I expect to have a conversation with Nassim Nicholas Taleb, author of Fooled by Randomness and The Black Swan, in the next couple of days. He’s a very smart and talkative fellow, and I suspect he would fit into a Freakonomics Radio podcast very well. What would you like me to ask him?

Given his high regard for NYT, can you ask him if he would miss your column should NYT somehow vanish ?
ask him if he sees black swans in his dreams
Love the Black Swan, but how can “regular” people implement these concepts into their lives? How can an “average” person invest their 401k, their bank savings, etc., to make the most of their assets while avoiding the risks that they assume by just being part of the “marketplace”?
Given his passion for lots of slow, reflective walking and learning from our ancestry, and given the recent press about the virtues of barefoot walking and running, does he own a pair of Vibrams Five Fingers? If not, what is his favorite walking shoe?
Ask him if he has found it increasingly difficult to follow his investment strategy of betting on long-tail risks given the success of said strategy during the financial crisis. Are people now overpaying for “black swan” events or can it never be priced fairly so long as options are based on the Black-Scholes model?
If you agree that real estate appraisals fit in the same category as economic forecasts, how can their effects on loan underwriting be robustified? Why do people, including those who should know better, put so much trust in them? Also, since real estate values are so prone to both black and white swans, is it wise to base property taxes on such bogus forecasting?
What are the books he would recommend to a general readers – perhaps some that would attempt to match his famed combination of math, psychology, philosophy, and Finance?
What are the books he would recommend to general readers – perhaps some that would attempt to match his famed combination of math, psychology, philosophy, and Finance?