Earn Your Happy

Our Funniest & Most Cringe Mistakes as Entrepreneurs (+ How to Recover When Things Go Sideways)

Sep 9, 2025
The hosts dive into their cringeworthy entrepreneurial blunders that once felt catastrophic but now serve as comedic gold. From Chris’s on-camera meltdown to mix-ups during interviews, they share how humor can lighten heavy moments. They talk about their early podcast tech disasters and stress the importance of resilience while learning to embrace imperfections. Discover how to transform your own mistakes into powerful lessons with the help of a supportive network.
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ANECDOTE

When Production Fits Go Wrong

  • Chris and Lori pre-recorded a high-production course called Aligned and Chris repeatedly had on-camera tantrums while trying to hit scripted lines.
  • An editor missed one out and the unedited profanity landed in a paid module, forcing them to take the course offline and re-edit quickly.
ADVICE

Fix Fast And Let Embarrassment Pass

  • Fix mistakes immediately and keep a sense of humor while embarrassment passes through you.
  • Don't overreact; correct the error quickly and move on.
ANECDOTE

Calling Your Guest The Wrong Name

  • Lori interviewed Natalie Ellis but called her 'Danielle' repeatedly through a full podcast episode without Natalie correcting her.
  • Lori realized after the recording, felt mortified, and had to ask editors to edit out the wrong-name mentions.
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