In this episode of The Confessional, Roger Mitchell sits down with Ray Ranson for a frank conversation about the move from football to business, and the harder lessons that came with it. Ray reflects on the ruthless side of life in deals, the pressure of keeping a game face, the painful lesson of backing a pioneering sports tech deal that had the vision but not the pricing power to match. It’s a conversation about ambition, regret, and the cost of getting things wrong before you finally learn how to get them right. Brought to you by Lockeroom.