Tom Segura: How to Tell Jokes | How I Write

Tom Segura: How to Tell Jokes | How I Write

From How I Write by David Perell

May 20, 2026 · 1h 14m

About this episode

Tom Segura joins David Perell to discuss the art of writing comedy and share insights on observational humor.

Tom Segura, a comedian known for specials like "Completely Normal" and "Sledgehammer", is also the creator of the TV show "Bad Thoughts". He's appeared on "Conan" and "The Late Show with Stephen Colbert". Today, he's here to teach us how to write comedy. What makes Tom's humor so distinct is its observational and story-based nature. He can look at something you've seen a thousand times and point out a hilarious detail, making you realize, "Yes, that's absolutely true!" That's why I asked him to come on the show and teach us how he finds and writes those kinds of jokes. Here's his answer, along with a few moments that had me in tears of laughter. [TIMESTAMPS] About the host Hey! I’m David Perell and I’m a writer, teacher, and podcaster. I believe writing online is one of the biggest opportunities in the world today. For the first time in human history, everybody can freely share their ideas with a global audience. I seek to help as many people publish their writing online as possible. Follow me Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470 YouTube: https://www.youtube.com/@DavidPerellChannel Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv X…

People in this episode

Host: David Perell

Guest: Tom Segura

Topics covered

  • comedy writing
  • observational humor
  • storytelling
  • podcasting
  • entertainment

Keywords

  • comedy
  • jokes
  • writing
  • humor
  • story-based

Mentioned in this episode

Books & works: Completely Normal, Sledgehammer, Bad Thoughts, Conan, The Late Show with Stephen Colbert

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