Angela Ruggiero is a four-time Olympic ice hockey medalist, USOC and IOC Board member and presently, the CEO and Co-Founder of the Sports Innovation Lab, focused on the convergence of sports and technology. Our conversation spans her personal fandom of Serena and what it felt like interacting directly with her fans for the first time (circa 2009 via twitter), to the fluid fan. We explore personalization and winning in today’s “attention-economy”.