After an independent stylist asked to rent out a chair in Courtney and Tye Caldwell’s Plano, Texas, salon, the husband-and-wife team knew they had a bead on something valuable. Soon, the Caldwells found themselves helping stylists find empty spaces in salons across the country. For three years, they handled the matchmaking themselves while also meeting the demands of their day jobs–Tye managed the salon and Courtney ran digital marketing strategy for Oracle. In 2015, they automated their side hustle with the ShearShare app. In the four years since, the Caldwells have done a stint at Y-Combinator, raised $1.1 million in funding (with another $2 million anticipated this fall), hired 11 new employees, and expanded bookings to nearly 500 cities across 11 countries. In July, ShearShare debuted a tax assistance feature for self-employed stylists. “We get the ebbs and flows of owning a small business in this industry,” Courtney says. “Our customers stand by us because of that. It’s rare.” –Cameron Albert-Deitch