"The Dilbert Principle," by Scott Adams. "Scott Adams is a premier organizational behaviorist, and his work helps me understand how and why large organizations normally become increasingly dysfunctional over time. As a result, we have some clues as to how to prevent that from happening at Craigslist."
"The Future of Freedom: Illiberal Democracy at Home and Abroad," by Fareed Zaccaria. "This book helps me understand global political currents that indirectly affect craigslist as we're subject to disinformation attacks, and how to understand and deal with them."