Woolsey was born in Tucson, Arizona. As the son of Christian missionaries, he grew up in Arizona, Peru, Ecuador and Guatemala.
In 1989, Woolsey earned his B.A. in Spanish from Louisiana State University. Upon graduation, he worked as a Spanish teacher until joining the United States Navy in 1998. Following his discharge from the Navy in 2002, Woolsey has worked as a bilingual teaching assistant and a janitor. He currently works as a retail associate at Marshalls.
Woolsey submitted the following statement to Ballotpedia:
|“||On February 15, 2014, I was led by the Holy Spirit to run for Governor of Arizona. On March 7, 2014, the Secretary of State of Arizona accepted the statement of organization for my political committee, 'Arizona for Woolsey for Governor,' commencing my candidacy for Governor of Arizona. By the time my period as leader of Arizona ends, pre-birth killing (abortion), court-ordered medicine, the forbidding of preaching Jesus Christ and the forbidding of Bibles in public schools will be legally ended, or there will be no God in heaven and I will take full responsibility for these restraints on life, liberty, and the pursuit of happiness remaining.||”|