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Do you really have your tax planning handled? The thing is, many business owners are making a critical mistake that will become even more expensive by 2026.

In this episode, Mike Jesowshek, CPA, sits down with Mark J. Kohler to expose the biggest tax planning failure business owners make. Confusing knowing strategies with actually applying them. Mark explains why tax savings disappear at the implementation level, how poor execution creates long-term consequences, and why retirement accounts are one of the most overlooked areas where this mistake shows up.

👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners: https://www.taxsavingspodcast.com/starterkit

🚀 Book your free demo call today! Click here or visit: https://taxelm.com/demo/

Chapters

(01:02) Why Most Tax Strategies Never Get Implemented
Many business owners think they are doing tax planning, but when you look at their tax return, the strategies are missing.

(03:05) Tax Strategy vs Tax Compliance
There is a major disconnect between tax advisors and tax preparers.

(05:18) What “Self-Directed” Really Means
Wall Street uses the term self-directed loosely. Mark explains the real definition and why traditional brokers do not promote it.

(07:04) What You Can Invest in With a Self-Directed IRA
Real estate, private businesses, lending, crypto, precious metals, and more. Mark walks through the types of investments retirement accounts are legally allowed to own.

(09:36) Prohibited Transactions and IRS Red Flags
It is not about prohibited assets. It is about prohibited people and personal benefit.

(12:02) Can You Be Active in Retirement-Owned Investments
You can make decisions, write checks, and structure deals, but you cannot personally perform labor or manage properties.

(14:01) Cost and Setup of a Self-Directed IRA
Many people assume self-directing requires hundreds of thousands of dollars.

(15:52) Employer 401ks vs Self-Directed Plans
Why most employer-sponsored 401ks restrict your options and how entrepreneurs can set up plans that allow true self-direction.

(18:06) When Self-Directed IRAs Are Not a Good Fit
Self-directing requires time, focus, and discipline. Mark explains when investors should wait or choose simpler options.

(19:33) How to Get Started the Right Way
Education comes first. Mark shares resources, podcasts, books, and next steps for learning before investing.

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 ⭐

🎙 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 clea

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If you’re a new business owner, you've probably wondered if you are doing any of this correctly.

Should you get an LLC? Do you file a Schedule C? Can you hire your kids? Does a home office hurt you when you sell your house?

In this episode, Mike walks through real questions from listeners and gives clear answers to the tax issues that confuse most new entrepreneurs. From 1099 income and deductions to home office rules, the Augusta Rule, and hiring your kids, this Q&A hits the topics every early-stage owner struggles with.

👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners: https://www.taxsavingspodcast.com/starterkit

🚀 Book your free demo call today! Click here or visit: https://taxelm.com/demo/

(01:00) Starting as a 1099 Contractor & What Is Schedule C? The foundational steps every new contractor must take and how 1099 NEC income flows into Schedule C, how expenses reduce profit, and why self employment tax becomes a factor.

(05:10) Do You Need an LLC to Take Deductions? Home office, mileage, meals, and travel can all be deducted without an LLC
(08:53) ROBS vs SBA Loans for New Businesses: Mike breaks down the pros and cons of using retirement funds through a ROBS structure compared to financing with an SBA loan.
(10:19) Hiring Your Kids: Payroll vs Contractor: The age rule most parents get wrong. Under 18, children should be W2 employees. Over 18, contractor payments may work if they have legitimate expenses.
(13:00) Home Office Deduction and Selling Your House: Simplified method vs actual method. When depreciation recapture applies. Why the impact is usually small.
(15:00) Transitioning to Business Ownership: A listener plans to leave a W2 job for business ownership. Mike explains where strategy matters most at the beginning.

(17:40) Home Office vs Augusta Rule: Yes, you can use both. The key is using different rooms. Home office in one area. Board meeting in another.
(19:47) Do You Need an LLC for a Small Side Gig: A listener making five to nine thousand a year wonders whether to form an LLC. Mike explains why it will not change taxes at low income levels and when it becomes useful.

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 ⭐

🎙 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.

Send us a text

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.

👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners: https://www.taxsavingspodcast.com/starterkit

🚀 Book your free demo call today! Click here or visit: https://taxelm.com/demo/

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
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 ⭐

🎙 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.