Stop paying your medical bills with after-tax dollars

You’re already paying for deductibles, prescriptions and co-pays. With the right setup, your business could pay you back for them, tax-free.

In this episode, Mike Jesowshek, CPA, explains how a medical expense reimbursement plan (also called an owner HRA or Section 105 plan) can turn out-of-pocket medical costs into business deductions. He covers who qualifies, which entity types work for single and married owners, and the workaround for S corp owners. He also walks through the paperwork you need, how to report the plan on your tax return, and the common mistakes that can cost you the deduction.

👉Find out how much your business could save in taxes:

TaxSavingsPodcast.com/scorecard

🚀 Book your free demo call today. Click here or visit:

https://taxelm.com/demo/

00:00 Why Your Medical Costs Aren’t Fully Deductible
Mike explains who this strategy is for (owners with no employees outside the family) and why high out-of-pocket medical costs often get little or no deduction as itemized deductions, even in a costly year.

03:00 What a Section 105 Plan Is and Who Qualifies
How a medical expense reimbursement plan lets your business reimburse an employee for qualified family medical costs, turning after-tax spending into pre-tax business deductions. It also covers the no-employee requirement and how other businesses you own could affect whether you qualify.

06:00 Entity Type, Marital Status, and the S Corp Workaround
Why single owners need a C corp and married owners can hire their spouse through a sole proprietorship, partnership, C corp, or rental property. Mike also explains why the plan doesn’t work in an S corp and how moving part of your income into a separate entity can get around that.

09:00 Setting Up the Plan and Reimbursing Expenses
The paperwork you need, including a written plan document, employment agreement, job description, and time log. Mike also covers which expenses qualify under IRS Publication 502 and how receipts, a reimbursement log, and payments from the business account support each claim.

13:00 Reporting the Deduction on Your Tax Return
Where the deduction goes on a Schedule C, partnership return, C corp return, or Schedule E rental, why these costs no longer belong on Schedule A, and the Form 720 filing that goes with the plan.

16:00 Is It Worth It? A Real Number Example
How $50,000 in qualified medical expenses could create more than $17,000 in tax savings. Mike also explains why the plan usually isn’t worth it under $5,000 in costs and when it starts to make sense.

18:00 Mistakes to Avoid and Key Takeaways
The most common mistakes, including missing paperwork, a spouse who doesn’t do real work, outside employees, using an S corp, and improper reimbursements. Mike closes with why getting the structure right matters, especially for families with ongoing medical costs.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

🚀 Visit: https://www.TaxSavingsPodcast.com

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

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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.

👉Find out how much your business could save in taxes.

TaxSavingsPodcast.com/scorecard

🚀 Book your free demo call today. Click here or visit:

https://taxelm.com/demo/

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
Join TaxElm: https://taxelm.com

🚀 Visit: https://www.TaxSavingsPodcast.com

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐

Documentation 101: How to Prepare for an IRS Audit

You claimed the deduction. But if the IRS asks, can you prove it?

Mike Jesowshek, CPA, explains which records you need to support your business expenses. Learn how to document purchases, keep clean books, and organize your receipts so you’re prepared if the IRS comes knocking.

👉Find out how much your business could save in taxes.

TaxSavingsPodcast.com/scorecard

🚀 Book your free demo call today. Click here or visit:

https://taxelm.com/demo/

Chapters:

00:00 Your Tax Deductions Need Documentation
Paying with a business card doesn’t automatically make a purchase deductible. You need records showing what you bought and why it was business related.

03:00 Audit Selection vs. Audit Outcome
Even well-organized businesses can get audited. Good documentation helps you support your deductions if you’re selected.

08:00 The Proof Behind a Business Deduction
Every deduction needs an actual transaction, a business purpose, and the correct tax treatment. Your supporting records should match.

12:00 Clean Books and Separate Bank Accounts
Separate business and personal accounts, update your books regularly, and clearly label expenses, transfers, and owner activity.

14:00 Business Structure, Payroll, and Reimbursements
Your tax filings and records should match your business structure. Payroll, accountable plans, and meeting records need proper implementation.

17:00 What to Record Beyond the Receipt
Document the business purpose and who was involved. Supporting invoices, calendar entries, and emails can help explain the expense.

19:00 Supporting Records for Mileage, Travel, and More
Mileage, travel, equipment, contractors, loans, and reimbursements each need records that support the transaction.

20:00 Building an Audit-Ready Workflow
Capture receipts promptly, add context, categorize expenses consistently, and save your documents digitally.

22:00 Testing Whether You Can Find Your Records
Choose an older transaction or five large expenses. Check whether you can quickly find the records supporting them.

23:00 What to Do When an Audit Letter Arrives
Read the request carefully, meet deadlines, organize your response, and speak with a qualified tax professional.

25:00 How Good Documentation Pays Off
Organized records make audit responses faster and deductions easier to defend. Clean books also help you make business decisions.

27:00 Why Tax Strategies Need a Paper Trail
Putting a strategy into practice includes documenting it. Hiring your kids, for example, requires records of their work and payments.

28:00 Key Takeaways and Next Steps
Clean books and timely documentation help you prepare for an audit. Learn where to find support implementing tax strategies.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

🚀 Visit: https://www.TaxSavingsPodcast.com

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐