Peter Thiel reportedly invested $500,000 in Facebook at a $4.8 million valuation. An alternative version of the story has him lending $700,000 to Mark Zuckerberg and eventually converting it into a 7.5% position in Facebook. Regardless of which version is correct, at the time of the S-1 filing he owned a 2.5% position. Not a bad return.
I have yet to find a clean valuation time line. This one is not bad:
Another from November 2010:
May 2005: Facebook raises $12.7 million in venture capital from Accel Partners, at a rumored valuation of $100 million.
April 2006: Facebook raises $27.5 million from Greylock Partners and Meritech Capital, for a reported $525 million pre-money valuation.
October 2007: Microsoft invests $240 million for a 1.6% stake in Facebook, valuing the company at $15 billion.
May 2009: Digital Sky Technologies invests $200 million for a 1.96% stake, bringing Facebook's value to $10 billion, a drop of more than $5 billion from Microsoft's investment.
January 2010: Offers to buy Facebook's private company stock on SecondMarket place Facebook's valuation at $14 billion.
June 2010: A report by Elevation Partners pegged Facebook's value at $23 billion.
July 2010: A report by Next Up Research pegged Facebook's value at $12 billion.
August 2010: Shareholder trading values Facebook at more than $33 billion.
November 15, 2010: Facebook's worth pegged at $41 billion.
November 19, 2010: Facebook shares sold at a $34 billion valuation.
November 22, 2010: Investors sell portion of stake in Facebook at a price valuing Facebook at $35 billion.
November 30, 2010: Facebook reaches value of $50 billion based on private market transactions.
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