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[JC99]

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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.

 

[GreyGhost]

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.

 

[JC99]

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.

 

[GreyGhost]

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.

Share price doesn't matter. Contract matters a lot. I have no idea about capital gains/gifts across borders.

 

[GreyGhost]

When can you trust past returns as an predictor of future results? Over the past 15 years, in my RRSP, I have been getting an annualized return of between 26 and 27% (some good years, some bad, this is the compounded average and includes the growth due to inflation). Over the last five years where I used a better tracker, XIRR of all of my investment accounts combined is in the same range. That's works out to investments tripling every 4-5 years. Obviously the safe approach is to wait until the size of the warchest is ~25x the perpetual earnings I want. That would have me working for more years when I could be enjoying life though. Also, I'm getting older and fatter. Ditching work would give me more time to ride bikes (power and motor). That should extend my healthy life.

I don't plan on taking my foot off the gas in the portfolio. If a year sucks in the markets, I am ok with taking a poverty year where I withdraw as little as possible. Sadly, many years left on mortgage so that is a significant cash burn that is unavoidable. If I don't screw it up, I can do whatever I want and set the kids up (if I want to and they prove worthy).

I guess the smart strategy would be semi-retirement but that isn't ideal as my corporate expenses would remain so a decent amount of work would be lost to covering expenses.

When I think I am in a good enough spot, I'll fork out for one of the fee for service advisors to see if they can flag major problems with my plan. $4000 to avoid a landmine is a great value.

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