One of the best ways to get ahead in life is to model yourself (and learn) from the most successful people in your field. In early November, 2018, I had the great honor and great fortune to interview Mr. Leo Melamed, a living legend and someone who manages to stay at least one step ahead of the crowd. Leo's story is truly remarkable on multiple levels. His personal story is extremely inspirational and his professional legacy is awe inspiring. In early November 2018, Leo was gracious enough to invite me to his office in Chicago and share his life story with me. I was able to record a portion of it - the full interview is available here. For your review, here are five timeless life and market lessons that I learned from Leo.