Penelope Trunk’s book is Brazen Careerist: The New Rules for Success, about which, in her Cool Friends interview, she says, “I thought my audience was young people in the workplace. But, in fact, management loves buying my book. They buy it in huge quantities to understand how to recruit and retain Generation Y.” Through her column of the same name featured on Yahoo! Finance and her column “The Climb,” which runs in the Boston Globe, Penelope has established herself as an authority on Generations X and Y, how they work, and how Baby Boomers, et al., can work with them. She speaks from experience, having gone through two start-ups, an IPO, an acquisition, and a bankruptcy. And before any of that, she was a professional beach volleyball player!