How much will your California sale actually cost you?
Five inputs. One answer. Find out in 30 seconds whether a Structured Installment Sale would keep more money in your pocket than just selling for cash.
What's SIS? Structured Installment Sale. Sell once, get paid in monthly checks for 5–40 years from an A-rated insurance carrier. IRS taxes each check as it arrives, not the whole sale up front. Smaller checks = lower tax bracket = more kept.
Your numbers
All five fields matter. Income is the big one, it tells us how badly the tax stack hits you.
Net proceeds at closing — after commissions, loan payoff & any cash you keep out.
Purchase price + improvements
If yes, applies §121 exclusion ($250K single / $500K MFJ)
This is the most important field. Your existing income determines whether the cash sale stacks your gain into the top 20% LTCG rate + 3.8% NIIT + the CA MHST cliff over $1M. Higher income = SIS saves more. Be honest, be a little high if anything.
5 yrs15203040 yrs
Advanced inputs (depreciation, prior 1031, city tax), only if relevant
Rental/commercial only. §1250 at 25% fed + CA marginal.
If you 1031'd in, the carried-over basis from the original property.
Need more knobs? The advanced calculator has all the dials: city/county tax, HYSA/MYGA blend, SIS yield slider, life expectancy, devil's-advocate scenarios, etc.
Your answer
Same sale. Same 4.4% yield. Different tax exit. Here’s where you land after 20 years.
Take the cash
—
Pay $— in tax up front. Reinvest what’s left at 4.4%.
Structure it (SIS)
—
Smaller tax bills spread over 20 years. Each payment also grows at 4.4%.
SIS keeps you ahead by
—
SIS pays you ~—/yr after tax for 20 years, smaller tax bracket each year, all of it compounding.
Where the win comes from
Pure tax savings
If neither side earned a dime of interest.
+—
smaller brackets, year after year
+ realistic 4.4% growth
When your money keeps working.
+—
tax savings + compounding
SIS wins both ways. Even with zero growth, you keep more on tax alone. Add realistic 4.4% and the gap widens by —, that's compounding on a larger pre-tax base, because SIS hasn't handed Uncle Sam his cut up front.
—
Why it wins — in plain English
Two people sell for the same price. One pays the tax now. One defers with SIS. Here's the whole game:
💵
Pay the tax now and you only grow 65¢ of every dollar. Defer it with SIS and the whole dollar keeps working for you. A dollar beats 65 cents — same rate, bigger pile.
⏱️
At this rate your $2,000,000 roughly doubles to $4,000,000 in about 18 years. The cash seller doubles on the same clock — but only the smaller after-tax pile.
📈
Your full dollar stays working (not 65¢), and the gain is taxed in small yearly slices at lower rates. On a typical high-tax California sale that's about $1.29 kept for every $1 the pay-now seller ends up with — your exact number is up top. That's the whole trick.
What the calculator is actually doing
Where does the money go each year? You get a check, pay that year's tax, and we assume you reinvest what's left at the same 4.4%. Nothing disappears — and the cash side reinvests the same way, so it's a fair fight.
Is the interest taxed? Yes — the interest/growth is taxed as ordinary income every year, on both the cash side and the SIS side.
Federal and California? Both — federal capital-gains + 3.8% NIIT + California income tax + the 1% surtax over $1M + 25% depreciation recapture. The whole stack.
4.4% yield on BOTH sides. Cash net reinvested at 4.4% (taxed yearly as ordinary income); SIS at 4.4% carrier credit. This isolates the deferral advantage against a taxable fixed-income alternative — the structure keeps your whole pre-tax balance compounding. Real carrier rates run roughly 4–5%, depend on the term length, and are quoted & locked-in by the insurer at placement.
No carve-out. Real deals carve out cash at closing (tax bill, debt payoff, emergency), 99% of placements do this. We’ll size it on the call.
No IRMAA. The 2-year Medicare premium surcharge that hits one-time income spikes isn’t modeled. SIS dodges most of it; cash sale often triggers it.
No city / county transfer tax. LA, SF, Berkeley, Oakland, Culver City have nasty MHST-style adders that SIS partially defers.
No AMT, no depreciation recapture acceleration, no prior 1031 wrinkles. If any apply, cash-side tax is uglier, SIS wins by more.
Want every dial? The advanced calculator has carrier-yield slider, HYSA/MYGA blend, devil’s-advocate comparison, life expectancy, etc.
Disclaimer:Illustrative projection only. Actual returns vary. Carrier credit rates change. Tax law changes. Annuity guarantees subject to claims-paying ability of issuing carrier. Not tax, legal, investment, or accounting advice. Consult your CPA before acting on any number on this page.
Is this real? Walk through your specific numbers with Hans.
30-minute call. No pitch. Bring your CPA. Either SIS fits your sale or it doesn't, you'll know in 10 minutes.
Get this analysis as an email, every input, every computed value, the year-by-year SIS breakdown, plus a live link your CPA can open to see this exact scenario.
Educational only · not a quote · not advice. Numbers are illustrative ballparks using 2026 federal + California brackets. Actual carrier rates are quoted only by carrier-appointed structured-settlement specialists at placement. Annuity guarantees subject to claims-paying ability of the issuing carrier. Consult your CPA before acting.
Show me the math, tax breakdown line by line
Cash sale, Year-1 tax
Federal LTCG—
NIIT (3.8%)—
California tax—
CA MHST (over $1M)—
§1250 depreciation recapture—
§121 exclusion applied—
Total tax—
Net cash kept—
SIS — 20-yr amortizing annuity @ 4%
Annual carrier payment—
Gain recognized per year—
Tax each year (LTCG + interest + CA)—
Net each year (after tax)—
Total tax over 20 yrs gain tax + tax on interest you earn—
Value at year 20 (net + 4.4% reinvest)—
Assumptions:Apples-to-apples 4.4%/yr yield on BOTH sides over the term. Cash net is reinvested at 4.4% taxed yearly as ordinary income (your marginal rate); SIS uses 4.4% carrier credit on the principal balance (amortizing annuity), with each year’s after-tax payment also reinvested at 4.4% taxed-as-earned. 2026 federal + California LTCG + NIIT + MHST brackets applied. No city tax, no IRMAA modeled, no carve-out (100% structured), real carrier rates run roughly 4–5%. Advanced calculator exposes every variable.
Next step · for sellers age 55+
This calc shows ONE term. The optimizer tries every term, and tells you which one wins.
If you have a pre-tax IRA/401k, the SIS unlocks a Roth conversion window in the years before RMDs kick in. The optimizer factors in your age, IRA balance, Social Security, and IRMAA cliffs, then ranks every SIS term 5-40 yrs and picks your sweet spot.
Save this analysis · Email it to yourself or your CPA
Save a beautiful PDF for your records, or have Hans send it to you (or directly to your CPA) from [email protected] with the full math breakdown and IRS citations.
PDF saves locally. Email comes from [email protected] with the full report inline.
Every factor a CPA cares about: §1202 QSBS · §1245 · §453A · §199A QBI · city transfer tax · §121 · prior 1031 carry. Color-coded live math breakdown, every formula visible.
Skip if: you want lifetime planning or bucket allocation.
Optimizes SIS term 5-40 yrs across your full retirement. Models RMDs (age 73/75), Roth conversion ladder, SS taxation (0/50/85%), IRMAA 2-yr lookback, bracket inflation. Year-by-year ledger with IRS citations on every formula.
Skip if: you don't have a pre-tax IRA/401k or you just want the year-1 number.
Honest order: If you're new here, start with Quick. If your CPA needs to verify the math, send them Tax-Detail. If you're planning how to actually deploy the proceeds, use Cash-Flow Planner. If you're age 55+ with a pre-tax IRA, the Lifetime Optimizer is the strongest tool. All four show the math.
What this calc handles: Federal LTCG (IRC §1(h)) · CA progressive (CA R&TC §17041) · NIIT 3.8% (IRC §1411) · §121 home exclusion · §1250 depreciation recapture · CA MHST. What needs a 20-min consult: QSBS founder stock (§1202) · §453A interest on big deals (>$5M) · SF/LA city transfer tax · Roth conversion ladder during your pre-RMD years · RMD/IRMAA interaction · IRD treatment at death · multi-state if you move out of CA · K-1 lumpy income · trust structures.
If any apply to you, that's the conversation. 213-340-2018
📘 Get the free Seller's Guide to §453 + a fit-check
A plain-English guide for sellers: how a structured installment sale defers the tax when you sell a business, practice, or property — the math, the alternatives, and how to know if your deal fits.
Drop your info — instant PDF download + within 1 business day Hans will email a preliminary read on which structure fits your deal. No retainer. Carrier compensates the broker — not you.
📞 Hans Goldstein · 213-290-4977 · CA Insurance License #4322192 · Independent §453 specialist · Goldstein & Co. LLC
