Can a company cross a transaction between two shareholders without the use of an exchange or a broker dealer?
The answer is yes, if their captable is maintained digitally and that software provider is also a registered transfer agent. However since this capability is less than 2 years old, most still prefer to have the assistance of the broker dealer who helped them raise their capital or one they hope to work with in the future.
Why should I care about helping an investor who no longer wants to be a shareholder?
Apart from being grateful that the investor believed in you early on, it's likely you will want to raise capital in the future and it's not helpful to have recent transactions at low valuations because you failed to maintain a robust community of potential new investors.
We are a private company, what if we don't want our competitors or clients knowing how small we really are?
For some this may be a concern; but its been my experience that transparency into the good stuff, and the community of fans that brings, far outweighs any perceived value that may otherwise exist temporarily .
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