HSAs After Death: What You Need to Know
Health Savings Accounts (HSAs) are a great way to save money. Unlike any other tax-advantaged account, they provide a triple tax benefit: Contributions are tax-deductible. Monies inside the HSA grow tax-free Withdrawals are tax-free if used for medical expenses. Withdrawals after age 65, if not used for medical expenses, are subject to regular income taxes. […]
Lawyer Burned by Fake AI Tax Cases—Don’t Be Next
Artificial intelligence (AI) is all the rage today. AI tools like ChatGPT, Claude, Grok, and Perplexity are being used for everything, including legal research. But beware! AI is not perfect. It’s not even intelligent. AI doesn’t think like a human, and it has no internal fact-checker. It produces new content by analyzing vast amounts of […]
Do You Need a W-2 for Spouse-Employee 105-HRA Benefits?
If you employ your spouse in your business and use a Section 105-HRA to deduct family medical expenses, you may be wondering whether issuing a W-2 is necessary. The good news from a tax law standpoint, a W-2 is not required. IRS guidance and court decisions confirm that medical reimbursements under a properly structured Section […]
A Little-Known Way to Pay Family and Save on Taxes
Many business owners overlook a powerful strategy that allows them to pay family members, reduce taxes, and avoid payroll taxes altogether. You likely know the traditional approach: hire your child and put them on payroll. That strategy works well for younger children in a sole proprietorship. But once your child turns 18—or if you operate […]
$12,000 Door Replacement: Repair or 39-Year Asset?
When a five-figure commercial building expense hits your desk, the first question is simple: Can you deduct it, or must you depreciate it over 39 years? Consider a recent example. An office building owner replaced a failed sliding glass door and frame at a total cost of $12,000, including removal and installation. The new unit […]
Late Filing Costs Estate $1.5M—Will Yours Be Next?
With today’s $15 million federal estate and gift tax exemption ($30 million for married couples), it’s easy to believe estate tax planning is no longer a concern. But a recent Tax Court case proves otherwise—an estate lost $1.5 million simply because a portability election was not properly and timely filed. Here’s the key issue: When the […]
The Hidden Benefits of Filing a Gift Tax Return
The givers of gifts (donors), not the recipients (donees), file gift tax returns. If you give money or property, you may be legally required to file a gift tax return with the IRS—even if you owe no gift tax. In fact, most people who file gift tax returns do not pay any gift tax because […]
2025 Last-Minute Year-End Tax Strategies for Your Stock Portfolio
When you take advantage of the tax code’s offset game, your stock market portfolio can represent a little gold mine of opportunities to reduce your 2025 income taxes. The tax code contains the basic rules for this game, and once you know the rules, you can apply the correct strategies. Here’s the gist: Avoid the […]
OBBBA Revives Your Ability to Kill Capital Gains with QOFs
Since 2018, taxpayers have enjoyed significant tax benefits by investing capital gains in Qualified Opportunity Funds (QOFs). QOFs channel money into Qualified Opportunity Zones (QOZs)—government-designated low-income census tracts. Investors have embraced the program, pouring in more than $160 billion. The program was set to expire in 2026. However, the One Big Beautiful Bill Act (OBBBA) […]
Beat the OBBBA/TCJA Rules That Punish Dog Breeding Hobbies
Are you involved in a dog breeding business or considering starting one? If so, you are in the IRS’s crosshairs. The IRS has long considered dog breeding to be an activity typically classified as a hobby, rather than a business, for tax purposes. When it comes to taxes, hobbies are usually tax disasters. Unlike a […]
What Most People Get Wrong About Taxes — And What to Do Instead
Most people misunderstand taxes in ways that can cost them significantly. Here are common misconceptions and what you should do instead to optimize your tax outcomes. What Most People Get Wrong About Taxes Tax Planning Is Only for the Wealthy or Big Businesses Many small business owners and freelancers believe tax planning doesn’t apply to […]
Vehicle Used for Business Can Produce a Big Surprise Deduction
If you’ve used your personal vehicle for business—whether you’re a sole proprietor or you received mileage reimbursement from your S or C corporation—there may be a valuable tax deduction waiting for you. When you use the IRS standard mileage rate (or when your corporation uses it to reimburse you), the mileage rate is not just […]