The Fintech OG Series: Oban MacTavish and Allen Miller

Powered by Spade.

Even the most polished fintech apps break on one stubborn problem: messy transaction data. The same merchant can show up differently across issuers like Amex and Chase, driving broken rewards, poor insights, fraud risk, and support noise.

We sit down with Oban MacTavish, CEO and Co-founder of Spade, and Alan Miller, Partner at Oak HC/FT, to unpack how raw transaction data gets transformed into clean, structured merchant records in real time.

From Spade’s scrappy, hand-labeled beginnings to its bet on treating enrichment as a search problem, we explore what it takes to build durable fintech infrastructure. We then step back to look at fintech’s shift toward sustainable growth, the rising importance of clean data in the AI wave, and where stablecoins and new payment rails are gaining traction.

Subscribe for more conversations with operators building the future of financial services.

This episode is sponsored by Granola. Try it free for 3 months at granola.ai/thisweekinfintech using code THISWEEKINFINTECH.

Connect with the Hosts & Guest

Julie VerHage-Greenberg: https://www.linkedin.com/in/julie-verhage-greenberg-1748801b

Lauren Crossett: https://www.linkedin.com/in/lauren-crossett-b3752126

Oban MacTavish: https://www.linkedin.com/in/oban/

Allen Miller: https://www.linkedin.com/in/allen-miller-6670b133/

About The Fintech OGs

Former Bloomberg Fintech reporter Julie VerHage-Greenberg leads panels of the people who’ve taken Fintech from a hashtag to an industry through discussions on where we see the industry moving, what it takes to stay on top of the enormous changes that are still gripping the financial services industry,  and what they have learned as the best leaders in the field.  

Listen for the best up-to-date know-how from leaders in banking, payments, venture capital, fintech entrepreneurs, and all of those that have recreated financial services, and are still at it.

Transcript

Opening

Julie VerHage-Greenberg 1:26

Everyone, even in 2026, when fintechs can spin up cards and minutes and move money across borders in real time, it's still hard to decipher transactions. That's why financial institutions turn to spade. Spade is the data and AI platform that turns messy transaction strings into structured, verified records in real time. To learn more, head to spade.com. That's S-Pa-D-E.com. Hey everyone, Julie Verhage Greenberg here, back with This Week in FinTech, which is now also a plaid company. Nothing is changing that I know of at this point. Maybe just more podcasts and stuff in the future, but all good things. Um Lauren actually texted me that day. She's like, congrats on being acquired by plaid, since one of Lauren's former companies was also acquired by plaid. At some point, everyone just keeps ends up working for plaid, right? Um, if you're in fintech long enough. But I am back with my co-host Lauren for another episode of our fintech OGs. And today we have one of her bosses, Oban MacTavish, who is a co-founder of Spade, and we have Alan Miller, who is from Oak HC/FT. Um, they have invested in a bunch of different fintech companies. Some of them that you might know would be Blend, Bridge, which was acquired by Stripe. Blend obviously went public, FastPay, and Paxos. And one of their most recent investments is Spade. So I have to start. Did you guys, when did you guys meet? Was it for this investment, or have you guys known each other for a while since you've both been in fintech for a while at this point?

Allen Miller 2:53

I'd be really curious to see what you remember, uh, Oban. Um, but I was sort of going back through my emails. I think what happened is so you know, we invest in a lot of fintech infrastructure companies. That's kind of like a little bit of our bread and butter B2B applications and infrastructure. And I think I had seen an announcement, and I think it was around your seed round, and I think I actually cold emailed you just to say hi and catch up and all that. That was, I think, three years ago, 23. Um, and then I think we had sort of like interactions on and off. And then the next kind of clear memory for me was money 2020, I guess uh this past year when we sort of sat down and I think test came as well. And that was like a big aha moment for me at least. And that's I think what started to lead to some more deeper discussions about this round. Um, but does that does that kind of generally sound about right?

Oban MacTavish 3:44

Yeah, I think that's that's how I remember it too. Um, I definitely I know we spoke. I remember I went to the Oak offices. This is back when I still lived in Vancouver. I was visiting New York to do the whole, you know, do the rounds as many founders do if they don't live in the States. Um, and I met you at the Oak offices because it was, it was after we had raised our seed round. I think maybe I want to say, yeah, 23. So postseed round before we had raised our A, as we were sort of figuring things out. And then yeah, I agree. The the next big thing. And then I we definitely I feel like there might have been something in the middle there, like early 20, early 25, pre-money 2020 as things we were just sort of talking about what our plan was, and then 25 is like, hey, we we did the thing we said we were gonna do, which and even better. So it's always nice you can show up and have that conversation. But yeah, so I think it's been a long time actually. It's been three years, I guess.

Julie VerHage-Greenberg 4:33

It's wild that 2023 was already three years ago. Uh I'm like, wait, that that doesn't feel like that. I'm just like, whoa. Um, well, let's take another step back then. And how did each of you first start out in fintech then? Since obviously, you know, Alan, you've only been at Oaks since I think it was like 2019. Um, and then Oban, you have been at previous fintechs before co-founding Spade in this space too. So Alan, maybe we we start with you.

Allen Miller 5:02

Yeah, sure. So my my journey to fintech, I gotta go all the way back to I think it was like 2013. So the I had been living in New York City and um I was going to business school at Columbia. And uh like I think one of the very first fintech companies, one of the first notable fintech companies was a company called Betterment, um, the Rome Advisor. And I had um downloaded the app. I think I was one of the first couple hundred users of the app and had started using it and playing around with it and kind of got just really interested from like a consumer perspective in fintech from that regard. Then when I went to business school, um, you know, the um the founder of Betterman, John Stein, was actually a CBS alum. And I was like, well, I would love to like, you know, do something while I'm in school, like on the side, nights and weekends, kind of like a side hustle type of thing. And I cold emailed John uh just to be like, hey, I'd love to like, you know, I'd love to just do something. You know, it's part of this program called Insight, which kind of helps um, you know, play students at startups and do project work and and all that stuff. So I actually ended spending my second year in business school working with um his co-founder, Eli Bruverman, and a few others um on a few different things uh inside of inside of Bettermant. And so that was like my first sort of you know fray into it, and then from there it kind of kind of uh went into being a consultant and then also being an investor. Um but yeah, that was my my my journey.

Julie VerHage-Greenberg 6:29

Very cool. Check out season one of fintech OGs for an episode with uh it was John Stein and Alexa von Tobel.

Oban MacTavish 6:35

So really off to do.

Julie VerHage-Greenberg 6:37

Yeah. Oban, what about you?

Oban MacTavish 6:39

Those are real fintech OGs. Um I right out of college, I co-founded a company called Hubly, and we were selling uh efficiency tech, like think like practice management software, very similar to what you'd see in like a doctor's office or a dentist's office um to wealth managers. And then we did we started that, I guess that was 2018, so not a decade yet. I guess it's eight years ago. Uh did that. Very close, very close. Close. I know. I know. Makes me feel old.

Julie VerHage-Greenberg 7:11

Um it's gonna be really weird when we look back and like COVID was a decade ago, and we're not that far away from that either.

Oban MacTavish 7:19

Yeah. Um, no, so we we were selling that, and then I think that's technically considered fintech. And then we did uh Barclays Tech Stars in New York in 2019. Um, and that was like that was my first time living in New York. Uh we lived in like I think my bedroom is literally seven feet by five feet. So it was like a tiny rectangle in Chinatown. It was such a, it was, it was very cool. That was my first really that was the first time I ever touched fintech and was sort of the thing that led to Spade, which is very funny because I met a bunch of other fintech founders at Techstars. It was also sponsored by Barclays, so there's a lot of like Barclays connectivity. That was our first sort of touch point into like the actual fintech universe, especially because as a Canadian, like there isn't Canada doesn't have a big universe of fintech companies. There's a couple now, and like I think it's becoming a bigger thing. But back then, I think there was literally Coho, and that was it. Like there wasn't really uh fintech coming out of uh Canada. So it was kind of alien coming to the States and hearing about all these like you know, like Cash App, Venmo, these things that sound so far away when you live there, because it doesn't exist in Canada. So that was the first time I really started engaging with fintech.

Julie VerHage-Greenberg 8:22

So did you move to New York and then move back to Vancouver for a little bit before? Okay, walk me through that a little bit too.

Spade’s Scrappy Founding Story

Oban MacTavish 8:28

So I moved to we moved to New York for Tech Stars and then moved back to Vancouver and then kept sort of trying to build the company. I mean, it was a very different time. And then COVID happened, lit like COVID really kicked off. So we literally did it like until December 2019, went back to Vancouver, and then three months later, March 2020, I guess, was when things really happened. We were trying to raise a seed round at the time. So that was a whole experience. I wasn't I wasn't fundraising. Uh, that was one of my other co-founders. I was really trying to like, at that point, like trying to keep the lights on and figure out like what did we need to build to you know actually sell the financial advisors. Um, but it was very bizarre. It was very like, you know, you go New York, especially New York FinTech, I think, in like that time was also like incredibly in person. Like it was a very cool time. Everyone there was like a lot of energy around it. And then obviously, COVID, I was back in Vancouver, my first company is like, you know, with zero dollars left, like literally zero. Um, decided to step away from that, figure out what I wanted to do, and then sort of like stumbled my way towards spade over the course of the next, I guess, two years from that point. So it was a very, very interesting experience. But it was uh, yeah, it was I feel like once you touch fintech, you never really want to leave. At least I didn't. Um, you sort of get you see this whole world open up in front of you, and you're like, wait, this is like this weird universe with this cast of characters who always sort of pop up and these like it feels very like, oh, this is like a world within a world. You know, tech is so broad, but fintech is this nice little niche that is also happens to be one of the biggest industries in the entire planet. So yeah, that was uh quite the journey I went through to eventually end up building a fintech infrastructure company, having never worked in payments before.

Julie VerHage-Greenberg 10:03

That's that's a wild like five years right there. Not like three to five years. Yeah.

Lauren Crossett 10:09

I feel like you can't leave us hanging. Now you gotta explain like the the origin story of spade.

What Makes Enrichment Truly Difficult

Oban MacTavish 10:15

Yeah. Um that was spade was really born out of a weird in-between time when you know, I just left my first company, was really trying to like move away from tech. I was like, I don't want to do this anymore. Um, too hard. Um, no, but I think you when you're building a company, at least for me, I think you figure out pretty quickly like, is this, do I want to do this the rest of my life? Like you're raising money from venture capitalists, you know, there's all this momentum, things going well, and then things are tough. And you know, you eventually, I think for me, you step back and you're like, I don't know if this is my life's work. So that was my first company. I was like, I don't know, two years in, I don't know if I can be like, hey, we're gonna go out and raise even more money and keep building and like do this for the rest of my life. Because I feel like that's kind of the commitment you're making. Um, so I was like, no, I'm gonna step away, I'm gonna go do the whole like finance thing, I'm gonna apply for jobs on Wall Street, do that, and then but thankfully, um, I was literally trying to pay the bills. Like I was going to all these FinTech founders who I've met through Barclays Tech Sargent, like, hey, like, do you can do you need like pitch decks? Do you need like business development stuff? Do you need like sales materials? Do you need to like run around and do market sizing? I don't know, just like literally anything so that I could literally pay rent. And they were all um, you know, I found a bunch of odd jobs, and that was cool. And they were all just complaining about their data, literally just like 24-7. Because they at this point, this was like neobank heyday. Everybody was a neobank, everyone was building their special rewards program, everyone wanted to build the like Cash App experience. And um, we were like, hey, what if we could just build an API that would just like give them logos, nothing else? These little logos, how hard would that be? And that was really where Spaped was born was like this idea that at that moment was like there was so much fintech demand, and everyone was trying to do really interesting things, and they needed better data to do it. And it started with user experience and it obviously grew very, very quickly outside of that. And it was one of those moments where I feel like I saw what I think is still as the biggest market or one of the biggest markets in financial technology is like data is built, so much of what we do is built on top of data, and it's all bad data. And this just feels like a problem that should be solved. And I was absolutely shocked it wasn't solved at that point. I was like, okay, you know, you do that for a couple months, you have suddenly signed all these people. You're like, oh, maybe there's like a huge opportunity here. And that that was really the number one thing for me when I was like, if I was ever gonna do this again, I want to be doing something in such a big market that it's like undeniably large. And I think that's what we found here at Spain.

Lauren Crossett 12:24

Yeah, that's great. And Alan, I guess, you know, Oban's talking about what he found really shocking. Has there been something in FinTech that you found really shocking? That like, why is why hasn't this been solved?

Allen Miller 12:36

Well, you know, it's it's funny you mentioned that because uh going back to that first meeting right three years ago, um I came away from that meeting being kind of like, well, Oban's great. This is a really credible founder. We'd love to be invisible with a guy like him. But this is like a problem that's like a hard, uh like really hard, and so much so that there have been other you know players that have tried to do things similar kind of on the edges of this and haven't really worked out. So, you know, I was a little bit skeptical that this would actually kind of come to life and uh and and all that, but um, thankfully, OBEN we were able to stay in touch and um he was obviously able to deliver in a very big way. Um but look, uh you know, at Oak, we like things that are hard, right? I mean if you look at um if you look at most of our portfolio, it tends to be infrastructure, it tends to be um you know B2B applications, it tends to be in highly regulated areas. A lot of our portfolio deals with areas like fraud, you know, one of the um um open uh space that you know biggest uh use cases around fraud and authorization. And so we tend to have to sort of um gravitate a little bit to things that are very hard. Technically, it's hard you know from a compliance and governance perspective, um because that's where you can build really interesting. If you can crack it, right? And if you can solve these hard problems, that leads to a moat, and then eventually you can scale that and also have to really interesting customers. So we were drawn to the fact that it was hard that it was hard to cost a bunch of dimensions, right? Like first you have to build the coverage, right? There's a whole bunch of just merching the coverage you have to build. You've got to be accurate, right? You've got to have the depth of the coverage and then the actual attributes that um spade actually returned to the screen to talk about in the speed, right? Um having the latency to be able to sort of respond in real time. And the fact that you know Spain actually built this capability across all four of these kind of attributes was was really compelling. And um, and then of course last year they had a lot of uh dimensional things in part to e-board um on the go to market side. And um picked up some really interesting logos, you know, Stripe and CapCap and FIS and a bunch of other really interesting customers. So that was really exciting, and and I think we're now really excited to see where this all goes um from here.

Julie VerHage-Greenberg 14:50

Oban when so you mentioned how you'd never been in payments before. This was kind of like your first foray into it. Um and Alan mentioned that this is a hard problem to solve, which is part of the reason that no one had done it before you. Other than, you know, what the first thing that comes to mind and why this is hard is that transaction data is messy, right? Like if I look at my Amex statement versus my Chase statement, the same company that I'm buying something from could look different. Uber, it might be a ride, it might be Uber Eats. Like, you know, that gets qualified as different things, et cetera, if I'm doing like a PFM. What else is really hard about it? And why do you think, like, what have been some of the keys to being able to overcome those challenges and actually build this, scale this and make it work?

Hand Labeling, Matching, And Scaling

Oban MacTavish 15:35

I think it goes back to a little bit of what Alan said is that I think a lot of people approach this problem as like a an ML problem. They're like, give me all the transaction data in the world and I'm gonna train a model and I'm gonna fix all this data. And like, if that actually worked, we wouldn't exist because Visa and MasterChire would have infinitely more transaction data than anybody. Um and if that had worked, Chase wouldn't need a vendor and Cash App wouldn't need a vendor. And a startup couldn't do it because you're always gonna have less data than the people you're trying to sell to because they're that they're that far ahead of you. And we really did it the other side, and part of that the other way, which is the part of it was that we had no venture capital and we were just a couple people. So we were hand labeling data. And if you don't have any transaction data, it's sort of like the requirement is that you have to figure out another way to do this. So we figured, well, what if you turned this into something that looked a lot more like a search problem where like Google went out and indexed all the, you know, the entirety of the internet, and then you put something in and they they surface you the most, like the thing they think you're looking for, really, and they score a bunch of these things and they give you the most likely answer. And that's what we did with transaction enrichment. And I think the hard part about that is that it is kind of counterintuitive to how other people had done the problem. But ironically, because I had no absolutely no experience in payments, did not come from like a big company that had been trying to do this. I approached it in the only way that made sense, which is like, well, let's just hand label a bunch of data and then get really good at figuring out if this is that, and then you can sell it to people. And we found really quickly it was it was amazing. But obviously, once you do it that way, it becomes a very different kind of business. You know, it's about how can I source, clean, and verify millions and millions of business records, constantly update them, and then make sure you're matching things correctly, which is a very different problem, um, but it's really hard. Um, it's one of the reasons we've stayed really focused historically on the US, and then recently we expanded to Canada, um, was because it is actually a very challenging problem. And I think obviously that was a pretty unique insight and pat myself on the back there. But once we started doing it, I think you realize that it is a much harder way to solve the problem. And that's why people hadn't tried to do it historically. And that's why it's so why someone like an Amex is so successful at it. Because you know, Amex.

Julie VerHage-Greenberg 17:37

Remember that moment where you had that realization? Like literally like walk me. Like, when did it just like go off in your brain?

Oban MacTavish 17:44

Well, I I wish it was like, I wish I was like, you know, no Shadamas and was like, oh yeah, this is this is the way. I think genuinely what happened was that we had been, I was talking to a FinTech founder friend of mine. He was like, Oh, we don't have any logos in our transactions, we want to build this user experience. I was like, Oh, if I saw if I gave you an API that did that, like would you pay us? And he was like, Yes. The funny part is we weren't an incorporated business, so we couldn't accept any payment for a really long time. So he didn't pay me any money. But we were able to do it. And what it came down to is I was sitting there with one of my co-founders, Cooper, being like, Okay, so how are we gonna do this? I'm like, well, what if we just like, okay, you know, AI doesn't exist at this point. So, like, you know, it's really long time ago, and we're like, okay, let's just Google and like find all the lists of every single, like the most transacted app businesses across the US. Okay, we'll do it. Because this is like a neobank. And we did it, we found all the lists, and then you know, we spun up some infrastructure. We built a little uh a user experience where we can input all this important information. We just started, you know, you start labeling and making your own data. You know, you human label, human acquire, download. I got really good at Photoshop. Actually, no, it wasn't Photoshop because we couldn't afford Photoshop. We got this, there's a website called Photo P, which I'm gonna plug here. It's like free Photoshop in a website where you could like take it, take things and edit photos for like you know, cropping all the logos so they would fit nicely, typing it all up, getting the websites, doing all these things. And then my you know, one of my co-founders, Cooper, who's I guess far smarter than I was, he was the one doing the much more challenging thing of like, okay, how do we match these things? And we started literally hand being okay, how many ways could this appear? Let's write all this regex. And we're really going through doing this by hand. Um, and then we were, they did a comparison between us and a venture-backed competitor of ours at that point that had raised millions of dollars, and we absolutely crushed them. And it was a very funny moment because we didn't even know this was happening. And I get like a slack from my friend being like, hey, we compared you against an unnamed competitor. Um and you guys were way better. Like, how did you do that?

Julie VerHage-Greenberg 19:33

And I was like, Oh, it's just you know Is that competitor still around or no?

Oban MacTavish 19:37

Um in a form, I guess. I don't know if they would I we don't see them anymore, but I think they technically exist.

Julie VerHage-Greenberg 19:45

Okay. They might have pivoted a little bit since companies were better at doing what they were doing. Exactly. Exactly. Very cool. Was there ever a moment like once you had come across that realization where you thought maybe that realization wasn't right or that it would be too hard to do all those things that need to come true to make that work?

Oban MacTavish 20:04

Yeah, well, when you hit like merchant 1500 and you realize there's like millions left to go, I think you're you're sort of looking at a daunting task and like, I don't know if this is gonna work. And then we tried to like, we were like, okay, now people want location data. Like, how do you go about doing this? And then you start scraping using um what's it called? Uh store locators or some fun stuff you can do with that. But then now you get in the data validation problem. We still had no money through this whole thing. So you're sort of being like, okay, this is like the least scalable thing on the planet. How many people do we have to hire to label this stuff? And then eventually you raise money and then you go and acquire the data from elsewhere, which is a far more intelligent decision. But there was definitely times along the way where you're adding customers and you're realizing that like a business customer, so those small business cards looks very different from a consumer card company, which looks very different from a disk. And like, you know, suddenly the merchants they care about look very different. And there's this moment we were sitting around being like, I don't know if this is possible. Once we had acquired data, and then you can start scaling these things very differently once you have capital, but there was a moment when you're adding on new customers and your performance goes from like, oh, we did it, we got someone to 80% over here, and this new person comes in and it's 40%, and you're like, oh my God, like that's not a business. That's like a I don't even know what that is. That's like a you know, a trial that we have to continue doing and labeling this data, but you know, you figure it out.

Julie VerHage-Greenberg 21:20

You also make a good point, like none of you guys had had some big exit before starting this company. So it's more like, you know, you guys were kind of like Max Levchin starting PayPal versus Max Levchin starting a firm, right? Like when he started a firm, he didn't have to worry about paying his rent and all that. He was fine. Um whereas you guys are more like PayPal, I assume he didn't have a ton of money at that point when he was starting that company.

Surviving Fintech Winter As An Investor

Oban MacTavish 21:41

No, and you're not an incorporated business and you're like, you know, you're trying your best, but you kind of need some money to make these things really work. You're like hoping the infrastructure doesn't go down.

Allen Miller 21:50

Because it's a story of like a like necessity plus serendipity coming together, and obviously the in the um the insight that you had to like, hey, there's a there's something here, right, to go pursue. Um so yeah, amazing story.

Lauren Crossett 22:05

Yeah, and just because you know, I'm self-preservation here, uh, our match rate is certainly well beyond 80% now. Um so this is a little caveat that we've come a long way.

Oban MacTavish 22:17

Um we are talking about 2022 at this point, or 2021 at this point, so yeah.

Lauren Crossett 22:22

Yeah. And probably even on the like small part of the journey that you just went through, um, there were a lot of highs and lows, but maybe zooming out more. And Alan, why don't we start with you? If you could talk us through your career highs and your career lows, we'd love to really understand what your journey in fintech has looked like.

Allen Miller 22:41

Yeah. Um, let's start with the lows so we can end with the highs. Um, I it's hard to not so I've been at Oak since 2019. And in a lot of ways, that was kind of like a weird, weird time to like join. And I started inventor in 2017. Um, but kind of like immediately, you know, we had this kind of like once in a general generational thing happen, right? Which is COVID. Um, which for a brief moment was it was unclear what was gonna happen. We had this massive acceleration, and then we ended up this like fintech winter, right? Like 22, 23. I mean, these were really, really hard, you know, years. Um, and you know, being an investor and and a The investor in a number of companies trying to survive this. You know, that was really hard. I mean, there were a lot of very difficult conversations with companies. And again, we um as fintech investors, you are exposed to lots of different business models, right? You've got software as a service, a little bit more recurring, you've got payments, a little bit less recurring, you've got lending businesses, you got consumer, you got application, you have infrastructure. So we had companies all over the map. And in general, I would say those were, you know, we certainly had companies that have come out of that and thrived and better for it. Um, but along the way, even the companies that did come out much stronger did have to make a lot of tough decisions. So there were a lot of meetings um, you know, in that two-year period that that were just painful, and just talking about doing the hard things around, hey, we've got to like deprioritize the roadmap and we've got to probably let go of some of our value, valuable employees, and we've got to figure out how we're gonna survive.

Julie VerHage-Greenberg 24:17

So that was um and Alan, this is your first time being a venture investor too, right?

Allen Miller 24:22

Uh I had done a small thing at a firm called Matrix Partners before joining out uh for two years. Um yeah, coming to Oak.

Julie VerHage-Greenberg 24:30

But like that's just those are those are such hard conversations to have, not just because like in general they're hard, but too, like COVID was something no one could see coming, right? It's not like you know, there was anything you could have done to prevent the business going the way it did in most of those cases, I assume.

Allen Miller 24:46

Yeah, I mean it there there is a um of course you can always say there are certain businesses that are like e-commerce, for example, or the more music world, right? That there's a certain level of cyclicality. Um, but this was sort of just like an unprecedented thing that had happened to the world, right? And then you compound that with um, you know, then the SVB thing happened and a few other things kind of so it's just sort of like one thing after another. Um and we were all sort of navigating this for the first time. I think a lot of founders, even if you were a repeat founder, you were navigating this you know for the first time. And I think FinTech is a little nuanced in the sense that um like in SaaS, for example, you have recurring revenue, everything kind of is is relatively, I wouldn't say totally predictable, but it's more predictable than like payments. If your payment volume is up one month and chunking along, and then all of a sudden, because of an external factor, it kind of goes to zero. You don't have that sort of recurring kind of um uh sort of sticky revenue case where you have to kind of figure out new ways to grow and just basically survive. So we did have companies in that situation. So that was, you know, that was that was very, very, you know, sort of challenging, I would say, to to kind of um to navigate.

Julie VerHage-Greenberg 25:54

Um it's like imagine if Sofi, if SoFi had been founded in 2019 versus 2011 and they were still just doing student loans, like SoFi probably wouldn't exist anymore at that point, given the more torment, like all debt was there was no interest rates, student loan collections were paused. Like, what would SoFi do? There would be no point to go refinance your loan.

Timing, AI, And The Next Wave

Allen Miller 26:14

Yeah, Julia, I think this is like a really like broader important point of like the time when you start. There's a lot of skill involved. There's a lot of um like founders who are resilient and and can see around corners, but like literally the time you start the business in the world of the business. You start a business, I think of like right now, right? Like if you start a business in 23, 24, 25, it's kind of a different era than if you started, let's say, 2019, right? Uh or 2020. Um I mean, think of the last big wave of like innovation that we have, which is really cloud SaaS applications, like starting a business in that area around 2010, 2011, and being able to basically kind of enjoy this like 10-year run uh would be a lot different than starting a SaaS business, a SaaS application, let's say, uh in 2020. So there's a you know, there's a timing component here that um is just is is what it is, right? Um so that was you know that 22, 23 era a lot of just navigating things that were not necessarily foreseeable, that were just new, and a lot of like personal personnel decisions that were impersonal in nature, right? Um so that was that was kind of um kind of a very uh sort of hard thing to do, I think. You know, I guess on the flip side that means the positive is kind of seeing um, you know, I'm on the board of about eight companies now and seeing a lot of these companies emerge from that time period. Um some of them had to do the very out things like lean uh to then grow again and scale again. I've seen a number of these companies kind of weather that storm get you know capitalized further after, you know, after two or three or four years of not having enough capital. And then seeing these businesses kind of like take on a new shape, a new form, and have like a almost a second life and and rebound in some cases to like even better than they were, much better than they were before. That's been like a really uh really like um great thing to see. And the other thing is like I um have invested outside of the area quite uh like Latin America or Canada and places that you wouldn't expect some of those companies to have really players in their markets. Um that's been a real joy um you know to see over the year.

Julie VerHage-Greenberg 28:35

Oh, but I want to add on to your answer for the low. Um and that do you think you guys started Spain at the correct time, just since we were talking about timing that stuff too? Do you like if you if you could, would you start it sooner or later, just given that AI obviously would have helped you do a lot of those list making, etc. Um then, but someone else could have came up with the idea before you did.

Oban MacTavish 28:59

Yeah, I mean, I think it's hard, we definitely weren't the first. Like we had competitors. I think it was a unnamed competitors that were exactly the graveyard, as we like to call them. Um uh no, uh that's a great question. I think in so much that like it's kind of it's turned out really well, which is great. I do think it was a really challenging time to start a company, though. You know, we did raise at a probably the peak. Like if you look at like fintech valuation, we raised our seed like March 22 uh and had the had the great fortune of partnering with Andrews and Horwitz very early in our life cycle. But then you hit fintech winter and a massive, massive pullback. And we had to navigate and like you know, yeah, talking about lows, like we had to navigate a huge chunk of our earliest customers, like evaporate instantly. Like we're really lucky because we made some decisions. Like, if you think about the life cycle of spade, we raised our pre-seed in November of 21 from Gradient Ventures. We had Y Combinator, immediately raised our seed, had a bunch of had a bunch of money in the bank and had literally zero employees. So we immediately had to sort of go from being like this small thing that was growing very quickly to like a company. And then we literally built, but we we just had to build. And we went around, we built, and we spent a lot of time like actually building technology and went really quiet. And then 2023 is when we sort of like reintroduced ourselves in the market and started selling. And then everyone went bankrupt. So that was really, really hard. Like there was definitely a moment where not only did we have to change our product, we initially were like, we're gonna do what everyone else was doing in the market, which is we're gonna do all types of data, we're gonna do plaid data. I mean, plaid was having a moment, obviously. Everyone was a PFM, everyone was like, aggregate data, aggregate data. So we were doing all kinds of data, and and we had to be like, well, we're not gonna do that because there's no money there. And all the startups who do it are going bankrupt. And we had to make that decision like in the span of a week because we also knew that if we wanted to start selling to like mid-market fintechs who were gonna survive, who had money, you had to start those conversations. You know, they weren't gonna convert. And if you look at our growth in 2023, we didn't grow. Like there was a period of time where like our revenue was essentially flat. And that was just because we were making up for people either reducing their volume, going bankrupt, spending retirement, like it was a really, really challenging time. Um, and I think you know, you learn a lot in those moments about like building a business that actually makes money and realizing that like growth is like, you know, the slope of your curve is super, super important, but it's also about building like an actual sustainable business that people want to pay you for a thing. And if someone, you know, it's why some of these AI companies are so fascinating, because it does feel a little bit like they're like, you know, this all seems the music is going, so everyone's spending all this money, but the moment it disappears, it's all gonna collapse. And I think in fintech we had that moment and it was a super dark time. So I think you learn a lot and it builds a certain level of resilience to go through those types of things. But there's probably better eras to start the company or easy, easier times.

Lauren Crossett 31:53

If if it had been the AI era, it would have been easier to just not do it the hard way, which which I feel like is kind of our our, I don't know, our magic element is that like, you know, it wasn't an AI problem. It was the search problem that you talk about and like seeding uh enrichment with an actual verified database. Um, because you know, I was kind of behind the scenes for this journey, um, started advising you what in in 23? 29.

Oban MacTavish 32:25

No, it was it was 22, yeah.

Lauren Crossett 32:27

Yeah. Um and so like from my perspective, um, I feel like that actually brought such a unique element to spade. Like, you know, even in my excitement, joining full-time is like this idea that like there is an actual value asset in our data asset, um, which I think is really unique in fintech. So um, but tell us about your hack.

Stablecoins And Payment Rail Futures

Oban MacTavish 32:52

I think, I mean, I've never been more excited than right now, which is maybe like the best fun answer. But I do think um it felt like we were living in this future state. You were, you know, I think I like to say like either people would instantly buy our product or they would just be like kind of confounded by the idea of like why they would want better data for quite a long time. Like, I think we look really smart right now, and that's great. We're we're so smart. We were living in like this future state, but I do think people, very similar to many infrastructure companies, like you're trying to convince people that there will come a time in the future when they're gonna desperately need your product. Like, I think you know, as I'm sort of like a like a bit of a crypto hater or whatever, but I think staple coin people see it in the same way, right? Like they're they're seeing this future state and trying to bring customers along to that. And you'll find these like super innovative companies, and like we've been so lucky to partner with people, like a Mercury a long time ago, when like now they're a juggernaut and now they're crushing it. But there were moments where like there was no guarantee. And I think you find these people who are doing something in the future that requires technology that doesn't exist everywhere. I mean, you look at Stripe, same thing. They were working with these tiny YC companies who were like, we're selling something online, and not everyone was doing that. And I think we were lucky enough to do that. Um, but now we're living in an era where like there it is a requirement. Like whether or not we want it to, this weird Pandora's box of AI is like here to stay, and industries are changing, and financial services is as sort of slow moving and as as large of the behemoth it is, it will get there. And I think there's an understanding among many of our banking customers who are like not just the JP Morgan chasers of the world. We're talking about the top 20, we're talking about the top 50, top 200 banks who are looking at this thing, okay, great, in five years, we're still gonna be here. And for that, we need better data. And I think that's like there's never been a more fun time in spade's history because there's obviously like there's the ego being like, great, we did it. Yeah, we were right. But there's also that sense of like, okay, it's pretty amazing to see people who normally I would have expected to be like sort of dismissive of us being like the people most excited about it. I think it's a very special feeling when you get to walk into rooms with people who you never thought you could sell to, and they're actually just like desperately interested in buying your software. And I think that's a very special moment. And we feel really lucky that like we get to ride that way, but also we get to like come along on that journey with so many people who are innovating for you know millions and millions of customers. So yeah, it's a it's a great time. Right now is probably my favorite time.

Julie VerHage-Greenberg 35:12

You mentioned again that you're a crypto hater and I forgot that. Um and it just reminded me, you know, we have all this data on like the blockchain, you're gonna have stable coin data and stuff now. How does spade play into that? Like, is that I this is again from someone that's just like looking at the outside, I'm super not technical and don't understand all the nitty-gritty of it. I understand like transaction data a little bit, but I haven't gotten I've I haven't been super into crypto or anything. Um, so I would say I'm not enough either way to say if I'm a hater or a lover at this point. Um, but how would Spade play any sort of role in like blockchain or stablecoin data?

Lauren Crossett 35:48

This is so perfect because I literally seeded a conversation in the product channel with one of our eager engineers yesterday. And I don't know if it's come back to me yet.

Oban MacTavish 35:56

So I don't know enough about like my uh quizzical, or I guess my maybe skepticism, I guess, of like stable coins is not necessarily that it is bad technology. It's that I don't know where that market's gonna go. And I can't really pretend to be a massive expert in it. I think it is interesting. I think the thing we think about, and like pivoting the question slightly, is like, I don't think we play a huge role in some of these systems uh because we're not experts in the space. It doesn't mean we couldn't. But I think when you're building a company and like now that we're at the stage we are, like our customers rely on us. And like as much as I love going down like a rabbit hole and like throwing some stuff together, and like half of Lauren's job is being like, no, no, we need to like sell this stuff. So you certainly cannot just like we need to be selling building stuff for our customers. I'm like, yeah, that's actually true. Like, we need to stay focused. And I think as an answer, like maybe in a world where stable coins become a significant portion of payments volume for our largest customers, of course, we would support them better understanding who and for what purpose people are transacting with these financial instruments, because that's really what they are. Like they're just means of commerce. And a card is very similar to a stable coin in many ways. I think the thing we're excited about is like, you know, when you look in the future, like a gentic commerce and things like that. You know, we have a lot of data and helping our customers figure out who they should be letting these little AI agents transact with, if that's the future we're moving towards, is something we are in a very, very strong position to help with. Even if that transaction is happening with a stable coin built on one of these many, many, many protocols, or if it's happening with a card or an ACH or a wire, like deeply understanding who someone is transacting with is something we've been doing for a long time. And we do billions of times every single month. And I think that's a that doesn't matter really what the medium of exchange is. We'll figure out how to help our customers do it. So, not an expert. And maybe calling myself a hater is like, I don't know if I should go on the record saying that. I think I am actually. There was some moving skeptic. A skeptic, exactly. Axios called me that, I think, once. Um, so I'll take it.

Julie VerHage-Greenberg 37:50

There you go.

Oban MacTavish 37:50

Uh, but yeah, so it's not, it's not a focus for us today. But I think undoubtedly like we want to support our customers across every payment rail that's relevant to them. And if the volumes of these things become relevant, like we'll be right there with us.

Julie VerHage-Greenberg 38:01

Alan, so I think it was your partner, Matt, that was the investor in bridge, but I'm sure you've also like you know quite a bit about stable coins just given that that was in your portfolio and stuff too. What are your thoughts on this?

Career Advice For New Grads

Allen Miller 38:11

Look, I think I think Owen put it well in the sense that like for us right now, at least for from a US and Canada's uh perspective, right? In our current markets, it's probably not the most relevant. I think where stable coins become really interesting is when we start talking about international, right? Um, especially uh, you know, we do a lot of work in Latin America. Uh Bridge, you mentioned um a lot of their customers were in Latin America. Um, you know, in those in those markets, stable coins are actually very important, right? They're a very important way, not just to do transactions with merchants like consumer merchants, but also employees getting paid out, right, in stable coins, uh holding um savings in stable coins, um, dealing with um international remittances, right? So that's actually, you know, I think if you look at the growth rate of stable coins in some of these emerging markets, particularly in Latin America, you're seeing an incredible adoption. And to the extent that Spain eventually does some work, you know, I think this is probably, you know, Oban will know better than I do, but um I think this is probably yours down the road here. But to the extent that we do go into some of these international markets, and ultimately we want, or the the our customers want to see data from merchants that may include stablecoin as a rail, right? Because we do cards, we do ACH, we do wires, we do RTP, and maybe there's a world down the road where stable coins is a is a you know fourth or fifth rail. Um I could see that potentially being interesting to our customers. Um, and actually, it could actually be a very, very large part of business in that market, right? If we eventually go there. So, but I think Open's absolutely right. Look, I think we got to stay focused. We're a small company. I think we're what do we now, Oban, like 22, 23 people, um, something like that, right? So more than 25, maybe. Oh, 25. Okay. Okay. You guys have grown like what, 25% since we since we let it be?

Julie VerHage-Greenberg 40:02

Um They're putting the money to use, Alan. They're putting the money to use.

Allen Miller 40:06

Well, I love it. That's what we're that's what we're here for, right? So, but yeah, look, I think it's um I think it's I think it's one of those things where if and when that becomes a a goal for Spay to go internationally and go to some of these markets, then then it may be maybe relevant. And in the meantime, I think stable coins in general certainly have a role to play, um, you know, in as we've seen in some of our portfolio companies. And we're, you know, we're very um interested in those applications. But it's probably, I think it's probably a couple years for Spay to Okay.

Julie VerHage-Greenberg 40:33

And I actually want to ask all three of you this final question that I have. And it's the biggest advice you'd have for someone that is like a new graduate and looking to get into fintech. And the reason I want to ask all three of you is like Lauren, you have a sales role, and I think so much recently about I would hate to be a college student just graduating around because all the roles that are getting eliminated are ones that are by AI are the ones that are largely for you know new people into the system. So, what what advice do you have for someone that is, you know, either an undergrad or an MBA, just getting started out in either venture capital or at a fintech in particular, to be able to still like, you know, get into the system and do well like all three of you have?

Oban MacTavish 41:17

I think I have always felt like the thing that I've tried to do with my life is just like go where you can learn a lot. And I don't think that's I think in a at a time the I guess the world we're at right now where the future seems pretty uncertain, I think that's usually the best way to approach it. Like I don't come from tons of tons of pedigree. Like you look around, lots of fancy founders. Uh, I wouldn't describe myself as that. And I think a big part of where we are today at spade is just like willingness to just like do the dirty work and like go where there's interesting and things to learn. And I think every time when you're looking at opportunities at a time when there's a lot of uncertainty, I think trying to just like build your own knowledge and things you appreciate and like collect more information and like build yourself, I think is a surefire way to have a very interesting career and also expose yourself to things that like might be overlooked or underappreciated. Like, yeah, you can go work at like the the fastest growing, hottest AI company, or you can find these interesting things that really like spark your interest that you're gonna be willing to like work really hard at because just because something is like the coolest place to work, because like your dinner party conversations are great and has a great valuation does not mean it's gonna be fulfilling or interesting for you or your life. And I think really sort of focusing on what you find interesting and just like digging there and trying to find places you can learn, I think is the highest leverage use of your uh of of certainly, I think, of my time that's ever been. And especially if you're earlier in your career, I think that's how you can do the most interesting work is by prioritizing that, like a pursuit of like knowledge and understanding versus a pursuit of like um, you know, like flashy titles or things like that. I think that's something I see reflected in a lot of the founders and the people I respect who have sort of taken winding roads to get where they are. Um, yeah, that would be mine.

Lauren Crossett 43:00

Well, I started my career well for a moment. I like wanted to be a pro sailor. Uh that didn't really work out, but that's why I still commit a lot of time to it. So sorry, Oban. Uh but I I went to pass neutral and you know, I was a financial advisor, but that that role is really interesting because it does have like the big company opportunity of getting sales training, which I think is really, really important. Um, but then also like you're in business for yourself. So you have to figure everything out the hard way. And like I look at that role and think like, um, it's a little cringy for me uh to look back at. But it did give me so, so much exposure and experience. Um, I just don't know that a 23-year-old really is in a position to tell people how to protect themselves adequately. Um but like I think that's the thing I would tell people to look out for is like you you need to find a sales playbook if you want to be in sales, but you also have to have the opportunity to get very in the weeds. I think some people go to like really, really large companies that have very, very robust playbooks. And that's great for some elements of things, but it doesn't get you as in the weeds on like the specific elements of the thing that you're selling. And especially in FinTech, I think that's a superpower, like really understanding very deeply how the product works. I always say, like, I'm moonlight in product. I think that that's like the thing that you kind of have to do to really understand what you might be able to sell in the future, what conversation to seed, how to like ask the right discovery questions. And so, you know, maybe in today's world that looks like joining a startup, even on like a technical CSM role or like a junior analyst product role, where like you really get to understand um how the the sausage is made.

Final Thoughts

Allen Miller 44:52

Yeah, I think that's great, great advice, great feedback. Um, I have like sort of two different thoughts. One is more like meta and one is more like practical. Um, I think the the the first thing is like um just because you know I when I as I think back, like I I was always I was kind of a late bloomer, I always had like a lot of different interests, and I didn't really um kind of fully uh know exactly what I want to do. And I think a lot of people coming out of college or uh early in their career are kind of like that. I think the thing that I kind of wish I'd focused on more is like find the things that you're like really really passionate about where like work doesn't feel like work right where where you're just doing it because you love it you're spending all your time outside of your nine to five exploring that idea that that hobby that interest or whatever it is ideally it'd be something that's also hard right because like the intersection of things you're passionate about and things that are also really really hard the sort of overlap the sort of Venn diagram there is I think where a lot of the value in the world comes from is that that intersect. But sort of focused on finding things that you love and that you're just passionate about that where that that that nine to five or that work doesn't become work. It's just sort of like becomes a life um lifelong like passion for that what that thing is. I was just gonna say and then the and the other like very like tactical thing I think especially right now in 2026 is like just with the AI tooling and the AI um capabilities that are out there like I think you got to own those things and you got to be willing to like experiment and kind of become I think Bill Bill Gurley said this well become like the very best AI version of yourself that you can be in whatever kind of like job you're in, whatever industry you're in because I think the people who adopt this technology are going to be much more productive than their sort of average peer um and you're gonna get a lot more opportunities for advancement and for taking on new um new you know some new projects and you'll just see a lot more early in your career if you adopt this stuff because you become more efficient, more productive you'll be a sort of a rising star in the company. So I think like whatever role you're in whatever industry just like be the very like earliest adopter of this technology because we're in this like juncture here where like um the rest of the world is not going to catch up as quickly, right? And if you have a window here of two or three years um you can really accelerate and I think that's just something that every every person coming out of college should be thinking about also very good advice.

Julie VerHage-Greenberg 47:19

There was one piece of advice I got is think about the job you want after this next job. So like if you're want to be a sales manager or sort of like think about what you need to learn in that sales role in order to get like think always think about what tools you're gonna need to get to that job that you ultimately want, especially early on in your career. If you want to be a founder, think about finding a role that's a chief of staff or something like that. If you want to be an investor like Alan think about going to maybe investment banking or consulting where you're diving deep into these industries, et cetera. I think that was good advice too. But all of that was really good advice. So I hope people um especially the younger ones that are listening you know take all that to heart and and it can help some folks that are listening to this too. But thank you so much for joining me especially you know the day we're filming this the day after money uh not money 2020 fintech meetup uh the other Vegas conference um so you know people have less sleep and have been out in a uh highly oxygenated and dehydrated environment so I appreciate you taking the time to do this.

Oban MacTavish 48:23

No thank you it's great real quick