Stableminded · · 48 min

The Stablecoin Card Company That Raised Over $300M in 12 Months

Charles Yoo-Naut, cofounder of Rain, is interviewed by Drew Rogers on the "Stable Minded" podcast (sponsored by Altitude) about Rain's stablecoin-powered card issuing infrastructure. Yoo-Naut states Rain is doing over $3 billion in annualized card transaction volume, recently raised a $250 million Series C led by Iconiq at a roughly $1.95 billion valuation after three funding rounds in twelve months, and grew from 15 employees in early 2024 to around 95. He explains that Rain is a non-bank principal member of Visa that settles with Visa daily in USDC, describes customer segments (stablecoin-first neobanks like Cast and Altitude, remittance partners like Western Union, and global payout platforms), and cites a customer going live in 17 days. The discussion also covers using AI to scale compliance, support, and documentation, and the emerging blurring of card and stablecoin payments in agentic commerce, including Visa's "intelligent commerce" tokens and consent flows for agent-initiated transactions.

Global stablecoin infrastructure and card-issuing platform. Rain provides APIs for stablecoin cards, wallets, on/offramps, rewards, and cross-border payments.

Transcript

53 turns, about 10100 words. Straight from the recording, so it reads like speech.

Charles Yoo-Naut

guest

0:00

It feels surreal. Right now, we're doing over 3,000,000,000 annualized transaction volume. Sending money across borders tends to be really slow. It tends to be very expensive. Stablecoins make some of the expensive pieces very cheap, and you can still use local on and off ramps. So if you're if you're going through a traditional banking partner, it could take you six months a year to even get your first card issued. We had a customer last month go live in seventeen days.

One compliance person that can now be armed with 10 agents that were doing the work of 10 people. There are merchants who are from the cardholder to the merchant. There are stablecoins passing all the way through on on VisaCo.

Drew Rogers

host

0:42

Hey. It's Drew. Quick thank you to Altitude for making this episode possible. Altitude is rebuilding business banking for teams on the frontier. They offer the full stack for the modern CFO and founder, a beautifully designed platform for payouts, bill pay, corporate cards, enterprise controls, and so much more. Move money with speed, yield, and total control all from your stablecoin balance. Operate at Altitude. If your business is on the frontier, your finances should be too. You can learn more at altitude.xyz.

Charles Yoo-Naut

guest

1:10

This is interview take one or interview part one take one. Only one take.

Drew Rogers

host

1:16

Only one take. I only got one shot at this. Well, Charles, we're we've already been talking for about thirty minutes, so it's great to push record. And, yeah, man. It's just great to be hanging out with you and having you here at the house in San Francisco. It's a lot of lot of great energy this week. Yeah. And we're excited for this new chapter of Sable Minded, the show that you guys were so awesome to help us get off the ground last year, and altitude is helping us really take it to another level. So, yeah, man.

You guys have been, you know, stepping out macro and looking at what has happened since we knew you guys. Like, I I remember meeting Farooq at one of the borderless happy hours in New York, like, over a year ago. Must have been way more than you. Right? Yeah. I mean, we were just getting the business off the ground. Stable Studios was the name of it at that time. We cohosted that. We cohost that with Persona, Dragonfly Yeah. Borderless.

I met Farouq, and I was just like it just immediately, my first impression was with Rain was like, oh, this is different. Like, this is gonna this is a really unique approach. And just seeing you guys, Mexico City, the day I think you announced the the Yeah. Was that but that even wasn't the last race. That was a series b. So that was a series b. And then since then, you've series

Charles Yoo-Naut

guest

2:25

Yep. C. Yep. What what was the last race? What's the current update on that? Yeah. We raised our series c, announced it in January, 250,000,000 led by Iconic. So, yeah, from series b was I think we announced it October. When were we make? And then that so that puts you guys around 2,000,000,000.

Drew Rogers

host

2:41

Is that right? Yeah. 1,950,000,000 valuation. What does that feel like?

Charles Yoo-Naut

guest

2:47

It feels surreal. Yeah. Just going from raising our series a we announced series a a little bit more than a year ago. We announced it February 2025. I mean, that felt like a really big, big moment and just great momentum. And then doing three rounds in twelve months, that was just not not really expected on our part. So very grateful. Definitely still feels surreal and just trying to keep up with with everything.

What for those who are just getting to know you guys is that sort of secret magic powder that's been sprinkled on rain? Yeah. Mean, I you guys have I was looking at your career page recently. Like, you're hiring a ton. Yep. Your go to market presence is increasing.

Drew Rogers

host

3:23

You're growing globally. The use I mean, you know, I'll just say it for myself. Like, you guys are dominating. Like, you are Yeah. You are clearly in full position in this category. What was that magic powder for people that are just getting to know you to get you and and why is that valuation warranted

Charles Yoo-Naut

guest

3:38

given in the the category you're in? Yeah. There's nothing really secret or magic. It just we were in the right place at the right time. We've been. Farooq and I met five years ago through the on deck fellowship. Started RAIN towards the end of twenty twenty one and just really had a few moments where we built deep conviction in stablecoins and then also built conviction that making them spendable through cards was, like, the best way to start making Stablecoins actually globally accepted and adopted.

And so we started a long time, and and some of the stuff that we built just takes time to do. So we were able to start four years ago and and have that four year head start to be where we are. And really just the progress the last twelve months and and the fundraisers, that's just more of a reflection of how much the business has done.

Like, we've had a lot of the foundation longer ago, but it didn't it really took us getting the cards into people's hands at scale and powering all these different programs for people to really appreciate what we had built. Because before, like, we can talk about, oh, we're principal members of Visa. We've built all this on chain settlement, but I I think it didn't really click in people's minds until they saw the use cases and they saw all the things that our partners were doing. And then it's like, oh, wait.

That's cool. That makes sense. That, okay, all the stuff that you did actually led up to this happening.

Drew Rogers

host

4:50

It's funny that yeah. It's about, like, what are the use cases? I think I I asked for, you know, he was on, I think, with the season we were doing. He and Kai Sheffield were talking, and I was like, what are the use cases? And he's like, well, what are the use cases for for money? Exactly. We see it we see it all. It's really cool to think about what you That was like that was kinda frustrating to me when we were building in 2022, 2023,

Charles Yoo-Naut

guest

5:14

and people were trying to figure out use cases for crypto. And I'm like, it's right in front of everyone's face. We're like, just moving money is so broken in the traditional fintech world. Like blockchain, crypto, stablecoins, we've already built something that's way better than is available. Yeah. And people are just overcomplicating it almost. It's like, hey. This is already

Drew Rogers

host

5:31

a killer feature. We just need to get into people's hands. And I think a lot of people didn't really appreciate that until you look at the charts and see stablecoin adoption exploding. Yeah. So as we kick off sort of the framing of RAIN, we've talked about the valuation. We've talked about a little bit of the timeline of the business. What can you share around, like, just the the analytics side of this? Like Yeah.

What what is something what is the public, like, bullet points or things that can help people, like, wrap their minds around? Where is rain? How much is it what volume what do volumes look like? What can you share around those things? Yeah. So right now, we're doing over 3,000,000,000 annualized transaction volume in cards. So that is like percent. The amount of swipes

Charles Yoo-Naut

guest

6:17

plus the value of those cards or those transactions Exactly. On a annual basis. So three you said 3,000,000,000 worth of Payments. All around the world. All around the world. So we work everywhere that that Visa's accepted. So you can swipe a card wherever a Visa card is accepted, and we see transactions being used all around the world.

Drew Rogers

host

6:36

When we were just at the coffee shop, that Yeah. Goo cash card Yeah. You guys yeah. So when we were at that coffee shop, what technically just happened? Like, walk us through that high level experience. So

Charles Yoo-Naut

guest

6:48

I I use my my Cast card, the new pengo the new fuzzy penguin one that is very cute. So that's that's powered by by Cast. They're they're one of our partners. So I have a balance on on my Cast app. I've I've loaded Sablecoins, that's given me some credit limit. I have the relationship with the payer. So, like Yeah. They no one knows typically. I mean, you're an anomaly with this experience, but no one would know. And the average CAS user doesn't know about RAIN. Exactly.

They they their relationship with this CAS, they their affinity and their their brand the brand they associate the card with is CAS. Yep. I've gone I went through the KYC process on that. I set up the card. I sent my stablecoins, and that that is what created the credit limit on the card. And when we tapped it, we get the message from Visa and then send that to Cast, and then Cast will make a decision whether they wanna approve or accept the based on, you know, they might have different rules.

We have our own rules, and we get that acceptance from them, and then we pass it on, hey, this transaction is approved. But no money actually changes hands at that point. The way that we were built on the credit rails, you know, settlement with the merchant watch up in multiple days later, but all of our settlement with Visa happens in in stablecoins. So we're settling with Visa seven days a week in USDC, whether it's a holiday, whether it's a Saturday, Sunday.

We're paying for that day's volume that has settled on the Visa rails. And then Visa will then pay the merchant in their whatever their settlement currency is. So all of Visa's settlement is net settlement. So if you're a merchant in Mexico, for example, you will not you won't get paid for each individual transaction. You will get paid by Visa as a net of all of the transactions that you did. And the same for us as an issuer, we settle with Visa net of all of the transactions that we have done.

And then the flow of funds that I was surprised to learn recently was, like, you guys are actually in the more, like, earlier part of the flow of funds Yeah. First.

Drew Rogers

host

8:42

Walk us through that. So you guys receive the funds, and then who who are you guys actually in between? I don't know why in my brain, but like being first seems more Yeah. Powerful or more influential. I don't know if you agree with that, but the fact that you guys are actually

Charles Yoo-Naut

guest

8:58

the order of operations where you sit seems really strategic. Like, walk through that a little bit. Yeah. So we're the customers are are paying us back for whatever transactions that settled in the Visa network. And then we've already we've settled with Visa for for for those transactions. So the funds will go. We'll we'll settle with Visa for those funds and USTC on a daily basis. So, yeah, we're we're pretty early in the kind of repayment of the transactions flow. What is

Drew Rogers

host

9:26

cards have been, I think, a very obvious adoption accelerant. Yeah. What do people the vantage point you have of seeing the data just gets me really excited. I think you you have such a unique ability to I remember when I walked into Square's office one time, I when I think I was interviewing there or something, in their lobby, they had a huge it was like six TVs that showed just The US, and the payment volume visualized the data was visualized on like heat maps. Like the current I don't know.

I I guess it was just the Square network of like people in Like Square terminals. Yeah, like the payment volume heat map. And I just, it was real time. It looked like a radar, like something you'd see in like a Jain Yeah, we actually have our own, we call it radar, so it's We call it radar. Yeah, have a globe because we're more global. What are you what are you seeing? Like,

Charles Yoo-Naut

guest

10:12

is the radar? We just see pings across the globe. So we have a the way the radar works, it will go from the cardholder's address to, like, the merchant's, like, location. Built those visuals. Yeah. Yeah. Just internal. So cool. We built it internally so we can just look. And we did it for Black Friday just to see like all the volume that was happening.

So it'll go you just see like this line go from where the cardholder is to where the merchant is and just and also the globe will rotate to to show different pieces of Would you ever expose like, or We're we're thinking about it. We I mean, we need to do it in a way that protects the privacy of the the card holder, so I don't think we would show where the card holder is. And then internally, we also show, like, the magnitude. So if it's a larger transaction, that line is actually a lot bigger. Mhmm.

So I think we would do it in a way that would protect, like, privacy. We we would consider That could be really interesting. Exposing something during Black Friday or or, like, some other critical event. Yeah. Because Black Friday is a very US centric holiday, and our our customers are more and more global. Maybe The data nerds would love it. Yeah.

I don't know how much normal people would care, but the industry I mean, for people but then again, like, you're you're selling to people who are, like, probably in that position. Yeah. It would be a great like, our customers are not really the end card over. Yeah. The marketing that we do and the go to market motions events we have is more catered to people that will be buying our infrastructure

Drew Rogers

host

11:31

that wanna issue cars through Reign. So, yeah, I think those people would would appreciate it. Yeah. Tell me about these people. So right now, you guys are talking with Nick and team or Mhmm. Probably talking to all these different businesses.

Charles Yoo-Naut

guest

11:41

What are they what do they value most about Rain right now that you've come to find as, like, the true like, what are they what are they mainly using you guys for, and what is something that's, like, maybe surprised you that they really value that you guys are doing? Yeah. Our core product is still card issuing. We're expanding to offer the full stack that you really need to to launch a financial product and working with a a bunch of different partners to do that.

But the way I boil it down is really any financial product can be delivered faster, cheaper, and in more markets using Stablecoin Rails. And then that's what we're basically selling to our customers. Like customers are fundamentally coming to us because we can do something cheaper, faster, and more markets than anyone else because we're built on stablecoin rails, because of the infrastructure that we've we've developed. And on those three axes, like, it's really hard to compete if you can nail those three. What

Drew Rogers

host

12:34

are the different flavors of customers? Because I'm imagining Cast over here, they are building and there are many different, like, neobanks and and Yeah. Financial user applications who are at that, like, I am using this thing because I want a card. Yeah. Like, I know that versus maybe some of these other go to markets that are almost like bringing RAIN to market themselves. Like, what what are those core differences?

I'd imagine the function that RAIN can or even like, I'm even thinking about how RAIN could service a financial operations company. Yep. You know, you see Bramp, Brex, and like that that whole category of companies.

Charles Yoo-Naut

guest

13:08

How do you bucket these in your Well, we think about our TAM. That's the idea like, we started in the corporate card space for crypto native teams. Yeah. So very niche, like alright. The the quick pitch was this is ramp for DAOs. So that was like a very niche niche TAM, niche market, but I think it's important to start in something very small and just like nail that experience and and solve a hair on fire problem even if it's for a really small set of customers.

Now when we think about TAM, it's like every financial product could eventually be built on rain rails. So it's gone from that very small, very core group to, like, okay. This is, a huge universe. And what we're seeing, a few buckets where we feel like we've seen a lot of adoption and excitement. One is just this whole new wave of of new neobanks that are deciding to go Stablecoin first.

They're just skipping traditional bank partners, and they're trying to launch a product in multiple markets, serving a global customer base. And they're choosing stablecoins to do that because that's the best way to build that type of product. So that's like a whole class of companies and and use cases that we're we're really excited about. Altitude is use case. Right? So people like EtherFi,

Drew Rogers

host

14:20

like Yep.

Charles Yoo-Naut

guest

14:22

And then I think within that, you can kinda subdomain it or you can consider them different use cases, but something like a Remin's app. So we announced our Western Union partnership. Yeah. That's huge. So what like, Remin's is a great use case for for stablecoins. Just fit that use case very well. You're sending money across borders. It tends to be really slow. It tends to be very expensive.

Doing creating this stablecoin sandwich where stablecoins make some of the expensive pieces very cheap and you can still use local on and off ramps for folks, and they don't even have to know what's happening in between.

Drew Rogers

host

14:53

That's been like That seems different though in some ways. Like, you have you have these sort of altitudes and casts of the world. These are like new on chain native companies Yeah. That probably we we talked with the Moto team, for example, like Moto was like, yeah, we like literally started our company because Rain existed. Yeah. And we knew how what they did and like, we were able to like build a business on that.

These are like these really innovative set of new companies that are building from first principles knowing RAIN exists. Then you have this like other one which is western the more of the western union use case where it's like, these companies have existed for centuries, some of them, and they already have customer relationships and I see them kind of using Rain as let's just add this almost as like a backward checkout option where you have we're just adding another option. Yeah.

And this option we believe is superior, but like in their minds, they don't have to like get a new customer, need to onboard something new, they're just saying, hey, let's add this functionality to the existing. Oh, exactly. But there you're also seeing though now upstarts going after the Western Union.

Charles Yoo-Naut

guest

15:59

Those two groups can compete and you're gonna you're gonna win in both places as they do. Like what Minh says like that's that's been an exciting use case to look at. Well the area that we're we're like, getting really excited about is, like, global platforms. So whether you're an Airbnb or an Uber, you're paying people out globally. You have to figure out those local payment rails in in all those different markets, and that's a cost center for you.

If you can actually give people wallets, pay them out in stablecoins real time or or There's like real new the new vase for you guys. Right? Like, of a new vase style Yeah. Yeah. Yeah. Similar to, like, hey. How do you turn global payments, global payouts from a cost center to actually revenue center? You're able to the money inside of your ecosystem for longer, and you're able to monetize the spending of that and build build more brand affinity as well.

Like, people are happy because they're getting paid faster, and they're able to use that money for expenses a lot quicker. They don't have to wait for their payment to come. Like, f Uber driver can get paid right after the drive finishes. They can get paid streaming while the drive happens if you wanted to. Right? Like, you're not constrained by the the rails anymore. You can kind of imagine much new payment experiences. Those are ones that are I mean, it it takes more convincing, more education.

It's not as obvious, but that we're very excited about. Yeah. So those are are a little bit of flavor, but really, the the world is so wide for for potential use cases, for potential customers. And we're we're also starting to see AgenTic

Drew Rogers

host

17:26

payment use cases come up, which is a whole You said the word. Yeah. Know. Said it. We opened the can. AgenTake payments is is really exciting as well. Yeah. And that's like still early days. Think people are not sure how it's gonna play out, but it's it's it's happening already. Like agents are making transactions for for humans, and I think that's just gonna continue to grow. Mhmm. So we're figuring out how can we support those use cases as as much as possible. It's so cool. It seems like alright.

So let's we'll open the we'll open the agentic can here and and and but just closing closing this last loop. Yeah. So I feel like the and we talked about this and maybe just to peel this back one second. You have so many different parties even as we're talking.

I'm thinking I think this way just maybe because we're we're psycho and we talk to everyone in this category, but I'm thinking about the the last podcast season that we came out with before this was with Braille and, you know, we've talked to Coin when Oh, great. We have we have like that team in mind and you have the Arculus team. It's like there are all these different pieces of this puzzle and what you were saying that to make the and Ray Rayne is touching all of them, like, swipe the card. Yeah.

Those are all our partners. Mean, it's like cool. Yeah. Because everyone's playing a different role. Like, if that fintech wants to issue the stable coin with Braille or, you know, get the rails built with Coinflow and settlement built with them. Like, guys are just Like, Complosacres and investment rain, we we issue a bunch of Complosacres cards. Yeah. It's like a big happy family. It's great. And you were saying how you guys are often in the position where companies will come to you, and they'll be like, hey.

We wanna do this. And that probably requires a lot of those friends. And how are you thinking about this like, you know, the default partners or the kind of the recipes that you just you don't wanna put people in the position to say, hey, you can use us for this, but like Yeah. Go call Tom from Arculus and him from Coinflow. And like, you don't wanna force people to do that. How are you making

Charles Yoo-Naut

guest

19:15

how are you delivering kind of completed stacks to customers right now? We try to be as agnostic as possible. So if someone comes with us with a preferred partner, we we will make that work, and our stack is pretty modular. You can pull out any piece that you want. But more and more people are coming to us with not an opinionated view. They're just interested in in Stablecoins and what Stablecoins can enable for their business. So then we're guiding that discussion, and we have a great group of friends.

And every big big customer is almost like pulling together the Avengers for like, okay, who is I know the perfect partner for what they're trying to do. What are the key buckets that they're like what are customers knowing they need? I'm sure there's like a handful of things they're not typically thinking about, like, go talk to that like sanctions and compliance. But like, what are the what are the key buckets that you actually think there's go to market demand, people need this, categorically,

Drew Rogers

host

20:08

like, what do those look like in your mind right now? Yeah. Can vary depending on what the actual product that the customer's trying to deliver is. But typically, there's, like, virtual accounts on and off ramping. There's wallets.

Charles Yoo-Naut

guest

20:20

Like, interop with banking and, like Yeah. Name Interop with, like, existing financial rails. Like, you wanna be able to go in from ACH or Swift, and you wanna be able to go out into a bank account. You wanna be able to store those in, like, a wallet somewhere. You you might want a MPC wallet or you might want a a noncustodial, like, fully noncustodial, like, some smart account. So it just depends on what the use cases are. Like, we would recommend a different set of partners.

We try to integrate deeply into these partners as well to make that process as seamless as possible. If you want cards, you know, you might want a fancy metal card. You might want a a metal card with a hardware wallet attached to it. So, like, okay, we we work closely with ArcLis and we can deliver that for you. You might need I wanna issue your own token, and we have partners that can help you issue your own token.

If you're if you're I'm very opinionated on reserve management or yield, then that might dictate which partner we would recommend. So, yeah, that that's becoming more of the roles, like, kind of Yeah. You have to consult, really. Yeah. Like, it's becoming a consultative approach, especially for larger deals, more enterprise use cases. Have you thought going and so, like, as we pivot into, like, the agent side, it's really interesting. Well, okay.

What are the things that they're not thinking about that they that that is typically needed, but, like, isn't often prioritized on the front end? Anything come to mind? Well, those things we try to take care of for as much as possible. Handle as much of that as you can? We try to handle as much as possible, abstract away those decision points.

Because when we think about just time to go live and scaling a program from our first conversation with a customer to, like, when they're going live and growing, like, how do we reduce that as much as possible? If you're if you're going through a traditional banking partner approach, so it could take you six months, a year to even get your first card issued. We had a customer last month go live in seventeen days. Just call like our first email. From like signing up.

From signing the contracts to issuing their first card. So we're always looking at, okay, how can we bring that down? What are the areas? And like, how do we make integration simpler? How do we improve our docs? Like, where can we inject AI to automate things so you don't have to talk to a human if you don't need to? Like, how do we make the contracting process simple? How do we simplify our our pricing tiers? What's been the biggest unlock to accelerate that down seventeen days recently?

Like, what what have been Yeah. This one? There's there's a few things. Like, now for larger deals, like we have we've grown our team. Like we were only 15 people last year in February. That's crazy. So we just didn't have like the manpower Yeah. Really have like people managing the account properly. So now we have that. That's like a very basic thing. We've really worked on our our docs. So improving the documentation, improving, sample code. We're we're rolling out SDKs now to make that that even faster.

So improving the documentation has been a big thing and then injecting AI into the documentation as well. So a lot of questions that we would get asked. We spin up a Slack channel for each of our customers. So questions that would go into the Slack channel now getting asked in the docs itself. And then we're able to see what questions people are asking and then use that data to improve the docs. Like, okay. People don't understand the flow funds or they don't understand how to decrypt a pan.

We should, like, make that clearer. We should provide more sample code. Is the the user experience so I'm in the API docs. Yeah. Is that like a chat bot or, like, a text? And is it something that they're typing Yeah. Or speaking eventually? Like, what does that look? Right now, it's a chatbot inside the documentation. So we use Mittlify, they're great Mittlify is the name? Mittlify? Mittlify. Yeah. They're like a docs infrastructure provider. Really interesting. Shout out to Mittlify. Yeah.

Mittlify has been been great. They're also crushing it. Every docs page I go to now is powered by them. Sounds like it's not like a crypto business. No. It's just like a, you know, everyone's using them for APIs Yeah. Docs. Yeah. They do have even coast? Yeah. We use coast as well. That's been a good unlock as well in the sales process. Shout out coast. We like that. Yeah. Coast demo. We set up post demos for for customers, and they can, like, see how their app would, you know, integrate with the RAIN APIs.

So that's that's a lot. We're we're working with another company to help with they're called Stainless. So helping generate different SDKs, different languages for our customers. So server side SDKs in Python or NodeJS or in Ruby. Because a lot of times you can just read the API spec, and it's pretty straightforward how to build the code that will interface with the API. So that's, like, perfect use case for an AI to just generate those those SDKs.

So, yeah, a lot of AI that we're trying to inject to scale the onboarding implementation process, take humans out of the loop, and then put the humans that we do have in the places that actually matter where they're more of a consultant on how they should be designing their program, how they can grow their program. And that's, like, where we wanna be injecting humans. It's like that more of that consulting. And then the answering questions, debugging things, how can we push that to to AI as much as possible? Yep.

So let's open the aperture of Agenza Commerce AI, like humans. Like, okay. So we

Drew Rogers

host

25:11

this is really key. And I think you guys, even the way that you're talking about the docs and, like, serving the developer community, I believe will be, like, eventually, you that's not gonna be a person asking those questions. Yep. Agents will be evaluating these different things, and making the best decisions, and doing that work. At least what I'm learning is starting to happen. Yeah.

It's like, my gosh, like, I can just go deploy an agent to build me a program or go research options, and that's gonna all happen within those docs. And how you you're sort of getting into it, but like where do you see, we can talk about like the use cases for Agenza Commerce a little bit, but more so on your side as a founder, as a leader of people. Where are you seeing the most valuable use for where the human, like, the human touch matters? Yes.

But what does that look like versus maybe what you think is gonna start to I think everyone's freaking out about Block right now and what happened on x Block and like Oh, yeah. That was hard to see, but there's probably more to the story there too. But what does that look like and how you guys are thinking about hiring and human? Yeah. It's I think we're in a pretty

Charles Yoo-Naut

guest

26:17

exciting position being a founder in the fintech space at the age where AI is really starting to bloom and grow and there's every month, there's, like, a new huge unlock. Like, I I would actually I don't know if I could be an AI founder right now because the space is moving so fast. Like, you're getting competed left and right, and people are raising $100,000,000,000 rounds every every other month.

I think it's really hard to actually be an an AI founder, but being a fintech founder is great because I'm able to utilize all these AI tools and they're they're bringing down the cost of running my business. And I think fintech has a little bit more of a moat against AI than if I was just building like a SaaS product that could be completely vibe coded. So there's a lot of benefits that we're able to utilize, and we're being very thoughtful in hiring.

Like, we don't wanna get into the block situation where they grew to, like, 8,000 or 10,000 people and they had pick up that. It was a lot of people. I think it was partially they overhired. AI is a good way to probably cover up for some of that overhiring. And then I think that's probably was part of the the firing was just they hired too many people. Think I there was definitely significant efficiencies they got from AI that they were starting to realize or they just projected.

So we're really trying to get ahead of that. Like, we know that AI is coming. We were only 15 people a year ago. We're, like, 95 people now. How do we prevent that overhiring? Thinking through, like, every new hire that we have, what is their role gonna be like in twelve months or twenty four months with the assumption that AI will continue to expand, the capabilities will continue to increase. So we're really, really thoughtful on how we're growing the team. Typically, with with fintech, it's very compliance heavy.

It's very support heavy. Those functions tend to have to grow linearly with the number of customers you have, number of transactions you're doing. I think with AI, starting to see it become more logarithmic. You you're starting to see it, like, asymptote at a certain point where you don't have to hire one compliance person for every thousand new users or 10,000 new users. Because one compliance person that can now be armed with 10 agents that were doing the work of 10 people.

So we're we're we're trying to invest a lot in AI for compliance, AI for support. And it actually is is we feel like making support and compliance better at scale because a lot of compliance was compliance theater where you actually couldn't look at every suspicious transaction in a meaningful way and do really deep investigation.

Now we're able to have looser rules that can catch a lot of things, have AI agents do a first pass at those suspicious transactions, and have humans go deeper into the ones that actually make it past that first filter. So that's, like, where we're we're trying to grow, like, compliance and then support as well. There's a whole class of questions that come up from support that are in the docs or they were explained somewhere else and then just people don't know where to find it. That can be easily handled by by AI.

And if you provide it the right contacts, then have the right data available for it. And then that leaves a support team available for for handling real issues. Maybe there's a bug or maybe there's something that requires, like, a consulting approach.

Drew Rogers

host

29:20

Yeah. Partner makes sense here based on what I value? Or Exactly. Is that what you're finding is, like, something I'm always thinking about like the go to market landscape or like the more of the people, the business people, right? Like the people who are Yeah. Doing deals and like Yeah. Making introductions and have networks and whatever we whatever we call those people now. Yeah. Partnerships, like the what what are your what's your take on that side of the business?

So you guys have been hiring a lot of those kind of roles lately. What's the what's has how has that side of the house changed in your mind in the last three, five years? From AI? From just like the way that deals get done, the way that I mean, you you've you've worked in like software fintech for a long time. I mean, there was this like era where like you had to hire like Yeah. A whole army of AEs to like go, you know, use HubSpot and all the tools to like just completely mass blast and that was how you did it.

How have how do you see the world of, yeah, like the enterprise commercial function changing? Like how many people do you need? Yeah. We've we've tried to build that team very differently. I don't know if we'll continue to build it that way going forward, but we don't really have the the typical, like, AE model. We don't have any quotas.

Charles Yoo-Naut

guest

30:28

You just keep paying Nick more. Yeah. It's really just Nick. Nick is the number one in the BT team, and he has 20 agents, and they're they have different names, you know, but It's all it is. No. It's it's still a pretty lean team. Almost everyone I think the title is BD in partnerships. We don't have anyone that that has a really different title in that org, and that is a reflection of it. It is very much around developing these relationships, creating these partnerships.

And I think that's where the role is moving towards. It's not just having people call cold call a bunch of people trying to sell software. I think we've done a good job of building relationships, having close partnerships. And then what we're using AI for is, like, we're getting a lot of inbound. How do we filter the inbound? How do we move people along the process and then inject people when we need to?

But at least for, like, smaller deals, startups, we're trying to make that as self serve as possible while having the right guardrails in place to make sure that it's the kind of partner that we wanna work with. Yeah. Okay. And then the humans can focus on the larger deals, the more complicated deals, the ones that will require education or consulting. Yep. So we're we're growing the team more in that in that realm.

Drew Rogers

host

31:32

Yeah. You guys have done a really good job of just showing up in person, hosting events. Like, Rain has always seemed very embedded within, like, the builder community and so okay. So we've talked about the role of more of, like, the AI workflow update within more just like business and leadership. How do you now, speaking specifically to the world of commerce and transactions, and I think you guys are in an interesting position with both of this like human side of the swipe.

Like, the humans are very needed in the the point of sale experience or whatever. How do you see those two opportunities for RAIN? Like, because you kind of sit, I'd imagine, in both where you have, like, the b two b side. Yeah. How do you think about the the buckets of opportunity for both, like, human centered commerce and agent to commerce right now? Yeah. It's it's a very exciting

Charles Yoo-Naut

guest

32:24

time to be in this space or also, we're at the intersection of of cards and stablecoins, and I feel like those are coming to add with agentic commerce where people are debating what the future is. Like, are agents gonna use stablecoins, or are they gonna use cards? But we we even say cards and, like, cards can be physical. Yeah. They don't always have to be. Yeah. And the way we think about cards, like cards are really just mechanism for initiating a message. Right?

It's something you're tapping something and that is sending them. Like Visa is the message network, and it's going a message from the merchant to the eventual cardholder, that there's some sort of value that's gonna be transacted. And that doesn't have to be a like, it doesn't have to be a physical card. Right? We see it can be a token On a on Apple Pay, it can be a token that an agent controls.

And then what happens on the settlement layer, like, we're already showing with our work with Visa, it doesn't have to be Fiat. The settlement for that message and that value transfer can be stablecoins. So I I I do think that the distinction between cards and stablecoins is not as big as people are making it seem. And then the the actual divide between a stablecoin payment and a card payment is gonna start blurring.

There's gonna be like, what is like we're already doing stablecoin payments on cards, so what really is a stablecoin payment? I think that that is gonna start blurring and then you're just gonna have value being transactioned on a network. Interesting. Because right now it seemed they they do seem fairly separate in terms of how people think about them. Visa already has merchants that are getting stable settled in stablecoins, and we're an issuer of settling in stablecoins.

So there are certain merchants where from the cardholder

Drew Rogers

host

34:00

to the merchant, there are stablecoins passing all the way through already, and it's happening on on Visa rails. So that looks very much like a wallet to wallet transfer. There's a lot of hops in between to get it, but I think we're on the path to So that would almost be in your then this is for me what I get probably most excited about as like a payments payments minded, like I started at Square.

So I've always I've always thought about like these full end to end, I think I've said this maybe to you before, but the first ever memory I have at Square is them like shepherding us into this boardroom and spending like hours looking at all the hops Yeah. Of like a payment transaction on a big whiteboard. Yeah. And it was like seven or eight different like big hops that money takes.

And it's like, think I Square had like a, you know, we're gonna take this nine hop and we're gonna own these four and like that's great. But like to actually be able to use stablecoins on both sides is something still that we're not even we're just now getting there. But what you just said is sort of like, hey, we're starting to see the merchant side Yeah. Natively have wallets or natively be able to take it.

Is that essentially, what you're saying is happening is like, you guys, Visa, and then, you know, let's just say it's like the shift four layer or the Yeah. The new way. Like, the new layer, and then you're starting to see more of that. Like, it's just negative. Yeah.

Charles Yoo-Naut

guest

35:14

And then what we've done is compress, like, the traditional issuing stock already. So, traditionally, you you have your bank partner. You have, like, your your program manager. You might have a reseller, and then you actually have an app, and then you have the cardholder. So, like, those are all those hops, and we've merged together. Okay. There's no reseller. There's no program manager. There's no bank. It's just RAIN. So already, like, those three hops is Can you say those those again?

Like, the the BIN sponsor, which is usually a bank in in many cases, you have, like, the program manager that's that's on top of that BIN. So, like, in the fintech world, you got

Drew Rogers

host

35:46

you You guys have that yourself. You guys have a BIN sponsorship. Is that true? We are a principal member of Visa. So the It comes with that?

Charles Yoo-Naut

guest

35:54

So the BINs that that are our cards are there there are BINs. Like, we're the the license holder on the Visa side. Cool. Yeah. So we're a non bank principal member. Amazing. And so that kind of checks a lot of those So it it condenses already, like, those nine hops. Like, we've condensed three of those into one and made it a lot more efficient, and that was possible because of our unique setup and and the stablecoins that that really enabled that to happen. Yeah. But, yeah, we're excited.

We're already seeing agents already making transactions. The easiest way right now for an agent to make a transaction is to use the existing rails. So giving your agent your existing card and then having them go enter it in into a HTML form on a website to pay for something for you. That's happening already. And now it's like, okay. How do you improve that process? Like, how do you make it safer? Like, I don't wanna just give my agent the secret numbers on my card.

I wanna give them a token, and Visa's doing that with their intelligent commerce. And now now my agent has a has a token, and how do I make sure that it's getting my consent to use that token? So what is the consent mechanism for authorizing an agent transaction so it doesn't go off the rails and starts blowing out my credit limit? And so that's Is is that typically like a biometric signature right now, something like that? It could be usually, it's like a SMS or an email.

So you've probably seen, like, the three d s like, three d secure flow where you're you're and it it's it's not as popular in The US, but some maybe you bought a ticket on, like, Delta, and you'll see, like, this pop up of, like, hey. Like, type in this code from your phone to make sure that this is your transaction happening. So that that's like a three d secure flow. We'll probably see that, like, for agents where you might give an agent a limit.

And if it goes above that limit, it might trigger some sort of consent flow. Maybe it could be biometrics as well for more advanced flows. So I think that's, like, an important piece that's that's being built. There are also, like, agent commerce might start becoming a thing where maybe they choose to to interact directly in stablecoins where they have a wallet and they're just sending each other Stablecoins directly with without using Visa network, that is, like, a potential

Drew Rogers

host

37:58

maybe more merchants are gonna use some of these new standards, like x four zero two or something to accept Stablecoin payments or accept agentic payments. What's the current way? So like right now, what I'm I'm gonna leave this San Francisco couple days, and I feel super convicted. It's like Yeah. It's time to really not just for like a learning experience, but for our business, like as a media company.

And we're Zach and I were just talking about, hey, we need to hire, like, a social media person to, like, review these things and clip these things and, you know, draft all this content for all these different platforms. And, like I think all this so like, think we could build a social media agent to go do that. We're like, yeah, I'm starting to think this way. What what is the today best way for me? Where do I go after we stop talking? Yeah.

What for a what I'd love to have is to go create an agent for certain purpose and then equip them with a RAIN powered card that I can just go, you know, I'll throw some USDC Yeah. Into that. What's

Charles Yoo-Naut

guest

38:58

like the lowest, simplest starting point to do that? We have some customers that are are enabling this that I can I can send your way? We're we're gonna make it simpler. But we're early still. We're still early. I think you're starting to hear more announcements of people where, like, the agent can just spin up a rain card for a single purchase, and then that card gets deactivated once that per purchase is made, so additional protections.

Drew Rogers

host

39:22

So what was the partner you guys had announced on this? It was it was, like, a couple months ago,

Charles Yoo-Naut

guest

39:26

and they they had that specific tech, and it was like There's one called Clutch that doesn't use yeah. I I wasn't sure if last time you were It was

Drew Rogers

host

39:35

It was like a per transaction or kind of like a build your it was a company that allowed people to That's that's part of architect their own, wasn't them? Yeah. It's not necessarily for agents, but I think that's, like, the natural evolution

Charles Yoo-Naut

guest

39:47

of it. And we're gonna see more, and and we're we're trying to make it easier for our customers customers to to build these types of experiences and getting input from them of of what they would like. Like, what do they need? What protections do they want? What what would make the integration easier? What would make the experience better? Yeah.

I'm gonna ask you a really hard compliance question, and I'm not gonna, like, don't it's not advice or anything legal, but like coming from someone who thinks about payments from a compliance standpoint Yeah. I remember there was a lot of this when we were dealing with like NFT purchases and it's like KYC

Drew Rogers

host

40:19

Yeah. And Levels and this NFT is under this threshold so we don't have to like get their driver's license. Like, there's so much there in that category. What are you when you think about agents, I'd imagine almost like some of these thresholds, there's probably a ton of compliance related permissioning. What are you are you seeing anything in this? Am I thinking about that right? Or who's I think there's different ways.

There there's starting to become this concept of like know your agent and what does that mean and because agents can like, if I provision an agent Yeah. And it's going to like do illegal commerce on my behalf, like, I'm going to You're you're on the hook. I'm on the hook. Like, so I mean, that seems like a really interesting

Charles Yoo-Naut

guest

40:57

Yeah. We like, for us, for example, we don't allow the team to use Cloudbot and some of those because we feel like the the controls are not there in place yet for it to just not completely wreck you. It'll get there, and over time, there'll be more enterprise grade tools and enterprise grade controls. And I think the same thing with compliance.

Like, right now, the way we we're we're treating agents is, like, we're still gonna KYC whoever's requesting the card, and they're still on the hook for any transactions that you just can't say, hey. This agent is acting on its own. We're not gonna give an agent a card and trust that. So agents will always be associated as an extension of a Yeah. Human being who will be, at least right now in RAIN's definition, or, like, how I probably now, unless there's new guidance Yeah.

Or new laws that are in place around agents, think that will you know, well, same thing with autonomous vehicles. Right? If you if you go into a Waymo and it hits someone, okay, is the Waymo responsible? Is that car responsible? I think there's The person is in the back. Yeah. It's like so where does this responsibility live in, like, a more autonomous world where there's, like, algorithms and explainability of some of these algorithms is not not great yet? I think, though, that's, like, still not It's messy.

So we have to go back to, like, what are the existing rules and frameworks in place. So we'll pay attention closely as those progress and start thinking about where we think the puck is is gonna skate on some of those issues and try to get ahead of them, but it's still early days. Yeah.

Drew Rogers

host

42:22

I can imagine microtransactions generally from what I understand about agents, simple coins. We talked with Lewis from Circuit and Chisel yesterday about this of, like, micropayments specifically compared to, like, a 2.9 plus 30 per 30¢ transaction. Too expensive for a There are very clear use cases where stablecoins are superior for agents to use, and they will, and it's always on, all all the things. And just that that unlock there, it's pretty powerful if you think about it.

And if it's micro, from my this is my own personal view is like, if it's if it stays pretty micro, and especially if RAIN is able to provision cards like you're saying, which I didn't know on a per transaction basis, my understanding of the kind of compliance law has to do with ticket size. So if like the tickets are tickets meaning transactions are of a certain size, certain states or or parts of wherever you are in the world will require certain different levels of diligence.

But if it's micro and that's like a part of where stablecoins are used, it could be a really interesting not loophole, but just like it won't be as big of a deal. Yeah. Because stablecoins from my understanding right now are are way less compared to, like the bigger the ticket goes and that settlement can be I don't know. Maybe maybe not. Maybe I'm thinking of it wrong. But microtransactions

Charles Yoo-Naut

guest

43:38

seem to be a nice I think that's a clear they've been talked about for a while. Yeah. I think we still haven't seen the use cases for microtransactions that will get, like widespread adoption, whether it's like tipping a content creator or paying for a singular article, at least the infrastructure won't be the barrier anymore. Yeah. It's just gonna be like That's Dude, it's like we're actually not even seeing that yet. Yeah. Like I I go to I hit Bloomberg and they're like, pay us $2. Yeah. Yeah.

Maybe I'll pay 10¢ to read this article. Yeah. But I don't wanna like I don't wanna know like, I I'd rather just like something like that kind of exists and I can just face ID in and you know. I think right now there's just a lot of friction in payments. That's probably where agents are gonna help a lot. Like, every time I go to a new site, I need to go type in my address again.

Like, okay, my billing address is different than my shipping address and, like, what card am I wanna use based on what kind of site this is? Maybe I wanna optimize points or something like that. That is, like, mental load that you have to do on every transaction that you might just not do that transaction because that mental load is so high versus, okay, my agent's gonna do this for me anyway. Just, like, I press a button and then I have access to this content or I bought this new shirt or paid for something.

One of the things that I absolutely love about this is like, we're not going anywhere. Like, I don't think you guys are going anywhere either, and it's just gonna be fun to hopefully get the opportunity to just continue to follow you guys Yeah. And see what happens. Yeah. If you love if you love tech, if you love, like, innovation, like, it's just such an exciting time to be alive. Yeah. Think there's a period where where tech started to get boring a little bit. When was this in your mind?

I I think it was, for me, '20, like, mid twenty teens, like, '15 to '20. Time? I was in the Bay Area. So I I moved to New York 2021, like, a month before COVID happened. I signed my lease and then, like, yeah, I didn't get a COVID deal. It was it was bad. But before then, I was in the Bay Area. We're in the West Coast since 2008. I was in the West Coast for, like, eleven years. And then, yeah, I think there was a period where, okay, mobile phone adoption had had gone, like, a lot.

Search engine, like, cloud was happening. In terms of, like, consumer experiences, there was a lot of stuff happening on the just The enterprise space. Enterprise space was growing a lot. Like, you were having a lot of these, like, Uber and and DoorDash and Airbnb, like, those kind of consumer apps, but I felt like tech was not progressing that fast anymore. And then in the last, like, five years, like, really, like, like, last three years have been really exciting.

From all the stuff in AI and in the stablecoins, I feel like there's just something cool to play with. Yeah. Like, new primitives, new paradigms are are coming out. Yeah. When when I first got into crypto, was just it was so exciting to have all these new building blocks to play with. It's like, oh, this is just all these all these Legos that I can start creating things with, and it's permissionless, and it's interoperable. That that was, like, the most exciting exciting piece for me.

And I think we'll see more convergence between AI and crypto. It's not like separate things. Like, they're just converging together, they're becoming very complementary.

Drew Rogers

host

46:33

Yeah. Okay. So as we close,

Charles Yoo-Naut

guest

46:36

something I'm trying to make this I'm trying to make this more personal. I obviously get really fascinated by the tech and what you're building, and it's been also just cool to hang out with you and hear about you're about to become a dad. Yeah. Probably next time we talk like this, you'll be a dad. What are you looking forward to most about being a dad? I'm excited to see the world through her eyes.

I think when you see someone grow up and you you raise a child, you're just able to see the world again with with fresh fresh pair of eyes. Like, you're about to be a deaf a third time Yes. Which is super exciting. So you've probably gone through that phase already twice.

But taking all these these things that you take for granted and start appreciating them, I think that's that's, like, very exciting and just raising a human and something that is a combination of me and my wife and, like, in a human form and and watching them grow and hopefully raise, like, a good contributing member to society and a good person. It's an exciting thing for me and my wife to What what pull together. What quality do you hope she has about your wife?

If you could pick one of her qualities that Oh, yeah. That that's a tough one. That's that's a good one. I I think just like her her passion, she's like, she's very, like, strong willed. She she stands by her principles very strongly, I wanna raise, like, the human who also feels that way, is very principled and That's awesome. And passionate about the things they care about. That's all I can hope for them. That's great. So June, lot of change. Lot of change. Until then, it's been great to be with you. Yeah, man.

Thanks for the time. Well, thank you so much.

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