Amos Paul Kennedy Jr. is an internationally recognized printing press artist, though he would rather be referred to as a "humble negro printer." This self-proclaimed "humble (sometimes lowly) negro printer" tossed aside his corporate 9-to-5 job at AT&T with its steady income, chooses to live in extremely rural Alabama towns and goes wherever his art takes him. Amos found his calling making chipboard posters he sells inexpensively, so anyone and everyone can afford his art. His posters are socially, politically, and racially charged: with quotes from Sojourner Truth, Rosa Parks, and phrases like "coffee makes you black." The documentary film Proceed and Be Bold! probes Kennedy, his friends, family, and colleagues in an attempt to unravel the artist's meaning. The result is a discussion on the monetary and intrinsic values of art, the goals of an artist, the workings of race and culture, and what "the American Dream" really means.