Chertavian started his career on Wall Street, working for a commercial bank. He also volunteered as a Big Brother during this time. Looking back, he considers working with Big Brother a life changing experience, seeding his vision for Year Up. Soon after attending Harvard Business School, he co-founded a software company. The company thrived, opening many opportunities for Gerald. A merger with a public company worked out well for Chertavian – allowing him to execute on his dream, Year Up, a second act changing the world!