Business Strategies Archives - Page 3 of 32 - Think Outside the Tax Box

Business Strategies

By Joshua Youngblood, EA, CTRS, CRETS, NTPI Fellow

Small Mistakes With Huge Costs for Your Client’s Tax Returns

We’ve all been there. A client walks into your office and, somewhere in the conversation, you realize that a seemingly minor oversight, a missed deadline, a form nobody filed, an election nobody mentioned, has spiraled into a five- or six-figure tax problem. In my years of practice, some of the most expensive mistakes I’ve seen weren’t the result of aggressive planning gone wrong. They were small, quiet errors. The kind that happens when a deadline slips, an election isn’t made, or a form gets overlooked entirely. The tax code is unforgiving in these situations, and the IRS has little sympathy for “I didn’t know.” This article walks through some of the most common, and most costly, small mistakes that can devastate your client’s tax situation, along with practical guidance for avoiding them.

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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

Hobby Loss Regulations And Loper Bright

For me, the most exciting Tax Court opinion of 2025 was Judge Joseph Goeke's supplement to his 2024 opinion in the case of Gary M. Schwarz. With a $1,851,878 tax deficiency, it is the largest hobby loss opinion since 2019. (The really big dollar cases tend to settle.)

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Consult, Don’t Convince: Turning Discovery Calls into Advisory Opportunities

The most successful accountants aren’t the ones who pitch the hardest, they’re the ones who listen the most. When you ask better questions, you can diagnose problems that clients didn’t even know they had, which then helps us clarify outcomes instead of listing services. When we shift from “convincing” to “consulting,” discovery calls stop being “sales” conversations and start becoming advisory conversations. And advisory conversations naturally lead to advisory engagements.

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Contracts, Signing Bonuses, and the Substantial Presence Test

In tighter job markets, recruits are often offered signing bonuses (and sometimes moving expenses) to join a firm. Sometimes construction workers temporarily relocate to jobs in other states while they are employed by the company that hired them in their home state. This article reviews some of the foundational tax concepts to consider when evaluating sourcing of income for state tax purposes.

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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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AI Risk Management Frameworks for Tax Accountants

Let’s be direct: AI is one of the most powerful capacity tools tax professionals have seen in decades. Used correctly, it buys you time you can reinvest into high-value advisory: planning, structuring, audits, negotiations, strategy, client education, and relationship building. But here’s the catch that you as an elite tax practitioner already understand: aggressive planning requires rigorous defensibility. If you’re going to use AI to accelerate complex planning work, your defense file must be stronger, not weaker. This playbook gives you that: a practical framework that keeps you safe while you scale.

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Start the Year Right: Your WISP Doesn’t Have to Be a Tax Season Nightmare

The mere mention of a WISP makes most tax professionals want to suddenly lose their internet connection. It sounds bureaucratic, technical, and deeply unfun. But here’s the good news: creating and maintaining a WISP does not have to feel like a compliance root canal. And ignoring it can turn into something far worse than an IRS audit. Let’s talk about why you need one, what it’s actually supposed to do, and how to get it done without wrecking your sanity in the middle of filing season.

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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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