After college, Mr. Dillard worked as an auditor at Coopers & Lybrand, gaining the experience required to be a licensed certified public accountant. While at the firm, he realized that his career interests lay in the nonprofit sector and soon found work as an auditor at the IP Foundation, the philanthropic arm of International Paper that provides grants to nonprofit organizations.

In the early 1980s, Mr. Dillard returned to Operation Crossroads Africa as its director of finance. Although Mr. Dillard said he had found being employed by that organization rewarding and enjoyed traveling for work to West African nations like Nigeria, his tenure there lasted less time than he would have liked because of a management shake-up a few years after his arrival.

After Mr. Dillard left the organization for a second time he struggled to find steady work. In 1990, Mr. Dillard began the first of several part-time accounting jobs at the National Foundation for Teaching Entrepreneurship, a nonprofit organization. By 1995, he found steady, but part-time consulting work for the New York Conservatory for Dramatic Arts through a temp agency. He came close to finding a full-time job in 2001, but the offer was rescinded two days after the collapse of the twin towers.

“They didn’t need me or they had other issues that they needed to tend to,” Mr. Dillard said. “And then that was pretty much around that time there were no jobs being offered.”