Year: 2009

Buyout offer: $800 million from Apple

What happened: After Drew Houston, a young MIT graduated, managed to get his nascent product cloud storage product to work seamlessly with Apple's file system, Steve Jobs took immediate notice. He invited Houston and his partner, Arash Ferdowsi, to Cupertino where he tried to convince the duo to sell. According to Houston, Jobs said Dropbox was a "feature, not a product", and that Apple was planning on entering that market. Houston and Ferdowsi declined Jobs offer. Shortly after, Apple released its Dropbox competitor, iCloud. Don't feel too bad for the Dropbox dudes-in 2011, after a venture capital round that raised $257.2 million, the company was valued near $1 billion, with analysts saying it could very well rise in the future to $5 billion.