Early Career
Gerstner began his entrepreneurial career when he founded his first start-up called Wawasee Boat Care in Lake Wawasee, Indiana, in May 1986. He also served as chief boat washer in his company. He owned and operated Wawasee Boat Care for more than three years. As per Gerstner, his first start-up was not successful financially but believed to keep entrepreneurship in his life.
Law Career
From May 1996 to December 1997, Gerstner served as a junior lawyer in the venture capital, securities, and corporations sections of Ice Miller, one of the largest law firms in Indianapolis, Indiana. In January 1998, he was appointed as Deputy Secretary of State of Indiana, where he had to manage the Indiana divisions of corporations, securities, and elections. After serving there for one year and ten months, he quit his job to attend Harvard Business School.