True, risk adjustments can be made to modify those bounds in real markets, unlike with actual lottery tickets where you have no control over the upside and expectation of winning. But the idea is still very similar in it's basic strategy.

Given Taleb's understanding and belief in randomness of the market, I see him as "creating his own lotteries" using rather sophisticated techniques that have paid off very well. The cost of entry is small and the potential rewards are high but he loses regularly and consistently and says he was grateful to be in a position where he could execute such a strategy without being looked down upon by his superiors (from Fooled By Randomness).