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Caleb's feature length directorial debut, Connect, a documentary about social media, was released theatrically nationwide in 2018 and was picked up by Netflix shortly after. In 2019, Caleb created "One on One" an on-the-go interview show featuring a diverse cast of guests which was picked up by Netflix. In 2022 his next documentary, "The Homeschool Awakening" was released theatrically nationwide.