8 – Apple Stock Sold by Ronald Wayne
Along with Steve Jobs and Steve Wozniak, Ronald Wayne was one of the founding trio that set up Apple in the first place. He even came up with the logo for the company and took control of a wide variety of crucial introductory business matters for Apple. However, he was so convinced the business would fail that he decided to cash out, rather than risk losing out. When he did, he received somewhere in the region of $2,300. If he’s stayed put, his stock would have been worth around $35 billion as of 2011. Ouch!