Peter Rip has a funny (and painfully familiar) comment about the near-inevitable “Oh shit” moment that comes at the first board meeting of a newly-financed early-stage company:
One of the ‘truths’ of the VC business is the “Oh Shit” board meeting. Generally, this is the board meeting where you find out the underlying basis for your investment was flawed. John Jarve at Menlo Ventures holds the record. As I understand it, he fought resistance from his partners to even get the UUnet investment done early in the Internet boom, AND at the first board meeting after the close the Company was already out of money! (I may have these facts wrong, but it still makes a good set-up.) He had to come back to the well after the Oh Shit Board meeting. UUnet ended up being a monster hit for John and for Menlo.