Docs: https://www.clerky.com/yc-stock-plan-forms
1. On page 12 of the Stock Plan, there is a "Repurchase Option" that allows the startup to repurchase "at a purchase price for Shares equal to the original purchase price paid by the purchaser to the Company for such Shares".
This original grant price is likely to be far lower than any price paid by an acquirer.
2. On page 14 of the Stock Plan, there is a section on "Corporate Transactions". In the event of an asset sale, merger or acquisition, the company may can perform the "(E) the cancellation of any outstanding Options or an outstanding right to purchase Restricted Stock, in either case, for no consideration."
In other words, they can simply cancel your options.
Do employees regularly negotiate these terms out? They seem to give a startup incredible leverage in nullifying any stock option value you may have accrued during your tenure.
1. [Page 12 / Section 8(b) allows for the company to exercise a repurchase option on restricted stock at the original purchase price. You'll note that at the end of the paragraph it provides that "The repurchase option shall lapse at such rate as the Administrator may determine." The restricted stock purchase agreement that the employee actually signs in connection with their stock will set out the terms of the repurchase option (aka vesting), and it will allow the company to repurchase the unvested shares at the original purchase price. Switching this to a repurchase option at the then-current FMV isn't advisable because it results in de facto severance to the employee and would require the company to pay significant amounts of money to repurchase unvested shares if the FMV is high, even if the company doesn't have much liquid cash.
2. The full paragraph is below. The reason it's drafted this way is because company can't know at the time of stock plan adoption how options/restricted stock will be treated at the time of acquisition, so the stock plan has to allow for the full range of outcomes to preserve maximum flexibility. It's not atypical for unvested options/restricted stock to get no consideration in a deal, and those employees may just get a cash bonus (and in some cases, nothing).
Corporate Transactions. In the event of (i) a transfer of all or substantially all of the Company’s assets, (ii) a merger, consolidation or other capital reorganization or business combination transaction of the Company with or into another corporation, entity or person, or (iii) the consummation of a transaction, or series of related transactions, in which any “person” (as such term is used in Sections 13(d) and 14(d) of the Exchange Act) becomes the “beneficial owner” (as defined in Rule 13d-3 of the Exchange Act), directly or indirectly, of more than 50% of the Company’s then outstanding capital stock (a “Corporate Transaction”), each outstanding Award (vested or unvested) will be treated as the Administrator determines, which determination may be made without the consent of any Participant and need not treat all outstanding Awards (or portion thereof) in an identical manner. Such determination, without the consent of any Participant, may provide (without limitation) for ONE OR MORE OF THE FOLLOWING in the event of a Corporate Transaction: (A) the continuation of such outstanding Awards by the Company (if the Company is the surviving corporation); (B) the assumption of such outstanding Awards by the surviving corporation or its parent; (C) the substitution by the surviving corporation or its parent of new options or equity awards for such Awards; (D) the cancellation of such Awards in exchange for a payment to the Participants equal to the excess of (1) the Fair Market Value of the Shares subject to such Awards as of the closing date of such Corporate Transaction over (2) the exercise price or purchase price paid or to be paid for the Shares subject to the Awards; or (E) the cancellation of any outstanding Options or an outstanding right to purchase Restricted Stock, in either case, for no consideration.