The best way to come up with joke ideas
Also: Why you shouldn't get jealous of other people's success and other tips for beginner comedians.
Some excerpts from an interview I did:
Q. If you have your own stand-up master class, what would be your tips to a beginner?
Some tips: Perform as much as you can, watch/listen to great comedians, align what you talk about onstage with what you talk about offstage, make friends with your peers, think like a craftsman, figure out a healthy relationship with alcohol (because you’ll be surrounded by it), don’t be afraid to take a harder/longer path instead of seeking shortcuts, and don’t be jealous of other people’s success because everyone’s on their own path.
Q. What is your way of delivering a joke?
My favorite way to come up with bits is to have conversations with friends and wait for something to come up that feels like a fresh take, gets me animated, or feels juicy in some other way. I carry a notebook (and use the Notes app on my phone) to capture those ideas in the moment. “Hang on, I gotta write that down.”
Later on, I’ll flesh it out as an idea and, if it feels like there’s something there, try it onstage. Most of the time, they’re not actually strong enough to work as jokes.
Every once in a while, a joke comes out fully formed; but that’s rare. Usually, you’ve got to chip away at it for weeks (or even months) before it’s solid. The audience teaches you via laughs which ones are worth hammering away at until they’re actually funny enough to stick in the set.

Q. There are many comedy clubs all over New York City. What are some of your favorites and what advice would you give to the first-timers to the city who are interested in catching a live stand-up comedy show?
I perform most frequently at the Comedy Cellar (including every Tuesday night at Hot Soup) and NY Comedy Club (including every Wednesday night on Good Eggs). Those are the best places to see a quality show that delivers a real NYC standup vibe.
Some tips: Get tickets in advance since shows frequently sell out. And weeknights are your best bet for bigger names to drop-in on a show since they’re often on the road during weekends. And if you sit in the front row, be prepared to answer if you’re dating the person accompanying you. That happens at about 80% of shows. (Note: If you’re with someone of the opposite sex and you say you’re just friends, the host will say one of you is trying to have sex with the other and everyone in the room will explode in laughter because for some reason unrequited love is the funniest thing to human beings.)