Background: We are a <$50M, privately held C Corp with 70 shareholders. We have 5 layers of capital, with VC money senior preferred. A

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I've had the pleasure (not) of dealing with a very similar scenario, on several occasions. Unless you want to reference strictly the facts from your last equity raise and how that potentially impacts this particular shareholder's position; I would go with your option A. Speculating on any current market value now could come back to bite you should litigation ever occur.
That's helpful. Thanks, Paul.
Paul has given you excellent advice.
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