Mastering Money Management: Jason Leong on Bootstrapping PocketSmith and Empowering the Home CFO

0:00 Chris Titley: You're listening to a DayOne.fm show. Hi, it's Chris Tittley here and welcome to Fintech Fun. Today we're— we've got Jason Leong, CEO and co-founder of PocketSmith. Jason, thank you so much for being on the Fintech Fun podcast.

0:16 Jason Leong: Hey Chris, thanks for having me on. It's great to be here.

0:18 Chris Titley: Not a problem at all. We're sitting here late July 2025. Jason, PocketSmith, for those listeners out there that have zero idea about the business, What is it?

0:29 Jason Leong: So PocketSmith is software for the home CFO. We're a personal finance management tool that is available online. We're in 190 countries and our customer is what we call the home CFO.

0:40 Chris Titley: Excellent. Now Jason, PocketSmith, I got 2 questions about this. One, when did it start and why did it start? And two, PocketSmith, the name.

0:49 Jason Leong: We are, we're pretty long in the tooth actually. We were founded 17 years ago in 2008. I think this is before fintech was even coined as a word. It's back when SaaS was, you know, still application service provider. And you know, that ages us a little bit. And yeah, we were founded here in New Zealand. We're a New Zealand company still. Australia's our biggest market. And we're founded in this very house, the one that I'm living in right now. We are a bootstrapped garage-style startup that's turned into a company. And we still are very much a humanist company as well as a fintech. And the name, I guess, speaks to that. So, you know, finding a name for your company is probably one of the hardest things you have to do. And getting a domain for it is probably the second hardest. So we wanted something we could pronounce and something that didn't seem too fashionable at the time because in 2008, people were dropping letters from their company names and contracting them. And we just wanted something that people could spell easily. So pocket is a way of describing money, really, like pocketbook, or if I'm out of pocket. And a smith is a maker, it's a creator, like a goldsmith or a silversmith. So a pocket smith could be looked at a number of different ways. It itself, the product, is a pocket smith, something that helps you craft things with your money. Alternatively, you are the pocket smith. Mm-hmm. You know, you're the person taking control of your finances and, and shaping the future that you want.

2:25 Chris Titley: Fantastic. So 2008, obviously a pretty rough time in the world when it comes to money and financial, um, you know, the GFC, etc. But then you also had 2020, which again put a lot more spotlight on personal balance sheets. And even today with the cost of living and interest rates, etc., huge focus in Australia and broadly speaking around the cost of living. What does PocketSmith actually do, I suppose, to give users a little bit more comfort around their money?

2:52 Jason Leong: So we talked about the home CFO, and we often think that the unsung hero of the family, they're the person who, you know, either by choice or just by the fact that they're the only person willing to do it, stand up and take control of the household finances, pay the bills, do the planning, the strategy, the budgeting. And data is the lifeline of the home CFO as it helps them make accurate decisions. The problem we are solving though is that financial information is really hard to get and really hard to interpret. So if you think about how much time it would take for the average person to find out how much they've earned and spent over 3 months, say, it's a simple answer, but it could take hours of fiddling with statements, spreadsheets, and calculators. I mean, I know this for a fact. I helped my mom, she's 75, find out this information from HSBC in Malaysia. And we had to go through a bunch of PDFs and it took me 5 hours. So I often describe the pain point like this. It's like you need to know the time, but you first have to build the clock yourself. And we're seeing a huge gap here, not just in terms of efficiency, but in terms of what people are happy to put up with, which is just a, you know, this is just gonna be hard and it's gonna be a grind. So that's why we made PocketSmith. It's there so that you have the financial answers at your fingertips. And it saves you time and effort.

4:13 Chris Titley: And Jason, when it comes to personal financial management or PFN, which people talk about, the acronym probably wasn't around in 2008, more fashionable now with acronyms, but there's a lot to unpack. There's a lot to unpack as a user that potentially has a bank account. We've got a more, you may have a mortgage, you might have, you know, obviously recurring expenses, but then you might also have superannuation. You might have cryptocurrency. You might have, you know, a whole lot of different types of assets and expenses, et cetera. How does it all piece together?

4:44 Jason Leong: Well, I suppose what you're talking about here is your entire net worth and your big financial picture. So what we actually do, I mean, we didn't start this way and I can go a little bit into our history, but what we do today is we connect to over 14,000 banks and financial institutions worldwide. So we're a truly global product and we let people link up their accounts to see their data in near real time. So that you've got the whole picture. The main thing though, something we often take for granted is that this data that is often at our financial institutions isn't really owned by us because they could expire your statements after 3 years or if you change banks, it's all gone. So the idea of having a PFM pull your data down, we are extremely privacy-focused. We really believe in the ownership of your data. That's one of the things I know we're gonna be talking a little bit about the CDR in Australia, but this is one of the things that we firmly believe that, you know, you know, this data that you're generating through your finances really does belong to you. It contains incredible insights about who you are, where you've come from, and it helps you decide where you're gonna be. And so, you know, it's really our mission not just to educate people about the value of this data, but to give them access to it and to give them ownership of it. So ultimately, even if you retire your Pocksmith account, you can export all of that out of it. The main thing is that you've got it somewhere. Yeah.

6:07 Chris Titley: And when people think about the CFO, like, is there a bit of education around what a CFO does to a household in terms of the role that you take on? Is there also some understanding around prompting and changing behaviors and/or understanding it, or are you just the person that says, here's the data, you just do what you want with it?

6:30 Jason Leong: I think, well, I think with our segment of customer, they're the people who already have a degree of willingness and ability to take on the finances. So the thing that a lot of, I guess, older financial institutions don't understand about PFM is that it too should be segmented. So oftentimes you take a look at what the banks are offering, for example, you know, on their mobile apps. Yes, it is a simple PFM. Yes, it could be used by everybody, But people's finances are arguably a lot more complex, a lot more nuanced, and everyone is a unique and individual case. They've got hopes and dreams of their own, they've got their own ambitions. And so where we sit is at a tier of customer that realizes that they need more control and they have very specific things that they want to do with their money. And so we look at the Home CFO as being broken down into 3 key categories. There are the budget planners, so people who track incomes and expenses and they aim for goals like debt repayment, financial independence. And then there are investors, so people who monitor their net worth and looking to build wealth. And then thirdly, digital nomads, so often balancing freelance work with travel. That's quite a new thing, I suppose, over the last 5 years that use case has exploded. And these people seek freedom and self-determination through financial clarity. So by putting a product up there that broadly serves these key categories, someone will step into the product and know exactly what they want to find out from their money, and they can use our features to build the picture that they need. But beyond that, we've also built a platform that changes with you. And certainly, you know, over the last 17 years, my own personal finances have changed, my goals have changed, my life has changed, but the platform stays the same.

8:23 Chris Titley: Absolutely. No, I agree. And if you can grow with the platform, I think that's very important. Like for instance, there's, you know, other apps in Australia that have— with pocket money apps, et cetera. And pocket money is a time in life when maybe it's 7 years to 15 years old, but then you get a job and pocket money gets dismantled, et cetera. But getting a full landscape of one's household budget and one's budgeting, et cetera. How important has it been to sort of, you know, use data sources, and we can talk about CDR integration. You mentioned that integration, that's a huge amount of integrations that you have. And how is that possible? And I suppose, has there been any pushback from vendors saying, no, no, we're not going to release your data, it's our data and shouldn't be PocketSmith's, etc.?

9:07 Jason Leong: Yeah, that used to be the case for sure. It still is largely the case here in New Zealand. So we're about 5 years behind Australia in terms of the CDR. The UK came live first, I guess what it might've been, they started talking about it in 2015.

9:22 Chris Titley: Yeah, I was gonna say a decade ago.

9:24 Jason Leong: Yep. Yeah, yeah. And so I guess the answer to your question is that it depends on the region. So if you're looking at Australia, Australia has a very well-implemented CDR and it gives us the ability to work with the financial institutions because it's legislated that this data belongs to consumer. And through a number of secure channels and through, I guess, vetted providers, we can get the data securely. The key thing is the notion of consent. That being, in the old days, people were prompted to enter their passwords, their online banking passwords into the product in order for the product to scrape that data from the institutions. So that was inherently unsafe. Even though there are very few recorded instances of hacks happening this way, the risk is certainly still there. So a better system is where the customer of the finance, at the financial institution provides consent via the institution. So it says to the bank, I'm gonna allow Pocketsmith to access my data. And so when it asks, let it have it. But then the customer can at any point revoke that consent as well and say, okay, I'm done using that product. 'Please don't let them access my data anymore.' As opposed to, you know, 'I gave PocketSmith my online banking details and I don't know how to get them back except, you know, changing my password.' Mm-hmm. For what it's worth, we've never collected online banking passwords either. So it's very, very dicey when it starts to get to that point. And you know, in this day and age, security is really paramount, you know, with AI and hackers and people masquerading to try to get your money. So yeah, so to go back to your original question, yes, it can be difficult in certain regions where there isn't a CDR and data reliability and fidelity remains an issue because there hasn't been a set program or a set format for that data to be pulled in. So there's a lot of work that goes into acquiring the data, sanitizing it, and then making it usable for the user. Australia, really, you know, it's one of our favorite markets because of the work—

11:39 Chris Titley: I was gonna touch on that, the Australian market per se post-COVID.

11:42 Jason Leong: Yeah.

11:43 Chris Titley: There's obviously, you were probably one of the pioneers, I would say, in the buy now, pay later segment in Australia.

11:49 Jason Leong: Yeah.

11:50 Chris Titley: A different way to pay, rightly or wrongly, whatever your view is. They've had some enormously successful companies in that segment. Australia as a nation for PocketSmith, I mean, you're, I assume, born in New Zealand. Where does Australia sit and how important is it for you?

12:07 Jason Leong: It is our biggest market. And it's, I mean, not just because of proximity, I guess, but our product just appeals to Australians and it has grown organically. So it had been growing quite well prior to the CDR, but when the CDR opened up and we could actually deliver better services to Australians, more reliable services through a better consenting process, you know, things just started to move very quickly. We've started to understand a little bit more about how Australians think about their money. It's fantastic. Australians are curious about their finances. They love thinking about ways to improve their situation. They're comfortable talking about their financial wealth, their health, sorry, and wealth. And it makes the whole process so much more engaging and fun. Kiwis tend to look at money as still a bit of a taboo topic. And you know, it might be related to the size of our country. And perhaps how timid we are as a population, which is not a bad thing, but it does mean that the way that we approach both markets is quite different.

13:14 Chris Titley: I'm curious to know the emotions that people get and the feedback that you get from customers about money because, you know, you had things like Afterpay and you can like, I'll just Afterpay it. And then you have digital banks where the experience you know, like Up for instance, might people go, oh, this is quite fun and interactive. But at the end of the day, you know, some people don't want to look at their balance sheet on a Monday morning after the weekend. Some people don't want to look at their balance sheet on a month-to-month basis because they've had bill shock.

13:46 Jason Leong: Yeah.

13:47 Chris Titley: How do you manage those emotions to sort of put Pocket Smith out of it?

13:51 Jason Leong: Yes.

13:52 Chris Titley: It's not our fault. We're just providing you with the data, but also You know, there's some things you can do to make sure your relationship with that particular emotion of spending too much or having the guilt, et cetera.

14:05 Jason Leong: Yes.

14:05 Chris Titley: Plays out of it.

14:06 Jason Leong: It really does come back down to segmentation. So fortunately, we don't actually hear from a lot of customers who are finding it a grind. Years ago, probably what we'd see online was, hey, you know, I've signed up to PocketSmith and holy crap, I'm just freaked out. Look at my finances. I didn't see these things. But that's a, you know, hey, thanks for the vote of confidence. We're glad we're, effecting change. But so fear is one thing.

14:29 Chris Titley: Yeah.

14:30 Jason Leong: But as we've grown and we've positioned ourselves for the home CFO, we don't hear often from people who say that, "Oh, it's a grind," or, "I don't want to get up and do this." Really, they already know that the work needs to be done, but they're really happy that we've taken the amount of time out of their day to get it done. You know, we've seen research that indicates it costs a household about 300 hours a year to do their personal finances, which includes paying bills and looking at your statements and whatnot. But when you use something like PocketSmith, we could really reduce this down to 5 or 6 hours because everything's really at your fingertips. Sometimes we just have users log in once or twice a year to export their statements for their accountant so everything's up to date for them. There is a bit of a running trope, we've seen it from a number of sources where there's a fireplace and a glass of wine and PocketSmith. So it's sort of a Netflix and chill type situation except you're doing it with your personal finances. And that's something we really embrace.

15:32 Chris Titley: Interesting, interesting. Yeah, I'd probably not look at my finances over a glass of wine and a fire, but anyway.

15:38 Jason Leong: It does ease you into the process really. I can't say you make the best decisions with a glass of wine by the fire.

15:45 Chris Titley: And through the journey of PocketSmith, I'm interested to know around the features that that it offers and the types of feedback that you have got and whether you've sort of tested a few things that it hasn't worked and tested a few things that it has worked and the feedback you get and how you deal with that. Hmm.

16:00 Jason Leong: Well, the product is actually very different to what we started with. So back in 2008, the genesis of the idea was me having bought my first house and experienced a change in my disposable income. I just needed to understand when I could afford to travel to see my family again. Seems like a simple question to ask, but the answer really lies in, well, what's in a cash flow projection and how do we get to that point? I had an idea to then put my money, my upcoming incomes and expenses into a calendar. So I knew when things were scheduled to come in and go out. And then I wrote a script to calculate the running balance of my bank account at the bottom of every day. So if you imagine a grid view calendar, you could, jump forward 6 months and you could see how much you're going to have at any point in time in the future. So I thought this was actually quite a bit of fun because it's interactive. It's not a spreadsheet. It's looking at my finances in the context of my days and of my life and my activities. And I thought, well, this could be a product. If it works for me, it could probably be a lot of fun and be really useful for a bunch of people out there. So that's when I got together with my co-founders and we built a prototype of it and added a graph to the top. So while you can see the numbers in the calendar, you could also look at a graph that runs, you know, a year or 2 years into the future and just see your projections. So what we had built inadvertently was a cash projection tool for the consumer. We hammered that out in 4 weeks, got an early alpha feature out there, And what gave us the confidence to keep moving was, you know, out of a small flat in the city of Dunedin here in the cold south of New Zealand, we managed to get a call with a Silicon Valley investor. You know, he was managing a launch event and we thought, let's just take a punt and see if we can actually get it in there. What he— we did get a call back, which is rare. And he said, look, this is not ready for launch. Obviously, you've just hammered it together. But I just wanted to tell you guys that I would have used this when I was really broke. And we thought, okay, look, you know, we've managed to reach Silicon Valley from New Zealand. It can't be that hard. So let's keep working on it. So we released the product after 3 months and very quickly got feedback from our users. And the first thing we learned was that personal finance isn't a one-size-fits-all problem to solve. So we had this lens of creating a cash projection. And we thought that, you know, this could help everybody. But the feedback we got back was, hey, you know, this is great, but we'd like to understand what we're actually spending our money on right now. I was quite adamant that I didn't want to have to deal with bank statements or any of that accounting aspect of it. But it was a resounding request from our users. And so it took us the remainder of the year to build out a file import feature, a list of transactions, reports, and everything else. So the product really has, and it continues to change based on the customer feedback. So I guess to answer your question, you know, the first cut of the product wasn't what the market wanted. And even the second and third cuts were still quite, I guess, you know, we were still learning what the market needed. We didn't have these direct automatic bank feeds. Until 2010 or 2011. And so that's like 3 or 4 years after we launched the first cut of our product.

19:44 Chris Titley: Wow. And then in terms of the direct bank feeds and the categorization, et cetera, and you just touched on that point there. Like I've tried to budget in the past and it's a bit difficult. And the reason it's difficult, I think, is because of these one-off type expenses that you don't budget for and you put it in a miscellaneous, you put it in like a, category, like, okay, it's a rainy day, we'll need some money, et cetera. But then they become more frequent and less miscellaneous. As an example, you know, like the dog went in for surgery the other day, you know, it wasn't expected. My wife had a flat tire. It wasn't expected. Then you go in and they go, actually, there's two flat tires.

20:22 Jason Leong: Yeah.

20:23 Chris Titley: The car needs an extra service at the 40,000 versus the 30,000. But that the $40,000 is $300 more than the $30,000. So you put in $400 for a car service, but then it comes out at $800. And then you're like, okay, I'm sick of this miscellaneous thing going up. And then you might have 3 at once. You might have a sick, a sick child or something happens, or like there's a, there's an annual bill that comes in from life insurance or something like that.

20:50 Jason Leong: Yes.

20:51 Chris Titley: How do people, do people keep tinkering with PocketSmith to kind of get it right or how right can it end up being?

20:58 Jason Leong: Absolutely. I mean, our advice really is, so people do tinker and again, there isn't a one-size-fits-all solution, right? So it really depends on how you visualize your money and we're not there to be prescriptive about how you do it, but we've got the category structure for you to be able to either create a flat version or something nested. My advice typically is to keep things as simple as possible. So Auto-categorization is really great, but you know, when you plug in your bank transactions and in comes 30 different categories, it can be quite overwhelming. Typically, if I were to do a rewipe or a, and I often do with my finances, I might start with 6 or 7. And for your, you know, again, the miscellaneous stuff, I would put that into a big bucket and then watch for the stuff that falls in that category and then average that over time. And that gives me an indication that, look, I think I need an emergency fund. That probably weighs in at about maybe $1,000 a month or $1,000 a quarter that will catch that slush. So the main thing is just understanding those patterns to begin with. The categorization piece is it can be a bit of a folly because it is a task. And so when people think about categorization, they're like, okay, if I do this, I'm going to be better at my money. It really isn't though. It's just a— Yeah. A kind of a vehicle to get you to what you need. And the thing is, as humans, we like to look at jobs that have to be completed. And so categorization is a nice one where we go, okay, everything's got a category and it's all filed away. But it's actually quite cool to take a step back and go, all right, can I just, how many different ways can I cut this?

22:38 Chris Titley: Yeah.

22:39 Jason Leong: We do have a feature in PocketSmith that handles what we call rollover budgeting. So this is where you've saved up money. And if there's money that is unspent, so you might have budgeted $500 for groceries, but you came in at $400. Instead of resetting your budget to $500 the next month, we rolled $100 over. So you know, you've got $200 to spend for the next month instead, or you can reallocate that surplus into something else. So that's, again, another, another type of tool that people use to figure out how to reallocate money from their budgets. But for me, I mean—

23:18 Chris Titley: Really interesting in terms of that, in terms of vendors as well. I mean, obviously, you know, you can go to a coffee shop and you get a flat white for $5.50, but then you go, hold on a second, there's one down the road that's offering for $4.50.

23:29 Jason Leong: Yeah.

23:30 Chris Titley: And then you go down and then maybe at the end of the month you're like, oh, there's the extra $50 a month, which I hadn't ordered. What was that, $50 a month, maybe $20 a month, whatever.—

23:38 Jason Leong: Yes.

23:39 Chris Titley: —saved, or by having a coffee at home, and you can actually visualize that. I think that's a good dopamine hit for people to go, actually, how much have I saved? You know, and, but the $20 goes to something else, maybe. Yeah.

23:49 Jason Leong: Yeah, yeah. It depends. So if you've got a competitive mindset, so where you, if you like to game yourself and you've set yourself a target with a little bit of a gap, uh, then you're, you're winning. And it's a really lovely way of looking at it. For me personally, uh, I like to keep track of just where my bank balances are. So if it's bringing debt down in terms of my mortgage and seeing that number get smaller or seeing a savings account get bigger and looking at the points in time. So this goes all the way back to day one of PocketSmith or even before that when I thought, okay, if I need $5,000 to get flight tickets and accommodation and all of this in order to go and visit my family, when am I gonna hit that number? If I follow these budgets, as I've laid them out for the next 6 months, this is when I'm going to achieve it. And I might come in earlier or later, but that gives me— So that's how I look at my goals. And that's one of the challenges that we've got at PocketSmith because people visualize their goals very differently. Some are big, some are small, some are short and long-term. So everyone's got a little thing that sort of switches in their head that gets them going, gets them excited.

25:02 Chris Titley: Yeah. I'm also curious to know whether that's changed in the last little while, maybe some de-identified data that maybe the mortgage or the deposit on the house is not as achievable anymore and people have scrapped it and gone, right, you know, I'm never going to buy a house, so let's go on a holiday.

25:18 Jason Leong: Yeah, I think, I mean, certainly people are a lot more open to different ways of living, particularly when One could say that sometimes the deck is stacked against the younger generation entering the market. And it's something I'm not particularly happy with, thinking about the opportunities that I had some 20 years ago to buy a house and how housing is a commodity nowadays that just prices a lot of people out of the market. The value really isn't there. But on the flip side, again, silver lining, We're seeing, so like just thinking about the sort of people that we thought we would serve with PocketSmith when we founded the company. When we were students, we were like, you know, the students would never use our product because we have been there. We could afford to be broke. And the last thing we want to do is actually to look at managing our money. We just want to get beers and get messed up and finish our degrees and go into the workforce. And so for the longest time, we thought, well, the younger generation is not really one for our product. It's, it's got to be people moving through life stage changes in their late 20s. Again, house, kids. But to your point, things are changing. And what we've seen, which is very encouraging, is that the Gen Zs are particularly clued up about their money because there's never been a better time to be financially educated when you're young. Yeah. And to participate in commerce and the ability to earn. There's so many different ways to earn and spend today that we never had the opportunity to do so when we were younger. And so as a result, we're seeing younger people save a lot quicker and build up really good financial habits. And so that's opened up Poxmith to a whole new market that we never thought would exist. Mm-hmm. So yeah, that's encouraging.

27:14 Chris Titley: Yeah, that's a very interesting point about the dynamics around budgeting. Like, I mean, it wasn't a word in my vocabulary probably until, you know, 25 maybe. I don't know, I can't remember, but it certainly wasn't at 18, you kind of, you work, you spent, right? That was kind of—

27:30 Jason Leong: Yeah, yeah.

27:30 Chris Titley: There was no kind of—

27:31 Jason Leong: It makes us sound like cavemen.

27:33 Chris Titley: I remember going back to when I was 18 or 19, I used to referee basketball And I remember just doing it at 8 o'clock on a Saturday morning and he'd finish at 3. And then that sort of like, it wouldn't be cash, but it'd be sort of pretty instant the next week. And you'd be like, you get money in and you're like, well, I've worked all Saturday. It's time to party all Saturday night.

27:54 Jason Leong: Yes, exactly.

27:55 Chris Titley: I'm gonna go to uni the next week and do the same thing and have a job during the week and go out Thursday night. And you know, so it's encouraging to see that there's a younger Yes. That are probably tapping in. This is probably ties into the Afterpay and maybe other types of businesses where people are like, okay, I don't want a credit card, I want a debt or whatever like that. So Jason, I'm curious as to your involvement in the Australian fintech ecosystem as well. You're based in New Zealand and obviously it's a global business, but your involvement with some FinTech Australia and some of the awards recently, the Finneys?

28:35 Jason Leong: Oh, well, we've been very lucky to be supported by FinTech Australia and to have been so welcomed into the community. It's one of our favorite things about working in Australia. Everyone knows everyone, everyone's very supportive, and introductions are quite happily made, and there's so many things that we have in common. And so we do work with partners locally as well. We were just over in Sydney last week, I think, for the CDR Summit. And so this celebrates the 5th year of the CDR. And we've got, you know, people from industry and government coming in to not just celebrate, but, you know, again, put quite a bit of heat on the stuff that hasn't yet been achieved. And so, you know, sometimes we do think that Australians are pretty hard on themselves. In terms of getting something right, particularly when we're here in New Zealand, we still have a very fledgling open banking environment. We look over at Australia and think, well, you guys have got really good, but we're so impressed by how much work has been put into it by the tech sector, by the finance sector and the government, and how, I guess, how committed Australians are to having this as a utility for Australians moving forward. Yeah.

29:58 Chris Titley: Excellent. Jason, I agree with you 100% and the connections and networks that you meet at some of these events go a long way and they can be potential customers. I'm sure you're, you know, that people hear about PocketSmith and they're like, oh, I might try that out. So that's a good thing to be a part of. We are sitting here in 2025 and it wouldn't be a 2025 podcast without talking about the effects of AI in any business and the trends that are happening in the financial world. Now, when it comes to AI and finance, For me, it hasn't really kind of impacted my life yet in terms of change of behavior. But things like ChatGPT in terms of transcription services and the speed of doing things, yes. Finance, maybe not. Can you talk about AI as a play with PocketSmith and/or the financial services sector, particularly here in Australia?

30:43 Jason Leong: Yeah, we've been very cautious about AI. As technologists, we're probably leaning further towards the cynical side than is healthy. However, We have been experimenting with it for a couple of years now, and we're just not convinced that it's accurate enough for us to unleash it onto our customers. We do have an AI experiments panel where we integrate lightly with ChatGPT for our users to be able to get insights on their finances with prompts. But really the most concerning thing is that You know, the LLMs that we've seen still create hallucinations that seem very convincing. And it doesn't matter if it gets it right 999 times, it just needs to imagine one wrong answer once, and that just breaks your trust in the system. So in terms of interpretation, it probably isn't there yet, but we know AI changes so rapidly. You know, every 3 months something new's happening. Where I think there is a real opportunity for AI to shine is to be almost like a trusted confidant when it comes to people who are nervous about talking about their money. So it really depends on your background, it depends on your upbringing and your education. And oftentimes people find it difficult to approach a friend or find a mentor or find a financial advisor to talk about their money or to ask questions because they might seem, you know, like they might feel that they haven't, they're not well enough educated to begin that conversation. ChatGPT lowers, or any LLM really, lowers the barriers tremendously to having people initiate that conversation. Not saying that, you know, AI should be your financial advisor, but at the very least, AI should open up the conversation and help people start thinking about finances because in many ways, It is in the, when you vocalize something, you're kind of already having that conversation with yourself. You're bringing it into a reality and that's the genesis of it all. So, you know, I think that's the first point. No doubt there will be amazing tools that will enable better financial clarity in the future, in the very, very near future. But right now we're still sort of holding steady. Interesting. We've all used apps with that little AI star and, you know, you click on it and you're like, damn, this doesn't actually do what I hoped it would do. You just put it up there and it gives me worse results than if I just use your plain text search. So—

33:24 Chris Titley: Yeah, no, it's interesting. Like the other day I had a podcast that I used a transcription service to put it into a PDF and then I put the prompt into ChatGPT and said, from this podcast, can you summarize the 5 main points for me for just to go back around the notes that I did and whatnot. And it came up with something, and I'm like— and I'm— and it was something like, uh, she started playing football at 15 or whatever. And I'm like, I swear I never remembered the word 15 and age group in this particular chat. And then I write, where's the reference to when she started playing football at 15? They're like, oh, I'm so sorry, that's not right, it wasn't in the PDF, that was our real research thing. And I'm like, well, there you go. Like, it There's some— I'm not saying, and obviously there's disclaimers around accuracy, etc., but it was just this caught me off guard moment where I'm like, no, no, no, it's not all right. And for the kids out there, they're doing their assignments going, uh, that's right, it does come back down to you. Like, I know my podcast, I don't— never, never remember that moment. Um, and, uh, but anyway, we could digress for hours. But before we get on to you a little bit, Jason, I'm curious to know if we do repeat this podcast in in 12 months' time, in 2026, in, in late July. Where would you like PocketSmith to be?

34:38 Jason Leong: I think right here doing what we're doing right now. There's, there's so much that we've got on our plates in terms of bringing a better personal finance story to Australians and to our customers abroad. We've got a whole bunch of features to make financial management more fun, more engaging, particularly Going back to our roots, which is in forecasting, the calendar that I talked about, that's still in PocketSmith. It's still one of our favorite features, but we've got some plans to make forecasting even better, even faster. So that's something we're very excited about. And a whole bunch of other things that are, you know, basically revolve around making PocketSmith more the center of your financial home. Mm-hmm. So again, nothing tremendously different, just the sort of business that we are, incrementally better every day.

35:33 Chris Titley: 17 years and counting, incrementally better every now, every day now.

35:38 Jason Leong: Mm-hmm.

35:38 Chris Titley: This is part of the FinTech Fun podcast series. I want to learn a little bit about the founder behind the business, not just about the business, but also what you do now when you're not talking about PFM and features and functions and categorization of things.

35:52 Jason Leong: Yeah.

35:52 Chris Titley: Do you switch off?

35:54 Jason Leong: Yeah, I try to. You know, it's a good question because oftentimes one reflects and realizes that they live a reasonably boring life outside of work. I'm very fortunate to be able to travel a lot nowadays. So that is a joy of mine. I think something significant that happened to me a couple of years ago is my dad passed away. And that, you know, he, towards the end, he had lung cancer. But he always said that he just had no regrets, you know, towards the end. He retired early, spent time with my mom, and was fortunate that it was towards the end of COVID we could all travel and actually spend time together. So that's actually caused me to reflect a little bit about the priorities I've got in my life. And, you know, people talk about those deathbed regrets and I wish I'd worked so hard, I wish I'd seen more of my friends. And that's something that I'm, I guess, trying to do a bit more of, which is to spend time with the people I care about. But beyond that, I mean, I didn't mean for that to get super heavy. I am in the process of restoring my house. So I live in a 1927 bungalow and I own a 1926 villa next door. Mm-hmm. And, you know, these are old houses and they hit 100 years in a couple of years.

37:18 Chris Titley: Yeah.

37:18 Jason Leong: Yeah, that's right. And, you know, it's been a lot of fun. I really do. I love these old homes and I think there's a lot of history in them that, you know, it's been a joy bringing them back to life. And oh yeah, for show and tell.

37:36 Chris Titley: Yeah.

37:37 Jason Leong: I was into sneaker collecting, you know, once upon a time.

37:40 Chris Titley: Was there a website in Australia that went off for that, wasn't it? Pump, pump, pump.

37:44 Jason Leong: Yeah.

37:44 Chris Titley: Well, it starts with a P, I've forgotten it now, so.

37:46 Jason Leong: Yeah, I mean, I think that hype sort of died down a little bit, but like this is one of—

37:52 Chris Titley: It was a COVID-style bump, wasn't it?

37:53 Jason Leong: It was, even prior to that, I think maybe in 2018 or 2017.

37:59 Chris Titley: Yeah.

37:59 Jason Leong: There was like, the sneaker market went crazy and the fun part of it, and so this is, you know, part of my bargain hunting, is to go find something at retail that skyrockets in value. And here's a pair of sneakers that, I think last was probably about $8,000 or $9,000 brand new. And it makes me feel like a kid again because I had a pair of these when I was like just a young boy playing basketball. But these are made by a designer called Virgil Abloh, who's since passed away. And his brand is Off-White. And he partnered with Nike to build a deconstructed version of the Jordan 1. So it's all got stitches and, you know, bits are hanging off the side and whatnot. And it's a little bit of fun. I don't really even wear these anymore, but I, you know, I still have a whole bunch of sneakers that they're just kicking around.

38:51 Chris Titley: Can I ask another personal question? Did you ever get into the early '90s trading cards of the NBA?

38:56 Jason Leong: No, I didn't, but I did get into comic books. They were from the early '90s as well.

39:02 Chris Titley: Yeah. Wow. So a shoe collector, part-time shoe collector, part full-time founder. You mentioned you did travel a lot. Surely there's a lot of founders out there that listen to this and travel a lot. Like there's, sometimes it feels a bit lonely. Sometimes it feels like the lounge food is a little bit dry. Sometimes you feel like you're not getting the best deal with the points. Are you all over it? Are you, do you know the hacks? What's some tips you can share?

39:28 Jason Leong: Oof.

39:28 Chris Titley: What about the airports you love?

39:32 Jason Leong: Oh, I love the, I love Dunedin Airport. That's one of the best hacks. We've got a gorgeous little airport. You know, getting out of the country is always 1 or 2 flights. So we've gotta get either to Christchurch, Wellington, or Auckland, and then out from there. But the beauty of checking in at a small airport, and this is not a hack that anyone can really do, is like, come move to Dunedin and use our airport because there are no queues. So if you're going on a long-haul flight, you check in, you just check your bag straight in and you're on your way. Whereas if you're at any of the bigger airports, the queues are horrendous. I love staying at Airbnbs when I travel. I know that it's, you know, not that favored in certain cities. There's a big revolt currently in Spain, I think, against people basically buying up homes and pushing up property prices. And I think that's a terrible thing. But in Japan in particular, where they put in a law called the Minpaku Law in 2017, I think, where holiday homes or rentals can only be rented out for like 6 months of the year and they have to be licensed. So they've managed to keep a control over, I guess, conglomerates buying houses to lease for short terms. But I love staying in quiet little neighborhoods and just soaking in the atmosphere, eating the local foods. And that gives me a bit of a, you know, I guess just some space to be someone else in a different place.

41:02 Chris Titley: That's brilliant. And do you sort of, do you bid for the upgrades? Do you kind of get upgraded? Do you kind of like nudge, nudge, wink, wink to people when you check in like, oh, you just want an upgrade, you know?

41:10 Jason Leong: So the one tip with travel would be, and any seasoned traveler will know this, is just stick with one alliance and—

41:20 Chris Titley: Don't chop and change your frequent flyer program 'cause you'll go nowhere. Is that right?

41:23 Jason Leong: Exactly, that's right. And so, you know, we're stuck in with Air New Zealand and Star Alliance for better or for worse. So Air New Zealand has really suffered a lot since COVID because they got rid of a whole bunch of their planes. Things are very expensive and the connections are very poor, but the service is very good. And Star Alliance Gold, I think Star Alliance is probably one of the biggest networks out there.

41:44 Chris Titley: Mm-hmm.

41:44 Jason Leong: And they're, you know, so for me traveling into the States, for example, and hopping onto United, I still get to use their lounges. Similarly with Singapore Airlines. So they're really, really great airlines on the program. Lounge access is one of them, but you know, you still get priority baggage and all of these nice things. And particularly in the States, if you're Star Alliance Gold, United has a number of lanes that get you through security faster as well. So if you're not an American resident, for example, you don't have TSA PreCheck or any one of those things, you can still get through a lot quicker. Yeah. So that's my plug for Star Alliance.

42:28 Chris Titley: So we've covered travel tips, we've covered basketball shoe tips, well, sneaker tips, and we've also covered financial.

42:36 Jason Leong: We have.

42:37 Chris Titley: Financial management, right? We're not here to give financial tips. We'll get in trouble if we do that. But we're here to give a little plug for PocketSmith. Jason, it's been a delight having a chat to you today about the history. Of PocketSmith, the progress that the company has achieved thus far, and also the future plans and the ins and outs of AI. And also let's end the talking about the personal household CFO, which is, I think is very, very important that people take that role. And as you mentioned, the sort of unsung heroes of one's household. I wish you all the best. Now, before we go, how do we go about getting PocketSmith? How do we start? Where do we go?

43:14 Jason Leong: It's very easy. Just go to our website, pocketsmith.com, and you can sign up for a free account there and you can start tinkering straight away. We've also got a great blog where we write about money and you can see all the stuff that we're interested in. We've got pieces about neurodiversity, freelancing, identity theft, relationships, all things human, because that's the sort of company that we are, just related to money. Pocketsmith will do a lot for you at the start, but we also have a great learn center to help you improve your financial skills and really give it a run for your money. We challenge you to challenge it. And we've got a wonderful support team who are ready to help you out if you need.

43:53 Chris Titley: Jason, Leon, thank you so much for sharing your story about PocketSmith and looking forward to following your progress.

43:59 Jason Leong: Thanks, Chris.