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For new businesses, we design and implement ownership structures - such as Subchapter C and Subchapter S corporations, general and limited partnerships, limited liability companies (LLCs) and business trusts - to minimize tax cost, limit the liabilities of business owners and preserve control of business operations. 

We frequently negotiate and structure buy/sell agreements (insurance-funded and otherwise) and other arrangements among business owners. We help established businesses buy and sell business assets, including the sale of the entire company. In these transactions our lawyers make maximum use of the rules that permit certain business dispositions to be achieved without current income tax. We also structure and draft employment agreements and other arrangements with key employees.

We are particularly sensitive to the special issues confronting family businesses and can help reduce or eliminate taxes when a family business is transferred to the next generation. Sullivan is known as a leader in Massachusetts state tax matters and we routinely advise clients on the state and local tax consequences of business transactions and help with structures to minimize state taxes.

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Massachusetts And Maine Receive Hurricane Related Tax Relief
The Internal Revenue Service delivered an unexpected surprise to taxpayers in Massachusetts and Maine this week by postponing to February 15, 2024 the deadline for various individual and business tax returns and tax payments that are otherwise due on or after September 15, 2023 and before February 15, 2024. The broad relief generally applies to individuals who live, and businesses (including tax-exempt organizations) whose principal place of business is located, in Massachusetts or Maine and includes various returns otherwise due on October 16, 2023, including Form 5500. Both the federal Department of Labor and the Pension Benefit Guaranty Corporation have publicly stated that Internal Revenue Service relief will apply with respect to their respective portions of the Form 5500. The devil is of course in the details (note the caveat about certain information returns, for example) and you are urged to review the announcements carefully. Absent explicit relief from the Massachusetts Department of Revenue or Maine Revenue Services, one should also not assume that similar relief is available with respect to state tax filings and payments. If you have any questions, please feel free to reach out to us.
Exploring the Contours of the Employee Retention Credit
In an effort to incentivize businesses to retain employees during the COVID-19 pandemic, the Coronavirus Aid, Relief, and Economic Security Act (CARES Act), signed into law by President Trump on March 27, 2020, offers incentives to businesses in the form of fully refundable tax credits. The Internal Revenue Service has provided guidance on the new credits through Notice 2020-22 (the Notice) and through Frequently Asked Questions (FAQs). In this client alert, we have synthesized in a question-and-answer format information from the CARES Act, the Notice and the FAQs. What are the eligibility requirements for employee retention credits? To be eligible to receive employee retention credits, employers must satisfy the following requirements: Cannot have obtained a Paycheck Protection Program (PPP) “forgivable” loan; Must be carrying on a trade or business during 2020; and EitherOperations of the employer are fully or partially suspended as a result of a governmental order that limits commerce, travel or group meetings (for commercial, social, religious or other purposes) in any calendar quarter as a result of the pandemic or The employer experiences a “significant decline in gross receipts” during the calendar quarter. Nonprofit organizations are eligible for this relief and are also not subject to the significant decline in gross receipts requirement. Neither governmental employers nor self-employed individuals, with respect to their own self-employment income, are eligible for employee retention credits. When are operations suspended by a governmental authority? What it means to have operations fully or partially suspended by a governmental authority is not particularly clear. One of the FAQs indicates that an employer may suffer from a partial suspension of operations even if the business can still continue to operate but not at its normal capacity. That FAQ then considers an arguably obvious example whereby a state governor issues an executive order closing all restaurants, bars, and similar establishments to reduce the spread of COVID-19 but those establishments are permitted to continue food or beverage sales to the public on a carry-out, drive-through or delivery basis. Less clear are cases in which a business shifts to a remote-work setting as a result of a governmental stay-at-home or similar order (such as the March 23, 2020 order to Massachusetts businesses issued by Governor Baker) but that are continuing to operate. It may be telling that the IRS used the dining example rather than other examples that have been used in similar situations in the past. Additional clarity would certainly be appreciated. How is a "significant decline in gross receipts" measured? A significant decline in gross receipts occurs in the first calendar quarter of 2020 in which the business’s gross receipts are less than 50% of the gross receipts for that same calendar quarter of 2019. The business is no longer considered to have a significant decline in gross receipts after a 2020 calendar quarter in which gross receipts are in excess of 80% of the gross receipts for that same calendar quarter in 2019. How are employee retention credits claimed? An employer can claim employee retention credits for an applicable quarter by not depositing the employer portion of Social Security taxes (6.2% of wages up to the 2020 Taxable Wage Base of $137,700) in an amount equal to 50% of an employee’s "qualified wages." (Note that the employer must still deposit the employer share of Medicare taxes, and federal income and Social Security and Medicare taxes withheld from the employee.) The maximum amount of qualified wages that an employer can take into account for all quarters is $10,000 per employee. As a result, the maximum credit available to an employer with respect to any individual employee is the lesser of $5,000 or 50% of the employee’s qualified wages. If the amount of employee retention credits that an employer is entitled to is more than the corresponding quarterly employer portion of Social Security taxes, the excess is treated as an overpayment. An employer can obtain a refund of this amount, after first applying any excess to the employer’s remaining quarterly employment tax liability, by filing new Form 7200. Form 7200 is the same form that is used to obtain a refund for the new Emergency Family and Medical Leave and Paid Sick Leave credits that were enacted as part of the Families First Coronavirus Response Act (FFCRA). Alternatively, the Notice provides that an employer can use all withheld amounts within a quarter (including the employer share of Medicare taxes, and federal income and Social Security and Medicare taxes withheld from employees) to fund qualified wages so long as those wages are paid prior to the time the deposit of the withheld amounts would otherwise be required without any failure to deposit penalty provided the requirements of the Notice are satisfied. What are qualified wages? The starting point for qualified wages is the definition of wages used for purposes of the Social Security tax (Box 3 of Form W-2). The following adjustments are then made – Only amounts paid after March 12, 2020 and before January 1, 2021 may be included. "Qualified health plan expenses," such as the employer’s cost of coverage, are included (or, stated differently, added back to the Box 3 amount). An employer must exclude any wages taken into account for purposes of determining Emergency Family and Medical Leave and Paid Sick Leave tax credits under FFCRA. (An employer can benefit from employee retention credits and the tax credits provided in FFCRA, but, not surprisingly, not for the same wages. Other limitations also exist, such as the prohibition of the credit with respect to wages for which the Work Opportunity Credit is claimed.) For employers who employed on average 100 or less full-time employees in 2019 (full-time meaning for this purpose that the individual was employed on average at least 30 hours per week), the qualified wages of all employees are available for purposes of claiming the credit. For larger employers, only the qualified wages of employees who are not providing services as a result of a suspension of the employer’s operations resulting from the pandemic or due to a significant decline in gross receipts are available for purposes of claiming the credit, and in this situation the amount cannot exceed what the employee would have been paid for working for an equivalent duration during the 30 days immediately preceding the economic hardship. In determining whether an employer is small or large for this purpose, an expansive aggregation rule applies that can result in parent-subsidiary and brother-sister affiliations using a more than 50% ownership test (rather than an at least 80% ownership test). The affiliated service group rules of Internal Revenue Code Section 414(m), as well as the anti-abuse rules of Internal Revenue Code Section 414(o), also apply. The following chart may be helpful in determining whether and how employee retention credits might apply. * * * Sullivan has developed a rapid response team of attorneys to help our clients and our communities cope with the impact of the COVID-19 pandemic and understand the implications of the CARES Act and other actions taken by state governments and the federal government. Please refer to Sullivan’s newly launched resource center at www.sullivanlaw.com/COVID19 for more information and for access to Sullivan’s library of related advisories. Please know that Sullivan is focusing substantial efforts to provide assistance to businesses and individuals affected by COVID-19 and benefited by the CARES Act. If you have questions about how to move forward and navigate the novel legal issues raised by COVID-19 and/or the CARES Act, please contact your primary Sullivan attorney or send a message to CARES@sullivanlaw.com.
David Nagle Featured in Massachusetts Lawyers Weekly’s Managing Partners Spotlight
David Nagle, managing partner of Sullivan & Worcester, has been featured in Massachusetts Lawyers Weekly’s “Managing Partners Spotlight,” which recognizes law firm leaders across Massachusetts for excellence in leadership, strategic vision, talent development, community engagement, and firm achievement. As managing partner, Dave works closely with the firm’s management committee, partners, associates and business professionals to advance the firm’s strategic vision, strengthen its culture of performance and collaboration, and support continued excellence across the firm’s core practice areas. He also brings more than 25 years of experience to his practice as a tax partner in the firm’s Boston office.
Joel Carpenter Selected for Massachusetts Lawyers Weekly Hall of Fame
BOSTON, MA – Massachusetts Lawyers Weekly has selected Sullivan & Worcester Partner, Joel Carpenter, for its 2025 Hall of Fame. Each year, Massachusetts Lawyers Weekly Hall of Fame recognizes attorneys throughout the state with more than 30 years of experience for career accomplishments, contributions to the bar and to the development of Massachusetts law, and efforts to improve the quality of justice. “I’m honored to be included among this year’s Hall of Fame recipients,” Carpenter said. “I’ve had the good fortune to work with highly talented and skilled attorneys and a great leadership team at Sullivan. This recognition also reflects the strength and capabilities of an outstanding law firm.” As former managing partner and co-managing partner of Sullivan for many years, Carpenter has been a guiding force behind the firm’s growth and resilience. He led the firm through the financial crisis of 2008 and again during the unprecedented challenges of the COVID-19 pandemic and helped ensure Sullivan’s steadfast commitment to its clients and values. “Joel has been a defining force at Sullivan for decades, not only through his steadfast leadership during times of challenge and change, but through the extraordinary clarity and judgment he brings to every situation. He has a rare gift for distilling complex problems into clear, actionable choices or reframing them entirely to reveal the path forward. His impact on our firm and clients has been profound, and this recognition is a fitting tribute to his remarkable career and enduring contributions to the legal profession,” said David Nagle, Sullivan’s managing partner. A respected leader in U.S. tax law, Carpenter has significant experience in the tax structuring of complex business and investment arrangements using partnerships, limited liability companies, and Subchapter S corporations. He advises private and institutional investors, including real estate investment firms, on all aspects of U.S. income tax matters related to fund formation, acquisition and disposition of property, structuring debt and equity investments, equity compensation plans, and tax planning for investors. He also advises companies on tax issues related to corporate mergers and acquisitions, financing for emerging companies, and counsels high net worth individuals on income and estate tax planning matters. Carpenter has received numerous professional accolades, including being named to Best Lawyers in America®, 2007-2025, PLC Which Lawyer? Leading Lawyers in Tax, 2008-2010, and Massachusetts Super Lawyers, 2005-2014 and 2017-2018. In addition to his active practice and firm leadership roles, Carpenter has been dedicated to community service and served as a tax advisor to many of Sullivan’s pro bono clients and nonprofit organizations. He was recently elected to the Board of Directors of Pioneer Law Public Interest Law Center (PLPILC), a nonprofit, nonpartisan legal research and litigation public interest law firm. PLPILC defends and promotes educational options, accountable government and economic opportunity across the Northeast and nationwide. The organization works to preserve and enhance liberties grounded in the Constitution and civil rights laws of the U.S. and the New England states. About Sullivan Sullivan & Worcester (Sullivan) is a global, mid-sized law firm with lawyers in Boston, London, New York, Tel Aviv and Washington, D.C. Sullivan’s clients, including Fortune 500 companies, leading financial services firms and asset managers, boards of directors, real estate companies, and emerging businesses, rely on Sullivan’s ability to navigate complex legal and operational landscapes, the impeccable judgment of its lawyers, and its commitment to best‑in‑class client service.