Paysquad: Buy Now, Pay Together

Josh: Welcome to The Pitch, where startup founders raise millions and listeners can invest. I’m Josh Muccio.

Lisa: And I’m Lisa Muccio. And on the show today we have Cam with Paysquad. He’s raising 1.5 million dollars.

Josh: All right. I'm gonna say the name, you have to guess what it is. Paysquad.

Lisa: Ooh, a squad that pays together.

Josh: You cheated. You know that that's the answer.

Lisa: [deep sigh]

Josh: Okay, yeah, so money. Let's talk about money. Specifically, a little button at checkout-

Lisa: Yes

Josh: called Buy Now, Pay Later.

Lisa: Oh, yeah.

Josh: What if there was a button there where you could pay with your buddies? Buy now pay together?

Lisa: But I could just be like, "Hey, I paid for this. Everyone Venmo me." And then what happens? Half the people don't send you the money, and you're stuck footing the bill.

Josh: Always.

Lisa: Like trying to go see the Goo Goo Dolls with my brother Cody, and I'm like, "Hey, buy those tickets." I think he still hasn't bought those tickets.

Josh: I have to confess something, Lisa.

Lisa: What?

Josh: I don't really like the Goo Goo Dolls.

Lisa: What?

Josh: I don't know.

Lisa: You don't wanna go to the... Fine, then I'll go without you. No, I will go. It'll be just me and Cody.

Josh: No, no,

Lisa: I'm going. Me and Cody. No, you're not invited anymore.

Josh: I will go to support you.

Lisa: You don't like the Goo Goo Dolls?

Josh: I just never-

Lisa: Who doesn't like the Goo Goo Dolls?

Josh: I grew up not listening to them. I want to like them.

Lisa: You're not in the squad anymore. I'm kicking you out.

Josh: Well. The question is, does the world really need another button at checkout? Or is Venmo enough?

Lisa: The Pitch for Paysquad is coming up after this.

Josh: But first… we are hosting two live events this season. One in SF, coming up at SF Tech Week. And another one in November in NYC.

Lisa: We’re also hosting our next taping of season 17 in San Francisco. Join us at any of these events. Go to pitch.show/events

BREAK

Welcome back to the pitch for Paysquad. Let’s meet the investors.

Elizabeth Yin with Hustle Fund

My best deals have been the ones that I've committed on the spot

Charles Hudson with Precursor Ventures

We have 500 companies, so, you pick it, we have it

Mike Ma with Sidecut Ventures

I got strings, I’m not an easy yes

Jesse Middleton with Flybridge

I am so sick of people that are building stuff for building stuff's sake.

And a new investor to the show, Yasmin Cruz Ferrine with Visible Hands

it's one thing to be the first, but then there will be fast followers

Charles: The pitch, day two, pitch one. [clap]

Josh: Ow. Perfect.

Elizabeth: That's how it's done.

Cam: How we doing?

Jesse: Howdy.

Cam: Morning.

Charles: Morning. Hey, Charles.

Cam: Cam.

Charles: Nice to meet you, Cam.

Yasmin: Yasmin.

Cam: Yasmin, lovely.

Jesse: Hey. Jesse.

Cam: Nice to meet you.

Jesse: Hey

Elizabeth: Elizabeth.

Cam: Lovely to meet you.

Elizabeth: Nice to meet you.

Mike: Mike

Cam: Mike, great to meet you.

Cam: Fantastic. Kia ora. I'm Cam Richardson, founder of PaySquad. Quick story. At my 21st party, my friends rolled out a three-wheeled motorbike as my gift. I was like, "Fellas, how did you do this?" They said, "Cam, everybody at the party chipped in to get this for you." Now, to some people, that's a nice memory. To me, it was a paradigm shift where I realized how much more is possible when people do things together, and I had to see it happen more. The problem is, every time since then, whether we were buying a group gift or traveling together or buying tickets to a game and actually wanting to sit together, it was the same pain. One person, usually me, had to front the whole cost and then chase people to pay me back one by one. It was awkward, slow, and it strains relationships. The world is designed for solo shopping, so when you hit checkout, you're gonna see a pay now option, you might see a pay later option, but you're almost never gonna see a pay together option, despite the fact that 30% of Gen Z like myself share the cost for something every day. So we built PaySquad to make group payments native at checkout. It's the first buy now, pay together.

Here's how it works. One person selects PaySquad at checkout, we call them the squad leader, and generate them a link that they can share with friends, family, and colleagues on any messaging app in any group chat, anywhere in the world. When they click the link, they can see who started the pay squad, what it's for, who's already contributed, and how close they are to the target with no need to download an app and no need to chase your friends to pay you back. When you hit 100%, that order is automatically processed. But the magic is on the other side, too. Merchants want PaySquad at their checkout because we're seeing triple the average order value and five to seven times the reach than any other payment method. In one sale, a merchant could acquire 10 new customers. That's transformational. So far, we've launched as, a global payment partner on Shopify, the first pay with friends option. We've onboarded seventy million dollars in merchant GMV, and we have another billion going online in the next month. Today, we're raising 1.5 million to build the future of multiplayer commerce and help more people experience what I did at my 21st, the power of groups doing things together.

Elizabeth: How are you getting these merchants in these early innings?

Cam: Sure. To date, we've raised, 80k, as a friends and family round, and so, you know, there hasn't been any huge marketing campaigns or anything for merchants. It's been, sheer audacity, inbound requests, people finding us on ChatGPT and on Google Search. Classic example of this is a company called Totem, and they have these little friend-finding compasses, at festivals. And they were like, "Man, we've got these big bundles. Obviously, friends buy them all together. We need to have a pay together option, if there is one." so they gave us a call, and we integrated with them inside forty minutes. In the two conferences that we've been to, we're the really novel new tech. And, we have certain categories that we've already seen that are, like, running up to us being like, "Hey, I've been, like, waiting for this to exist.”

Mike: Can you walk me through the unit economics?

Cam: Sure thing. So similar to buy now, pay later, we charge a commission fee for every successful sale, typically in the realm of about four percent, which when merchants compare that to what they're paying for BNPL, it's quite an easy sell. We have a higher net transaction margin because we're not forming a line of credit or anything. So we right now are seeing a net transaction margin of about two point two percent. At scale, that could be well over three percent.

Yasmin: How are you thinking about the competition? 'Cause it's one thing to be the first, but then there will be fast followers

Cam: So in terms of moats, we typically see, brand, data and integration complexities as our main moats. And for fast followers, I think the integration complexities are probably the highest up. Shopify, for example, is an invite-only, global payment partnership. With every merchant that we sign a deal with as well, we have an exclusivity, that they can't develop their own, group payment, option or, sign on with a competitor as well. and look, you know, large, particularly enterprise merchants, they're not gonna sign up to, something that was vibe coded, a couple, couple weeks ago. I think FinTech still has a little bit of that technical barrier unlike other industries right now.

Jesse: what was your background before this or your founding team? Were you guys in the payment space, merchant, e-commerce?

Cam: For sure. So I was in omni-channel retail. I'm a two-time founder. previously I was part of a team that, bootstrapped a billing platform to process hundreds of millions of dollars. we built the foundation of PaySquad and then spun it out. And went full-time eight months ago to, to pursue this. I've now brought on some exceptional talent, particularly, Sam Schaefer in New York, who is was the first employee at Afterpay US. did the blue chip deals with Macy's and Urban Outfitters, and then another ex-Afterpay, person in Melbourne who will be leading our, customer success retail experience and then my, head of growth and, product, Joel, who is a ex e-commerce founder, right up to date with the latest in, AI development and, story branding.

Charles: Are there any, product category types that this doesn't work for?

Cam: One of the ones I'll share that we thought would work but hasn't really proven to be too valuable yet is furniture. We're like, Okay, cool. Fits the idea of a high average order value, maybe for housewarmings and things. it turns out that people have very specific taste when it comes to ... comes to those and even in the, the premium brands, they really like- protect their, like, one customer that they're building a, a relationship with. it might be one we add later on, you know, when it becomes far, far more mainstream, but for right now that was a surprise.

Charles: And what about things like perishable inventory, like airline tickets, concert tickets, fes- things where, like, there is some time sensitivity between when you put it in the basket and when you check out?

Cam: So in those situations we have a configurable timeframe right now. So for an online travel agent we signed up out of Singapore, we give them 50 minutes. And because PaySquad's so seamless, that 50 minutes sometimes gets done in five minutes. In the future, we're gonna have the first person effectively underwrite the full amount, and we'll come in and help them do that so we can guarantee the sale straight away. when people start a PaySquad, a group payment, they are fully committed to getting that thing done. We have a success rate of, like, over 90%, and so we're like, well, we might as well just be able to front it

Elizabeth: So if I heard you correctly, you've powered over 70 million GMV, and if you're taking a net of 4%, you've done 2.4 million in revenue in the last eight months?

Cam: Merchant GMV, so the size-

Elizabeth: Ah.

Cam: Yeah, as, as size- of stores that we're, we're serving. Yeah.

Mike: I was like-

Elizabeth: Oh, oh, okay ... This is not... Okay ...

Mike: This coming into bps, right?

Elizabeth: I see. So, so I guess, like, how many transactions have you powered since you started?

Cam: Yeah, so we've seen $4 million in PaySquads created. and on that we have a, a variable rate of, percentages. So, in May we're, looking to do 20,000 in revenue, and predicting the next 12 months to do 2 million to 3 million.

Mike: recovering banking and payments person here. Like- ... so you, you have a lot of people who are from the industry, Afterpay, et cetera, and yourself. So how do you beat this race to the bottom, that pervades the space- ... from one payment person to another? Like, what is insight on the growth that your team has, and how are you executing against this?

Cam: I think the difference of ours is that we have far less payment risk in each transaction than if we were underwriting it in a credit perspective or in some debt funding. And so for us it is actually moving laterally into more of the communication coordination that comes uniquely with group payments. Being viral from day one is super, super helpful for us. Afterpay was really famous for signing up a million customers and spending less than a million dollars on marketing. For PaySquad, we have the K factor of, like, an early 2000s social network. You know, in one sale, we're seeing between five to seven people pulled in by the squad leader. and people are putting us up on their product description page. So it's about catching fire early, and then being able to build sector-specific integrations and really expand what's possible. Yeah.

Mike: Can you say more about those sector... Like, so we heard it's not furniture.

Cam: Yeah.

Mike: So

Cam: What is it?

Mike: What are the sect- yeah.

Cam: So the two main categories that have really risen to the top in this early stage have come from baby, um, baby goods.

Elizabeth: Mm-hmm.

Cam: One classic example of this is Cradlewise, based out of, California. They have a $1,700, bassinet cradle. On their product description page, next to Klarna, next to Affirm, there's pay with friends and family using PaySquad. and we're seeing, really great high-value conversions through that. we've got a $520 million retailer as part of our onboarding in the next month that is in the baby space and another $200 million one that we're bringing on, just shortly after that. So, huge space for us. But the second one that is going to be even bigger is actually pro sports ticketing. The team and the platform are getting everybody's contact. They're making a connection-

Elizabeth: Mhm

Cam: with everybody, not just the person who's made the initial payment. And that is really, really valuable for connecting with fans and even for the ticketing platform as well. But it doesn't end there. There are also really large groups, like 50 plus, that are booking tickets for places, and I've seen behind the curtain, and it is the most manual process I've ever seen. Diabolical to see in 2026. And, by bringing that into a fresh, UI on the front end so that people can, coordinate without having to get on the phone, which Gen Z hates to do, uh- ... and, um, and organize it that way, will be utterly transformational for them, not to mention the opportunities that we have to upsell, memberships, like season memberships, have never entered sort of the gifting equation, and that, I think, is a great travesty. And then, group merch as well, so, buying team kit together.

Elizabeth: So my feeling is that this, this idea is not new. There have been lots of people who have tried this, and I think there are a number of issues, certainly this idea of differentiation commoditization. But I think even just the sheer act of doing all this business development with all these sites, the holy grail is getting essentially the really big sites, the Airbnbs-

Cam: Yes

Elizabeth: et cetera.

Cam: Yes.

Elizabeth: and no one's really cracked that nut because, like, those folks are powerful. This is not a priority for them, et cetera. Like, how do you plan to do that?

Cam: Hmm. Yeah, Airbnb has an interesting history with this. They acquired a company that was, doing something in the space. I would say that virtually every merchant we talk to has never considered or been pitched a pay-together option at checkout. So from what we've seen in the market and all the competitors we've tracked, it's incredibly novel. We've become the, the group layer for social commerce, and I think that's an area that hasn't really been innovated in the last decade.

Mike: Can, you go back, you mentioned, an exclusivity in your arrangements I just wanted to see what the extent and range of this exclusivity that you've built in.

Cam: if, presented with another, group payment option or something that, has collaborative payments right there at the checkout, our merchant service agreement restricts them from being able to, integrate with them.

Mike: But they could just terminate your MSA, right?

Cam: They could.

Mike: Okay.

I hate it when that happens. We’ll be right back.

Jesse: can you go back in the same vein around integration complexities? I'm curious if you can double-click on this, 'cause the buy now, pay laters, where they're offering credit, things like that, there's an underwriting of the consumer, but also of the business, fraud, all of these things. Where do you play in that? and where is sort of the risk for you in integration?

Cam: For sure. Right now it's quite platform specific. We know that the most innovative, retail merchants are on Shopify. That's why we got on Shopify. So if there is a merchant that wants to integrate with us on Shopify, we can get them live in under 20 minutes.

Jesse: And you're not taking on any risk in that? Like, your payment processor is still taking on The fraud risk, things like that, so you're not having to deal with any of that.

Cam: That's right.

Jesse: Okay.

Cam: And we have a sophisticated, like, payment orchestration layer underneath it. The second, like, great enabler, and to be honest, a lot of this has been buy now, pay later rolling out a red carpet for us, is in payment orchestration, which is an emerging place globally that helps enterprise merchants be able to, effectively handle all of their alternative payment methods

Jesse: Mm-hmm

Cam: in one thing, so that they're not stuck in Stripe, they're not stuck in Adyen. They can actually play around to the best option. We're, as part of our, our baby brand, the $520 million one, as part of that integration, we're integrating with their payment orchestrator, and that actually opens the door for us to be as easy to switch on, as Shopify in some of the biggest brands in the world. Hotel chains that you know, live event platforms that you know as well. And that, for us, has been a great enabler, because they're incentivized to sell us to their customers and to their partners as well.

Elizabeth: Double-click on this large baby brand for a moment. How did you land them?

Cam: We're six days away from starting the integration. and we have about a week and a half in terms of the time that we're expecting the integration to take. That's because we're integrating with the payment orchestrator and giving us opportunity to that, that whole other realm.

Elizabeth: But I mean, how did you get them? what does the contract kind of look like in terms of the economics, et cetera?

Cam: For sure. So, it was a chance connection that I made on LinkedIn. Because they, do about 70% of the baby market where they are they have asked us to sign exclusivity with them, so we can't sign up any other baby brands, and that's gonna last for 12 months, and then will be extended to 18 months if we hit a run rate of like, a million, in that first few months.

Elizabeth: is this what you're taking 4% on?

Cam: in this particular case, 2.8%. that's one of those levers that we have, the go-to-market motion that we can create around huge brands is really, really powerful, and this was worth taking that, cut on. You hear all these stories that you've probably heard, like, about, buy now, pay later, just coming in and dropping, like, a million dollars to get onto a certain checkout because they know the marketing power of being there.

Mike: I could see a wedge in this idea of the social commerce platform. And I was at Betterment, and we launched, Betterment Gifts as part of registry. The problem is they're one time.

Cam: Yeah.

Mike: Right? So reconcile for me, baby brand, it's not like travel or restaurants where there's a high volume. So-

Cam: Yes.

Jesse: Two and a half times.

Cam: And decreasing.

Jesse: And decreasing.

Mike: Oh, sorry. I, I- And listen, I'm, I'm on the empty nesting aspect- so I'm done. I, I’m, but my point is, like, you need transaction volume, right? You need repetition to build this.

Cam: Yes.

Mike: So reconcile this moat for me-

Cam: Sure ...

Mike: against your wedge market is baby-

Cam: Yes

Mike: and then also, by the way, exclusive. you have one and done in this area. So how do you, do you go to market in a way that you can actually leverage your feasible moat?

Cam: To be clear, the, the one and done is in the Australian market, so that's where the 70%, of the total-

Mike: Okay

Cam: industry is. So wide open-

Mike: Gotcha

Cam: in the US, nice and easy. right now it was like we need to find the highest, , interest, for these wedge points, but we at all times keep the TAM as that 30% of Gen Z that share the cost for something every day. That starts by creating these flywheels in baby, in ticketing, in travel, and then being able to say, Hey, now that we've got contact with these customers, and merchants, what are the other things that you're wanting to share the cost for? How can we move into that? What does utility bill look like, for PaySquad? Is this valuable to electricity companies to have multiple people on file? When one person leaves the house, can we then swap them out for someone else? There's just unique product formulations that haven't really been tried yet, now that uh the technical side of things is far easier than ever before. We can move into all of these really nascent industries and begin to bring a multiplayer, aspect to it. And the opportunity for that from a, a, even a viral, coefficient is enormous.

Mike: Yeah. I'm gonna say I'm, I'm gonna pass. just having spent my life in this area.

Cam: Yeah

Mike: I think your competition risk is, is so high. if I offered you one piece of solid advice, of everything you mentioned, I could see travel being a wedge market where you can kind of own that, you're looking for this hard sweet spot between high enough ticket value where you need share, and high enough transaction volume where you could build your social moat-

Cam: Cool

Mike: and then that can move into other industries. , but that'd be where I would make a, a recommendation for you.

Cam: Cool.

Mike: I love the fact you have an exclusive in your MSA, but it's really simple. It's like, like happened every day in the payment things just to cancel your MSA and move on.

Cam: Yeah. Thanks. That's fine.

Charles: I got to the same conclusion, but for maybe a different reason, so I'm also, not gonna move forward. We've done a handful of things in payments. One we have that's doing quite well is in the HSA/FSA payments. And my big takeaway is payments a, you need a very big top-line number flowing through the system such that when you get through all of the cuts and slices that everybody else takes, there's enough for you, and I think this is a useful use case. Like, Mike, I think travel is probably the place, but I just worry there's not enough total addressable transaction processing volume for group payments to make a really big business.

Cam: Cool. No, thank you.

Elizabeth: And I think building on that, so a, a slightly different lens. Almost two decades ago now, I started a social commerce site, and we were trying to do BD with a lot of different retailers. Now, I realize the world has changed a lot in the last two decades. But I think one of my learnings from that is you have to be a pretty high priority for them. And so if you just kinda start to take big markets and whittle it down, like, okay, maybe 10% of the transactions, if we're generous, go through this group thing, and then, like, whittle it down even more on your take, et cetera. Like, for even this large customer, the 500 million GMV customer, A, they're hard to get, and you're gonna need, like, at least 100 of them to build a big business. And the BD cycles on this for most of them are really just quite hard to even get on their radar because they have so many other priorities just keeping the ship afloat, so-

Cam: For sure.

Elizabeth: unfortunately for me, I, think I'm out.

Cam: Cool.

Elizabeth: Thank you.

Jesse: And yeah, unfortunately I had fallen on the same thing. I think one of the things I think about is the economic driver. So one of the reasons that buy now, pay later does work in the way it does is there's a lot of room to add margin to this thing. There's a race to the bottom on price, but there's a

Cam: Lending

Jesse: offering credit, lending, right? You have room, you can offer it to less credit worthy, and you can charge a higher rate.

Cam: Sure.

Jesse: I think you're going to have to get into doing that. It sounds like you're thinking about that already 'cause you're thinking about the, like, underwriting the single buyer. Right now you have this huge risk that, like, you're already offering them a much lower rate, and so your net take is gonna be very small. So to Charles' point, even more volume necessary. And so I think that's the challenge, I think you're just early in this. Its, I do find it to be a creative wedge. I don't know how hard it would be for a firm or anybody else to say, you know, We're gonna offer it and cancel our MSA. But assuming you can figure that out, which maybe you can, the rest of the business has to flow in that way, and it's just, it's, it's just early.

Cam: For sure.

Jesse: So for that, I'm, I'm out.

Cam: Cool. Thank you.

Yasmin: I'm also gonna pass. It was great to hear your pitch. It's a great team you're already attracting, and I'm excited to watch you build, and the network effect is really interesting. But from the moat perspective, I'm out.

Cam:

Cam: No, I appreciate that, everybody. Thank you. 

Charles: Thank you very much.

Elizabeth: Yeah, thank you

Charles: Thanks Cam

[applause]

Jesse: Yeah. One of the interesting things, and you talked about it a little, but he said it in the numbers, like, they're, even before this large customer, they did 20,000 in revenue, and it was, like, half a percent take rate, right? Not even the 2.2, not even the 1.2, like, it's ve- And that's- that's without the highly negotiated deal that's coming in, that my math says it's basically 0% net take.

Mike: There's something that comes in, in founder pitch too, like, if you're gonna sell a payments business, like you're in bps. You're not in percents.

Josh: Yeah.

Mike: Right? Like, he, almost lost me out, out the jump, right? And, and this-

Josh: Wait, say more. I'm not quite following.

Mike: So, so the payments, when he was talking about, you know-

Jesse: 4%

Mike: there's 4% take right on a 70 GMV.

Yasmin: 400 bips.

Mike: I was just like, if you work in this space it's not credible. And he led Elizabeth down the rabbit hole. It was, like, two point. It was like-

Elizabeth: You're doing $2 million in revenue?

Mike: I was like- Yeah ... I was like, No, no. No, he's not. Right?

Josh: But don't you think that's an honest mistake?

Mike: No. I mean, if it is, then it's a mark.

Elizabeth: I, I think it was an honest mistake. And that's why I asked the question.

Jesse: Yeah, I mean, he-

Elizabeth: To clarify.

Jesse: he called it merchant transaction volume.

Elizabeth: I, I-

Jesse: And so I, like, I think it could be, it could be construed that.

Elizabeth: I don't think he was trying to mislead me.

Jesse: Yeah. Yeah.

Elizabeth: I don't jump to that conclusion.

Jesse: No, but I, but I think your point, though, would be that this business is a business that is measured in, in basis points, and that-

Mike: It’s a payments company. Yeah.

Jesse: the margins are very tiny. Like, every payments company, like, if you could make 4%, like, that would be like a-

Mike: And maybe I'm just like, grizzled, grizzled, like, fintech person, which-

Josh: I think you are, yeah.

Mike: I definitely am.

Josh: I get that sense, yeah.

Jesse: Mike has lived so many lives as an entrepreneur.

Elizabeth: Yeah.

Yasmin: Snowboarding

Mike: No, I mean, yeah. I, I am unhireable.

Jesse: Unhireable. Yeah, this is, that's fair.

Mike: The worry is, you spent our capital to make a market for a firm to sit on, right?

Jesse: Yeah.

Mike: Like, that's not fun.

Elizabeth: For me, it was less about that, 'cause yes, that's the nature of fintech, but more about the timing of why now, and for him to come out of the gates and say, This has not been done before, like- it has been done before, it's just, no one has survived.

Jesse: Yeah.

Elizabeth: So I think you have to explain, like, why now is better than when all these other people tried it, and it's because of A, B, and C reasons. And I didn't quite hear that.

Yasmin: Yeah. The baby space is also really tough.

Jesse: Mm-hmm.

Yasmin: And every at bat in the baby space, for me, has gone so wrong.

Josh: Mm-hmm.

Mike: It, it's also, .. a big one-time purchase-

Yasmin: Yeah

Mike: right? Like, it's not-

Yasmin: And the network effect-

Mike: taking a trip every year

Yasmin: is not the same.

Josh: Yeah.

Elizabeth: Well, but if you are a button integrated on a site, you are there for all the recurring customers for that site. It's just getting your button on the site is hard.

Josh: Yeah.

Jesse: And staying there.

Elizabeth: And staying there.

Jesse: That's, like, that's the challenge, right? A lot of these merchants, even the larger ones, will try things out on 5% of their traf- you know, there's like testing that people are doing.

Elizabeth: Right, right.

Jesse: It’s so easy because you have a payment orchestrator.

Elizabeth: They don't roll it out to everybody.

Jesse: When you have a payment orchestrator platform, to his point, so you're like, turn it on right now. Try it.

Elizabeth: Turn it off.

Jesse: Turn it off. There's... I was thinking about the checkout I just went through yesterday, and there were, like, seven different payment buttons, and this was like a large site. And it was, like, three different buy now, pay laters. I was like, I, I don't even know-

Elizabeth: Wow

Jesse: -why they're on there. Like, I'm not sure what the difference is, but I think it's just, like, logo recognition. Like, you're gonna be the eighth one that may be on there for 10%. Like, I don't think he was being misleading, but I also think it's, it's the way-

Mike: Being optimistic

Jesse: he described the business. I think it was o- way overly optimistic.

Mike: Yeah. That-

Jesse: If you knew the payments business, you would know that's not how this is gonna play out.

Josh: Mm-hmm.

Jesse: Like, you're gonna measure in percentages of percentages.

Mike: The payments business is not an optimistic area of fintech. It's not.

Elizabeth: You have to be cynical like Mike to be running one of those. Is that what you're saying?

Mike: And, and, and here's the thing, he has Afterpay, he has industry execs working.

Yasmin: Right.

Elizabeth: Yeah.

Mike: Like, Come on, bro. Like...

Elizabeth: Well, I mean, you have to come into a pitch all sunny and excited.

Mike: I, I, I do. I, but, like... I don't know.

Jesse: Well, you don't, but he has to.

Elizabeth: You don't, but he has to.

Mike: There is a frame of reference that has to be, in bounds, right?

Elizabeth: I, I guess I'm just saying that I think that is more in the category of naive rather than misleading. I don't feel like he tried to lie to me or what... Like-

Jesse: Yeah

Mike: I just, like, generally give people the benefit of the doubt.

Charles: I think payments is not a business for the naive.

Elizabeth: So, so that, that's fair. And that-

Mike: Especially with- especially with Afterpay execs and, like-

Charles: Yeah

Mike: And, and he's like, these are not, like... I don't know.

Elizabeth: So, so-

Charles: As Mike knows, you're not really a successful payments company till somebody rips you off. Like, you haven't made it-

Yasmin: Yeah.

Charles: You haven't made it until somebody really hits you hard with fraud ...

Mike: Look, tacit biggy shot[????] right?

Charles: So-

Elizabeth: So that's fair, but you don't have to invest, right?

Josh: If he would come in, really focused on travel or some other market that feels less problematic than baby, like, is that more interesting?

Elizabeth: I, I think about things, like, from the founder perspective, having been a founder for a long time. So if I were tackling this, what would I do? Well, we would have to cold email or cold call a bunch of companies, right?

Josh: Mm-hmm.

Elizabeth: And so we, let's just start listing them off, right? In travel, there's probably five companies. It's probably, like, Airbnb, Bookings.com, Expedia, whatever. And Expedia and Bookings.com are the same company.

Josh: Yeah.

Elizabeth: So, it's not that many companies that would actually make an impact, and that is the key here, right? You can get all the little Shopify sites, but they will not make a dent in your revenue. He has this one big player who maybe might give him a million a year, which would be great, but now we have to go and find like 100 more. So I think it's like all the categories he listed off, there's probably a handful in each of those. It may even be less. and then what's your likelihood of landing those? And I think that likelihood is, is pretty small, and that's kinda how I think about it. And so, I don't know, if I were to put a pin in it, like could he get another handful of sites? Yeah, probably, So maybe this is a 10 million a year company.

Josh: Mm-hmm. So even though he's coming in with being able to say like, "We are already increasing average order value through these companies," like that's not interesting enough.

Elizabeth: Well, and I also am not sure I necessarily believe that.

Charles: Yeah.

Elizabeth: Like that's very hard to prove, and I actually think that is probably the problem with why is it so hard to do BD. I don't know if stores believe that. Like you're still gonna buy-

Charles: Like we have-

Elizabeth: with your friends even if it's hard.

Jesse: Yeah.

Charles: the HSA FSA company we have, they have like a very clear story around lift.

Elizabeth: Right.

Charles: And they're, actually, their biggest... The merchants are just like, Well, what if this is just cannibalization? Like, What if we just take a transaction that would've gone through our normal rails and then-

Yasmin: Right.

Jesse: I have to pay you more.

Charles: But they're just like, Oh, these are net new customers to us. And it's a more comp-

Mike: Yeah

Charles: but there's actually real complicated stuff on the back end.

Mike: There's real friction-

Charles: There's real friction

Make: in the HSA, FSA space.

Charles: Yep. Yep

Mike: Right? Like, ranging from regulatory just like cognitive overload-

Charles: Yep

Mike: of understanding it and then-

Charles: Mixed baskets. There's a whole bunch of problems.

Josh: I mean, so it sounds like you guys just don't even fundamentally believe that this is a problem.

Charles: I don’t think this is a problem.

Mike: I do think it's a problem. I think it, my worry is like it's a problem he solves, and another firm's like, "Cool."

Yasmin: It's not a problem in the baby space, that's clear.

Charles: I just don't think it's that clear cut

Josh: 'Cause they have registries?

Yasmin: Yeah. And Amazon, you sh- everyone, it's all shipped to your house.

Jesse: Yeah.

Josh: Yeah.

Yasmin: I just had a baby shower. Nine months ago.

Mike: Heyyyy

Charles: I think sometimes you have to be honest about like what the substitutes here are.

Elizabeth: Yeah.

Charles: The high friction costs of like one person does it all.

Elizabeth: Yeah.

Charles: Which still happens a lot.

Jesse: Which is mostly what happens.

Josh: Yep.

Charles: Vendor, vendor solutions like Splitwise

Yasmin: Splitwise.

Elizabeth: Mm-hmm.

Josh: Okay.

Charles: All right. Thank you, sir.

Josh: That's pitch one.

Jesse: All right.

Elizabeth: Thank you

Cam walked out of the pitch room with no commitments from this squad. But this was just stop number one on his American Tour. What happened after the pitch, after this.

BREAK

Welcome back. A couple months after his pitch, we caught up with our favorite and first ever kiwi on the show.

Lisa: Hi, Cam

Cam: Hey

Josh: Welcome back to the show.

Cam: It's good to be back.

Lisa: So you came all the way from New Zealand to be on The Pitch. Which is insane. That is 8,000 miles to travel. Are you crazy?

Cam: Beyond. I mean, look, my adoring fans describe me as delusional. [laughter] Talking about my mother there. Uh, look, it, it was, uh in the startup world, you've got to take big swings and risks That's all part of the makeup. And it was a whirlwind. It was amazing. The community around "The Pitch" show is, like, incredible. The other founders that I keep in contact with now on a near daily basis, and-

Josh: Get out.

Cam: Genuinely.

Lisa: Aw.

Cam: Yeah.

Josh: Who is your pitch bestie?

Cam: The ChurchAI boys.

Josh: oh yeah

Lisa: yes

Cam: they're just incredible guys and they're, uh, on an absolute tear as well. And sometimes actually getting out of the local context and getting into some, around some big-thinking Americans can have really positive outcomes, and I definitely experienced that. Even around the event, I was able to close a couple deals and, and we've had a number of investors jump in. And so it's, it's just been an absolute whirlwind, but it was, it was one of those things where things just started, like, falling into place.

Josh: How was your experience pitching on the show? Like, the actual Pitch Room itself, which I, as I understand, was the first leg of your American tour.

Cam: Yeah.

Josh: And we'll get into that in a little bit. But how was your experience in The Pitch Room?

Cam: Look, I mean, whirlwind is the correct word. I mean, I was jet lagged. I had a period of the night before where I was just awake from 12:30 to 4:30 AM.

Josh: Mm-hmm.

Lisa: Ugh

Cam: And despite that, you know, I really felt I had got the pitch off exactly as I wanted. And ultimately, we all know the outcome here. You know, it was a pass from the people that were in the room. It took a little while, I'll admit, for the reality of it to sink in. You know, it, as founders, we're quite used to, like, the highs and the lows and the incredible adrenaline of being there, and then all of a sudden you're like, "Oh, wow," I just… That didn't quite go as I was hoping for. And it took-

Josh: Mm-hmm

Cam: I think it took maybe six hours before it sank in. And so I just went, and I was at Chick-fil-A sitting by myself, and that's when I had the real low. I was like, "Oh, no." Like, I'm on the other side of the world, away from my family and everything, and I failed at the objective. And, uh, there's all these people who are cheering me on from the other side of the world who are like, "Oh, no, you didn't, you didn't make it." And, ... and I was like, "Oh, man." Just real, as low as I get.

Josh: Yeah

Cam: And then out of the blue, I just get this call from a global ticketing platform CEO. And he called and said Cam, we wanna make a deal. Like, let's sort this out. And, um, it was the most intense whiplash I think I've ever felt. Doesn't that just typify the startup life?

Lisa: Yeah.

Josh: Oh my gosh, yeah.

Cam: Yeah.

Josh: I mean, the highest highs and the lowest lows.

Lisa: The lowest lows, yeah.

Josh: Sometimes within the same 12-hour period.

Cam: That's right.

Josh: So you got a call from, like, a Ticketmaster?

Cam: I'll say it's the... It's fourth in line. Yeah.

Josh: So not Ticketmaster.

Cam: Not Ticketmaster.

Josh: Couple notches down.

Cam: Yeah, yeah, yeah.

Josh: But still, that is exciting, man.

Cam: Yeah

Josh: So then what happened after you talked to this ticketing platform, where do you go from there?

Cam: We went on to Dallas. Was at a, a conference over there called Lions Den.

Josh: So this is like Dragon's Den, but with lions.

Cam: Oh, yeah.

Lisa: Josh

Josh: Like, Biblical lions?

Cam: Yeah. Yeah, yeah, yeah. And, I, I think that is kind of what it's supposed to be as a play on it, because it, it's a kind of an epicenter of, like, Christian, like, investors and-

Lisa: Oh!

Cam: Entrepreneurs and things. So we made some incredible connections there. Uh, and since both of that and the, the Florida thing, we've had six commits to the round.

Josh: That's awesome.

Lisa: How-

Josh: Six commits.

Cam: Yeah.

Lisa: How, how much have y- you raised?

Cam: Still a fair bit shy of the target, but we had a really interesting conversation with our... Well, I, I'll start by actually answering point blank your question here, Lisa.

Lisa: Kay great

Cam: Classic founder's like, "Oh, well, go over here." Uh- We're at... So we've, we've added an additional 200K since then.

Lisa: Okay.

Josh: That's great, Cam.

Lisa: Yeah.

Josh: That's a-

Cam: It is ...

Josh: relatively short period of time. Yeah.

Cam: It is. We've raised 500 in total now. And, I knew it was significant because our CFO changed his, his tune. It's quite unusual for CFOs to saying, "Cam, we could make it based on what we've currently got here indefinitely with these new contracts that were coming in."

Josh: Dude.

Lisa: That's pretty good.

Josh: Well done.

Cam: Hey. Again, like the different American mentality and the amazing connections, and the like present in person is just so different.

Lisa: Yeah. Agreed. That is what we have made all of our bets on.

Josh: Yeah, gotta press the flesh, as they say.

Lisa: Um.

Josh: I knew you wouldn't like that.

Cam: I have never heard that one. That's great.

Lisa: I was going a different direction, and then my brain was like, "Wait, what?"

Josh: It's a saying Lisa.

Lisa: Um, okay. So my question is, are you going to keep fundraising or you're just gonna work with what you got now?

Cam: We're gonna keep fundraising. There's an amazing US go-to-market opportunity that's still developing in pro sports. And that naturally requires some extra capital.

Lisa: Okay. So you mentioned the American mentality a few times. I'm just curious to like learn more from you, like culturally, what do you feel is different?

Cam: Sure. I, I feel like I have a unique perspective to be able to speak into this because my mother's an American. I was actually born in North Carolina. And I've lived between the two countries a little bit, mostly in New Zealand. But in New Zealand we have this prevalent culture called tall poppy, where if you kind of raise your head above the general thing, then you get cut down pretty quick because people feel a little threatened by that, or they don't want people being too prideful.

Lisa: Mm

Cam: You can imagine for launching a, a business and, and things, it can be a little detrimental. Uh- whereas in the US, I mean, people just gas you up like crazy. I mean, uh, they're- Like, like- Like they're so outrageously encouraging, and hon- I m- you know, maybe sometimes it's a little over the top, like we, we'll be real about that. But- ... uh, it definitely, you know, fills you with a bit of confidence and, and i- in many cases they're like, "Yeah, let's go early. Let's get behind you. You're a, a delusional young founder with a dream. Let's pour money on that and just see what happens." Like-

Josh: Let's feed that delusion.

Cam: Genuinely.

Josh: 'Merica

Cam: that's what I've seen. And that's, uh, what you get to experience firsthand.

Lisa: That's very cool.

Josh: So when are you moving back to the US?

Cam: I tell ya. This US go-to-market's not gonna do itself, right? Like it may have to happen.

Josh: So, I wanna go back to The Pitch Room and get your thoughts on the investors' feedback Mike Ma, he calls himself a grizzled fintech guy, and he told us after your pitch that he got hung up right away when you said that the take was 4%. Mike was like, "If you're gonna sell a business payments solution, you use bps. You're not in percents."

Cam: Yeah.

Josh: So like he took issue with the term you used, and it caused him to question your credibility as a fintech founder. Not to put you on the spot, but like how do you respond to that?

Cam: Look, if it all takes is the terminology, you could definitely argue that there's not a broader connection to the core problem that we're trying to solve. And one of the funny things about PaySquad is that we are a fintech, but when we're at fintech conferences, we feel like the weird kid. I mean, we are the ones who are talking about social cohesion, about helping groups like choose what kind of gifts they're gonna get, take tickets together. Like it is so different than like getting like bogged down in interchange rates and FX and basis points and the like. but-

Josh: Yeah

Cam: I can see like he's using his pattern recognition to go, "Is this a legitimate fintech founder that knows payments inside and out?" And I think that's fair. And I was so used to saying percent because that's what our, our customers understand a little bit more as well.

Josh: Yeah. An e-commerce company, even enterprise, they're not talking in bps when they talk about-

Cam: Yeah. Yeah ...

Josh: checkout buttons.

Cam: To be fair, like-

Lisa: Interesting

Cam: the head of payments would be, right? Like if you're talking to the, the head of payments in a huge retailer, of course, they're thinking in, in bps. Our ICP- we actually start with the head of marketing normally because we're such an acquis- a customer acquisition tool at checkout.

Josh: Mm-hmm.

Lisa; Oh.

Cam: Not trying to cope here, but that's part of the reasoning why I did it that way.

Lisa: Yeah.

Josh: Gosh. Yeah. I feel like the VC’s really pattern matched hardcore for a fintech company here.

Lisa: That's interesting.

Josh: And this is- it's not that it doesn't apply, but-

Lisa: Yeah, it's different...

Josh: it doesn't seem like the right rubric for this business.

Lisa: Is this your first time raising VC money?

Cam: It is, yes.

Lisa: So did you take anything away from "The Pitch Room" and, like, change how you're pitching your business because of it?

Cam: Probably the, actually the big one was, as founders, to be fully transparent, when you're presented with two numbers that you could share, you're like, "Let's go for that bigger one," 'cause that would be way cooler to share about-

Lisa: Mm.

Josh: The 4%?

Cam: Yeah. Not even, no.

Lisa: No.

Cam: An even bigger number than that. But I, I mentioned the, the GMV that we'd signed up.

Lisa: The GMV.

Josh: Yes

Cam: And GMV is a notoriously… What's the word? Like, elus- not elusive. That's the wrong word. But like, it can be-

Josh: Misinterpreted, vague. It's--

Cam: Yeah. It can use-

Lisa: Mm-hmm

Cam: it can mean so many things. What I was trying to communicate was like, "Hey, despite being virtually bootstrapped, we've been able to bring on some huge merchants." That's what I was trying to say. What I, I could've said instead was like, "Hey, we're gonna do 20,000 in revenue in this coming month."

And-

Josh: Right ...

Cam: one of those is like, wow, that's a really big number. One of the other ones I was like, is this even gonna be move the dial for anybody? And then I came to find afterwards that it probably would've. So-

Lisa: Yeah.

Josh: Yeah. Fun- so much of fundraising VC is just learning where the landmines are.

Lisa: Mm.

Josh: So you don't step on them.

Lisa: Yeah. We've seen the GMV thing before in, like, an investor update, and somebody was like, "Look." And then we're like, "Wait, no, that's GMV. That's, like, not what you think it is." It feels like you're being misled a little bit.

Josh: Yeah. Or like when people use contracted revenue for ARR, and you're like, "Wait, your actual ARR is a lot less."

Cam: You guys didn't give me the heads up beforehand. What are we-- No, just kidding.

Lisa: I know. Sorry.

Cam: Well, that's the beauty of the, The Pitch Show, right? Is that you have five opportunities in one intense session just to be like, "Right, let's start running across the landmine territory and just see what limbs are left afterwards, and see what we can learn."

Josh: Someone needs to make a graphic of what it's like to be on The Pitch Show. It's just-

Lisa: Dodging-

Cam: Just, just kind of like slow motion running.

Lisa: Yes.

Josh: It's just like Rambo.

Lisa: Dodging landmines. Oh.

Cam: Big old basis points landmine just [exploding noises]

Lisa: Oh my gosh.

Josh: Oh, yeah.

Josh: So of the, like, contracts you've got signed, what kind of revenue are we talking about?

Cam: Projected revenue?

Josh: Sure. Go with projected, just on the deals you think you'll have signed.

Cam: Between 15 to 20 million over the next three years.

Josh: Okay. You're either delusional, as you said, or you are on an absolute tear.

Lisa: Oh my gosh.

Cam: There's only one way to find out, right? Josh: Well, Cam, it's been an absolute pleasure. Thanks so much for-

Lisa: Yeah

Josh: traveling those 8,000 miles to come hang out with us.

Cam: It was a beautiful experience. I have no regrets

Lisa: Cam is such a lovely person.

Josh: So lovely.

Lisa: I feel like this pitch, though, was like New Zealand meets New York.

Josh: On one end of the spectrum, you've got grizzled Mike Ma, and then you got Cam, who's just like, "I want more people to get three-wheeled drift carts for their boys."

Lisa: Which might be a good business, the question is, is it venture backable, like does it reach venture scale,

Lisa: Not the $10 million a year that Elizabeth thinks this can be.

Josh: Only in venture is a $10 million a year business a bad business.

Lisa: Unfortunately. Either way, I hope that Cam does not become that grizzled fintech founder, and he can retain his natural sparkle and joy.

No offer to invest in Paysquad is being made to the listening audience on today’s show. But you can invest in The Pitch Fund, where we invest alongside the VCs on the show. We’re currently deploying Fund II, and we’re open to new investors through the end of the year! To learn more, go to thepitch.fund

Next week on The Pitch…

Iryll: We are raising a $600,000 pre-seed round to become the OS for global churches.

Mike: If you can be the CFO of, like, one of the most important social fabrics that binds community together, and by the way, holds a crap ton of assets, real estate shoot, I'm in.

That’s next week! Subscribe to The Pitch on your favorite podcast player so you don’t miss future episodes. You can watch full length versions of every pitch over on our Patreon at The Pitch Uncut.

And if you’re a founder raising a pre-seed or seed round, apply to pitch at our next event! It only takes a couple minutes to apply, just go to pitch.show/apply

We’ll see you next week, in the PITCH ROOM.

–

This episode was made by me, Josh Muccio, Lisa Muccio, Anna Ladd, and Enoch Kim. With deal sourcing by Peter Liu, John Alvarez, and Phoebe Sun.

Music in this episode is by The Muse Maker, Breakmaster Cylinder, The Firmware Rebels, Marlon Gibbons, Joey Kantor, Dreaming of Stars, and Peter Jean & The Runaway Queen.

The Pitch is made in partnership with the Vox Media Podcast Network.