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Internal Revenue Service Shareholders Tax Planning

The United States Internal Revenue Service is a bureau of the United States Department of the Treasury. The IRS is charged with collecting revenue and enforcing the Internal Revenue Code.  
Foster Garvey PC

One Big Beautiful Bill Act, H.R. 1 – 119th Congress (2025-2026): Part V – Qualified Small Business Stock Exclusion / Code Section...

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In this fifth installment of my multi-part series on the One Big Beautiful Bill Act, Steve Nofziger and I discuss a provision of the Act that impacts certain business owners who are contemplating a sale of their shares, Code...more

DarrowEverett LLP

Business Succession Planning: Pros and Cons of Passing S Corp Shares in Trust

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Business succession planning and estate planning are often linked together, particularly in the case of closely held family businesses. In the case of a shareholder who wishes to pass along their shares of an S corporation as...more

Rivkin Radler LLP

Terminating a Trust? Don’t Forget to Consider This Tax Issue

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Every conveyance of property or of an interest in property from one person to another is prompted, or at least influenced, by economic considerations. The parties to the transaction may swap properties, or one party may...more

Keating Muething & Klekamp PLL

Documentation is Key When Claiming QSBS Benefits

In recent years, the utilization of qualified small business stock (“QSBS”) under Section 1202 has grown considerably. Many businesses are formed as corporations at conception, private equity investors calculate the tax...more

Foster Garvey PC

A Journey Through Subchapter S / A Review of The Not So Obvious & The Many Traps That Exist For The Unwary: Part XVI – Changes in...

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Now that the scurrying around and worrying relative to developments impacting the Corporate Transparency Act (“CTA”) that were coming at us with laser speed are on a slow simmer, I can turn my attention back to my multi-part...more

Lippes Mathias LLP

Taxpayer Beware: The Pitfalls of Section 965 Installment Payments

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For the taxable years ending on December 31, 2017, and 2018, Section 965[1] of the Internal Revenue Code required U.S. shareholders (as defined in Section 951(b)) to pay a transition tax on the untaxed foreign earnings of...more

Venable LLP

Type F Reorganizations: General Overview and the Problem of Dissenting Shareholders

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Choosing the type of entity to form and where to form it are two of the most common early legal decisions that founders make when they start their own businesses. Founders typically register their companies in the state where...more

DarrowEverett LLP

Unlocking Tax-Free Gains: The Power of QSBS in Mergers & Acquisitions

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Internal Revenue Code (IRC) Section 1202 offers a significant tax incentive for investors in qualified small business stock (QSBS). This provision allows eligible shareholders to exclude up to 100% of capital gains realized...more

K&L Gates LLP

The Inside Basis: Potential Pitfalls of F-Reorganizations

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On this episode of The Inside Basis, host Randy Clark discusses some common issues in F-reorganizations involving S-corporations, a popular structural approach used in private equity transactions....more

Foster Garvey PC

A Journey Through Subchapter S / A Review of The Not So Obvious & The Many Traps That Exist For The Unwary: Part XIV – An S...

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In this Part XIV of my multi-part series on some of the not-so-obvious aspects of Subchapter S, I explore a narrow aspect of Subchapter S that is often ignored or forgotten. An S corporation is not always a mere extension of...more

Vorys, Sater, Seymour and Pease LLP

The Importance of Actively Monitoring S Corporation Compliance

Many banks have elected to be “S Corporations” for tax purposes. This status can provide significant tax benefits to the bank’s shareholders, but it also comes with several ongoing technical requirements. Failure to satisfy...more

Eversheds Sutherland (US) LLP

Recent administrative guidance hints at tax accounting priorities heading into 2025

IRS LB&I has updated several pieces of administrative guidance, including a notice regarding the transition period for complying with increased substantiation requirements for research credit refund claims and two practice...more

Foster Garvey PC

A Journey Through Subchapter S / A Review of The Not So Obvious & The Many Traps That Exist For The Unwary: Part XIII – What...

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Basic Rules - IRC § 6501(a) generally requires the IRS to assess tax within three (3) years after a tax return is filed by the taxpayer. There are two (2) notable exceptions to this rule under IRC § 6501(c) and (e),...more

Foster Garvey PC

A Journey Through Subchapter S / A Review of The Not So Obvious & The Many Traps That Exist For The Unwary: Part XI – A...

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In this Part XI of my multi-part series on some of the not-so-obvious aspects of S corporations, I explore a topic that should be obvious but which appears to be ignored by many taxpayers and their tax advisers – accurate...more

Kaufman & Canoles

Section 1202 QSBS - The Overlooked Arrow in the Business Succession Quiver

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Business owners considering exit options from their businesses often can be blinded by purchase price figures and proceeds, often “accepting” that paying capital gains tax is part of the deal. The ability to avoid or defer...more

Foster Garvey PC

A Journey Through Subchapter S / A Review of The Not So Obvious & The Many Traps That Exist For The Unwary: Part VI – Revocation...

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This sixth installment of my multi-part series on Subchapter S is focused on the revocation of an S corporation election. While the rules relating to revocation are fairly straightforward, there are a few nuances that may...more

DarrowEverett LLP

Accidental Termination on Purpose? S Corp Ruling Could Be Huge For QSBS Owners

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Qualified Small Business Stock (“QSBS”) is arguably one of the largest “gifts” Congress has given taxpayers by excluding from a shareholder’s gross income the greater of $10 million or 10 times the shareholder’s basis in the...more

Foster Garvey PC

A Journey Through Subchapter S / A Review of The Not So Obvious & The Many Traps That Exist For The Unwary: Part IV – Suspended...

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This fourth installment of my multi-part series on Subchapter S is focused on suspended losses of an S corporation. While the rules seem straightforward, their application can be tricky, especially given legislative changes...more

Hinckley Allen

Converting an LLC to an S Corporation: A Mistake Waiting to Happen

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Limited liability companies (LLCs) offer significant tax flexibility – for one thing they can elect to be treated as disregarded entities, partnerships, C corporations, or S corporations, and can even shift between those tax...more

WilmerHale

State Taxation of Qualified Small Business Stock: Federal Tax Exclusion Not Always Replicated at State Level

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In the event of an M&A transaction, many stockholders plan to take advantage of the exclusion from federal taxable income of gain realized from the sale or exchange of “qualified small business stock” (QSB stock). Section...more

Freeman Law

IRS Issues Proposed Regulations on Section 951(a)(2)(B) Planning

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Introduction: Consolidated Groups and Section 951(a)(2)(B) Tax Planning - On December 9, 2022, Treasury and the IRS released proposed regulations that are intended to stop certain U.S. shareholder tax planning under...more

Dorsey & Whitney LLP

DSU Plans May Run Afoul of U.S. Deferral Election Timing Rules Resulting in Adverse U.S. Tax Treatment

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A Canadian company adopting a deferred share unit plan (DSU plan) for its directors must consider U.S. tax implications for U.S. taxpayers. It is important to remember that U.S. citizens and U.S. residents for tax purposes...more

Levenfeld Pearlstein, LLC

Does your Goodwill Go Home at Night? The Sale of Personal Goodwill Offers Considerable Tax Planning Opportunities for Closely-Held...

It is important to consider tax planning opportunities when selling your business, particularly where a business is a closely-held professional service corporation and the proposed structure of the deal is an asset sale. In...more

Rivkin Radler LLP

Constructive Dividends and The Closely Held C Corporation

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Withdrawing Value- Any tax adviser who has represented closely held businesses and their owners long enough realizes there are certain recurring themes that transcend the otherwise unique characteristics of the industry of...more

Opportune LLP

Gift & Estate Tax Valuation: 5 Things To Remember

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Here are five things to remember when performing the valuation of shares of a closely held entity for gift and estate tax reporting...more

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