Lets say you're the CEO on the way to raising VC for your startup, is there anyway to structure these two scenarios:
1. You want to offer more equity to employees than normal. Instead of making the employee option pool bigger, you just give away some of your own equity. If those employees leave the company before vesting or do not exercise their options, can you as the CEO recoup the equity you personally gave away or does it all go back into the employee pool?
b. Early exercise for employees. Is it illegal for the company to loan out money to pay for a new employee to early exercise their options? Will the IRS remove the longterm capital gains benefits should those options at some point be involved in liquidity event?
1. You want to offer more equity to employees than normal. Instead of making the employee option pool bigger, you just give away some of your own equity. If those employees leave the company before vesting or do not exercise their options, can you as the CEO recoup the equity you personally gave away or does it all go back into the employee pool?
b. Early exercise for employees. Is it illegal for the company to loan out money to pay for a new employee to early exercise their options? Will the IRS remove the longterm capital gains benefits should those options at some point be involved in liquidity event?