Welcome back to Founder Frames.
Decoding the playbooks of entrepreneurs building category-defining companies.
Most founders would never put barbershops in a venture-scale SaaS deck.
Too local.
Too offline.
Too fragmented.
Too much cash.
Too much culture.
Songe LaRon and Dave Salvant saw something different.
They saw an industry with repeat customers, recurring revenue, complex scheduling, payments, loyalty, walk-ins, no-shows, inventory, staff management, and customer relationships.
In other words:
A business operating system.
It just did not look like one yet.
That insight became SQUIRE, the barbershop management platform that grew into one of the most important vertical SaaS companies in a market most people ignored.
The lesson is not “build for barbershops.”
The lesson is sharper than that.
The next great SaaS market may already exist.
It just might not look like software.
The Market Everyone Walked Past
Songe LaRon did not enter the barbershop world as an industry insider.
He entered it the way many people do: as a customer.
He had been going to barbershops since childhood. Years later, he noticed something strange. Almost every part of modern life had been touched by software, but the barbershop experience still felt stuck: long waits, cash-heavy payments, manual processes, and inconsistent scheduling. YC described SQUIRE as business management and point-of-sale software for barbershop owners, born from LaRon’s realization that the haircut experience remained largely unaddressed by modern software.
That is where overlooked markets usually begin.
Not with a perfect TAM slide.
With a sentence people repeat without questioning:
“That’s just how this industry works.”
Long wait times?
That’s just how barbershops work.
Cash payments?
That’s just how barbershops work.
Unpredictable schedules?
That’s just how barbershops work.
But “that’s just how it works” is often another way of saying:
No one has cared enough to rebuild the system.
The First Idea Was Wrong
Their first version was not the SQUIRE we know today.
It was closer to an “Uber for barbers.”
A consumer app.
Book a barber.
Get a cut.
Make the experience smoother.
It made sense from the outside.
But the market pushed back.
They could not get enough shops on board. They even carried a heavy barber chair into coworking spaces and brought the barber to the customer because shops were not adopting the original model.
That detail matters.
Because a weaker founder would have called that failure.
A better founder calls it evidence.
The first product was wrong, but the problem was real.
Customers wanted convenience.
Barbers wanted income.
Shop owners wanted control.
The mistake was assuming the main opportunity was the booking layer.
It was not.
The real opportunity was the operating layer underneath.
Then They Did the Thing Most Founders Avoid
They bought a barbershop.
That sounds extreme.
But it might be the reason SQUIRE worked.
Most founders do customer discovery from the outside.
They schedule calls.
They run surveys.
They write notes.
They extract insights.
LaRon and Salvant went deeper.
They became operators.
YC reported that while pivoting from the mobile app into a SaaS product for the full barbershop, the founders purchased and began operating their own Manhattan shop.
That move changed the quality of the information they could access.
Because when you operate the business, you do not just hear about the pain.
You inherit it.
You feel the tension between walk-ins and appointments.
You see how much revenue disappears from no-shows.
You understand why shop owners care about brand, not just booking.
You learn that payments are not just transactions. They are cash flow.
You see that loyalty is not a marketing feature. It is survival.
This is the difference between researching a market and being trapped inside its workflow.
Research gives you opinions.
Operations give you edge.
What SQUIRE Actually Became
SQUIRE became more than a booking app.
That is the key.
The company built an all-in-one barbershop business management system: scheduling, client management, branded booking, loyalty, payments, same-day deposits, business insights, and tools for shop owners to manage their money, teams, customers, and brand. SQUIRE’s own product positioning emphasizes control over schedule, clients, money, and brand, plus online and in-person payments and branded booking experiences.
That is what vertical SaaS does when it works.
It starts with one painful workflow.
Then it expands into the system of record.
Booking becomes payments.
Payments become customer data.
Customer data becomes retention.
Retention becomes business intelligence.
Business intelligence becomes control.
By 2021, SQUIRE had processed over $100 million in payments and was used by more than 1,000 shops across the U.S., Canada, and the U.K.
Endeavor later noted that SQUIRE reached almost 3,000 establishments across the U.S., Canada, and the U.K., and that its valuation grew from $85 million to $750 million in 2021.
That growth did not come from making barbershops “more techy.”
It came from respecting the complexity of a business outsiders underestimated.
The Frame: The Overlooked Workflow Framework
The mistake most founders make is chasing markets that already look like markets.
The better move is finding workflows that are economically important but culturally overlooked.
I call this The Overlooked Workflow Framework.
Here’s how it works.
Stage 1: Find the Industry People Dismiss Too Quickly
Some markets get ignored because they look too small.
Others get ignored because they look too messy.
The best opportunities often sit in categories that sophisticated people casually dismiss.
Barbershops.
Trucking dispatch.
Funeral homes.
Dental offices.
Immigration paperwork.
Childcare centers.
Local repair shops.
Not glamorous.
But full of transactions.
Full of repetition.
Full of operators using spreadsheets, cash, texts, memory, and duct-taped tools to keep the business alive.
That is the signal.
The tactic:
Look for industries where the workflow is mission-critical, but the tools feel informal.
If the business cannot run without the workflow, but the workflow still runs through paper, texts, calls, cash, or memory, there may be a company hiding there.
Stage 2: Separate the App From the Workflow
SQUIRE’s first idea was a consumer app.
The deeper opportunity was the shop operating system.
That distinction is everything.
Apps sit on top of behavior.
Workflow platforms become part of behavior.
An app says:
“Use this new thing.”
A workflow platform says:
“Run your business through us.”
The second version is harder to build.
But it is also harder to replace.
The tactic:
When you are studying a market, do not just ask, “What app would make this easier?”
Ask:
What happens before the transaction?
What happens after it?
Who touches it?
Where does it break?
Who loses money when it breaks?
What system does the operator trust today, even if that system is ugly?
That is where the real product lives.
Stage 3: Earn the Right to See the Exceptions
Every industry looks simple from far away.
Barbers cut hair.
Restaurants serve food.
Nurses get hired.
Truckers move freight.
But the money is in the exceptions.
The late customer.
The split payout.
The preferred barber.
The missed appointment.
The walk-in during a booked slot.
The customer who wants the same cut every two weeks.
The owner who needs to know which barber is actually profitable.
Outsiders build for the average case.
Operators build for reality.
That is why buying the barbershop mattered.
It gave SQUIRE access to the exceptions.
The tactic:
Do not stop discovery when you understand the normal workflow.
Stay until you understand the edge cases.
The edge cases are where trust is built.
And trust is where vertical SaaS wins.
The Bottom Line
SQUIRE did not win because barbershops suddenly became an obvious SaaS category.
SQUIRE won because LaRon and Salvant saw what others missed:
A barbershop is not just a place to get a haircut.
It is a business with scheduling, payments, staff, customers, loyalty, brand, and cash flow.
They did not force software onto the market.
They found the operating system already there and rebuilt it.
That is the playbook.
Find the workflow everyone underestimates.
Get close enough to understand the exceptions.
Then build the system the industry did not know it was waiting for.
Something I’ve Been Thinking About
The markets people call “too small” are often just too specific for outsiders.
Specificity is not weakness.
Specificity is defensibility.
The more deeply you understand a narrow workflow, the less likely a generic platform can replace you.
That is where the opportunity is.
Not always in the biggest market.
Sometimes in the one everyone else is too proud to study.
—
Know a founder chasing the obvious SaaS market?
Send them this.
Until next Thursday,
AP