1099 Rules for Small Business Owners: Who Needs One, Deadlines, and Penalties
Every January, small business owners trying to follow 1099 rules for small business owners run into the same confusion. Who needs a 1099? Which form do I send? What’s the deadline? What happens if I missed something? 1099s are one of those tax requirements that feel simple until they suddenly aren’t. And when they’re done […]
The Biggest Tax Planning Mistake Business Owners Will Regret in 2026
The biggest tax planning mistake business owners make is assuming tax strategy happens automatically. This tax planning mistake shows up when business owners know the rules but never implement them correctly, especially with retirement tax planning and self-directed IRAs. Many business owners believe their tax planning is handled because they have discussed deductions, entity structure, […]
Top Tax Mistakes New Business Owners Make and How to Avoid Them | Q&A
Tax mistakes new business owners make are almost always preventable. Most first-year entrepreneurs do not realize how 1099 income works, when an LLC matters, how Schedule C affects their taxes, or how deductions like the home office and Augusta Rule actually apply. These early misunderstandings lead to higher tax bills, missing deductions, and avoidable IRS […]
Small Business Year-End Tax Planning: The Ultimate 2025 Guide
Small business year-end tax planning is your last chance to lock in major savings before December 31. This guide covers the S Corp steps, deductions, AGI strategies, and timing rules that matter now. Before December 31, your small business year-end tax planning should focus on… The Three Things Every S Corp Owner Must Do […]
How to Write Off Equipment | Bonus Depreciation and Section 179 Explained
Are you quietly losing money every time you buy equipment? Not because of your purchase, but because you’re using the wrong deduction method? Most business owners assume they have to depreciate items slowly, but they don’t. The rules are much more flexible than people think. With the new 100% bonus depreciation, updated Section 179 limits, […]
How This Seven Figure S-Corp Still Overpaid $30,000 in Taxes
Most S Corp owners follow the right steps, but still pay more tax than they should. A business earning over 300K can lose thousands simply by underusing core strategies. In this live case study, Mike Jesowshek, CPA, reviews a seven-figure business with an S Corp structure, a salary in place, and a record year of […]
How to Hire Your Kids and Save Thousands in Taxes
One of our TaxElm members gave his three teenage sons their first paychecks. Not as an allowance, but as real employees of his business. That one decision saved him over $12,000 in taxes that year, and it’s totally legal. Most business owners don’t realize the IRS allows them to legally pay their children and take […]
The Augusta Rule | How to Rent Your Home to Your Business Tax-Free
Small business owners don’t realize the IRS gives them a legal way to move money from their business to their personal account completely tax-free. It’s called the Augusta Rule, also known as the 14-Day Home Rental Rule. When set up correctly, it is one of the simplest and most powerful ways to reduce your taxable […]
How to Reimburse Yourself Tax-Free with an Accountable Plan
A lot of small business owners pay for expenses out of pocket without realizing there’s a smarter way to handle it. If you’ve ever paid for your phone bill, home office, or business travel personally, you can get reimbursed for those costs, completely tax-free. That’s what an Accountable Plan does. It’s an IRS-approved way for business owners […]
How to Turn Your Medical Bills Into Tax Deductions
A surprise medical bill can wipe out your profits in an instant. But it doesn’t have to. This article covers powerful legal tax strategies that small business owners can use to turn medical expenses into a deductible asset. By the end, you will know exactly which moves to make, whether you are a solo entrepreneur […]