CURRENT EDITION

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.
READ MORESome Tips to Help Clients Make the Most of the New Tip Tax Deduction
The One Big Beautiful Bill Act relieves some of the tax burden that comes along with tip income for tax years 2025-2028. But not in some of the ways that it was initially explained. Yes, tip income is still taxable income. No, customers do not have to pay tips in cash for them to be deductible. But the tip does have to be voluntary, qualified, and reported to the IRS.
Read MoreTurning Extra Hours into Extra Cash: What You Need to Know about Overtime and the OBBBA
Do you love giving your clients great news? I do. Especially when it is about a tax benefit they can receive as the result of the hard work that they have put in throughout the tax year. That is what the overtime deduction is for the taxpayer. A little bit of tax relief for their hard work. But before sharing the good news with them, we need to make sure that we understand that No tax on overtime is not a blanket statement that will apply to all overtime compensation and all taxpayers. It is our responsibility to do our due diligence to understand who it will impact and how.
Read MoreDeducting Gambling Losses: Part 1 (OBBBA Updates)
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 1of this two-part article we will discuss deducting gambling losses for recreational and professional gamblers. We will also discuss additional deductions professional gamblers can take and how they were affected by the OBBBA.
Read MoreTAX COURT ROUNDUP – August 2025
This month's Tax Court cases feature warnings to lawyers (and appraisers?) in the ongoing syndicated conservation easement wars; teasers about the impact of Loper Bright Ent. and Section 7701(o)(1); useful practice tips, and the conclusion of Boechler, P.C. (equitable tolling won't save a losing case).
Read MoreThe Think Outside the Tax Box OBBBA Quick Reference Guide
The One Big Beautiful Bill Act (OBBBA) marks the most sweeping overhaul of the tax code since 2017, reshaping rules across personal and business income, education, healthcare, and credits. To help you stay ahead of the curve, Think Outside the Tax Box is proud to share our Quick Reference Guide, designed to keep you and your clients informed, prepared, and proactive.
Read More5 Keys to Maximizing the SALT Changes
The Senate just passed the most significant SALT deduction changes since 2017, and most tax professionals are missing the real opportunity. While everyone's celebrating the increase from $10,000 to $40,000, there's a hidden tax trap that creates effective marginal rates exceeding 45% -- and that's your biggest planning goldmine.
Read More460(e) – Leveling the Playing Field for Construction
Buried in the middle of the One Big Beautiful Bill Act (OBBBA) is a small section with huge tax savings for multifamily developers – expansion of the 460(e) revenue recognition method exceptions. Previously only available to smaller construction contractors, the new law opens up a potential windfall for larger scale developers.
Read MoreEverything Old Is New Again: In Many Ways OB3A Is a Return To Obamacare 1.0
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 article 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.
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CURRENT EDITION

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.

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.)

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.








