Accounting
Supreme Court hears case on insurance and estate taxes
In its second case this term
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
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
“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.”
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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,
The U.S. Chamber of Commerce and the National Federation of Independent Business Small Business Legal Center
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
“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.”
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.
Millions more taxpayers will be receiving the Form 1099-K in the mail this year for the first time if they were paid $5,000 or more last year through a service such as Venmo, PayPal, Cash App, StubHub, Etsy and Airbnb, and most won’t be expecting it.
New research from tax automation provider Avalara found 61% of gig economy workers are unaware of recently lowered 1099-K reporting thresholds aimed at capturing unreported online sales income, Nearly three-fourths (73%) of the gig workers surveyed don’t know the payment threshold above which they would receive a Form 1099-K and be required to file an IRS tax return.
Gig workers will be looking for advice from a tax preparer. Over 20% of the survey respondents plan to pay a tax professional for the first time as a result of 1099-K reporting changes and complexity.
Last year, the IRS extended its transition relief for the new Form 1099-K information reporting threshold,
The Avalara survey found that while 61% of respondents claim to be knowledgeable about Form 1099-K and its purpose, an equal proportion of 61% don’t know the 1099-K reporting threshold is lower this year and subsequent tax years. For subsequent tax seasons on the way to a $600 1099-K reporting threshold, only 18% surveyed could identify the correct threshold for 2026 and the final $600 reporting threshold for the 2027 tax season.
The respondents offered various predictions for how they would fare from the new income reporting requirements: 37% believe their business will be profitable following tax season, 36% responded they’ll likely break even, and 17% predict they’ll lose money due to the IRS changes.
More than one-third (37%) of gig workers surveyed said this is the first year they’re receiving a 1099-K, so 21% of respondents plan to engage a tax professional for the first time. Another factor in seeking professional advice could be the number of gigs these workers are juggling: 75% of survey respondents have two or more sources of income, 45% have three or more, and 16% have four or more. Accountants and bookkeepers will be essential to helping 1099-K newbies sort out the reporting and tax implications of multiple income sources.
The survey also indicated how respondents plan to move forward after tax season. To avoid crossing the $2,500 1099-K threshold next year, over 20% of workers expect to be quitting one or more of their gig economy jobs and 19% are changing their earnings strategy, while 15% will be using tax software for the first time. Another 20% intend to take on more under-the-table work, and 15% will switch to Zelle to avoid IRS reporting rules associated with PayPal and Venmo. Some 40% of those surveyed say they’ll take on one or more additional gig economy jobs. And 16% of survey respondents said they will be leaving the gig economy altogether and pursuing different work.
“Our survey data reveals the urgent need for basic knowledge and orderly direction on the part of gig economy workers to determine how best to comply with the lowered 1099-K digital payments threshold,” said Avalara general manager Kael Kelly in a statement Thursday. “This scrappy segment of our economy demonstrates DIY drive in creating a living from engaging in multiple jobs, non-traditional work, and sometimes essential services that support how consumers want to buy and receive goods and services – and they’re now faced with the additional challenge of sorting out new, last-minute tax regulations and reporting requirements. Businesses of all sizes, including independent workers, need a fast, robust, easy, and affordable way to e-file 1099 forms, and that capability is within reach through modern cloud software.”
The global economy is poised for “reasonable, but not particularly exciting” growth this year, yet uncertainties abound, according to a new report from the Association of Chartered Certified Accountants.
The
“The global economy should continue to grow at a reasonable, but not particularly exciting pace in 2025,” said ACCA chief economist Jonathan Ashworth in the report. “But it is a world marked by significant uncertainty. The risks are predominantly on the downside, amid potential changes in U.S. trade policy, a challenging geopolitical backdrop, political uncertainty and rising government bond yields.”
Economist Charles Goodhart suggested the U,S. economy may perform strongly in 2025, but Europe and the U.K. could struggle. Goodhart believes inflation could fall in the short run but will probably rebound in 2026 and 2027.
“My guess, on which I would not place a great deal of weight, is that the U.S. economy will do very well in 2025,” he said. “Both Europe and the U.K. will do relatively badly. Not only will higher U.S. import tariffs be a problem for Europe, but higher U.S. tariffs on imports from China will probably mean that China will want to export more of its goods to Europe, at a time when Germany’s business model is already under extreme stress.”
The emergence of AI agents promises new productivity breakthroughs, but hybrid solutions integrating other technologies will be crucial for sustained value, according to the report.
The ACCA interviewed seven CFOs from across the globe in various sectors for the report. While the interviewees did not appear to be expecting a notable slowing in global growth in 2025, there was some caution given the significant global uncertainty, including that related to the policies of President Trump.
“Technology, particularly AI, continues to be a priority, with businesses recognising both its potential and disruptive challenges,” said the report. “A wide range of risks were highlighted, including inflation (and changes in the price of important commodities), policy changes in large economies, cybersecurity, exchange rate movements, supply chains, climate change, social tensions, geopolitics, and fast-changing consumer habits. The latter two were also cited as opportunities. A recurring theme among CFOs is the need for agility, innovation and resilience in navigating an uncertain economic landscape.”
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