A large, low-basis position (founder shares, RSUs, an inherited holding, decades of a single stock) is a tax trap. A 1031 exchange can't help (that's for real estate). These are the strategies that actually work.
You're holding too much of one stock. Maybe it's founder or employer equity, RSUs that vested, an inherited position, or a single name you've owned for 30 years. Selling means a giant capital gain; holding means dangerous concentration risk. And unlike real estate, a 1031 exchange does nothing for stock. Your real options:
Send me the sale price and rough basis. Within one business day I'll email you the actual number and the Seller's Guide to §453. If it doesn't fit your deal, I'll tell you that plainly.
No retainer · no obligation. Hans Goldstein, a licensed insurance agent (CA Insurance License #4273294), will contact you and may discuss insurance products, including annuities.
A low-basis position means most of the value is unrealized gain. Sell it all at once and you stack the 20% federal rate, the 3.8% NIIT, and (in California) up to 13.3% state. That's roughly a third gone, and you may spike into the top bracket and trigger IRMAA. The goal is to diversify or exit without detonating all of that in one year.
Exchange funds have high minimums and a 7-year lockup; CRTs are irrevocable and charitable. For someone who simply wants to sell the position and stop sending a third of it to the government in one year, a §453 structured installment sale spreads the gain across years, with payments from an assignment company funded by a fixed annuity from a highly rated life insurer. No minimums to qualify, no replacement asset to find.
No. A 1031 exchange only applies to like-kind real property. For appreciated stock, you need other strategies such as a structured installment sale, an exchange fund, or a charitable remainder trust.
Spread the sale over years with a §453 structured installment sale, contribute to an exchange fund for tax-deferred diversification, or use a charitable remainder trust. Each defers or reduces the one-year tax hit in a different way.
An exchange fund lets you contribute appreciated stock into a diversified pool without a taxable sale under §721. It typically requires around a $5 million minimum / qualified-purchaser status and a roughly 7-year holding period.
You sell the position but receive the proceeds over a schedule of future years, paying tax on the gain only as you receive it. This keeps more of the gain in lower brackets and can reduce the 3.8% NIIT, and unlike an exchange fund, there's no minimum to qualify.
It depends on your goal: a structured installment sale if you want to fully exit and spread the tax, an exchange fund if you want to stay invested but diversified and meet the minimums, or a charitable remainder trust if you have a charitable goal and want lifetime income.
Before you sign anything, run your numbers with someone who structures the deal to be tax-smart and audit-ready from day one.
Call 213-414-2808 Run the Numbers →
Send me the sale price and roughly what you paid. Within one business day I’ll come back with the number you’re actually looking at on a stock position sale, and whether a structured installment sale can push it down. If it can’t, I’ll tell you that just as plainly.
Leave your details and the PDF downloads right away. Within one business day Hans will email a preliminary read on which structure fits your deal. No retainer. On a funded structure, the insurer pays a one-time commission of about 4% of the amount structured to the brokerage firm that places it (Hans’s share is about 2.4%; no trail). It is built into the annuity pricing, not a separate fee.
📞 Hans Goldstein · 213-414-2808 · CA Insurance License #4273294 · Independent §453 specialist · Goldstein & Co. LLC
Hans Goldstein, a licensed insurance agent (CA Insurance License #4273294), will contact you and may discuss insurance products, including annuities.
Hans Goldstein is an Enrolled Agent, admitted to practice before the Internal Revenue Service. Not affiliated with or endorsed by the IRS. General education, not tax or legal advice for your situation.
