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Supreme Court hears case on insurance and estate taxes

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In its second case this term involving tax policies affecting financial advisors’ clients, the Supreme Court will decide a complex question about life insurance and the value of an estate.

Connelly v. Internal Revenue Service reached arguments March 27 at the high court, where justices struggled to grasp the complications around the impact on the value of a company for purposes of the estate tax from life insurance proceeds tied to the death of a shareholder. 

The petitioner, Connelly, argued that the IRS should not include the proceeds of the redemption of a family-owned company’s policy on his brother’s life in their construction firm’s value because that insurance money immediately bought the remaining shares. The IRS collected additional tax of $889,914 from the deceased brother’s estate based on the agency’s view that the proceeds boosted the company’s value. Two lower courts ruled in favor of the IRS.

Most observers noticed skepticism among the justices for the business owner’s stance that the IRS overvalued the company, although many people would likely agree with Justice Brett Kavanaugh’s observation at the hearing that some concepts in the case are “extremely difficult.” The session came a few months after arguments in Moore v. U.S. about a provision of the 2017 Tax Cuts and Jobs Act in a case amounting to a major challenge to government taxing power

In theory, many tax experts could see how including the insurance proceeds in the company’s valuation “rises to the level of being unfair” to an estate when the policy requires them to be redeemed by purchasing the deceased family members’ shares, said Jose Reynoso, the head of personal financial planning and advance estate and tax for Citizens Private Wealth.

“It’s really interesting to us as planners and practitioners that the Supreme Court even took it up,” Reynoso said in an interview. “It’s a unique, sort of nichey thing that impacts not too many people.”

READ MORE: A tax on ‘unrealized’ income? A test for wealth laws at the Supreme Court

The issue does come up frequently for the owners of closely held businesses who purchase life insurance policies for their largest shareholders, he noted. The IRS valuation of the construction company “would destroy a valuable succession planning tool that the nation’s small businesses have openly used for decades,” the plaintiff’s attorney, Kannon Shanmugam, said at the hearing, according to the transcript

The U.S. Chamber of Commerce and the National Federation of Independent Business Small Business Legal Center submitted a brief in support of that position. Still, justices from both the conservative and liberal sides of the court kept asking Shanmugam about the effect on prospective buyers’ offers for the company from about $3 million in insurance proceeds flowing to the surviving brother, the SCOTUSblog reported.

Their apparent siding with the IRS and “tepid reception to the taxpayer estate” was not “entirely surprising” to Frank Paolini, partner with the private wealth services group at the Neal Gerber Eisenberg law firm. 

“While I could make arguments on either side of the case, the taxpayer estate must still contend with the logically glaring issue that a policy covering the life of a key shareholder would have an impact on the fair market value of the shares in any other context,” Paolini said in an email. 

“For instance, a hypothetical buyer of the company would ascribe additional value to the shares if the company held a policy on the life of key employees and shareholders,” he continued. “Just because the company must use the policy proceeds to pay the decedent’s family for the shares, the shares are still redeemed, and the value of the purchased equity is returned to the company on redemption,” he said.

“Essentially, the value of the shares must go somewhere when the decedent dies. In the end, the family receives the benefit of the payment from the policy and the company receives the shares back in return, which is presumably equal to the value of the shares purchased from the decedent’s estate. If the court held otherwise, it would seem incongruent with many other areas of estate tax valuation,” Paolini said.

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The plaintiffs held that the government was taking positions that are out of step with the fact that the surviving brother would still be subject to capital gains taxes and rulings in other cases that contradicted the use of the proceeds in a valuation. However, their argument revolved around the notion that “before you can value something, you must first subtract the price paid for the very thing you are trying to value,” U.S. Department of Justice Assistant to the Solicitor General Yaira Dubin told the court.

“A redemption obligation divides the corporate pie among existing shareholders without changing the value of their interests,” Dubin said. “And, here, the corporate pie was worth $6.86 million, not $3.86 million.” 

Just as in the Moore case, the Supreme Court took up a matter that could reap massive changes to clients’ tax bills, then displayed some reluctance toward such drastic shifts. Regardless, the justices again discussed topics that clients could raise with their advisors and other tax professionals and even touched on potential planning methods. 

Toward the end of the 54-minute hearing last month, Dubin spoke with the justices about how a cross-insurance agreement between the brothers or a trust structure could enable the taxpayers to avoid having the proceeds go into their corporation’s valuation. The Supreme Court will release decisions in the Moore and Connelly cases by the end of June or early July. 

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How the accounting profession is helping rebuild LA after wildfires

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The Los Angeles entertainment industry has long relied on highly skilled freelancers and independent contractors to power its film, television and musical entertainment projects. According to a Los Angeles County Economic Development Corp report, nearly 100,000 freelance professionals and other independent contractors — more than one-third of the total workforce of one of LA’s largest industries — are non-salaried, non-full-time workers. 

Even before the wildfires, employment in California’s film, television and sound sector had dropped nearly 30% between 2022 and 2024, according to Otis College of Art and Design research. Researchers attributed that slump to a combination of COVID, two devastating strikes and the bursting of the streaming bubble. According to FilmLA , filming days in LA County last year were the second lowest on record

Gig workers in LA’s entertainment industry already operate in a volatile environment where job security is almost nonexistent, and their income is heavily project dependent. The wildfires compounded an already tough situation — many lost their homes, their workplaces and the infrastructure they rely on to find gigs. Unlike full-time employees, gig economy workers don’t have benefits, severance packages or unemployment safety nets to fall back on. And when production suddenly halts, there are no guarantees about when or if their work will resume. This leaves tens of thousands of workers scrambling to make ends meet. This situation has hit close to home. My brother is a choreographer/dancer who also has a talent agency. When the fires canceled a performance, it cost him (and his clients) a five-figure job. That job would have been his biggest deal yet, and it all went away so suddenly.

The fires came after the pandemic shut down movie theaters and production five years ago. Then came the 2023 writers and actors strikes, which halted projects, delayed film releases and cut into box office revenue. As a result, studios cut back spending, leading to massive layoffs while streamers reevaluated content strategies and projects were scrapped. 

Now, the wildfires have added another layer of devastation, displacing thousands of workers and destroying homes, sets and production facilities. Hollywood hasn’t had a chance to catch its breath, and the ripple effect of these disruptions is massive.

Losing a home is more than just losing a roof over your head — it also means you lose stability, security, and in many cases, the tools you need to work. For actors, directors and producers, it might mean losing scripts, gear or a home office where they edit, write or produce. For below-the-line workers — crew members, sound engineers, set designers — losing your home could mean losing equipment, props or even an entire workshop. In an industry where many workers are freelancers or small business owners, rebuilding isn’t as simple as filing an insurance claim. It’s a financial and emotional blow that can take years to recover from, all while trying to find work in an already struggling industry.

Accounting profession steps up to help

I’m proud to report that two organizations you wouldn’t normally associate with the LA entertainment industry are taking the lead in the region’s disaster recovery efforts.

The National Association of Black Accountants is focused on financial recovery and stability, especially for displaced workers and for small business owners in the entertainment industry. As NABA’s LA Chapter President, I can assure you we’re working to provide financial literacy resources, guidance on navigating relief funds and direct support for impacted workers through our network of professionals. Whether it’s helping with the tax implications of disaster relief funds, advising on business continuity plans, or connecting affected workers to financial assistance programs, NABA is committed to ensuring that those impacted aren’t left behind as LA rebuilds. NABA has started a Disaster Information Hub where individuals can find disaster resources and instructional webinars.

Meanwhile, I continue my involvement with the California Society of CPAs, which has a benevolent fund. Through that fund, CalCPA is offering direct financial assistance to CPAs and finance professionals who have been impacted by the wildfires. CalCPA also provides pro bono financial consulting to gig workers, small business owners and independent contractors in entertainment — helping them understand their options, apply for relief and develop recovery strategies. The goal is to make sure people have access to financial professionals who can guide them through this tough time. Here are some Disaster Recovery resources from CalCPA. 

Entertainment is the heartbeat of LA. It’s more than just an industry; it’s a culture, a community and an economic powerhouse. I’ve worked closely with “creatives,” content creators and production teams, and I’ve seen firsthand how much passion and dedication goes into the amazing work they do. But I’ve also seen how financially vulnerable many of these workers are, especially gig workers who don’t have a safety net when disaster strikes. Providing financial stability to these talented, “essential” workers is a key part of rebuilding LA — not just for individuals, but for the entire industry.

10 ways you can help

1. Donate to local relief funds

  • Organizations like the Entertainment Community Fund, the California Fire Foundation, and Red Cross LA provide immediate assistance to those displaced or affected.
  • Consider donating directly to union-supported initiatives like SAG-AFTRA Disaster Relief Fund or the IATSE Local 600 Hardship Fund.

2. Support impacted businesses

  • Many small studios, rental houses and creative vendors lose revenue during wildfires. Seek out and support these businesses once they reopen — from indie theaters to prop houses to local production crews.

3. Share resources

  • Use your platform to amplify verified relief efforts, fundraisers or mutual aid lists. Especially in the entertainment industry, visibility helps drive action.

4. Volunteer (if you’re local)

  • Join community cleanup efforts, deliver meals or offer temporary housing support via platforms like Airbnb’s emergency housing program.

5. Offer pro bono financial services

  • Entertainment professionals, especially freelancers, are often unprepared for the financial chaos caused by sudden work stoppages or evacuation.
  • CPAs and financial advisors can volunteer their time to help affected workers apply for emergency assistance, file insurance claims or restructure debt.

6. Help production companies and studios navigate business interruption insurance

  • These employers may be eligible for insurance payouts due to delays or cancellations. Financial pros can provide vital guidance with organizing claims and documenting losses.

7. Assist nonprofits with emergency budgeting

  • Many nonprofit arts organizations will be hit hard by fire-related shutdowns. Accountants can assist with cash flow forecasting, grant applications or budget adjustments to help them stay afloat.

8. Host financial literacy webinars for affected creatives

  • Partner with guilds, unions or community centers to offer freelancers workshops about managing disaster-related disruptions, taxes and rebuilding savings.

9. Advocate for disaster-resilient policies

  • Use your professional voice to push for better financial safety nets in the entertainment industry. These include income protection, disaster savings accounts, or revised insurance policies for independent creators.

10. Get involved

Consider joining the California Society of CPAs and the National Association of Black Accountants. Ask about NABA’s Disaster Information Hub and CalCPA’s Disaster Recovery resources.

If we want Hollywood and LA’s creative scene to come back stronger, we need to support the people who make it all happen. That’s where you come in. There are so many ways you can help.

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No AI disclosure rules doesn’t mean no AI disclosures at all

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Though the Securities and Exchange Commission has yet to issue regulations specific to AI, this doesn’t mean companies are off the hook when it comes to disclosures, as the technology’s use can easily be slotted into other, already existing requirements. 

Speaking today at a virtual conference hosted by Financial Executives International, Scott Lesmes, partner in charge of public company advisory and governance with law firm Morrison Foerster, noted that there are many risks that come with AI including false or misleading information, data breaches, cyberattacks, intellectual property risk and much more. He said people need to be taking these risks seriously.

“These mistakes are in the real world and have had significant consequences,” he said. 

He pointed to a case where a chatbot advised small business owners that it was legal to fire people for complaining about sexual harassment, which is absolutely is no. He also referred to another case where a real estate company was forced to take a $300 million writeoff for relying on a faulty AI algorithm for property pricing decisions, and another where an AI model used by hospitals to determine which patients are high risk and need extra care was found to be biased against Black people, as it was far less likely to identify them. 

Incidents like this underscore the need for robust AI governance. He noted that there has been a rise in companies forming cross-disciplinary AI governance committees encompassing finance, legal, product, cybersecurity, compliance and in some cases HR and marketing; failing that, he has also seen companies add AI oversight on the duties of existing committees. While some companies have established dedicated AI departments, more commonly they have been giving AI oversight duties to the Chief Information Security Officer or other relevant c-suite position. 

He also noted that there has been a dramatic increase in board supervision of AI, saying that in the most recent 10-K season there was a lot of clients who added “Oversight of AI” in terms of what the board was responsible for; while it was a small percentage, he was certain it was going to increase over time. He has also found that many boards either designate a single AI expert who handles such matters or place the responsibility on either already-existing technology committees or (more commonly) audit committees. 

“There is certainly a tension, audit committees already have such a full plate, so adding another responsibility, especially with such a broad mandate, can be a little unsettling but that is where many companies are putting this, if they handle it on the board level. Audit committee does make some sense, because it is very focused on internal controls as well as compliance,” he said. 

Boards generally need to consider the legal and regulatory factors that may impact operations, and just like how many have management frameworks for oversight, so too should there be AI frameworks for how the board fulfills these responsibilities. In executing these duties, boards needs to understand the critical AI uses and risks in the company, how they integrate with business processes, what is the nature of the AI system, how does the company mitigate risk, how oversight responsibility is divided between board and management, as well as any material AI incidents. 

“The board does not need to know about every AI incident altogether, there needs to be a level of understanding of what’s important enough to share and what’s not. The board should understand the material incidents, how the company responded and the material impact,” he said. 

SEC Disclosures

Ryan Adams, another Morrison Foerster partner in the same practice area, noted that even though regulators like the Securities and Exchange Commission have yet to issue specific rules or guidance around AI, they have stressed the importance of complying with existing obligations, which may or may include disclosures regarding the company’s use of AI and its impact, particularly where it concerns business operations. Already companies need to report material risks and changes in their filings, and as AI further embeds itself into the global economy, it will almost certainly be a factor. 

Further, companies should not be making false claims or misleading potential investors in general, and this applies to AI as well. He noted that the government has been especially interested in “AI washing,” that is exaggerating, or making false claims about the company’s AI capabilities or use. He pointed to one example where the SEC brought charges against the CEO and founder of a startup who said they had a proprietary AI system that could help clients find job candidates from diverse backgrounds, but this AI did not in fact exist. He pointed out that this didn’t even involve a public company, just a private one that was trying to raise investment capital. 

“So it makes clear that the SEC will scrutinize all AI-related claims made by any company, public or private, trying to get investors to raise capital,” he said. 

He added that AI washing can be thought of very similarly to inflating financial results or just making up the numbers entirely. Also, just as an entity should not overstate the capacities of their AI systems, the same has already applied for automation technology in general. Regulators want clear and candid disclosures about how a company uses AI and how it presents material risks. In this regard, he also warned against generic or boilerplate disclosures regarding AI. 

“Regardless of the type of company you are, you have to take this seriously. Anyone touting the benefits of AI with customers or the public needs to make sure what they say is truthful and accurate and can be substantiated, or risk potential legal consequences,” he said. 

It is important to keep materiality in mind. Neither investors nor regulators want to read a list of every conceivable AI-related risk a company faces when only one or two are relevant. He conceded that this might require slightly different thinking, as accountants tend to lean on quantitative factors to assess materiality, but AI can also carry qualitatively material factors as well. There is the risk that AI could inadvertently breach confidentiality agreements through sensitive information in the training data, it could completely disrupt traditional business functions if used properly or completely disrupt new ones if used improperly, there is the risk of being unable to find the experts needed to properly monitor an AI system, there could be third party fees for things like data storage or increased energy use, AI can disrupt competitive dynamics in the market, there could be ethical risk like the aforementioned racist algorithm, and legal or regulatory risks. 

“You could go on forever with these AI risks…  Just because you use AI and a risk is potential does not necessarily mean disclosure is appropriate. You need to spend time thinking about whether AI-related risks are appropriate to disclose and if they are they should be narrowly tailored to describe the material risk,” he said. 

When assessing materiality, he said to go with the same standard accountants have been using for ages: is there a substantial likelihood a reasonable investor would consider this information important to determine whether to buy, sell or hold a security. Where AI introduces a slight wrinkle is that, given the pace of change in the field, it is important for companies to review and reevaluate their risk factors every quarter. 

But risks are not the only thing one should disclose. Adams noted that companies should also consider AI impacts when drafting management discussion and analysis or the executive overview, painting out major developments or initiatives or milestones related to the technology. AI could also come up in discussions of capital expenditures, if the entity made big AI investments that are material and known to the business, that needs to be disclosed. Another area AI plays into is cybersecurity disclosures, which already has a number of SEC requirements around it. The two topics, he said, often go hand in hand, so if AI interacts with cybersecurity in any way it might be worth disclosing. 

Overall, Adams recommended companies fully and accurately disclose their AI use; avoid overly vague or generic language given AI’s wide variations; avoid exaggerated claims around what your AI is capable of doing, taking care especially not to discuss capacities in terms of hypotheticals; be specific about the nature and extent of how the entity is using AI and the role AI plays in business operations; have a good understanding of vendors and other third parties who use AI, as their risks could ripple outwards; establish, or at least begin to establish, an AI governance framework; train the staff in AI so they can understand what it can and cannot do; actively monitor company AI usage; regularly update stakeholders on changes, progress and improvements in company AI use; and have either the legal department or outside counsel review any public statements or marketing materials mentioning AI. 

While the current administration has emphasized a less regulated approach to AI, Adams noted that the SEC is still active in its dialogues with the business community around potential regulation, mentioning a recent meeting with the investment advisor community as well as a strategy roundtable with the financial services community. 

“The big takeaway here is that both the SEC and industry are saying ‘we want to have active and ongoing communications as this develops’ … any regulations we do see, if any, in the future [will be] informed by what is actually happening in the marketplace,” he said.

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House passes plan to advance Trump tax cuts, debt limit boost

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President Donald Trump’s drive to enact trillions of dollars in tax cuts and raise the federal debt is on track after he and congressional leaders successfully corralled House Republican lawmakers to approve a Senate-passed budget outline.

The 216-214 vote Thursday on the budget — which outlines the parameters for the tax cut and debt ceiling increase — was delayed a day so Trump and Republican congressional leaders could assuage a dissident group of conservative spending hawks pressing for deeper cuts in safety-net programs. 

The president worked the holdouts by phone and in a White House meeting. House Speaker Mike Johnson held a press conference to declare himself “committed” to coming up with at least $1.5 trillion in spending cuts. And Senate Republican leader John Thune joined the speaker to announce “a lot of” Republican senators shared the goal, though he stopped short of a commitment. 

It was enough. 

With the budget approved, the way is open for a follow-on package to cut taxes by up to $5.3 trillion over a decade and raise the debt ceiling by $5 trillion, in exchange for $4 billion in spending cuts. Republicans can now pass Trump’s tax-cut agenda solely on GOP votes, bypassing the need for negotiations with Democrats.

Trump offered congressional Republicans “Congratulations” in a social media post minutes after the vote.

The vote came a day after Trump announced a 90-day pause on some of his sweeping tariff plans that have roiled markets and sparked predictions of a looming recession. Financial markets — often a barometer of success for the president — initially soared on the news, though U.S. stocks retreated Thursday morning amid angst over an escalating trade conflict with China.

Republicans are planning to renew Trump’s first-term tax cuts for households and the owners of privately held businesses, and enact a fresh round of reductions, including expanding the state and local tax deduction and eliminating levies on tipped wages.

Conservative hardliners in the House say they want a final package to trim $2 trillion in spending over the next decade, a significant increase over the $4 billion the Senate is directed to cut in the budget passed Saturday. To make those reductions they’ll likely need to curb Medicaid, food stamps and other social programs with tens of millions of beneficiaries. 

A group of moderate Republicans sought — and gained — assurances from Johnson during the vote that the final bill would not cut benefits for qualified Medicaid individuals and institutions, said New Jersey Republican Jeff Van Drew. 

“We voted late to make the point,” Van Drew said. 

The group, however, is open to eligibility reviews and work requirements for Medicaid recipients, he said. 

The budget outline punts many of the hard decisions for lawmakers to hammer out later in the tax-cut negotiations. That could lead to a standoff with the Senate at the end of the process, where several members are resistant to large cuts in safety-net programs. 

Democrats assailed the plan as cutting benefits for the poor in order to pay for a tax cut skewed toward the wealthy. 

“Republicans do nothing to lower the high cost of living,” Democratic Leader Hakeem Jeffries said on the House floor. “In fact, you’re making the affordability crisis in America worse, not better, when you target earned benefits and things that are important to the American people, like Medicaid.”

Senator John Barrasso, the No. 2 Senate Republican, said GOP lawmakers in both chambers are committed to “very serious savings for the American taxpayer.”

Trump hosted Republican holdouts at the White House on Tuesday to urge their backing. He echoed his pleas while speaking later that day at a donor event in Washington, imploring members who were hesitant to vote for the budget to “just get the damn thing done and stop showboating.”

“It is IMPERATIVE that Republicans in the House pass the Tax Cut Bill, NOW! Our Country Will Boom!!!” Trump posted on Truth Social Wednesday.

Johnson has set a target of the end of May to enact the tax bill, while Senate Republicans have talked of being able to complete the process by August. The 2017 tax cuts don’t expire until the end of the year.

Those self-imposed deadlines could be overrun by a fiscal deadline: the debt ceiling. 

The nonpartisan Congressional Budget Office estimates that the Treasury will be unable to pay all of its bills in August or September, but that date could come as soon as late May if tax receipts are low. 

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