To me this seems to be a story of addiction. The "three" people that are "Jeff" include 1) the actual Jeff, a shy introvert with way too much on his plate, 2) an intoxicated Jeff that is outgoing and highly functional, 3) a Jeff that is unrecognizably intoxicated (Michelle).

The part where I have a hard time reconciling the story is towards the end;

> I tell her it’s likely not that and then call Michelle. It isn’t difficult to track her down — she has a robust web presence. She says that she is no longer working with Jeff and has no idea where he is.

I'm thinking that the author calls "Michelle" (aka: super intoxicated Jeff) who is hitting "jackpots" all over the news who basically tells the author off completely, indicating that he is never coming back / losing his battle with addiction. Or perhaps "Michelle" has moved on because "Jeff" has moved on to harder substances in harsher circumstances.