Do you want to be a restless loser or a wealthy, generous winner? In this episode, I share the incredible experience of surprising my dad with a 1965 Shelby Cobra, fulfilling his lifelong dream. I talk about how good it feels to work yourself into a position that allows you to do really cool things for people you care about; and Amanda May and I dive into the rollercoaster of emotions that making money can be, discussing how wealth and generosity intertwine in creating true fulfillment.