Do you sometimes sit down and wonder how the products and services you use every day got their start? For some, it wasn’t a straight path to success. Whether it is difficulty accessing funding or a necessary rebrand, startups aren’t always successful overnight.
And no better way to learn this by examining how successful startups came to be. Songe LaRon and Dave Salvant are a true representation of this. Both New York City natives, they recall going to barbershops nearly weeks since the age of six, watching the men in their lives get haircuts.
After spending time working in banking and law, they found themselves drawn to entrepreneurship, and the lack of change in the barbershop experience caught their immediate attention. So began the building process of Squire, a barbershop point-of-sales and management system.
When the two started Squire Technologies in 2015, they paid a graffiti artist a few hundred bucks to scrawl “Download Squire; on the streets of Manhattan. Of course, this was a low-cost bit of guerilla marketing for their struggling barbershop looking app.
They’d signed up about 50 barbers at eight or nine shops by going store-to-store talking with owners, but with so few customers downloading the app it was largely useless. Worse, the barbers complained that Squire’s app wasn’t helping them run their stores.
The Zigzag Line From Idea to Execution
Neither of the two had worked in a barber shop before or run a small business of any kind. In 2016, they made a bold move: They spent $20,000 of the $60,000 they had on hand to buy out the lease on an ailing barbershop in Manhattan’s Chelsea Market.
“That gave us a test kitchen to develop the software,” recalls Salvant, the company’s president. “This was a huge gamble.” They didn’t cut hair but ran the front desk, swept hair off the floor, talked to customers, and ordered supplies.
The risk paid off, eventually. They learned the intimate challenges of running a barbershop, from running bookings to paying individual barbers. With this knowledge, they decided to pivot from targeting end consumers, a model known as B2C to targeting barbershop owners, a model known as B2B.
This focused on the owners as the primary customer and building a software as a service, or SaaS, platform to meet their needs. Even though their initial focus on end consumers might be regarded a failure, it proved an important lesson for their customer value proposition.
The new platform took off. Squire’s goal was to offer an easy to use, end-to-end system tailored for barbershops, covering everything from booking to online payments, point of sale, back-end activities, CRM, financial services and marketing.
Squire is now available in three countries and has raised $165 million in funding, driving home the message that taking the time to understand your customers pays off. Not to mention, it has gained acceptance into Y Combinator after facing two rejections. For those who may not know, YC is the most prestigious startup accelerator.
After YC, growing Squire was a trial-and-error process, LaRon revealed once. He and Salvant had to learn what actions actually led to growth. The two honed in on best practices for measuring Squire’s success with highly specific metrics, figuring precisely what was moving the needle for the business.
Squire reached nearly three thousand establishments in the U.S, Canada, and the UK, and Forbes Magazine included the company on its ’25 next Billion-Dollars Startups’ list. Squire’s journey was a rollercoaster; they faced financial challenges three times but successfully turned the situation around.
