Did Google Guru make best investment ever?

We haven’t done the definitive research on this yet, but we’re thinking Ram Shriram, the early angel investor in Google, made one of the best, if not the best, investment in a company ever.

Shriram is keeping the exact amount he invested into Google a secret. However, the angel round in 1998 of slightly less than $1 million consisted of four main investors, of which Shriram was one. When you factor in that a few other individuals, family and friends may have invested some money, we’ll assume Shriram invested between $100,000 and $200,000 give or take.

Given that his return is near $1 billion (see math below), he’s made between 5,000 and 10,000 times his money back. That’s got to be a record, right? True, much of Shriram’s investment profits from Google are still on paper. But Google insiders, including Shriram will be allowed to sell some more of their shares tomorrow, after a three-month lock-up period expires.

Here’s the math. Shriram owned 2.2 percent of Google’s shares, and first sold a portion at the IPO, raking in $22.6 million. He still holds an additional 5,058,427 million shares, which at today’s price of $185 (at least at the time of this writing) translates into an additional $935.8 million. That’s a total of $958.4 million.

Of course, this total tally changes rapidly, as Google’s share price swings. A couple of weeks ago, we did the math when Google’s price closed at $191, and his total was at $991.6 million.

While Shriram’s bet may be a record in terms of multiple, the venture capitalists, Sequoia Capital and Kleiner Perkins Caufield & Byers were the biggest absolute winners on Google. They elected not to sell their shares at the IPO — thinking that the $85 prices per share was too low. Since then, the shares have more than doubled — a good bet. They’ll have about 4.5 million shares released for possible sale tomorrow. Each invested about $12.5 million in the 1999 venture capital round.

According to Google’s filings with the SEC, Sequoia Capital owns 23,893,800 shares in Google, now worth $4.42 billion on paper, and Kleiner Perkins has 21,043,711 shares, worth $3.89 billion on paper.

It’ll be interesting to see what the expiration of the latest lock-up period tomorrow does to the Google share price. Googe sold only about 7 percent of its stock, or 19.6 million shares, in its Aug. 19 IPO — leading to what some said was a shortage which helped push up the price. On Tuesday, with another 39 million shares come on to the market, any excess demand might disappear.

On Dec. 16, 120 days after the IPO, another 25 million more shares will be unlocked and eligible for sale. On Jan. 15, another 25 million shares are released. Finally, on Feb. 14, the remaining 177 million shares will be unlocked.

So far we’ve only mentioned the investors. The co-founders themselves, Larry Page and Sergey Brin, are the outright winners. They each own about 38 million shares. So far each has sold a little over $40 million in stock. Their overall holdings are worth about $14 billion.

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