Think Outside the Tax Box

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 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. Losses can be taken if a taxpayer fully exits their position, but the difficulty enters when the taxpayer would like to maintain their economic exposure to the cryptocurrency. Commentators often suggest that losses can be recognized since the wash sale rules for securities do not apply to cryptocurrency, and while this is partially true, the analysis does not end there. Tax practitioners and taxpayers must fully examine the details of the transactions in their entirety to determine whether a tax loss is deductible.In this podcast, we go over the various ways that tax law comes into play when selling and re-buying cryptocurrency, and discuss considerations that taxpayers should know before engaging in any transactions.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

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 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.Listen in to hear what the court actually decided and why it matters now.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

“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.Listen in to the interesting case of Mennemeyer v. Commissioner of Internal Revenue!This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

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 have to be. Change isn’t always bad. We have to be ready to adapt to report the new ways that people ae earning a living. Otherwise, we are leaving taxpayers unserved and money on the table. The influencer marketing industry is here, and it is real.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.To help them, we have to understand how their world works. Let’s look at:● What an influencer is● How influencers get paid● How influencers report their income● Tax deductible expenses for influencerson this episode of Think Outside the Tax Box!This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

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 his mother under an alleged partnership agreement. There were royalties excluded as belonging to someone else. There was a loss on an annuity contract. The partnership had deducted $10,000 to the Producing Managers’ Association to fight against actor’s unionizing. There was a deduction of $150,000 to secure management and booking rights to a theater. As an alternate argument, maybe the $150,000 could be depreciated. Were luxury taxes deductible? There was also an issue about the tax computation for the fiscal years due to rate changes.Listen in to learn about this fascinating case and historic tax decision and what it means today!This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

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.”And while evidence has not indicated this actually occurred, it’s still worth thinking about. 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. Listen in and let's take a review of recent developments.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

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 will take a look at it, but mainly we want to look at what tax practitioners have to reflect on. Let’s start with Jackson Stone...This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

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 frozen in time. Correspondence units remain slow, backlogs persist, and automated notices often fail to reflect what is actually happening on a taxpayer’s account.As tax professionals, we operate in the middle of this contradiction. Our effectiveness depends less on how the Internal Revenue Manual says the IRS should operate and more on understanding how it actually operates today. Just as importantly, our sanity depends on managing client expectations in an environment where taxpayers expect Amazon-level efficiency from an agency still reliant on decades-old systems.This audio outlines the practical realities of working with the IRS in 2025, what strategies are working, what remains broken, and how to set clear, healthy expectations so you can deliver results without burning out.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

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 of a refund check, Jessica received a stern IRS notice. Her so-called credits were disallowed, her refund was denied, and she now faced penalties. Jessica isn’t alone. Every tax season, well-intentioned taxpayers get lured by false tax advice on social media, only to end up in trouble. As tax professionals, we often meet panicked clients like Jessica who need our help to untangle the mess.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

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 did not go the way the Roots would have liked...This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

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!This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

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 anything from medical expenses and long-term care to supplemental retirement income to, for the wealthy, the payment of taxes on large estates.Listen in to learn more about helping your client with this sometimes over-looked complimentary benefit!This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

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 you’ll advise clients for years to come… and could even change the way you manage your own student loans.In our OBBBA student loan series, we break down the nuts and bolts of these new rules to help advisors (and borrowers) get some clarity on the collective question: “Seriously, what’s going on with student loans” This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

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 all building perfectly integrated ecosystems. What we really need is a tech portfolio—a curated collection of tools that serve our actual needs, reflect how we really work, and support the kind of client experience we want to deliver. Listen in as we discuss some realities of technology for the solo tax professional and their growing team.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

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 basics can be the difference between a confident reply or a lost week. Listen in as we discuss!This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

State and local business tax incentives are powerful tools that can significantly reduce a company’s tax burden and influence business decisions. Every U.S. state offers some form of incentive to attract or retain businesses, from tax credits and exemptions to cash grants and property tax abatements. For experienced tax professionals, understanding these incentives is crucial for effective tax planning and helping clients maximize savings. Listen in as we discuss ten key things to know about state and local business incentives, along with real-world examples and actionable insights. We’ll also wrap up with essential dos and don’ts when advising clients on these programs.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

The tax code is not kind to gamblers. All gambling wins are reportable as income. Losses are only deductible to the extent of wins and even that has limitations. Expenses of gambling, such as travel, meals, and lodging, are not deductible for casual gamblers.In Part 1 of this two-part podcast we will discuss deducting gambling losses for recreational and professional gamblers. We will also discuss additional deductions professional gamblers can take and how to report those deductions. Listen in!This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

The good news is that none of the changes to the Affordable Care Act, Medicaid, or other health-insurance-related tax items in the One Big Beautiful Bill Act (OB3A) were retroactive to the beginning of 2025. The bad news is that the first set of changes is coming in 2026. The worse news is that some changes that were not included in the final version of OB3A are included in a new Federal Rule – but the provisions of the Federal Rule are only temporary. Basically, what we have is some federal rulemaking that was designed to give Congress time to codify the rule’s provisions into law, but only some of the provisions were codified – which simply means the provisions are merely temporary, not invalid.This podcast is going to discuss some of the important provisions concerning healthcare coverage that are included in OB3A, one that didn’t make it into the law, but that is in the new Federal Rule, and two that kind of blew up on social media but aren’t in OB3A or in the new rule.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

This episode takes a sharp, accessible look at one of the most debated—and misunderstood—tax issues of our time: the SALT cap. With tax year 2025 looming, our hosts unpack the origins of the $10,000 deduction limit, explore the proposed increases in the OBBA legislation, and explain how it all ties into marriage penalties, PTE workarounds, and phaseouts. Whether you’re a CPA, EA, or tax planning pro, this episode equips you with the clarity and context to advise clients confidently and adapt strategies in real time. Tax policy is changing fast—stay ahead of the curve with this essential breakdown. This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

Taxes are scary enough before crooks get involved. And just like any tool ever invented by humans, it wasn’t long before technology became the plaything of scammers looking to pull off cons. Elderly clients who often have large life savings can be easy targets for scams, whether because of social isolation or emotional and cognitive problems, or maybe just because they didn’t keep up with the latest, frequent IRS or FBI warnings about being careful on the internet. Some elderly victims learn too late that it takes serious effort to resolve thefts of money – and potentially years to fix identity theft.These clients need to be extra vigilant. Listen in to learn what to tell them.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

Networking is vital to any profession and is no different for us Certified Public Accountants (CPAs). Attending conferences and seminars can be a game-changer, offering opportunities to learn, connect, and grow your professional network. These events are not just about business but also about personal and professional growth. However, to truly benefit from these events, it's essential to have a strategy in place. Listen in to learn more...This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

So, your client is planning to welcome a foreign partner on board—or maybe one’s already landed. International partnerships can be a thrilling journey filled with opportunities, but let’s be honest: they also bring a fair amount of turbulence.Yes, cross-border ventures can unlock exciting destinations for growth and investment, but they also come with some heavy-duty baggage—think IRS paperwork, withholding headaches, and estate tax landmines. If you're a tax planner gearing up for this global expedition (especially if it's your first trip), this article and episode is your passport to smoother travels.Let’s unpack what you need to know to keep your clients out of customs trouble, avoid baggage fees in the form of penalties, and land safely on the compliant side of tax planning!This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

College tuition continues to climb, and for many families, financial aid can make or break their ability to afford their child’s higher education dreams. What most don’t realize is that their tax return — filed long before students even begin applying for college — plays a major role in determining how much financial aid they’ll receive. This is where you come in. Tax professionals and financial planners are uniquely positioned to help clients qualify for more college financial aid. But only if you know what to look for. Listen in to learn more!This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

Tax rules are generally designed with a purpose in mind. Most rules serve to define the tax base and tax rates. Many others serve to serve a behavioral purpose to encourage or discourage certain activities. The focus of this podcast stems from tax rules that are a combination of favoring certain activity such as generation of capital gains, and a limitation on such gains for certain taxpayers, such as the so-called “hot assets” rule for partners under IRC Section 751, Unrealized Receivables and Inventory Items. While Section 751 has been in the tax law for decades, a new application of it was raised by both the IRS and California FTB. This podcast summarizes Rawat, TC Memo 2023-14, rev’d, No. 23-1142 (DC Cir., 2024), and FTB Legal Ruling 2022-02, and offers observations on their relevance to tax research and practice.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

Looking to cut down on self-employment taxes on your partnership income? Converting your partnership into an S corporation might be the answer.If you currently run your business as a partnership or an LLC taxed as a partnership, you’re probably familiar with the sting of self-employment taxes. Unlike shareholder-employees of an S corporation, who only pay Social Security and Medicare taxes on their salaries, partners typically get hit with self-employment taxes on their entire share of the business’s net income. That can add up fast.By transitioning to an S corporation, you can restructure how you take your income—splitting it between salary and profit distributions. The big advantage? Those profit distributions are not subject to self-employment tax, potentially saving you thousands each year.So, if reducing your tax burden sounds appealing, listen in as we break down how a tax-free Section 351 incorporation works and what you need to know before making the move.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

With the rising cost of higher education and greater reliance on student loans, taxpayers are looking for every opportunity to ease the financial burden of earning a degree. Fortunately, several higher education tax benefits are available to help offset the high cost of tuition, student loans and other education-related expenses. However, certain eligibility requirements — such as income limits and tax filing status — often trip up taxpayers along the way. Understanding the nuances of these tax benefits for higher education can ensure your clients take full advantage of available tax savings. Listen in to learn more!This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

The IRS is ramping up scrutiny of high-net-worth individuals and businesses, increasing audit rates by over 50% for those earning above $10 million. Recent IRS initiatives backed by Inflation Reduction Act funding have intensified enforcement on wealthy taxpayers, large partnerships, real estate investors, and tech businesses. IRS agents are digging deeper during audits and expecting taxpayers to produce more documentation to support every position on their returns. To help clients navigate this environment, tax planners must take proactive steps to bolster documentation and audit readiness.Listen in as we go over ten authoritative strategies, complete with industry examples, IRS policy references, and best practices, to prepare for the increased IRS focus on documentation!This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

Late afternoon on the Friday before New Year’s Eve, the Treasury released another 115 pages of Digital Asset Regulations, along with a 13 page notice for good measure. As we’ve discussed previously on TOTTB, the last set of regs punted on a number of more complex crypto issues. This most recent release is all about one of those issues, Decentralized Finance, better known as “DeFi.” What is DeFi? What is CeFi? What does all this mean for tax planning? Listen in as we break it all down in this latest episode.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

Historic buildings make a beautiful location for doing business. Unfortunately, many of them may seem out of the price range of small business owners. But, that’s not necessarily the case! The state and federal governments have an interest in preserving these properties, and they are willing to give you tax credits for buying and restoring a historic building. Listen in to learn how you can help your clients with this great tax benefit!This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

Is student loan forgiveness taxable? Yes. No. Maybe. Sometimes. It primarily depends on the student loan forgiveness program. But like everything else with student loans, there are a number of other factors at play. Why make it easy when you can thoroughly confuse taxpayers, federal student loan servicers and financial planners for years to come? Listen in to learn when student loan forgiveness might be tax-free and how to prepare your clients for taxable loan forgiveness.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

There are a few tax rules new for 2025 that may catch some individuals and their tax advisers by surprise. These changes have not received lots of attention either because they are overshadowed by related changes that are more significant, or they were enacted a few years back with a future effective date that arrives in 2025. This article covers changes for 2025 that you will want to be sure to share with clients to avoid surprises at a later date.From the article by Annette Nellen, CPA, CGMA, Esq. posted on 01-15-25.This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

As summer turns to fall, the leaves turn and houses start being decorated, the air becomes crisper and the internet fills with year-end tax tip pieces. I call them tip sheets. I just love reading tip sheets, but I’m retired from active practice. Somebody who doesn’t have time on their hands might look at two or three and figure they have seen it all and didn’t learn anything they didn’t know already. I’m here to tell you that if you keep hunting, you might find some gems. But better than that, I will share what I have found in the event you don’t have the time or inclination to look at another twenty or thirty tip sheets.Created from the Peter Reilly, CPA article posted 12-15-24This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

There are roughly 42.7 million federal student loan borrowers as of Q4 2024, creating an opportunity to provide additional insight to your clients beyond tax preparation. By leveraging certain tax and repayment strategies, you can help your clients reduce their tax liability and lower their student loan payments in one strategic swoop. Listen in to learn how...Created from the Caitlin See, MPA article posted 12-15-24This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax

On December 3, 2024, a U.S. District Court judge issued a nationwide preliminary injunction prohibiting FinCEN from enforcing the Corporate Transparency Act (CTA) and its associated Reporting Rule. This injunction halts the January 1, 2025, deadline for Beneficial Ownership Information (BOI) reporting, leaving many tax professionals and business entities questioning their compliance obligations.However, this pause is temporary. The government has already filed an appeal, and the injunction could be modified or overturned at any time. FinCEN has acknowledged that reporting companies are not currently required to file BOI reports but may do so voluntarily.What Does This Mean for Reporting Entities? Listen in to find out!Created from the Dominique Molina, CPA, MST, CTS article posted 12-15-24This podcast is meant for entertainment purposes only. For the more thorough, complete, and accurately written version of this article which includes citations, visit us at http://www.tottb.tax