Great situation you have found yourself in! Good for you!
What your friends are doing and putting you through is common.
When I have given out shares I calculate several things:
1. time they will be involved in the company.
2. the value they provide in the scalability of the business - not their current offerings (this helps give out additional after certain time frame)
3. Consider their current value, how easily replaceable is their skill set.Be honest with yourself because this can cost you.
4. Have they been heavily involved since the beginning?
5. Do you want them around?
6. Did they directly help win part of the contract?

The truth of the matter is that a lot of startups would have maybe considered them as advisors and granted them no more than 1% of the company. I did this as well with my board. Early partners in my case one had 30%, while another had 5%, several had no more than 1%, I had 50% and we left 10% available for investors.

However the reality of this is that they are now employees, you can however consider them partners and provide incentive to stick and keep working harder. Not stock all granted at once though.

So, to clarify- are you filed as a Corp? the laws (if you are in the U.S.) are different for partnerships between LLCs and Corps... LLCs lean more towards all owners/partners having equal claim but under contracts could have limited representation and salary draw.

If you have any further topics to discuss feel free to give me a call!

Humberto Valle
@officialUnthink
Get 5 Growth Hacking Tips & Trends
http://Newsletter.unthink.me