The Often-Overlooked Benefits of Qualified Small Business Stock

If you started a business organized as a C corporation, you may be able to avoid some, and possibly all, tax liability when you sell the stock of the C corporation. As previously written upon by Gray Edmondson,[1] Section 1202 of the Internal Revenue Code (“Code”) provides for the exclusion of gain on Qualified Small…
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Yet Another Proposed Listed Transaction – CRATs and Annuities

On March 25, 2024, the IRS issued Prop. Reg. Section 1.6011-15[1], which designates certain transactions involving charitable remainder annuity trusts (“CRATs”) in tandem with single premium immediate annuity (“SPIA”) products as listed transactions[2]. Last year, I wrote an article in which the Tax Court decided against a taxpayer couple who undertook this exact transaction.[3] Now,…
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Crider Trust Case – The Case for the Cautious Fiduciary

On February 8, 2024, the Mississippi Supreme Court issued its opinion[1] regarding an issue of first impression regarding Mississippi’s Principal and Income Act of 2013 (the “Act”).[2] As a worthwhile note, the Court noted that this is an issue of first impression and acknowledged as well as appeared to oblige the parties so as to…
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The 2024 Dirty Dozen – The IRS’s Annual Warning

Every year, the Internal Revenue Service (“IRS”) releases its “Dirty Dozen.” The Dirty Dozen, as written previously about by my colleague, Devin Mills,[1] is a list of twelve prevalent scams the IRS bodes taxpayers to be weary of during tax season, as they “put taxpayers, businesses, and the tax professional community at risk of losing…
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The Corporate Transparency Act is Here: What You Need to Know

For the the most recent updates from FinCEN, see https://fincen.gov/boi/newsroom Update (3/4/2025): On February 27, 2025, FinCEN announced that it will not issue any fines or penalties or take any other enforcement actions against any companies based on any failure to file or update beneficial ownership information (BOI) reports pursuant to the Corporate Transparency Act…
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The Corporate Transparency Act Receives its First Blow in Court

The late Justice Antonin Scalia once remarked that federal judges should have a rubber stamp that’s says “Stupid But Constitutional.” The Constitution, in other words, does not allow judges to strike down a law merely because it is burdensome, foolish, or offensive. Yet the inverse is also true – the wisdom of a policy is…
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Insurance Arrangement Found to be Split Dollar Insurance Arrangement

Split dollar life insurance arrangements can take on a number of forms, and the exact structure of the arrangement determines the tax consequences, which can become complicated quickly. In a recent case out of the District Court of Ohio, the court held that an insurance arrangement between a single member C corporation, Peter E. McGowan…
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Monetized Installment Sales – Proposed Regulations will Lead to Burdensome Reporting Requirements and Increased Scrutiny

Monetized Installment Sales, as previously written upon by Gray Edmondson,[1] have been subject to increased scrutiny by the IRS in recent years, making its “Dirty Dozen” list in each of the last three years.[2] The IRS remains on the offensive in scrutinizing such transactions, issuing proposed regulation under Internal Revenue Code Section 6011 in August…
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Life Settlements of Life Insurance Policies: What, When, and How

Many individuals take out life insurance policies for valid planning reasons which later are no longer needed or desirable. Alternatively, the policy owner may need current liquidity. While many policies can be surrendered for their cash value or the owner may take loans against the policy, there may be other options. One of those options…
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