Squire founders

Squire founders turned a pop-up barbershop into a billion-dollar business and learn valuable startup lessons on innovation, growth.

Squire founders

Squire co-founders Songe LaRon and Dave Salvant built a pop-up barbershop inside a WeWork space to test their booking app firsthand. The experiment proved their platform solved real scheduling and payment problems for customers, but it also exposed a critical gap: the app wasn’t built to serve barbers. That pivot — from a customer-first product to a barber-first platform — became the foundation of Squire’s long-term growth and offers a reusable lesson for any founder building a two-sided marketplace.

Startup success stories rarely follow a straight line. Behind every polished pitch deck is a messier story of founders testing assumptions, watching them fail, and rebuilding with better information. Squire, the booking and point-of-sale platform built for barbershops, is one of the clearer examples of this pattern in action.

Before Squire became a trusted name among barbershop owners, it was an idea tested in the most unglamorous way possible: a temporary barbershop set up inside a WeWork office. Co-founders Songe LaRon and Dave Salvant weren’t trying to build a trendy pop-up experience for its own sake. They needed real feedback, fast, and they needed it from actual customers interacting with their product in a real setting.

This post breaks down what happened during that early experiment, why it mattered, and what founders building their own products — especially marketplace or platform businesses — can take from it.

Why did LaRon and Salvant set up a pop-up barbershop in a WeWork space?

Early-stage founders face a persistent problem: they can build what they think the market needs, but they can’t know for certain until real users interact with it. LaRon and Salvant faced this exact challenge. They had an idea for an app that would fix the frustrations they’d personally experienced as barbershop customers, but an idea isn’t the same as validated demand.

Rather than rely on surveys or hypothetical conversations, they created a live environment. Setting up a pop-up barbershop inside their WeWork space let them observe real behavior: how people booked appointments, how they paid, and where friction showed up in the process. This is a classic lean-startup move — get a minimum viable version of your idea in front of real users as quickly as possible, in as close to a real-world setting as you can manage, and let their behavior (not their opinions) tell you what’s working.

The choice of a WeWork space also mattered strategically. It gave them access to a built-in audience of working professionals who needed haircuts but didn’t necessarily have time to deal with the scheduling headaches common in the barbershop industry. That made it an efficient testing ground rather than a random stunt.

What problems did the pop-up experiment reveal for customers?

The pop-up confirmed what LaRon and Salvant had suspected from their own experience as customers: scheduling and payment were genuinely broken in the traditional barbershop model. Walk-ins meant unpredictable wait times. Phone-based booking was inconsistent. Payment was often cash-only or required awkward card readers that slowed down the checkout process.

By building a booking and payment flow into their app and testing it with real customers at the pop-up, they validated that solving these two frictions — scheduling and payment — had real value. Customers wanted the convenience of knowing exactly when their appointment would happen and the ability to pay without fumbling for cash or waiting on a card machine.

This is the part of the story that looks like a clean success: identify a pain point, build a solution, test it, confirm it works. Many startup narratives stop here. Squire’s didn’t, because confirming the problem was only half the equation.

What critical gap did the app’s early version miss?

Here’s where the lesson gets more interesting. While the app solved real pain points for customers, it hadn’t been designed with barbers’ needs in mind. A platform built for a two-sided market — in this case, customers who want haircuts and barbers who need a sustainable, efficient way to run their business — can’t succeed by only optimizing for one side.

This is a mistake that’s easy to make and hard to spot early. Founders instinctively build from their own vantage point. LaRon and Salvant experienced the barbershop industry as customers first, so naturally, their initial product reflected a customer’s priorities: convenience, speed, predictability. Barbers, meanwhile, have an entirely different set of concerns — managing their schedules efficiently, handling walk-ins alongside bookings, tracking payments and tips, and running what is, for many of them, an independent small business.

An app that makes booking easier for customers but adds complexity or friction for barbers isn’t a complete solution. It’s a half-built bridge. If barbers don’t want to use the platform — because it doesn’t fit how they actually work day to day — the customer-facing improvements become irrelevant. No barbers on the platform means no bookings to make, regardless of how smooth the customer experience is.

Why does this matter for any two-sided marketplace startup?

Squire’s early pivot illustrates a principle that applies far beyond barbershops: in any marketplace business, both sides of the transaction need to feel the product was built for them specifically, not just tolerated as a necessary participant.

Consider the parallel structure found in other well-known two-sided platforms. A rideshare app has to serve drivers and riders. A freelance marketplace has to serve freelancers and clients. A food delivery platform has to serve restaurants, delivery drivers, and diners. In each case, founders who over-index on one side’s experience while neglecting the other’s operational reality tend to struggle with retention, even if their initial user acquisition numbers look promising.

Choose to build for supply-side users first if your market has more friction convincing suppliers to join than convincing demand-side users. In Squire’s case, convincing individual customers to try a more convenient booking app was the easier sell. Convincing barbers — who often had established routines, existing client relationships, and limited time to learn new software — to adopt a new system required a platform explicitly designed around their workflow, not just a polished add-on to a customer app.

How did Squire adjust its product after the pop-up experiment?

The direct outcome of this discovery was a shift in product philosophy: Squire needed to be rebuilt as a platform barbers would actively want to use, not just a booking widget layered on top of their existing operations. This meant rethinking the product to address real barber pain points — things like managing their own schedules, processing payments without added hassle, and running their business more efficiently day to day.

This shift reflects a broader lesson in product development: validating a customer problem is necessary, but it’s not sufficient when your business model depends on adoption from multiple stakeholders. Founders need to test their assumptions with every group whose buy-in is required for the business to function, not just the group that’s easiest to reach or most sympathetic to the founders’ personal experience.

It’s also a useful reminder that product-market fit isn’t a single checkpoint you pass and move on from. It’s layered. You might find fit with one audience segment while still missing it with another, equally essential, segment. The pop-up barbershop experiment didn’t fail — it succeeded at revealing exactly where the gap was, which is arguably more valuable than a test that confirms what you already believed.

What can founders learn from Squire’s early pivot?

A few practical takeaways emerge from this story for founders building their own startups:

Test in the real world, not just in theory. LaRon and Salvant didn’t rely on assumptions or market research reports. They created a live environment where real customers interacted with their actual product. If your startup involves a physical service or in-person experience, consider whether a small-scale, real-world test could surface insights faster than additional planning.

Map every stakeholder in your business model, not just your most visible user. If your startup connects two or more groups — buyers and sellers, service providers and clients, creators and audiences — map out the needs of each group separately. Don’t assume that solving one side’s problem automatically benefits the other.

Treat early gaps as information, not failure. Discovering that the app didn’t serve barbers wasn’t a dead end for Squire. It was the specific, actionable feedback needed to build a better version of the product. Founders who treat these moments as data points, rather than setbacks, tend to iterate faster.

Prioritize the harder adoption problem. When one side of your marketplace is naturally easier to attract than the other, put extra resources into solving the harder side’s needs first. For Squire, that meant designing specifically for barbers once it became clear their adoption was the bigger hurdle to sustainable growth.

Keep learning from real startup journeys.

Squire’s pop-up barbershop experiment is a small but telling example of how startup success often comes from being willing to test assumptions in public, absorb uncomfortable feedback, and rebuild based on what’s actually true rather than what founders hoped would be true. The company’s willingness to identify and address the barber-side gap — rather than declaring an early win based on customer enthusiasm alone — set the stage for a more durable business.

If you’re building a startup of your own, particularly one with multiple user groups who need to be convinced to participate, take a page from LaRon and Salvant’s approach. Find a low-cost, real-world way to test your core assumptions before scaling. And when you find a gap, treat it as the most valuable feedback you’ll get.

Frequently asked questions

What problem was Squire originally trying to solve?

Squire’s founders, Songe LaRon and Dave Salvant, set out to fix the scheduling and payment friction they personally experienced as barbershop customers, including unpredictable wait times and inconvenient payment methods.

Why did Squire’s founders set up a pop-up barbershop instead of just launching the app?

A pop-up barbershop inside their WeWork space let LaRon and Salvant test their booking app with real customers in a live setting, generating authentic feedback faster than surveys or theoretical planning could provide.

What was the main flaw in Squire’s early app?

The early version of the app addressed customer needs around booking and payment but wasn’t designed around barbers’ workflows, making it harder to secure the barber adoption the platform needed to function.

What lesson does Squire’s story offer founders of two-sided marketplaces?

Founders should validate and design for every stakeholder group in their business model, not just the easiest or most visible user, since insufficient adoption on either side can stall the entire platform.

Is the pop-up barbershop approach useful for other types of startups?

Yes, particularly for startups offering in-person services or physical products. Creating a small-scale, real-world test lets founders observe genuine user behavior rather than relying on assumptions or secondhand feedback.

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