Pros
Small organization with big egos. If you have a loud mouth and can schmooze, you will do well. You will earn a Post-Doctoral Degree on Office Politics.
Cons
YPO is a very small non-profit organization. That thinks it is a Fortune 100 organization. The demands and requirements, it places on IT and applications is completely out-of-whack with reality. YPO demands a Lamborghini on a Chevy Nova budget,. You get what you pay for. Incompetent vendors. Rube Goldberg applications that miraculously somewhat works. Senior Leadership is technically clueless and proud of it. When a vendor or consulting company fails due to incompetence or lack of oversight... nothing to see here. Business as usual. Permanent management staff either aids and abets or is asked to clean up the mess. Depends on the direction the wind blows.