Profit Preservation: Tax-Deferred Strategies for Selling Your Business

Admin • March 8, 2024

You’ve built a thriving business and poured your heart and soul into it, and now it’s time to sell and reap the rewards. Congratulations! That’s a monumental step, not just in terms of the immediate financial windfall but also for your long-term financial health. It’s an exhilarating, albeit slightly nerve-wracking, phase. 

But before you pop the champagne and sail off into the sunset, let’s talk strategy, specifically tax strategy. Yes, I know “tax” isn’t the most thrilling word in our vocabulary, but stick with me because Uncle Sam has his eye on a piece of the pie. 

Selling a business can trigger a significant tax bill, leaving you feeling like you just worked hard for someone else. Understanding and leveraging tax-deferred opportunities can significantly impact how much of that sale you get to keep and grow over time. 

What Does Tax-Deferred Mean?

Tax-deferred means you can delay paying taxes on investments and their earnings until you withdraw the money. This allows your money to grow tax-free, potentially leading to significant savings. Often, when money is withdrawn during retirement, you will be in a lower tax bracket.

Here’s an example: Imagine you sell your business for $1 million, resulting in a $500,000 capital gain. If you were to pay taxes on that amount right away, it could leave a hefty dent in your pocket. But by utilizing a tax-deferred strategy, you can hold onto that money and invest it, allowing it to grow tax-free until you withdraw it later. The longer you leave it untouched, the more it can compound, leaving you with a much larger sum.

Tax Strategies for the Savvy Seller

There are several tax-deferred opportunities available that can help you minimize your tax burden. Let’s explore some options you might want to consider.

1. Seller Financing

Have you ever thought about being the bank? In seller financing, you extend credit to the buyer to purchase the business. The buyer pays you back over time with interest. The catch? You don’t get all your money upfront. Still, it can spread the tax burden over several years, potentially keeping you in a lower tax bracket and reducing the immediate tax hit.

Pros:

  • Spreading sale proceeds over several years minimizes annual capital gains taxes for tax benefits.
  • Seller financing can speed up the closing process since there’s no waiting on the bank’s loan approval.
  • Offering seller financing widens the potential buyer pool.
  • Sellers may command a higher sales price because they’re offering financing.
  • Seller financing generates consistent interest income for sellers.

Cons:

  • One of the most significant risks for sellers is the buyer defaulting on the loan. 
  • Deferred full payment to sellers.
  • Crafting a seller financing agreement requires legal assistance to ensure the contract protects both parties. This can add to the transaction’s costs and time.
  • Sellers manage loans and address payment issues.

2. Installment Sales

Similar to seller financing , installment sales allow you to defer taxes by receiving the proceeds over time. You only pay taxes on the portion of the gain you receive each year. This can be a great way to manage your tax liability and keep more money working for you over the sale period.

Pros:

  • Pay tax only on received installment profits, deferring tax liability.
  • Installment sales enhance buyer accessibility beyond traditional financing.
  • Earn interest on financed amounts for additional income.

Cons:

  • Risk of buyer loan default.
  • Delayed full payment of sale proceeds.
  • Potential for lower future income if interest rates rise.
  • Possible decline in property value over time, complicating resale after default.

3. Qualified Opportunity Funds (QOFs)

This program was established by the federal government in 2017 and designed to spur economic development in specific areas. If you reinvest your capital gains into a QOF operating in a designated Qualified Opportunity Zone (QOZ), you can defer paying taxes on those gains until you sell your investment, or until December 31, 2026 — whichever comes first. 

You must reinvest your capital gains within six months of selling your business. If you hold the investment for at least five years, you can exclude a portion of your original capital gains from taxation. If the investment is held for at least ten years, any capital gains from the future sale of the investment are returned to you tax-free.

Pros:

  • Defer taxes on QOF gains until Dec 31, 2026, or upon sale/exchange.
  • 10% gain exclusion for QOFs held over 5 years; 15% for over 7 years.
  • After 10 years, QOF investments can grow tax-free.
  • QOF investments boost distressed areas with new jobs and development.
  • Opportunity to make a positive impact in at-need communities.

Cons:

  • As with any investment, there’s no guarantee of a return, and investing in distressed areas may carry higher risks.
  • There are strict regulations to qualify for the tax benefits, including how and when funds are invested and managed.

4. Real Estate 1031 Exchange

If your business includes real estate, a 1031 exchange allows you to defer capital gains taxes by reinvesting the proceeds from the sale of your property into the purchase of another property. Also known as a “like-kind” exchange, the IRS lets you sell one property and reinvest the proceeds in another similar property while deferring taxes on your gain. 

With careful maneuvering, real estate investors can use 1031 exchanges to keep deferring taxes indefinitely through strategic property swapping.

Pros:

  • Defer capital gains taxes on the sale.
  • By deferring taxes, investors can potentially acquire larger or more valuable properties, allowing their portfolio to grow.
  • Properties exchanged through 1031 may be inherited with a stepped-up basis, negating capital gains tax.

Cons:

  • The rules governing 1031 exchanges are complex; failing to adhere to them can result in a significant tax liability.
  • Strict timing pressures quick decisions, risking less favorable choices.
  • Not all real estate transactions qualify for a 1031 exchange. 

5. Charitable Remainder Trust (CRT)

Feeling philanthropic? A CRT allows you to contribute a portion of your business sale proceeds to a trust, which then pays you (or another beneficiary) a stream of income for a term of years or for life. After the term ends, the remainder goes to your chosen charity. This strategy can offer immediate tax deductions and reduce estate taxes while supporting a cause close to your heart.

For example, let’s say you sold your business for $5 million and contributed $2 million in proceeds to a CRT. The CRT could then pay you a set percentage of $2 million yearly, say 5%, equaling $100,000 annually. After your death, the charity of your choice would receive the remaining assets in the CRT.

Pros:

  • Claim an immediate tax deduction in the year you set up the trust and transfer assets into it.
  • If the CRT is funded with appreciated assets, assets within the trust can be sold without incurring capital gains tax at the time of the sale. This allows the full value of the assets to be reinvested by the trust, potentially increasing the income generated for the beneficiaries.
  • CRTs provide an income stream for the beneficiaries. 
  • Beyond the financial benefits, you can support causes and organizations important to you.

Cons:

  • CRTs are irrevocable; beneficiaries or terms of the trust cannot be changed.
  • Setting up and managing a CRT can be complex, requiring legal and financial expertise.
  • Income received depends on the trust’s investment performance. Poor investment performance can reduce the income stream and the ultimate charitable donation.

Let Five Pine Wealth Help You With Tax-Deferral Strategies

Smart tax planning is crucial, and every situation is unique. It’s essential to carefully evaluate your options and seek professional advice before making any decisions.

Remember, navigating the complexities of tax law can be tricky. Five Pine Wealth Management has experienced advisors who can help you determine the best tax-deferral opportunities for your situation. To schedule a meeting, send an email or give us a call at 877.333.1015.

Selling your business is a considerable achievement and the start of a new chapter. Celebrate your success, explore your options, and make informed decisions to maximize the rewards of your entrepreneurial journey.

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April 22, 2026
Key Takeaways A portfolio designed for accumulation may carry too much risk, or the wrong kind of risk, once you stop contributing. When two spouses are at different financial life stages, their investment strategies should reflect that difference. A Roth conversion strategy during the years before required minimum distributions begin can meaningfully reduce your long-term tax burden. Rob spent 30 years building a picture-perfect financial foundation for his retirement. He maxed out his 401(k) and stayed disciplined through market downturns. By the time he retired from a long career in plant management and HR, he had a nest egg most people only dream about. But then retirement arrived, and with it came a new kind of anxiety. Rob spent all those years learning how to build wealth, but never how to draw it down. The accumulation phase was clear, but the decumulation phase is far more complex and far more personal. Rob had hired a financial advisor when he retired, hoping for guidance through that transition. Instead, he got portfolio management and investment decisions without the broader planning context he needed. That relationship didn’t last a year. And that’s when he and his wife Christie, came to Five Pine. The Numbers Behind the Plan: When They Started Today Rob’s age 57 63 Investable assets $1.1 million $2.5 million Net worth — $3.5 million Primary challenge No decumulation plan, Comprehensive plan in place heavy pre-tax exposure Key strategies Portfolio redesign, Ongoing tax planning, Roth conversion planning rebalancing When Saving Well Isn't Enough When we first met Rob and Christie, a few things stood out right away. Rob was recently retired with $1.1 million in investable assets (the vast majority of it in pre-tax retirement accounts). Christie, about ten years younger than Rob, was still working and earning a high income as a part-owner of a small business. They were a dual-financial-life household: one person winding down, one still in full accumulation mode. Rob’s most pressing concern was straightforward to state but harder to solve: how much could he spend without putting their retirement at risk? He wanted to travel, renovate the house, and buy a new vehicle without second-guessing himself. But after those decades of saving, spending felt foreign, even a little reckless. He had seriously considered going back to work, not because he needed to, but because he felt he couldn’t trust the numbers. Underneath that, a long-term tax problem was simmering. With most of their savings in pre-tax accounts, Rob and Christie were looking at significant required minimum distributions (RMDs) starting at age 73. And Christie, likely to outlive Rob by a meaningful margin, would eventually face those distributions as a single filer at higher tax rates. 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But in retirement and drawing from the portfolio regularly, it introduced more risk than his situation warranted. We restructured his holdings to roughly 60% equities, 25% fixed income, and 15% in alternative investments, specifically private credit funds and private real estate. The alternatives were a meaningful addition. They could potentially carry lower price fluctuation than publicly-traded assets and have the ability to generate distributions, which may potentially help support spending needs without forcing untimely equity sales. Christie's accounts, meanwhile, stayed aggressive. She's still contributing through her employer plan, still has years of earning ahead of her, and has time to weather market swings. Finally, we put a Roth conversion strategy in place for the years ahead. 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When markets dropped sharply during a period of economic uncertainty, we rebalanced, selling fixed income to buy equities at a discount. As markets recovered, those moves contributed meaningfully to their overall growth. Five years in, their investable assets have grown from $1.1 million to $2.5 million. Beyond that, Rob and Christie have referred five family members to Five Pine, a reflection of the trust that developed alongside their plan. In Christie's own words: "Ben and Jeremy are honest, approachable, and very professional. They take great pride in getting to know clients and listening to each individual's goals. Honestly, they are the best fiduciaries I have ever worked with, by far." Your Decumulation Strategy Starts Before You Retire Rob's story is more common than most people realize. Disciplined savers often arrive at retirement without a spending plan, a tax strategy, or a portfolio suited to this new phase of life. If you're within five to ten years of retirement (or already there), it's worth asking whether your current advisor is doing comprehensive planning, including tax planning for retirement, or simply managing your investments. Over the course of a long retirement, that distinction can determine whether or not you’re equipped to tackle retirement with confidence. We'd love to help you find your number. Email us at info@fivepinewealth.com or call 877.333.1015. Let's talk.* Frequently Asked Questions (FAQs) Q: When should I start building a decumulation strategy? A: Ideally, five to ten years before you plan to retire. That window gives you time to gradually reposition your portfolio, identify potential tax issues before they become expensive, and stress-test your spending assumptions while you still have income coming in. Q: What role does Social Security timing play in a decumulation plan? A: Claiming Social Security early locks in a permanently reduced benefit, while waiting until 70 can increase your monthly payout substantially. The right timing depends on your health, other income sources, and whether a spouse will eventually depend on your benefit as a survivor. Coordinating with your Roth conversion strategy is also worthwhile, since both affect your taxable income. Q: What happens to my decumulation plan if the market drops early in retirement? A: This is often called the sequence of returns risk. A significant market decline in the first few years of retirement can have a lasting impact on a portfolio, because you're withdrawing funds at lower values. A well-designed decumulation strategy accounts for this by maintaining a portion of the portfolio in less volatile assets, so you're not forced to sell equities at a discount to cover living expenses during a downturn. *Names have been changed to protect client privacy*
April 1, 2026
Key Takeaways Taking early withdrawals from your 457 while letting your IRA grow can help you build a more balanced retirement plan. First responders with LEOFF or PERSI pensions can use their 457 plan as a bridge between retirement and traditional retirement account access. Rolling your 457 into an IRA at retirement removes penalty-free access to funds before age 59½. Many first responders in Washington and Idaho can realistically retire early. Thanks to pensions like WA LEOFF Plan 2 or ID PERSI, disciplined savings, and a long career of service, retiring at 55 is common. If you've been putting money into a 457 deferred compensation plan, you may be sitting on a sizable balance by the time you retire. As retirement approaches, you may be wondering: “What do I do with my 457 deferred compensation plan?” Many people unintentionally make a costly mistake. They roll their entire 457 balance into an IRA the moment they retire, thinking it's the right move. It might seem logical to combine accounts and keep things simple by moving everything into one IRA. However, this move eliminates a key advantage of a 457 plan: you lose penalty-free access to your money before age 59½. Let’s look at how this works and how you can set up your retirement accounts to stay flexible in your early retirement years. Early Retirement at 55: The Income Gap Problem Whether you're covered by LEOFF Plan 2 or PERSI, retiring around age 55 is entirely realistic. LEOFF Plan 2 members can retire with a full benefit at age 53 (or as early as 50 with 20 years of service and a reduced benefit). Idaho PERSI first responders can retire as early as 50 under the Rule of 80. The years between ages 55 and 59½ are a unique financial period. Your pension might cover a portion of your income needs, but often not everything. Social Security usually starts much later, and if most of your retirement savings are in IRAs, taking out money early can trigger penalties. This is where your 457 plan can be especially helpful. Unlike most retirement accounts, 457 plans let you take out money without the 10% early withdrawal penalty once you separate from service. This rule gives you a helpful bridge between retiring and the time when traditional retirement accounts become easier to access. You lose this benefit if you move your money into an IRA too soon. If your pension doesn't cover all your needs and you rolled everything into an IRA, you might face penalties or be unable to access your money. This early-retirement gap is exactly what good 457 planning can help you avoid. 457 Plan Withdrawal Rules Once you separate from service, whether you quit, get laid off, or retire, you can start taking 457 withdrawals from your 457 plan without a 10% penalty, no matter your age. Whether you're 55, 45, or even 35, the penalty doesn't apply. If you move money from your 401(k) or another account into your 457 and then withdraw it, that money loses the 457's penalty-free status. It’s now treated like IRA money and is subject to the 10% early withdrawal penalty. Only the original 457 money stays penalty-free. You will still owe ordinary income taxes on every withdrawal from a traditional 457, just like an IRA. The key difference is that you don’t have to pay the extra 10% penalty, which can save you thousands of dollars. Should I Roll My 457 Into an IRA? Now that you know the withdrawal rules, you might be asking yourself, “Should I roll my 457 into an IRA?” This is an important question, and the answer is: it depends. Usually, moving everything at once isn’t the best idea. Many people roll their entire 457 into an IRA at retirement because it’s often suggested as a way to “consolidate” and “simplify.” While there are legitimate reasons to roll some money into an IRA, doing it all at once at age 55 means you lose your penalty-free income bridge. A few of the advantages of rolling some money into an IRA are: More investment options Estate planning flexibility Roth conversion strategies A better strategy for most first responders retiring around 55 is to split your 457 balance into two parts, or “buckets,” each with its own role in your retirement plan: Bucket 1: Use your 457 account for early-retirement cash flow. This is the money you'll live on from age 55 to 59½ (or whenever your pension plus other income is sufficient). The 457 allows penalty-free withdrawals at any time, so you control both the amount and timing of distributions. This bucket bridges the gap until your other income starts coming in. Bucket 2: Roll into an IRA for long-term growth. Once you've determined how much you need for the early years, the rest can be rolled into a traditional IRA. The IRA bucket offers more investment choices and greater flexibility for estate planning or Roth conversion. Here’s an example: Jason is a firefighter retiring at 55 from Washington with $300,000 in his 457. His LEOFF Plan 2 pension covers most of his expenses but leaves a $1,500 per month gap. Instead of rolling everything to an IRA, he keeps $90,000 in the 457, which covers about five years of that gap at $1,500/month, and rolls the remaining $210,000 into a traditional IRA. The $90,000 stays accessible, penalty-free, and the $210,000 continues to grow. By the time he turns 59½, the IRA restrictions are gone, and he hasn't paid any unnecessary penalties. Deferred Compensation Rollover: What You Need to Know If you decide to roll part of your 457 into an IRA, the process is simple. You can move your 457 into another retirement account, like a traditional IRA, Roth IRA, 401(k), 403(b), or another 457 plan. There are a few things to keep in mind: Direct rollover is the best option. Have your 457 plan send the money straight to your IRA provider. If you get the check yourself, you have 60 days to put it into your IRA, and your employer will withhold 20% for taxes. If you miss the 60-day deadline, it will be treated as a taxable withdrawal. Roth conversions are possible, but watch the tax hit. You can convert your 457 to a Roth IRA, but be careful about taxes. If you do this soon after retiring, your income might be lower, which could make it a good time for a Roth conversion. Just make sure not to convert everything at once without checking the tax impact. Putting IRA money back into your 457 is usually not a good idea. Once IRA or other retirement plan money goes into your 457, it loses the penalty-free withdrawal benefit. Only do this if you have a very specific reason. Washington's DCP and Idaho's PERSI Choice 401(k) have their own rules. Washington state's Deferred Compensation Program (DCP) is administered by the Department of Retirement Systems (DRS). Idaho first responders may have the PERSI Choice 401(k) as well as other 457 plans. Be sure you know which accounts you're dealing with before starting any rollovers. Here are two helpful resources: Washington DRS (DCP information) Idaho PERSI A Note on Taxes and Required Minimum Distributions Even if you don’t pay a penalty, you still need to think about taxes. Every dollar you take from a traditional 457 counts as regular income for that year. If you're not careful with how much you withdraw, you could end up in a higher tax bracket, especially if your pension income is already high. This is one reason the bucket approach is helpful: you can control how much you withdraw from your 457 each year and keep your taxable income in a comfortable range. It’s also important to know that required minimum distributions from traditional 457 accounts begin at age 73 or 75, depending on when you were born. Beginning in 2024, Roth 457(b) accounts in governmental plans became exempt from RMDs under the SECURE 2.0 Act. This is another reason to think about whether Roth contributions or conversions are right for you. Talk With Us Before Rolling Your 457 The 457 plan is a powerful tool, and rolling it into an IRA without careful thought means losing the feature that makes it so valuable for retirees. At Five Pine Wealth Management, we help many first responders and public employees in Washington and Idaho. We know the ins and outs of WA LEOFF Plan 2, Idaho PERSI, deferred compensation plans, and the unique challenges of retiring earlier than most people. If you're within 10 years of retirement, or if you're already retired and want to make sure your money is set up the right way, we'd be happy to help. Call us at 877.333.1015 or email info@fivepinewealth.com. Before making a decision about your 457 rollover, let’s make sure your retirement accounts are working together as they should be. Frequently Asked Questions (FAQs) Q: Does a 457 rollover to an IRA count as a taxable event? A: A direct rollover from a traditional 457 to a traditional IRA is not taxable. Q: Can I take money out of my 457 while I'm still working? A: Generally, no. 457 plans don't allow withdrawals while you're still employed, except for very limited exceptions (such as an unforeseeable emergency). The penalty-free access kicks in once you separate from service. Q: What happens to my 457 if I roll it into an IRA and then need money before age 59½?  A: You lose the 457's penalty-free protection. If you roll 457 funds into a traditional IRA, you lose the flexibility of penalty-free early withdrawals and become subject to a 10% early withdrawal penalty