Broken cap tables

You might grow to wish you didn't have it. It's a pain to hold a physical stock certificate with actual value.

Put that sucker in a safe deposit box, if you haven't already. If you lose it, you'll be in for a bureaucratic nightmare of indemnity bonds (which are expensive!) and notaries to get your money. And on the happy day you get to exchange your piece of paper for cash, you get to live through the unique experience of trusting a huge sum of money to the postal service.

It's a like backing up your computer on a local hard drive because you don't trust cloud providers: the chance that a law firm will lose your certificate is a lot lower than the chance that you will.

The 90 day exercise window for stock options really catches some non-finance employees off guard. They don't realize the high amount of tax and investment that has to be made for illiquid shares (which are still pretty risky for most start ups). That being said, there are a few options that I feel more people should know about including the Employee Stock Option Fund (http://esofund.com/). If you fall within the 90 day period, I would highly suggest sending them an email. They are able to produce the money very quickly and will do their best to help you.

Very true. I've seen software and consulting firms with the worst systems and processes because anyone good at them was working externally not internally.

Could not agree more: "the practice of equity administration is systemically biased against employees" (and to protect companies and investors). Equity admin isn't just a mess for startups but can be a mess for mature companies, too. If you have a chance to interview a manager before accepting an offer, I highly recommend asking them how well Finance has their shit together. You don't want to, say, get in a fight with the General Counsel over stock...

I had major stock admin issues at a fairly mature (then 6-year-old) company that is now public. Soon after I started, my boss promised me a follow-on stock award for good performance but failed to do any of the paperwork. I only discovered this issue when I later requested HR to audit my paperwork, and I ended up having to fight our General Council (who was also on the board) for an ENTIRE QUARTER over this mess. The GC not only badgered me but completely mislead me and had the board change my grant without my signature on the final agreement in order save his face (and likely the company from running into trouble with pre-IPO auditors). It took a ton of painful arguments with my boss (and revelations that he had other 'broken' stock promises) to finally get that stock re-awarded. To save HIS face he ended up giving a bunch of my colleagues pre-IPO stock bonuses too (though some had that 'fuck-off' back-weighted 10/20/30/40 vesting). The whole process unfortunately obliterated the trust in the relationship and made /vesting/ the (mostly) restored stock very, very painful.

If the law, regulations, and administration were a lot more straightforward, I doubt any of this would have ever happened. (Well, if my boss and the General Council would have owned up to their mistakes, that would have helped, too :) . Something like eShares might have also enabled my company to let non-management employees do 83(b)s leading up to what turned out to be a highly successful IPO.

eShares is nice, but some sort of basic, open-source and free baby gate would be a huge help, too. When managers have so much control over employee compensation, it's really easy for them to fuck things up (intentionally or not).

Sam Altman advocates for a longer exercise window [0] as part of his piece on employee equity. More early-stage companies are adopting it, but it's not without complications. For example, 90 days after termination ISO shares convert to NSO shares, which are a different beast for taxation purposes -- employers/employees rarely understand ISO shares, let alone ISO+NSO.

[0] http://blog.samaltman.com/employee-equity

[1] I work @eShares.