The Barbershop Visit That Sparked a $750M Idea: The Squire Origin Story

To really test our product, we decided to buy a barbershop with what was left in the bank. It felt like a make‑or‑break moment, so we pushed ahead even though we had around sixty thousand dollars left.

Welcome to Before It Clicked, where we unpack the path from idea to product‑market fit. Today I’m joined by Dave Salvant of Squire, the non‑technical founders who built a software company last valued around seven hundred fifty million dollars; Dave, set the scene—where is Squire now?

We serve over five thousand barbershops and thirty‑three thousand barbers across the United States, Canada, and the United Kingdom. We’re growing more than thirty percent year over year.

You and Songe didn’t come from software, so why start a tech company, and why barbershops?

We were young professionals in New York, whiteboarding at Columbia on weekends, and kept hitting the same personal headache: haircuts took hours and felt stuck in time while everything else was going digital. We wanted to modernize that experience.

How did you go from that spark to a concrete plan?

A looming haircut reminded us of the pain, so we started interviewing barbers. Without engineers, we focused on discovery—would they use it, would they pay, and could we build real trust early?

Did you do top‑down market sizing, and was the pain universal beyond your own community?

We did minimal sizing at first and sanity‑checked with friends from different backgrounds. Everyone hated the back‑and‑forth, the waiting room slog, and having to pay in cash.

What specific problems did you choose to tackle first?

Scheduling chaos, long waits, and making the payment easy and digital.

People called it Uber for barbers early on—was that accurate?

Not really. We staged cuts at WeWork to test booking and payouts and to seed early demand, but it wasn’t a true on‑demand network.

Walk us through the early timeline and the first big lesson.

We went full time in January twenty fifteen, raised angels in June, and shipped an MVP by late summer. By October, double bookings made it clear we had to run the shop’s operations end to end.

Why insist on software with no technical background, and how did you pivot to full stack control?

Software was the only path to outsized impact and fit the problem best. There weren’t many tools then, so we committed to owning the whole workflow.

Tell the Chelsea shop story and what it did to your runway.

A beta shop sold a week before launch, so we bought it with roughly a third of our remaining cash. We ran it ourselves as a test kitchen, comped mistakes, covered barbers when glitches hit, and learned the business from the front desk up.

Were other shops live during this, and how were you making money?

We kept a few on the legacy flow while building our new commander system in our shop. We didn’t charge SaaS; we earned modest booking fees, maybe around two thousand dollars a month.

When did momentum build, and how did fundraising go?

YC Fellowship gave us twenty thousand dollars, then YC Summer twenty sixteen helped us deploy the full OS to several shops. We pieced together under a million in small checks; Series A was tough, later rounds were smoother.

How did the vision evolve, and when did product‑market fit show up?

We leaned into an all‑in‑one: booking, marketing, payments, payroll—with payments as the core. YC forced us to focus on active shops and transactions, and once the full suite was live, the curve bent up and stayed there.

After that, was it mostly distribution, and what scrappy growth played a role?

Yes—SMB sales cycles are quick, so demos turned into closes fast. Chalk QR codes around the city looked cool but didn’t convert; partnering with WeWork added credibility, and when a bug knocked us offline pre‑demo day, we flew to Sacramento and handed barbers cash to keep them with us while we fixed it.

Would you have found fit without buying the shop, and what would you tell your twenty fifteen self?

We probably would have struggled much more. Get the product into customers’ hands sooner and iterate; living the pain as both consumer and operator was our roadmap.

Any moments you thought about quitting, and how do you close this out?

Quitting wasn’t an option; we kept our heads down through the swings and focused on the impact for small businesses and their communities. We’re still building, improving, and aiming to be the default way you get your haircut.

Dave, thanks for coming on—this was great.

Appreciate it—thanks for having me.