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>> Founders cashing out is a big red flag.

No, it's not. Palihapitiya agreed that there should be a secondary component to the financing.

When a company is "shooting for the moon" and has a chance at a >$1B exit, investors want the entrepreneurs to cash out a portion of their stock, because it gives them the financially flexibility to swing for the fences. It aligns the founders and management team with the late-stage investors.

Fred Wilson does a great job explaining why founders and early investors cashing out in late-stage financings is a Good Thing for everyone.

http://www.avc.com/a_vc/2010/01/the-tug-of-war-between-ma-an...

http://www.avc.com/a_vc/2010/08/angel-liquidity.html



> Palihapitiya agreed that there should be a secondary component to the financing.

Agreed. I think what OP meant was "founders cashing out [using this method rather than a secondary sale]" is a big red flag.




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