Passage to Profit Show - Road to Entrepreneurship Entrepreneurs: What Was Your One "What Was I Thinking?" Moment?
Sep 9, 2025
This discussion is filled with laughs as entrepreneurs share their most cringeworthy "What Was I Thinking?" moments. From hiring blunders to chaotic grand openings, they reveal how these missteps transformed them into more insightful leaders. One story highlights the pitfalls of contractor miscommunications, stressing the importance of thorough contract reviews. Each anecdote serves as a reminder that mistakes are essential stepping stones on the road to success, proving that even the most challenging moments can lead to growth.
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Hiring Revealed Leadership Gaps
- Kenny Lange hired employees in his first company and realized leadership matters once work quality fell and people left.
- He wondered why he moved away from hands-on work and how to lead effectively when others depend on him.
Don’t Rely On Magic Bullets
- Avoid expecting an external “magic bullet” to fix major business problems.
- Do the messy work yourself because no one else will fully carry your company's responsibility.
Skipping Background Checks Backfired
- Whitney Dueñas Richardson hired a fitness instructor without a background check and faced bad publicity when the hire got in trouble.
- She regretted hiring quickly at 19 and learned to vet contractors before opening a business.