Podcast Article Archives - Think Outside the Tax Box

Podcast Article

By Peter J Reilly CPA

When Debts Go Bad: The Challenges of Deducting Delinquent Debts

It is painful when you finally realize that the money you expected to be repaid is never coming back. The tiny silver lining in that cloud might be the tax benefit of “writing off” the debt. Unfortunately, that silver lining may well be eclipsed by an even bigger cloud. Writing bad debt off is not that easy, and there’s probably no silver lining to that cloud. Ironically, you might find that the mistakes that caused you to be holding a bad debt might be what prevents you from getting a usable deduction.

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Niche Down to Scale Up: How Specialization Drives Visibility and Profitability

For many accountants, narrowing our focus can feel risky. We are trained to serve anyone who needs help and provide stability in any financial situation. Choosing a niche often raises concerns: Will we turn away good clients? Will we limit opportunities or reduce business stability? These are common doubts many of us have faced in our careers.

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Tax Loss Harvesting with Cryptocurrency

In the Fall of 2025, Bitcoin reached an all-time high of over $120,000. Since then, it fell over 40% to under $70,000 in the first quarter of 2026, before slightly recovering, currently resting around $75,000 as of this writing. With the steep drop in the price of Bitcoin and other cryptocurrencies, a common question from taxpayers is whether they can use the current losses to offset their other income. Large investors and professionals such as Grant Cardone and Shehan Chandrasekera (Head of Tax Strategy at Cointracker) have suggested that cryptocurrency can be sold and bought back immediately to claim the tax benefits. As with most things, the answer to this is not as simple as they portray, and many commentators, influencers, and sometimes professionals, miss the intricacies of cryptocurrency taxation.

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Client Alert

Kwong v. United States: A Pandemic-Era Decision That Could Reshape Tax Deadlines, Penalties, and Refund Opportunities

The 2025 court decision, Kwong v. United States, is quietly gaining traction among tax professionals for exactly these reasons. Its implications could be far-reaching, potentially opening the door to refund claims, penalty abatements, and revived tax deadlines that many assumed were long closed. But there’s a catch: the opportunity to act may be time-sensitive, and the window to preserve claims could begin closing in just a few short weeks. Here’s what the court actually decided and why it matters now.

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Client Alert

Lessons Learned from the Tax Court: An Olive Branch in Tax Court

“Everything is deductible until the audit” is an adage frequently repeated in the tax preparation industry. Generally, it’s mentioned tongue-in-cheek, but today’s taxpayer (and her tax pro boyfriend) may have taken it a bit too literally. Additionally, cutting corners may seem like a time-saving strategy in the moment, but the potential to backfire can’t be ignored. In this case, the taxpayer is about to learn things the hard way.

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Remember, Influencers, the IRS Follows You Too!

The influencer marketing industry was able to grow during Covid as many advertisers had to adjust or cancel their marketing campaigns. This was because more people were sitting at home consuming content on social media. This new opportunity for smaller influencers has created a new group of taxpayers who need to know their new filing obligations. They’ll also be open to tax planning strategies that you have to help them reduce their tax liability.

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Client Alert

George M. Cohan’s Tax Triumph: The Rise and Erosion of the Cohan Rule

The Cohan rule is named for George M. Cohan. George Michael Cohan (1878 – 1942) was a theatrical producer. In the decade before World War I, he was called the “man who owned Broadway” and is considered the father of American musical comedy. In 1940 he was awarded the Congressional Gold Medal for his contribution to morale during World War I with his songs “You’re a Grand Old Flag” and “Over There,” the first time the medal was awarded to someone in an artistic field. But his most enduring legacy may be the tax rule that shared its name.

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Fleeing High Tax States And The Stickiness Of Domicile

Part of preparing to leave a high state tax is facing up to the fact that the tax collectors of high-tax states can be kind of clingy. There is more to changing your residence for tax purposes than simple steps like a new driver’s license and a change in voter registration.

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Reflecting On The Conservation Easement Mess

As I write this, the most recent Tax Court opinion on a syndicated conservation easement deal is Jackson Stone South LLC. Good chance there will be another before I finish. Estimates indicate that there are over a thousand docketed cases. Jackson Stone can serve as a pretty good example of how the conservation easement opinions have been going, basically not well for the taxpayers. So we will take a look at it, but mainly I want to look at what tax practitioners have to reflect on.

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