STRUCTURED INSTALLMENT SALES: DEFERRING THE CAPITAL GAINS BILL BEFORE THE DEAL CLOSES

Most business owners learn the true size of their tax bill after the letter of intent is signed, by which point the useful options have narrowed. A Structured Installment Sale (SIS), built on IRC §453, allows a seller to spread gain recognition across future tax years, managing federal and state brackets and net investment income tax exposure, while receiving payments funded by a highly rated life insurance company rather than the buyer's promise to pay.

This session covers the mechanics: how the payment stream is designed around what the seller actually needs after closing, how the obligation is assigned away from the buyer so default and reinvestment risk are removed, and where the strategy fits among the other approaches an owner is likely to hear about. It also covers timing, because eligibility turns on the sale not yet being binding.

Attendees will leave able to recognize a candidate transaction, explain the structure to a client or co-advisor, and know when to raise it. 

Learning Objectives:

  • Explain how a Structured Installment Sale under IRC §453 defers gain recognition, and how the payment stream is designed around a seller's post-closing income needs and tax brackets.

  • Identify the transaction characteristics that make a sale a strong candidate, including deal size, asset composition, entity structure and the seller's income picture after closing.

  • Describe the roles of the assignment company and the funding carrier, and explain how third-party assignment removes the buyer default and reinvestment risk inherent in a traditional installment note.

  • Recognize how the progression of a transaction — typically from letter of intent to definitive agreement to closing — governs availability, and identify the point after which the strategy can no longer be implemented.

  • Raise the strategy effectively with a client's CPA, attorney or M&A advisor, anticipating the questions each will ask. 

Event Details

Date: Tuesday, April 27, 2027
Time: 1:00 pm - 2:00 pm
Where: ON24
Cost:
Value Acceleration Knowledge Hours: 1
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Who Should Attend?

  • Attorneys

    You have close relationships with clients, and can benefit from being the first advisor to introduce the idea of exit planning.

  • CPAs/Accountants

    Owners participating in the State of Owner Readiness research continue to indicate that you are the No. 1 "Most Trusted Advisor." You are a natural fit to lead the exit planning team and deepen your relationship (and retention) of next generation owners.

  • Wealth Managers

    You’re a skilled relationship person. Being entangled into your clients’ professional lives matters as you build a strategy to manage their wealth upon them harvesting it from their business. Exit planning allows you to build a deeper relationship with your client, expands your COI network, while giving you an early seat at table well before the liquidity event.

  • Investment Bankers

    Only 2 of every 10 businesses that come to market actually sell. Learn how exit planning can bring attractive AND ready business to your purview.

  • Valuation Analysts

    Valuation is both a billable engagement AND an opportunity to provide owners some perspective on how to accelerate value drivers (and deal with value killers). Use exit planning to make that valuation into a longer term value acceleration engagement.

  • Financial Advisors

    One of the critical ‘legs of the stool’ is personal financing planning. An owner must have a strong financial plan & contingency plan post-transition to enable them to thrive in the next act of the lives personally and financially. Exit planning brings this future mindset into the present. Exit is now.

  • Insurance Professionals

    Exit planning addresses the 5 D's. So do you. Approach the risk conversation differently with exit planning.

  • Strategic Consultants

    One of the most critical roles in exit planning is building transferable value. Strategic consultants have the ability to expand options and drive rapid business value that affect performance today.

  • Estate Planners

    Exit planning is a natural fit for estate planners who want to operate more holistically with their owner clients.

  • Other Professional Advisors

    Regardless of your unique specialty, there is seat at the exit planning table for you. Learn more at www.EarnCEPA.com.

  • Family Business Advisors

    More than 50% of lower middle market business owners would prefer to transition to the next generation. Help them succeed with exit planning strategies.

  • Commercial Lenders

    One of the best relationships a business owner makes is with their banker. How can you help your corporate clients think about the future and ensure financial continuity? Answer: exit planning.

  • Mergers & Acquisition Advisors

    Proper exit planning causes less deals to fall through at the last minute. Connect with CEPAs to build your healthy deal flow network.

  • Business Owners & Their Trusted Advisors

  • Business Owners

  • Other Business Professionals

  • Business Consultants

  • Professional Advisors

  • Members of Family Business Boards

  • Private Business Owners

EXIT PLANNING IS GOOD BUSINESS STRATEGY

The Exit Planning Institute, provides Financial Advisors, Accountants, Consultants, and other advisors of business owners with the critical education to differentiate themselves and add value to their existing client relationships through a credential, conference, courses, and content. Download the CEPA brochure for more information.

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