to connect those dots as our customers are looking to get smarter.

[00:56:18] Peter: And we have, we’re a trusted partner with their financial information, so we have lots more planned with our roadmap.

[00:56:24] Joe: Does the customer see AI on the front end? Like, can you ask a Tiller AI tool to look at your spreadsheet or look through your, your data?

[00:56:33] Peter: That can happen in a few ways. So, uh, Google and Microsoft have both built AI in alongside spreadsheets.

[00:56:39] Joe: Oh, sure.

[00:56:39] Peter: That’s of some value. Uh, it’s not a home run yet. And then again, if you’re reaching out to support and you’re on our website and you’re using our chat bot, you will see you have an option to engage with AI and you’ll get an instant answer that, that if it’s helpful, sends you on your way. And if it’s not, then we have a live real person who will follow up when they’re available.

[00:56:58] Joe: Yeah. The thing I worry about now, and I’m sure that you guys worry about is Robert Farrington at the College Investor Big Personal Finance website. They did a study on AI with personal finance, and the number of answers that you get that are wrong are just still really disturbing, like super duper duper disturbing.

[00:57:16] Peter: Yeah. Again, I think there’s definite caution advised, but if you’re looking at it not for the definitive answer, but you want to start having a conversation because. A lot of people don’t have someone that they trust to sort of share their details with. And so if you want to start having that conversation, you can.

[00:57:33] Peter: And then yeah, you should track down and do your due diligence before you actually follow that advice. But it can generate insights and questions that you should then verify, which is a great point before you put them to work.

[00:57:43] Joe: That’s what I like the brainstorming partner Peter, like what can I do with this and give me five options or whatever That’s right.

[00:57:49] Joe: Is huge at Griffin. Aaron, what are you guys, uh, doing with AI and where do you see it headed in the future?

[00:57:55] Aaron: Yeah, I’m also a firm believer right now that it can be wrong a lot of the times and especially if it’s coming to investment advice, like we’re not there yet.

[00:58:05] Joe: I’ve seen some

[00:58:05] Aaron: painful investment

[00:58:06] Joe: advice.

[00:58:06] Aaron: Yeah, there’s gotta be like regulation or something there. But I will say if you can upload a knowledge base into it, and that’s where it’s basing. So like for example, the thing that we are building right now is we have the hundred articles. We wrote that we ran through compliance, that we did this entire thing.

[00:58:29] Aaron: That if you can take those a hundred articles specifically, say this goes into a knowledge base that then somebody can call a conversational AI tool with when they’re setting up an account and like, Hey, what is plaid? Why do I connect my funding source? Or why do I connect transaction accounts? What is, you know, SIPC insurance, like giving an ability to at least have some context around it and confidence and people, I would love to have a 10,000 person customer support team that people can call.

[00:59:01] Aaron: It’s very, very expensive. I think also when it comes to investing in tools, you know, we charge $5 a month or $36 a year for our service. Obviously, like it’s, I don’t know, I, I’m trying to say this without saying it because I, I know for a lot of people that can be a lot of money. At the same time, it’s a very, very little amount of money and so to like be able to hire a ton of people and to offer the service that we are like.

[00:59:24] Aaron: Buying one share of stock back then and paying a brokerage fee of five plus dollars for one share

[00:59:29] Joe: every

[00:59:29] Aaron: time, or buying thousands and thousands and thousands of shares for like micro shares for people like in a year and automating a full service and connecting their accounts. And we’re paying for all of this.

[00:59:39] Aaron: Like it’s a, um, I’m trying to say this the right way, but it’s to be able to offer these things, we have to be as sustainable as a business. And so I think that what AI in some way is helping, is giving people support and access to a potential knowledge base in a way that’s easier in the way that they want to receive it.

[01:00:01] Aaron: While again, I’m still saying be cautious about it, but I think it’s allowing companies to accelerate their ability to help people in unique ways at the same time internally as a business. Like I use it all the time.

[01:00:15] Joe: Yeah.

[01:00:15] Aaron: Um, obviously like, you know, I, I get concerned about my, my data and stuff being protected.

[01:00:21] Aaron: But it’s been super helpful. There’s both sides of it.

[01:00:24] Joe: I love the idea though, of limiting the knowledge base. You know, if it’s a knowledge base that you put together or Tiller put together, or Ray put together and, and, and it’s just crawling your stuff to get the answer quicker, like that’s a beautiful tool that bridges the gap between, you know, more of a company the size of Griffin.

[01:00:40] Joe: And, you know, we talked about Chase with bajillion people. I think the numbers of bajillion people work for Chase. That’s,

[01:00:46] Aaron: I think

[01:00:46] Joe: that’s what I, that’s

what

[01:00:47] Aaron: I’ve heard. Yeah.

[01:00:48] Joe: AI told me that, that number. Ryan, how about you?

[01:00:52] Ryan: How are we using it? At Array?

[01:00:53] Joe: Yes,

[01:00:55] Ryan: we’re using it internally quite a bit. Externally.

[01:00:58] Ryan: We’re not using it yet. We’re kind of allowing our partners to, to use it in the way they want. But yes, we’re not using it externally at, so

[01:01:06] Joe: there’s nothing, there’s nothing customer facing, just building the tools quicker.

[01:01:10] Ryan: Yeah, it just kind of helps with writing code for some of our newer stuff, and then we’ll obviously have a person to come through and and check it, but it just helps them go a little bit faster.

[01:01:22] Joe: Do you see that becoming customer facing?

[01:01:25] Ryan: I do, but I, it’s just too early to make predictions on this. I think AI is such a wild card right now. I think it’s super helpful for me in certain places, but it’s also, it’s just not reliable enough in others, and so it’s, it’s too hard to know. I think it’s too hard to predict right now.

[01:01:43] Joe: I think it is the Wild West and that’s kind of the, it is kind of the fun of AI right now. Yeah. I’m watching these videos that look like they’re real people talking to each other, and then you halfway through the video, they’re like, oh my God, none of this is real.

[01:01:55] Aaron: You realize it.

[01:01:55] Joe: It’s, it’s, yeah.

[01:01:56] Aaron: There’s this like very viral video I think of something of like rabbits jumping on a trampoline.

[01:02:01] Aaron: No one had any idea was ai.

[01:02:03] Joe: It’s so

[01:02:03] Aaron: scary. It had like 60 million views. I think like that’s also where one day, like not being able to discern between like what is real and, and what is not real. But I guess we’ll get there.

[01:02:14] Joe: We’ll see. We’ll see what

[01:02:15] Peter: happens. I think that it also, and this is a topic for another show, but I think it’s increasingly challenging for consumers to know what they can trust.

[01:02:24] Peter: ’cause the, the opportunities for fraud are, are easier than ever. And so you can get a phone call that sounds like it’s your relative and it sounds convincing and it’s their voice and it’s not. That’s just one of many different variants that that is way easier now. And so I think we all have to just be also on guard.

[01:02:42] Peter: And that’s something stackers know, but it’s never been more true.

[01:02:46] Joe: I think that’s a great place to leave it because the fraud problem is huge and coming, coming faster. It’s weird. We put all these size safeguards in place, right? And yet the people trying to tear them down move everybody’s just this arms race.

[01:03:00] Joe: Yeah. Going on.

[01:03:01] Aaron: It’s intent. It all comes back down to that. Like there’s beauty in like what AI is creating. At the same time we have to be aware of the other side.

[01:03:07] Joe: Yeah. Yeah. You can’t not play. What is the intent?

[01:03:11] Aaron: Yeah.

[01:03:11] Joe: Let’s find out what’s happening at all of your companies. What’s going on? What’s kind of on your mind, Aaron, what’s going on at Griffin?

[01:03:18] Joe: Anything, uh, cool that our stackers should know about as we move into the holiday season?

[01:03:23] Aaron: I’d say there’s two things. Recently we started, uh, doing quizzes that are doing really well. So people are like really engaging in the quizzes, like we wanna teach. I think that’s positive gamification. We’re teaching people about investing through quizzes, and we’re having super high engagement there.

[01:03:37] Aaron: Second, we found that a lot of our customers are our parents.

[01:03:40] Joe: Well, wait a minute, where do we get in on the quizzes? Tell us about getting in on the quizzes.

[01:03:43] Aaron: Oh, it, it’s coming every week through email. Oh, sweet. If we’re a Griffin, a Griffin user. Even if you just like register with us and you’re like, not even, you can just learn about investing through our quizzes every week.

[01:03:53] Aaron: So it’s been, that’s cool. It’s been fun. We’re looking to build that in the app. And then I think the second thing is, um, a lot of our customers are parents. It’s close, but a majority of our users are female as well too. Parents, grandparents, they get excited about this and our wine share with our kids. So we’re building family plans so that like the whole family can use the app and have a conversation and be like, Hey, where do we shop today?

[01:04:13] Aaron: And, and get to have those conversations. So we’re super, super excited about that. And we’re also, I can’t like announce this, but we’re, we’re releasing some pretty cool features soon over like the next month or two and. We do wanna do some cool things with like the shopping and the holidays as well.

[01:04:28] Joe: The number of times I’ve talked to FinTech founders over the years that have said, I got something else I really want to tell you about, but I can’t.

[01:04:37] Aaron: Yeah, you’ll see it.

[01:04:39] Joe: That is awesome.

[01:04:41] Aaron: Yeah.

[01:04:41] Joe: And you [email protected]. We will link to it in the show notes at stack your Benjamins dot com as we will tiller. Peter, what’s coming up, uh, at Tiller? What do you guys got going on?

[01:04:52] Peter: One of the things I just mentioned earlier in our show is continuing to work to make it easier, more reliable, more robust to get all your data into your spreadsheet.

[01:05:01] Peter: And that we’ve made some awesome advances this year with multiple aggregators and other tools. We also have made some really exciting innovations around using mobile with your spreadsheet and not just through the spreadsheet app on your phone, but through a Tiller web app that allows you to see in a really simple way your transactions and your balances.

[01:05:21] Peter: And that’s something that we have in beta and we’re continuing to refine and improve. And I’m really excited about because it means you can have access to all of your trusted, secure information when you’re not at home and when you’re not at your computer. And we also. Coming up the holidays are a huge time for us.

[01:05:38] Peter: It’s specifically New Year’s actually, because for many people, that gives them the unlock to say, all right, the new year is a time for me to get into my finances. So we’re, we’re heads down getting ready for that. And we’re working on some new webinars and new educational opportunities to help people.

[01:05:53] Peter: That hits on some themes we talked about earlier, but we know customers are thirsty for help and thirsty for feeling community with others who are sharing similar goals. And so that’s something that we are developing as we speak and we’ll be sharing more around the holidays as well.

[01:06:09] Joe: My favorite tiller activity at the end of the year is almost like, you know, Spotify.

[01:06:13] Joe: I use Spotify and it gives me my Spotify unwrapped. I like at the end of the year, opening up my spreadsheet and I compare it this year to last year. Ooh, restaurants won. Joe lost, or, Ooh, travel increases to take more of the budget. Gasoline pump, not so much. Uh, you know,

[01:06:29] Aaron: just. Can I say something?

[01:06:31] Joe: Yeah.

[01:06:32] Aaron: That is something we’re building.

[01:06:34] Aaron: So I think it’s super cool for people to be able to see like, Hey, here’s all the brands that you invested in this year, and here’s where you shopped at the most and the things that you’ve done. I love Spotify wrap so much,

[01:06:44] Joe: Aaron.

[01:06:45] Aaron: I, it’s more complicated than people think to build. I, we are trying to create that.

[01:06:48] Aaron: Yeah.

[01:06:48] Joe: It is, it it is really super fun though. I love it. It’s super cool. Yeah. Doing that with my spreadsheet, but I don’t know. Aaron, do I wanna see Taco Bell like that much on the No, I’m, I’m joking.

[01:06:59] Aaron: We’ll hide that one for you.

[01:07:03] Joe: You mentioned McDonald’s. I’m like, oh, your number one spot that you bought stock in McDonald’s life might be,

[01:07:12] Aaron: might help with it.

[01:07:12] Aaron: It lets you know though, right? It, it does sets the, instead of avoiding it

[01:07:16] Ryan: awareness.

[01:07:17] Aaron: Uh, it’s awareness. If I know and I’m like, okay, I probably shouldn’t be eating as much at McDonald’s.

[01:07:22] Joe: Yes.

[01:07:22] Aaron: Like, yeah, that sucks. But it’s like. It helps. So, you know, I like,

[01:07:27] Joe: oh, gee’s, doctor told him, oh, gee’s, doctor told him right, that you should say more, less.

[01:07:32] Joe: And he’s like, what does that mean? You know how at the restaurant you say more do that less? Like, that was his, that was his weight loss plan. Uh, yeah. I gotta stop a fourth meal. Uh, Ryan, what’s going on at Array man?

[01:07:46] Ryan: Well, well, well, we got some exciting stuff going on. So we’ve been

[01:07:50] Joe: working, Steve, we need a, we need a drum roll here.

[01:07:54] Ryan: Yeah. We’ve been working with a lot of content creators to help their communities to understand their credit better, to protect their privacy and to understand their subscriptions and to figure out where they’re wasting money on subscriptions. But then also to be able to understand. What tools they should be using and would benefit them the most.

[01:08:17] Ryan: So even within the stacker community, there’s some people that are gonna be more interested. Their top of mind is, man, how can I budget? How can I budget better? And maybe they need to be pushed over to Tiller. And then there’s gonna be some people that saying, man, I just need to get investing. I finally need to do that.

[01:08:34] Ryan: And they can be pushed over to Griffin. And so even within the stacker community, we’re going to be launching in conjunction with Stacking Benjamins, some really cool tools. And I don’t know if you wanna announce those yet or if we wanna say coming soon, but they’re coming soon.

[01:08:52] Joe: Hopefully they’re released by now.

[01:08:53] Joe: But in, in an abundance of caution, because we’re recording this early, head to stack your Benjamins dot com slash vault and you will see us helping you with your subscriptions, learn about your credit and lock down your identity. And we’re doing that with, uh, Ryan’s wonderful team at Array. And by the way, the behind the scenes stuff that you guys do, this is my first, uh, foray into this.

[01:09:16] Joe: So for Peter and Aaron, like I had hair before we started working with Array. I’m, I’m kidding. All my hair was. I I didn’t have any white here. It was, it was well, but there is significantly more going. Got a few, Ryan got that from working with me, uh, every week. Alright guys, well, again, thank you so much for your knowledge and for mentoring our stackers today.

[01:09:38] Joe: You’ll [email protected] will also, by the way, link to this in our show notes page. Remember, it’s one F-G-R-I-F-I-N. Peter, thanks a ton to you as. You’ll find tiller.com and w you won’t see array. They’ll be in the background as usual. But if you go to Stacking Benjamins dot com slash vault, you’ll see what we’re building with Ryan and his team.

[01:10:00] Joe: So you’ve got it from here. Doug, what are our three big takeaways from today’s discussion?

[01:10:06] Doug: So, what’s stacked up on our to-do list for today? First, take some advice from our FinTech guests. Paying attention to these cool new innovations can make your financial life easier. Second, ai, that’s only gonna increase the pace of change in the marketplace.

[01:10:22] Doug: So set some time aside, maybe once a quarter and dive deeper into how your favorite apps are changing. But the big lesson, don’t tell Joe’s mom about what’s going on at Tiller Griffin and Array. She’ll insist that was a comedy act she saw in the sixties. Thanks to Peter Paulson for joining us today. We like Tiller so much that we’ve partnered with them.

[01:10:48] Doug: Head to Stacking Benjamins dot com slash tiller to check them out. Thanks to Ryan Ruff for hanging out with us today. His company Array is our partner for our new app to help you shed subscriptions, get on top of your credit and make better money decisions. Head to Stacking Benjamins dot com slash upstairs to make better decisions starting right now.

[01:11:10] Doug: Thanks also to Aaron Frug for joining us today. Wanna try out investing in those companies you do business with? Check out Griffin. That’s Griffin with just one [email protected]. This show is the property of SB podcast LLC, copyright 2025 and is created by Joe Saul-Sehy. Joe gets help from a few of our neighborhood friends.

[01:11:34] Doug: You’ll find out about our awesome team at Stacking Benjamins dot com, along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello. Oh yeah. And before I go, not only should you not take advice from these nerds, don’t take advice from people you don’t know.

[01:11:52] Doug: This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I’m Joe’s Mom’s neighbor, Duggan. We’ll see you next time back here at the Stacking Benjamin Show.

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