Ordered from most compelling first. Some of these are about dollar savings. Some are about sleep at night. All ten are reasons every California seller with a six- to seven-figure gain should at least have on the table before signing the cash-sale closing docs.
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.
The single biggest reason. On a $2M California sale with a $300K basis, the lump-sum cash path hits ~35% combined federal + CA + NIIT + MHST = ~$595K in tax. The SIS spreads the same $1.7M gain across 5 to 40 years of carrier payments, so each year stays under the 15% federal LTCG ceiling, below the NIIT $250K-MFJ floor, below the California Mental Health Services Tax $1M threshold. Effective rate drops to ~22 to 27%. Saves ~$170K to $260K, permanently.
The payment is fixed at closing and is scheduled every month for the term (5, 10, 20, 30, or 40 years). The obligor isn’t the buyer (gone after closing) or the market (which can drop 37% in one year). It’s an assignment company, which funds your payments with a fixed annuity from a highly rated, heavily regulated life insurer. Your payments depend on that assignment company and insurer; they are not FDIC insured, and you should not count on state guaranty association coverage.
Sequence-of-returns risk is what destroys a retirement portfolio that’s drawing income through a bear market. A $1M portfolio drawing 5%/yr starting Jan 2000 nearly went to zero, not because the market returned poorly on average, but because the early bear-market years combined with withdrawals locked in permanent losses. SIS payments are fixed, schedule-locked, indifferent to market conditions. Sequence risk on the structured pool: zero.
No portfolio to rebalance. No advisor fees taking 1%/yr. No quarterly statements to second-guess. No 2008 panic. No 2022 panic. No decision to make about whether to sell into a downturn or hold. The payment shows up. You spend it. You do something you actually enjoy with your retirement instead of worrying about whether you should be in more bonds.
You take a cash carve-out at closing for whatever you need liquid: replacement-home down payment, debt payoff, kids’ college, emergency fund. Typical split: 20 to 40% cash at closing, 60 to 80% structured. The cash is fully liquid Day 1. Only the remainder is in the structured stream. Minimum structured amount is $500K. Above that, you choose the split.
The annuity contract has a designated beneficiary. At your death, remaining scheduled payments continue to your spouse, children, or trust (whoever you name). The beneficiary designation is revocable (you can change it any time, like a 401(k) or IRA beneficiary). Payments to heirs are still taxable as installment income at their bracket. Many sellers pair the SIS with a small term life or GUL policy to make the heir side fully tax-efficient.
The Revenue Act of 1926 created the installment method for sellers who weren’t receiving the full sale price at closing. It’s been continuously in the Internal Revenue Code ever since. The regulations say a buyer’s note is not a taxable payment even when a third party guarantees it (Treas. Reg. §15a.453-1(b)(3)(i)). No IRS ruling specifically approves the SIS assignment structure, so have your own CPA or tax attorney review it. Highly rated structured-settlement insurers publish white papers on it for estate-planning attorneys. The history of §453 →
In a traditional installment sale, the buyer pays you over time. If the buyer’s business fails, you stop getting paid. In an SIS, the buyer wires full cash to escrow at closing (gone, no ongoing obligation). The assignment company takes over the payment obligation and immediately buys a fixed annuity from a highly rated life insurer to fund it. Buyer-default risk: eliminated. Your payments now depend on the assignment company and the insurer behind its annuity.
The buyer signs one extra page (the SIS rider) at closing. It costs them nothing: the SIS doesn’t change their financing, their wire, their timing, or their post-closing obligation. You can offer the buyer a small price concession (typically 1 to 3% of sale price) in exchange for their signature on that one page. You still net more than a clean cash sale at the higher price because the SIS tax savings are larger than the concession. The buyer gets a discount; you get the SIS. Both sides win.
Cash sale + advisor = 1% AUM fee, fund expense ratios, trading costs, quarterly reviews, advisor turnover. Over 20 years on $2M, that’s $400K+ in fees compounding away from your retirement. SIS = no advisor fee, no AUM, no fund expenses, no trading. The carrier’s margin is already baked into the annuity yield you’re quoted. What you see is what you get.
The advanced calculator runs your actual numbers through 2026 federal + California brackets, NIIT, IRMAA, §453A (if >$5M), §483 imputed interest, and depreciation recapture. Twenty-minute call to walk through whether SIS is the right move for your situation.
Run your numbers → 213-414-2808
A plain-English guide for sellers on how a structured installment sale defers the tax when you sell a business, practice, or property. It covers the math, the alternatives, and how to tell if your deal fits.
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.
