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Revisiting the claim on whether he is Bipolar II: many drugs can prompt bipolar-like behavior. There's a distinct diagnostic code for this case, which is: bipolar, not otherwise specified. That is, even if he has undergone manic episodes (which I haven't witnessed, as a sufferer of the occasional manic episode), he wouldn't necessarily be classified as Bipolar I, even fitting the diagnostic criteria for Bipolar I. Though again, I haven't seen any manic rather than hypomanic behavior.
Going on my own speculation journey, given the strong biohacking/cognitive enhancing culture in the valley's tech community, I'd be pretty surprised if there weren't stimulants in the mix too. TRT has been on the rise which also can tremendously increase impulsivity and risk-taking behavior. I think the "crazier late at night" phenomenon is better explained by a drug taken earlier in the day wearing out over the course of the day than something like rapid-cycling.