Second Shot With Heath Oakes

"Sometimes, when you think about yourself as a number two, you're really a number one." Often when it comes to change, there has to be someone willing to ask the question "Why are we doing things this way?" That was the case when Dr. Tye and Courtney Caldwell looked at the salon business, and rather than stop at asking that question, they did something about it. They are the cofounders of ShearShare, the first on-demand salon and barbershop space rental app. ShearShare is the first Texas startup to win Google Demo Day, L’Oreal’s Women in Digital NEXT Generation Award, and Tech. Co’s Startup of the Year. The Caldwells’ work has been featured in the New York Times, the Washington Post, Fast Company, Forbes, Black Enterprise, Modern Salon, and Salon Today. They are alums of YC Fellowship and 500 Startups, two world-renowned programs for creating top-end entrepreneurs. But all the accolades couldn't have come without one big leap away from a comfortable lifestyle and putting it all on the line for an idea