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She Beat Her Daughter at TikTok… Then Accidentally Became a Comedian | Kimmi Kaiy

  • May 12
  • 3 min read

What starts as a joke between a mother and daughter… can apparently turn into millions of followers and a career in stand-up comedy.


In this episode of Laugh or Death, Paul sits down with content creator and comedian Kimmi Kaiy to talk about her unexpected journey from posting dark humor videos on TikTok to performing live stand-up comedy in front of packed crowds. What began as a playful challenge with her daughter quickly exploded online, with Kimmi building a massive audience through relatable dark humor, honesty, and a style that connected deeply with people going through difficult seasons in life.


Kimmi opens up about the strange world of internet fame, dealing with criticism online, and why dark humor resonates so strongly with people who have experienced pain, anxiety, depression, or hardship. Rather than seeing humor as offensive, she explains how laughter can actually disarm difficult situations and give people the psychological distance they need to cope and heal. The conversation dives into the surprising emotional connection people form through comedy and how humor can become a form of resilience.


The episode also explores Kimmi’s transition into stand-up comedy—a move she never originally planned to make. After performing her first five-minute set “just to try it once,” she immediately fell in love with the adrenaline, connection, and energy of live audiences. Paul and Kimmi talk honestly about bombing on stage, social anxiety, crowd work, hecklers, and the emotional highs and lows that come with comedy.


Along the way, the two swap stories about social media culture, the weirdness of online comments, Minecraft obsessions, crowd work trends, and how comedy changes depending on who’s telling the joke. Kimmi also shares how reading Paul’s book The Humor Habit helped her through a difficult season and even inspired a new “laugh jar” ritual in her home with her daughter.


This episode is funny, thoughtful, brutally honest, and full of insight into why people laugh at the darkest things—and why sometimes, that laughter is exactly what helps them survive.


PS! 


One of my favorite parts of this conversation was hearing how The Humor Habit helped Kimmi and her daughter create more laughter at home.


🎧 Grab the audiobook here: Listen to The Humor Habit Audiobook 


Links:


Downloads the FREE Fun Over Funny Guide for Leaders: https://www.paulosincup.com/freegift

 

All Links For Paul: https://stan.store/PaulOsincup


Guest Links:


Facebook: Kimmi Kaiy

YouTube: Kimmi Kaiy 


If you enjoyed this episode and want to build your own humor habit, make sure to follow the podcast and share it with someone who could use a little more levity in their life.


To learn more about Paul’s work, book him for speaking engagements, or explore the science behind humor and resilience, visit: 👉 https://www.paulosincup.com You can also dive deeper into the tools discussed in this episode in Paul’s book: 👉 The Humor Habit



Episode Minute-By-Minute:


  • 0:00 – Intro: Meet Kimmi Kaiy

  • 1:00 – Minecraft obsession & escaping reality

  • 2:15 – The TikTok bet with her daughter

  • 3:30 – Viral dark humor videos & millions of views

  • 4:45 – Why she stopped reposting jokes online

  • 6:00 – Trying stand-up comedy for the first time

  • 7:30 – The adrenaline of getting your first laugh

  • 9:00 – Bombing on stage & comedy highs/lows

  • 11:00 – Social anxiety vs performing on stage

  • 12:30 – Why dark humor helps people cope

  • 15:00 – Joking about difficult topics responsibly

  • 16:30 – Dreaming comedy jokes in her sleep 😂

  • 18:00 – Crowd work, hecklers & comedy trends

  • 20:00 – Matt Rife, viral crowd work & social media comedy

  • 21:30 – Looking sweet while telling dark jokes

  • 23:00 – Her favorite audience “bait and switch” joke

  • 25:00 – Motherhood, social media & balancing everything

  • 27:00 – How Kimmi found Paul’s book The Humor Habit

  • 29:00 – The good and bad sides of social media

  • 31:00 – Online laughs vs in-person laughs

  • 33:00 – What comedy taught Kimmi about herself

  • 35:00 – Becoming a “real comedian” & final thoughts


 
 
 

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