The limit doesn't matter so much as striking it in the first place. Realistically, all of the mentioned investments are within the realm of reasonable thought. The presumption of a black swan is that it is completely outside the ability for one to rationally assess a system then predict it with decent success. 5/40 would be a phenomenally high success rate.

Lottery is totally not black swan, which is exactly what I was trying to say. Despite having prior knowledge of the company's situation (unlike a completely random lottery), it seems to me that these investments are closer to the lottery than black swan.

You don't place bets on a specific black swan, but you could place a different, outside bet on a disrupting event (kind of the idea of antifragile, benefiting from disorder). I think under Taleb's comments in Antifragile, living life as an artist as opposed to someone who is inherently reliant on the stability of say, an office job, is placing that bet every day.