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.