Dr. Paul Wilmott from the quantitative finance website, Wilmott.com returns with comments on his latest magnum opus, strongly endorsed by financial legend Nassim. The duo engage in an enthralling discussion on the true nature of financial risk versus the expected risk predicted by traditional econometric models. The guest and host concur, the financial field is deluding itself with seemingly solid theories that simply do not account for the reality of black-swan like events / sea-changes. Nevertheless, the duo applaud economists / financial engineers for attempting to model the complex / chaotic field of human behavior vs. the more predictable natural sciences. The discussion includes the Millennial Prizes, including P vs. NP and The Navier-Stokes prizes. In an interesting twist, the financial theorist (guest) outlines the ramifications of algorithmic trading while the financial experimentalism (host) presents his findings from his 3rd party documented 89% win rate on over 600 trades.