An Update on Cryptocurrency and the IRS

There was a lot of movement from the IRS involving cryptocurrencies in 2019. Prior to 2019, the IRS had issued just one piece of guidance regarding cryptocurrencies. That was by issuance of Notice 2014-21 in which the IRS let us know it would treat cryptocurrencies as capital assets rather than as a currency. There are…
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Substance over Form: No Friend of the Taxpayer

In the recent Messina case, the Ninth Circuit Court of Appeals affirmed the decision of the Tax Court denying S corporation shareholders losses as a result of lack of basis, particularly in this case, debt basis. In rendering their opinions, the Ninth Circuit and Tax Court discussed a taxpayer’s ability to argue substance over form…
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Are Your Life Insurance Death Benefits Taxable?

The income taxation of life insurance death benefits seems fairly simple initially. Many people know the general rule that death benefits are not subject to income tax. However, there are exceptions that can apply which will cause the beneficiary to owe income tax on the receipt of death benefits. This article describes certain of these…
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The Tax Consequences of Family Business Transactions

Parents are often in a position to help their children take advantage of business opportunities. A parent’s connections, business knowledge, expertise, and other intangibles acquired over may years of work can be used to benefit a child starting a career or business. Likewise, a parent may advance funds to a child to start or acquire…
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Can You Avoid Creditors by Moving Assets (or Yourself) to Another State?

A couple of recent cases illustrate situations where moving assets from one state to another may have the effect of shielding those assets from creditors. In both of the cases, judgment debtors moved assets to another state and succeeded in avoiding enforcement of the judgment. In re Cleopatra Cameron Gift Trust, a California Judgment Against…
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Higher Scrutiny for Tax Professionals: In Re Benavides

The Tax Court has just ruled against a CPA in a case involving income tax, self-employment tax, deductions for personal expenses, fraud, and other items. The CPA at issue, Al Benavides, had previously been criminally convicted for assisting a client in evading income tax liabilities. Although there are a number of substantive issues in the…
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Moore: What is a bona fide debt?

All too often, we see cases where failure to properly document a transaction or keep good records is a taxpayer’s undoing. A case recently handed down by the Tax Court illustrates how that can happen. In Moore v. Commissioner the taxpayer sought to expand his tax preparation business. To finance that expansion, Mr. Moore was able…
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A Refresher on Qualified Small Business Stock

By holding qualified small business stock (“QSBS”), noncorporate shareholders of qualifying C corporations can sell their stock tax free after a five-year holding period. Tax benefits associated with QSBS are nothing new. However, until recently, planning with QSBS has been neglected. The Tax Cuts and Jobs Act (“TCJA”) breathed new life into the potential benefits…
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Asset Protection Trusts: Update on Recent Litigation

Offshore and domestic asset protection trusts (“APT”) have been around for a while. Currently, there are seventeen states that allow a person to contribute assets to trust for their own benefit (i.e. a self-settled trust) and exempt those assets from claims of their own creditors subject to certain statutes of limitations and exception creditors. Other than…
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RERI Revisited on Appeal, $33M Deduction Denial Upheld

The Tax Court’s denial of a $33 million charitable deduction was affirmed by the D.C. Circuit Court of Appeals in a decision handed down on May 24, 2019. While the purported dollar value of the donation makes this case stand out, it involves a number of important issues including gift substantiation, substantial compliance, valuation, and…
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