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Sarah Lacy addresses that question in her new book, Once You're Lucky, Twice You're Good, as she untangles connections among Digg, Facebook, Twitter, YouTube, and others; and Marc Andreessen (Netscape), Jay Adelson (Equinix), and Max Levchin and Peter Thiel (PayPal).
"I wanted to find their core motivator," Lacy says: "What made them go through all the pain and heartache again when the late '90s were so brutalizing?" She uncovered their biggest lessons: Keep control of your company, and be wary of venture capitalists.
Entrepreneurs from New York City's Silicon Alley are also launching Web 2.0 second acts. Click through for our scorecard.
NEXT: A dot-com deathwatch's tips
Last updated May 07 2008: 11:53 AM ET
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