The video of Chip Kidd.
How Freelance works. Even for someone who has done this for 29 years with numours awards under his belt. Watch from 15:25-22:00. Even after 29 years he has to let a freelance cover go because it doesn't work for the author, publisher, or himself.
I spent a few days looking at all the work he's ever done and all the videos I could find. Not only did I enjoy watching the evolution of book covers but the clear improvment of public speaking (Which I hate doing). Of everything I found, I think this was my favorite overall.