IRS Determines Corporation Provided Brokerage Services; Taxpayer Denied QSBS Gain Exclusion

Compliance, Income Tax, Tax, Tax Controversy, TCJA

In a recent Chief Counsel Advice (“CCA”) issued by the IRS, the IRS concluded that the taxpayer’s sale of stock did not qualify for the gain exclusion as Qualified Small Business Stock (“QSBS”) under Section 1202 since the business of the corporation was akin to brokerage services.[1] The IRS concluded that the corporation’s business, one…
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Fab Holdings – It is called the “Tax Plan”

Cases, Income Tax, Tax, Tax Court

In another recent case involving a multi-entity tax savings strategy, pitched as the “integrated tax plan,” particularly leveraging “management fees,” we see again the Tax Court scrutinizing the legitimacy of the structure, incorporating a C corporation and a partnership, and in turn allowing the IRS to whipsaw the taxpayers.[1] Facts Around late 2009 through early…
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Heiting and the Claim of Right Doctrine

Cases, Court of Appeals, Income Tax

In the Heiting v. United States[1] decision issued on October 18, 2021, the United States Court of Appeals for the Seventh Circuit affirmed a district court decision[2] to dismiss a couple’s claim for a refund of taxes, rejecting the taxpayers’ argument that the repurchase of restricted stock previously sold by their trustee was effectively a…
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Crypto at ESA

Business Transactions, Compliance, Current Events, Estate and Gift Tax, Estate Planning, Fiduciaries, Income Tax, New Legislation, Tax

Since we’re the cool, diamond-handed, trendy-loving, FUD(fear, uncertainty, and doubt)-crushing, FOMO(fear of missing out)-haters and at the same time professionals, now seems just as good of time as ever to discuss what we are doing at our firm to familiarize ourselves and become more competent in the ever-growing and evolving world of magic internet money,…
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Proposed Tax Changes in the Updated Build Back Better Act

Charitable Giving, Estate and Gift Tax, Income Tax, New Legislation, Tax

Earlier this year I discussed President Joe Biden’s proposed tax policies, which was prepared in anticipation of President Biden’s impending announcement regarding the Build Back Better Act.[1] As we approach the end of the Biden administration’s first year, tax professionals are on the edge of their seat. A plethora of different legislative changes directed at…
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Injunctive Relief Hiding in Plain Sight? CIC Services, LLC v. IRS

Cases, District Court, Income Tax, Tax Controversy

So, we did not write on the first District Court case which was a loss for CIC Services, LLC (“CIC”) and Ryan, LLC(“Ryan”), the Plaintiffs. But, a Supreme Court decision gave the Plaintiffs another bite at the apple. This case involves Notice 2016-66 (“Notice”), the older-sibling notice to Notice 2017-10, in which micro-captive insurance transactions…
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Taxpayer Denied Contribution Deduction to Sole Proprietorship Profit-Sharing Plan for Income Paid Under Deferred Compensation Plan of Prior Employer

Cases, Income Tax, Tax Court

In a recent Tax Court case, a taxpayer was denied a contribution deduction for income paid into a sole proprietorship profit-sharing plan when the Court determined that such income had not been derived from the trade or business with respect to which the plan was established.[1] Rather, the income was paid to the taxpayer under…
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