Thus the existence of companies like eShares that do away with this very problem for privately-held companies by issuing stock electronically and providing transparency (audit trails) to stockholders that paper certificates suck at.
eShares is an interesting solution but with so many parties involved (company, lawyers, several investor groups) how do you get one person to drive the solution? My experience is that something like that may be rocking the boat a little bit too hard.
Apologies for the late reply. Most of the time, the company is the driver, since they are the ones with the highest motivation to actually get a clean cap table. Law firms also drive – smart lawyers and paralegals will recognize they can use something like eShares to cut down on work and free up time for more valuable work.
Sure, there are a few companies that it takes a while for everyone to agree on the facts (example: prior CEO raised a bunch of angel capital on bridge notes, but some notes are missing, incomplete, or not executed...) but we have a lot more companies with near 100% acceptance rate of their outstanding cap.
Full disclosure: I work there.