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After watching hours of digital drawing and painting videos on Youtube, and watching notch code the other day on Twitch, I can definitely agree this is an interesting vertical to explore.
Take some more time off for Lisp hacking!
Hah! As it happens, I had just started experimenting with designing a new Lisp dialect when I got Emmett's email! It was working out pretty well, and I was having a lot of fun, but I think the world needs livestreamed creativity more than it needs yet another Lisp :)
The OP only mentions the below in passing, but I thought it was one of the more interesting parts:

"A former coworker offered me a job as CTO at a startup he'd left justin.tv to found. That seemed like just the kind of thing I was looking for, but after nearly a year it was clear it hadn't worked out."

I'd be curious to hear more about what happened. If somebody were to offer you a similar opportunity again today, what characteristics would you look for in that person (and company), and how would you test them?