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I'm seeing reports that Khosla led a Series A round of $10 million at $0.22/share (http://www.cnbc.com/2015/11/09/square-ipo-will-net-big-win-f...). At a $40M valuation.

$40M/$0.22 = ~182 million shares at that point? So they've almost doubled the number of shares they started with if they're IPOing at 300 million shares. Does that sound like a reasonable bit of math?

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At a $40M valuation, Khosla got 25% of the company at that time. They have $10m/$.22 shares or ~45M shares of the 182M shares you mention. They're netting $945M (sale)-$10M(invested)=~$409M.

Between Series A and IPO they had roughly 40% of their stake wiped out through dilution. (45M/182M=25%-> 45M/300M=15%) The dilution happened because, during that time Square issued 118M shares to investors in trade for the investor money. The company valuation at each round was determined by: Investment/shares issuedTotal shares outstanding after transaction.

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