Professor Jacob Bekenstein was known not only for his brilliant and original physical ideas, but also for their clear presentation in his lectures and seminal research papers. I here provide a short review of Bekenstein's pioneering ideas about the quantization of black holes. I also describe my attempt, as a young and extremely naive student, to prove him wrong and how I got convinced in the correctness and utility of his deep physical intuition. Finally, my personal contribution to the ongoing attempts to understand the evenly spaced (discrete) area spectrum of quantized black holes, as originally suggested by Bekenstein in the early days of his scientific career, is described.