Caspar Berry had an early career in television before studying at Cambridge University. He then pursued screenwriting and had success getting scripts produced. He later spent three years as a professional poker player in Las Vegas, where he learned lessons about risk-taking and decision-making. After returning to the UK, he co-founded a media company that he later sold. He began speaking to businesses about applying poker strategies to decision-making using his experience in the game. He has since delivered over 1,200 speeches to companies on embracing uncertainty and calculated risk.