Turning a passion project or freelance gig into extra cash is a classic move, but it comes with a major compliance hurdle. Whether you are selling digital products online or picking up local client work, the IRS demands that you report every single dollar of that income. However, whether you can deduct your expenses depends entirely on whether the tax collector views your side hustle as a legitimate business or just a hobby.
IRS Eases Partnership Sale Reporting Rules
Final regulations released by the IRS stipulate that partnerships no longer need to provide detailed gain and loss information to selling partners by January 31. This deadline had become a contentious issue.
Simple Retirement Solutions for Small Business Owners
Offering employees retirement options can be an effective way for small business owners to attract and retain talent. If you’re concerned about cost and administrative complexity, you’re not alone. Fortunately, several options are available, including a Simplified Employee Pension (SEP) plan.
Backup Withholding: What Businesses Should Know
In most cases, you aren’t required to withhold taxes from payments to independent contractors. However, there are situations in which the “backup withholding” rules apply. Backup withholding is most commonly required when a contractor fails to provide a correct Social Security number or Employer Identification Number, or doesn’t properly complete Form W-9, “Request for Taxpayer Identification Number and Certification.”
Guide to Rising ACA Employer Mandate Penalties in 2026
Many small businesses operate under the assumption that they do not have enough workers to worry about the “play-or-pay” provisions of the Affordable Care Act (ACA). However, as a business expands, these rules can apply much sooner than expected.
A common misconception contributes to this blind spot: the belief that the repeal of the individual mandate penalty under the Tax Cuts and Jobs Act applied to businesses as well. While the individual mandate penalty for citizens was eliminated, the employer shared responsibility rules remain fully in effect and heavily enforced.
Small Business Tax Thresholds and IRS Accounting Exemptions
Although your company may feel expansive to you, you might wonder how the federal government officially classifies it for tax purposes. If your organization qualifies as a small business, you can lock in several critical tax advantages.
However, the specific rules for individual tax provisions vary. Depending on your exact operational size, you might be eligible for some small-business breaks while being excluded from others.
Strengthen Your Benefits Package with Educational Assistance
If your business is like many today, you’re seeking more ways to attract and retain talent. One option is to offer tax-advantaged educational assistance under Internal Revenue Code Section 127. Recent legislative changes have expanded the value of this benefit.
Reducing IRS Audit Risk for Small Businesses
When business owners think about risk, they often focus on market pressures or operational challenges. An IRS audit usually isn’t top of mind — but it can be costly, disruptive and time-consuming. Although some taxpayers are randomly selected for an audit, many audits occur because the IRS has identified certain patterns or inconsistencies. Understanding where these risks typically arise can help you limit your business’s exposure.
Layoff Alternatives: Strategies to Reduce Costs and Retain Talent
Laying off staff is every business owner’s least-favorite task. While reducing your workforce can restore short-term stability, it often comes with hidden long-term costs: severance pay, legal fees, loss of institutional knowledge, and the massive expense of rehiring when the economy rebounds.
A Guide to Maximizing Tax-Free Gains with QSB Stock and OBBBA
If you operate your business as a C corporation, you may be sitting on one of the most powerful wealth-building tools in the Internal Revenue Code: the Qualified Small Business (QSB) stock exclusion. Historically known as Section 1202, this provision allows founders and investors to exclude significant portions of their capital gains from federal income tax.