In show business, when you really have a career that takes a while, you don’t get those big moments. You don’t get those “Oh my God, it’s me” things. You get the call—“You’re playing Carnegie Hall”—and then you go, “Yeah, well, what are they paying me?” Because how you get to Carnegie Hall is you sell out Town Hall twice in a year, and now you sell enough tickets to do a show at Carnegie Hall. Carnegie Hall is a shitty deal: They have a high-paid crew, and the rent is high, and you don’t make that much money. So that moment that you think is going to be a guy in a tuxedo bringing you a pearly telephone and saying, “You’re playing Carnegie Hall”—it doesn’t happen. You have worked your way there in tiny steps, so by the time you get to Carnegie Hall, it’s as natural as playing anywhere else.
It’s also worth a read for the bits where he talks about his reticence to go down the crowdfunding route and how he enjoys testing established industry conventions. On the latter, I might borrow this line:
It’s like, there’s some joke about a guy with a banana in his ear to keep the crocodiles away and he says, “It’s working.”