The Chicago Entrepreneur

The Moneyist: ‘I partially support my partner of 12 years as his business is, sadly, failing’: I’m 33, and have $300,000 in company stock. Should I sell those shares to pay off my debt of $56,000?

‘I realize I will have to pay some fairly large taxes due to the gains on the stock, so I need to factor that into the sale as well.’

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