Jack Cundiff works a day job at a Midwestern hardware store and runs his own handyman business on the side. He wants to spend more time with his two kids as they grow up, yet Jack doesn’t know if his own business would allow him to adequately provide for his family. When Jack takes his family on a long-awaited vacation to Mexico City, he meets an old friend from high school who shows him what it takes to be self-employed.

Will Jack quit his job to make the leap as a full-time business owner?