# Rain raises $250M Series C led by Iconic at $1.95B valuation Stableminded, a Stabledash show. Mar 25, 2026. Charles Yoo-Naut. https://live.stabledash.com/shows/stableminded/episodes/the-stablecoin-card-company-that-raised-over-300m-in-12-j7sQW1vQY3I The stablecoin card issuer's co-founder says Rain settles with Visa in USDC every day and is using AI agents so it can grow without hiring in step. Rain, a stablecoin card issuing company, announced a $250 million Series C in January. The round was led by Iconic Ventures and values the company at $1.95 billion. Co-founder and CTO Charles Yoo-Naut says Rain now processes over 3 billion in annualized card transaction volume, wherever Visa is accepted. ## An early bet on spendable stablecoins Charles Yoo-Naut says he and Farouk started Rain towards the end of 2021, after building conviction that cards were the best way to make stablecoins globally accepted. He says he was frustrated in 2022 and 2023 when people were still looking for crypto use cases, because moving money in traditional fintech was "so broken." ## Settling on Visa rails in USDC Rain settles with Visa Inc in USDC seven days a week, including holidays and weekends, paying for each day's volume. Charles Yoo-Naut says some Visa merchants already receive stablecoins, so for certain purchases stablecoins pass from cardholder to merchant on Visa rails. As a non-bank principal member of Visa, he says, Rain replaces the bank partner, program manager and reseller in the issuing stack. He expects the line between a stablecoin payment and a card payment to blur, leaving "value being transacted on a network." ## Customers and faster launches Charles Yoo-Naut says any financial product can be delivered faster, cheaper and in more markets on stablecoin rails. Rain announced a partnership with Western Union for remittances. He says a traditional banking partner can take six months a year to issue a first card, while one Rain customer went live in 17 days, helped by tools from Mintlify, Coast and Stainless. ## Scaling with agents Charles Yoo-Naut says Rain wants to avoid Block's over-hiring and weighs each hire against what AI will do in 12 or 24 months. He says one compliance person can be armed with 10 agents, and the single business development lead, Nick, works with 20 agents. On agentic commerce, he says agents already use existing cards, and tokens such as Visa Inc Intelligent Commerce make this safer. He describes an emerging idea of "know your agent," and says Rain does not let staff use Cloudbot because the controls are not there yet. Charles Yoo-Naut describes Rain as a card issuer that is already moving stablecoins through Visa rails. He expects microtransactions to stop being blocked by infrastructure and expects AI and crypto to converge. ## Key takeaways 1. Rain announced a $250 million Series C in January, led by Iconic Ventures, at a $1.95 billion valuation. 2. Charles Yoo-Naut says Rain processes over 3 billion in annualized card volume and settles with Visa Inc in USDC seven days a week. 3. Rain went from 15 people to about 95 in a year, and Charles Yoo-Naut says AI agents now do first-pass compliance review and support work. ## Chapters - 0:00 Cold open and sponsor message before the interview - 2:06 Three funding rounds in 12 months reflect a four-year head start - 5:40 Rain processes $3B annualized and settles with Visa in USDC - 11:34 Customers come for faster, cheaper, wider financial products on stablecoins - 17:49 Rain assembles modular partner stacks for each customer - 21:22 Better docs and AI tools cut go-live to 17 days - 25:05 AI agents let compliance and support scale without linear hiring - 31:32 Card and stablecoin payments are converging on Visa rails - 36:13 Agentic commerce needs tokens, consent flows and know your agent - 44:45 AI and crypto revive tech excitement as fatherhood approaches ## Transcript **Charles Yoo-Naut** (0:00) It feels surreal. Right now we're doing over 3 billion 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. If you're going through a traditional banking partner, it can take you six months a year to even get your first card issued. We had a customer last month go live in 17 days. One compliance person can now be armed with 10 agents and we're 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 visa roads. **Drew Rogers** (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. **Host** (1:10) This is interview take one, or interview part one, take one. **Drew Rogers** (1:14) Only one take. Only one take. I only got one shot at this. Well, Charles, we've already been talking for about 30 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 great energy this week. Yeah. And we're excited for this new chapter of Stableminded, 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. Yeah, man. You guys have been stepping out macro and looking at what has happened since we knew you guys. I remember meeting Farouk at one of the borderless happy hours in New York over a year ago. Must have been **Charles Yoo-Naut** (1:54) more than a year ago, **Drew Rogers** (1:55) right? Yeah. We were just getting the business off the ground. Stable Studios was the name of it at that time. We co-hosted that with Persona, Dragonfly, Borderless. I met Farouk and I was just like it just immediately my first impression was with rain was like oh this is different like this is gonna there's a really unique approach and just seeing you guys Mexico City the day I think you announced the yeah was that but that wasn't the last race that was a series B so that was a series B and then since then you've series C yeah what was the last race what's the current update **Charles Yoo-Naut** (2:29) Yeah, we raised our Series C, announced it in January, $250 million, led by Iconic. So yeah, from Series B was, I **Drew Rogers** (2:36) think we announced in October when we were doing it. And then that, so that puts you guys around $2 billion. Is that right? Yeah, $1.95 billion valuation. What does that feel like? It feels **Charles Yoo-Naut** (2:47) 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 12 months, that was just not really expected on our part. So, very grateful. Definitely still feels surreal and just trying to keep up with everything. **Drew Rogers** (3:09) What, for those who are just getting to know you guys, is that sort of secret magic powder that's been sprinkled on Rain? You guys have, I was looking at your career page recently, you're hiring a ton, your go-to-market presence is increasing, you're growing globally. I'll just say it for myself, you guys are dominating. You are clearly in pole position in this category. What was that magic powder for people that We're just getting to know you to get you and why is that valuation warranted given in the category you're in? **Charles Yoo-Naut** (3:40) There's nothing really secret or magic. It's just we were in the right place at the right time. Farouk and I met five years ago through the On Deck Fellowship. Started Rain towards the end of 2021 and just really had a few aha 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. So we started a long time and some of the stuff that we built just takes time to do. So we were able to start four years ago and have that four year head start to be where we are. Really just the progress the last 12 months 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 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 we can talk about, oh, we're principal members of ESA, we built all this on-chain settlement, but 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 this stuff that you did actually led up to this happening. **Drew Rogers** (4:50) It's funny that it's about like, what are the use cases? I think I asked Farouk, 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 money? We see it all. It's really cool to think about what **Charles Yoo-Naut** (5:09) That was kind of frustrating to me when we were building in 2022, 2023, 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. And people are just overcomplicating it almost. It's like, hey, this is already 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. **Drew Rogers** (5:40) 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 analytics side of this, like 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 volumes look like? What can you share on those things? **Charles Yoo-Naut** (6:08) Yeah, so right now we're doing over 3 billion annualized transaction volume in cards. **Drew Rogers** (6:14) So that is like the amount of swipes plus the value of those cards or those transactions on an annual basis. So you said $3 billion **Charles Yoo-Naut** (6:24) worth of payments all around the world. All around the world. So we work everywhere that Visa is accepted. So you can swipe a card wherever a Visa card is accepted and we see transactions being used all around the world. So when we were just at the coffee shop, that **Drew Rogers** (6:39) Pengu Cast Card, 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** (6:48) I use my Cast Card, the new Pengu, the new Pudgy Penguin one that is very cute. So that's powered by Cast. They're one of our partners. So I have a balance on my Cast app. I've loaded Stablecoins and that's given me some credit limit. I have the **Drew Rogers** (7:05) relationship with the payer. So like they, no one knows typically, I mean, you're an anomaly with this experience, but no one would know. **Charles Yoo-Naut** (7:13) An average cost user doesn't know about Rain. Exactly. Their relationship with this cost, their affinity and their brand, the brand they associate the card with is cost. I've gone, I went through the KYC process on that. I set up the card, I sent my stable coins 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 CAS and then CAS will make a decision whether they want to 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 both on the credit rails, you know, settlement with the merchant workshop and multiple days later, but all of our settlement with Visa happens 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 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 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 the transactions that we have done. **Drew Rogers** (8:33) And then the flow of funds that I was surprised to learn recently was like, you guys are actually in the more like the earlier part of the flow of funds first. Walk us through that. So you guys receive the funds and then who are you guys actually in between? I don't know why in my brain, but like being first seems more powerful or more influential. I don't know if you agree with that, but the fact that you guys are actually The order of operations where you sit seems really strategic. Walk through that a little bit. **Charles Yoo-Naut** (9:03) Yeah, so the customers are paying us back for whatever transactions that settled in the Visa network. And then we've settled with Visa for those transactions. So the funds will go, we'll settle with Visa for those funds in USDC on a daily basis. So yeah, we're pretty early in the kind of repayment of the transactions flow. **Drew Rogers** (9:24) What is, cards have been, I think, a very obvious adoption accelerant. What do people, the vantage point you have of seeing the data just gets me really excited. I think you have such a unique ability to, I remember when I walked into Square's office one time, 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 guess it was just the square network of like, People in 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 game. **Charles Yoo-Naut** (10:04) Yeah. We actually have our own, we call it radar. So we call it **Drew Rogers** (10:07) radar **Charles Yoo-Naut** (10:07) because we're more global. What **Drew Rogers** (10:09) are you, what are you seeing? Like **Charles Yoo-Naut** (10:12) we just see pings across the globe. So the way the radar works, it will go from the cardholder's address to the merchant's location. Built those visuals? Yeah, just internally. So cool. We built it internally so we can just look. And we did it for Black Friday just to see all the volume that was happening. So you just see this line go from where the cardholder is to where the merchant is. And also the globe will rotate. To show different pieces of it. Would **Drew Rogers** (10:40) you ever expose? We're thinking about it. We **Charles Yoo-Naut** (10:43) need to do it in a way that protects the privacy of the cardholder. So I don't think we would show where the cardholder is. And then internally, we also show the magnitude. So if it's a larger transaction, that line is actually a lot bigger. So I think we would do it in a way that would protect privacy. We would consider exposing something during Black Friday or some other critical event. Black Friday is a very US-centric holiday and our customers are more global. Maybe the data nerds would love it. Yeah. **Drew Rogers** (11:12) 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. **Charles Yoo-Naut** (11:21) It would be a great, like our customers are not really the end card. 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 that want to issue cards through rain. So yeah, I think those people would, would appreciate it. **Drew Rogers** (11:34) Yeah. Tell me about these people. So right now you guys are talking with Nick and team or probably talking to all these different businesses. What are they, what do they value most about Rain right now that you've come to find is 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? **Charles Yoo-Naut** (11:55) Yeah, our core product is still card issuing. We're expanding to offer the full stack that you really need to launch a financial product and working with 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. Customers are fundamentally coming to us because we can do something cheaper, faster, in more markets than anyone else because we're built on Stablecoin rails, because of the infrastructure that we've developed. And on those three axes, it's really hard to compete if you can nail those three. What are the different flavors of customers? **Drew Rogers** (12:36) Because I'm imagining CAST over here, they are building, and there are many different like neobanks and financial user applications who are at that like, I am using this thing because I want a card. Like I know that versus maybe some of these other go-to markets that are almost like Bringing Rain to market themselves, like 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. You know, you see Bramp, Brex, and like that whole category of companies. How do you bucket these in your mind? Well, when we **Charles Yoo-Naut** (13:10) think about our TAM, that's the idea, like we started in the corporate card space for crypto-native teams. So very new... Very niche, like 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 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 like 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 Drew Rogers, Stabledash Global, Stabledash Live, Stabledash Live, Stabledash Live, Stabledash Live, **Charles Yoo-Naut** (14:22) And then I think within that, you can kind of sub-dement it or you can consider them different use cases, but something like a Remins app. So we announced our Western Union partnership. So Remins is a great use case 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. That seems different **Drew Rogers** (14:55) though in some ways like you have these sort of altitudes and casts of the world. These are like new on-chain native companies that probably we talked with the Modo team for example like Modo was like yeah we like literally started our company because Rain existed 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 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. 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. Exactly. **Charles Yoo-Naut** (15:54) But you're also seeing though now upstarts going after the Western Union. **Drew Rogers** (16:00) Those two groups can compete and you're going to win in both places as they do. **Charles Yoo-Naut** (16:05) So what Man says, that's been an exciting use case to look at. The area that we're getting really excited about is global platforms. So whether you're Airbnb or an Uber, you're paying people out globally. You have to figure out those local payment rails in all those different markets. And that's a call center for you. If you can actually give people wallets, pay them out in Stablecoins real time or **Drew Rogers** (16:30) These are like the nuves for you guys, right? Like more of a nuve style? **Charles Yoo-Naut** (16:34) Yeah, similar to like, hey, how do you turn global payments, global payouts from a cost center to actually a revenue center? You're able to keep the money inside of your ecosystem for longer and you're able to monetize the spending of that. And build more brand affinity as well. 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 an Uber driver can get paid right after the drive finishes. They can get paid streaming while the drive happens if you wanted to. You're not constrained by the rails anymore. You can kind of imagine much new payment experiences. Those are ones that are, I mean, it takes more convincing, more education. It's not as obvious, but that we're very excited about. Yeah, so those are a little bit of flavor, but really, the world is so wide for potential use cases, for potential customers. And we're also starting to see agentic payment use cases come up, which is a whole new... You said **Drew Rogers** (17:28) the word. Yeah, I know. You said it. We opened the can. **Charles Yoo-Naut** (17:31) Agentic payments is really exciting as well, and that's like still early days, I think. People are not sure how it's going to play out, but it's happening already. Agents are making transactions for humans, and I think that's just going to continue to grow. So we're figuring out how can we support those use cases as much as possible. **Drew Rogers** (17:49) It's so cool. It seems like... Alright, so we'll open the agent's can here. But just closing, closing this last loop. 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 flip. We have like that team in mind and you have the Arculus team. It's like they're all these different pieces of this puzzle and you were saying that to make the, and Rain is touching all of them, like you swiped the card. Yeah, **Charles Yoo-Naut** (18:29) those are all our partners. I mean, it's cool **Drew Rogers** (18:32) because everyone's playing a different role. Like if that fintech wants to issue the stablecoin with Braille or, you know, get the rails built with coinflow and settlement built with them. And **Charles Yoo-Naut** (18:42) Arculus, like Compost Secure is an investor in Rain. We issue a bunch of Compost Secure cards. Yeah, it's like a big happy family. **Drew Rogers** (18:49) 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 want to 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 want to put people in the position to say, Hey, you can use us for this, but go call Tom from Arculus and Dave from CoinFlow. You don't want to force people to do that. How are you delivering completed stacks to **Charles Yoo-Naut** (19:18) customers **Drew Rogers** (19:19) right now? **Charles Yoo-Naut** (19:20) We try to be as agnostic as possible. So if someone comes with us with a preferred partner, we will make that work. And our stock 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 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 **Drew Rogers** (19:52) 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, like what do those look like in your mind right now? **Charles Yoo-Naut** (20:10) Yeah, it can vary depending on what the actual product that the customer is trying to deliver is. But typically there's like virtual accounts, on and off ramping, there's wallets. Like interop with banking and like... Yeah, interop with like existing financial rails. Like you want to... **Drew Rogers** (20:26) You might **Charles Yoo-Naut** (20:26) want to be able to go in from ACH or SWIFT and you want to be able to go out into a bank account. You want to be able to store those in like a wallet somewhere. You might want an MPC wallet or you might want a non-custodial, like fully non-custodial, 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 metal card with a hardware wallet attached to it. So like, okay, we work closely with Arculus and we can deliver that for you. You might want to issue your own token and we have partners that can help you issue your own token. If you're very opinionated on reserve management or yield, then that might dictate which partner we would recommend. So **Drew Rogers** (21:13) yeah, that's becoming more of the roles, like kind of... Yeah, you have to consult, really. Yeah, like it's becoming **Charles Yoo-Naut** (21:18) a consultative approach, especially for larger deals, **Drew Rogers** (21:22) more enterprise use cases. Have you thought going, 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 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. We try **Charles Yoo-Naut** (21:40) 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 when they're going live and growing, how do we reduce that as much as possible? If you're going through a traditional banking partner approach, it could take you six months, a year to even get your first card issued. We had a customer last month go live in 17 days. **Drew Rogers** (22:08) From **Charles Yoo-Naut** (22:10) signing the contract to issuing their first card. So we're always looking at, okay, how can we bring that down? What are the areas and how do we make integration simpler? How do we improve our docs? Where can we inject AI to automate things so you don't have to talk to a human if you don't need to? How do we make the contracting process **Drew Rogers** (22:26) simple? **Charles Yoo-Naut** (22:27) How do we simplify our pricing tiers? **Drew Rogers** (22:29) What's been the biggest unlock to accelerate that down 17 days recently? **Charles Yoo-Naut** (22:35) Yeah, 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. So we just didn't have like the manpower to 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 docs. So improving the documentation, improving like sample code. We're rolling out SDKs now to make 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. **Drew Rogers** (23:29) Is the user experience, so I'm in the API docs, is that like a chat bot or like a text? And is it something that they're typing or speaking eventually? Like what is that like? Right **Charles Yoo-Naut** (23:39) now it's a chat bot inside the documentation. So we use Mintlify, they're great. **Drew Rogers** (23:42) Mintlify is the name? Mintlify? Mintlify. **Charles Yoo-Naut** (23:44) Yeah, **Drew Rogers** (23:44) they're **Charles Yoo-Naut** (23:45) like a docs infrastructure provider. Really interesting. Shout out to Mintlify. Yeah, Mintlify has been great. They're also crushing it. Every docs page I go to **Drew Rogers** (23:53) now is powered by them. Sounds like it's not like a crypto business. It's just like a, you know, everyone's using them for APIs. **Charles Yoo-Naut** (23:59) Yeah, yeah. Have you heard of 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 Coast demos for customers and they can see how their app would integrate with the Rain APIs. So that's a lot. We're working with another company to help with, they're called Stainless, so helping generate different SDKs, different languages for our customers. Service-side SDKs in Python or Node.js 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 **Drew Rogers** (24:39) SDKs. **Charles Yoo-Naut** (24:41) 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 want to be injecting humans is like that more of that consulting and then the answering questions, debugging things, how can we push that to AI as much as possible? **Drew Rogers** (25:05) Yeah, so let's open the aperture of agentic commerce AI like humans. Okay, so we, 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, you know, eventually that's not going to be a person asking those questions. Agents will be evaluating these different things and making the best decisions and doing that work. Drew Rogers, Stabledash Global, Stabledash Live, Stabledash Live, Stabledash Live, Stabledash Live, Stabledash Live, **Drew Rogers** (25:51) leader of people. Where are you seeing the most valuable use for where the human, like the human touch matters? Yes. What does that look like versus maybe what you think is going to start to, I think everyone's freaking out about block right now and what happened. I'm X block and like, 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 touch? **Charles Yoo-Naut** (26:15) Yeah, I think we're in a pretty 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 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 I think it's really hard to actually be an AI founder, but being a fintech founder is great because I'm able to utilize all these AI tools and they're bringing down the costs 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 want to get into the block situation where they Drew Rogers, Zach Fowler, Aaron Stanley, BVNK, Dani Vilardell, Stabledash Global, Stabledash Live, Stabledash Live. **Charles Yoo-Naut** (27:29) We were only 15 people a year ago. We're like 95 people now. How do we prevent that over hiring? Thinking through like every new hire that we have, what is their role going to be like in 12 months or 24 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 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, the number of transactions you're doing. I think with AI, you're starting to see it become more logarithmic. You're starting to see an 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 can now be armed with 10 agents that were doing the work of 10 people. So we're trying to invest a lot in AI for compliance, AI for support. And it actually 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 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 AI and if you provided the right contacts. Drew Rogers, Stabledash Global, Stabledash Live, Stabledash Live, Stabledash Live, Stabledash Live, **Drew Rogers** (29:31) People who are doing deals and making introductions and have networks and whatever we call those people now. Partnerships, what's your take on that side of the business? You guys have been hiring a lot of those kind of roles lately. How has that side of the house changed in your mind in the last three, five years? From just like the way that deals get done, the way that, I mean, 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 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 the enterprise commercial function changing? Like how many people do you need? **Charles Yoo-Naut** (30:17) Yeah, 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 typical A model. We don't have any quotas. Just keep paying Nick more. Yeah, it's really just Nick. Nick is the only one in the BT team, and he has 20 agents in there. **Host** (30:35) They have different names, you know, but... **Charles Yoo-Naut** (30:38) No, it's still a pretty lean team. Almost everyone, I think the title is BDN Partnerships. We don't have anyone that has a really different title in that org. And that is a reflection of 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 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 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 smaller deals, startups, we're trying to make that as self-service possible while having the right guardrails in place to make sure that it's the kind of partner that we want to work with. **Drew Rogers** (31:22) And **Charles Yoo-Naut** (31:22) then the humans can focus on the larger deals, the more complicated deals, the ones that will require education or consulting. So we're growing the team more in that realm. **Drew Rogers** (31:32) Yeah, you guys have done a really good job of just showing up in person, hosting events. Rain has always seemed very embedded within the builder community. Okay, so we've talked about the role of more of the AI workflow update within more just 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 human How do you see those two opportunities for Rain? Because you kind of sit, I'd imagine, in both, where you have the B2B side. How do you think about the buckets of opportunity for both human-centered commerce and agentic commerce right now? **Charles Yoo-Naut** (32:20) Yeah, it's a very exciting time to be in this space. Also, we're at the intersection of cards and stablecoins, and I feel like those are coming to a head with agentic commerce, where people are debating what the future is. Are agents going to use stablecoins? Are they going to use cards? **Drew Rogers** (32:39) We even say cards and like cards can be physical. They don't always have to be. **Charles Yoo-Naut** (32:44) 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 going to be transacted. And that doesn't have to be a physical card, right? We see it can be a token. On Apple Pay, it can be a token that an agent controls. And then what happens on the settlement layer that we're already showing with our work would be so it doesn't have to be fiat. The settlement for that message and that value transfer can be stablecoins. So I do think that the distinction between cards and stablecoins is not as big as people are making it seem. And then the actual divide between a stablecoin payment and a card payment is going to start blurring. There's going to 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 going to start blurring and then you're just going to have value being transacted on a network. Interesting, **Drew Rogers** (33:45) because right now it seems **Charles Yoo-Naut** (33:46) they do seem fairly separate in terms of how people think about them. Visa already has merchants that are getting settled in stablecoins. And we're an issuer settling in stablecoins. So there are certain merchants where from the cardholder to the merchant, there are stablecoins passing all the way through already. And it's happening 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. So that would **Drew Rogers** (34:14) almost be in your, then this is for me what I get probably most excited about as like a payments minded, like I started at Square. So 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 like spending like hours looking at all the hops of like a payment transaction on a big whiteboard. It was like seven or eight different like big hops that money takes. And it's like, I think Square had like a, you know, we're going to take this nine hop and we're going to 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 just now getting there. But what you just said is sort of like, Hey, we're starting to see the merchant side. Yeah. What we've done is compress the traditional issuing stock already. So traditionally, you have your bank partner, you have your program manager, you might have a reseller, and then you actually have an app, and then you have a cardholder. **Charles Yoo-Naut** (35:26) So like those were all those hops and we've merged the other, 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 again? Like the BIN sponsor, which is usually a bank in many cases, you have like the program manager that's on top of that BIN. So like in the fintech world, you got... **Drew Rogers** (35:48) You guys have that yourself? You guys have a BIN sponsorship? Is that true? We **Charles Yoo-Naut** (35:51) are a principal **Drew Rogers** (35:51) member of Visa. It comes with that? **Charles Yoo-Naut** (35:54) So the BINs that are our cards, there are BINs. We're the license holder on the Visa side. Cool. **Drew Rogers** (36:01) Yeah. **Charles Yoo-Naut** (36:01) So we're a non-bank principal member. Amazing. And so that kind of checks a lot of those. So 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 Stablecoins that really enabled that to happen. But 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 want to just give my agent the secret numbers on my card. I want to give them a token. Visa's doing that with their Intelligent Commerce. Now my agent 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. So that's a regular... **Drew Rogers** (37:06) Is that typically like a biometric signature right now? Something like that? **Charles Yoo-Naut** (37:11) Usually it's like an SMS or an email. So you've probably seen like the 3DS, like 3D secure flow. It's not as popular in the US, but 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's like a 3D 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 being built. **Drew Rogers** (37:45) They're also like agent **Charles Yoo-Naut** (37:46) commerce might start becoming a thing where maybe they choose to interact directly in stablecoins where they have a wallet and they're just sending each other stablecoins directly without using Visa network. That is like a potential, maybe more merchants are going to use some of these new standards like X402 or something to accept stablecoin payments or accept agentic payments. **Drew Rogers** (38:07) What's the current way so like right now what I'm I'm gonna leave this San Francisco a couple days and I feel super convicted it's 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 like 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 think I think we could build a social media agent to go do that. Or like, I'm starting to think this way. What is the today best way for me? Where do I go after we stop talking? What I'd love to have is to go create an agent for a certain purpose and then equip them with a Rain-powered card that I can just go, you know, I'll throw some USDC into that. What's like the lowest, simplest starting point to do that? **Charles Yoo-Naut** (39:01) Some customers that are enabling **Drew Rogers** (39:03) this that I can send your way. We're gonna make it simpler. But we're early still. **Charles Yoo-Naut** (39:07) We're still early. I think you're starting to hear more announcements of people where the agent can just spin up a Rain card for a single purchase and then that card gets deactivated once that purchase is made, so additional protections. **Drew Rogers** (39:22) What was **Charles Yoo-Naut** (39:22) the **Drew Rogers** (39:22) partner you guys announced on this? It was like a couple months ago and they had that specific tech and it was like... There's one called Clutch that doesn't use... **Charles Yoo-Naut** (39:32) I wasn't sure if **Drew Rogers** (39:34) that's what you were... It was like a per transaction or kind of like a build your own. It was a company that allowed people to architect their own. Was it them? **Charles Yoo-Naut** (39:43) It's not necessarily for agents, but I think that's the natural evolution of it. We're going to see more and we're trying to make it easier for our customers to build these types of experiences and getting input from them of what they would like. What do they need? What protections do they want? What would make the integration easier? What would make the experience better? **Drew Rogers** (40:02) 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. I remember there was a lot of this when we were dealing with like NFT purchases and it's like KYC 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. Are you seeing anything in this? Am I thinking about that right, or who's building? **Charles Yoo-Naut** (40:40) I think there's different ways. There's starting to become this concept of know your agent and what does that mean. Because agents can, if I provision **Drew Rogers** (40:48) an agent, and it's going to do illegal commerce on my behalf, **Charles Yoo-Naut** (40:52) I'm going to do **Drew Rogers** (40:52) it. You're on the hook. I'm on the hook. I mean, that seems like a really interesting **Charles Yoo-Naut** (40:57) Yeah, like for us, for example, we don't allow the team to use Cloudbot and some of those because we feel like the controls are not there in place yet for it to just not completely wreck you. It will 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 were treating agents is like we're still going to KYC whoever is 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 going to give an agent a card and trust that **Drew Rogers** (41:26) So agents will always be associated as an extension of a human being who will be, at least right now in Rain's definition, or like how I'm probably thinking about it. Yeah, for now, unless there's **Charles Yoo-Naut** (41:35) new guidance **Drew Rogers** (41:36) or new laws that are in place **Charles Yoo-Naut** (41:37) around agents, I think that will... Same thing with autonomous vehicles, right? If you go into a Waymo and it hits someone, is the Waymo responsible? Is that **Drew Rogers** (41:50) car responsible? I think there's... The person who's in the backseat. **Charles Yoo-Naut** (41:54) 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 going to skate on some of those issues and try to get ahead of them but it's still early days. **Drew Rogers** (42:21) Yeah, I can imagine microtransactions generally from what I understand about agents, stablecoins. We talked with Lewis from Circuit and Chisel yesterday about this of like micropayments specifically compared to like a 2.9 plus 30 cents transaction. Yeah, it's too expensive for... There are very clear use cases where stablecoins are superior for agents to use and they will and it's always on all the things and just that that unlock there it's pretty powerful if you think about it and if it's micro for 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 like the tickets are Tickets, meaning transactions, are of a certain size. Certain states 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. Because stablecoins, from my understanding right now, 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 seem to be a nice I think that's a **Charles Yoo-Naut** (43:39) clear, they've been talked about for a while. 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. It's just gonna be like- **Drew Rogers** (43:55) It's like we're actually not even seeing that yet. I hit Bloomberg and they're like, pay us two bucks. **Charles Yoo-Naut** (44:02) Maybe I'll pay 10 cents to read this article. **Drew Rogers** (44:04) Yeah, but I don't want to know. I'd rather just like something like that kind of exist and I can just face ID in. Yeah, I **Charles Yoo-Naut** (44:12) think right now there's just a lot of friction in payments. That's probably where agents are going to 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 want to use based on what kind of site this is? Maybe I want to 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 is going to 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. **Drew Rogers** (44:45) 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 going to be fun to hopefully get the opportunity to just continue to follow you guys and see what happens. Yeah, if you love tech, if you **Charles Yoo-Naut** (45:01) love innovation, it's just such an exciting time to be alive. I **Drew Rogers** (45:04) think there's a period where tech started to get boring a little bit. When was this in your mind? **Charles Yoo-Naut** (45:09) I think it was, for me, mid-2010s, like 15 to 20. Where were you at this time? I was in the Bay Area. So 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 bad. But before then I was in the Bay Area. We're on the West Coast since 2008. I was on the West Coast for like 11 years. I think there was a period where mobile phone adoption had gone a lot, search engine, cloud was happening. In terms of consumer experiences, there was a lot of stuff happening on the... **Drew Rogers** (45:47) The enterprise space. The enterprise space **Charles Yoo-Naut** (45:49) was growing a lot. You were having a lot of these like Uber and DoorDash and Airbnb, those kinds 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 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. **Drew Rogers** (46:08) Yeah, like new **Charles Yoo-Naut** (46:09) primitives, new paradigms are coming out. Yeah, when I first got into crypto, it 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 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 and they're becoming very complimentary. **Drew Rogers** (46:33) Yeah. Okay. So as we close, 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. **Charles Yoo-Naut** (46:45) Yeah. **Drew Rogers** (46:45) Probably next time we talk like this, you'll be a dad. What are you looking forward to most about being a dad? **Charles Yoo-Naut** (46:51) I'm excited to see the world through her eyes. I think when you see someone grow up and you raise a child, you're just able to see the world again with fresh pair of eyes. Like you're about to be a dad for the third time. Yes. Which is super exciting. So you've probably gone through that phase already twice. But taking all these things that you take for granted and start appreciating them, I think that's 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 watching them grow and hopefully raise a good contributing member to society and a good person. It's an exciting thing for me and my wife to pull together. **Drew Rogers** (47:29) What quality do you hope she has about your wife? If you could pick one of her qualities. Oh **Charles Yoo-Naut** (47:34) yeah, that's a tough one. That's a good one. I think just her passion. She's very strong-willed. She stands by her principles very strongly and I want to raise the human who also It feels that way. It's very principled and passionate about the things they care about. That's all I can hope for them. **Drew Rogers** (47:52) That's great. So June, a lot of change. Well, until then, it's been great to be with you. Thanks for the time. Well, thank you so much.