Year-End Tax Strategies Every Business Owner MUST Do Before December 31

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Dec 3, 2025

Year-end is the critical time for business owners to secure tax savings. Key strategies include ensuring S Corp compliance, maximizing deductions through careful planning, and hiring kids in a tax-smart way. Don't forget retirement contributions and health reimbursements before deadlines! Timing strategies for cash-basis filers can enhance deductions, while tax-loss harvesting helps offset gains. Documenting everything now ensures a cleaner tax season ahead, so prioritize high-impact strategies for a productive start to the new year!

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ADVICE

S‑Corp Year‑End Must‑Dos

Run a reasonable S‑Corp salary and adjust with bonuses before December 31.
Add self‑employed health insurance to box 1 on your W‑2 and finalize accountable plan reimbursements.

ADVICE

Capture Missed Deductions

Scan personal statements for business expenses and reimburse through an accountable plan.
Hire kids properly, use the Augusta Rule for short home rentals, and document board meetings and home office reimbursements.

ADVICE

Retirement & Health Deadlines

Make employee 401(k) deferrals by December 31 to secure the deduction.
Complete any Section 105 or HRA reimbursements before year‑end.

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Year-end is the last chance to lock in major tax savings for your business.

In this episode, Mike walks through the exact steps business owners need to take now, from S Corp requirements and accountable plans to AGI phaseouts, QBI planning, and the Augusta Rule.

You’ll also learn how to hire your kids correctly, hit retirement deadlines, use timing strategies as a cash-basis filer, harvest tax losses, and document every move so you enter tax season clean, organized, and ready.

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Chapters

(00:49) Three Must-Do Steps for S-Corp Owners
Reasonable salary, adding self-employed health insurance to your W-2, and making final accountable plan reimbursements. Mike breaks down each requirement and what has to be done before 12/31.

(04:51) Maximize Deductions Before the Year Ends
Go through personal statements for missed deductions, hire your kids correctly, use the Augusta Rule, finalize board meetings, and make home office and auto reimbursements.

(08:14) Retirement and Health Reimbursement Deadlines
Employee 401(k) contributions must be made by year-end. Mike also covers Section 105 medical reimbursement plans and HRAs.

(14:17) Timing Strategies for Cash-Basis Filers
When to prepay expenses, when to delay invoicing, and how credit cards can accelerate deductions. Mike also explains why low-income years are ideal for Roth conversions.

(17:39) Miscellaneous but High-Value Year-End Moves
Why assets must be “placed in service,” how tax loss harvesting works, and the December 31 deadline for charitable giving.

(19:35) Get Ready for January
Collect W-9s, prep 1099s, store receipts digitally, document every strategy, and get bookkeeping up to date to avoid a stressful tax season.

(22:54) Don’t Get Overwhelmed
Focus on the two or three highest-impact strategies now, then committing to proactive planning next year.

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.