A listener emailed me who is lucky enough to get a generous gift every year from their grandparents of $14,000 in stocks. The stock is all from a single company that her grandfather worked for decades ago. Because he bought it early in the companies history it's basis is $0, meaning that they are on the hook for capital gains tax for anything they sell it for. The stock does relatively well and pays out good dividends. However, they don't love the risk of owning so much in one stock. He wanted to know what I thought they should do. Is the risk of keeping the stock outweighed by the tax penalty of selling the stock? Is there a way to convert this stock to a safer index fund without having to pay the capital gains tax? We are not all so fortunate to have relatives that gift us so much in stocks but it is still a question that I get every now and then so I wanted to address what to do with individual stocks in your taxable account, the pros and cons of selling them vs keeping them as a legacy holding in your portfolio.
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