I had a call with a guy who sold his business for ~$17M in CA two months ago.
No tax planning.
Now he’s staring at a massive tax bill and asking what we can do.
At this point in the year, we’re limited.
We can do some bunching of charitable donations, tax‑loss harvesting, and maybe real estate depreciation if he has REPS.
These can help a little bit, but there is still going to be a meaningful tax bill.
Real tax planning happens before you sell the business, not after.
If you start 12–24 months before an exit, you can look at:
- Entity structure and deal structure
- Timing of the sale (December vs January matters)
- Pairing gains with long/short loss harvesting
- Charitable structures
- Installment sales
- Real estate / REPS / depreciation
Once the sale is done and the clock is ticking on the tax year, a lot of the biggest levers are gone.
But we can still build a tax‑aware portfolio for the proceeds going forward.
The damage from this exit is largely done.
The next one (or the next decade of investing) doesn’t have to be that way.
If you’re thinking about selling a business in the next 1–3 years and don’t have a real tax plan yet, that’s your cue.