Self-Employed Health Insurance Basics

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A single medical bill can wipe out your profits. But health expenses don’t have to drain your cash flow. 

In this episode, you’ll learn three powerful ways to turn your medical costs into legitimate tax deductions. From self-employed health insurance and Health Savings Accounts (HSAs) to Section 105 reimbursement plans and employee health benefits, these strategies can help business owners save thousands while staying fully IRS-compliant.

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Chapters

(00:00) Turning Health Costs Into Tax Savings
Health expenses can become powerful deductions when structured properly. Learn how small business owners can legally reduce taxes through insurance, HSAs, and reimbursement plans.

(00:45) Self-Employed Health Insurance Deduction
How sole proprietors, LLCs, and S Corp owners can claim health insurance premiums as deductions, and the exact steps S Corp owners must follow to stay compliant.

(04:03) The Triple Tax Benefit of HSAs
How Health Savings Accounts offer tax-free contributions, growth, and withdrawals, and why treating your HSA like a retirement account can build long-term wealth.

(08:28) Section 105 Medical Reimbursement Plans
For business owners with high out-of-pocket medical costs, this plan turns personal medical expenses into deductible business costs when set up correctly.

(10:11) Health Benefits for Employers
Affordable options for small businesses to offer tax-free health reimbursements through QSEHRA or ICHRA plans without the complexity of traditional group insurance.

(13:06) The Four Keys to Health Tax Strategy
How to combine these tools: Insurance deductions, HSAs, Section 105 plans, and employee benefits, to lower taxes and protect your cash flow.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
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🎙 ABOUT THE PODCAST
The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.