Broken cap tables

Reading this post I realized I literally have a stack of stock certificates sitting in my desk. Mostly because I don't want to take the time to put them in the mail (then I'd have to dig in emails for addresses, make a run to the post office, etc.) I know I should, I just haven't.

Until my lawyers started asking me questions I didn't even know I was supposed to do anything with them -- I just filed them away with all the other paperwork I knew I'd probably need sometime but didn't know what it was for. Honestly in my mind that goes under one of the bullshit administrative things I wish I could pay someone to take care of. If someone created a Zenefits for cap table management/investor relations, I'd be the first customer.

EDIT: I'm not just talking about cap table management (glorified spreadsheets). I want something much more comprehensive.

Isn't that what this article is about? eShares? I'm not a founder so I'm not sure if that's what it is "exactly" what you are looking for.

In the early 2000's, I exercised some options and did receive the stock certificate. Of course, they were worthless anyway (company was "acquired" for well under the capital put in.)

I find the idea that "less than 5% of employee option grants are exercised" both very sad and unsurprising. From working in this industry I've gotten the overwhelming impression that employees don't know how equity works. That leads them to systematically overvalue it, and by doing so they accept lower wages than they would otherwise. And companies that might have the best of intentions don't help at all, because their staffers don't understand it either.

You can't discount that most companies fail though, you'd expect the majority of options to go unexercised.

Edited to expand a bit:

Shares are ugly and annoying and cap tables are broken but it so rarely matters. Things should obviously be better and cleaner and more organized but since so few companies return anything to anyone besides the preferred shareholders, I'm not sure the 'cost' of this disorganization is very high. Seems like another case similar to the uncovered call option description of 'technical debt'. By avoiding the time and effort of energy associated with cap table management, companies can focus on things that add value and count on lawyers to sort it out when the work will provide value -- fundraising / M&A. There's a point to be made about the lack of a signal here too, if all companies are bad, then no company looks worse for meeting that expectation.