The Tax Factor: How It Can Make or Break Your M&A Deal
Posted by Cheryl A. Jankowski on November 24, 2025
When buying or selling a business, taxes aren’t just a detail, they can significantly influence the outcome of the deal. If you’re planning a merger or acquisition, understanding the tax implications upfront is essential to avoid costly surprises.
Asset Sale vs. Stock Sale: What’s the Difference?
From a tax perspective, deals are typically structured in one of two ways:
- Asset Sale: The buyer acquires specific assets of the business rather than the entire entity. This approach is common when the buyer wants only certain product lines or resources. It’s also the only option if the business is a sole proprietorship or a single-member LLC treated as such for tax purposes.
- Stock Sale: If the business is a corporation, partnership, or an LLC taxed as a partnership, the buyer can purchase ownership interests directly. Whether the entity is a C corporation or a pass-through entity (such as an S corporation, partnership, or LLC) will have a major impact on tax treatment.
Why Structure Matters
The Tax Cuts and Jobs Act (TCJA) introduced a flat 21% corporate tax rate for C corporations, a provision that remains unchanged under the One Big Beautiful Bill (OBBB). This lower rate can make acquiring C corporation stock appealing because the company retains more after-tax income, and any future gains on appreciated assets are taxed at that favorable rate.
For pass-through entities, the TCJA’s reduced individual tax rates, also made permanent by the OBBB, can be advantageous. Income flows through to the buyer’s personal return and may qualify for the qualified business income deduction, further reducing tax liability.
Tip: In certain cases, a stock purchase can be treated as an asset purchase through a Section 338 election. Consult a tax advisor to see if this strategy works for your situation.
Seller vs. Buyer Priorities
- Sellers often favor stock sales. Why? Selling interests typically results in long-term capital gains (if held for more than a year), which are taxed at lower rates. Plus, liabilities generally transfer to the buyer.
- Buyers, on the other hand, usually prefer asset purchases. This structure limits exposure to unknown liabilities and allows for a step-up in basis—meaning the buyer can increase the tax basis of acquired assets to the purchase price. This step-up can reduce taxable gains on future sales and boost depreciation and amortization deductions.
Don’t Overlook Other Tax Factors
Beyond the structure of the deal, issues like employee benefits and compensation plans can create unexpected tax challenges during a merger or acquisition. A thorough review is critical.
Plan Ahead for Success
Selling a business, you’ve built or buying one for the first time is a major financial decision. Before negotiations begin, evaluate the tax consequences to avoid unpleasant surprises later. A proactive approach can help ensure your transaction is both strategic and tax efficient.
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Cheryl has extensive experience working with business owners and individuals on minimizing taxes, with a focus on succession planning. With a thoughtful approach, Cheryl helps clients explore their long-term goals and plan accordingly. Leveraging Cheryl’s expertise in this area, the goal is to implement plans that achieve the wishes of the client and provide for tax-efficient transitions. Cheryl’s passion for working with corporations and individuals has allowed her to become a trusted business advisor. She has worked with clients not only in the Western New York region but also throughout the country. The breadth of this experience has allowed her to collaborate with other professional advisors to ensure that plans are flexible and innovative in the ever-changing world in which we live. Cheryl started her career with the Firm in 1991 and rejoined in 2019 adding additional strength to the tremendous talent of the Lumsden McCormick tax team.