A year or so after graduating from law school, my husband and I bought a house in Philadelphia. Two years later, we got a dog, which sent me scurrying online to find a dog walker.
My husband had moved over to an AmLaw 200 firm by that point and he was working long hours. I was working for a midsize firm in the city and my hours were just as long. We left home pretty early in the morning and often met to eat dinner out in the City.
We paid someone to clean our house and mow our lawn. We sent out our laundry. And then we were looking for someone to walk the dog. We were outsourcing our lives. And I didn’t want to do that anymore.
So, I convinced my husband to quit his high earning AmLaw job. And I quit my job. And we started our own law firm.
This is not the point where I tell you how everything worked out fine. Because it didn’t. There were a lot of bumps.
Managing your own business is hard. The income is unpredictable. You will make bad decisions. We made bad hiring decisions—including a clerk who used to hide work in a folder and tell us it was done. And we made bad client decisions— including extending credit to a client who was arrested for embezzlement before we got paid.
But we also made great decisions. I loved most of my staff. I kept my own hours. I chose my own clients, and it got a lot easier to say no as we figured things out. And when we had kids, they came to the office which was walking distance from my children’s school—my middle child set up a rival legal advice service in the law firm lobby after school at a very competitive nickel rate.
If you’re a business owner, or if you’ve worked with a business owner, you likely relate to some of my story.
Even though starting and running a small business can be tough, small businesses remain the mainstay of the U.S. economy, creating jobs, millionaires, and in some cases, big companies and billionaires. Diane Hendricks, #1 on Forbes’ new list of America’s Richest Self-Made Women, with a net worth of $22.5 billion, started a roofing supply business with her late husband, Ken, in Wisconsin in 1982. Under her watch, ABC Supply, which she owns and has chaired since Ken’s death in 2007, has grown to more than 900 branch locations and $20 billion in sales.
Today, the U.S. has more than 33 million small businesses, employing nearly 62 million Americans, some 46% of private sector employees. According to the SBA, from 1995 to 2021, small businesses created 17.3 million net new jobs, accounting for 63% of the net jobs created during this period. Underlying that impressive net job growth number, however, are millions of small business births and closures. About one in five of all small businesses fail in their first year and one in two succumb in the first five years.
Our new Forbes Small Business Toolkit aims to help you beat the odds, with information on choosing the right entity, assembling your professional team, filing and paying taxes on time, and managing small business loans. Whether you’re trying to sort out worker classification, figure out how to survive tariffs, or discover the best small businesses to buy now, we’ve got you covered.
One more thing. Tax policy can turn on a dime–that’s been made clear as the House and Senate hashed through the Big, Beautiful Bill. We’re on top of it. With so much uncertainty—and more changes on the way—we suggest bookmarking this Toolkit and checking back for our updates.
Speaking of bookmarking, my stack of books to read keeps piling up, but I’m planning on tackling one this weekend: David Suchet’s Behind The Lens. We’re big Agatha Christie fans in my house and you might recognize the name as the actor who will forever be recognized as Hercule Poirot–it turns out that he’s a history and travel fan like me.
I hope you have something similarly relaxing planned. Enjoy your weekend,
Kelly Phillips Erb (Senior Writer, Tax)
Questions
This week, a taxpayer asked:
I own a business. Can I write off dinner if we talk about business?
Sort of. It’s true that businesses are entitled to a deduction for the costs of meals, but like everything tax-related, there are rules and restrictions.
The business meals deduction is limited to 50% of the meal costs. If that feels smaller than before, it is. During COVID, there was a temporarily enhanced deduction of 100% to support the restaurant industry—that temporary deduction has now expired, and the old rules are back in play.
To be deductible, a meal must be directly related to business, meaning there must be a clear link between the meal and a business activity or purpose. That would apply, for example, to a meeting where you discuss business with a valued client or potential lead. Additionally, either you or an employee of the business must be present when the food or beverages are served—you can’t simply offer a steak dinner and walk away.
And speaking of steak, the costs shouldn’t be lavish or extravagant given the circumstances (context matters).
Finally, to claim a deduction for any business expense, Section 162 of the Tax Code requires that the expense be “ordinary and necessary.” According to the IRS, an ordinary expense is common and accepted in your trade or business. The IRS defines a necessary expense as “one that is helpful and appropriate for your trade or business.” For an expense to be deductible, it needs to be both.
One word of caution: The Tax Cuts and Jobs Act eliminated deductions for most business-related entertainment expenses. This means that expenses like tickets to sporting events, concerts, or clubs are generally not deductible, even if a business purpose exists. However, if meals are provided at the same time, they may be deductible if purchased or billed separately from the entertainment cost.
As always, keep excellent records. When it comes to meals, you’ll want to include the date, total cost (including tax and tip), name of the restaurant, and details of the business meal (who attended and how it related to your business). An easy way to track? Jot those details on the back of the receipt.
Other meal expenses, including food for company holiday parties and food and beverages provided to the public, may be 100% deductible if they qualify for specific exceptions.
If in doubt about whether a meal or entertainment expense might be deductible, ask your tax professional.
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Do you have a tax question or matter that you think we should cover in the next newsletter? We’d love to help if we can. Check out our guidelines and submit a question here.
Statistics, Charts, And Maps (Oh My!)
Foreign investors with assets in the United States often encounter complex estate tax rules that can significantly impact taxation of their U.S. assets at death. If the individual is a non-resident, non-citizen of the U.S., the federal estate tax applies only to assets situated or deemed to be situated within the U.S. (for example, U.S. real property or stock in a U.S. corporation). But the rules can be complex. Understanding how an estate tax treaty may mitigate this tax burden is critical–the U.S. has 15 estate and gift tax treaties with countries worldwide.
Those who are neither U.S. citizens nor residents for estate tax purposes are often surprised by the estate tax rules. Those surprises can include the limited exemption amount, common misconceptions about asset types, the requirement to disclose the value of worldwide assets on their estate tax return, and other pitfalls that can complicate estate planning.
It doesn’t get any easier if you simply give up your citizenship (a la Tina Turner in 2023). In January 2025, the U.S. Treasury issued final regulations on the taxation of gifts and bequests from covered expatriates. These regulations introduced the filing of a new Form 708 to report these transfers-noncompliance subjects the recipients to significant penalties.
Our best advice? If you have questions about your reporting requirements, consult with a tax professional.
A Deeper Dive
As businesses grow, events and circumstances often lead them to consider major changes in their business model. This often results in what’s referred to as a reorganization and includes transactions like mergers and acquisitions, spinoffs and split-offs, and recapitalization.
While there may be many reasons for a company to consider a reorganization, one of the goals is typically a tax-favored outcome. With some planning, a reorganization may be tax-free. A goof, an oversight, or a misstep can result in a big tax bill.
How big? Try $4 billion. That’s how much the IRS assessed in taxes, penalties, and interest on Yum! Brands.
Yum! Brands is the parent company of KFC, Taco Bell, Pizza Hut, and Habit Burger & Grill. The company touts over 61,000 locations in 155 countries. On November 30, 2013, Yum! Brands publicly announced a corporate reorganization. In this reorganization, the company would no longer be broken out into segments based on geography. Instead, it would focus its organization based on brands (i.e., KFC, Taco Bell, and Pizza Hut). It would also have separate divisions for China and India. The goal of this reorganization was to drive growth.
To help facilitate the reorganization, the new subsidiaries issued stock in exchange for stock in the previous subsidiary. This stock for stock reorganization often falls under the section 368(a)(1)(B) of the tax code, which allows for the acquisition of a corporation solely in exchange for all or part of its voting stock. Yum! Brands thought that the conditions under Section 368(a)(1)(B) were met, which would defer the gain, allowing the reorganization to make more sense from a financial perspective.
The IRS disagreed and issued a bill for $4 billion: $2.1 billion in taxes, $418 million in underpayment penalties and over $1.5 billion in interest. The matter has moved to court where it’s expected that many companies and advisors will be focused on the outcome.
Tax Filings And Deadlines
📅 June 16, 2025. Due date for individuals living and working abroad to file their 2024 federal income tax return and pay any tax due.
📅 September 30, 2025. Due date for individuals and businesses impacted by recent terrorist attacks in Israel.
📅 October 15, 2025. Due date for individuals and businesses affected by wildfires and straight-line winds in southern California that began on January 7, 2025.
📅 November 3, 2025. Due date for individuals and businesses affected by storms in Arkansas and Tennessee that began on April 2, 2025.
Tax Conferences And Events
📅 June 16-19, 2025. Latino Tax Fest. MGM Grand Hotel & Casino, Las Vegas, Nevada. Registration required.
📅 June 18, 2025. Avalara CRUSH on Tour. Bridgeport Art Center (Skyline Loft), 1200 W. 35th Street, Chicago, IL 60609. Registration required.
📅 June 26, 2025. Avalara CRUSH on Tour. Iron23 (Flatiron District), 29 West 23rd Street, New York, NY 10010. Registration required.
📅 July 1-September 16 (various dates), 2025. IRS Nationwide Tax Forum in Chicago, New Orleans, Orlando, Baltimore and San Diego. Registration required (discounts available for some partner groups).
📅 July 18-19, 2025. Tax Retreat “Anti Conference.” Denver, Colorado. Registration required.
📅 July 21-23, 2025. National Association of Tax Professionals Taxposium 2025. Caesars Palace, Las Vegas, Nevada. Registration required.
📅 July 22-24, 2025. Bridging the Gap Conference. Denver Marriott Tech Center, 4900 S. Syracuse Street, Denver, Colorado. Registration required.
📅 July 28-30, 2025. Tax Summit 2025. Grand America Hotel, Salt Lake City. Registration required.
Trivia
In 1867, William M. Springer refused to pay the federal taxes he owed, resulting in one of the first tax cases heard by the U.S. Supreme Court. Before the matter went to the Supreme Court in 1874, how did the government collect the tax due?
(A) The government seized Springer’s property and sold it at auction.
(B) The government seized Springer’s bank account.
(C) The government required Springer to work for the government for free for one year.
(D) The government didn’t collect it at all.
Find the answer at the bottom of this newsletter.
Positions And Guidance
The IRS issued its annual Data Book detailing the agency’s activities during fiscal year 2024. This year’s edition marks the publication’s 30th anniversary—the first Data Book covered fiscal years 1993 and 1994 and was available in 1995. The Data Book provides a statistical overview of the agency’s operations for the fiscal year, including returns received, revenue collected, taxpayer services provided, tax returns examined (audits), efforts to collect unpaid taxes, and other details about the work of the IRS.
The IRS published Internal Revenue Bulletins 2025-23 and 2025-24.
The American Bar Association Section of Taxation sent a letter to the IRS providing recommendations for the 2025-2026 Priority Guidance Plan. Each year, the Treasury and the IRS use the Guidance Priority List to identify and prioritize tax issues that should be addressed through regulations, revenue rulings, revenue procedures, notices, and other published administrative guidance.
The U.S. Tax Court will begin accepting applications for the November 5, 2025, examination for nonattorney application for admission to practice before the Court on July 14, 2025. All applications must be completed electronically on the Tax Court’s website.
Noteworthy
Business executives’ view of the economy continued to sour amid recession fears and uncertainty about tariff impacts, according to the second-quarter AICPA and CIMA Economic Outlook Survey. The survey polls chief executive officers, chief financial officers, controllers and other CPAs in U.S. companies who hold executive and senior management accounting roles.
New estimated data from the National Student Clearinghouse Research Center shows a 12% increase in spring 2025 undergraduate accounting enrollment compared to the prior year. This marked the third consecutive semester of growth in accounting enrollment across all undergraduate institutions, regardless of type. It was the second consecutive semester of double-digit percentage increases. Accounting enrollment increased at a higher rate than overall business enrollment.
McCarter & English announced that trusts and estates attorneys Jill Lebowitz and Abbey Horwitz have joined the firm’s Tax, Employee Benefits, Trusts, Estates & Private Clients practice group in the Newark office. Lebowitz joins as a partner and Horwitz as special counsel, both arriving from Coughlin Midlige & Garland LLP.
Pennsylvania State Representative Joseph D’Orsie (R-47 has proposed the repeal of the Johnstown Flood Tax. The Johnstown Flood Tax, originally intended to help rebuild the city of Johnstown after a 1936 flood that devastated the town. The tax—an 18% tax on liquor sold in Pennsylvania—is still in place today. The money goes to the Commonwealth’s General Fund.
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Trivia Answer
The answer is (A). The government seized Springer’s property and sold it at auction.
In January 1867, after Springer refused to pay the $5,279.78 owed (including tax and penalty), the tax collector levied property in Springfield, Illinois, that Springer owned. The property was advertised and sold at public auction on March 15, 1867.
The matter eventually landed in the U.S. Supreme Court (Springer v. U.S.), with Springer claiming that the tax was a direct tax and therefore unconstitutional, and that the seizure and sale of his property deprived him of his property without due process of law. The Supreme Court rejected both arguments and affirmed the federal government’s power to levy and collect income taxes, including through the seizure and sale of property.
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