Yeah what you described is called the volatility smile.

I would say going long on Black Swans is more of an insurance policy unless you are a VC. As the Taleb advised Universa Investments L.P. sells itself as "an investment management firm that specializes in hedging tail risks for its clients. Universa has a focused investment approach employing positively-skewed payoffs, empirical and fundamental-based option valuation, and order flow trading."