1.) How Charlie made his move from college to venture and then struck out on his own from USV?
2.) Charlie has previously said that ‘venture capital is humbling’. How does Charlie look to construct his portfolio with Brooklyn Bridge? How does he come to terms with the fact he will be wrong most of the time?
3.) What are Charlie’s views towards follow-on funding and allocating reserves of the fund? How important is this from a return multiple perspective? How much of a difference does it make for founders to raise a next round with 100% of seed investors committed?
4.) Charlie has previously suggested the importance of being helpful and hard working. Is that really enough to build a brand in today’s competitive VC environment? Is brand a form of defensible IP?
5.) How does Charlie react to Ben Lerer’s suggestion that Jet.com and Dollar Shave Club are the first dominoes of an incoming wave of e-commerce M&A?
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