eBoys - The First Inside Account of Venture Capitalists at Work

• Great teams check their ego at the door and are always interested in the greater good of the firm
  • “Benchmark partners had selected one another on the basis of perceived ability to subordinate individual ego to the larger interests of the collective.”
• Investors should be more than an active board member, be a confidant to the leadership team at all times
  • “The role that they preferred, or at least said they preferred, was that of “company builder,” which meant serving as an active board member and as informal consultant to the CEO in between board meetings.”
• In venture investing, the losses hurt you more than the wins make you happy.
  • ““The amazing thing is it hurts more on the downside than the good feelings on the upside.” “That’s my experience—three orders of magnitude,” Dunlevie quickly agreed. “Yeah,” Rachleff said, and then redid the ratio of intensity of pleasure versus pain. “One-X versus fifty-X.””
  • “The high payoffs for one or two never erased the pain of those that did not survive: “You feel so responsible for the disasters.””
• The first win should make you want to work harder to prove it wasn’t a fluke
  • “Bob Kagle could not take much pleasure in the event either, imagining, as he did, whispers that the eBay success was a fluke, akin to picking up a winning lottery ticket. He found himself working all the harder after eBay, to silence criticism that he had not actually heard but that he could imagine, beyond his hearing. One monkey don’t make no show, he’d say.”
• Reputation matters more than anything in VC and it takes a long time to build
  • ““After you get this reputation built up online,” Kagle explained, “you’ve got all these people who have dealt with you, you’ve got seventy-five people who’ve said good things about you. That’s a pretty fundamental thing.””
• Be curious, humble, and open-minded
  • ““I do, but the reason I do is because he’s a rare combination of highly intellectually curious and humble. I think he really is open to questioning his own thought process and what’s really working, what’s not working.” “It’s like being around an academic,” said Dunlevie. “He’s got so many ideas spouting forth, I really enjoy talking to him. My fear is that he’ll outthink it.””
• All companies go through growing pains, even the massively successful ones
  • “With more experience, eBay would have been further along, but adolescence cannot be skipped.”

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Reference: eBoys: The First Inside Account of Venture Capitalists at Work