The most frequently asked questions we run across regarding the option pool can be grouped into two categories:
The Option Pool is used primarily for two, highly intertwined, purposes. The first is to have a way to pay people with a currency other than cash when a venture is bootstrapping. The second, and related use, is to incent people (employees, consultants, service firms, etc...) to help make a venture succeed, and in turn make their options worth something. The earliest hires in a company are usually the largest recipients of the option pool -- The basic thought process being that the earlier someone joins, the more risk they are taking and the less posh their life will be for the near future.
Beyond the first employees, there are quite a few different schools of thought on who should get stock options and who should not, the best policy is to understand the implications of issuing different parties options and make sure that you're promoting the desired incentive alignment. For example, would it be worth giving your attorney options in return for a lower hourly rate? Answer: It depends. If it's a lawyer who is material to the future success of your venture on an ongoing basis then maybe. If it's a lawyer being used for a specific, time-sensitive transaction then probably not. There are lots of ways to provide incentives for getting things done and stock options are but one...use them wisely.
This is often a point of major contention in early stage (and even later stage) companies. Some equity ownership statistics can be found here from ventures in the life science and technology industries. Typically, the earliest employees to join a venture receive stock options corresponding to their position and expected role -- all of which vest over time, usually 4-5 years. For some ballpark ideas, option grants for early hires range from 5-8% for a CEO who is hired to run a venture to a fraction of a percent for a later or more junior hire. Early engineering hires, a group we frequently get asked about, vary a lot from fractional percents to low whole number percents. Like most things, it really depends on their value to the ventures success.
If you're planning on raising venture capital, then yes; the VC community will require it. If you're in the technology world, the smartest potential hires will expect this to be part of their compensation package. If, on the other hand, you have all the cash you need and you can attract the right talent to help you build your venture -- or in the very rare case that you don't need any additional help -- then maybe not.
One other thought worth considering is what is your desired outcome for your employees if you sell your company in the future? If you'd like to motivate them towards building as much value as possible and helping you achieve this outcome, then stock options can be a good tool.
Most venture firms will request that you make this 20% of the post-money valuation for very early financing. However, this, like everything else is subject to negotiation and it's worth addressing explicitly (see next question for why this is the case). A good idea is to really discuss what it is going to take to get you to the next valuation event and issue enough options to get you to that point (with some buffer). If you're only raising enough money for one year of operations and think that you'll only issue 10% of the company in terms of options in that time, then why issue more than that? You can always issue more options later at a higher valuation.
Maybe this should lead this section because it's a very commonly misunderstood piece of a financing.
In this tool -- as of the writing of this, we have modeled the worst deal for the founders to illustrate what stance your investors will likely begin the negotiations with. In the tool, ALL of the dilution from the option pool allocation comes from the founders stock -- meaning none of it comes from the investors. BUT - This, like most everything else is a negotiable term in a financing and it should be treated as such because its impact can be significant.
In an attempt to try and provide some insight on this issue, here is the case from each side -- investor and founder.
INVESTOR: Here are two reasons that will hopefully help put this conversation in perspective from the investor side of things.
FOUNDER: From the founders perspective there is really only one reason that it makes sense for the investors to share in the dilution that accrues due to the option pool -- but it's a good one. It is that you can't reasonably expect to build a company without investing in your team -- and not just the founding team. It takes engineers, developers, scientist, sales people, etc to build a company and these are not necessarily founding team members. But they are necessary ingredients for building a company and the investors should respect and take part in that. Another way to think about it is that immediatiately post-financing, the investors and the existing team are partners and they will move forward together on many fronts -- one of which is building the rest of the team...so wouldn't it make sense for them to share in allocating the option pool?
The impact of this can be quite significant if a company is successful -- This is why it is worth your time to really understand this as a negotiable deal term and not just a check box in a term sheet.
Also, understanding what happens unallocated options is important so don't be afraid to discuss this with your investors.