I think Ken captured all the key points...
From an investor standpoint, the motivations are as follows:
- Get to the highest return possible (favors minimizing dilution incurred from options and other allocations)
- Which requires having a highly capable and motivated senior management team (favors generious options, with fair vesting)
- And a highly capable and motivated employee base (ditto)
- The capitalization structure of the company does not hinder or complicate an acquisition (i.e. reduce complexity of option pool; the more unvested options the better for the acquiror)
One other tool that is available to your board (and investors) is a management carve out. These carve-outs are typically not negotiated upfront. Rather they are used at the point of an acquisition to make management "whole" depending on the specific nature/terms of the acquisition. For example, if management and employees are not adequately vested and the majority of the proceeds of a sale are going to the investors, the board can ask the investors to agree to a carve-out. In effect, the board would be carving-out a portion of the proceeds into a cash pool that is distributed to management and employees based on a formula. The formula is yet another thing to figure out. Typically it reflects the option pool allocations.
Not sure if we're really answering your question... other than to say that everything is negotiable.
If your board/investors are not being generous, it is probably a reflection on one of two things:
1. You have not been aggressive in asking
2. The board doesn't think management/employees deserve more
If the latter, each manager should seriously think about whether he/she should keep going. That is a very personal decision.
I hope this helps.
Regards,
Firas Raouf
OpenView Venture Partners
bit.ly/aIWlOQ