Earlier quoted context omitted.
i don't think pooling is about loss _minimization_ so much as accepting that startups are often risky. the idea would be to give up a VERY small sliver of your upside in hopes of participating on other wins. I understand founders' desire to "maximize their upside potential", but if you cash out for 100mm, the incremental 5mm you give up has relatively small utility after the 95mm you cashed out. However, in the more…
Risk spreading reminds me of this Dogbert cartoon I came across back when I worked in finance: http://dilbert.com/strips/comic/2008-12-13/ Basically, risk spreading suffers from unintended consequences. There are however other alternatives to the portfolio approach that do make more sense. My favorite is the concept of a keiretsu ( http://en.wikipedia.org/wiki/Keiretsu ). This approach makes sense, especially when yo…
In this case, the founders already are invested in the dead cow, and so it can make sense to diversify to reduce risk. It's doesn't increase the value of their shares, it just makes the overall portfolio less risky.
The analogue to the MBS fiasco would be if the U.S. hit another depression, the whole YC class would be likely to flop, so the diversification wouldn't help, but in "normal" market conditions, the whole group would benefit from the few winners and get a payout in more scenarios.