This is an unfortunate symptom of a huge problem with equity compensation: Valuing a stock option is difficult, even for finance pros. You need to understand the cap table, understand the company's current (and expected future) finances, the exact legalese in your offer, and how reality is likely to change as you remain employed. It's even more difficult when founders/investors don't tell you all the information. Your typical "Employee #1 Tech Bro" hasn't got a chance vs. the sharks. It's like an amateur sitting down at the poker table with 8 other seasoned pros.