Your health insurance could do more than cover medical emergencies. With the right strategy, it could also help you save on taxes.

In this episode, Mike Jesowshek, CPA, breaks down health insurance options for small business owners, from group plans to employee reimbursements and stipends. He explains the steps S corp owners need to take to deduct their health insurance premiums and how eligible business owners can use an HSA for tax savings and long-term growth.

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00:00 | Health Insurance as a Tax Strategy
How healthcare planning can help business owners protect themselves, offer employee benefits, and save on taxes.

01:00 | Your Health Insurance Options
An overview of group plans, self-funded plans, HRAs, and stipends, plus how your needs differ when you’re self-employed.

03:00 | The HSA’s Triple Tax Advantage
A look at tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses.

04:00 | Group Health Insurance Plans
How group plans work and how employers decide what portion of employee premiums to cover.

05:00 | Self-Funded and Level-Funded Plans
How these plans differ from traditional group insurance, including potential savings and risks.

07:00 | Health Reimbursement Arrangements
How HRAs let employers reimburse eligible healthcare costs and why employees need to document their expenses.

08:00 | Stipends and Offering No Coverage
The tax tradeoffs of paying employees extra for healthcare and how benefits can help attract and retain talent.

11:00 | Health Insurance for S Corp Owners
The payment, W-2 reporting, and personal tax return steps discussed for claiming the health insurance deduction.

15:00 | HSA Eligibility and Contribution Limits
An explanation of qualifying health plans and the contribution limits covered in the episode.

17:00 | Investing Your HSA and Saving Receipts
Why leaving funds invested may support long-term growth, and how saved medical receipts can support later reimbursements.

19:00 | Review Your Healthcare Strategy Each Year
Bring coverage, deductions, employee benefits, and HSA planning together as your business grows.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
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