The Waterfall Strategy

New · A companion to The Waterfall Strategy

Same losses. Same gain. A different calendar.

Selling a building or a business, and holding capital losses on your tax return? Sell for cash and the gain lands in one year. Sell on the installment method and it lands on a schedule you know before closing, so a loss that shows up in year three has gain waiting for it. The Loss Bank is the tax rulebook for matching the two, year by year, with worksheets for you and your CPA.

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Cover of The Loss Bank: Matching Capital Losses to an Installment Sale, Year by Year, by Hans Goldstein
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How it works

A capital loss is a coupon. The installment schedule tells you when the store is open.

Against capital gain, a capital loss counts dollar for dollar. Against wages, pensions or interest, it's worth $3,000 a year. So the question isn't only how many losses you have. It's whether there's gain on the return in the year they land.

One

The bank

The carryforward on last year's Schedule D, plus any capital losses that land on your return in later years. The book covers which losses count, which never will, and the rules that can wipe one out.

Two

The calendar

On the installment method you're taxed as you're paid (IRC §453). The schedule in the contract tells you, before closing, how much gain lands on each year's return.

Three

The scoop

A scoop is the loss your return uses against one year's installment gain. One scoop a year, sized to that year's payment. Your CPA sizes each scoop from the losses on your return.

"One scoop a year, sized to that year's payment."

Shape the schedule to the scoops

Illustrative composite (the Chens, Chapter 9): a $1,000,000 gain; a $100,000 carryforward plus $40,000 of capital loss on the return each year for ten years, as given by their CPA. Same gain, same losses, two calendars.

5 years, level$72,743

The gain runs out in year 5. Years 6 to 10: $40,000 a year lands with nothing to meet but the $3,000 allowance. $185,000 still unused.

10 years, level$110,086

Every year's scoop has a payment to meet. $0 unused.

Installment gain that yearScoop: loss used against itLoss with no gain to meet

Dollar figures: what the losses were worth in federal tax over ten years, with the 3.8% tax, 2026 tables held constant. Interest, time value and reinvestment left out. Illustrative only; a longer schedule also means more note interest (ordinary income) and later money. The book covers both.

This is tax timing only. Whether losses land on your return at all, and how many, is a question for your investment adviser. The book never tells you to buy or sell anything. It shows what your return does with the losses once they're there.

Who it's for

Two ledgers, one return.

Written for you if

  • You're selling, or about to sell, real estate or a business with a large gain.
  • You have a capital loss carryforward on last year's Schedule D.
  • You hold a taxable brokerage account where capital losses may land on your return.
  • You're weighing a cash sale against seller financing or a structured installment sale.
  • You want to walk into your CPA's office with the right questions and a worksheet.

Not for you if

  • You want someone to tell you what to buy or sell. That's your investment adviser.
  • All of your investments sit in IRAs or 401(k)s. Losses there never reach Schedule D.
  • Your only sale is a home fully covered by the §121 exclusion.
  • You want a promise of zero tax. Losses reduce the gain taxed in a given year; that's the claim.
Your state

Does it help in your state?

California residents: more than you'd think.

California taxes capital gain as ordinary income, up to 13.3%, and follows the federal loss rules. With no lower layer, every loss dollar that meets gain saves your full California rate.

Selling California property from another state: federal only.

The gain stays California-source. Your portfolio losses are sourced to your home state, so they don't reduce it (FTB Schedule D (540NR) instructions). They still cut your federal tax.

Pick a state

Tap a state on the map, or choose one from the list, to see how capital losses meet installment gain there, for residents and for nonresidents selling property in that state.

Ratings are plain-English summaries of state rules checked against state tax agency instructions and statutes on the date shown. Rules change; your CPA confirms yours.

The book has a "Your state" section in Chapter 8 with a ten-state table, and the full table for all 50 states and DC in an appendix. Educational summary only; not tax advice for your facts.

What's inside

Thirteen short chapters, six worksheets, and every citation your CPA will ask for.

Part I: The idea

  1. 1Two Ledgers, One ReturnWhy a capital loss is a coupon, and why the calendar is the lever.
  2. 2What's in the BankFinding your carryforward; what counts, what doesn't; short-term and long-term passbooks.

Part II: The rules

  1. 3The Netting OrderWhich layer of your gain a loss hits first: up to 10 cents more per dollar.
  2. 4Every Kind of Loss That Can Meet Your GainCapital losses, passive losses and the deductions around them: a map, not a menu.
  3. 5Rules That Can Disqualify a LossThe wash sale rule, where it hides, and losses to family.
  4. 6What Losses Can't Touch§1245 recapture, note interest, §1231 netting.
  5. 7The 3.8% Tax and Your BracketsHow a loss lowers the top of the stack.
  6. 8State Tax: Your State, California and the Nonresident TrapA ten-state table and the resident vs. nonresident split.

Part III: The calendar

  1. 9The Schedule Is the LeverYear by year, electing out, and why the bank closes at death.
  2. 10Why a Bank Runs LowWhat published research finds, stated as findings, not predictions.
  3. 11The WorksheetsSix of them, from "what's in the bank" to "the state check."
  4. 12Questions for Your CPA and Your Investment Adviser
  5. 13Structured Sale or Seller FinancingPlus the appendix: loss rules for all 50 states and DC.
A look at the worksheets

Worksheet 4: your scoop schedule.

Each year's payment next to the scoop it needs. Your CPA fills in the gain from the payment schedule and the losses from your return. Here it is filled in for the Chens' ten-year level schedule, to show the method.

Worksheet 4: Your scoop scheduleChapter 11 · Illustrative example
YearInstallment gain that year25%-layer portionLosses availableScoop needed to zero the gainGain still taxedLeft in the bank
1$100,000$100,000$140,000$100,000$0$37,000
2$100,000$100,000$77,000$100,000$23,000$0
3$100,000$0$40,000$100,000$60,000$0
Yours$$$$$$
.

Year one: a $140,000 bank against a $100,000 scoop. The $40,000 excess takes $3,000 off other income and $37,000 rolls to year two. Illustrative only; losses are given numbers from the return.

The Loss Bank

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FreePDF · about 60 pages
  • The netting order, the wash sale rule and the 3.8% tax, in plain English
  • Worked examples with every number traced
  • Six worksheets, including the scoop schedule and the state check
  • The state-by-state table: 50 states and DC
  • A "For your CPA" citation box in every chapter

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Hans Goldstein, a licensed insurance agent (CA Insurance License #4273294), will contact you and may discuss insurance products, including annuities.

About the author

Hans Goldstein works on one question: how to sell a building or a business and keep more of what it's worth, legally, on a schedule the seller chooses. He wrote The Waterfall Strategy, on suspended passive losses; The Loss Bank is its companion, on capital losses.

Hans is a licensed insurance agent (CA Insurance License #4273294, NPN 20602398). He has passed all three parts of the IRS Special Enrollment Examination and is not yet enrolled to practice before the IRS. He is not a CPA, an attorney or an investment adviser. He never reviews brokerage statements, holdings or managers; for the loss side, he works only from numbers on a tax return or numbers a CPA provides. He is paid a commission only if a client chooses a structured installment sale funded with an annuity; seller financing, a cash sale or a 1031 pays him nothing from the sale. That is a conflict of interest, which is why the book shows every option side by side. Call or text 213-340-2018.