Canada Business Law
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Canadian regulations do not allow lawyers here to give specific legal advice without being retained directly so we are limited to general legal advice.
Does the existing shareholder's agreement allow for new shareholders to be added?
Is this person supposed to be a contractor or an employee with stock options or an investor? I sense a bit of all.
Will he be given shares immediately or options?
Without getting into all details, what essentially do you want to accomplish? Thanks,
Canadian lawyers are not allowed to take phone calls or give specific advice that you may rely upon to your peril without you becoming a direct client. Unlike USA lawyers (I guess) we are not allowed to provide additional services for a fee. I can only give general advice whereby you decide whether you pay something or not.
My instant concern is that you cannot do what you propose under the laws of most provinces. An option is a different thing than a share. A share is property while an option is an opportunity. Both can have buy back provisions however.
Such important decisions cannot be decided in a general legal forum and I am not allowed to become your personal lawyer. You need to hire your own lawyer who can sit down with you and fully understand.
I will opt out of this question and you can get a full refund of your deposit.