My best investment decision is also my worst investment decision. I worked at a start-up VERY early and got a ton of stock options. I exercised about $10,000 in shares at about $0.10 a pop about 10 years ago. The start-up is now a nicely sized company that prints money. I've received about $450K in dividends. Though the company is still private, shares I own are probably worth about $2.00/share. I'm praying they sell the company soon.
On the downside, I had the opportunity to buy many more shares. If I had bought more, I'd be a millionaire. But when I bought the shares for $10K over 10 years ago, I was like, "damn...that's a lot of fucking money....I'm not spending $30K on this..."
So on one hand I'm happy, but on the other hand I'm like "daaaaaamn, I should have bought more!"
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