Artificial Intelligence (AI) continues to impact all industries as companies and individuals try and find the perfect balance between automation and sufficient oversight and monitoring. Tax reporting would appear, on its face, to be a prime candidate for the promises of efficiency achieved through AI’s streamlined review of large amounts of data and identification of potential errors or inconsistencies. The Internal Revenue Service (IRS) already uses AI to select individuals and partnerships for audit, identify fraud, and other compliance and enforcement functions. I’ve previously written about the IRS’ historical struggle with auditing partnerships and the future of partnership enforcement, which…

Tax touches so many parts of our lives—even in the movies. On May the 4th, it seems fitting to focus on tax themes and consequences in the original “Star Wars.” Well, it’s the original to me—you might know it as “Star Wars: Episode IV – A New Hope” (1977). (A quick note: My review is based on U.S. law as it might apply to the Rebels. Additionally, although I’m sure that Congress would love to tax droids and space aliens, they haven’t found a way to do it just yet. For tax purposes, I treat the droids as computers (good)…

I am one in 33,185,550. That is, give or take a few thousand, the number of small businesses in the United States. According to the U.S. Small Business Association (SBA), small businesses—those with fewer than 500 employees—employ 61.7 million Americans, nearly half of private sector employees. And, from 1995 to 2021, small businesses created 17.3 million new jobs, accounting for 62.7% of net jobs created since 1995. For over 60 years, the SBA has observed National Small Business Week to celebrate small business owners. This year, National Small Business Week 2025 will take place May 4-10. The IRS will also…

A Washington D.C. bill is the latest to hit back at credit card swipe fees. The Fair Swipe Act of 2025, introduced by D.C. Councilmember Charles Allen, would prevent banks and credit card companies from collecting processing fees on sales tax and gratuities—charges that businesses don’t even keep. Increasingly, Americans like reaching for plastic to pay bills. A study by the Federal Reserve Bank of Atlanta indicated that, as a share of all payments by number—including bills, purchases, and person-to-person (P2P) payments, made in person or remotely—more were made by credit card (32%) than other forms of payment (debit cards…

In the latest chapter of the Trump versus Harvard saga, Trump has double-downed on his threats to revoke Harvard’s tax-exempt status. As I previously reported in Forbes, the tax-exempt status for a university at the scale of Harvard is worth billions of dollars over the span of Trump’s four-year term. However, a natural question arises over whether Trump can even take these actions against Harvard? How Does Harvard Save Money As a Tax-Exempt Organization? There are three direct ways a university with a tax-exempt status can save significant money: The university does not have to pay taxes on the growth…

Tax season isn’t over just yet. Tax-exempt organizations with a calendar year-end (December 31) must file a return or request an extension by May 15, 2025. Due Dates The annual filing due date for the Form 990-series (Forms 990, 990-EZ and 990-PF, Form 990-N (the e-postcard), Form 990-T and Form 4720 are normally by the 15th day of the 5th month after the end of the accounting year. For an organization with a December 31 year-end, that’s May 15. Other organizations may need to do a little math. Extensions Tax-exempt organizations that need extra time to file can request a…

In April 2025, Arkansas became the first that taxes income to exempt NIL income from taxation. Questions arise about why they did this and whether more states will follow their lead. The Taxation of NIL Income According to On3, Arch Manning has a name, image, and likeness (NIL) valuation of $6.5 million. Meanwhile, Athlon Sports reports heralded basketball player PJ Haggerty is requesting a $4 million NIL deal in the transfer portal. The NIL money that the current group of college players demands is growing at a staggering rate, and their net take-home pay may be getting bigger as many…

By 2021, over 80 percent of businesses had adapted to digitization but, as a Deloitte study reported, as of February 2025, nearly 75 percent of family offices are underinvested or minimally invested in technology. This dichotomy means that while a multinational business may be thriving, a family’s wealth, especially when tied to such a business ownership may be at risk of partial and perhaps, complete loss in succession without innovation. As global markets adapt rapidly to technological changes and economic shifts, family-held businesses are at risk of becoming obsolete and the succession of the family’s wealth disappearing. Traditional estate planning…

When a person dies in the US or as a US citizen, anywhere, an often lengthy estate administration process begins to transfer the assets of the decedent to their heirs or other beneficiaries. Estate administration addresses the resolution of the transfer of assets both in and out of probate. Probate is the process to transfer assets to heirs and beneficiaries regardless of whether the decedent died with a Last Will and Testament. Therefore, the administrator of the estate, usually an executor or personal representative must clear all debts of the decedent, file all taxes, and administer all assets properly to…

The Trump administration’s aggressive and wide-ranging economic policy changes during his first 100 days, especially historically high tariffs coupled with a confrontational negotiating stance towards trading partners, is fueling an intense debate among economists. Is there a master plan at work, and we just need to be patient? Or do Trump’s policies lack a coherent strategy, and risk both short and long-term economic damage? Trump’s Case For A Strategy President Donald Trump, and his economic advisors, argue there’s a strategy. This is the so-called “Mar-A-Lago” agreement, and it has four key elements. First, high tariffs will reduce the U.S. trade…