Rabbi Simon Jacobson is known today as a bestselling author and founder of the Meaningful Life Center. But for many years he was one of the transcribers and editors of the Rebbe’s Farbrengen. In this conversation we discuss some of the paradoxes he observed over the years, both regarding the Rebbe’s use of technology in sharing the Farbrengen around the world but also in how the Rebbe empowered his chassidim to think for themselves.