Private M&A Transactions: Tax Considerations of Stock and Asset Sales, Shareholder Classifications, Acquisition Structures, and Key Provisions

Louis Vlahos | Rivkin Radlers

Louis Vlahos practices tax law and has extensive experience in corporate, individual and partnership income taxation, and in estate and gift taxation, including tax planning, ruling requests and tax controversy.

He advises clients in connection with corporate organizations and reorganizations; sales and acquisitions of businesses; corporate distributions, redemptions, liquidations and spin-offs; shareholder and buy-sell agreements; partnership organizations, agreements, reorganizations, distributions, and other transactions; real estate sales, exchanges and operations; executive deferred compensation arrangements; estate and succession planning, including the transfer of business interests, and estate and gift tax audits; New York business tax issues; charitable giving; tax-exempt organizations; private foundations; and not-for-profit restructuring. He frequently writes about Tax Law as it applies to closely held businesses.

Lou counsels not-for-profit corporations in connection with reorganizations. He has advised cultural institutions, hospitals and other nonprofit organizations on their tax-exempt status, corporate restructuring, the creation and operation of supporting organizations (including fundraising entities), the structuring and acceptance of charitable gifts (including charitable trusts), compensation and other  excess benefit issues, deferred compensation arrangements and the taxation of unrelated business income.

Additionally, he has lectured on subjects such as corporate transactions and tax issues in the not-for-profit community, and he has written for various legal publications. Lou is a member of the Estate Planning Council of Nassau County and a former member of the IRS Taxpayer Advocacy Panel (TAP).

Super Lawyers recognized Lou as a Top Rated Tax Attorney from 2013 to 2023. In 2024, he placed No. 1 on the topic of tax law in JD Supra’s Reader’s Choice Awards and No. 2 from 2021-2023. Additionally, Lou was named to Best Lawyers in America® for Tax Law from 2023-2025.

Lou received the Cornerstone Award from the Lawyers Alliance of New York. Since 1997, Lawyers Alliance has presented Cornerstone Awards annually to a select group of individuals and institutions that have made extraordinary contributions through pro bono legal services. Lou is also the author of the award-winning blog, TaxSlaw.

I. Mergers and acquisitions (M&A) federal tax considerations | 1:00pm – 1:15pm

II. Taxable acquisitions | 1:15pm – 1:25pm

III. Sale of stock | 1:25pm – 1:35pm

IV. Sale of assets | 1:35pm – 1:45pm

V. C corporations and shareholders tax implications | 1:45pm – 1:55pm

VI. S corporations and shareholders tax implications | 1:55pm – 2:00pm

Break | 2:00pm – 2:10pm

VII. Installment reporting | 2:10pm – 2:20pm

VIII. Alternative acquisition structures (mergers, equity transfers) | 2:20pm – 2:30pm

IX. IRC 338(h)(10) election | 2:30pm – 2:40pm

X. IRC 336(e) election | 2:40pm – 2:50pm

XI. F reorganizations | 2:50pm – 3:00pm

XII. Additional considerations (compensation, non-compete, personally owned assets) | 3:00pm – 3:10pm