This is especially awesome since Shiller, along with Eugene Fama and Lars Hansen of the University of Chicago, won the Nobel for their work on the reality of accurate asset pricing on the near and long term.
Lofty stuff, but here's how you can grab some of Shiller's extensive knowledge for free: Back in the spring of 2008 (yep, right as our economy was starting to crash), Shiller recorded 26 free podcasts on topics ranging from options markets to portfolio diversification - they're up on iTunes for you to enjoy.
Here's the description of the
(ECON 252) Financial institutions are a pillar of civilized society, supporting people in their productive ventures and managing the economic risks they take on. The workings of these institutions are important to comprehend if we are to predict their actions today and their evolution in the coming information age. The course strives to offer understanding of the theory of finance and its relation to the history, strengths and imperfections of such institutions as banking, insurance, securities, futures, and other derivatives markets, and the future of these institutions over the next century. This course was recorded in Spring 2008.