Business Strategies Archives - Think Outside the Tax Box
By Peter J Reilly CPA

IRS And Courts Have Wisdom to Offer Startup Businesses

There is a wealth of business wisdom in a fairly unlikely area. All the businesses involved lost money, sometimes enormous sums. The source is the litigation and regulation around Code Section 183 of the Internal Revenue Code – Activities not engaged in for profit. In order to deduct those losses against other income, taxpayers need to convince the IRS or the court that they had an honest objective of making a profit. The determination of whether an activity is carried on for profit is made by reference to objective standards. Is it possible that following those standards might contribute to you being profitable? It’s worth thinking about.

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Is It Time to Hire in Your Firm?

After my second busy season as a solo practitioner, I made a terrible mistake within my firm. I hired my first employee. As a matter of fact, I hired someone who also had tax and accounting experience. You may be thinking, “What? Hiring is the solution if you were feeling overwhelmed.” That is true, if you are assuming that I had the proper systems in place. The mistake I made was hiring an employee before I was ready. The money was there and ready. The work was there and ready. It only took a few weeks to realize that I didn’t have a capacity issue. I had a systems and processes issue. I am not suggesting that you should work yourself to full capacity, absolutely not. I am suggesting that before you attempt to pass along a task to someone else or put in place automation that you have a written-out process.

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You Don’t Need a Bigger Stack — You Need a Better Portfolio

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. A portfolio recognizes reality: tools don’t have to talk to each other perfectly. They just need to work for you. So let’s explore how to build a smart, efficient, and secure tech portfolio that helps you thrive whether you’re a solo professional or managing a growing team.

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Tracking and Measuring Your Business Development Efforts: KPIs for CPAs

As CPAs, we were trained to work with precision, accuracy, and strategy in everything we do. However, business development has not been part of our standard training; therefore, many accounting professionals not only struggle with business development tactics but also shy away from tracking and measuring the impact of their efforts. But here's the truth: Just as we track and measure other financial data, it is essential to measure business development efforts in order to improve. You can unlock significant growth in your firm by understanding which key performance indicators (KPIs) to track, how you manage your practice, how you acquire new clients, and how to increase your revenue.

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Vibe Preparing: Ignoring Partnership Agreement Impacts on K1s

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.

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A Tax Tailored for Twenty-Six: OBBBA’s Impact on College Endowments

Chapter 4 of the One Big Beautiful Bill (OBBBA) is titled “Investing In American Families, Communities.” Subchapter B of Chapter 4 is “Permanent investments in students and reforms to tax-exempt institutions.” That is where you will find “Modification of excise tax on investment income of certain private colleges and universities.” What is really amusing about this rewrite of IRC Section 4968 “Excise tax based on investment income of private colleges and universities” is that it applies to such a small number of institutions that you can identify them with a decent degree of certainty from publicly available information. The tax does not apply to state universities.

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Data-Driven Sales for Accountants: How to Use Analytics to Identify Sales Opportunities

As accountants, we are no longer just the stewards of our clients' books; we're their trusted advisors, guiding them to financial success, helping them optimize performance, and keeping them compliant with tax regulations. We use data analytics tools to guide and advise our clients to make informed decisions. However, we sometimes overlook using the same tools to advance our practices. We can leverage analytics tools to unlock new sales opportunities, offer enhanced services, and build deeper client relationships. Data-driven sales is a strategic approach to growing your practice consistently, boosting client satisfaction.

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Deducting 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.

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The 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.

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