Once You’re Lucky, Twice You’re Good

Business reporter Sarah Lacy chronicles the entrepreneurs who took lessons from the dot-com bust of 2000 and went on to build a new generation of web companies, the wave known as Web 2.0, whose common thread was bringing people together online. Her examples range from Facebook and MySpace, which connect friends, to YouTube for posting video, Digg for voting on the day's news, Six Apart for blogging software and Slide for customizing online selves. Drawing on anecdotes about the founders, Lacy also portrays the wider scene around them: venture capitalists, bloggers stoking the hype, programmers coding all night, millionaires in their twenties and fans eager for the promises to come true. It came out in 2008.

Pittsburgh Technology Council chief executive Audrey Russo included it among the books she recommends to young people interested in her career path.