When Jill Smoller's professional tennis career came to an end, she relied heavily on her ability to connect with people to help take her career to the next level. When Richard Williams gave her an in with working with his daughter Serena, she turned what was then considered a small opportunity into a decades-long partnership with the tennis legend. In this episode, Rich sits with Jill to discuss her storied career in pro sports, how there's more to being an agent than riding the highs and her belief that common sense always wins out.