8. Google

Year Purchased: 1998
Estimated Value: $1.885 trillion* 

Google currently has a market cap of nearly $2 trillion, making it one of few companies to achieve this feat. In 1998, things looked a lot differently for Google. The tech company’s headquarters, run by Larry Page and Sergey Brin, were in a garage in Menlo Park, California.

Jeff Bezos saw something in the tiny company, and he invested $250,000 into the venture. The investment in the startup is now up 20,000% today, and Bezos has cashed in on his now 3.3 million shares of stock. These shares are worth over $3 billion today. Bezos’ Google investment is yet another example of how his belief in tiny startups has made him billions.