He Makes $300K+ with an S-Corp… But Paid Way Too Much in Taxes! Live Tax Audit
Small Business Tax Savings Podcast
HSA strategy and self‑insured benefits
Mike praises investing HSA funds and explains tax‑free growth and reimbursements for future medical expenses.
Most S Corp owners follow the right steps, but still pay more tax than they should. A business earning over 300K can lose thousands simply by underusing core strategies.
In this live case study, Mike Jesowshek, CPA, reviews a seven-figure business with an S Corp structure, a salary in place, and a record year of profit. You will see why this owner paid 30K in taxes and how that number can be reduced.
If you feel like your tax plan has stopped working, this breakdown gives you a clear blueprint for moving from basic strategies into advanced tax planning.
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01:11 The Core Strategy Checklist
What an accountable plan should include, how home office reimbursements really work, and why quarterly board meetings leave tax savings behind.
02:53 After-Tax vs Pre-Tax Spending Explained
How shifting everyday expenses into legitimate business categories creates immediate tax savings without increasing spending.
05:04 The Most Underused S Corp Deduction: Meals
Why meals often show up too low on tax returns, how to identify real business-meal opportunities, and how to document them correctly.
09:01 Travel Deductions Most Owners Miss
How to turn partial travel into fully deductible business trips, how business days are determined, and how to integrate board meetings into travel.
15:41 Using the Augusta Rule at Its Full Potential
How to calculate fair rental value, document the rental period, and structure meetings to justify 14 tax-free rental days.
17:43 How to Calculate a Defensible S Corp Salary
The two accepted methods for determining reasonable compensation and how to avoid both overpaying and triggering IRS scrutiny.
23:00 Maximizing Solo 401(k) Contributions
How contribution limits work, how salary affects maximum contributions, and why timing matters before hiring your first W-2 employee.
34:00 When a Business Becomes Ready for Advanced Planning
The five major categories of advanced tax strategy and how to determine which ones open up as revenue approaches seven figures.
38:22 Building a Scalable Tax Plan
Optimizing old strategies and documenting them correctly produces long-term savings, even before layering advanced planning on top.
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 y
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