I've read a few successful startup founders say they wish they had granted their family some stock in the startup when they were just getting started. This seems to make sense for tax reasons. (Does it?)
How would you go about putting this on paper? I'm thinking a YC SAFE with a nominal cap sufficient to achieve the desired grant would be a pretty simple way to do it. Any other simple methods that wouldn't require paying a lawyer?
Edit: on second thought, I'm thinking a YC SAFE may be counterproductive in this case, because it won't provide for LT capital gains treatment in the (unlikely) event of an acquisition prior to conversion ...
Also, in general, the more people you have on your cap table early on creates more hassle as the company grows. Especially when it comes time to fundraise. This could cause potentially bad situations that you probably wouldn't foresee happening. Focus on building something successful and then it will be trivial to figure out once you're there.