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The Bigger Stage w/ Matt Stone is a conversation series about leadership, relationships, and the stories that expand influence.
Matt Stone sits down with CEOs, founders, leaders, and creatives to explore the human moments behind growth—how trust is built, how visibility changes responsibility, and how storytelling becomes a leadership skill as stakes rise.
This show is for entrepreneurs and leaders stepping into bigger roles, bigger audiences, and bigger impact—who want to lead with clarity, credibility, and connection, not performance.
(edited full) The Bigger Stage - Duncan Barrigan
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[00:00:00] Turns out you need a permit to bring a horse into Manhattan. The horse box was stopped on the way in. There's more than $100 trillion of payments that go around the world between businesses done human to human. It's actually a communication and negotiation problem. It's not a payments problem at all.
[00:00:23] Matt Stone: My guest today is Duncan Barrigan, founder and CEO of Lunos or Lunos. We're gonna find out which one it is. An AI partner that manages receivables the way you would if you worked on it twenty-four seven, never forgot a thing, and read every message anyone ever sent you.
[00:00:40] Before Lunos, Duncan spent eight years at GoCardless, helping take it from a UK direct debit provider to a global payments unicorn. He could have built almost anything next, but instead, he chose one of the least glamorous but most impactful corners of the business: getting paid. That choice is what I wanna get into today because [00:01:00] behind it is a question every founder eventually faces: Do you chase the shiny thing or the thing you can't stop thinking about?
[00:01:08] And what if those two things are different? Duncan kept coming back to finance people spending 10 hours on a single invoice to a CFO whose accounts payable team had standing orders not to pay the lawyers until they chased him personally. Work that's been done the same way for hundreds of years by humans badly.
[00:01:29] This is a conversation about Lunos, and it's a conversation about conviction, what it looks like to bet your career on a problem most people walk past, and why the most human stories are often hiding inside the most technical ones. Duncan Barrigan, welcome to the bigger stage.
[00:01:45] Duncan Barrigan: Thank you so much for having me, Matt. It's great to be here.
[00:01:48] Matt Stone: So the question everybody is asking, or they should be, is it Lunos or is it Lunos? Please declare the, the definitive answer. The people wanna know.
[00:01:59] Duncan Barrigan: I think [00:02:00] that it is Lunos, but every American that sees the word afresh says Lunos. So it's kind of, you know, founder meets reality, and I, I, I think reality is probably going to win, but at the moment I still say Lunos. And then everyone else says Lunos, exactly as you did.
[00:02:17] Matt Stone: It's the, uh, you know, look, it's the fate of any good Englishman who's operating in Manhattan. You know, another Englishman in Manhattan trying to fight the, the culture that just wants to make an O a hard O. Uh, what can I say? But what isn't hard is having this conversation 'cause it's a lot of fun. We got a chance to meet in person the other day in your office, which was an absolute blast and, um, I'm, I'm basically looking forward to continuing that conversation on camera and sharing that with the world.
[00:02:45] So, uh, first we're gonna get into your journey and as I alluded to in the intro, um, but let's just put on record whether it's Lunos or Lunos. Uh, it's a pretty cool company. It's, it's new, but just [00:03:00] explain what it's all about and who you serve and what problem you solve.
[00:03:05] Duncan Barrigan: As you say, it's a problem that is, I think-- don't think anyone's described it as sexy, but it is extremely, extremely large. So for anyone who's not familiar with it, there's more than $100 trillion of payments that go around the world between businesses, uh, through ways that I would say thousands rather than hundreds of years have been done human to human.
[00:03:26] So the very first writing was, was ledgers, was invoices and receipts. And since then, humans have done work with each other and they have, you know, written it down, whether it's on a stone tablet, whether it is on a laptop, on a, on a, you know, in a CSV, in a spreadsheet, whatever. Um, and it's been done with humans.
[00:03:44] Uh, and you know, we call them accounts receivable and accounts payable teams. And this $100 trillion-plus, uh, world has, has just operated human to human for, for, for as long as writing. We're building the AI agents that will turn that into, [00:04:00] uh, an agent-to-agent problem, not a human-to-human problem.
[00:04:05] Matt Stone: Which, you know, the agent-to-agent solutions are coming in so many different ways in business and in life. It's, it's-- And, and have been here actually for a little while already in some corners. But, um, but how are you setting out to do it differently than it's currently being done that is an improvement on our current reality?
[00:04:27] Duncan Barrigan: I think that for my entire time at GoCardless, I was naturally-- you're kinda biased by what you're doing, right? So we were, as you said, pulling money from people's bank accounts when it's due. And I would, I would go and speak to these, uh, these companies with enormous accounts receivable teams, you know, tens of, tens of people doing this.
[00:04:44] And we'd kinda be saying, "Look, why don't, why don't you just pull the money out of someone's bank account when it's due?" It's, it's functionally what we'd be saying to them. And, you know, sometimes that was the right answer, honestly. But, you know, it, it still only covers a couple of percent. I mean, it's still, still a vast amount, but it's a [00:05:00] couple of percent of the 100 trillion, which is, which is still done, done human to human.
[00:05:03] I think the, the reason is, uh, that it-- this is the epiphany that I had that, that started the business really, is that it's actually a communication and negotiation problem. It's not a payments problem at all. And there are very good reasons why people have used humans for 6,000 years to do this. Uh, so, so the, the way we're different is to recognize basically, you know, instead of old me trying to, you know, trying to come with, as everyone else does, "Here's a different way of doing this.
[00:05:30] Please just do it this way instead." It's saying, "There's very good reasons you've done this. We're gonna make it work," you know, as you said in the intro, "We're gonna make it work how you would do it yourselves and how you are doing it, but it's gonna be an AI, and therefore it's gonna be scalable, and it's gonna be also optimizable and able to achieve things that you can't because of the way it works."
[00:05:49] But yeah, what's really different is saying, "Stop, stop telling everyone to do it differently," and say, "No, I, I get why you did it that way. Let's just, let's just make that into something that an AI can do for you instead."
[00:05:59] Matt Stone: [00:06:00] Yeah. Now, you're based in New York City, and, um, obviously it's a financial hub, and so there's some kind of obvious reasons why a company like yours and why you would wanna be based there. But tell me about your experience being an entrepreneur with a startup in New York City. What-- How has that colored, shaped, influenced sort of your mentality?
[00:06:20] Duncan Barrigan: Yeah, I came over here from London where I'd been living for many years building GoCardless. And I remember at the time people often tell you not to change too many things in your life at once. I decided to move continent, quit my previous exec role, move in with my girlfriend, and move to, uh, move to New York and start Lunar all in one go.
[00:06:41] Uh, so it was a, it was a, it was a relatively bold set
[00:06:44] Matt Stone: Do you have a shrink on-- Are you paying a shrink, um, to be there on s- on standby? 'Cause that's, that's a lot.
[00:06:51] Duncan Barrigan: Yeah, the, the one that I think was the least good idea within it actually was the timing because we also moved to New York in January, which people did say, "Are you sure you [00:07:00] want to move to New York in January?" So that one I think was, like, the biting minus 15, minus 20 Celsius that threw in with that was probably the most self-inflicted wound, I think.
[00:07:10] Matt Stone: Yeah. You still have your nose attached to your face, which is... You obviously got through it. But man, I, I remember when we moved out here, I came out on a scouting trip in January, uh, and I was like, "What, what am I doing?" Uh, and it w- it was exactly as you described. I was like, "This is cold." So, yeah.
[00:07:35] Duncan Barrigan: Yeah, so I think since then, you know, it's been-- New York is-- I love the place. It is obviously a very intense place. I remember coming back to London after a few months and thinking, "It's funny, I never realized London was actually a quiet, leafy green village," when you leave the concrete jungle. So, you know, it's been an intense experience, but it's been such a rewarding experience.
[00:07:55] I don't, you know, I don't regret it for a second. But certainly I, I did things in a fairly bold way, I suppose.[00:08:00]
[00:08:00] Matt Stone: So, I mean, actually, I'm gonna pull on that thread for a quick second, 'cause I do think people who live in community love to how-- to hear how other people see it when they come. Like, what-- how would you describe-- I mean, London being an iconic city, London, New York, um, you know, Tokyo, uh, Hong Kong, um, et cetera.
[00:08:18] Um, culturally speaking, what have been sort of the biggest differences that you've noticed in terms of operating in this, in this space?
[00:08:29] Duncan Barrigan: I agree with the people whose theory is the world was sort of- Divided by a common language in a sense, in that I think you think it's much more similar than it is. Uh, and then, you know, as you get to know... I mean, I still, even to this day, I keep hearing new words that Americans say totally differently to us and I find them out in some, in some weird way.
[00:08:48] Someone said to me the other day that, uh, a scheme is kind of like, it's not necessarily a bad thing in Britain. This was yesterday. And a scheme in America is, is much more, you know, you're scheming. So, you know, the equivalent of like the, [00:09:00] you know, the, the ch- the new children's school meal scheme in the UK or something sounds very odd in America.
[00:09:05] So I think it's kind of, to be honest, it's been the experience of, of just constantly finding more fascinating and I, I, I love it. I, I'm fascinated by different cultures, but I think I've definitely been surprised at the depths of the distance, the differences despite having, having been here before. But New York itself, I think the, the startup scene compared to London, kinda reflects the cities.
[00:09:25] The New York scene is, it's big, it's intense, it's hustly, it's grindy. It's got this incredible energy to it that, you know, the London scene's come on leaps and bounds, but I think you, like the, the imprint of the two cities comes across in how they, you know, how they approach startups too.
[00:09:42] Matt Stone: What do you think the advantage, other than the obvious, you know, access to people who move a lot of money, uh, and who finance things and, um, and companies that have a lot of accounts payable and receivable issues. Um, other than that, what do you think the advantages of having a startup [00:10:00] in, in New York City are?
[00:10:03] Duncan Barrigan: Those are pretty big advantages that you've, you sa- said other than.
[00:10:07] Matt Stone: So none. I've, I've basically uncovered there's no other advantages. It's super expensive. It's loud. It's... I'm
[00:10:15] Duncan Barrigan: I think the company one, the, the, the, the customer side is bigger than I had anticipated. I think it's one of the, there's some things where you can know it academically and you can experience it viscerally and they're not quite the same thing.
[00:10:28] Like obviously, look, I'd, I'd seen the economic stats. I knew that America was bigger than the UK. You know, this, this wasn't a surprise, but the practical ways in, uh, in which that turns out, anything from like whatever segment of ICP you look at and how narrow it, uh, and how big it is in, in the US to, I- a friend in London had messaged me something about like, "Oh, I'm thinking about different ways to sort of reach the tech audience for voice agents.
[00:10:54] Like, what do you think are the best, like, I'm trying to think of some of these channel to do this." And that morning I had cycled past a [00:11:00] massive sign, uh, somewhere in, in, in downtown saying like, you know, uh, basically advertising to founders their AI voice agent. And I thought, well, here I just cycled past people putting billboards up because, you know, it's dense enough and crazy enough that this happens.
[00:11:14] And, you know, on the London side they were thinking, "Oh, what's the best way to actually reach these people?" So I think that just really, you know, cemented in me like the, there's something about the scale and the density that I think is another league when it comes to what you get with such a big market and so many, you know, so many companies in one place.
[00:11:31] Matt Stone: I think you're hitting on something. You've said it in a different way than I've ever heard that resonates more with me in my own experience, is, um, the density issue and how that impacts it. Because I mean, when you're out in New York City and you're at a cafe and a nondescript cafe, I mean, this is even a local chain, you might be sitting next to a life-changing conversation.
[00:11:53] Like they're just-- people are just Everywhere. Um, and, and that, you know, celebrity [00:12:00] sightings is like the smallest thing. Like, you know, they are everywhere, but like, just amazing consequential people, uh, are everywhere, and they're right in within a, a couple of miles or kilometers of each other. So, uh, okay.
[00:12:12] But listen, when you were-- I think we started this conversation in your office, but I wanna continue it 'cause I think, um, when I asked you about, you know, when you were five years old, did you dream of being an AI startup founder? Um, and of course you didn't, but what-- Can you-- Is it unbelievable to you where you're at now, or does it make sense when you look back?
[00:12:33] Duncan Barrigan: I think it-- I mean, it absolutely makes sense as I look back. I think looking-- It's so hard looking forward. I mean, the, you know, as I, as I said to you the other day, when I was five, I, I, I wanted to be an astronaut. I mean, frankly, I still do want to be an astronaut, but as a, uh, as a Brit, I, I looked at the people at the time who'd been British astronauts, and there were three.
[00:12:50] And two were half American, half British, and actually went with NASA and were mechanical engineers. And like I'm, I'm not half American, so I abandoned that one. The third had won a [00:13:00] competition with the Russians, which, you know, in the '90s didn't necessarily seem like the best bet for me as a, as a small child.
[00:13:07] So I decided that it would make much more sense to just make enough money to be able to pay my way into space, which I, uh, you know, I still very much do wanna do. Uh, so when you asked the question, I was like, "Oh, maybe, maybe it actually does all lead directly from my, uh, my dreams of being an astronaut."
[00:13:22] Uh, but yeah, I don't-- Um, I'm not someone that was, like, the extreme entrepreneur as a child, like constantly trying to sell things. I was more the stifled entrepreneur. You know, I came up with the idea of selling-- buying packs of Pokémon cards when I was 11 and selling like the Charizards to people. But unfortunately, there was no payment infrastructure at the time, and I was in a rural village in North Yorkshire, so I like had to abandon my plan to sell, to sell prized Pokémon cards on the internet 'cause I didn't know how to do it, you know?
[00:13:49] So I suppose I was always a bit more stifled rather than necessarily able to act on them.
[00:13:54] Matt Stone: But the instinct was there.
[00:13:55] Duncan Barrigan: Mm.
[00:13:56] Matt Stone: It was there. I, I, I hear that clearly. And, [00:14:00] um, and the astronaut thing has you've-- How does the space and the astronaut theme has played out even in the brand of, of Lunos or Lunos, depending on where we're talking? Um, it, it plays out now. Like, how have you extended that into the brand that you're building?
[00:14:17] Duncan Barrigan: Yeah, this, I, I think the, the connection must be purely, uh, subconscious, subliminal rather than, uh, rather than intentional 'cause I hadn't thought of this until now. But the, the story of the brand is, uh, is one I'm actually kinda really proud of, I suppose. So, you know, have you ever, have you ever done a rebrand, by the way?
[00:14:36] Is this something you've, you've... Yes, you, of course you
[00:14:39] Matt Stone: It's not a small thing
[00:14:41] Duncan Barrigan: yeah, and there's always the three options and there's always one option that is actually the good option that you should pick and no one ever does because it's just a bit too bold. Uh, and you know, we did a rebrand at GoCardless and the, the team did a fabulous job and we, you know, we went through it.
[00:14:54] We had the internal team, we had the agencies and, you know, of course there were three and we picked one that we [00:15:00] thought was really good and was slightly safer than the one that we were a bit worried about. Whereas this time with, uh, with the, the fabulous people I was d- I was doing our, you know, thinking of our initial brand with, we'd been discussing the fact that to, to the outside people think of this $100 trillion world as kind of like surely this isn't a mess.
[00:15:19] Whereas everyone inside knows that it's just, it's just carnage and in fact it's, it's the Wild West out there in terms of getting your, getting your invoices paid. So we sort of had this concept and then, uh, you know, the idea was, well, why don't we actually lean into that? And, you know, this line, taming the wilds of receivables, uh, was kicking around in our heads and this was, this was the third option which was, you know what?
[00:15:42] Let's be different. Let's lean into it. Let's go bright pink. Let's have the space cowboys. Let's wrangle revenue, tame receivables, all the rest. And it was one of those where at first, like we, on the call, we, you know, we almost dismissed it. We were like, "I mean, this one's amazing, but like, you know, we're not gonna do
[00:15:56] Matt Stone: But we're never gonna
[00:15:57] Duncan Barrigan: this one."
[00:15:58] I mean, come on, like it's amazing, [00:16:00] but, uh, should we return to the others? And then the next morning I just thought, you know what? Like time to, time to have some courage. Let's actually do this. So it's like I'm, I'm, I'm picking that one.
[00:16:10] Matt Stone: So you're-- It literally came from you ha- sleeping on it and going, "You know what? No, we're gonna go bold this time."
[00:16:17] Duncan Barrigan: Exactly. Exactly. And now one of our, you know, we have our, our values, there's only three single word values and one of them is courageous and it's partly inspired by decisions like this because you have to be willing to, to risk things. And now honestly, now I think this is like a superpower that we've chosen that other people haven't because it would be so weird to no- like you're a whatever, a late stage company, you can't just suddenly adopt space cowboy and bright pink.
[00:16:41] It just looks completely un- you know, like the authenticity's not there at all. Whereas, you know, we've chosen it now, so
[00:16:47] Matt Stone: Yes. That's actually a really good thing. Like, when you go bold early, it's, it's-- people will buy it. When you go bold late, you run the risk of people going, "Oh, you have an identity crisis. What's wrong with you?" [00:17:00] It's like the, the older person who buys the sports car that they sh- they really
[00:17:03] Duncan Barrigan: Oh, that's such a good analogy. Yes, that's what you would be if we- if someone tried to copy our brand. It's, it's not copyable because you can't reverse engineer into it. You'd look like the aging person buying the cliched sports car.
[00:17:15] Matt Stone: Yeah, and like trading in your spouse for, you know, the newer model, you know, that kind of cliched sort of thing. Right. Um, now behind you is a picture of, uh, an article that kind of ties into the story, I think, if that's the article,
[00:17:29] Duncan Barrigan: It is, yes.
[00:17:30] Matt Stone: You did a great PR stunt that, that I think worked pretty effectively.
[00:17:35] Tell, tell us about that.
[00:17:36] Duncan Barrigan: yeah. It was, as we were, you know, coming out of the... I mean, it wasn't really, I wouldn't really call it stealth. That's a topic for another day. But, you know, as we were announcing ourselves to the world, um, we were thinking about what to do to mark this. And at this point, you know, obviously, we'd, we'd figured out the brand and we were working through it.
[00:17:54] And, uh, it was in conversation with Sir Alex, uh, our Head of Growth, and then [00:18:00] the, um, the PR team that we were working with, who are really great, uh, Maury and Ryan. And it just sort of came out of like, what... You know, we started kicking around these ideas of how about we, you know, lean into this even more?
[00:18:11] You know, how about we, how about we do something then... And then someone, I, I, I think it was Maury maybe, was like, "What if we got a real cowboy? What if we got a horse?" Um, and then again, it was one of those ideas, and this is where the, you know, that, that, that courageous value we try and live by is. One of those at, at first you almost dismiss it.
[00:18:29] You're like, "Uh, I mean, yeah, sure, we could send a cowboy to lasso the Wall Street bull, but, you know, should we get back to what we're actually gonna do?" And then again, you have this moment where you think, "Maybe that's not silly." Maybe we should actually do it. And then the next thing you know, there's, you know, the Slack message with, "Just heard from the commissioner's office about the permit for the horse."
[00:18:51] And you think, "Okay, this is..." Turns out you need a permit, by the way, to bring a, to bring a horse into, into Manhattan.
[00:18:56] Matt Stone: Uh not, not shocking. You probably need like a gazillion [00:19:00] permits for what you did. Yeah.
[00:19:01] Duncan Barrigan: They were actually stopped. The horse box was stopped on the way in. You're not even allowed to... I mean, I thought it was reasonable to think the Wall Street bull, to ride around and lasso the Wall Street bull, maybe you need something. But even to bring the horse into Manhattan at all, actually, it turns out, you can't bring a horse in a horse box into Manhattan without getting stopped by the police and asked for your permit.
[00:19:18] So, you know, don't try this at home, people. Uh, but yeah, and then we thought, "Let's, let's do it." And then the next thing you know, there we were amongst, uh, hundreds of really quite bemused tourists handing out mini cowboy hats and, uh, you know, getting ready to, uh, to swirl the lasso. Which, by the way, is actually a bit easier than I thought.
[00:19:34] I was a bit worried I'd be really incompetent at the lasso, but it turns out to be, it's kind of a bit more, it's a bit more straightforward.
[00:19:41] Matt Stone: y-you've got a key component of truly becoming a space cowboy nailed. So now you just gotta take the lasso up into space, do that, and that's your next bit.
[00:19:50] Duncan Barrigan: Yeah, I, I guess in the zero gravity it would be, it would be interesting to throw a lasso in zero
[00:19:55] gravity.
[00:19:55] Matt Stone: know, like a boomerang, it wouldn't work as, as designed, but, uh, you know, it [00:20:00] would be interesting nonetheless. Yeah. Um, so you do this thing and, and I, I mean, so did-- what was the attention you got? 'Cause, you know, right now, I mean, I think you and I were talking about it, there's tens of thousands of startups, uh, just in a, you know, in AI.
[00:20:15] So many of the ones now are s- AI related. But to get attention, even if you are really unique, it's still this... It's hard to break through the noise. So what was the impact for you of doing that?
[00:20:30] Duncan Barrigan: Yeah. Yeah, it's, uh, it's become one of those things that kinda feels a bit iconic for us within the company and, and is a thing that we're known for beyond it. Uh, so I think it's been, you know, it's been fantastic to see. Uh, the, the thing you actually see on the wall is The Guardian covering it, where the words are, "Cowboys, lassos and nudity," uh, is the opening.
[00:20:52] Uh, "AI startups turn to stunts for attention in a crowded market" is the name of The Guardian article that they, uh, that they wrote with, uh... And that's the, that's the [00:21:00] cowboy on the horse you can probably make out in the background. So, um, you know, I mean, that, the fact that we have a Guardian article written about us obviously is, is a testament to the, to the success of the stunt, and we, we regularly get people that, "Oh, yeah, I, you know, I, I saw that stunt," or, "I th- You're the guys with the cowboy."
[00:21:15] Um, so I think it's one of those where I, again, I think it's, like, an unfair advantage to be willing to be different and to actually follow through on it with courage, because everything that we do now kinda ties back to a better story and is more memorable than it would be if we were another blue fintech with, uh, you know, normal AI branding.
[00:21:36] Matt Stone: I'm really, really diving into like the, uh, what's really resonating for me is like you mentioning that you have these values and that courage is one of them, and then seeing how you've acted on that. And sort of stating the value creates a decision-making that's more in alignment, and the decision-making reinforces the value, that there's this sort of this loop that you need to continue to do.
[00:21:57] What are the-- First of all, what are the other two values that we [00:22:00] haven't talked about that are part of, that are important to you in the business?
[00:22:04] Duncan Barrigan: Yeah, so the three values, it's-- This is an odd source of inspiration, but this is actually inspired... I'm, for, for my sins, a Philadelphia Eagles fan, and I heard Nick Sirianni saying, "We are tough, detailed, together."
[00:22:18] And he just stopped speaking, and I was like, "I mean, this is wonderful." He's-- You know, most people with their corporate values, I'd still be talking in, uh, you know, in five minutes time about trying to define them a little bit, whereas he just stopped, and I was-- I just had this vision of in an interview with a candidate saying, saying our three and, and just stopping and then waiting for them to expect me to continue speaking.
[00:22:35] But no, I'm, I'm done.
[00:22:36] Matt Stone: the podcast, which is nice, and we'll be done.
[00:22:43] Duncan Barrigan: so we are curious, courageous and relentless
[00:22:49] Matt Stone: Okay. So love that. Curious, courageous, and relentless. We've talked a little bit about courage, which we'll come back to. Uh, where does-- how does the curiosity play out, [00:23:00] um, uh, in the business? What-
[00:23:02] Duncan Barrigan: Yeah. The, the, the, the three of them somewhat align together in a, in a sequence. The reason we say them in that order is 'cause we, we like to think that it's super important, especially in a world like ours, where you're trying to create an AI worker that does a job like a humans have done for, you know, for, for thousands of years.
[00:23:18] You have to make sure that you are extremely open to ways of doing things, extremely, um, curious about why as well as what, so you can simultaneously take the way that it's currently being done and, like, frankly, much more than in many businesses, just do it that way 'cause there's, there's pretty good reasons people do many of these.
[00:23:38] But, you know, have the curiosity to unpack it and explore it and dig in, 'cause there-- it's that fine balance between doing it the way it's been done, but with an AI and, and, and finding better ways. So, um, so yeah, we'd like to start with cura- with the, with the curiosity there, and then obviously the courage comes in terms of the actual decisions you take.
[00:23:56] And the relentness comes in how, how you pursue that and how you, how you go [00:24:00] about and do it. So that's why we think of it as, uh, as the, the-- kind of the curiosity is almost the foundation because you have to make sure that you've got the right options on the table. And if you're not curious enough, there's kind of no opportunity for the rest of the values.
[00:24:13] Matt Stone: But, you know, these values are really important. I find curiosity to be one of the most impactful things, but also one that takes some real sustained, relentless, if you will, intention so that you're not... 'Cause w-- by default, we tend to wanna go with figure things out, right? Which kind of runs against being curious because it's like, look, I need some fixed things here 'cause everything can't be a variable that I'm digging into, right?
[00:24:40] So how do you, how are you as you grow, you've doubled in, at least doubled in size, right? You've-- You're building a team, you're getting more people. What are you learning about your ability to stay and in-infuse curiosity into the culture as you grow that maybe is a surprise to you, or maybe not, but just share some insights about that part of it, [00:25:00] 'cause that's a big part of it, I think.
[00:25:01] Duncan Barrigan: Yeah, it's a really interesting question actually. I think, I think I come at these, you know, at GoCardless I joined when there were about 30 people. I left, uh, having been chief product officer, chief growth officer. I left when there were maybe, maybe it was 900 or something. Uh, so we're still in the bit kind of before, you know, before I began the last journey, and therefore one of the things I try and be conscious of is there's loads of things that I know and have got the battle scars from doing in that scale-up journey from, uh, you know, 30 to 900 beyond.
[00:25:29] And then I'm kind of constantly thinking, is this, you know, what's the right time for some of these to come in? Because the stuff I know from a 500-person company is obviously not always tremendously relevant. And frankly, half of it changes now 'cause- I mean, I don't think a 500-person company will be the same in the age of, the age of AI compared to, you know, what it was, what it was probably 10, five, 10 years ago when, when, when GoCardless was 500.
[00:25:52] So I'm kinda constantly asking myself these questions, and I think how culture scales and how you infuse it is one of those. Kind [00:26:00] of the easiest for me is to, to, to try and embody them and, and be them. And for me personally, I think I'm naturally very curious and pretty relentless. Courageous is the one that I think for everyone just always takes.
[00:26:15] That, that's kind of the, uh, the aspirational one in a way, if you like, 'cause it just always takes-- Well, it takes courage, right? It takes courage to be courageous. Um, so I think, you know, I think, I think the first thing that I do is try and, is try and always role model them. But I don't think that's actually enough.
[00:26:31] I think, I, I think you have to think about the situations where, kind of as you were saying, where they're in conflict with things. Well, how does the curiosity hit the relentlessness? And can you be too curious and not relentless enough, uh, if you, you know, spend too ti- too much time looking at the different options around this and vice versa?
[00:26:48] I think that's the really hard bit where, yeah, I, I'm, I'm not sure I have the answer.
[00:26:54] Matt Stone: Well, 'cause I was wondering, you know, one of the three is not speed, and there's this sort of... I mean, I worked in Silicon Valley years [00:27:00] ago, and I've been around, you know, the cultures where it's like break-- you know, the whole break stuff and just go fast and break stuff kind of thing. Um, I, I wonder from your perspective how, how you balance the need for speed with the sometimes slowing...
[00:27:15] Curiosity can feel like it's slowing you down almost. And so there's this constant tension of like, "I know we're supposed to be curious, but we gotta, we gotta just get it done." How do you manage that, you know? How do you look at it, I guess?
[00:27:27] Duncan Barrigan: And I have, I've seen that balance too. It's kind of-- This is one of the values that's a little bit closer to one we had at GoCardless, where we kind of had that problem of how do you, how do you balance these? I think we, while we say it last, relentless is, is kind of the, the ultimate value for us, and we want ourselves and everyone in it to be incredibly relentless in terms of how we go after it.
[00:27:48] We, we kinda find the word captures a bit more what we mean. It's not like-- Speed is, to me, speed is a scalar and, you know, like velocity is the vector, right? And the, the vector's what [00:28:00] matters and therefore, I think relentlessness for me is also-- It's, it's both about how you're doing it and your response to challenges and your response to it, but it's also more directed and therefore for us, I think relent- We, we have to keep relentless front and center, and we have to make sure, you know, if a candidate to join us isn't relentless enough, then kinda doesn't really matter how curious they are and, you know, how much-- I, I think it ties with courageous sometimes, but, you know, like it d- it doesn't really matter how curious they are if we don't think they're relentless enough.
[00:28:28] So I think that's one of the trade-offs that I've seen go the other way, and I've, I've seen I've seen that as you get much bigger, you kind of end up with a corrupted version of the values and therefore I think the number one thing we need to make sure, and I need to be really clear about, is like it's not enough to be curious unless you bring that relentlessness.
[00:28:47] You know, I don't want someone going off for a week to think about something they could have thought about in an hour in the morning, 'cause they have to be relentless enough to-- Yeah, they should want to go and look at all these areas, but they should constrain themselves and think like, "This is the right amount of time to spend thinking about this," if you [00:29:00] see what I mean.
[00:29:00] So yeah, I think that's probably actually the number one trade-off in our values where we need to make sure that like relentless does trump curious in the right circumstances.
[00:29:10] Matt Stone: Yeah, y-yeah. And, and how do you treat mistakes these days? 'Cause I, I find a lot of people as they mature and they have more experience, they also tend to have a different, more nuanced view of how to deal with making mistakes and how to differentiate between good mistakes and bad mistakes. H-how are you-- How's your perspective on that these days in building this?
[00:29:33] Duncan Barrigan: Yeah, I think I'll start with sort of the, the rationalist version, which is how I think about it in a, you know, for others frankly, and in a, and in a larger, uh, you know, in a larger team. I think the, the-- one of the things that's very different about the founder journey is like your own emotional and, and, you know, psychological journey on it yourself.
[00:29:52] So, you know, we we can come back to my own mistakes, but let, let me tell you how I think about
[00:29:56] Matt Stone: Tell us all of your mistakes, Duncan, just between you and me.[00:30:00]
[00:30:00] Duncan Barrigan: Yeah, I mean, I, I think when it comes to other people that I've always been a firm believer, you know, as a, as a chief growth officer, I think you have to be, that there's a difference between a good mistake and a bad mistake. Uh, I mean, I often for, for people who play any poker, uh, I-- not really much of a poker player myself, but I'm always annoyed by people like, "Oh, I can't believe I folded my three seven off-suit," and then it flops three three sevens.
[00:30:23] You know, I just, I j- I just can't deal with this mentality. It's like, no, you, you have to be able to separate whether it was a good decision at the time from whether it worked out. Those are just two, those are two variables that, like you have to be able to separate to some degree. Uh, and I think it's really important to create a culture where people can experiment and fail.
[00:30:40] But I'd actually say to your question of how it's evolved, I-- The counterargument to that is Napoleon, right? Like, "I want a general who's lucky. I can't, I can't determine whether he's making good or bad decisions on this. All I can judge is the results and therefore, like, you know, I'll take one who's lucky," 'cause it's basically some combination of pure [00:31:00] chance, but also the thing that I can't see and actually makes a big difference.
[00:31:04] So I kind of-- What I probably started a bit too forgiving of them if I thought they were the right decision. I think you have to balance that with-- I mean, look, if someone just keeps having failed experiments, then it's probably 'cause there's something I'm missing about they're not as good as I think they are, you know?
[00:31:22] So I, I, I, I think my evolution has come like reaction against the, you know, the, the, the can't tell Um, 20/20 hindsight from good decisions, but also a little bit of this kind of Napoleon school of like, I want people that make good enough decisions that they appear to be lucky from the outside.
[00:31:40] Matt Stone: Yeah, absolutely. And, you know, sometimes you're in the right neighborhood but in the wrong role in the neighborhood, and sometimes it's, it's just an issue of realigning the, the function that you're doing 'cause it's just not the right fit. I wonder in your life th-thus far, um, you know, can you remember a time when you were really [00:32:00] not in the right space doing what-- space, there I used that word again.
[00:32:04] You weren't in space, Duncan, not yet. Um, you weren't, you know, you, you were misaligned with who you really are. Did-- Have you ever had any experience like that? And if so, how did you deal with it?
[00:32:15] Duncan Barrigan: I think the period from, uh, when I first came to the US is probably the, the closest to that, you know. Uh, I am a very full-on person and wasn't someone who was sat there during my, you know, nearly decade building, building GoCardless constantly thinking about what the next thing would be. So I left without-- You know, I didn't know what Lunos was gonna be when I left, right?
[00:32:36] And then as I said, I made this kind of crazy decision to change all these things at once in my life and, you know, move country, move, go with my girlfriend, quit, et cetera. And it is kind of a-- It shows you what's tied up with your identity and what's not when you go from like a, what was I? A very early 30s, you know, CXO in a couple of billion dollar company that like [00:33:00] kind of, you know, people wanted to speak to me and, uh, you know, I knew loads of people 'cause I was in London, et cetera.
[00:33:06] And then you suddenly like plant yourself on the other side of the world, and then you ki- it, it kinda challenges a bit what you are, right? Because now, now no one, whatever, no one invites you to the Wimbledon quarterfinal in hospitality anymore 'cause they don't care. Uh, you know? So there's so, there's a certain challenge to that, and I think during a period before I, you know, came up with, with Lunos, uh, I think that's probably the closest I've been to something where it's like, "Ah, interesting."
[00:33:31] Matt Stone: When you think a few years down the line, and I'm not talking about an exit in your future or just, you know, that, the, the standard stuff. I'm talking about what kind of organization do you want to be able to look back on and say, "I built that."
[00:33:49] Duncan Barrigan: Great question. I-- you know, it-- an, an organization like Lunos is always... The, the problem's not sexy, [00:34:00] right? And I, you know, I embrace that. I often say it's a, it's a fascinating solution to an extremely boring problem of, uh, you know, this, this-- it's like a $100 trillion niche in a way. So I think that probably, you know, in some form is going to come out in the organization alongside, you know, obviously, you know, my personality, my beliefs and things come out as do those of the early employees.
[00:34:20] So I think, I think that that aspect of it will probably be part of who we are. You know, like we have to be y- you-- I wouldn't say the shadows because that sounds like some kind of spy novel or something, but I think that we have to take pride in being something where ultimately the agent-- what the agent to agent future is gonna do, right, is it's going to increase economic growth, is a very simple way of putting it.
[00:34:44] Businesses fail because they don't have cash flow. They don't actually usually fail 'cause no one likes their products, or most of the time they don't even fail because they're not very good at like creating and selling them. They fail 'cause they're bad at managing cash flow. So we're something that will prevent businesses from failing and [00:35:00] ultimately, especially in this agent to agent version where you start getting agents on both sides, will, you know, ultimately it'll facilitate trade.
[00:35:07] We'll all be richer. We will all, um, be in a faster growing economy. So I'd love the organization to be something that I suppose kind of takes pride and relishes that in the way that I do and isn't like wanting to be some, you know, consumer, uh, you know, some consumer startup that everyone's, you know, necessarily heard of on the street.
[00:35:27] I think there's something where you have to kind of own that and you have to say, "Well, you know what? That's actually much bigger impact than a flash in the pan thing that for six months everyone wants your soft toy." Um, this is something that's much deeper and much more impactful in the world.
[00:35:41] Matt Stone: Yeah, absolutely. And I mean, and businesses are very personal, and they touch people's lives, and they sustain their lives, and raise families, and fund schools and healthcare and everything else. So it's a pretty human story underneath all that accounts, you know, receivables. Um, so yeah. What-- [00:36:00] how is this-- what have you learned about yourself in the last, you know, year or two?
[00:36:06] Duncan Barrigan: Hmm. Yeah, that's, that is an interesting one. I, I, I've learned a lot about myself in the last, uh, in the last couple of years, that's for sure. I don't think anyone can go through the experience of starting a company and not learn a lot about themselves. I kind of-- maybe some people do. If so, I'd be fascinated to hear from you, uh, because I can't really, I can't really comprehend how that could be the case.
[00:36:30] But yeah, I'd love to, I'd love to talk to you. Please reach out.
[00:36:32] Matt Stone: Duncan, I've met a few people who appear not to learn anything about themselves ever, but, uh, that's a, that's another podcast.
[00:36:39] Duncan Barrigan: Yeah, I would say that I have-- I've probably emerged a bit more deeply self-aware. No, you know, I've, I've worked in places throughout my time where people will kinda tell you how it is, you know? I, I started my time in fintech, in, in fintech consulting, where you were literally stack ranked against everyone else [00:37:00] in Europe, and you're th- you know, like, I think these environments give you a sort of superficial self-awareness of what people think of you.
[00:37:07] But I think this has given me a greater awareness of what I think of me and what I'm really good at and less good at, is probably the biggest thing that it's exposed. So yeah, the, the, the self-sense rather than the perception of others.
[00:37:26] Matt Stone: You know, um, I've worked in the self-aweness, aw-aweness? Awareness arena, um, for a while, and, um, it's hard to be self-aware. People are less self-aware than they think they are. And you struck me when I met you as someone who had a level of self-awareness that is not always seen in certain circles, and it, it's-- and I'm not just trying to blow smoke here.
[00:37:49] It's why I asked the question, because you're clearly thinking about it. I'm wondering what you could offer other entrepreneurs, uh, in terms of Your experience in cultivating [00:38:00] self-awareness. How do you cultivate self-awareness?
[00:38:03] Duncan Barrigan: I wouldn't say I have any, you know, particular tricks. I think to some degree, it's something that you, you kind of have to work through and experience. But one-- a, a couple of stories do spring to mind. So one, one is that I think you're constantly walking this tightrope of asking yourself- There's this thing I don't want to do.
[00:38:23] Why do I not want to do it and what does that mean? Some things you don't want to do because you know you really should and you're dreading it, and you definitely should do it and you're the one that should do it and you should just go ahead. Other things you don't wanna do and it just doesn't actually make sense for you to do it and what that's telling you is you should find someone else to do it for you.
[00:38:45] And I think it's a very difficult line between two that you need to figure out. You know? Like, sort of earlier in your career, you know, the first time you actually have to exit someone for poor performance, you're probably on the first side. And if you're not aware of that and you're, you're listening, like I would say do it.
[00:38:59] If [00:39:00] you're thinking about this and you haven't decided to, please just do it 'cause you should and you're just in the first one. But I think doing a startup exposes you to a lot more things where you're on this borderline between the two. You know? As a solo founder, when should you hire someone to work with you on GTM is kind of an absolutely classic question of this genre of, well, it's entirely possible it's on either of those two sides.
[00:39:19] It depends on who you are and where you are and how clear it is that there, there is PMF for this idea. You know? I think the really difficult ones are the ones that are on that line, and I think I've found that those sorts of decisions and how I've approached them have made me better at doing the ones that I should do and just I'm not, but also hopefully a bit more aware of the ones where it, it just does not-- I, I could force myself, but the cost in energy terms and sort of personal, you know, like the, the psychology that I need to, to keep driving the business forward is just not worth it.
[00:39:52] And if it's relatively easy to pay your way around it, then sometimes you should just pay your way around it.
[00:39:58] Matt Stone: Absolutely. Yeah. That's some [00:40:00] real wisdom there too. And, and being, just being able to-- Boy, that GTM, uh, point you just made is like five stars truth right there. Who do I let in to do this? 'Cause it's, uh... Boy, you can go down the wrong path, um, if you give away your idea to somebody else, uh, too far. Um, and those-- the, the discretion and the wisdom that goes behind making those decisions is, is not something to be li- taken lightly.
[00:40:26] All right. In our ma-remaining moments here, really looking forward, c- do you have any, like, exciting things that you can let us in on that we don't know, that- You know, tell me all your secrets, Duncan. What do we have ex- what do you have exciting... I know it's not an exciting-- maybe to some people it's not exciting, but to me, building a company, building a team, growing something is always exciting.
[00:40:49] Like, so what are you excited about, and do you have any announcements to make?
[00:40:53] Duncan Barrigan: Yeah, the thing that I'm most excited about is something that we'll be doing in the next few months, which is, uh, you know, I, [00:41:00] I, I've talked about this agent-to-agent- Network, right? We've started on the receivable side, uh, where, you know, I mean, in, in some regards I've, I've spent a decade there, right? In ter- previously I had a different solution, now I've got this new one and, and, and helping people to get paid.
[00:41:15] But this is a network problem. There's, there's tens of millions of people doing this crazy, mad, uh, you should see the quotes we get. Brain rot is a word that comes up surprisingly often when people describe this work. Um, this brain rot that, uh, that all these people have to do. And we are super excited to be, um, shortly starting work on adding the, the other side of this network, which is the, which is the payable side.
[00:41:38] So, uh, the analogy I always use for this is, you know, at the minute we're kinda giving people a, a driverless car for their receivables, and it's great. Like, you get to sit in it and you can do other things which everyone wants to do rather than the brain rot, and it'll work better than-- you know, it'll drive better than you, and you get to sit in it and whatever, watch TV, in this case run your business.
[00:41:57] Um, but the magic really comes when everyone else is in a [00:42:00] driverless car too, because then the driverless cars can drive closer to each other and get to their destinations faster and reduce traffic. In our world, that's what happens when you start having agents on both sides, because you go from everything happening at the speed of one human emailing the other human who, you know, may be in a different time zone and asleep, may take ages to get back to you and look at this.
[00:42:20] To the whole world of this, this $100 trillion happening at the speed of agents where you can have these situations where there's five businesses trading and, you know, one of them is in a position to be able to, uh, pay the invoice early and, you know, one business three businesses away is actually the one that's desperately in need of cash flow and all of this is suddenly possible to connect together.
[00:42:42] So I'm super excited about the, you know, the creation of this, this network where you start having agent-to-agent interaction and your, you know, ev- everything starts being a driverless car around you rather than just, uh, sitting in your, in your single driverless car enjoying the fact that you're not driving and it's working better.[00:43:00]
[00:43:00] Matt Stone: just, you just reminded me of something that like, oh, you know, you can hear the sounds of New York City in the background and the cars honking and stuff. That, at some point, is probably gonna go away. You're not gonna need honking if you've got, uh, if you've got AI running
[00:43:13] Duncan Barrigan: That's gonna be really nice.
[00:43:15] Matt Stone: Yeah. Yeah. We
[00:43:16] Duncan Barrigan: Anyone who's ever been to India also knows that that's gonna be really nice.
[00:43:20] Matt Stone: Absolutely, one hundred percent. Uh, let's finish with this. Look, a guy like you, a man like you is always doing the next personal challenge. So, um, what, what do you have personally? What i- what is your next aspirational personal challenge that you're taking on?
[00:43:36] Duncan Barrigan: Uh, yeah, I have collected, uh, licenses for things, I suppose is one way of putting it. You know, I got my skydiving license when I was 18 one summer. My friends from school went to Ayia Napa or somewhere and I went to Nottingham to do my, uh, my, my skydiving course instead. And since then, yeah, as you... Uh, and instead, you know, that of, you know, scuba [00:44:00] diving and sailing and, uh, the, the, the latest that I, I've picked up since coming to America is, is flying very little planes, which I hasten to add, you know, uh, given I am an early-stage founder still, they're currently very small planes.
[00:44:12] Uh, I would like them to be bigger planes and faster planes. That requires, you know, Lunos to be successful, so please, finance people listening, come, uh, come talk to me about Lunos. Uh, but I think that for me, I really wanna get to the point where, uh, I can kind of fly something really exciting. You know, I wanna get to the point where I can do some of the, uh, the, the aerobatics in particular.
[00:44:34] I hope-- my girlfriend may listen to this or may not, and may not approve of this, but I really would like to get to the point where I can do, like, a barrel roll in a plane. I think that would just be-- I'd feel like I was a fighter pilot at that point.
[00:44:45] Matt Stone: I think, uh, we need to make an introduction to Tom Cruise at some point. Um, no, But that's, that's really cool. And I, and, uh, gosh, I don't know that I... I don't... Flying just-- I like to be in a, in a large jet, but the small [00:45:00] planes kind of scare me,
[00:45:01] Duncan Barrigan: There was actually, there was-- So I was once, um, I was once traveling in, in South America, and there was a little plane that went from, I think it was from La Paz down to the jungle. Uh, and the flight before me, the people I met, it was like a eight-person plane or something, and it basically takes off at, like, 5,000 meters and just lands at sea level.
[00:45:20] So it just flies down is all it does for about half an hour. Uh, and the people on the flight before me, the plane had fallen out of the sky for about 45 seconds. And what I found fascinating as I met these people in, you know, sort of the, the bar of the only hostel there, was that half of them thought this was the coolest thing that had ever happened to them.
[00:45:39] Uh, and the other half were absolutely terrified and somewhat traumatized by it. And you just, there was no reconcile- you know, you just couldn't reconcile between the two. And I, I know that as long as I survived it, I just knew as I spoke to them that I would think, "Oh my God, that's so cool. I got to fall out of the sky for 45 seconds like an action movie."
[00:45:56] And then here I am in a bar drinking, telling you about it. But I just thought it was, it [00:46:00] was one of those, like, people just divide into two mutually unintelligible halves on that, on that question.
[00:46:06] Matt Stone: Well, I tell you what, not getting paid can feel like you're falling out of the sky and gonna crash, and you're giving some order to that. So let's finish with this. Business owner is listening to this, um H-who should work with you? Who's-- Do you have a too small of an organization number? What size organizations can you help, and who should reach out to you right now?
[00:46:29] Duncan Barrigan: Yeah, absolutely. So I think the, the minimum size is when it's really annoying for you. You know, we have people with tens of thousands of invoices a month. We have people with tens, but it's just really annoying to them. So, um, you know, if you're annoyed by it and you're annoyed enough to do something about it, you are not too small.
[00:46:45] Um, in particular, we love, you know, we do love talking to, uh, to, to, to larger businesses that are, you know, dealing with scaling problems. Uh, but really it's anyone who is in this world of B2B invoicing is annoyed by how much work it is [00:47:00] taking them and their team to get paid and how fast they're getting paid.
[00:47:03] And small caveat uses, uh, at least semi-popular online software to do so, so that we can connect to your data and you can plug and play and get started in, you know, in hours rather than anything else. So yeah, if you're annoyed by it or you know your finance team is annoyed by it, then, uh, you know, check us out at Lunos.ai and we'd, uh, we'd love to talk to you.
[00:47:23] Matt Stone: Oh my goodness. Well, I hope some people do reach out after watching this. Duncan, I've really enjoyed this conversation. Thank you for coming to The Bigger Stage, and I'm really looking forward to our next conversation.
[00:47:33] Duncan Barrigan: Thank you so much. I had a, I had a wonderful time too.
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