Have your parents ever tried to live vicariously through you? For our guest today, that was what most of his early-life was controlled by: another person's desires. Ian Winer is an investment expert and a frequent contributor on CNN Money, Fox Business, BBC, The Wall Street Journal, and The Financial Times. He took his skills in the hockey rink to WestPoint and was eventually led all the way to Wall Street. In this episode, we talk about how Ian was able to reclaim his identity, and what it actually means to be successful, by embracing fear and setting out on an adventure of self-discovery that gave him a new perspective and purpose in life.