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Here's another way to think about it: if you had a pile of cash in the low five figures, would you re-invest it to speculate on that $100M acquisition? Or would you take it and pursue other opportunities?

If the tax implications are ok, can you borrow funds to cover the discounted stock purchase price, sell the stock, pay back the cost basis, keep the profits and don't look back?




It's a privately owned company. The stock is worthless. He can't buy it and then flip it on the open market because there is no market.


Could he could sell them to another shareholder?




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