(I realise that the question is actually about taking on someone/entity as an investor/partner) Slightly different POV: I had the opportunity to work for a co

(I realise that the question is actually about taking on someone/entity as an investor/partner) Slightly different POV: I had the opportunity to work for a company for either options, or accrue extra annual leave. I took the options. Smart people took annual leave (because it was still actually payable/real money) At the end, as it turned out we all lost our jobs anyways, people who had taken annual leave got extra money. I got a huge bunch of options. Now that's fine they may have been worth something, but I still had to exercise them. It was ok though, the CEO told us all verbally we would have 12 months to exercise them. 2 months later, I got an e-mail from the CFO asking what I was doing with my options as they would lapse in 30 days. I had to exercise them or let them die. I was already committed, so I thought what the hell, I'll exercise them because otherwise I walk away with nothing So I forked over even more money. I wish I hadn't exercised those options. They ended up being worth exactly $0.