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Navigating ownership transitions for private company financial leaders

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As record numbers of boomers reach retirement age, more private companies than ever must wrestle with transition challenges. 

Seven out of 10 business owners aged 50-plus will transition out of their businesses within the next decade, according to data from the Exit Planning Institute. Meanwhile, the U.S. Small Business Administration estimates that 10 million boomer-owned businesses will change hands between 2019 and 2029. This “Silver Tsunami” means private companies are grappling like never before with the complexities of ensuring continuity in leadership and operations. Against this backdrop, chief financial officers will assume a pivotal role in orchestrating strategies that safeguard the future viability and prosperity of their organizations. 

Transition planning is inherently multidisciplinary. Private company CFOs must navigate complex financial structures, assess risk factors and collaborate with legal and HR teams to ensure a seamless transition process. That’s more easily said than done. CFOs must have a blend of financial acumen and interpersonal skills to navigate the intricacies of an ownership transfer smoothly. 

For private company CFOs, controllers and senior managers, their plate is full these days. But, without having a clear roadmap for ownership transfer, they could face a succession crisis, leadership gaps and potential legal disputes. Moreover, the lack of a structured transition plan can erode stakeholder trust, diminish employee morale and jeopardize customer relationships. Ultimately, failing to plan for an ownership transition can result in irreparable damage to their company’s reputation and financial standing.

Getting started on the path to transition planning

The first crucial step in business transition planning is to identify key stakeholders and to clarify long-term objectives. Stakeholders may include owners, family members, employees, investors and external advisors. Understanding and communicating their perspectives, concerns and aspirations is essential for crafting a transition plan that aligns with the company’s goals and values. 

A thorough assessment of the current business structure and ownership structure is imperative for effective transition planning. At a minimum, CFOs should evaluate legal entities, ownership percentages, governance structures and operational frameworks. Identifying potential challenges, such as complex ownership arrangements or outdated governance practices, enables a company’s senior financial leaders to devise strategies to streamline the transition process. Additionally, assessing the company’s financial health and market position provides valuable insights for shaping the transition plan.

Setting clear and measurable goals, along with realistic timelines, is essential for driving the transition planning process forward. These goals may include succession objectives, financial targets, operational milestones and strategic initiatives. Establishing achievable timelines helps ensure accountability and progress throughout the transition journey. By breaking down the transition plan into actionable steps with defined deadlines, CFOs can maintain momentum and mitigate delays or setbacks.

Four transition options

Exploring ownership transfer options is a critical aspect of business transition planning. Here are four viable options for private companies to consider:

1. Family succession: Family succession involves transferring ownership and leadership of the business to family members, typically to the next generation. This option preserves the legacy of the company while keeping it within the family’s control. However, family succession can present challenges related to family dynamics, succession readiness and inequitable distribution of company ownership among family members. 

2. Management buyout: An MBO allows the existing management team or group of managers to purchase an ownership stake in the company. This option provides continuity in leadership and allows experienced managers to take ownership and responsibility for your company’s future. MBOs can be attractive for companies that have capable management teams seeking to retain control and continuity while providing liquidity for exiting owners. 

3. Employee stock ownership plan: An ESOP involves the establishment of a trust to purchase company shares on behalf of employees. Through ESOPs, employees gradually acquire ownership stakes in the firm, aligning their interests with the company’s long-term success. ESOPs can enhance employee engagement, retention and productivity while providing a tax-efficient mechanism for ownership transition. 

4. Selling to a third party: Selling the business to a third party, such as a strategic buyer, private equity firm or other outside investor, is a common ownership transfer option for private companies. This option offers liquidity for owners and may provide opportunities for business expansion, access to new markets or strategic partnerships. However, a third-party sale can greatly alter company culture, operations and strategic direction so it requires careful consideration of your company’s values and goals.

No matter which transition option CFOs choose, they must pay close attention to the business valuation and tax implications of the transaction.

Valuation and tax implications 

Conducting a comprehensive valuation of the business is essential for determining its fair market value and for facilitating informed decision-making during an ownership transition. Valuation methods may include asset-based approaches, income-based approaches or market-based approaches. As a senior member of a company’s financial team, CFOs have a thorough understanding of the organization’s financial performance, assets and liabilities. But do they know how to incorporate those metrics and proper market data to do a fair market value analysis? This is where engaging an independent business valuation professional can help them get an objective, independent assessment of your company’s true worth. 

Valuation is a highly subjective field and requires three key attributes: 1. Sound methodology and logic;2. Data, data and more data;3. Ability to utilize multiple methodologies. Each of the attributes above involves accounting, financial, economic and legal considerations. While most senior leaders possess some of this expertise, very few can translate that knowledge into an accurate appraisal. Common mistakes include conflating enterprise value and equity value, or using an overly simple methodology that doesn’t accurately reflect the company’s worth. Another common misstep is using outdated or irrelevant market multiples (often from a previous transaction in which they were tangentially involved). Further, most private company financial leaders are unaware of how certain factors affect the value of partial equity interests (i.e. less than 100%). 

Without having a qualified appraiser to guide your team, the company and its owners could be exposed to the following risks:

1. Receiving more (or less) than fair market value;
2. Understating or overstating taxable income for the entity or its owners;
3. Not meeting adequate disclosure requirements for a gift tax return and creating a permanent audit risk;
4. Creating cash flow issues for the entity or its owners.

An independent valuation professional should be able to analyze the subject company, make comparisons to industry benchmarks, incorporate economic or industry factors and provide multiple valuation methods rooted in real-time market data. They should also address interest-specific issues such as differences in distribution preferences and discounts for lack of control and marketability, and document all of their work in a detailed report that meets professional standards and reporting requirements. 

Example

One company we work with has an aging CEO/owner who is ready to turn over the reins to his capable adult son. They put together a transition plan with their former CPA and attorney which included elevated pay and salary continuation for dad as part of his buyout. As we started to review the plan, several red flags jumped out at us:

1. No actual equity got moved, so no transition was accomplished.
2. Dad got taxed at ordinary rates rather than at lower cap gain rates (and didn’t use the basis in his shares to reduce the gain).
3. We couldn’t unwind the old transaction and 409A deductions were taken — something the IRS frowns upon.

While the faulty transition plan could not be completely rectified, we were able to salvage it by gifting the equity to match what should have been part of the original deal in a stock purchase agreement. However, the company suffered in three important ways:

1. It lost the ability to use that basis and a higher tax rate for dad.
2. The gift tax could not be avoided on the gift.
3. It incurred significant additional legal, consulting and compliance expenses.

Tax planning plays a crucial role in minimizing tax liabilities associated with ownership transition and maximizing after-tax proceeds for all parties involved. The finance team should collaborate with tax advisors to devise tax-efficient strategies tailored to the specific circumstances of the transition. This may include structuring the transaction to leverage tax benefits, utilizing available exemptions or credits, and implementing estate planning techniques to optimize tax outcomes for owners and stakeholders. Doing homework on the valuation side can save lots of time and money on the tax-planning side down the road.  

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AICPA wants Congress to change tax bill

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The American Institute of CPAs is asking leaders of the Senate Finance Committee and the House Ways and Means Committee to make changes in the wide-ranging tax and spending legislation that was passed in the House last week and is now in the Senate, especially provisions that have a significant impact on accounting firms and tax professionals.

In a letter Thursday, the AICPA outlined its concerns about changes in the deductibility of state and local taxes pass-through entities such as accounting and law firms that fit the definition of “specified service trades or businesses.” The AICPA urged CPAs to contact lawmakers ahead of passage of the bill in the House and spoke out earlier about concerns to changes to the deductibility of state and local taxes for pass-through entities. 

“While we support portions of the legislation, we do have significant concerns regarding several provisions in the bill, including one which threatens to severely limit the deductibility of state and local tax (SALT) by certain businesses,” wrote AICPA Tax Executive Committee chair Cheri Freeh in the letter. “This outcome is contrary to the intentions of the One Big Beautiful Bill Act, which is to strengthen small businesses and enhance small business relief.”

The AICPA urged lawmakers to retain entity-level deductibility of state and local taxes for all pass-through entities, strike the contingency fee provision, allow excess business loss carryforwards to offset business and nonbusiness income, and retain the deductibility of state and local taxes for all pass-through entities.

The proposal goes beyond accounting firms. According to the IRS, “an SSTB is a trade or business involving the performance of services in the fields of health, law, accounting, actuarial science, performing arts, consulting, athletics, financial services, investing and investment management, trading or dealing in certain assets, or any trade or business where the principal asset is the reputation or skill of one or more of its employees or owners.”

The AICPA argued that SSTBs would be unfairly economically disadvantaged simply by existing as a certain type of business and the parity gap among SSTBs and non-SSTBs and C corporations would widen.

Under current tax law (and before the passage of the Tax Cuts and Jobs Act of 2017), it noted, C corporations could deduct SALT in determining their federal taxable income. Prior to the TCJA, owners of PTEs (and sole proprietorships that itemized deductions) were also allowed to deduct SALT on income earned by the PTE (or sole proprietorship). 

“However, the TCJA placed a limitation on the individual SALT deduction,” Freeh wrote. “In response, 36 states (of the 41 that have a state income tax) enacted or proposed various approaches to mitigate the individual SALT limitation by shifting the SALT liability on PTE income from the owner to the PTE. This approach restored parity among businesses and was approved by the IRS through Notice 2020-75, by allowing PTEs to deduct PTE taxes paid to domestic jurisdictions in computing the entity’s federal non-separately stated income or loss. Under this approved approach, the PTE tax does not count against partners’/owners’ individual federal SALT deduction limit. Rather, the PTE pays the SALT, and the partners/owners fully deduct the amount of their distributive share of the state taxes paid by the PTE for federal income tax purposes.”

The AICPA pointed out that C corporations enjoy a number of advantages, including an unlimited SALT deduction, a 21% corporate tax rate, a lower tax rate on dividends for owners, and the ability for owners to defer income. 

“However, many SSTBs are restricted from organizing as a C corporation, leaving them with no option to escape the harsh results of the SSTB distinction and limiting their SALT deduction,” said the letter. “In addition, non-SSTBs are entitled to an unfettered qualified business income (QBI) deduction under Internal Revenue Code section 199A, while SSTBs are subject to harsh limitations on their ability to claim a QBI deduction.”

The AICPA also believes the bill would add significant complexity and uncertainty for all pass-through entities, which would be required to perform complex calculations and analysis to determine if they are eligible for any SALT deduction. “To determine eligibility for state and local income taxes, non-SSTBs would need to perform a gross receipts calculation,” said the letter. “To determine eligibility for all other state and local taxes, pass-through entities would need to determine eligibility under the substitute payments provision (another complex set of calculations). Our laws should not discourage the formation of critical service-based businesses and, therefore, disincentivize professionals from entering such trades and businesses. Therefore, we urge Congress to allow all business entities, including SSTBs, to deduct state and local taxes paid or accrued in carrying on a trade or business.”

Tax professionals have been hearing about the problem from the Institute’s outreach campaign. 

“The AICPA was making some noise about that provision and encouraging some grassroots lobbying in the industry around that provision, given its impact on accounting firms,” said Jess LeDonne, director of tax technical at the Bonadio Group. “It did survive on the House side. It is still in there, specifically meaning the nonqualifying businesses, including SSTBs. I will wait and see if some of those efforts from industry leaders in the AICPA maybe move the needle on the Senate side.”

Contingency fees

The AICPA also objects to another provision in the bill involving contingency fees affecting the tax profession. It would allow contingency fee arrangements for all tax preparation activities, including those involving the submission of an original tax return. 

“The preparation of an original return on a contingent fee basis could be an incentive to prepare questionable returns, which would result in an open invitation to unscrupulous tax preparers to engage in fraudulent preparation activities that takes advantage of both the U.S. tax system and taxpayers,” said the AICPA. “Unknowing taxpayers would ultimately bear the cost of these fee arrangements, since they will have remitted the fee to the preparer, long before an assessment is made upon the examination of the return.”

The AICPA pointed out that contingent fee arrangements were associated with many of the abuses in the Employee Retention Credit program, in both original and amended return filings.

“Allowing contingent fee arrangements to be used in the preparation of the annual original income tax returns is an open invitation to abuse the tax system and leaves the IRS unable to sufficiently address this problem,” said the letter. “Congress should strike the contingent fee provision from the tax bill. If Congress wants to include the provision on contingency fees, we recommend that Congress provide that where contingent fees are permitted for amended returns and claims for refund, a paid return preparer is required to disclose that the return or claim is prepared under a contingent fee agreement. Disclosure of a contingent fee arrangement deters potential abuse, helps ensure the integrity of the tax preparation process, and ensures compliance with regulatory and ethical standards.”

Business loss carryforwards

The AICPA also called for allowing excess business loss carryforwards to offset business and nonbusiness income. It noted that the One Big Beautiful Bill Act amends Section 461(l)(2) of the Tax Code to provide that any excess business loss carries over as an excess business loss, rather than a net operating loss. 

“This amendment would effectively provide for a permanent disallowance of any business losses unless or until the taxpayer has other business income,” said letter. “For example, a taxpayer that sells a business and recognizes a large ordinary loss in that year would be limited in each carryover year indefinitely, during which time the taxpayer is unlikely to have any additional business income. The bill should be amended to remove this provision and to retain the treatment of excess business loss carryforwards under current law, which is that the excess business loss carries over as a net operating loss (at which point it is no longer subject to section 461(l) in the carryforward year).

AICPA supports provisions

The AICPA added that it supported a number of provisions in the bill, despite those concerns. The provisions it supports and has advocated for in the past include 

• Allow Section 529 plan funds to be used for post-secondary credential expenses;
• Provide tax relief for individuals and businesses affected by natural disasters, albeit not
permanent;
• Make permanent the QBI deduction, increase the QBI deduction percentage, and expand the QBI deduction limit phase-in range;
• Create new Section 174A for expensing of domestic research and experimental expenditures and suspend required capitalization of such expenditures;
• Retain the current increased individual Alternative Minimum Tax exemption amounts;
• Preserve the cash method of accounting for tax purposes;
• Increase the Form 1099-K reporting threshold for third-party payment platforms;
• Make permanent the paid family leave tax credit;
• Make permanent extensions of international tax rates for foreign-derived intangible income, base erosion and anti-abuse tax, and global intangible low-taxed income;
• Exclude from GILTI certain income derived from services performed in the Virgin
Islands;
• Provide greater certainty and clarity via permanent tax provisions, rather than sunset
tax provisions.

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On the move: HHM promotes former intern to partner

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KPMG anoints next management committee; Ryan forms Tariff Task Force; and more news from across the profession.

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Mid-year moves: Why placed-in-service dates matter more than ever for cost segregation planning

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In the world of depreciation planning, one small timing detail continues to fly under the radar — and it’s costing taxpayers serious money.

Most people fixate on what a property costs or how much they can write off. But the placed-in-service date — when the IRS considers a property ready and available for use — plays a crucial role in determining bonus depreciation eligibility for cost segregation studies.

And as bonus depreciation continues to phase out (or possibly bounce back), that timing has never been more important.

Why placed-in-service timing gets overlooked

The IRS defines “placed in service” as the moment a property is ready and available for its intended use.

For rentals, that means:

  • It’s available for move-in, and,
  • It’s listed or actively being shown.

But in practice, this definition gets misapplied. Some real estate owners assume the closing date is enough. Others delay listing the property until after the new year, missing key depreciation opportunities.

And that gap between intent and readiness? That’s where deductions quietly slip away.

Bonus depreciation: The clock is ticking

Under current law, bonus depreciation is tapering fast:

  • 2024: 60%
  • 2025: 40%
  • 2026: 20%
  • 2027: 0%

The difference between a property placed in service on December 31 versus January 2 can translate into tens of thousands in immediate deductions.

And just to make things more interesting — on May 9, the House Ways and Means Committee released a draft bill that would reinstate 100% bonus depreciation retroactive to Jan. 20, 2025. (The bill was passed last week by the House as part of the One Big Beautiful Bill and is now with the Senate.)

The result? Accountants now have to think in two timelines:

  • What the current rules say;
  • What Congress might say a few months from now.

It’s a tricky season to navigate — but also one where proactive advice carries real weight.

Typical scenarios where timing matters

Placed-in-service missteps don’t always show up on a tax return — but they quietly erode what could’ve been better results. Some common examples:

  • End-of-year closings where the property isn’t listed or rent-ready until January.
  • Short-term rentals delayed by renovation punch lists or permitting hang-ups.
  • Commercial buildings waiting on tenant improvements before becoming operational.

Each of these cases may involve a difference of just a few days — but that’s enough to miss a year’s bonus depreciation percentage.

Planning moves for the second half of the year

As Q3 and Q4 approach, here are a few moves worth making:

  • Confirm the service-readiness timeline with clients acquiring property in the second half of the year.
  • Educate on what “in service” really means — closing isn’t enough.
  • Create a checklist for documentation: utilities on, photos of rent-ready condition, listings or lease activity.
  • Track bonus depreciation eligibility relative to current and potential legislative shifts.

For properties acquired late in the year, encourage clients to fast-track final steps. The tax impact of being placed in service by December 31 versus January 2 is larger than most realize.

If the window closes, there’s still value

Even if a property misses bonus depreciation, cost segregation still creates long-term savings — especially for high-income earners.

Partial-year depreciation still applies, and in some cases, Form 3115 can allow for catch-up depreciation in future years. The strategy may shift, but the opportunity doesn’t disappear.

Placed-in-service dates don’t usually show up on investor spreadsheets. But they’re one of the most controllable levers in maximizing tax savings. For CPAs and advisors, helping clients navigate that timing correctly can deliver outsized results.

Because at the end of the day, smart tax planning isn’t just about what you buy — it’s about when you put it to work.

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