Step-Up of Cost Basis
Whenever a taxpayer dies, the cost basis of investment assets gets “stepped up” to the current market value. A wealthy investor could literally have millions — or billions — in unrealized capital gains that disappear at death, giving his or her heirs a clean tax slate. (Of course, estates larger than $5,340,000 in 2014 will be subject to the estate tax, but that is another topic for another article.)
Ordinary Americans inherit much smaller nest eggs, of course, but the same principles can be put to work with a portfolio of any size. If you are doing estate planning and have highly appreciated stock that you bought years or decades ago, consider holding on to it for the remainder of your life with the understanding that your kids or grandkids can sell it and reinvest the proceeds in a diversified portfolio.
I should give one important caveat here: Avoiding taxes should not be your primary investment consideration. If a single stock or small number of stocks makes up a disproportionately high percentage of your net worth, you might be taking too much risk. Avoiding a 15% to 20% long-term capital gains tax is great, but not if it comes at the risk of losing more than that in capital losses if the stock falls in value.
Every taxpayer will need to weigh the cost and benefit on a case-by-case basis.