Dividends & Income Digest: What Is The Biggest Investment Risk You've Taken?

Risk is inherent in investing, and during more than a decade of helping successful investors share their stories, I've found that it's when they've put their necks on the line - regardless of the result - that they've learned some of their most important lessons.
No one has a crystal ball, and when you gamble, you sometimes lose. But as many dividend investors can attest, the best opportunities often present themselves when the near-term seems least certain.
This week's Digest poses the question: What is the biggest investment risk you've taken, and has it paid off?
Please share your own thoughts in the comments below.
Regarded Solutions
I sure do remember the biggest risk I ever took! I didn't think of it as a risk when I did it, but it sure turned out that way!
Back in 1983, before I wisened up, I was given a "tip" that the toy manufacturer, Coleco, was going down the tubes and would have a miserable Christmas season. I did some research, and the company was bleeding cash, losing sales, and chasing its biggest rival at the time, Atari. I didn't have much to spend on shares, so I bought put options with my emergency money fund, just out of the money options, betting that the share price was going to crash bigtime! Not long before Christmas season began, the company made an announcement that I was hoping would be about filing for bankruptcy, but boy was I wrong! The company unveiled its newest blockbuster product,... Read more