And now that Google 's purchase of YouTube for $ 1.65 billion has amplified talk of a second dot-com boom , many high-tech entrepreneurs -- like Reid Hoffman , above , an early executive of PayPal who profited when eBay bought the company in 2002 but recently watched his former PayPal colleagues make out even better on the sale of YouTube -- are examining their lives as measured against upstarts who have made it bigger .