How much do Uber drivers really make? The Silicon Valley/San Francisco ride sharing start-up boasts that its drivers make "life changing" money--up to $90,000 a year in New York. However, Business Insider and CNN Money are finding that drivers do not come close to that amount, and Uber has been banned in several countries and cities like Portland for violating regulations. Will the company be viable long term? We explore. In the Q & A segment, one of the top CFPs and an editor for the Journal of Financial Planning, Michael Kitces MSFS, CFP joins the A-team to discuss the problems with Monte Carlo projections.