IRS Publication 537 · IRC Section 453

The 537 Installment Sale Trust

Defer 100% of capital gains taxes on the sale of appreciated assets — legally, with full liquidity, and a step-up in basis for your heirs.

What Is the 537 IST?

A proven tax deferral strategy with 3,800+ successful transactions and zero IRS audits

The 537 Installment Sale Trust is a trust arrangement that leverages IRC Section 453 — the installment sale method that has governed tax deferral since 1921. When you sell an appreciated asset, instead of paying 20-40% in immediate taxes, the trust receives your sale proceeds and issues you a secured promissory note.

The name comes from IRS Publication 537, which is the IRS's own guide to installment sales. This is not a loophole or aggressive tax shelter — it's a strategy built on over a century of established tax law, originally derived from Ernst & Ernst (now Ernst & Young) strategies from the 1970s.

Your sale proceeds are professionally managed through the Model Q® investment strategy, generating quarterly income while the full pre-tax amount continues to compound — including the 20-40% that would have otherwise gone to the IRS.

Taxes Deferred

Federal Capital Gains15-20%
Net Investment Income Tax (NIIT)3.8%
Depreciation RecaptureUp to 25%
State Capital Gains0-13.3%
Combined Savings20-40% of sale price

By the Numbers

3,800+
Transactions Completed
0
IRS Audits
20+
Years of Track Record
100+
Years of Tax Law Precedent

How Does It Work?

Four straightforward steps from asset sale to tax-deferred income

1

Asset Transfer to Trust

You transfer your appreciated asset to the 537 IST in exchange for a secured promissory note. No tax is triggered at this stage because no gain is recognized — this is a carryback transaction against the trust.

  • Trust must be established BEFORE the sale closes (14-30 day setup)
  • Two purchase agreements mirror each other exactly (Seller→IST, IST→Buyer)
  • Seller receives secured promissory note — not cash — so no constructive receipt
2

Trust Sells to Ultimate Buyer

The IST sells the asset to the final buyer at the same price. Because the trust purchased and sold at the same price, there is no gain to the trust — the transaction is tax-neutral.

  • Sale proceeds flow directly into trust bank account at City National Bank
  • DACA (Deposit Account Control Agreement) protects funds from commingling
  • Independent third-party trustee ensures arms-length compliance
3

Trust Invests Proceeds

The full pre-tax proceeds are invested through the Model Q® dual-asset strategy — a 50/50 split between professionally managed ETFs and Fixed Index Annuities, cleared through Charles Schwab and A-rated carriers.

  • ETF portfolio managed by Christian Ramsey, AIF® at institutional level
  • Fixed Index Annuity provides principal protection with market upside
  • Three layers of compounding: interest on principal, interest on interest, interest on deferred taxes
4

Receive Quarterly Income

The trust pays you quarterly interest on your secured promissory note — typically 6% annually. Taxes are deferred until you actually receive principal payments, and the note can be refinanced at maturity to continue deferral indefinitely.

  • Standard 10-year note with unlimited refinancing options
  • Quarterly distributions provide predictable retirement income
  • Full liquidity — access funds within 3-7 business days with no penalties

Why Is It IRS Compliant?

Built on established tax law, not loopholes — with structural safeguards that ensure compliance

IRC Section 453 Foundation

The installment sale method has been part of the Internal Revenue Code since 1921. IRS Publication 537 is the IRS's own guide to these transactions. This is not a novel or untested strategy.

No Constructive Receipt

The seller cannot own the trust, cannot be the trust beneficiary, and receives only a secured promissory note — not cash. The trust has a genuine business purpose with independent third-party administration.

No Third-Party Loans

Unlike some aggressive tax deferral structures, the 537 IST uses no third-party loans or artificial financing. The transaction is a genuine installment sale with real economic substance.

Trust Security & Safeguards

Independent Trustee

CB Admin Services or IST Admin Services — professional, third-party fiduciaries

Bank Custody

Separate trust bank account at City National Bank with DACA protection

Insurance Coverage

Fidelity Bonds and Errors & Omissions (E&O) insurance on all administration

Authentication

DocuSign authentication, mobile app verification for all wires and ACH transfers

Annual Reporting

Trust tax returns prepared by CPA, K-1 and 1099-INT issued to note holders

Note Holder Rights

Approve/reject investments, dictate income timing, refinance or terminate at will

Key Benefits

Why thousands of sellers choose the 537 IST over traditional sale strategies

Tax-Deferred Growth

The full pre-tax amount stays invested and compounds — including the 20-40% that would have gone to taxes. Three layers of compounding: interest on principal, interest on interest, and interest on deferred taxes.

Guaranteed 6% Income

Receive predictable quarterly income at a 6% annual withdrawal rate — significantly higher than the traditional 4% retirement rule. Income sourced from ETFs when markets are up, annuities when markets are down.

Asset Protection

Trust assets are segregated in separate bank accounts with DACA protection, Fidelity Bonds, and E&O insurance. Professional fiduciary administration provides an additional layer of security.

1031 Exchange Safety Net

If a 1031 Exchange fails within the 45-180 day window, proceeds can be redirected into a 537 IST. Q1031's qualified intermediary language is approved for reversion to the installment method.

Step-Up in Basis

The promissory note qualifies as a "security" under Reves v. Ernst & Young (1990). Securities receive a step-up in basis at death — eliminating all deferred taxes for your heirs.

Full Liquidity

No surrender charges, no penalties, no lock-up periods. Access your funds within 3-7 business days. Refinance your note at maturity or take partial distributions anytime.

Liquidity Comparison

How the 537 IST compares to other tax deferral and trust strategies

Feature537 IST1031 ExchangeDelaware Statutory TrustIrrevocable Trust
Liquidity3-7 daysNone (tied to property)Limited (10+ year hold)None (irrevocable)
Tax Deferral100% deferred100% deferred100% deferredPartial
Step-Up in BasisYes (note = security)Yes (at death)Yes (at death)No
Replacement Property RequiredNoYes (like-kind)Yes (DST property)N/A
Strict DeadlinesMust setup before close45/180 day rules45/180 day rulesNone
Income Stream6% quarterlyRental income only4-6% annualVaries
ControlFull note holder rightsFull property ownerPassive investorNo control
Management RequiredProfessional (hands-off)Active (tenants, repairs)PassiveTrustee managed

The Model Q® Investment Strategy

A dual-asset approach designed for consistent income with downside protection

ETF Portfolio (50%)

Professionally managed by Christian Ramsey, AIF® at institutional level — similar to how CalPERS and CalSTRS manage public pension assets. Securities cleared through Charles Schwab.

  • Tactical allocation for systemic risk (tariffs, COVID, geopolitical)
  • GIPS-compliant returns with conservative projections
  • Income sourced from ETFs when markets are up

Fixed Index Annuity (50%)

Principal protection with upside market participation through A-rated insurance carriers including Nationwide, Allianz, Fidelity, Athene, North American, and Penn Mutual. Eliminates sequence-of-returns risk.

  • Principal protection — your floor value never decreases
  • Income sourced from annuity when markets are down
  • SEI and Schwab platform cleared

Three Layers of Compounding

1

Interest on Principal

Your base investment returns from both ETFs and fixed index annuities.

2

Interest on Interest

Reinvested earnings compound over time, accelerating growth year over year.

3

Interest on Taxes Deferred

The 20-40% that would have gone to the IRS also earns returns — this is the compounding advantage unique to tax deferral.

Step-Up in Basis: The Ultimate Estate Benefit

How the 537 IST can eliminate deferred taxes entirely for your heirs

The secured promissory note you hold against the 537 IST qualifies as a “security” under the landmark Supreme Court case Reves v. Ernst & Young (1990). Why? Because the note has variable/upside potential — it can increase in value beyond its face amount.

Securities receive a step-up in basis at death. This means when your heirs inherit the promissory note, its cost basis is reset to its current fair market value. The result: all deferred capital gains taxes are eliminated.

This is a critical differentiator from Deferred Sales Trusts, which use fixed installment notes without upside participation. Fixed notes do not qualify as securities and do not receive a step-up — meaning heirs inherit the deferred tax liability.

537 IST at Death

Original Sale$2,000,000
Deferred Taxes$626,000
Note = Security?Yes
Step-Up in Basis?Yes
Taxes Owed by Heirs$0

Who Can Benefit?

The 537 IST is designed for sellers of highly appreciated assets across multiple categories

Investment Real Estate Owners

Exit active management of rental properties — no more tenants, toilets, and trash. Consolidate multiple properties into one trust. Extract basis on transactions over $1M.

Examples: Rental properties, commercial buildings, multi-family, land

Business Owners

Selling your business doesn't have to mean losing 20-40% to taxes on day one. Structure your exit to maintain comparable income without the 60-80 hour work weeks.

Examples: Sole proprietorships, partnerships, LLCs, S-Corps, C-Corp stock sales

Personal Residence Sellers

For homes valued above the federal exclusion ($250K single/$500K married), the 537 IST defers gains on the amount exceeding the exclusion. Extract your original basis + improvements tax-free.

Examples: High-value primary residences, vacation homes

Failed 1031 Exchange Participants

If your 1031 Exchange is at risk of failing — can't find replacement property, deadline approaching — the 537 IST serves as a safety net. Convert to installment method within the exchange window.

Examples: Exchanges at risk of the 45-day or 180-day deadline

High-Value Asset Holders

Art, jewelry, patents, cryptocurrency, and other appreciated personal property qualify for installment sale treatment. Minimum transaction size is typically $500,000.

Examples: Art collections, intellectual property, crypto holdings

Frequently Asked Questions

Find Out How Much You Could Save

Schedule a complimentary consultation to receive a personalized pro forma analysis showing your exact tax deferral potential with the 537 IST.

537 Installment Sale Trust (IST) | Kevin Brunner