He sold his first startup for $100M. Then raised $250M in 18 months. | Dileep Thazhmon, Founder of Jeeves

Dileep Thazhmon (00:00:00) :
Every founder has this, but if you don't feel like your startup has died three times, right? You're probably not running a startup. A lot of times I see founders trying to do this perfect business model, and it's like, you're just a startup, can I pay you to use a product? If I can't pay you to use a product, there's no scenario that you can charge for the product and you get this complicated, oh, let's figure out this end state and a lot of things change. But the core thing is their value. Will someone use it, ideally for free? Ideally then pay you, you want them to pay but if you can't get it for free. You're not going to start with two days a day that you're just going to pay. So we did $1 million in about six months, and I think we were doing $7 million a little bit past a year. I think founders have to be sixty percent good at everything. Product was a great example, I would be on every single call every day. We had two standups. Obviously not good enough to scale it, but good enough to get it off the ground. I did the UX, I did the UI, I came up with the logo, you do everything and just keep it moving. It doesn't have to be perfect, don't overthink it, just get to the next stage. I had a very different philosophy as a second time founder on Seagrant. I want to have as many people as possible, because then they are invested in the outcome in Jeeves.

Previous Guests (00:01:09) :
That's Product Market Fit. Product Market Fit. Product Market Fit. I call that the Product Market Fit question. Product Market Fit. Product Market Fit. Product Market Fit. Product Market Fit. I mean, the name of the show is Product Market Fit.

Pablo Srugo (00:01:21) :
Do you think the Product Market Fit show, has Product Market Fit? Because if you do, then there's something you just have to do. You have to take out your phone. You have to leave the show five stars. It lets us reach more founders, and it lets us get better guests. Thank you. Dileep, welcome to the show.

Dileep Thazhmon (00:01:38) :
Thanks, Pablo. Great to be here.

Pablo Srugo (00:01:40) :
So yeah, excited to talk through the journey. I mean, you're certainly at least on your second startup. Maybe you had a few more, but I mean, we talked a little bit earlier. You had one before Jeeves, which is the one you're on right now. That's raised over $250 million that you sold for over $100 million. So maybe let's start there. Obviously that'll tie into the origin story for this company here. So tell me a little bit about maybe your background and certainly your previous company and what that was all about.

Dileep Thazhmon (00:02:04) :
I'm an engineer by training, so I have two engineering degrees from a long time ago. Right now, I wouldn't be as good on the engineering side, although it is cool seeing all of the stuff at AI. Where I actually feel like I can start pretending I'm dangerous and then I went to Stanford for my MBA, and after that started a company in the marketing automation space. So very different time, probably about ten years ago, and we raised about $18 million from a lot of investors, and we exited that for about $106 million. And the goal of that company was really to provide marketing automation inside emails. When you open your email, how do you match the person to the content, and so on. And then Jeeves, which is my company now, is just in a completely different space. We're building the first global business bank. So think of it almost like a B2B Revolut, but a lot of the lessons that I learned from my first company, Power Inbox, was the stuff that got me to where I am today. Which is still a long way to go, but it's one of those things where the lessons keep propagating from the first startup.

Pablo Srugo (00:03:02) :
So we'll get into Jeeves, but I'd love to learn a little bit more about Power Inbox, your last company. Marketing automation, that's kind of the high level, like what exactly did you guys do?

Dileep Thazhmon (00:03:10) :
Yeah, so if you think about what Google does on the web, we did something similar in email. So think about if you're a Starbucks and you want to reach an audience that's, I don't know, upper middle class professionals in New York. How do you do that in email? So we would do the matching of the content, the targeting of the person. So basically ad serving infrastructure and then the automation that comes with that. The issue was that space just wasn't that big. It is one of those things that you also learn, you know, investors keep talking about the TAM, and the market was just not that big. And we were one of the top players. There were about two or three. We were, you know, we had a decent amount of market share but the scale was just not there and so we eventually exited that to another company that was doing something similar on the web, and wanted to get a play in the email space as well. So it's very different from where we are today, but it was one of those things where it's interesting. Because I don't think I woke up one day and I'm like, oh, you know what I really want to do is solve email marketing automation. But it's one of those things where I knew I wanted to start a company and I actually started that company with my brother,. Which is also a very interesting experience of working with someone that's family, someone you trust. and, you know, there are things that you learn from that as well.

Pablo Srugo (00:04:17) :
Do you recommend it on Net-net?

Dileep Thazhmon (00:04:20) :
Yes, I think the biggest thing with founders is you need someone you trust and the thing you have with family, good or bad, is usually that trust. The flip side is a lot of your relationships start skewing into work. Everything becomes a work component and it's pretty funny, we, you know, given you're brothers. You'll still have these things where, you know, my mom would give me a call, and I'm like, why are you calling me? You don't even know what we're arguing about, right? You know, but it's just  your family, it never changes and again, just to be clear. We also raised from Battery Ventures, venture funded company, went through Series A, Series B. But, you know, the founders, at least for PowerInbox, was originally me and my brother.

Pablo Srugo (00:04:58) :
And just want to understand, you would help like Starbucks segment their own email list or you would provide new emails to them to market to?

Dileep Thazhmon (00:05:05) :
Yeah, so think of CNN sending a daily newsletter, top five news items this week. In that newsletter, there'll be a top ad and a bottom ad. That ad they would sell to Starbucks and say, Starbucks, look, you want to reach our audience, you can get the ad. The people that would provide the infrastructure for them to find those people, that was us. So a similar way, very similar to Google and Google's obviously massive operation that does the same thing on the web, and web is one hundred times bigger. But the same concept, which is how do you use the content to find people? And then you have, you're matching the content provider. Which is CNN, with the advertiser and then ideally the end user that wants to see the ad.

Pablo Srugo (00:05:41) :
When did you sell that company?

Dileep Thazhmon (00:05:43) :
That was in 2022. So that was in 2022, I had already left to start Jeeves. So I wasn't there for the last two years or so of the company. But yeah, that was right after COVID.

Pablo Srugo (00:05:55) :
Were you CEO of that company or was your brother?

Dileep Thazhmon (00:05:57) :
I was COO of the company. We actually merged with another company, and the person running that company became the CEO of the combined entity.

Pablo Srugo (00:06:05) :
And how did you decide? I mean, it's a big deal to leave a company where you're kind of a C-level founder type of. Why did you decide to leave that company to start Jeeves?

Dileep Thazhmon (00:06:14) :
Yeah, that's a really good question. I think there's a few things you kind of need to balance, right? One, I was getting to a point where I wasn't really learning a lot, in the sense that we had a good operation, it was running well, we were making money, we were profitable, but one of the things I really try to push myself on and I see this in founders, is your time is your most valuable asset. And, you know, there's time periods where you feel like you want to go all in, and there's time periods where maybe, when I'm older and I'm like, hey, this is not my cycle of working a hundred hours.That I don't want to do it. But at that point, I wanted to just like at Jeeves is a twenty hour a day, full throttle kind of business. But I wasn't learning at the velocity that I wanted to learn. The curve of learning was really flattening because it was just a well run, sustainable business.

Pablo Srugo (00:07:04) :
Was it at scale or what it was doing kind of tens of millions in revenue sort of thing, like size wise?

Dileep Thazhmon (00:07:08) :
Yeah, it was north of that. It was north of $50 million at that point and so it was at scale. Well run business and then, you know, it just didn't have the same challenges, good or bad. I've learned some people, they just like the part of the challenges and so I didn't have that. That was one and then two, honestly, the space, if I'm being completely candid. I was getting a little burnt out on the space itself, where I was just like, I don't know if I want to do this for the next fifteen years of my life, right? And thankfully, you know, I had the ability to kind of think through other areas, and it was a little bit of an open slate. And I get this question a lot from founders is, how do you decide what to do next? There's no good answer, but I looked at probably a different company. Like starting a different company, one was in the health space, one was in kind of financial infrastructure, a little bit different from Jeeves. But eventually this is the one that kind of clicked and it's a little bit of like, what do you feel like you can contribute that's special? How big is the actual market you're solving? And then is there some special timing component? COVID was one of them that is pushing kind of an output for what you're trying to build. But it was a little bit of like, I knew I wanted to start something again. I just didn't know what and so it took me maybe about a year of thinking through options before kind of deciding on Jeeves.

Pablo Srugo (00:08:19) :
Yeah, walk me through how you ended up deciding on Jeeves. You mentioned some of the elements that you thought about, but maybe just more of the specifics. Because what you decide to start is a huge determinant of where you could possibly end up and a lot of times, especially for first time founders. It's funny enough, maybe not giving enough thought, a little bit like your first business. Which obviously was still successful, but it's like, I just want to start something. This thing happens to me in front of you. So you go and you do that thing. And in some cases, good cases, you end up with a solid exit. In other cases, you waste five years of your life running down a path that leads to nowhere. I mean, what was it about Jeeves that pulled you in relative to the other things that you were thinking about?

Dileep Thazhmon (00:08:54) :
Yeah, so it's a really good question and I think you have to find a few things that you really like about what you're trying to solve. So what I'm trying to get to is you need to at least fall in love with the problem, independent of the solution. It should be something that you personally care about and it could be anything. But it's at least something that is intrinsically motivating to you. You want the extrinsic motivation, you want to raise, you want a good outcome, everybody does, but is that challenge something that you are motivated to solve? Because if it is, it'll push you through a lot of things that someone that's not intrinsically motivated would get stuck on. I'll give you an example, I looked at something in the health space and I looked at it for about three or four months, and I just got to a point where I'm just not that excited about this problem, and it took me three months. It took me three months of, like talking to people. It's like, okay, what does this look like? Let's set it up, let's beat it down, is it still standing? And then when it came to Jeeves, that was one where three months in, four months in, beating it down, I'm like, this is interesting. And from an intrinsic perspective, I'm like, how do you solve banking for a company that's doing it in three countries? How do you solve it? That's the problem and then you kind of build all these things around it. But the core thing was something that was very intrinsically motivating for me, in a way that a lot of the other ones were not. There's no blueprint for it, I literally had a spreadsheet. I was going through ideas, kind of like, okay, is this something I can contribute to? Is this something that's just a good idea? I'll give you an example. I looked at one of the IVF spaces, which is a really interesting area. Very fragmented, people spend a lot of money, everybody wants a good outcome, you're motivated to have children. So you have kind of buyers that are motivated. But it just wasn't something that I knew inside out and it wasn't something where I'm like, oh, I can spend ten years of my life doing this. And I think people forget how hard startups are in the sense of how much time it takes you to get to an outcome that's just a decent outcome. Not a big outcome, but just because you see these big companies and we also did that. We raised three rounds in twelve months. We raised $250 million in twelve months, right? It happens, but that's not the outcome that just gives you the fuel of what you want to build and you really like it. And it's been four years since, we're still building. You have to put in the time, and you have to find a problem you're excited about. And I have this thing that I've heard, and it really resonates with me. Which is you have to fall in love with the process of building and not the outcome. Because the outcome might come, it might not come, you don't know. There could be things that change. So the regulations change, you build this for four years, now Bitcoin is crazy. Nobody wants to touch it. That's happened, right? And then two years later, it's like, oh, we love Bitcoin. You didn't control that. But you have to enjoy the process of building and not the outcome. And if you enjoy it, more chances than not, the outcome will come. Because you have enough going that you'll push to get that outcome.

Pablo Srugo (00:11:36) :
And tell me a bit about the idea for Jeeves. How do you fall into this world of banking in general and specifically like multi-currency, multi-country?

Dileep Thazhmon (00:11:44) :
Yeah, so a few thoughts there. One, Jeeves by nature is a global company. We operate in twenty five countries. We provide business banking. I had no banking experience before this, and I think that's one of the reasons I looked at it as, how do you do this at scale in twenty five countries? Because if I did, which I do now. I would realize how complex it is and how much regulation, and compliance there is, you know, it's banking. It's not like you're just doing a SaaS thing and just turning the wheel. A full operation, you need to have compliance, regulation, etc. But sometimes that naivety is a good thing. The fact that you're an outsider is a really good thing because you don't look at it the same way. If I had twenty five years of banking experience, I'd just be so coded in a certain way of, well, this is deep, I can't do anything more. Let's just do one country, then add another and because you didn't have that. Because you were an outsider, it actually gives you a huge advantage of how to think about things in a different way and so, just going back to the question. My last company, we operated in two countries primarily and in those two countries, we needed two different corporate cards.

Pablo Srugo (00:12:44) :
U.S.? I assume it's U.S. and another country?

Dileep Thazhmon (00:12:47) :
It was U.S. and Israel. So we had two different corporate cards, two different bank accounts, two different payment rails. It would take us thirty to forty five days after the month closed to know our cash position for last month and that's very normal. I mean, that's just how businesses operate, right? And so if you want to solve that, the core part that I was realizing is you really need to own the infrastructure. Because otherwise everything is in a silo, and the silo is then locked in one country in one currency. So it's not just a silo, it's a silo in a box in a rhythm, you know, it's like three or four layers just to get the information out and the only way to solve that is you have to have an abstraction layer that sits on top. Which is really the core of what we're building. Which is just, you know, I can go very deep into it, but if you think about card issuing, for instance, we do a lot of that issuing directly. So the transaction data sits with us. That's the crux of what we're trying to solve. But it is a big, very hard, challenging problem because you have to build infrastructure at scale.

Pablo Srugo (00:13:38) :
Yeah, let's maybe take a little bit tangent just on the context in banking in general. Because global and remote and stuff has made a lot of this stuff maybe more top priority for people. Maybe my first question is, Deal is another company that's not a banking company but more on the payroll, HR side. But that's how you would think of, they're solving the, you have employees in different places, you're solving that, you're taking money from different places. Is that a good way to think about it, simple terms?

Dileep Thazhmon (00:14:00) :
It's exactly that. Both are coming on a central thesis that companies are going global faster than before and it's almost the default now. Companies are global by default. So that's the thesis and then they. I mean, amazing, amazing company coming at it from the aspect of payroll. Which is core, and we're coming in at the aspect of banking. Which is also core, but it's a different side and at different pluses and minuses, and they're built an amazing business. But yes, the core item that you're trying to solve is exactly that. Companies are going global faster. They need to have banking infrastructure that's global by design. Today, banking by design is country specific and currency specific. How do you solve that?

Pablo Srugo (00:14:36) :
So then moving into banking, even if you bank with, let's say, JP Morgan, right? Some massive, massive global brand, you still. If you're in different countries, you're going to have to have different bank partners in each of those countries. Is that like the status quo before something like Jeeves?

Dileep Thazhmon (00:14:51) :
Yeah, so just think about a company that uses us. We have this company called Hotmart in Brazil that uses us in nine countries. In those nine countries, they only have one expense management provider, us. They don't have one for the U.S., one for Germany, one for Brazil, local language speaking for Spanish, like it's just one. They only have one payment provider. I mean, I'm sure they use the banks, et cetera, but we become their operating kind of system that we provide, and so one login, you see all of this information, you get all your card.

Pablo Srugo (00:15:19) :
This is on the expense side or also on the transactional side?

Dileep Thazhmon (00:15:21) :
On both. So we provide full banking services for cards, which is our core flagship product. It's expense management, employee spend, et cetera. Then we added payments. So you need to do local and international payments. So think about AP, which is actually a much bigger box of spend than cards. Cards is a small component, but it's a good wedge to get in. But AP volume is ten times bigger than cards and then we have started adding deposits in Brazil, for instance. Which is one of our key countries to cover twenty five. We are filing to become a full bank by next year as well. So really, again, just going back to the thesis, it's how do you do business banking at scale? How do you build a global B2B Revolut, and our target is companies that are enterprise companies that operate ideally in more than one country.

Pablo Srugo (00:16:02) :
But to be clear, the status quo before something like Jeeves would have been you have nine different banks, you are in nine countries, you have one bank per country.

Dileep Thazhmon (00:16:08) :
You have nine different banks, you have nine different card providers, you have probably different AP, because each one is a different currency, right? So if you think of Bill.com, really Bill.com is a U.S. centric offering. If you were using this in India, you don't have Bill.com there. It's not going to work in India. You need to have an Indian version of Bill.com, which is there. There's absolutely a company that does exactly what it does. But you have to go cobble that together and then you have a team whose job is exactly that. Which is like, okay, we have twenty systems, how do we log into each system, get the information, put it into our closing for the end of the month, and then you go to the CEO and say, here's the number. That's the core, core reconciliation, accounting. How do you do that at scale in different countries? And by definition, it's not supposed to be interoperable because each country is different and each currency is fundamentally different and payment rails.

Pablo Srugo (00:16:54) :
It's a great example of one of these no brainer situations, right? In the sense that if you think about a company that operates in multiple countries. They would obviously rather have everything in one platform than across twenty different platforms. It's for sure, but you also assume that then, you know, the banks would see that and also solve it. How come things are the way they are? And especially from the perspective of, as you're starting to see this problem and think about it. I'm sure you're thinking about this as well. What are you finding out that maybe they don't know or that you're willing to do that they haven't done?

Dileep Thazhmon (00:17:23) :
I think, you know, if you look at companies like Nubank. I think it's a good example of the same gap that we're trying to lean into. Which is, banks are always going to be there. We're not going to magically remove banking's monopoly. I mean, they provide an amazing service that moves capital, you trust them, they're not going anywhere. But there are areas like this where it's really not in their interest to use all of their resources to solve this very structured problem of how do you do data in these many countries. If I'm a bank in a certain country, my goal is to make revenue, profit, be a good partner to my enterprises. My goal is not necessarily to solve this for the company that's in, you know, Mexico or the company that's in the U.S. That's where startups can be different  and so I don't see this as us trying to take market share from the bank. I think there's subsets of companies, especially enterprises that are global, that have very specific problems. That's where we can shine for them and I look at this really as an integrated offering, and if you look at how we think about the revenue breakout, it's really very blended. It's cards, it's payments, it's SaaS, and then there's deposits. So it has all the components of the banks in that whole revenue stack.

Pablo Srugo (00:18:33) :
But wouldn't the argument be that, you know, the biggest companies in the world are global and then if they deposit with you, they don't deposit with Bank XYZ? So is that not?

Dileep Thazhmon (00:18:42) :
Yeah, so it's a good question. So we use, obviously, our own system. We have twelve employees in twelve countries. We also still use J.P. Morgan. We also still keep funds in there as well, but our operating system, our day to day, that runs through Jeeves. There's no scenario that we're just going to be like, oh, I'm going to shut down my banking. That doesn't happen, but think about countries where we operate, like Colombia. You still have to walk into a bank to send a wire. You don't have to do that on Jeeves. That's just operational efficiency. It doesn't mean that the banks, by the way, they'll still keep cash in the bank. But you can build massive, massive software businesses at scale by providing that layer on top that makes it easier, that controls where you put a payment, someone else approves it. That's great, the bank's not necessarily going to build that because that's not their core offer.

Pablo Srugo (00:19:28) :
Gotcha. You mentioned that you would, you know, look at these ideas for maybe three or four months at a time. What did you do during those three or four months, the first few months where you explored the idea of Jeeves?

Dileep Thazhmon (00:19:38) :
I had kind of a little bit of a system where, one, I would try to write out just the core problem you're trying to solve and then two, try to beat the crap out of that assessment. Just every possible, like, why is that right? Okay, why are they not doing it? Okay, if it's such a great idea, how come no one else has done it? What's so brilliant about how you were thinking about this completely being, and not just me, like talking to people. Okay, you know, like this IVF, it was a really good example where someone should do it. It's very fragmented. The outcome, you know, you want a successful outcome. Have you been to any of these places? They look like hospitals. You're not induced to have a successful outcome. All the things you need, but then I'm like, I don't have the skill set to be able to solve this problem. Someone else should do it, but I don't have that skill set. So I would talk, like I talked to a doctor for that. Who's in the space, like, why is it like this, right? So basically, how do you come up with a problem statement? How do you beat the crap out of that problem statement? And then is it still standing? If it's still standing, then you focus on one KPI. Just one metric, either revenue, growth, number of companies, signups, waitlist. One, just one, and see if that number can move. And that's kind of what we did with Jeeves, which is just one KPI. And a lot of times I see founders trying to do this perfect business model. And it's like, you should start with, can you give the product for free? You just start with, can I pay you to use the product? If I can't pay you to use the product, there's no scenario that you can charge for the product and you get this complicated, like, oh, let's figure out this end state, and a lot of things change. But the core thing is, is there value? Will someone use it ideally for free? Ideally then pay you? You want them to pay, but if you can't get it for free, you're not going to start with, like, today's the day that you're just going to pay. I mean, there are other models like that, but I'm just saying in the core model, it has to have some intrinsic value that the person's going to say, okay, I'll try it and so that was my second stage after beating the problem. They're like, okay, this problem is still standing. The question was, can we get cards to companies internationally? And then can we get them to use those cards? That was it, that was our focus that was the goal.

Pablo Srugo (00:21:32) :
So what was the KPI, like total payment volume to the cards or number of cards issued?

Dileep Thazhmon (00:21:36) :
It was number of cards issued and transactions on the card. So basically, and you know, today we cover twenty five countries. We have local cards in all twenty five countries. We started shipping U.S. cards, and we just ate the FX. It's not a good business model, but it shows there's demand and then I'm like, okay, now let's go get licenses. Do we have licenses in all these countries? But if I sat and I was like, oh, I can't start until we have card issuing in twenty five countries, I'd still be there. I'd still be waiting. It takes time to kind of get to this point. So we just took U.S. cards, shipped them to these countries. We ate the FX fee, but clearly it was tapping into a demand where people are like, yes, love it. I will take this to people like, can you open this country? Like, oh, sure, let's try this country, right? And so you just have to be malleable as long as you have that one KPI, which for us was transaction volume and number of cards, like one meaning two.

Pablo Srugo (00:22:25) :
You told me a little about the IVF kind of three to four months. But with Jeeves specifically, who did you speak with, and what were some of the things that you heard that made you just double down on this opportunity?

Dileep Thazhmon (00:22:35) :
Yeah, so take a step back. If you look at what we're doing, there were examples of what Jeeves is, obviously in the U.S. Amex, Brex, Ramp was coming up, clear examples, clear market. The question was, no one had done this at scale internationally and the reason. Part of what I realized from talking to people, is if you look at the U.S., it's a large single market with a single currency. If there wasn't competition, I would just do the U.S. as well. It's much easier.

Pablo Srugo (00:23:00) :
You would have done Brex? That would have been the obvious thing, yeah.

Dileep Thazhmon (00:23:02) :
That's exactly right and so now, if you look at a company in Mexico and the company is growing, what do they do? They actually go to Colombia. They actually go to the U.S. That's how they increase their TAM. Now they have the core problem, which is they have multiple cards, multiple currencies, multiple banking systems. So by definition, the geographical countries we're looking at, these companies that grow to increase their TAM, they have to go to other countries. So they have a different core problem than just the U.S. centric focus. Which is, again, if they weren't there, we would probably do the U.S. Because it's just a massive, massive market and so that became the core part of like, okay, how do we solve this? How do we solve this for a business that operates in Mexico, Colombia, and the U.S.? And then it came out to like, the only way to really solve this is to build some of the stack yourself, right? And so in the beginning, what we did was we focused on, and we were in Y Combinator. So we focused on Y Combinator companies that were operating in more than one country, like startups, and just being like, hey, can you use the cards in both countries? We'll give you cashback, we'll give you all these things, but just, is this resonating for you, right? And when we started seeing the usage, the adoption, then we started thinking through, okay, how do we actually go build this in these countries? I'll give you an example. In Mexico City, the first time I flew there was for Jeeves. So it's not like we had some deep background in Mexico City before, but we then hired our first hire, who was the GM based in Mexico City. You have to hire someone local. You have to hire someone that knows the market. But I don't need to know every single market. I mean, that's not the business that we're building. I need to know enough that I can help push an outcome that the person running the market needs. But in every country, you need someone that's local, someone that's in Colombia, someone that's in Mexico, someone that's in Brazil. I cannot run Brazil from here. It took us a year and a half to realize that, but you need someone that's fully local.

Pablo Srugo (00:24:44) :
You just mentioned you went through YC. I mean, YC is obviously very well known. A lot of founders want to go through it, but I find it's mainly first time founders that want to go through it. You'd already had a very successful exit. You've been through the startup world for about ten years at that point. Why did you decide? Because you do have to give a meaningful amount of equity, right? To get into YC, why did you decide to do it for Jeeves?

Dileep Thazhmon (00:25:03) :
So there's a few reasons. One, again, this is kind of the thing with startups, right? When I was starting this company, this was March of 2020. So, I had just kind of wrapped up with PowerInbox at that point. I was starting this and I had talked to a VC fund and they said, look, we'll give you $3 million for $15 million post, and that's it. We'll take the whole round. Great, ideas resonating and then COVID happened, right? And COVID changes a lot of things, and they were like, we're not able to get there. And it was a little bit gut-wrenching where I'm like, oh, we had planned on this, blah, blah. And then you just have to focus on, okay, what is the best option at this point? And YC made a lot of sense. One, because we were going B2B, like the product is only B2B, it is not B2C. We're not doing consumer, it's all enterprise business, et cetera, and then two, there was a lot of uncertainty with COVID, and the fact that you're coming from YC gives you credibility. Especially in markets where I'm not native to, right? I'm not native to Mexico, Colombia, etc. These are markets we operate in. Having that brand really, really helped and then the third thing was that even though I had started a company before, this is a very different space. And having exposure to folks that had that background in fintech was very helpful for me. And so they have been very, very helpful even since that point. But I would do it again. I don't know if I do my third company again, but I would do that same position again because I think it really helped change the trajectory of the company. There was a lot of uncertainty, people forget 2020. It was a lot of uncertainty, you didn't know where this was going. You didn't know if COVID was going to be a fire thing.

Pablo Srugo (00:26:34) :
Yeah, there were two or three months there, like the second half of March, April, May. Where it was just, oh my God, is everything ending? Is VC done? Are startups over? It was nuts.

Dileep Thazhmon (00:26:44) :
And you have some cycles. It's funny you bring this up, and I was reading this thing, and every founder has this. But if you don't feel like your startup has died three times, you're probably not running a startup. But this is one example I remember: our last round, it was supposed to be funded at the end of February 2022. Which was, by the way, when the Russia-Ukraine invasion started, and that was another whole cycle where people were just like, literally the day of funding. We're done, we don't know what's happening, we're all pencils down, we got to see and we managed to get that round through. But the thing is, people never see this. They just see the headline. It's like, oh, that must have been easy, but it's never as good as it seems on the outside. It's never as bad as you think it is on the inside and the truth is somewhere in between. And you as a founder have the most information, so you see every single day, the warts and the pluses, and you have to have that balance. And I do think being a second-time founder, that's one of the benefits of doing it the second time. Because it's like you don't puff your own hot air. It's just like, okay, I get it, but we still have a lot to do.

Pablo Srugo (00:27:43) :
You love this show, you don't want to miss the next episode. So hit that follow button. Trust me, it's in your own best interest. It's funny. I mean, when you start a startup, you think through and you have a good sense of all the different risks, and the things that could happen to your business. But you rarely realize just how many things outside of your business might be the thing that either completely screws you up or actually gives you a huge tailwind that you never imagined. It's hard to predict.

Dileep Thazhmon (00:28:11) :
It's a great point and one of the quotes I love from, I think, was Ben Horowitz's book is kind of like just making sure your startup is alive long enough to survive the changing pieces. It's like a game of chess, but the game changes. The game changes next year. AI is a fantastic example, a lot of startups didn't make it to the point to survive with AI and part of your job as a CEO, and a founder is to make sure that you survive. And then you thrive because you're surviving. But the game itself changes, it changes every year. I mean, the regulation, the Genius Act, we're doing a ton of things in Stablecoin now. We couldn't do that two years ago. I couldn't go to a bank and be like, I'm doing Stablecoin. They were like, get out of my room. Now it's like, oh, cool. What's your Stablecoin plan? What's your, like, I get people asking me this and that's fundamentally changed. The product technology hasn't changed. It's just exactly to your point, things you don't control have changed. But now, because we survive, because we're strong, we get the chance to fight again and put that new technology in. So a big part is just surviving and knowing that the game itself is going to change every year.

Pablo Srugo (00:29:15) :
When do you graduate YC?

Dileep Thazhmon (00:29:18) :
Summer, so September 2020.

Pablo Srugo (00:29:20) :
And what is, when you talk about MVP in the context of building startups. What is the MVP for something like Jeeves that is fundamentally a bank, multi-country, it's just big by definition?

Dileep Thazhmon (00:29:32) :
Yeah, so we had three stages basically. The first stage, which is still our core flagship product, is the cards. Basically, how do you do cards in twenty five countries? We're full local issuers in Mexico, Colombia, Brazil and so when we started that, that was the core. How do you do cards in these countries that you're covering? How do you even get the cards? By the way, people forget this, but usually if you get a card in the US and you're in Argentina, you have to get the actual card to Argentina. So you got to figure out how to ship the card, right? It's not like just the cards show up one day. That also wasn't there. We had to figure out how to do this. We put it into envelopes, get it into FedEx, send it to Argentina. It's all things that don't scale, right? The YC mantra, none of that scales but it shows that there's demand. It shows that there was PMF.

Pablo Srugo (00:30:17) :
And these were cards. These are just American cards. You're just paying FX, but you're telling people, hey, you can spend anywhere. You can get anywhere.

Dileep Thazhmon (00:30:21) :
Yeah, U.S. cards work everywhere. It's just not a long-term, you can't really run a business using U.S. cards because you'll just get two percent fees on everything you do, right? Which is not sustainable for a business. But you can absolutely use the card, just like when you travel and use the U.S. cards, you can use it there. But it was more to do exactly what you're saying, PMF, prove that there's demand and then once you prove there's demand, then you start tightening things around it. Okay, you've shown that there's demand. Now can you show that you can do this with locally issued cards? Okay, you've shown this locally. Now can you do this without cashback? Okay, you can do it without cashback. Now can you show that they'll pay you for this? I mean, that takes two, three years, right? It's not like one day, but it's a sequence. It's like, if you don't do step one, you don't get the right to try for step two. It's like a Mario Brothers level, right? You don't get level two if you don't get through level one and level one is just basic. And then level two, it gets more and more advanced.

Pablo Srugo (00:31:11) :
Exactly. So, to be clear then, your first MVP. Let's say, was just cards anywhere and that was kind of like PMF for anywhere.

Dileep Thazhmon (00:31:19) :
Yeah, we started with about, I would say, all of Europe, UK, Mexico, Colombia, Canada, U.S. We didn't have Brazil when we started. We added Brazil a little bit later, but we still had, you know, twenty plus countries and the goal was exactly that. Can we get cards to these countries?

Pablo Srugo (00:31:33) :
And these are credit cards, debit cards, both?

Dileep Thazhmon (00:31:35) :
Charge card, so thirty-day, very similar to, basically we would give you credit for thirty days and all only enterprises, and then at the end of thirty days, you'll pay us back. So if you think about that, one of the things we have to solve is how do you actually underwrite the risk of these companies, right? Because you're giving them thirty days of credit, how do you get them connected on applied equivalent in these countries? For instance, you can see what's in their account and so we had three rules for countries we wanted to operate in. So one, do they have what we call Fintech V1, which is the ability to look at bank accounts, open banking? There's some way to reduce the risk so we know what we're looking at. Because some of these countries, like it's the first time we're operating in Colombia. How do you assess risk? So that's one, two is the government opening up to fintech? Is there a regulation that's moving in that direction? Brazil's a great example, I think they're very forward thinking in how they look at working with fintechs and then three is their capital flow. So, is it like US, Mexico? Fantastic example, there's capital going back and forth. They need this product. If you have all three, it gives you a lot of breathing room to make little changes if one specific thing is not going in your direction. I think one of the things that we, good or bad, by chewing such a big problem have in our benefit is that it has a lot of complexity, but it also has a lot of levers. Okay, one market is tightening, you can open up the other market with more fees. Or this fees is tightening, okay, let's add payments. You're not just doing cards in Mexico, and then Mexico changes some rule and the business could go down, right? You have these multiple levers, multifaceted business that you can kind of play with. But yes, to start, it was exactly what you said, it was cards. In these countries, we ship the cards ourselves. A lot of it was YC companies, which, you know, is one of the other benefits of YC, you get an inbuilt kind of PMF.

Pablo Srugo (00:33:20) :
Were these YC in your batch, very small or was there a way for you to access the true like at scale YC companies early?

Dileep Thazhmon (00:33:26) :
In the beginning, it was small. Some of them even to this day still use us, but it was really folks in our batch, hey, you know, this is kind of a service.

Pablo Srugo (00:33:34) :
Tell me about that. Because I mean, a lot of the small companies that are YC based would start selling B2B SaaS at that time in the U.S., right? 

Dileep Thazhmon (00:33:41) :
Yeah.

Pablo Srugo (00:33:42) :
So what were some of the companies that would have used you in all these countries?

Dileep Thazhmon (00:33:44) :
So we focused on companies that were based outside the U.S. and not necessarily just our batch, to be clear. So for instance, we would look at, have there been companies that came out of YC that have HQ in Mexico? Because if they have a headquarters in Mexico, they can't be onboarded by a US expense management provider. Because you need a US entity for that. So by definition, there's a gap, right? And so then we'd be like, hey, here's what's unique about what we can do. We can onboard a Mexican entity. We can onboard a Colombian entity. We can onboard these entities and give you cards against that, right? And so that was kind of the difference to start. But we started small. I mean, it was not like, I mean, today we have BMW, Lululemon, H&M, obviously we didn't start with that. We started with companies that still use us today, like Bellevue is an example, they're a YC company.

Pablo Srugo (00:34:29) :
And was that first product, was there a UI, like a Brex type UI for expense management? Or was it really just, hey, now you don't have to pay FX when you've got your card so you can at least do stuff?

Dileep Thazhmon (00:34:38) :
Good question. So we definitely had a UI, and I think I've said this to our team. I think founders have to be sixty percent good at everything and product was a great example. I would be on every single call every day. We had two standups. Obviously not good enough to scale it, but good enough to get it off the ground. I did the UX, I did the UI, I came up with the logo, the line, you do everything and just keep it moving. It doesn't have to be perfect. Don't overthink it, just get to the next stage, right? And so yes, we had a UX. I mean, this is a great example. We actually, because it was such a complex product to start. We had to get outsourced help to help build it because, think about it. How can I hire five, six, seven engineers when we are two people. There's no budget to even do that. So you either say I can't do it, or you figure out a way with the budget you have. So obviously the product's much, much stronger, stable, all of that stuff. But in the beginning it's just, you had to log in, it was functional, you saw your card transactions, you had your limit, you had some very light analytics, and then that was it. And it just told you what you're spending on, you see it in there. We did have, right from the beginning, the virtual cards. Which was the ability to create cards, freeze them, unblock them. That was a fairly big delta in some of the markets we were operating in, like in Colombia, Mexico, that wasn't as common. So that was a big differentiator that we did have from day one. But we tried to keep it as functional as possible in the beginning.

Pablo Srugo (00:36:03) :
By the way, in terms of market size and just trade. I mean, Mexico, Brazil make a lot of sense.
Why Colombia?

Dileep Thazhmon (00:36:08) :
Yeah, so Colombia is interesting because a lot of the companies that we operate with there tend to be actually larger. So they tend to be public companies more than even Mexico and Brazil. And again, I don't see us replacing the banks, but I think just from an operational perspective. You get to punch above your weight, and I think that's one of the benefits of where we operate. Because if we were in the U.S., you'd be slotted in as your mid sized, here's your CAC, and here's the small segment that you can play, and if you want to go above that or below that, not happening. Whereas because we get to operate in Mexico, Brazil, Colombia, all these markets, we get to punch above the size of the company with these very large companies that we wouldn't be able to do in the U.S. So for us, it was both Colombia itself, but also again, going back to the original thesis. If you're a Mexican company and growing, you're going to end up in Colombia at some point and then to service that Mexican company. We need to cover Colombia or vice versa, right? So it wasn't just Colombia itself. I kind of call it a network, right? So the value of Jeeves is better the more countries we cover. Because even for that company in Mexico, now we cover Spain, big corridor, Spain to Mexico. We cover that, we can give you a card in Spain. Your founder lives in the UK, we can give him a card. So it becomes more valuable the more countries you cover, because the core product is almost like an exponential value every time you add a new country.

Pablo Srugo (00:37:25) :
So you use the YC network to kind of get the first few customers, you issue some cards, and then what happens? What do you see in terms of usage?

Dileep Thazhmon (00:37:33) :
Yeah, so it's, it's interesting because I call, you know, PMF is one of those things that you can come up with all these definitions. But, you know, when you see it, if you don't know it, you probably aren't seeing it. It's as simple as that and it's a lot. All this, like, "Oh, growth rate." I'll, like, it's basically you're growing so fast that you can't keep up, and you're trying the best, and it's a great place to be in. And again, there's a lot I've also learned about PMF, right? Which is there's the initial PMF, then there's the, "Okay, but now we need actually a growing business," and then you start turning things off, and so you're tightening the PMF. Then it's like, is this the PMF with the right customer that you want? Because you could have PMF with different customers, and maybe some of them are a subset you want to grow with. And so, you have to also take a little knife and cut down your PMF. But the initial part that we were seeing was a classic PMF curve. Which is, you know, we were just seeing usage. People couldn't get enough of it. It was just like the spend was growing ten, twenty, thirty percent monthly. We were adding revenue. Obviously, the revenue is upside down, it's not profitable, but PMF is clearly, clearly there and it's almost to the point of, like, "Well, you know, the product is good enough," but clearly we can make this product ten times better. So the fact that it's working so well is because there's market demand and that's one of the big advantages I think we have even today. Which is because we cover so many countries, the demand for this type of product is high because we cover a lot of surface area. So you're not stuck in one region with one kind of offering. And we saw that from day one, and we just couldn't really keep up in the beginning. But I'll give you an example here. This is the thing that I think in the beginning founders get stuck on a lot of things. We started with cards, and then I remember our card provider wasn't ready at that point to go live, so we were basically using kind of the testing thing, and we were, like, blowing. I mean, testing is maximum, I don't know, one hundred thousand of volume, we were going past and they're like, "We are going to have to turn you guys off because it's not live. It's a testing program," and it's clearly, you know, more volume than we're comfortable with for testing. And we're like, "Okay, we need to move to another provider." And so, you know, I was challenging the team to do that switch in one month, this was December. Actually, I remember now, it was December of 2020. So exactly five years ago. So we had to turn off cards, switch to another provider. In between, we still had sixty days of, we need to figure out what to do and so we came up with this product. Which is today about forty percent of our revenue, which we call Jeeves Pay Credit. So basically, you can use our credit line. So let's just say you come to us, you're a BMW, we say you're a great business, you're doing banking with us, we'll give you $2 million on a thirty day card spend. You can now use that thirty day card spend for payments as well. So accounts payable and we ran that off of a spreadsheet, just completely covered with a spreadsheet.

Pablo Srugo (00:40:13) :
Just walk me through a little bit the difference just here in terms of AP accounts payable and just normal cards.

Dileep Thazhmon (00:40:18) :
Yeah, so cards is basically you get a corporate card, it's primarily used for travel expenses. So, you know, dinner, you're going to a restaurant, you're taking a customer out, that's kind of the core use case. Then the second box that is used for is really central spend. So AWS is a good example, Facebook ads, Google ads. Those are the big categories, cards just for that. AP, which is a much bigger box, is usually vendor payments. You need to pay anything else. You need to pay your rent. You need to pay for, I don't know, your e-commerce provider. You need to pay for just anything else.

Pablo Srugo (00:40:49) :
It's typically bigger ticket items.

Dileep Thazhmon (00:40:51) :
Bigger ticket, lot of volume and then if you think about it. They come to us saying, hey, we want to start with you on cards. But really, what we're trying to solve. What we Jeeves are trying to solve, is we want to be your hub for all spend. So it's spend management, right? It's not cards management, it's spend management.

Pablo Srugo (00:41:05) :
Because otherwise, you've got a vendor in Colombia, you've got to take it from your bank in Colombia and move it there. If you've got another vendor in Mexico, move from Mexican, you know, whatever there, and then US. The USD, move it there, and you're just doing all this stuff, and then you're reconciling, and you're, you know, oh my God, I have a lot of money. But the Colombian bank has no money, so now we've got to wire money over to the Colombian bank.

Dileep Thazhmon (00:41:23) :
Exactly that, right? And so we started with the cards, which is still, you know, the core kind of product but because we had this gap. Where we had to shift providers, we wanted to do something in that gap, right? And so basically, not just shut down the product for six or eight weeks, like nothing, right? So that would go to zero. So basically what we did is we launched this product called Jeeves Pay, and today that's about forty percent of our revenue. And today it's fully integrated, it's like accounts payable, you can go in. We connect, for instance, to the tax authority in Mexico. We'll download all your invoices. You click a button, we'll fill it in. You can send it out. Full accounts payable, we charge for that, right? It's a SaaS product at this point. It started because we had a sixty day cap where our cards were turning off and we were like, well, we have to do something. Okay, what if we try this, and it was all on spreadsheets. And what I'm just calling out there is in the beginning, you kind of are like a jack of all trades. And you kind of have to just figure out how to make it work, even if it's. You know, think about it, someone basically said, we're turning your cards off, go find another provider.

Pablo Srugo (00:42:18) :
And how did you do that, by the way? How did you lend that money out at that point? From where?

Dileep Thazhmon (00:42:22) :
The capital comes from our own. In the beginning, it came from our own equity.

Pablo Srugo (00:42:26) :
Which is balance sheet. OK, just because you had raised some money.

Dileep Thazhmon (00:42:29) :
We raised about $4 million, I think, on our seed round. So it was basically, I mean, that's how everything starts. You're not going to get a facility in the beginning. Now we have a, you know, a fairly large facility. We're doing three billion TPV, it's massive and you can't do that off a balance sheet. But in the beginning, it's just, I mean, it's $100K, right? So you raise $4 million, it's just rotating $100K or $200K, whatever the number is. So it comes off of that, but the product itself started changing from cards to cards plus payments and today, it's one of the benefits of us doing that so early. We're one of the few companies where that shift is almost even. Whereas if you look at other companies, even ones in the US. It tends to be very interchange heavy and our business is not. Our interchange is probably less than fifty percent of our revenue. Payments, which is core, is another forty percent and then SaaS is another fifty percent. So it's a very blended profile because of some of these, you want to call them hardships in the beginning. Because that forced us to think through, okay, what else can we offer? Now it's a big part of the offering that we have.

Pablo Srugo (00:43:21) :
Tell me a bit about your seed round. When did you raise it and kind of how did that happen?

Dileep Thazhmon (00:43:25) :
Yeah, so this is also a good point. I had a very different philosophy as a second time founder on seed round. I wanted to have as many people as possible because then they are invested in the outcome of Jeeves. It’s got positives and it has negatives of doing that, right? And so we had one lead, Urban Innovation Fund, that put in about a million out of that. I think it was $4.5 million, if I remember correctly. Everything else was small checks, and you have to do a lot of work to manage it. So some founders don't like that. They're just like, give me two people, clean cap table. That's awesome, but the way I was looking at my business, I need to grow in twenty five countries. The more people that are invested in Jeeves outcome, the more likely I can, you know, use them when I need help, right? But I'm like, hey, can I get an introduction here? Or we need to talk to the central bank in this country, do you know someone there? So my philosophy was to get a large round with as many people as possible for the seed and then the second thing. And this is something I learned from my first company, is just how do you construct the cap table? Which is basically you want to have someone that has potential to lead your next round in the round before, even if it's a small check. Because what you want to be able to do is give them insights into how you're doing before you go to them for the next round. And the one thing I've noticed with investors is basically you tell them, hey, we're here. Our goal is here. Then come back and say, now we're here. Our next goal is here, come back and say, now I'm here, I'm fundraising. Next time I come, I'm going to be here. That's when they take it seriously because they've seen you do it three times in a row and the only way that works is one, you can send this massive blast. But you give a few people, a select kind of preview and if we look at our Series A, B, et cetera. We had the folks that did that on the cap table in the prior round and so, Andreessen Horowitz did our A. I mean, I talked to them for one year. I talked to them from the YC, this to the seed.

Pablo Srugo (00:45:12) :
Were the investors in the seed or you just kept them?

Dileep Thazhmon (00:45:15) :
No, I had known them from pre-YC. So pre-YC and then the seed, and then the A. But then the A, the person that did the B, I had talked to right at the A, and then the one that did the C was in the B. So it's almost like a cascading thing. You can't go the first time and just be like, hey, we're here, give me $50 million, right? You need to have that build up of, like, hey, I came last time here and then they feel like, oh, this guy or girl is like doing what they said. And next time they come, I'm going to pay a higher price because they're clearly delivering, right? If you show them you can deliver, then the value of what you're saying is high and then the next time, they'll feel like, okay, when he comes back after this, I'm just going to pay more for the same company. If you're interested and if you're not, that's fine. You can just say, I'm not interested and move on to the next one. But one of the lessons I learned from my last company was just how to think about cap table creation.

Pablo Srugo (00:46:06) :
Tell me a little bit about go to market and go to market tactics. After the first few companies that you land from YC, what is the main thing that you use to acquire customers? What works best?

Dileep Thazhmon (00:46:16) :
Yeah, so because we cover these regions, my first hire, and just so you can step back. If you think about just infrastructure, how we're set up, right? If you think about a card stack, there's four components. There's a top of the funnel, customer acquisition, kind of go to market. There's a processor, there's a program manager. Which is regulation and compliance. And then there's the BIN, the bank identification number. So the numbers on your card, that has to be local for each country. What we do at Jeeves that's very unique is the first three sit on our own back using different partners. So when we go from Mexico to Colombia, we only need to change the number for the BIN. If you go from Colombia to Indonesia, which we don't cover today, we'd only need to change the number for the BIN. So it's a different model for a lot of entrants that go very deep in one country. But the flip side is we are very local for anything go to market and so the number one hire we need to do in each region, and usually the first one, is what we call the GM. The general manager and they are, you know, really kind of the owner of the region, but tend to be very sales focused. They're running the customer components, anything that touches it and that was the hire that we did for Mexico, Colombia. Fully local person on the ground and then we started looking at what's the most cost effective way to grow the base that we had. And part of what we had, I think that was very successful, is we had very strong word of mouth in the beginning. Because the product that we were offering, there was a real gap in the market and you brought up Colombia. There weren't any other players in Colombia and so, you know, if you're offering a product that doesn't require going to a bank for four months to get approved. It's got demand, people will tell people, and then they had a waitlist, and the waitlist was just signing up. I mean, we had thousands, tens of thousands of companies on the waitlist and so that was a big, big driver. And then the second thing that we did, which was very creative then. And I still get a lot of folks talking about, is we would go try to find areas we could put banner ads, not digital banner ads, that were cost-effective. And even today, if you go to the Mexican airport, you'll see our ads when you come in. And we've had that for five years, and it is incredibly cost effective. I don't want to share how much it is, but it is so effective compared to what you would pay for something else and think about it, you're a bank. Now I get people saying, hey, I saw you at the airport. You guys must be big. We're not that big.


Pablo Srugo (00:48:30) :
How do you even measure attribution, by the way? For something like that?

Dileep Thazhmon (00:48:33) :
It's the trade-off, right? You don't know fully, but just the brand. I look at it more as brand awareness, which, if you're fintech, if you're doing banking, it has a lot of value. Even if it's not directly CAC attributable to, they saw this and now they clicked on it. The fact that people see you in the ether, it goes a long way. But just as an example, in these airports. We would go in and say, hey, that wall doesn't have anything on it. Why don't we pick that wall? Not let's get the number one billboard that you have that you're already getting five other people competing for, it's just a wall. Why not get extra cash? But you have to think about that in a little bit of a different way and so we were looking at these angles where we're like, okay, how do we get placements? How do we get, you know, traffic in a way that increases the brand? And then overlaying that with some of the word of mouth that we had. Especially, because we were operating in countries that didn't have a lot of this, you know, product offering before we came along.

Pablo Srugo (00:49:27) :
And when would you say was a time when you'd felt like you'd found true product market fit

Dileep Thazhmon (00:49:31) :
Yeah, that's a good question. I think as we got into probably a year, a little bit less than a year. So six to eight months, I think that's when we were starting to see companies that we wanted to grow with coming to us. So in the beginning, you're, you know, a little bit of a taker. I'll take whatever is out there. You don't have the choices, you just take what you need, and then really everybody has this. Every startup founder, every company should have their target customers of who they want and what we started seeing about six to eight months in. Is those companies were coming to us, or if we went out to them, they knew what we were offering and that's when it started clicking. It's not just the growth, it's the growth from the companies that you want to grow with long term and so PMF is, you know, everyone says it's just this crazy growth hockey stick. Which is true, but you can get hockey sticks many ways. You can pay for it, you pay four dollars and you show one dollar of growth. It's possible, but then it's not sustainable. It's not long term, right? And so I think really what was starting to click about eight months and nine months in is we were starting to see companies. Even today, that are with us coming to us for the first time. Which are companies we wanted to grow with and that, I think, is a little bit different than just the initial PMF of like, oh, someone's just coming to us with the cards and using it, and we're seeing crazy volume.

Pablo Srugo (00:50:45) :
Got you, and was there ever a time on the flip side where you actually thought things maybe wouldn't work out, and the company might fail?

Dileep Thazhmon (00:50:53) :
Yeah, so I mean, the good news of where we are today is I think we've been through multiple cycles and I think going back to your earlier point. There are things you control, there are things you don't control. Speaking of things we don't control, one of them was interest rates going up five hundred percent in twelve months. If you think about companies, you know, for instance, in the U.S. that started earlier, they didn't have that environment. They had a zero percent interest environment. Very easy, not easy, but it's easier to build. Because you don't have the constraint of interest rates going up very fast and so that was a huge change that happened in 2023. Which is now you have this issue where good companies, really good companies, they are also making the same assessment of like, okay, what are we going to look like twelve months from now, twenty-four months from now? And they're using our products, you know, for the spend and so we had to make really hard decisions on a couple of fronts. One, what are the type of companies that we want? Do we want small companies? Do we want medium? Do we want enterprise? And we had to turn off companies, which is horrible, right? Because they have been using you. They want to work with you and you're kind of saying, hey, you know, just at the spend that we have today, we're not earning enough revenue. We're two hundred people. We're not earning enough revenue for us to be able to service you at the level that we need, but it's not great. So that was one point and then the second one was when we were seeing the interest rates go up, and we had to make a decision to turn off anything that was not thirty day card. So we had a product that was sixty day, ninety day, and we were just like, we're going to turn it off. And that ate a big part of the business but it was the right call. The reason we're here today and growing and have eighty percent gross margins, three billion TPV, et cetera, was because we made that really hard call in 2023. But there was no guarantee. I mean, 2023 was a tough cycle. This was pre-AI, right? So it was just like the cycle of everything's turning off, interest rates are going up, nobody knows what's happening and then again, the market started changing. Now there's more optimism all of a sudden. But 2023 was a tough cycle of like, we went up, turned it down, then reset, and now we're going back up again.

Pablo Srugo (00:52:49) :
By the way, how fast did you get to like a million in ARR and then $10 million in ARR?

Dileep Thazhmon (00:52:54) :
So we did one million in about six months and I think we were doing $7 million a little past a year. But again, this was a different cycle, right? So that then turned off, and they'll be back again, right? It's not a one up and a one down, it's a one and a reset. But again, the thing I would say is what is really good about the 2023 cycle is that there's no shortcut to building a sustainable business. What we had to do in 2023, we would have had to do at some point, which is get your unit economics under control, build a sustainable business, contribution profit has to be great. There's only so many ways to build a business, or you sell the business and you get a good outcome. Which we did in my last company and what 2023 forced you to do is to do that in one year. Which usually you would have two, three, four years to get to that point. It just said you have twelve months, you got to do all these changes and get to that point, or you don't make it and some companies didn't make it.

Pablo Srugo (00:53:46) :
And last question, what will be your number one piece of advice for an early stage founder looking for product market fit?

Dileep Thazhmon (00:53:52) :
Find one metric that you can breathe, eat, live with, and just like a monkey with a hammer. Just go after that metric and don't worry about anything else. Don't worry about whether everything else is upside down, but like, just that one metric. If it's, again, TPV, volume, revenue, CAC, whatever it is, just find that one metric and just beat it down, right? Just completely, completely own it. Because then you also start having confidence and people never talk about this. But even as a founder, you need to believe that the product is working and the only way you can believe is if you feel like that one metric you need to run the company, you're getting the right traction, the right directionality on that and the second part there. Which is also, type this, I think founders should focus on the functions that make sense in the beginning and what I mean is like, you can only do one thing well at one time. So in the beginning, it might be product. It might be just get your product done. Forget about marketing. You're not going to be good. Forget about this, just do product. Then it might be go to market. Now you just are going to be the go to market person. You have to do product led sales, you go to founder led sales, get the ball moving. But then at that point, you might not have enough time to focus on marketing and then as we grew, I'll give you an example. The biggest thing became finance, which is like crazy. You never think about this, but how do you run finance, or we brought in a CFO, et cetera, but you can't do all of them. You have to pick one. You're going to just be all in on that, and then be okay with trading off on the other ones while you just focus on that. And then you juggle, and then you pick the next one, and you juggle, then you pick the next one, and you keep that going.

Pablo Srugo (00:55:24) :
Awesome, man. Well, Dileep, it's been great having you on the show. Thanks for sharing your story.

Dileep Thazhmon (00:55:28) :
Thanks so much, Pablo. I really appreciate it.

Pablo Srugo (00:55:30) :
Wow, what an episode. You're probably in awe. You're in absolute shock. You're like, that helped me so much. So guess what? Now it's your turn to help someone else. Share the episode in the WhatsApp group you have with founders. Share it on that Slack channel. Send it to your founder friends and help them out. Trust me, they will love you for it.