

Lessons from 24 Acquisition Nightmares
162 snips Mar 20, 2025
Jed Morris, a former Air Force veteran and tech professional, shares his journey from military service to business acquisition and the lessons learned from his failed ventures. He discusses the pitfalls of misjudging employee dynamics and insurance costs after purchasing landscaping businesses. He highlights the importance of transparency and due diligence in acquisitions while addressing the emotional struggles of transitioning from a secure job to ownership. Jed also provides insights into the ‘little black swans’—unexpected challenges that can derail even the best-laid plans.
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Jed's Path to ETA
- Jed Morris, an Air Force veteran, discovered ETA during business school and was drawn to it.
- Despite a lucrative tech career at Microsoft, he pursued ETA due to a desire for more control and long-term stability.
Defining Your Buy Box
- Define your buy box based on your optimal outcome, not just standard criteria.
- Be flexible on criteria where your skills can compensate for business weaknesses.
Size and Salary Considerations
- Jed prioritized larger acquisitions, reasoning that the personal guarantee risk was similar regardless of size.
- He aimed for businesses with at least $500,000 SDE to cover debt and his $125,000 salary.