They walked away from six-figure jobs in law and banking to buy a struggling Manhattan barbershop; and learned the business from the inside out.Songe LaRon was a corporate lawyer. Dave Salvant was a private banker. Neither had a tech background, but both had grown up watching how much a local barbershop mattered to its community; and how outdated the business behind the chair still was.So in 2016, they did something most founders never would: they bought a barbershop license for $20,000 and ran the shop themselves for a year. Not cutting hair, but living every other part of the business; the scheduling chaos, the cash-only payments, the double bookings. That firsthand frustration became the blueprint for Squire.What started as a scrappy booking app; marketed at one point by paying a graffiti artist to spray “Download Squire” around Manhattan; has grown into an all-in-one platform for barbers: booking, payments, payroll, marketing, inventory. Today, Squire powers thousands of shops across three countries, has processed over $1 billion in payments, and is valued at over $750 million.In 2025, LaRon and Salvant won the EY Entrepreneur Of The Year Award for the New York region.Their story is a reminder that some of the best businesses don’t come from a whiteboard; they come from actually living the problem you’re trying to solve. What’s a business you think could use this same “get in the trenches first”
