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"At what point is it prudent to pull my original investment money out and spread it into another venture?"

There isn't really a defined time. There can't be.

You need to decide based on your specific portfolio of investments, your time line, your goals, etc. Some of these change from time-to-time.

If you are referring to Cramer's "Pull out your investment and play with the house's money" there is nothing that is more ignorant on his show.

There is no house when you are investing. The money invested is identical to the money paid in dividend and the capital appreciation. It is all yours.

If you are retired and have no new cash coming in, you use cash from sales and dividends to buy new companies. If you are working, you can add new deposits to that list.

Does that help you?

All holdings and some statistics on my profile page
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