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I would sell my business when all the debt or original investment had been paid. It would be ideal to sell when the business had earned enough to finance my next business goals or my expenses through retirement.
If my business did not reach my retirement goals, then I would invest in a business that could. Retirement goals would include paying off all my personal debts and having my cost of living paid for the remainder of my life.
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What would be the dream business for you?