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Having a board of advisors isn't just for big companies. Even small business owners and solo entrepreneurs can use it to grow smarter and save money on taxes. In this episode, Mike shares how a board helps you deduct meals, travel, and even your home—plus how it keeps you organized and protected.

Chapters:

(00:58) What’s a Board of Advisors?
It’s a group of people who give advice and support for your business—even if you’re running solo.

(02:18) How to Set It Up
Add it to your business documents, pick people you trust, and plan regular meetings.

(04:48) Tax Write-Offs You Can Claim
Board meetings can make meals, travel, and even home use partially or fully deductible.

(05:38) The Augusta Rule Trick
Rent your home to your business for board meetings and pay zero tax on that rental income (if done right).

(08:15) More Benefits Than Just Tax
It helps with accountability, planning, outside feedback, and even audit protection.

(11:12) Keep Records That Count
Document every meeting with notes, receipts, and details to stay safe and get the most tax savings.

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

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

Have you ever wondered if you can write off beers with a client? Or claim mileage between your home and office? In this special Q&A episode, Mike answers real questions from small business owners across the country — tackling topics like the Augusta Rule, tax deductions you're probably missing, how to handle multi-state operations, and even the proper way to record equipment purchases in your books.

Chapters:

(01:16) What is the Augusta Rule?
Rent your home to your business for 14 days or less, and pay zero tax on that income — here’s how it works.

(02:29) Can You Deduct Beers with Clients?
Yes, you can — but only if there’s a valid business reason and proper documentation.

(05:17) Home Office Deduction and Mileage Explained
Mike clears up confusion about home offices, commuting, and how an accountable plan changes what you can deduct.

(08:00) Does TaxElm Make Sense for Me?
If you’re a small business owner or a high-income earner with a side hustle, here’s how TaxElm could help.

(10:32) Where to Incorporate if You're in Multiple States
Learn how tax nexus works and why forming your LLC in a random state could backfire.

(12:16) How to Record Equipment Purchased with a Loan
Breaking down how to properly track assets, liabilities, and depreciation in your bookkeeping.

(14:30) What is a Family Office and Do You Need One?
Mike shares how to build a “family office” strategy — even if you’re not ultra-wealthy.

(16:00) Tax Deductions Most Business Owners Miss
From hiring your kids to internet bills, here are deductions you might be overlooking.

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

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

If you’ve ever skipped filing a tax return or felt overwhelmed by back taxes, this episode is for you. Mike and Robert Nordlander, former IRS Special Agent, break down the real risks of not filing, the difference between filing and paying, and how to get back on track—without fear.

Chapters:

(00:26) Falling Behind on Taxes Happens
Mike shares a common fear of business owners who haven’t filed in years and feel buried in penalties—but there’s a way out.

(02:30) Not Filing is a Crime
Robert explains that failing to file is a criminal offense, even if you're owed a refund. You could face jail time.

(04:20) Filing Protects You (Even if You Can’t Pay)
Filing and paying are separate. Filing your return stops criminal penalties—even if you don’t have the money yet.

(06:30) Penalties vs. Interest: Why Filing Matters
Not filing triggers a 25% penalty. Filing without paying is just 0.5% monthly. Filing first always puts you in a better position.

(08:57) No Records? There’s Help
If your records are missing or a mess, a CPA or forensic accountant can help you recreate what’s needed to get back on track.

(11:33) IRS Payment Plans + the 10-Year Rule
The IRS offers payment plans and even settles for less in some cases. But you must stay compliant—your debt can go away after 10 years if you do.

(23:58) Why You Don’t Want to Owe the IRS
The IRS is more aggressive than banks. They can seize wages and assets without going to court—and their customer service is notoriously bad.

Guest: Robert Nordlander, CPA – https://www.nordlandercpa.com

Find Robert’s Books:

• Criminal Tax Secrets: What Every Defense Attorney Should Know
• Unpaid Payroll Taxes: A Time Bomb You Can Defuse
• Erase the Penalty: A Tax Professional's Guide to Abatement

-------

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, we'd love for you to leave a 5-star review on Apple Podcasts or Spotify to help others discover the show ⭐

🎙 ABOUT THE PODCAST

The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies designed to help entrepreneurs and small business owners legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this podcast breaks down complex tax topics into clear, actionable, no fluff insights, so you can maximize your savings and keep more of your hard-earned money.

a

Send us a text

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

If you’re self-employed or earn income without tax withholding, the IRS expects you to make estimated payments throughout the year, not just at tax time. Missing a deadline could cause you costly penalties and interest.

In this episode, we cover everything you need to know about estimating and paying taxes; Who needs to pay, when it's due, and how to avoid IRS penalties.

Chapters:

00:00 The IRS Won’t Wait: Estimated taxes apply to income without withholding, like self-employment, rentals, and investments. If you don’t pay throughout the year, you could face major penalties.

01:09 What Income Requires Estimated Payments: Self-employed earnings, K-1s, rental income, capital gains, and interest or dividends.

03:02 Pay As You Earn Explained: The U.S. requires you to pay taxes as you earn income. W-2 employees have taxes taken out automatically, but business owners have to do it themselves.

05:43 Estimated Tax Deadlines: IRS quarterly deadlines: Q1 due April 15, Q2 due June 15, Q3 due September 15, Q4 due January 15 (of the following year)

08:42 Don’t Forget State Estimated Payments: State income taxes may also require estimated payments. Deadlines and rules vary, so check your state’s tax agency website.

08:58 IRS Safe Harbor Rule: Avoid penalties by either paying 100% of last year’s taxes (110% if you made over $150K) or paying 90% of what you’ll owe this year.

11:37 How to Estimate and Pay: Steps to estimate your income, calculate tax, divide it quarterly, and make timely payments using IRS Direct Pay or your state’s website.

12:15 Penalties and Interest for Missing Payments: Missing payments can trigger a 0.5 percent monthly penalty (up to 25 percent) and 3 to 8 percent interest based on short-term federal rates.

-------

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, we'd love for you to leave a 5-star review on Apple Podcasts or Spotify to help others discover the show ⭐

🎙 ABOUT THE PODCAST

The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies designed to help entrepreneurs and small business owners legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this podcast breaks down complex tax topics into clear, actionable, no fluff insights, so you can maximize your savings and keep more of your hard-earned money.

Send us a text

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

If you own your business and the building it operates from, self-renting can be a powerful tax-saving strategy, but only if structured properly.

Done wrong, it triggers the self-rental tax trap, where your rental income is taxed as non-passive, but your losses are locked away as passive. In this episode, we explain how to structure self-rentals the right way, avoid IRS red flags, and leverage the IRS Reg 1.469-4D Grouping Election to unlock tax savings.

00:00 - What is a Self-Rental?
Self-rental happens when you own both your business and the building it operates from.

03:15 - How the Self-Rental Trap Works
Rental income from your own property is treated as non-passive, while losses remain passive. Passive losses cannot offset your active business income, creating a mismatch that costs you thousands in taxes.

06:30 - Fixing the Trap: IRS Grouping Election (Reg. 1.469-4D)
The IRS allows you to group the business and rental as one activity for tax purposes. This grouping election reclassifies the losses, allowing you to offset them against business profits.

09:45 - How a Chiropractor Saves $20,000+
A chiropractor earns $500,000 in business profit while the building generates a $100,000 loss due to depreciation and cost segregation. Without the election, the loss is suspended. With the election, the loss offsets business income, reducing taxable income to $400,000.

13:00 - How to Structure Your Self-Rental Correctly
Draft a rental agreement with fair market value rent. Ensure common ownership between the business and property. If the property has unrelated tenants, only the portion used by your business qualifies. Make the grouping election on your tax return the first year you do this.

16:30 - Common Mistakes to Avoid
Disproportionate ownership between the business and property disqualifies you from making the election. Missing documentation or failing to file the election causes the IRS to apply the trap rules, limiting your deductions.

18:36 - Final Thoughts
Properly structuring your self-rental and making the IRS grouping election is the key to turning potential tax traps into powerful tax savings.

-------

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, we'd love for you to leave a 5-star review on Apple Podcasts or Spotify to help others discover the show ⭐

🎙 ABOUT THE PODCAST

The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies designed to help entrepreneurs and small business owners legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this podcast breaks down complex tax topics into clear, actionable, no fluff insights, so you can maximize your savings and keep more of your hard-earned money

Send us a text

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

Are you worried that claiming a tax deduction might land you in an orange jumpsuit? Fear of the IRS stops too many business owners from taking legitimate tax-saving opportunities.

In this episode, we’re breaking down the difference between civil and criminal tax cases—and exactly what really puts people behind bars. Special guest Robert Nordlander, CPA and former IRS Criminal Investigator, shares insider stories and tips you won’t want to miss.

Chapters:

(00:57) Civil vs. Criminal Tax Issues: 90% of IRS activity is civil and focused on collecting what’s owed. Criminal charges only apply when there’s willful fraud.

(03:25) What Does Criminal Intent Look Like? Mistakes or gray areas won’t land you in jail. It’s repeated deception, false documents, and ignoring professional advice that cross the line.

(06:48) Does an IRS Audit Mean Jail Time? No. Audits are civil. Agents are trained to spot fraud indicators, but very few cases ever get referred to the criminal division.

(13:39) Aggressive Tax Planning vs. Illegal Tax Evasion: Learn where the line is between pushing the rules and breaking the law… and why you should ignore TikTok tax advice.

(19:04) What Actually Gets Business Owners in Jail: Payroll taxes are the #1 reason small business owners get in trouble—especially when they use withheld taxes for personal expenses.

(27:52) What to Do If You Get an IRS Letter or Criminal Inquiry: Step one—open your mail! Step two—hire a pro. If IRS Criminal Investigation shows up? Lawyer up and stay quiet.

Guest: Robert Nordlander, CPA – https://www.nordlandercpa.com

Find Robert’s Books:

• Criminal Tax Secrets: What Every Defense Attorney Should Know
• Unpaid Payroll Taxes: A Time Bomb You Can Defuse
• Erase the Penalty: A Tax Professional's Guide to Abatement

-------

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, we'd love for you to leave a 5-star review on Apple Podcasts or Spotify to help others discover the show ⭐

🎙 ABOUT THE PODCAST

The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies designed to help entrepreneurs and small business owners legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this podcast breaks down complex tax topics into clear, actionable, no fluff insights, so you can maximize your savings and keep more of your hard-earned money.

Send us a text

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

Tax deadlines are approaching fast! If you’re scrambling to get your paperwork together, you might be wondering if filing a tax extension is the right move. In this episode, we’re breaking down everything you need to know about filing an extension for both business and personal taxes—including how to do it right, when to file, and how to avoid IRS penalties.

Chapters:

00:57 Why Business Owners File Extensions: Tax returns are due soon, and many business owners are still gathering paperwork. If you need more time, an extension might be the answer.

02:09 What is a Tax Extension? Filing an extension gives you more time to submit your return, but it does NOT extend your payment deadline.

03:29 Extension Deadlines & Forms: Business returns (S Corps & Partnerships) are due March 15th (Form 7004). Personal returns (including sole proprietors) are due April 15th (Form 4868).

05:44 Will Filing an Extension Trigger an Audit? Filing an extension does not increase audit risk. In fact, it can help you avoid an audit by reducing errors from rushing.

07:10 How to Make a Tax Payment with Your Extension: The IRS still expects you to pay what you owe by the original due date, even if you extend. Options include IRS Direct Pay, debit/credit card, or automatic bank withdrawal. Don’t forget state tax payments if required!

12:54 What Happens If You Don’t File an Extension? Businesses face a penalty of $200+ per partner per month! Individuals face a 5% penalty per month on unpaid taxes.

14:43 Can’t Afford to Pay? Here’s What to Do: Always file your return or extension to avoid late-filing penalties. If you can’t pay, consider an IRS payment plan or installment agreement.

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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, we'd love for you to leave a 5-star review on Apple Podcasts or Spotify to help others discover the show ⭐

🎙 ABOUT THE PODCAST

The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies designed to help entrepreneurs and small business owners legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this podcast breaks down complex tax topics into clear, actionable, no fluff insights, so you can maximize your savings and keep more of your hard-earned money.

Send us a text

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

Starting and running an LLC comes with big tax benefits and liability protections—but only if you do it right. In this episode, we break down the 10 most common LLC mistakes that could cost you thousands in taxes, legal troubles, or even your business itself.

Chapters:

(00:57) Mixing Personal & Business Finances: Co-mingling accounts makes bookkeeping messy and can trigger IRS scrutiny. Always keep separate business bank accounts.

(2:24) Forgetting to File Annual Reports: If you miss this, your LLC can be administratively dissolved, meaning your business legally ceases to exist.

(03:25) Not Using "LLC" on Business Documents: Failing to include "LLC" in contracts and agreements can leave you personally liable in legal disputes.

(04:21) Registering an LLC in Another State Without a Foreign Designation: Setting up in a tax-friendly state (like Wyoming) doesn’t exempt you from taxes where you operate. You must file a Foreign LLC election.

(07:22) Not Maintaining Meeting Minutes & Operating Records: Proper documentation is essential for legal protection and can also unlock tax deduction opportunities (e.g., business meals).

(08:56) Making Business Decisions Without Consulting LLC Members: If you have multiple members, one rogue decision can cause disputes and even dissolve the LLC.

(10:28) Mixing Personal Expenses with Business for Tax Deductions: Running personal expenses through your LLC is a red flag for the IRS. Use an accountable plan to track reimbursements properly.

(12:05) Not Obtaining Required Business Licenses & Permits: Some businesses require licenses at the state or local level. Ignoring them can lead to fines or forced shutdowns.

(12:49) Skipping Professional Liability Insurance: An LLC protects your personal assets, but business insurance protects your company from lawsuits and financial losses.

(14:21) Not Updating Your Registered Agent Information: If your LLC moves or changes leadership, failing to update records can lead to missed legal notices and compliance issues.

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

-------

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

🚀 Join 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, we'd love for you to leave a 5-star review on Apple Podcasts or Spotify to help others discover the show ⭐

🎙 ABOUT THE PODCAST

The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies designed to help entrepreneurs and small business owners legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this podcast breaks down complex tax topics into clear, actionable, no fluff insights, so you can maximize your savings and keep more of your hard-earned money.