When it comes to a business that produces your livelihood, I have always treated this situation like gambling: Don’t risk more than you can afford to lose. That doesn’t mean avoiding risk, that means taking smart risks and making sure they won’t sink you forever if the worst happens.
Fishthumper has a great example of taking a smart risk in a business he clearly understands.
Mrs. Grouse had the chance to accept equity in a company she worked for in lieu of a significant portion of her salary. We talked a lot about this because it was a large chunk of income that we would be risking, but there was also the potential for a reward if the business continued to grow as it had and the owner executed his plan to sell to a much larger competitor. For us, the deciding factor was what if the worst happens and we lose her equity? The answer was it would have been a really bad deal and would hurt really bad, but financially we could get by and recover. We weren’t going to lose our house or end up bankrupt, so we went for it.
The worst situations I’ve seen in business was when people risked money getting into businesses that they didn’t understand and that were controlled by other people. Even worse was when people did this and risked money they couldn’t afford to lose in the first place.
But whatever you do, do not get into crazy stuff like crypto, Zimbabwean gold futures, or hardwood flooring.
Grouse