CURRENT EDITION

Help Your Clients Implement a Fortune 500 CFO Strategy
For decades, some of America’s largest corporations have used a financial strategy that gives their CFOs greater control over insurance costs, helps them finance risks the commercial market handles poorly and creates an opportunity to retain underwriting profit when losses come in below expectations. Approximately 90% of Fortune 500 companies have captive insurance subsidiaries.¹ Historically, the economics favored organizations with substantial capital, large insurance programs and the resources to support their own insurance operations. Small and midsize businesses rarely had the scale to justify the cost and complexity. That equation has changed. A mature network of specialized insurance professionals and structures now allows qualifying privately held businesses to pursue many of the same risk-financing advantages. Federal tax law can further improve the economics for certain smaller insurance companies. For CPAs and tax professionals, this creates an advisory opportunity. The challenge is recognizing which clients could benefit and what conditions must exist before recommending it.
READ MOREThe Rise of Post-Cognitive Tax: Unlocking Enterprise Potential: How Post-Cognitive Accountants Transform Business Tax Forms into Strategic Masterpieces
In the transformative landscape of 2027, the role of the accountant has transcended traditional boundaries. With Artificial Intelligence (AI) shouldering the burden of routine calculations and compliance checks, the Post-Cognitive Accountant emerges as a strategic visionary. No longer confined to the mechanics of number crunching, these professionals reimagine business tax forms—such as the Form 1120 for corporations—into dynamic portals that unlock untapped enterprise potential. Let's embark on an exploratory journey through a corporate tax return, revealing how each line item becomes a gateway to innovation, growth, and holistic success.
Read MoreWhat You Need to Know About the Proposed Trump Savings Accounts
Tucked inside the narrowly passed “One Big Beautiful Bill Act,” President Trump’s sweeping tax and spending package, is a provision that’s drawing media attention: the creation of a new tax-deferred investment account called a Trump Account. A proposed $1,000 “baby bonus” tied to the account only adds to the intrigue. While the reconciliation bill primarily focuses on extending the 2017 tax cuts and reshuffling federal spending priorities, this unexpected addition could offer new planning opportunities for taxpayers.
Read MoreFreelancer Deductions: What You Might Be Missing and What You Need to Remember
Even savvy freelancers often miss deductions that could significantly reduce tax liability. The IRS offers legitimate ways for freelancers to deduct business-related costs, but it’s not always obvious which expenses qualify and which ones cross the line into nondeductible territory. This confusion is made worse when we see some of the terrible advice from so-called “experts” on social media. In this article, we’ll explore the most commonly missed deductions for freelancers, highlight real-world examples, and review what tax professionals need to keep in mind when advising these clients.
Read MoreHow to Help Your Clients Maximize College Financial Aid
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.
Read MoreThe Rise of Post-Cognitive Tax Accounting: Embracing a New Frontier in 2027 (or Sooner!)
The year is 2027, and the landscape of tax accounting has undergone a dramatic transformation. Artificial Intelligence (AI) has automated many traditional tasks once considered the bedrock of the profession. Yet, contrary to fears of widespread job losses among tax preparers, this technological revolution has ushered in a new era – Post-Cognitive Tax Accounting. This paradigm shift is redefining the role of tax professionals, opening opportunities to explore uncharted territories that leverage human intuition, creativity, and strategic insight.
Read MoreTAX COURT ROUNDUP – May 2025
Once again, Tax Court provides slices of life as well as hyper-technical drilldowns into convoluted legal conundrums. To any who say that tax law is dull, I refer them to the annals of 400 Second Street, NW, where anything goes.
Read More2025 Summer Education Series Event Calendar
We are thrilled to bring you the 2025 Summer Education Series, sponsored by Vistia! All summer long we will be bringing our loyal subscribers monthly webinars featuring some of the brightest minds in tax. Each webinar will feature our usual blend of high-quality education and entertainment and include continuing education credits for those who qualify. All of this is included in your regular subscription! Continue reading to see what we have in store...
Read More2025 Spring Fling Webinar Event
As we prepared our 4th Annual Summer Education Series, our friends at Sandy Bay challenged us to go bigger and do even more live events than we originally planned. So, we did! We are proud to present Think Outside the Tax Box's first ever “Spring Fling” live webinar event. As a monthly or annual subscriber, this webinar is 100% exclusive, and free to you! Every webinar comes with free continuing education credits for those who qualify! Keep reading for more details...
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CURRENT EDITION

Help Your Clients Implement a Fortune 500 CFO Strategy
For decades, some of America’s largest corporations have used a financial strategy that gives their CFOs greater control over insurance costs, helps them finance risks the commercial market handles poorly and creates an opportunity to retain underwriting profit when losses come in below expectations. Approximately 90% of Fortune 500 companies have captive insurance subsidiaries.¹ Historically, the economics favored organizations with substantial capital, large insurance programs and the resources to support their own insurance operations. Small and midsize businesses rarely had the scale to justify the cost and complexity. That equation has changed. A mature network of specialized insurance professionals and structures now allows qualifying privately held businesses to pursue many of the same risk-financing advantages. Federal tax law can further improve the economics for certain smaller insurance companies. For CPAs and tax professionals, this creates an advisory opportunity. The challenge is recognizing which clients could benefit and what conditions must exist before recommending it.

Structured Installment Sales Making Comeback – How Good A Tool Is It?
Structured Installment Sales (SIS) have been making a comeback. Historically low interest rates starting in 2011 made them go out of favor. Starting in 2018, insurers started coming back into offering them. MetLife expanded its SIS solution to 49 states, Puerto Rico and D.C. in 2022. You need to know about SIS and it deserves a place in your toolbox. You might not be using it as often as the toolmakers imply. I took a look at SIS in 2023 and was a little more enthusiastic about it than I am now. Let’s dig in.

Assessment Statutes and Document Retention Best Practices
When it comes to document retention, my guiding policy is “If I don’t keep it, it can’t be stolen or subpoenaed.” That sounds cynical, but there’s truth in it. The smaller your data “surface area,” the less you have to manage in the event of a data breach (or, if you hold paper documents, in the event of a fire or break in). And, if a client or former client gets really sideways in divorce or criminal court, being able to say “I have a policy in place and I don’t keep records longer than three years” can provide you with a measure of peace. But what should your policy be? It depends, but relevant assessment statutes are a good place to start. This article reviews the IRS rules for assessing tax and provides some best practices for developing document retention policies for return preparation documents in your practice.








