Rock star, crowdfunding pioneer, and TED speaker Amanda Palmer knows all about asking. Performing as a living statue in a wedding dress, she wordlessly asked thousands of passersby for their dollars. When she became a singer, songwriter, and musician, she was not afraid to ask her audience to support her as she surfed the crowd (and slept on their couches while touring). And when she left her record label to strike out on her own, she asked her fans to support her in making an album, leading to the world's most successful music Kickstarter.
For additional material on Amanda, check out this wonderful interview on the Tim Ferriss Podcast.
As a bonus, Amanda is married to one of my favorite authors, Neil Gaiman.