> I doubt investors, who do this everyday and win some and lose some, worry all the time about why they passed on Google.
A very famous investor once said to me "you either invested in Google or you lost money."
Google is up 4000% since its 2004 IPO and 1000% from local bottom during the housing bubble crash. Didn't even need to be a VC to get access to VC level gains buying GOOG.
That's a great point. Anyone who shits on a VC for not investing in Google ought to be asked how much Google stock they bought in 2004.
4000% gains is better than most VC get on even the best exits and that opportunity was open to EVERYONE.
You could get a good estimate of this just checking Crunchbase. Assuming the company is doing well, none of the weird stuff like ratcheting kicks in. So just look at how much money went in and what valuation, apply dilutions for later rounds, and calculate what percentage you own by the time you get to an IPO.
This method still isn't perfect (employee option pools being adjusted will not show up, as well as other possibilities), but it'll definitely give you a rough estimate.