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Re:Options vs. Cash by Pyxl101 on Wednesday June 07, 2017 @02:28PM (#14508710)
Why shouldn't employees also demand, and also be given, the right to buy more shares in subsequent funding rounds?

If I was going to work at a company for X% ownership, I'd sure expect to have the right to invest my own money to preserve my stake in a funding round and avoid dilution. Many employees might not exercise this privilege, since it would require putting (potentially a lot of) cash back into the company, but why aren't they given the choice? I also might expect to receive the same liquidation preference on any shares purchased in cash this way.

I'm not sure I could be comfortable working for a startup without pro rata rights and relatively full knowledge of the cap table and preferences. That's probably why I'm not working at a startup.

Re:Options vs. Cash by harryh on Wednesday June 07, 2017 @05:53PM (#14510158)
1) It would generally be a poor investment choice for an employee to invest their savings in a startup that they were actively working for. Startup employees are already over-invested in their company from a diversification perspective.

2) The majority of startup employees are unlikely to have the cash on hand to make that kind of investment.

Because of #1 and #2 this isn't something that most employees would care about so it's not part of any standard compensation package. It's possible that an employee could negotiate for such a provision though.

The fact that you would want a pro rata right to work at a startup does make you fairly unusual and I agree goes to explain why you have chosen other career options.