416 \\ Self Employed Health Insurance Deduction: How It Works for S Corps & Sole Props episode artwork

EPISODE · Aug 7, 2026 · 14 MIN

416 \\ Self Employed Health Insurance Deduction: How It Works for S Corps & Sole Props

from SMALL BUSINESS FINANCE – Your Guide to Business Tax Planning & CPA Tax Advice · host Tiffany Phillips, CPA & Small Business Tax Strategist

One business owner paid $21,600 a year for family health insurance. He thought he was getting the tax deduction—but a simple S corporation reporting mistake cost him about $7,000 a year. In this episode, Tiffany explains how the self-employed health insurance deduction really works. You’ll learn why the rules change for sole proprietors, partners, and S corporation owners. You’ll also discover three traps that can erase the deduction, including low earned income, access to an employer health plan, and missing W-2 reporting. These practical tax tips can help you improve your tax planning and avoid leaving valuable tax savings on the table. Tiffany also explains why this deduction lowers income tax but not self-employment tax. If you pay for your own health insurance, listen now—before another tax year slips away. Next Steps: 💰 Start Paying Less in Taxes – Grab a Copy of Your Biggest Expense! ➡️https://tiffanyphillips.samcart.com/products/your-biggest-expense-bundle ☎️ Find Out How Much You’re Overpaying the IRS – Book a Free Discovery Call ➡️https://calendar.phillipsbusinessgroup.com/tax 📧 Questions? Email Me at [email protected] ✅ Like and Rate us for more practical tax saving tips... Keep More! 👉 Want me to break down how to deduct your own coverage and stack what you keep? Comment “KEEP” and I'll help you figure it out!

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416 \\ Self Employed Health Insurance Deduction: How It Works for S Corps & Sole Props

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This episode was published on August 7, 2026.

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