In February 2025, the United States Supreme Court issued a landmark ruling in Dewberry Group, Inc. v. Dewberry Engineers Inc., clarifying the boundaries of liability for corporate affiliates in trademark infringement cases under the Lanham Act. The decision, which reversed a $43 million disgorgement award against Dewberry Group that included the profits of its affiliated companies, has sent ripples through the corporate, intellectual property, and M&A legal communities.

Acquiring an S-Corporation is a significant event for both buyers and sellers, and it’s not as simple as just signing on the dotted line. The process is filled with legal and tax considerations that can have long lasting effects on both parties; a process that is unique to S-Corporations. If you’re contemplating such a transaction, it’s crucial to understand not just the basics, but also the issues that can arise.

When structuring a business, asset protection is a critical consideration. Many entrepreneurs mistakenly assume that electing S-Corp status for their corporation provides the same liability safeguards as forming an LLC. However, a key distinction lies in charging orders - a legal remedy that determines whether creditors can seize ownership or control of your business.

Purchasing a business in North Carolina can be a lucrative and exciting opportunity, but it also comes with a web of legal, financial, and operational risks. One of the most significant, and overlooked, risks is that of successor employer liability. This risk is particularly relevant when the seller has engaged in employee misclassification, treating workers as independent contractors (1099) when the law requires them to be classified as employees (W-2).

Multi-step transactions in mergers and acquisitions are not just strategic maneuvers for operational integration-they are also critical tools for optimizing tax outcomes. These structures, which unfold across phased legal and financial steps, create unique opportunities and challenges for buyers, sellers, and their advisors.

When structuring the sale or acquisition of a business, understanding the tax implications is crucial because they can significantly affect the overall value of the transaction for both buyers and sellers. Among the various tax provisions available, two stand out for their ability to transform stock sales into asset sales for tax purposes: Section 336(e) and Section 338(h)(10) of the Internal Revenue Code.

A frequent misunderstanding is that “LLCs cannot own S corporations.” In reality, the rule is that entities taxed as partnerships or corporations cannot be S corporation shareholders. A single-member LLC, if disregarded for tax purposes and owned by an individual or other eligible person, is not treated as a separate entity and thus does not violate the rule.

A Section 338(h)(10) election is a nuanced and powerful provision within the Internal Revenue Code, designed to provide flexibility in the tax treatment of certain corporate acquisitions.

The S-Corporation, or S-Corp, is a fixture in American business, prized for its tax efficiency and liability protections. Yet, confusion abounds-one of the most common errors is thinking of the S-Corp as a type of business entity, like an LLC or a C-Corporation.

For entrepreneurs in North Carolina and beyond, understanding these factors is crucial before making a decision.