Hmm this is one area that I guess doesn't make me a good entrepreneur, I have discovered that I don't like to take risks, I love playing safe and as such never invested in any high risk investment schemeI haven't made many high risk like investments in my life. I have done a few, but it's only when I knew it was something I felt comfortable investing in. I do a lot of research and take my time with it. I never rush when it comes to investing.
But... Around 10 years or so ago. I invested $5000 of what I had made on a recent temp job, into starting this new business. I don't want to go into detail about the service, as I still may try to invest into the idea again. But, I'm sure you guessed right by this point, but that $5000 was gone, I made no return on the investment and was out of everything. I had like a couple hundred to my name after that. This of course was when I kind of started working, and making good money.
It was a major blow, but I thankfully recovered. I still feel like crap every time I think of it. But I have to remind myself, because I never want to repeat that mistake again.