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Tom Segura has been doing stand-up comedy for ~25 years. He's known for his Netflix specials and a TV show called Bad Thoughts. His stand-up sets are based in stories and simple observations around the world. The guy can look at something you've seen a thousand times but never managed to find the humor in. At one point during the interview I was laughing so hard that I could barely ask the next question. I asked Tom how he finds jokes, develops stories for the stage, what he's learned from Chris Rock, and how to turn ordinary observations into comedy. Timestamps: 0:37 How to find jokes 2:03 Why are comedians always annoyed? 7:19 Say the obvious 11:06 What makes a joke land? 13:11 The 250 rep rule 15:07 Chris Rock 19:33 The 4 types of comedians 21:44 Use the audience's discomfort 24:39 The key to good stage presence 32:00 Mall cops and TSA agents 36:50 How to develop a joke 38:56 Stand-up vs. TV writing 49:11 Finding your way into the story 54:08 Punchlines 55:16 What a set list looks like 58:15 Word choice 59:31 Accents 1:03:50 How to start a show 1:08:01 Writing a book Some things he taught me about being funny: 1) The best mindset to bring on stage is silliness. 2) You must have strong opinions. Indifference kills comedy. You can say "this is the best coffee I've ever had" and make it funny. You can say "this is the worst coffee" and make it funny. But "it's fine, I don't care" is never funny. 3) You can tell the difference between a world-class comic and an amateur one by their relationship with silence. Amateur comics get jittery if a few seconds pass without laughter, whereas seasoned comics use it to their advantage. 4) Good word choice matters more than you'd think. "Yanked" is a funnier word than "pulled." Yiddish words are funny. An easy way to pick up on this is to listen to how naturally funny people describe things. 5) How to find jokes? Talk all the time. Talk and talk, and develop the skill of recognizing when something you've said has legs. I've shared the full episode with Tom Segura below. If you'd rather watch on YouTube, or listen on Apple / Spotify, check out the reply tweets. @tomsegura