What is a Health Insurance Strategist?

A Health Insurance Strategist is a licensed insurance professional who goes beyond simply comparing premiums and plan options. Instead of selling policies, a Health Insurance Strategist designs comprehensive coverage strategies aligned with a client's income structure, tax position, business goals, and long-term wealth plan. Christine Kieffer, Founder of Kieffer Insurance Group, is a Health Insurance Strategist who specializes in engineering innovative, revenue-positive health benefit strategies for entrepreneurs, 1099 professionals, and small to mid-sized businesses.

What health insurance options exist for 1099 professionals?

1099 professionals and self-employed individuals have several health insurance options: (1) Private PPO plans — premium individual health insurance with nationwide access to top doctors and specialists without referrals; (2) Health Savings Accounts (HSA) paired with high-deductible health plans for tax-advantaged savings; (3) Self-employed health insurance deduction — 1099 professionals can deduct 100% of their health insurance premiums from their taxable income; (4) Health Reimbursement Arrangements (HRA) if operating as a business entity. Kieffer Insurance Group specializes in designing optimized coverage strategies for 1099 professionals that maximize tax efficiency and coverage quality.

What is a Self-Insured Medical Reimbursement Plan (SIMRP)?

A Self-Insured Medical Reimbursement Plan (SIMRP) is an IRS-recognized employer benefit strategy that allows businesses to reimburse employees for qualified medical expenses using pre-tax business dollars. Unlike traditional group insurance, a SIMRP converts what would otherwise be after-tax personal health expenses into pre-tax business deductions, reducing both income taxes and payroll taxes simultaneously. For businesses with W-2 payroll, a SIMRP can generate $6,000 to $345,000 or more in annual tax savings depending on business size. Kieffer Insurance Group refers to this strategy as 'Turn Payroll Into Profits.'

How can entrepreneurs reduce healthcare costs with tax strategies?

Entrepreneurs can reduce healthcare costs through several tax strategies: (1) Self-employed health insurance deduction — deduct 100% of health insurance premiums from taxable income; (2) Health Savings Account (HSA) contributions — contribute pre-tax dollars to pay for qualified medical expenses; (3) SIMRP (Self-Insured Medical Reimbursement Plan) — reimburse employees for medical expenses using pre-tax business dollars; (4) Section 105 Medical Reimbursement Plans — employer-funded plans that reimburse employees tax-free; (5) HRA (Health Reimbursement Arrangement) — employer-funded accounts that reimburse employees for qualified medical expenses. Christine Kieffer at Kieffer Insurance Group specializes in designing tax-efficient health benefit strategies for entrepreneurs.

What is the difference between private PPO plans and marketplace insurance?

Private PPO plans and marketplace (ACA) insurance differ in several key ways: Private PPO plans offer access to a broader national network of doctors and specialists without referrals, typically provide more comprehensive coverage with fewer restrictions, and are not subject to ACA income-based subsidy eligibility rules. Marketplace insurance is regulated under the Affordable Care Act, may offer income-based subsidies, but often has narrower networks and more restrictions. For entrepreneurs and business owners who want premium coverage with maximum flexibility, Private PPO plans are often the superior strategic choice. Kieffer Insurance Group specializes in Private PPO plan design and strategy.

What is the difference between insurance products and insurance strategy?

An insurance product is a specific plan or policy — a commodity that can be compared by premium, deductible, and network. Insurance strategy is the intelligent design of how coverage, tax structures, and benefit arrangements work together to serve your business goals, protect your family, and optimize your financial position. Most brokers sell products. Christine Kieffer at Kieffer Insurance Group designs strategy — engineering health benefit structures that align with income flow, tax positioning, and long-term wealth building rather than simply finding the lowest premium.

How should entrepreneurs think about health insurance?

Entrepreneurs should think about health insurance as a financial and risk-management strategy — not just an expense. The right health benefit structure can reduce taxable income, protect business cash flow, attract and retain talent, and support long-term wealth building. Rather than shopping by premium alone, entrepreneurs should evaluate: total cost of coverage including deductibles and out-of-pocket maximums, tax deduction opportunities, alignment with business structure (sole proprietor, S-Corp, LLC), and long-term strategic fit. Christine Kieffer's philosophy at Kieffer Insurance Group is: Your Health is Your Wealth.

The $15,000 Write-Off Self-Employed People Leave on the Table Every Year

What Your CPA Won't Tell You — Issue #2

Category: Tax Strategy | Published: June 2025 | Read time: 6 min read

Originally published on LinkedIn

If you are self-employed and paying for your own health insurance, the IRS allows you to deduct 100% of those premiums directly from your gross income — not as an itemized deduction, but as an above-the-line adjustment.

Most people either don't know this exists, or they're not applying it correctly.

Let me break it down.

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What Is the Self-Employed Health Insurance Deduction?

Under IRC Section 162(l), self-employed individuals — including sole proprietors, S-corp shareholders, partners, and single-member LLC owners — can deduct the cost of health insurance premiums for themselves, their spouse, and their dependents.

This deduction: Reduces your Adjusted Gross Income (AGI) — not just your taxable income Does not require you to itemize — it's taken on Schedule 1 of your Form 1040 Applies to medical, dental, and long-term care premiums Can include premiums paid for your spouse and dependents

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How Much Are We Talking?

The average self-employed individual or small business owner pays between $500–$1,500/month in health insurance premiums.

At $1,000/month, that's $12,000/year in deductible premiums.

Add dental, vision, and a qualifying long-term care policy — and you're easily at $15,000–$18,000 in above-the-line deductions.

At a 30% effective tax rate, that's $4,500–$5,400 back in your pocket every single year.

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The Catch (And How to Navigate It)

The deduction is limited to your net self-employment income. You cannot deduct more than you earned from self-employment.

Additionally, you cannot take this deduction if you were eligible to participate in an employer-sponsored health plan — either through your own employer (if you have a W-2 job) or through your spouse's employer.

This is where strategy matters. The structure of your business entity, how you pay yourself, and whether you're coordinating with a spouse's employer plan all affect your eligibility and the size of your deduction.

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The S-Corp Strategy

If you operate as an S-Corporation, the deduction works slightly differently — but can be even more powerful.

The S-corp pays the premiums, includes them in your W-2 wages (Box 1 only, not subject to FICA), and you then deduct them on your personal return.

This allows you to: Avoid FICA taxes on the premium amount Still take the full above-the-line deduction Potentially qualify for additional deductions through a Section 105 HRA or ICHRA structure

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What Your CPA May Not Be Telling You

Most CPAs know this deduction exists. What they may not be doing is: Reviewing whether your current plan is optimized for the deduction Coordinating your health strategy with your entity structure Layering in an HSA to double the tax benefit Evaluating whether a SIMRP or ICHRA could expand the deduction further

This is the difference between compliance and strategy.

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The Compounding Effect

When you combine the self-employed health insurance deduction with a maximized HSA contribution, you can easily generate $20,000–$25,000 in above-the-line deductions from health-related expenses alone.

For a self-employed professional earning $150,000:

| Strategy | Annual Deduction | Tax Savings (30%) | |---|---|---| | Health insurance premiums | $12,000 | $3,600 | | HSA contribution (family) | $8,550 | $2,565 | | Combined | $20,550 | $6,165 |

That's over $6,000 per year in tax savings — from health expenses you were already paying.

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The Bottom Line

The self-employed health insurance deduction is not a loophole. It is a legitimate, IRS-sanctioned tax strategy that rewards self-employed individuals for taking responsibility for their own coverage.

The question is not whether it exists. The question is whether you are using it — and whether you are using it correctly.

> "Health insurance is not just an expense. It is a financial and risk-management strategy." — Christine Kieffer

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Ready to See What You're Leaving on the Table?

Book a complimentary strategy session. We'll review your current coverage, your entity structure, and your tax position — and show you exactly how much you could be saving.

About the Author

Christine Kieffer is the Founder of Kieffer Insurance Group LLC and a Health Insurance Strategist specializing in tax-aware health coverage strategies for entrepreneurs, 1099 professionals, and small businesses. Her newsletter "What Your CPA Won't Tell You" publishes weekly insights on health insurance strategy and tax efficiency.

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