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How much equity do you give early employees when the company is bootstrapped?

How much equity should be given to early employees when the company is bootstrapped?
Leonard KimLeonard Kim, Corporate Strategist. Marketer... (more)
333 upvotes by Marc Bodnick (Co-Founder, Elevation Partners), Shannon Sofield, Ryan Cantin, (more)

How much equity do you give early employees when the company is bootstrapped?

This is how I organized my last company, which was what this business plan was made off of Leonard Kim's answer to How does one create a business plan?. (Keep in mind, this is an equity structure for a clothing line, and not a tech start up. Technical cofounders may be much more important in another industry than the one I was in.)

I start all my companies with three main founders.

First, I issue 50 Million Shares to the company within the Articles of Incorporation.

Then I distribute 10 million of those shares as follows:

1,000,000 - Holdings
2,000,000 - Operations / Marketing (Me.)
2,000,000 - Finance
2,000,000 - Product
300,000 - Photography
300,000 - Creative
300,000 - Business Development
100,000 - Web
100,000 - Product consulting
100,000 - Product design
100,000 - Graphic Design
100,000 - Manufacturing
100,000 - Board Member
100,000 - Other Necessary Position
300,000 - Attorney
200,000 - Important Person you find down the line.
100,000 - Important Person you find down the line.
100,000 - Important Person you find down the line.
50,000 - Important Person you find down the line.
50,000 - Important Person you find down the line.

Down the line, I reserve the 10% of outstanding shares of the 10 million for employees.
25,000 - Employee / Board Member / Advisor / Mentor
25,000 - Employee / Board Member / Advisor / Mentor
25,000 - Employee / Board Member / Advisor / Mentor
25,000 - Employee / Board Member / Advisor / Mentor
25,000 - Employee / Board Member / Advisor / Mentor
25,000 - Employee / Board Member / Advisor / Mentor
25,000 - Employee / Board Member / Advisor / Mentor
25,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor
10,000 - Employee / Board Member / Advisor / Mentor

I make sure that all the shares vest. I don't allow shares to vest until after the first year for everyone except for the holdings company. In a tech based industry, I would recommend a five year vesting schedule. In a brick and mortar business, I would recommend ten years, since they take longer to acquire. The reason that shares should vest is because not everyone will stick around. Sometimes, situations will arise where it is necessary to offer up equity for a replacement if someone decides to not stick around or if someone gets fired.

Some people may be wondering why all 50 million of the shares are not issued and only 10 million are used in the distribution method mentioned above.

If I need to raise money and issue out 50% of my company to an investor, then I would have to issue 50% of the outstanding shares. This a situation where, if all the positions listed above are fulfilled, an additional 5 million shares would be issued, bringing the total share count to 15 million.

If times are extremely rough and I need to raise more money and issue out another 50% of my company, I would have to issue out another 7.5 million shares, bringing the total share count to 23.5 million shares.

This share structure allows me to go through four rounds of financing without restructuring the company in case the absolute worst case situation arises, when cash infusions are absolutely necessary for survival, and equity is something that would need to be issued out due to desperation.

However, a savvy founder would do their absolute best to ensure that a percentage far less than 50% is issued out to the investor in each stage of fundraising.
The worst case scenario in this situation is that you, along with your two cofounders, would each own 4% of the company if you had to fully liquidate your shares. The best case scenario, with going through only one stage of fundraising at 30%, would leave each of you with 15% of the company.

Reference this infographic I found from Marco D'Alia to see why:
http://qph.is.quoracdn.net/main-qimg-8d2ad5699507224781d4544dd2dbeadc?convert_to_webp=true