FYI: Let’s say you own stock that may generate a big capital gain when you sell it. It could be shares in Apple or Amazon that you purchased a long time ago, founder’s stock in a startup that turned into a hot IPO company, or shares from employee stock option exercises or restricted stock vesting that have appreciated substantially. While most securities held over one year qualify for the favorable rate on long-term capital gains, the total tax can still be significant.
The complex federal tax code provides a few ways, depending on your income, personal financial goals, and even your health, to defer or pay no capital gains tax. If you follow the rules and consult tax experts when needed for the more sophisticated techniques, these tax-planning opportunities below are not tax dodges or loopholes that will get you in trouble with the IRS. Most are considered tax expenditures (i.e. what we tax geeks and the US Treasury Department refer to as tax-code provisions created to encourage certain activities or benefit certain categories of taxpayers).
Regards,
Ted
https://www.forbes.com/sites/brucebrumberg/2019/11/05/tax-strategies-6-ways-to-defer-or-pay-no-capital-gains-tax-on-your-stock-sales/#5284eae57ae1
