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If a family member works for a company that gives out preferentially priced shares can that family member sign over some of those shares to someone else?

I'd like to give my brother some cash in exchange for shares in the company he works for at the discounted rate.
 
If a family member works for a company that gives out preferentially priced shares can that family member sign over some of those shares to someone else?

I'd like to give my brother some cash in exchange for shares in the company he works for at the discounted rate.
That's a private contract. It could say anything. Typically, the employee has to hold for a period of time otherwise the discount gets reversed. Once they are pulled from the company controlled plan and placed in your personal account, you are free to do whatever you want with them.

Realistically, although it's likely in violation of the agreement, if family member wasn't maxing plan, you could give them X dollars for y shares. They buy them now and transfer to you after the lockup (probably 6-24 months). This will trigger a capital gains tax owed by the family member in the year you get the shares. For tax purposes, I suspect the shares are a gift to you.

I don't think I'd want to be a part of this. Really messy and you could enrage CRA and their employer.
 
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That's a private contract. It could day anything. Typically, the employee has to hold for a period of time otherwise the discount gets reversed. Once they are pulled from the company controlled plan and placed in your personal al account, you are free to do whatever you want with them.

Realistically, although it's likely in violation of the agreement, if family member wasn't maxing plan, ypu could give them X dollars for y shares. They buy them now and transfer to you after the lockup (probably 6-24 months). This will trigger a capital gains tax owed by the family member in the year you get the shares. For tax purposes, I suspect the shares are a gift to you.

I don't think I'd want to be a part of this. Really messy and you could enrage CRA and their employer.

Hmm. Just to make things a little more complex these would be shares from a British company listed in GBP. Currently running at over $3k CDN per share once converted.
 
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