Just Posted: Structured Installment Sales Case Study on Our YouTube Channel

Just Posted: Structured Installment Sales Case Study on Our YouTube Channel

August 18, 2023 – For those seeking to defer, reduce, or in some rare instances, completely eliminate capital gains taxes on the sale of a business, real estate, or other qualifying appreciated asset, perhaps no method of tax deferral holds more promise than a Structured Installment Sale (SIS). They’re easy to implement, straightforward, and, when implemented properly, fully compliant with Section 453 of the Internal Revenue Code.

In our latest YouTube Channel offering, we offer a Structured Installment Sale Case Study No. 3 as a helpful peek inside the analysis one might go through to determine whether or not a SIS is right for them. In this episode we go through the analysis to compare and contrast a hypothetical cash sale of a business for $2,000,000 to a SIS for the same amount of money.

The net result? a SIS saves the client over $200,000 in capital gains taxes!

The video is only seven minutes long and makes a compelling case for anyone selling their business. For those reluctant to sell because of the tax hit they anticipate, a Structured Installment Sale can help ameliorate that worry by letting sellers keep more of their sales proceeds for themselves instead of sending them off unnecessarily to the federal and state government.

Structured Installment Sales. Be sure to check out our other publications and videos on this money-saving topic.

Structured Installment Sales for Tax Efficiency

July 12, 2021 – Since my article in Realty Times on structured installment sales last year, housing appreciation has continued unabated and interest by many in “cashing in by cashing out” of their paper wealth has increased.

With some talk of interest rates ticking up in the coming year and phase four of the real estate cycle, recession, overdue, this seems an ideal time to take advantage of market demand by selling appreciated real estate.

But then there’s the tax sting which keeps many from selling.

Because capital gains on assets held over two years on anything above $250,000 (single) or $500,000 (married filing jointly) for a primary residence can be taxed at 0%, 15%, or 20% depending on the amount of gain, strategically selling real estate to minimize these taxes is just plain smart.

Add in state capital gains taxes which can siphon away even more of your equity when selling and you have a lot of reasons for considering a structured installment sale when you sell.

The Four Phases of the Real Estate Cycle

The four generally accepted phases of a real estate cycle are recovery, expansion, hyper supply, and recession. Depending on who you want to believe, these real estate cycles can last anywhere from 7-to-10 years to as many as 18 years.

We’re not here to argue which phase we’re in right now and can’t predict with any degree of accuracy when things will change, and supply starts to outstrip demand.

We just know that when someone’s ready to sell and wants to defer, reduce, or eliminate capital gains taxes, we can help.

Our firm fields calls from interested parties from across the country nearly every week and we’ve helped many clients save money on their transactions.

Structured installment sales are supported by U.S. tax law and are surprisingly easy to implement.

Our challenge is not enough people have heard about this option yet despite its availability for decades.

Having helped clients save tens of thousands of dollars on capital gains taxes, we’re urging anyone contemplating selling a business or real estate to look into the benefits of doing so using a structured installment sale.

Photo by Tierra Mallorca on Unsplash

Roubini has a bad feeling on this one, all right?

March 3, 2020 – Remember the line in Platoon when Sgt. O’Neill (John C. McGinley) expresses his concerns about a pending military conflict with Staff Sgt. Barnes (Tom Berenger)?

“Bob, I got a bad feeling on this one, all right? I mean, I got a bad feeling. I don’t think I’m gonna make it outta here! D’ya understand what I’m sayin’ to you?”

Sgt. Red O’Neill

While the prospects of seeing one’s entire life savings evaporate due to fallout from a global pandemic pale in comparison to the psychological trauma experienced by the brave men and women who experience the harsh realities of war, this line came to mind when I read yesterday’s MarketWatch article quoting economist Nouriel Roubini who sees bad things ahead for the market.

“I expect global equities to tank by 30% to 40% this year.”

Nouriel Roubini

Investors may want to heed Roubini’s advice given he was one of the few economists to correctly predict the 2008 financial crisis. To avoid financial catastrophe, Dr. Roubini is urging people to seek safety NOW.

And he’s not the only one doing so. About a year and a half ago, we published a blog citing other experts suggesting clients may also wish to pare down their exposure to stocks in favor of safer options.

Where Can You Find Safety?

In addition to buying safe bonds, structured settlements and retirement annuities remain some of the safest choices for those who require certainty.

Even with interest rates at or near historic lows, structured settlements and retirement annuities remain attractive alternatives. Something about making some money (especially when there’s a decided tax advantage) is more attractive than losing a lot of money.

Consider all these available options clients are currently talking to us about:

Tax-free structured settlements for physical injuries.

Tax-deferred structured settlements for nonphysical injuries.

Tax-efficient structured installment sales to reduce or eliminate capital gains taxes when selling qualifying appreciated assets or businesses.

Fixed indexed annuities which allow participants to benefit from market ups but shield them from market downs.

Market indexed structured settlement options with downside protection.

A structured settlement option that accounts for future interest rate increases.

Multi-Year Guaranteed Annuities (MYGAs) for “better than CD” rates.

Even if you still have faith in the market for the long-term, almost everyone would be wise to consider converting at least some of their safety net to something that is actually safe.

And if Dr. Roubini ends up being right, there’s no time like the present to make a move before things get really bad.

Let us know if we can help save you from drowning.

Structured Settlements: Structured Installment Sales

Eleventh in a series of blog posts dedicated to helping clients decide when a structured settlement should be considered.

Today’s Installment (npi): Structured Installment Sales

February 5, 2020 – For this segment in our series of educational offerings, we’re going off-topic slightly because we wish to present a structured settlement offshoot product designed to help clients defer and sometimes eliminate capital gains taxes when selling qualifying appreciated assets: Structured Installment Sales.

Be sure to visit our companion site: MyStructuredSale.com

Real estate investors, business owners, property owners, and the realtors, business brokers, lawyers and accountants who represent and advise them will find this simple-to-implement alternative to traditional sales worthy of their time.

As any accounting major can tell you, deferring taxes and accelerating deductions is one of the fundamental tenets of accounting.

Structured installment sales help conveniently with the deferring taxes part of that formula.

The process is simple:

Step 1: Buyer and seller negotiate a price for the property or business.

Step 2: Seller decides how much of the net settlement proceeds to defer.

Step 3: Seller contacts a firm specializing in structured installment sales annuity quotes. (We hear Finn Financial Group is pretty good!)

Step 4: Terms of the structured installment sale are incorporated into the sales agreement and closing documents.

Step 5: At closing, all relevant documents are executed, and the funds dispensed to the appropriate parties.

Although Treasury regulations have permitted installment reporting for taxes since 1918, it wasn’t until 1980, when Congress passed Public Law 96-471, that Section 453 of the Internal Revenue Code was modified laying the foundation for what would become known as Structured Installment Sales. Publication 537 contains information on installment sale eligibility requirements.

In 2005, Allstate Life, in an effort to explore expanded applications for structured settlements, researched a utilization in the appreciated asset world and rolled out a product they called a structured sale. Prudential soon followed but just as the concept was beginning to gather major traction, the Great Recession hit wiping out investment equity and the opportunity to defer taxes with it.

Now, with property values up over the past decade, this tax deferring option is poised for a major resurgence. So much so that one of the largest insurers in the world, MetLife, has chosen to offer Structured Installment Sales through its specialized, appointed agency force.

Click [HERE] to watch MetLife’s 1:12 promotional video on the topic.

Structured installment sales are also available through Independent Life as well as an option funded by U.S. Treasuries.

When a structured installment sale is being considered, the parties involved need to be cognizant of a few basic rules:

A decision to defer sales proceeds must be made prior to finalizing any sales agreement to avoid constructive receipt;

Terms of the deferral should be incorporated into any sales agreement;

Plan design and deferral options may be limited;

Buyer and seller must execute certain required documents prepared by the firm implementing the structured installment sale;

The annuity must be funded directly by or on behalf of the buyer through the closing process.

The Tax Cuts and Jobs Act gives even added incentives for certain taxpayers to defer recognition of gain into future years. Those contemplating selling any qualifying appreciated asset would be well-advised to consider doing so via the structured installment sale method.

Unless they like paying taxes you can otherwise avoid.

Car Accident Statistics

May 2, 2019 – Although Distracted Driving Awareness Month officially ended Tuesday, we feel no shame in reminding our clients that attentiveness behind the wheel and vigilance in carrying out driving responsibilities should never take a vacation.

Thus, our belated post on the topic.

If we had our way, however, the U.S. Department of Transportation would change it to Distracted Driving Awareness Century.

One of the best sites we’ve found to highlight our driving habits and the human cost that comes with our reliance on two-or-more-wheeled motorized transportation is (click the link):

100+ Car Accident Statistic for 2019

The site provides verifiable, irrefutable statistics reminding us of our duty to our fellow travelers and of the potential consequences when our attention spans lapse.


When You’re Sixty-Four

GuitarSeptember 14, 2015 – Even some of the staunchest Beatles fans are surprised to learn that one catchy tune from the Sgt. Pepper’s Lonely Hearts Club Band album about reaching a certain age was one of the first songs Paul McCartney ever wrote, by some accounts as early as age 16 when the band was still calling itself The Quarrymen.

Give “the cute Beatle” points for looking almost fifty years into the future to ponder love, life and, even if he was doing so unintentionally, joint life expectancy.

Today, married couples probably don’t think enough about joint life expectancy but if they want to make sure their retirement assets last as long as they do, they should.

Fortunately, one “band” that calls itself the Society of Actuaries (SOA) thinks about this kind of thing a lot. These studious lads (and lasses) may never have charted any singles but the work they do is as vital to life as music, if not more so.

In its Phase 1 (of a four-phase project) Baseline July, 2015 research newsletter on “Optimal Retirement Income Solutions in DC Plans,” the SOA authors analyze various retirement income generators (RIGs) with the goal of evaluating the pros and cons of each method to find the optimum solution for ensuring steady cash flow for life.

(Full Disclosure: One of the authors, Dr. Wade Pfau, was one of my professors during my Retirement Income Certified Professional® studies through The American College)

Quotable Highlights

This report is YET ANOTHER in a series of studies we keep finding that points to the advantage of life annuities to meet one’s future income needs.

Here are a few of the highlights we especially liked with our own emphasis added:

“RIGs that pool longevity risk (annuities) provide higher expected lifetime retirement income than investing approaches that self-fund longevity risk.” (p. 8)

“An effective compromise may be retirement income solutions that dedicate a portion of savings to annuities and remaining assets to investing solutions to realize the advantages of both.” (p. 9)

(NOTE: Check out some of our recent newsletters and blog posts. We’ve been advocating this approach for years.)

“Traditional annuities produce higher expected average retirement income than SWP (Standard Withdrawal Plan) strategies due to longevity pooling.” (p. 12)

This last one is worth analyzing a bit further.

The classic “four percent” draw down approach (a common SWP where retirement assets are invested in a mix of stocks and bonds and retirees withdraw four percent of the principal each year to live on hoping what remains will earn enough to allow the money to last a lifetime) has recently been called into question.

So much so than this SOA paper didn’t even consider this approach as an option since prior research “showed this method failed (savings were exhausted) in unfavorable investment scenarios.” (p.14)

    Translation: The four percent thing works great when it works. But it doesn’t always work.

Saving the best part of the report for last, it doesn’t get any more straightforward than what the authors concluded about single premium immediate annuities (SPIAs) for a hypothetical sixty-five year old female with $250,000 in retirement assets:

“SPIAs produce highest income with lowest risk” (p. 23)

You’ll Be Older, Too

For married couples, the case for annuities is even more compelling.

Everyone has a statistical probability of living to a certain age. But when that same person marries, the chance that one of them will live beyond their individual life expectancy increases by a significant factor.

NOTE: This calculus also extends to same-sex married couples by the way though it is unknown to what extent outcomes might vary. Additional research is needed.

If continuation of cash flow to a surviving spouse is important to ANY married couple, placing value on these statistical probabilities should be a top priority.

Here’s a quick look at how this plays out for a sixty-four year old married (male, female) couple courtesy of our bean-counting friends at the SOA (individual chances in parentheses):

72% chance one of them will live to age 85 (Man: 41%, Woman: 52%)
45% chance one of them will live to age 90 (Man: 19%, Woman: 31%)

18% chance one of them will live to age 95 (Man: 6%, Woman: 18%)

If want to see what YOUR OWN chances of living to a certain age will be, Vanguard has a nifty interactive “Plan for a long retirement” tool you might like. It’s a fun (and possibly frightening) exercise.

So whether you’re trying to decide what to do with an anticipated personal injury settlement, a larger-than-usual attorney fee or the current 401(k) balance you’ve managed to accumulate during your working life, I hope this information on life expectancy has given you something to think about.

Guitar image courtesy of Iamnee at FreeDigitalPhotos.net

Our “Best” Structured Settlement Endorsement Yet


With great pride we announce today our firm’s inclusion in Best’s Directory of Recommended Expert Service Providers in its Structured Settlement listing.

America’s premier independent insurance rating organization, A.M. Best Company, Inc. is  designated as a Nationally Recognized Statistical Rating Organization (NRSRO) by the National Association of Insurance Commissioners (NAIC).

Directory listing eligibility is based upon an applicant’s “reputation, character and industry experience” and requires endorsements from past clients and peers familiar with the candidate’s credentials.

We are honored to be acknowledged as one of the nation’s only Structured Settlement Experts recognized by A.M. Best and are humbled by the outpouring of support received from the many attorneys, claims professionals and insurance industry veterans who gave so willingly of their time to validate our candidacy when contacted by this respected organization.

We share this distinction with all of you who make our success possible by trusting us with all your structured settlement and specialty annuity planning needs.

Thank you to everyone who participated in the vetting process and thank you all for continuing to believe in us.  We appreciate the opportunity to be of service to YOU.

Best wishes for continued Struccess!

2013 So Far . . .

February 17, 2013 – Before the year gets away from us as years are wont to do, I thought we’d pause for a moment to reflect upon the number of people whose lives have been positively impacted in these first few weeks of 2013 as a result of our firm’s involvement in many changes in our offices like our new call centre furniture and new buildings.

Helped secure the futures of five minor children by aiding their parents and their attorneys with the placement of their structured settlement choices following resolution of their personal, physical injury claims on five separate settlements.Since January 1, 2013 we have:

  • Structured Settlement RecipientHelped a young man who was severely injured on the job with the settlement of his workers’ compensation settlement.  Because his ability to earn a living had been compromised, we helped him secure his financial future with100% income tax-free structured settlement cash flows he can never outlive.  In addition, we helped him find affordable health care since he was denied coverage and otherwise would have been uninsured.
  • Helped a baby boomer attorney tired of exposing his life savings to market risk secure his retirement funds by rolling them over to some non-structured settlement annuities which will provide guaranteed future income to meet his anticipated future needs without worry of market volatility.
  • Assisted two clients whose situations required the use of Special Needs Trusts in order to protect their public benefits.
  • Structured SaleProvided guidance to two clients in the process of of selling their appreciated assets who are seeking to defer capital gains taxes utilizing a Structured Sale.  Sales are pending and they are looking forward to achieving the tax deferral they desire.
  • Consulted with two individuals embroiled in employment disputes in helping them analyze the tax savings potentially realized by choosing a Non-Physical Injury Structured Settlement at settlement.
  • Attended six mediations or trials at the request of claims professionals or attorneys to aid in the negotiation and resolution process.
  • Met with a number of attorneys, financial planners, claims associates, life company partners and others to discuss matters of mutual interest.
  • Attended a Board of Directors meeting as an Officer of the National Structured Settlements Trade Association.


And this doesn’t even count responding to the countless calls and emails we receive on a daily basis from those seeking out our expertise on a variety of related issues.

Our firm is committed to helping clients achieve long-term financial security through the effective use of structured settlements and related products and services.

So whether you need assistance with structured settlement choices or are just looking for expert advice on how to arrange your financial affairs, call us.  Chances are good we can help you.  We look forward to being of service to YOU!

Is Oil Boom for California Nigh?

January 16, 2013 – Yesterday’s CNN/Money column “California Shale Boom Possible” was a timely article for us to remind our clients about a money-saving option available to those who lease their land for oil and gas exploration.

In August of 2011 we announced the availability of a new application of the structured settlement concept designed to help landowners defer taxes on the bonus payments they typically receive for leasing their land.

Gas Drilling RigIn addition to potential future royalties, landowners are commonly offered substantial up-front cash bonus payments as an inducement to leasing the land for prospecting.  Because this bonus payment is fully taxable, the Structured Oil & Gas Lease Bonus Option can help spread the tax burden out over a number of years saving the taxpayer money.

To learn more about this unique approach to saving money on oil & gas leases, visit our companion website at:



New Tax Deferral Strategy for Business Brokers and Realtors

The same tax deferral benefit enjoyed by contingency fee lawyers for years is now available for another group of professionals often looking for a sensible tax break:  Business Brokers and Real Estate Agents.

This is terrific news for any realtor or business broker who has always sought a way to safely and conveniently defer taxes on commissions they earn for implementing deals for their clients.  The benefits to this method of planning are many:

  • Deferring income taxes allows this group of professionals to balance out the highs and lows of a very cyclical business;
  • Sums deferred earn pre-tax interest offering the same advantage as 401(k) and similar plans;
  • Participants can arrange their income needs around marginal tax brackets to keep more of what they earn;
  • Brokers can potentially avoid or reduce their Alternative Minimum Tax (AMT) bite;
  • Those with long-range financial goals can secure their futures by arranging supplemental, tax-advantaged cash flows in their retirement years guaranteed by a highly rated life insurance company.

Typically, when a realtor or business broker facilitates a sale, they are paid a commission based on a percentage of the sales price of the business or property.  Commission is paid in the year of the sale at closing and the agent or broker promptly (and presumably begrudgingly) estimates the amount of this sum they need to set aside for Uncle Sam.

But now, thanks to a major life insurance company, successful agents and brokers can now arrange to more effectively manage their commissions.

Allstate Life, rated A+ by A. M. Best, announced today that they are rolling out this attractive option as an enhancement to the Structured Sale offering made available through a limited distribution channel several years back.  Through an arrangement with Allstate International Assignments, Ltd. which currently handles their Structured Sales offering, those who qualify can take advantage of this unique opportunity.

When compared to earning commissions, paying taxes and investing the remainder, some professionals estimate they would need to earn a rate of return well in excess of the historical stock market average just to equal what the Structured Commission pays (depending on assumptions made about future tax brackets).  The difference here, of course, is the lack of stock market risk since guaranteed payouts are considered “risk-free” in financial planning parlance.

CAVEAT:  Key to implementation is the phrase “those who qualify.”  The Business Broker or Realtor must be considered a “Service Provider” pursuant to Section 409A of the Internal Revenue Code.

But there’s more. 

Certain paperwork must be prepared by someone representing the life company (as of now, just Allstate) who has been authorized to implement these special-purpose transactions.  Because of the unique nature of this particular offering, the distribution channel has historically been limited to those familiar with the special paperwork and sequence of events which must be strictly adhered to in order for the matter to be properly consummated.  Do NOT assume your neighborhood insurance agent will be familiar with this.

So for now, since this particular missive has run longer than intended, suffice it to say “We Can Help!”  The Finn Financial Group is proud to be among a select group of firms in the United States chosen to help effectuate Structured Sales and the accompanying broker and agent commission deferral.  Call for an analysis or for additional information BEFORE the transaction is complete.  Because timing is everything, it’s critical the terms of the deferred commission be chosen before the sales agreement is finalize and the deal concluded.

Finn Financial Group