Think Outside the Tax Box

The story of Anne Milner Fields is one of the reasons family limited partnership (FLP) opinions appeal to me so much. Born in 1925, she grew up in a small town in Texas and then moved to Dallas where she got a job as a secretary and met prominent oil man Bert Fields Sr. They married, and she lived the life of a socialite until he died in 1963. She consciously turned herself into a businesswoman, g...

Following Betteridge’s Law of Headlines, the answer to the question posed in the headline is, “no.” Actually — because we’re talking about taxes here — we can say the answer is never so definitive, so let’s change it to “probably not.” Alternative minimum tax (AMT) is a type of parallel tax system. It requires certain items to be added back in determining alternative minimum taxable income (AMTI)....

We all know how messy tax returns can get when couples who used to file jointly divorce and there are children (and tax credits) involved. It’s often difficult to explain the rules surrounding Head of Household filing status and the various tax credits available to parent-clients who have separated or divorced. But what happens when the clients misunderstand and decide to fight about it in family...

The IRS has issued a statement about a new settlement offer that is going out for conservation and historic preservation easement disputes. It is similar to previous offers, but there is one big difference. The partnership will not have to make a payment at the time that it accepts the offer. Other than that, it is a similar to the deal offered in 2020. Taxpayers get to deduct what they are out-of...

Astute subscribers of Think Outside the Tax Box may recognize that writer Matt Metras frequently writes on Cryptocurrency and also on Tax Court cases. So, it feels like Christmas for him to be able to write about a tax court case about crypto. This is only the Third Tax court case to even mention crypto, and the first to look at the underlying principles of taxation. (The other two were about incl...

Many taxpayers have lived with a frustrating mismatch since the Section 163(j) limitation tightened after 2021 – the business may generate plenty of cash, yet its interest deductions are limited because adjusted taxable income (“ATI”) is too low, e.g., due to capex. The 2025 restoration of depreciation and amortization addbacks makes ATI planning relevant again, especially for groups that own valu...

The Internal Revenue Service has made no secret of its increased scrutiny of captive insurance arrangements, particularly those involving the small insurance company election. For taxpayers and their advisors, this has created understandable concern and, in some cases, hesitation about whether captive insurance remains a viable risk management and tax planning tool. Yet heightened scrutiny does no...

The Jeffrey Winick tax story is about one of the simplest methods of not paying taxes. That simple method of not paying is simply not paying. Winick is a very successful real estate broker specializing in retail leases. The company he founded, Winick Realty, now rebranded RTL has in the past been listed as one the top five of retail brokers in New York City. According to the RTL site: "Jeff h...

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 m...

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. It’s no wonder. Early on, most of us take every client...

In the Fall of 2025, Bitcoin reached an all-time high of over $120,000, since then it has fallen over 40% to under $70,000 in the first quarter of 2026. 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 Ch...

What if millions of dollars in IRS penalties and interest assessed during the COVID-19 pandemic were never legally owed in the first place? What if the deadlines we all relied on such as filing dates, payment dates, statutes of limitation were not just extended temporarily, but effectively suspended for more than three years? And what if the IRS doesn’t get the final say on that question? The 2025...

“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 a...

Pre-Covid I had an influx of new clients who felt that their tax professionals were not taking them seriously. They were making money on the internet. This was still fairly new for individuals who weren’t modeling, selling their own products, or services. Every person I onboarded that year shared a similar story. My CPA told me this is a hobby, not a real business. Were you that CPA? You don’t hav...

The Cohan rule is named for George M Cohan. George Michael Cohan (1878 – 1942) was a theatrical producer. Cohan was appealing a net deficiency totaling $238,102.28 from 6 returns from 1918 to 1923. One was for a short period as he switched to a June year end. The net deficiency would be roughly $3.9 million in today’s dollars. There were several issues. George had excluded income that had gone to...

Before Zohran Mamdani was elected, Richard Pollina of the New York Post reported that nearly a million New Yorkers were ready to flee the Big Apple because of fears about his administration. And they would not be fleeing just the city, but the entire state of New York. “The Carolinas, Florida, and Tennessee have emerged as top escape destinations thanks to lower income taxes and property taxes.” A...

As we discuss this topic, the most recent Tax Court opinion on a syndicated conservation easement deal is Jackson Stone South LLC. Good chance there will be another before we 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...

The IRS is not the same agency we dealt with a decade ago, or even three years ago. The pandemic accelerated operational strain, exposing long-standing infrastructure weaknesses while also prompting overdue investment and modernization. Some areas have improved meaningfully, including digital tools, faster account updates, and improved phone service during filing season. Other areas, however, feel...

Jessica, a self-employed consultant, was thrilled when she found a viral TikTok video promising a “little-known” tax trick. The video claimed she could get a huge refund by claiming a special Fuel Tax Credit and even writing off her family’s beach vacation as a business expense. Following the advice, Jessica filed an amended tax return and waited eagerly for a windfall. A few months later, instead...

When is a business really a business? As Supreme Court Justice Potter Stewart said in 1964, “I know it when I see it.” The US Tax Court, however, maintains a slightly less subjective standard. The Roots were pretty sure they were running a bona fide business; the IRS, however, didn’t share the sentiment. And since we’re reading about them in a segment called “Lessons Learned,” one should assume it...

Tax law is forever classifying people and making structures that either create benefits or disadvantages on your tax return. Part of getting the most from your clients return is about understanding the definitions of the IRS. Two that seem very similar, but have distinctly different consequences on your client's taxes, are real estate dealer and real estate investor . Listen in and learn more...

Most clients are familiar with the well-known accounts to save for retirement, such as the 401(k) and IRA. Some clients might be able to supplement those with a lesser-known vehicle as well. A life insurance retirement plan (LIRP) is a type of permanent life policy with a cash value basically funded by overpaying premiums. The money can eventually be taken as a tax-free loan against the policy for...

Big changes are coming to the student loan world (yet again), and they’re not the kind you can just skim past. The One Big Beautiful Bill Act (OBBBA) has reshaped how much students will be able to borrow, how they’ll repay it, and which programs will qualify for federal aid going forward. For financial and tax professionals, these shifts aren’t just policy updates. They’ll set the stage for how yo...

In every tax Facebook group or conference session, there's always that one pro excitedly talking about the latest app they've added to their "tech stack." But here's the dirty little secret: most of us aren't running integrated tech stacks. We're juggling a mix of disconnected tools that may or may not play nicely together. Let's stop pretending we're a...

Nothing derails a busy season schedule like being forwarded emails from client’s investors asking “are you sure the loss is allocated correctly?” It can expose a weakness in technical expertise – especially when it’s a partnership K1. Whether the operating agreement includes Safe Harbor or Target Capital allocations is one of the most important places to start for a preparer. And knowing these bas...