I was overcome with conflicting emotions while reading this. I have had 2 start ups and one Family business that I took over. Not one failed but they never turned out to be “successes”. Fortunately I never ended up owing anyone anything but I did however experience some of the emotions your ex-boss experienced. My toughest experience was when I had to let 4 people go out of my 25 person team at the family business. My advisors and family could not understand my resistance to letting people go and explained to me that it was not a personal decision. I guess my biggest concern was the guilt I had because the decisions that got us in this tough spot was made by me, however things out of my control happened. On my biggest project to date our lead engineer disappeared with my deposit and is still at large, we were so invested that we had to go ahead this was the biggest mistake. We over invested and kept throwing money in hoping for the success what would have been an industry first in South Africa.
It never did and I made a decision to sell the business to our largest customer. I figured after 1 year of constant struggle to stay afloat, working short time, the emotional burden of the welfare of my staff and my rising debt to save the business it was time to step back and go back to “school”.
My entrepreneurial spirit has been “crushed”, I say crushed because I have learned that people mean more to me than a company and a product. I guess as an entrepreneur I wanted to share this because I genuinely thought my business decisions were going to be the best for everybody, as it turned out we survived and are all stronger and wiser for it.