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When should you expand the option pool — at each round or only when hiring?

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Venture capital funds generally only involve themselves to ensure that after a priced round in which they are participating (or leading for that matter), there is a large enough option pool (aka stock plan, aka equity incentive plan, and many more) to grant equity to and incentivize hires on the roadmap, with a buffer as needed (as well as for any bonus grants for performance, etc.). 

Otherwise, in the normal course of business for the startup, venture capital funds do not have any say in any changes to the option pool, unless they have negotiated for and included specific requirements into the priced round's legal agreements.

With respect to startups, they generally try to reserve sufficient stock in the option pool to last for a while, as reserving additional stock for issuance from the option pool requires paperwork and corresponding securities filings, in many instances. 

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