Daily Insomnia Ep.375 - Kat's Dilemma

In this ep the drink of the podcast was rum & coke, and we kick off the year the right way—with award-winning comedian Kat Diaz in the room. We jump into the Chicago comedy scene and the whole awards conversation—what it means, what it doesn’t, and why we might end up creating our own just to stir the pot. Then it turns into real shop talk: what actually makes a comedy show work and all the little details that separate a solid night from a great one. We debate the question every producer argues about: is 7:00 PM a perfect time slot, or is it too early for people to really be ready to laugh? Kat takes it left with her “perfect man is blind?!” theory, and then we get into a real moment—four years sober? It’s funny, honest, and a strong start to the year… and we definitely go plenty of other places too.

You can listen to Daily Insomnia Ep.375 - Kat's Dilemma online on Radio and Podcast. Open the player on this page to stream the available audio.

Daily Insomnia Ep.375 - Kat's Dilemma is an episode from Daily Insomnia Podcast by Daily Insomnia.

This episode is 65:15 long.

This episode was published on Jan 15, 2026.

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