The worst time to join a startup is right after it gets initial VC financing
One things I’ve noticed over the years is that equity grants given to new employees soon after Series A financings are generally a bad deal for those employees on a risk/reward basis. (By a Series A financing I’m referring the first round of funding by VCs, where the amount raised is roughly $2M or more).
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Founder vesting
The most important term in a startup term sheet that no one seems to think carefully about is founder vesting. There are two key points about vesting:
1) All startup employees – including founders! – should vest over 4 years from their start date (with a one year “cliff”). When I used to work in VC I can’t tell you how many companies I saw where some random former founder who was long gone from the company and was only there for some short period of time owned some big chunk of the company. Not only is this just plain unfair, it also means there is a lot less room for giving equity to employees and for raising new capital. Even if you are founding a company with your best friend – actually, especially if you are founding a company with your best friend – everyone should have vesting. If you have a lawyer who tells you otherwise, get a new lawyer.