Defer the tax.
Guarantee the income.
When you sell a business, a building, or land for a large gain, a Structured Installment Sale spreads the capital-gains tax across years — and turns the proceeds into a secure, insurer-backed income stream.
One strategy. Three ways to experience it.
The SIS Resource Center adapts to the question in front of you — whether you are selling, advising, or simply trying to understand how the transaction works.
See what your sale could become.
Estimate tax timing, compare a lump sum with a structured schedule, and begin designing income around your goals.
Run my numbers Path 02 · AdvisorBring a defensible strategy to the table.
Access tax mechanics, implementation guidance, specialty resources, citations, comparison tools, and client-ready explanations.
Open professional resources Path 03 · LearnWatch the transaction come to life.
Follow the seller, buyer, assignment company, and insurer through a guided interactive story built to make the structure intuitive.
Experience the storyDo not just read about the SIS. Step inside it.
The Interactive SIS Story turns a complex tax and payment structure into a guided visual journey. Select the seller’s purpose, watch the transaction move, and see how the sale is reshaped into future income.
Four parties. One coordinated flow.
At closing, the obligation moves away from the buyer and is funded through an insurer-backed payment arrangement. The seller receives payments according to the selected schedule and reports gain as payments arrive.
Seller
Chooses installment treatment and a payment schedule before closing.
Buyer
Acquires the asset and sends the structured portion of the price at closing.
Assignment Company
Accepts the payment obligation and releases the buyer from future payments.
Life Insurer
Funds the scheduled stream through its claims-paying ability.
How much could spreading the gain save you?
Use your actual sale assumptions to compare the timing of federal tax, net proceeds, and annual income under a taxable lump sum and an SIS.
Illustration only. Results depend on basis, recapture, income, state tax, schedule, and other transaction facts.
Different assets. Different lives. One recurring problem: a large taxable gain.
The SIS can apply to many appreciated capital assets when the seller is willing to exchange immediate liquidity for a designed future payment stream.
Turn decades of enterprise value into an income plan.
Explore a seller’s goals, tax position, timing, and liquidity needs before selecting a schedule.
Sell without acquiring replacement property.
Convert land value into generational income.
Coordinate tax, legal, and transaction advisors.
Pair installment treatment with the §121 exclusion.
Every answer should lead naturally to the next question.
Move from education to modeling, comparison, state tax research, professional guidance, and implementation detail without leaving the SIS ecosystem.
Compare the alternatives
See SIS, §1031, DST, CRT, Opportunity Zone, seller note, and lump sum trade-offs side by side.
Open comparison →State Tax Center
Research conformity, sourcing, withholding, residency changes, PTE elections, and state-specific traps.
Explore the map →Professional Resources
Specialty sections for tax advisors, transaction advisors, real estate professionals, lenders, and legal advisors.
Choose a profession →Knowledgebase
Go from plain-English fundamentals to the tax framework, rulings, safety, risks, and implementation.
Open the knowledgebase →Confidence comes from the structure — and the quality of the carrier behind it.
An SIS is designed to remove ongoing buyer-credit exposure through assignment and to fund scheduled payments through a life insurer. Carrier financial strength, statutory reserves, regulatory oversight, and diversification remain important due-diligence considerations.
The buyer is released after the payment obligation is assigned and funded.
The scheduled payments depend on the selected insurer’s financial strength.
Life insurers operate within state insurance capital and reserve requirements.
Large payment obligations may warrant additional attention to carrier concentration.
Payments
The federal answer is only half the answer.
State conformity, source rules, withholding, residency changes, entity structure, and payment timing can materially change an SIS analysis.
Use the State Tax Center before closing to identify the questions that belong in the tax-planning conversation.
Model your sale with an SIS Specialist.
The right answer depends on your asset, basis, income, liquidity needs, state, and timeline. Share the outline of your sale and begin with a side-by-side conversation.