40 year corporate finance career in Corporate Finance with Fortune 500 companies including UnitedHealth and ING. Focus on insurance lines including annuities, life and health. Now retired.
Excellent article. Your example gets at it, but specifically the “stackable” of other income sources is a key complexity to understand as most people will have other income than their cap gains. I screwed up my LT cap gain sale last year due to not calculating this entirely correct.
Comments
Agreed - exactly how I view it
Post: Who cares if Social Security benefits are cut?
Link to comment from December 30, 2025
You won’t necessarily recover more quickly
Post: Average vs. Humble Average
Link to comment from December 30, 2025
Saving on taxes legally is an American sport and way of life. The code is so complex, it’s a constant battle.
Post: Enough with IRMAA complaining
Link to comment from December 30, 2025
How could it possibly use a one year look back that isn’t understood until 4/15 or later?
Post: Enough with IRMAA complaining
Link to comment from December 30, 2025
Good Timing? Not exactly how I’d describe a likely massive fraud/theft. I’d imagine Adam was being gentle here.
Post: Money Moments
Link to comment from December 27, 2025
Start by not driving a Bentley. Haha
Post: Can we be completely safe?
Link to comment from December 20, 2025
There’s Costco insurance? Who underwrites? Thanks
Post: Home, Auto & Umbrella Insurance—“Longevity Benefit”?
Link to comment from December 7, 2025
What Social Security payout option do we have? I’d have rather invested my 15.5% (or thereabouts) of income myself as I can trust myself.
Post: The annuities are coming, the annuities are coming‼️
Link to comment from December 6, 2025
I keep 1-2 months in a money market fund and the next 12-18 months in ST bond funds.
Post: Where to Keep Cash
Link to comment from December 6, 2025
Excellent article. Your example gets at it, but specifically the “stackable” of other income sources is a key complexity to understand as most people will have other income than their cap gains. I screwed up my LT cap gain sale last year due to not calculating this entirely correct.
Post: Tax Gain Harvesting
Link to comment from November 8, 2025