Kristin Myers: Now, in 1900, a haircut only cost $0.25, and today the national average is $43. Now, what hasn’t changed much is how most barbershops are run: phone calls, walk-ins, a paper book behind the counter. My guest was a corporate lawyer who thought he could fix that. Before he built the software, he and his co-founder did something pretty unusual. They actually bought a barbershop and then ran it themselves. But first, let’s take a look at the company. The road from an idea to the opening bell starts right now.
The barbershop may be one of the oldest businesses in America, but for decades, a lot of them were still running the old-fashioned way: phone calls, walk-ins, cash, paper schedules. That’s the opportunity Songe LaRon and his co-founder Dave Salvant saw back in 2015. But there was one problem: they didn’t actually know how to run a barbershop. LaRon was a corporate lawyer. So before trying to disrupt the industry, they bought a barbershop and ran one themselves.
The lesson: barbers didn’t just need an app to book haircuts. They needed technology to run the entire business. So Squire built it: booking, payments, payroll, marketing, and customer management, all in one platform designed specifically for barbershops. And investors have put more than $140 million behind the idea as Squire has expanded its reach across the barbering industry.
Now the next bet is AI. Squire is building AI into the back office, helping shops answer calls, rebook customers, market their business, and make sense of their data. The idea is simple: let the barber focus on the chair while AI helps run the business behind it. And Squire has the data to see how that business is changing. Its 2026 State of Barbershops report analyzed millions of appointments, from what customers pay, to when they book, to what keeps them coming back. And now Squire is pushing even further into financial services, including a partnership with Klarna designed to bring more payment options into the barbershop.
But here’s the challenge: can Squire go from software that helps barbers book a haircut to the technology and financial platform that powers the entire barbershop economy? And can a company that once bought a single barbershop just to understand the business build the operating system for an entire industry? From Startup to Stock Exchange, Squire co-founder and CEO Songe LaRon is next.
Joining us now here at the desk is Songe LaRon, CEO and co-founder of Squire. Songe, always great chatting with you. So I want to go a little bit into your background. You know, I had mentioned before that you were actually a corporate attorney, so this is a bit of a pivot, just to put it mildly. So I’m curious to know, why barbershops? Because neither you nor Dave were in this world before, Dave Salvant of course being your co-founder.
Songe LaRon: Yeah. When we started Squire, Dave and I were friends. We both lived in New York, and we both had corporate careers. I was a corporate lawyer, as we said. He was in finance. And we found ourselves kind of unfulfilled with the trajectory we were on, and wanted to build something more meaningful, where we could create a legacy. And we would brainstorm ideas on the weekends, and we came across the idea of the barbershop experience.
You know, I started going to the barber as a kid with my dad, maybe when I was like six. And here it was, you know, over two decades later, and there was no real innovation in the space. Still a very antiquated cash business. Hard to make an appointment. Long wait times. And we thought that this seemed like a pretty big industry. Like, so many people go to barbershops, and Silicon Valley and technology, writ large, were just ignoring the space. So we decided, hey, let’s give it a shot. So we quit our jobs and jumped into it, and we’ve been working on Squire ever since.
Kristin Myers: Okay. But here’s the thing, though. You didn’t just quit your jobs and jump into it. You guys actually bought a barbershop and then ran that barbershop, which is a pretty unusual decision to make. Why did you decide to do that, and what did running that barbershop even entail? Were you giving haircuts? I’m assuming you weren’t giving the haircuts.
Songe LaRon: Well, I always say we were doing everything but giving haircuts, because I wouldn’t trust myself with the clippers. So what happened was, first we quit our jobs and jumped in. We started trying to build a product, and eventually found a CTO co-founder to build the first MVP, the first version of the app. And then we started trying to get customers on, get barbers on, and we were not getting a lot of traction with that app. And what we learned was that what they wanted was a central system for the entire shop, not just a single app for an individual barber.
So we went back and built that, and got our first customer on. We were so excited. And then that customer, within a few weeks, told us he was going to close down the barbershop and just give up on it. So we were kind of desperate. We had one customer, and that customer was churning. So we said, hey, this could be an opportunity to kind of step in, assume the lease, become the owners of the shop ourselves, and run the shop while we were actually building the software.
And it was an incredible experience, because we were able to learn so much, putting ourselves in the shoes of our customer. We found out how hard it was to manage barbers. The head barber quit on us, and there was a whole lot of tension. But over time, we worked it out. And as we were building the software, we started building the solutions that we needed as owners. And we ran that for about a year, and then eventually another shop came in and took it over. Running a barbershop is super hard. That’s one thing that we learned.
Kristin Myers: I was going to say, say a little bit more about what you learned. Are there things that you learned that were really integral to Squire and to the software that you built, that perhaps you might not have been able to learn had you not made that decision to buy and run a barbershop?
Songe LaRon: Yeah, definitely. There are a few things that stood out that we learned, that now seem totally obvious, but at the time, no one else was really doing. For one, we learned how important it was to have a point-of-sale system that’s integrated with the appointment system. That seems like, yeah, duh. But at the time, no one was actually doing that. So that was one of the first innovations we brought to market.
Another pain point that we experienced was paying the barbers. So every week, barbers that are on commission expect to get paid by the owner. And it gets very, very complicated, because they’re getting tips, which they want to keep 100% of, and they’re getting commissions, which are a percentage of each service. And then the owner is left to figure out who owes what, doing manual math. And inevitably, people say, what? You didn’t pay me enough. I’m owed more. So we were like, how can we solve this with software? And that was one of the features that we built, to make that entire process seamless.
Kristin Myers: Now, you mentioned briefly that you had built your first sort of iteration of Squire, and you were struggling to get clients on board, and you realized that there were things about it at first that didn’t necessarily work so well. Talk to us a little bit about some of the, I don’t want to call them failures, but some of those things that you didn’t get quite right the first time around.
Songe LaRon: Yeah. So we started out with a mobile app first. And the idea was we could solve all the problems that I experienced as the person getting a haircut. Make it super easy to find a barber, book, pay seamlessly, kind of have that Uber-like experience where you don’t need to dig in your pocket for cash. We were like, this is awesome. Everyone’s going to love this. We’ll give it to all the barbers, and they’ll love it.
What we found was that the individual barbers would say, okay, cool, I’ll use it. Send me new customers. I’ll use your little app. But for all their current customers, their existing business, they were not using us. So as a result, we were doing a few appointments per barber per week, but it wasn’t enough to actually build a meaningful business. And we thought early on, maybe we could build a marketplace and do things to get consumers on and send them to barbers. But at that stage, building enough consumer demand to have liquidity, supply and demand, on the app was nearly impossible. There was just no way we were going to be able to build enough demand to drive it to the clients.
So we learned the hard way. We learned quickly. That’s the beauty of being a startup: you make mistakes, you fail fast, and then you iterate. So within, I would say, six months of launching that product, it was very, very obvious that we didn’t have product-market fit. So we went back to the drawing board.
Kristin Myers: So, speaking about clients, I want to talk about client retention, because this number really surprised me. 48% of clients, and this is a number from your own report, are one-and-done customers. They come once, and they never come back. Which shocked me, because men are so loyal to their barbers. They go to their barber repeatedly. Even if their barber is on vacation, they just don’t get a haircut. Or at least the friends that I know are very, very loyal to their barbers. So what is happening here, that almost half go once and then don’t go back?
Songe LaRon: Yeah. So men are extremely loyal to their barbers, once they find their barber. That’s why that first appointment and that first experience is so critical, that the barber gets it right. And then when they retain a customer, it’s a very long lifetime value. But often what happens is clients will be experimenting, maybe traveling, or maybe they get a haircut from one guy the first time when they’re on the market for a new barber, and they don’t necessarily stay, right?
That’s why, when we talk to shops and barbers and try to, you know, tell them how to be successful as business owners, retention is so, so important, right? And we’ve built tools using AI, which I’m sure we’re going to get into, to really help increase retention for them. New clients are what everybody likes. You feel great when you get a new client in the door, and that’s great. We do help with that as well. But retaining those clients is even more important.
Kristin Myers: Well, talk to me a little bit about how much of that is a barber problem, because there are two things that are happening here at once, right? There is the customer experience, which might include the ease with which you can book an appointment, pay, tip, etc. And then there’s just the pure skill level, right? Do you actually like your haircut? And I mean, as a woman, we will put up with a lot if we feel like the way our hair looks at the end of the appointment is still good. We’ll put up with a lot of those other experience problems on the front end and the back end. So talk to me a little bit about how much of it is a barber issue and how much is a business issue, as far as you’re seeing it, with that client retention.
Songe LaRon: Yeah, I think there’s a bare minimum, where the cut has to be good enough. Like, you know, Squire is not going to save you from a bad cut.
Kristin Myers: You can’t save that.
Songe LaRon: Well, we help. We do have review systems. We have reviews embedded. We have images, and actually videos, that clients can see of the services before they book, of that specific barber, right? Which really, really helps with that. But I always say that most clients can’t tell the difference between a good haircut and an outstanding haircut. They want it to be good enough, right? And men tend to be a little bit simpler when it comes to that. But what they will remember is if the experience isn’t good. If they’re not greeted when they walk in the door, if they don’t feel welcomed, those things sometimes count just as much, if not more, than the actual haircut.
Kristin Myers: Would you say that those other touches actually make the difference, as far as you’re seeing it from some of the customers, between a good haircut and an outstanding haircut?
Songe LaRon: Absolutely. Particularly when we see that the price of a haircut has risen significantly, you know, to on average about $43. But in some markets, it’s well, well above that.
Kristin Myers: I was very surprised also. Maybe it’s because we’re here in New York, but all my friends are complaining that haircuts now are $60, $70. So $43 sounded pretty good today.
Songe LaRon: In cities like New York, it’s closer to $60. And then when you add tips on top of it, it can get... So when the price is going up, consumers expect the service to improve as well. You can’t charge, you know, $80 or $60 and then provide a $20 service.
Kristin Myers: So what actually makes a barbershop work? Well, Squire looked at nearly 14 million appointments over a year, and here is what they found. The average cut in America now costs $43, much higher, of course, as Songe was just saying, in cities like New York. But that ranges from $35 in the Midwest to $45 in the West. Now, the average barber takes 94 appointments a month, and a returning client comes back every 48 days. But about 44% of visits come from a returning client, which means that the majority don’t. And shops still running on pen and paper lose 5 to 10 hours a week just to administration, a full workday, with no-show rates as high as 20%. And all of that is the company’s own data.
We’re back now with Songe LaRon, CEO and co-founder of Squire. So, speaking about that 5:00 haircut, your report actually said that peak weekday bookings moved in time. It was previously at 5 p.m., and then it went to 4 p.m. Talk to us a little bit about that. Why?
Songe LaRon: Yeah, that’s an interesting data point, the hour shift. We don’t really know the reason. Sometimes you see trends in the data, and it’s interesting, but not quite clear. We do see that Friday is consistently the busiest day for barbers, pretty much consistently, right? Which makes sense, because people want to get their haircut for the weekend, right? So they get it on Friday. But why the shift to 4 p.m.? Not sure.
Kristin Myers: Well, I was surprised to see that weekday cuts actually happened between 8 and 5. So people are, I guess, leaving the office to go get a very quick cut. Okay. So what does that mean for a shop owner who’s trying to plan out their week?
Songe LaRon: Yeah. So what shop owners need to do to really have a successful business and maximize revenue is to think about increasing the utilization of their calendar. So they want as many of the open slots booked as possible, and as little downtime as possible, where the barbers are sitting there with nobody in the chair. So we’ve built tools that actually help them do that, using AI.
One of our features is called Engage. It essentially is a marketing tool that allows the shop and the barbers to send messages to their clients to get them to book more often. But now we’ve imbued it with a layer of intelligence, where it can learn the actual booking pattern of each individual client, and it knows when they need a haircut, perhaps even before they do. And it sends them the right message at the right time, based on the barber’s availability, to make sure that there are no open slots.
And we see that these AI-based campaigns are converting really high, on average about 20%. So if they send out a message that goes to 100 clients, they’re going to get 20 bookings on the same day. And it’s really almost like magic for our customers. They can just turn it on, and then the bookings start to flow in, right, to make sure that they don’t have gaps in their schedule.
Kristin Myers: What else is the AI doing in the shops, besides obviously sending out those booking requests? I know, for example, when you call restaurants now, AI is answering, sometimes before hours or out of hours. Is AI being utilized in that way inside the shops as well? How are you seeing most of the shops deciding to use artificial intelligence?
Songe LaRon: Yeah, good question. So we’re seeing really high adoption of the marketing tool that I mentioned. About 58% of our shops are already using the AI version of that, and it’s driving those bookings. We’ve also introduced a voice assistant, which we call Operator. And it does exactly what you said, where it can answer calls for them, because we know that barbershops get a lot of calls constantly. And the worst thing is when they’re on the phone, trying to talk and cut at the same time. It’s a poor experience for the client, and it’s not good for the barber as well.
So we give them the ability to have the AI answer and then actually place the booking for them. If someone calls to reschedule, it can do that. It can do pretty much what a front desk assistant would do, and we’ve given them that functionality. But now, actually, I think next week, so maybe this is news, we’re launching increased functionality that will cover SMS and chat as well. So now, when a client is texting the barber, which often happens, hey, I’m running late, hey, can I add my son, whatever, the AI can answer for the barber as well and make sure that those bookings take place.
Kristin Myers: So I know first. We love being first to know about new features.
Songe LaRon: Maybe I wasn’t supposed to say that.
Kristin Myers: No, no, no. We’re live now, so everyone knows. But I’m glad you mentioned that SMS feature, because I was going to say, again, this is just from my experience with my brother and my guy friends, I’m curious to know how this platform is working. Because it seems as if, with a lot of barbers, a lot of things are highly individualized, right? You have your one chair as a barber, and you have your loyal clients that will text you. How are you finding the uptick in adoption, moving from that mentality of, I’m an individual entrepreneur that just happens to have a seat inside of this larger ecosystem, to something that will integrate your appointments, your texts, all of those phone calls? Do you know what I mean? Because right now, some barbers are like, I don’t need them to send the emails on my behalf. I’ve got my own clients that text me and fill up my chair.
Songe LaRon: Yeah. So the evolution has been from pen and paper. That’s where a lot of them started, and some are still there, but not many these days, because it’s very inefficient for the barber, and it’s an extreme burden to constantly be having to reply to text messages for bookings. So they went from pen and paper to software, which is where we stepped in ten years ago, where we provided them with the ability to really have an operating system to better manage their business. The next evolution is AI and agentic workflows.
The way that I see it is that much of the operational work of running a barbershop, you know, answering the phone, booking appointments, handling payments, all that stuff, will be handled by agents. We’re already starting to do that with the voice agent I mentioned and the marketing agent. And that will free up the time of the barber to really just focus on the service, the human connection, the hospitality, the greeting, remembering all the details of their clients. So I see that’s where things are going, and that’s where Squire is delivering.
And to me, it’s a really exciting future, because we hear so much negativity around AI and job displacement, and a lot of that is true. For our customers, we see it more as an opportunity, because they’re not going to be replaced by robots. Nobody wants a robot cutting their hair. But it can empower them. It can really free them up, allow them to make more revenue, save time, and just really operate their businesses much more efficiently.
Kristin Myers: Now, you mentioned a little over half. I think you said 58% have already adopted the AI on the platform. What’s stopping, you know, the other 40%? What are you hearing from them?
Songe LaRon: Yeah. So with our customer base, they’re so busy, on their feet, working with their hands every day, that sometimes it’s hard to just get the message through. So often what happens is, when I go to events, or when I’m going to trade shows and talking to barbers, and I tell them all the stuff that we have, they’re like, what? I didn’t even know about that. Sign me up, right? So that’s something we’re working through: how to get the message of the improvements and functionality to as many of our customers as possible. And then some people are naturally resistant to change. It’s not going to be instant. There are folks who are very comfortable with what they’re using now, and something new is a little bit scary. And that’s okay. We work with them over time to get them to embrace the newest technology.
Kristin Myers: I want to dive a little bit into some of the numbers, the partnerships, the revenue. So you have a partnership with Klarna, which, you know, everyone knows, but if they don’t: buy now, pay later. Now, this is for $43 haircuts. Talk to us a little bit about why you felt that was a necessary and good next step for you guys to take, in partnerships.
Songe LaRon: No, it’s a great question. Our position on that is that we want to meet consumers where they are. We want to give them all the optionality possible in how to pay. And $43 is the average, but we do have services provided by some barbers on our platform that are well over $100. I don’t know if you’ve ever heard of micropigmentation.
Kristin Myers: Yes, I have.
Songe LaRon: So for folks at home, that means if you’re getting a little loose on top, if it’s getting a little light, if your hairline is getting pushed back a little bit, micropigmentation is for you. Yeah. And it’s almost like mini tattoos that the barbers perform. And this has become very popular, and this service costs upwards of $1,500.
Kristin Myers: Oh my God.
Songe LaRon: And then they have to come and get it maintained. So for things like that, we wanted to provide flexible payment options, and we think Klarna is a great partner for that.
Kristin Myers: I would just go bald. I would go cue ball.
Songe LaRon: No, I wouldn’t. I can’t give up hope. I can’t give up hope.
Kristin Myers: Okay. Let’s talk about your raise. You’ve raised more than $140 million. How do you think about your business? Are you thinking about it as a software business, or are you thinking about it as a financial services business, or something else altogether?
Songe LaRon: I’m thinking about Squire eventually being the agentic platform for these small business owners. I think that’s where things already kind of are, and they’re going to continue to move toward that. We’ve seen that on the consumer level. Obviously, there are all the consumer agents that are really growing in popularity. At the enterprise level, you know, we’re seeing that really become normal. But at the SMB layer, there’s kind of a gap currently. These business owners don’t have the IT resources, and they don’t have the time to vibe-code something themselves. They need something that just works and provides the outcomes that they need. And we think that Squire can really bring agentic systems to them in a way that really adds value to their lives. So that, to me, is a really exciting future that we’re working toward.
Kristin Myers: So it sounds like you’re really targeting moving beyond barbershops, and maybe into nail salons and women’s salons, because there are a lot of platforms that exist that do some of those things, at least that I’m familiar with, with the appointments that I’m booking.
Songe LaRon: Yeah. Our focus is still barbershops. We still have a lot of room to grow within barbershops. But you’re right. I mean, what we built for barbershops, this agentic system, I think will be very well received across other adjacent verticals. And there are others that are going after those spaces. But I would argue that no one has really done it from, like, a first approach yet, in a way that’s at scale. So we’re looking at that. But barbers are really our core, and we’re going to continue to invest there and to innovate for them as well.
Kristin Myers: Really quickly, about ten seconds. Since we’re on the floor of the stock exchange, do you ever think about going public? If so, when do you think that might be?
Songe LaRon: I think about a lot of things. I don’t think that’s something that’s imminent for us. I focus on, you know, the next 12 months, and we see a lot of opportunities staying private. But that being said, you know, maybe one day. Never say never.
Kristin Myers: Well, we’ll have to have you back as you guys expand. Thank you so much. Songe LaRon, co-founder and CEO of Squire. Thanks so much for joining us today.
Songe LaRon: Thanks.
