Think Outside the Tax Box

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