I own stock in a previous employer that has just been acquired. I expect to receive a one-time lump sum payment of about one month’s salary, which I expect will be taxed as capital gains.
Every year I also make contributions to 501(c)(3) nonprofits which are tax deductible. I also occasionally make personal investments in LLCs.
Are there any measures you would recommend for me to explore for directing my lump sum capital gains directly into another vehicle that will reduce my tax burden for the actions I was already going to take? E.g., by moving it directly to a 501(c)(3) rather than cashing it in as income first.
This could help my donations to and investments in causes I care about can go further because of reduced tax burden.