Much of the first generation of Internet businesses blew up in the Dot-com bubble back in early two thousands, while there were much crticism in mass media, a few books like eBoys by Randall Stross has given some interesting accounts of events leading up to the bubble bursting.
Even though the fall out of the Dot-com bubble was pretty nasty, a handfull of companies did survive to become multi billion businesses, one of them was PayPal which back in 2002 became a part of eBay.
Even more impressive is how a handfull of the (many) founders of PayPal went on start even more amazing companies within the technology space, to such an extent that the term PayPal Mafia was coined, with several parallels to the Fairchildren who seeded much of the semi-conductor revolution in Silicon Valley.
Three Recommended Links #3RL
The PayPal Mafia - A great article in Fortune from 2007 with one of the first mentions of The PayPal Mafia and how the group of PayPal founders was doing five years after the eBay acquisition.
PandoDaily Presents PandoMonthly - A series of interviews led by Sarah Lacy with three of the most visible founders with in the group; Reid Hoffman who went on to start LinkedIn, Elon Musk founder of Tesla Motors and SpaceX, Peter Thiel who is now a venture capitalist and was the first outside investor in Facebook.
PandoMaps: An interactive map of the PayPal Mafia | PandoDaily - An interesting interactive map of the relationships within and outside of the group.