Evaluating fairness of an Investment/Shareholders' Agreement

When an investor invests in a startup, they present the company with an Investor/Shareholder Agreement, which outlines the rights and obligations of the shareholders within the company, including voting rights, share transfer procedures, dividend policies, and protections for minority shareholders. These agreements safeguard the investor's financial interests and govern their relationship with the company and other shareholders.

It is common for the initial investor to have more rights. Normally, early investors expect the following protections:

• Board representation (a seat on the board).
• Veto rights on major financial decisions (e.g., capital raises, mergers, or asset sales).
• Approval rights over key hires or changes in the business direction.
• Liquidation preferences to get paid first in case of a company exit.

But sometimes their demands can be excessive. To evaluate the fairness of such agreements, you can upload the proposed agreement to chatGPT and use the following prompt:

Does the contract reflect a balanced distribution of power? If not, what share percentage would correspond to the class B shareholder's power? Is this normal for an initial investor in the startup, considering that convincing the first investor is often the most difficult?

If the agreement grants a 15% share in the company but provides 50% control, which is more aligned with a controlling or near-majority stake, we can say the agreement is not fair. Common unfair clauses in such agreements are:

• Even though the class A shareholder (founder) appoints the board member, any change in the board representative requires class B shareholder (investor) approval.
• Class A shareholder cannot transfer shares without class B consent for 3 years, while class B share holder is free to transfer to affiliates or related parties without restriction.
• Important strategic decisions need approval from the Steering Committee, where both A and B share holders have one representative each. Any deadlock in this two-person committee could give the B shareholder veto power over important business decisions​.

You can use the following questions to persuade the investor to be more flexible:

• Do we agree that the founder/CEO of an ambitious startup with rapid growth goals needs to be able to act quickly, requiring minimal approval/bureaucracy?
• To fund rapid growth, we most probably will need other investors. Can we foresee that this agreement might irritate potential investors, lower the company's value, and lead them to request the same privileges? 
• If the same privileges are granted to other investors, would reaching an agreement on any matter outside of routine business—especially considering the potential for irrational behavior (such as ego conflicts, etc.)—become practically impossible?

The goal is to help the investor see the mutual benefits of more flexible terms. You want to highlight that while protecting their investment is important, collaboration, agility, and attracting future investment will ultimately lead to better outcomes for both parties.