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    Business

    Small Business Tax Savings Podcast

    The Small Business Tax Savings Podcast is designed specifically for small business owners. We focus on tax savings and ways to have a financially sound back bone to your small business. Our goal is to have you paying the least amount in taxes as legally possible.Hosted by by Mike Jesowshek, CPA, this is a quick hitting podcast aimed to get you important information without all the fluff. You can find episodes, blog posts, information on our software TaxElm and more on our website: www.TaxSavingsPodcast.com

    Advertise

    Copyright: © 2024 Small Business Tax Savings Podcast

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    Latest Episodes:
    Filing Your Taxes LATE? IRS Penalties, Payment Plans & Relief Apr 09, 2025
    Show notes

    🚀 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


    How to Estimate Taxes in 2025 for Small Business Owners Apr 02, 2025
    Show notes

    🚀 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.

    [01:08] What Income Requires Estimated Payments
    Self-employed earnings, K-1s, rental income, capital gains, and interest or dividends.

    [03:15] 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.

    [05:45] 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.

    [09:00] 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.

    [11:27] 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.

    [12:06] 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.



    Rent Your Building to Your Business? Avoid the IRS Self-Rental Trap Mar 26, 2025
    Show notes

    🚀 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


    Will the IRS Send You to Jail? Civil vs. Criminal Tax Issues Mar 19, 2025
    Show notes

    🚀 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.


    How to File A Tax Extension in 2025 (What Small Business Owners Need to Know) Mar 12, 2025
    Show notes

    🚀 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.


    -------

    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.



    Avoid These 10 LLC Mistakes in 2025 Mar 05, 2025
    Show notes

    🚀 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.


    -------

    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.


    New Tax Relief? What Trump's Tax Changes Mean For Your Business Feb 26, 2025
    Show notes

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

    How will Trump's proposed tax changes impact your business if they're implemented?

    In 2017, the Tax Cuts and Jobs Act (TCJA) was passed by the Senate and signed into law by President Donald Trump, introducing major tax cuts for individuals and businesses. Many of these tax breaks are set to expire at the end of 2025 unless Congress extends them. In this episode, we break down which tax cuts are expiring, what Congress might do, and how you can prepare.

    Chapters:

    (00:58) What’s Expiring in 2025?: Major tax provisions from TCJA are set to expire, leading to potential tax increases.

    (02:14) Higher Individual Tax Rates: If Congress does nothing, tax rates will go up for most Americans.

    (03:12) Shrinking Standard Deduction: The standard deduction, which nearly doubled under TCJA, will revert to pre-2017 levels.

    (04:07) Reduced Child Tax Credit: Parents may lose up to $1,000 per child in tax savings.

    (05:22) Changes to SALT Deduction Limits: The current $10,000 cap on State and Local Tax (SALT) deductions may be adjusted or removed.

    (07:10) Small Business Owners Lose Big: The QBI Deduction Disappears – The 20% Qualified Business Income (QBI) deduction for pass-through businesses is at risk.

    (08:56) Bonus Depreciation Phases Out: Businesses will no longer be able to immediately write off 100% of qualifying purchases.

    (10:45) Estate and Gift Tax Exemptions Shrink: The exemption amount for estate and gift taxes could drop significantly, affecting wealth transfers.

    (12:21) What Will Congress Do? Lawmakers are debating which provisions to extend and how to pay for tax cuts.

    (14:06) How Will the Government "Pay For" Tax Cuts? Cutting taxes means less government revenue. Will spending cuts or new taxes offset the shortfall?

    (16:30) Trump’s New Tax Proposals, What’s the Catch? No tax on tips, Social Security income, and overtime pay are on the table, but will they actually happen?

    (19:22) What Should Business Owners Do Now? Strategies to prepare for 2026 and protect your business from tax increases.


    -------

    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.



    Beware of Hidden Built-In Gain (BIG) Taxes When Transitioning to S Corporation Feb 19, 2025
    Show notes

    Thinking about converting your C Corporation to an S Corporation? Before making the switch, do you know about the Built-In Gains (BIG) Tax—and how it could cost you thousands if you don’t plan ahead?


    In this episode, Mike Jesowshek breaks down the Built-In Gains (BIG) Tax, a critical consideration for business owners converting from a C Corporation to an S Corporation. He explains why this tax exists, how it prevents businesses from avoiding double taxation, and the conditions under which it applies. Mike walks through key scenarios where the BIG Tax may or may not apply, how to calculate it, and the best strategies for minimizing or avoiding it.


    [00:00 - 03:30] Understanding the Built-In Gains (BIG) Tax

    • Mike introduces the BIG Tax and its purpose in preventing tax avoidance.
    • What is the difference of taxation for C Corps versus S Corps?
    • Owners need to be aware of BIG Tax before making an S Corp election.


    [03:31 - 11:15] Calculating the BIG Tax & IRS Considerations

    • Mike shares the three key conditions that trigger the BIG Tax.
    • Fair market value vs. adjusted basis determines built-in gains.
    • Mike discusses the step-by-step breakdown of how to calculate the BIG Tax.
    • Proper asset valuation at the time of conversion is critical.


    [11:16 - 14:00] Strategies to Avoid the BIG Tax

    • Hold onto assets for at least five years to bypass taxation.
    • Time asset sales in loss years to offset taxable gains.
    • Utilize NOL (Net Operating Loss) carryovers from the C Corp.


    [14:01 - 17:32] When the BIG Tax Does NOT Apply and Final Considerations

    • Mike shares scenarios where business owners don’t have to worry about the BIG Tax.
    • BIG Tax is not a reason to avoid an S Corp election—planning is key.
    • What is the importance of documentation and fair market value assessments?


    Notable Quotes:


    “The BIG Tax exists to stop business owners from electing S Corp status right before a liquidation or sale to dodge double taxation.” - Mike Jesowshek, CPA


    “Holding onto your assets for five years after converting to an S Corp is the simplest way to avoid the Built-In Gains Tax.” - Mike Jesowshek, CPA


    “The BIG Tax is important to understand, but it’s not a reason to avoid an S Corp election. With the right planning, an S Corp is still a powerful tax-saving strategy.” - Mike Jesowshek, CPA


    Check out this episode’s blog post: https://www.taxsavingspodcast.com/blog/beware-of-hidden-built-in-gain-big-taxes-when-transitioning-to-s-corporation


    Click here to book a demo call or you can visit https://taxelm.com/demo/

    ______


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

    Join TaxElm: https://taxelm.com/


    -------


    Podcast Website: https://www.TaxSavingsPodcast.com

    Facebook Group: https://www.facebook.com/groups/taxsavings/

    YouTube: www.TaxSavingsTV.com


    Tax Q&A: Short-Term Rentals, 1099 Confusion, Entity Conversions, and Creative Tax Strategies Feb 12, 2025
    Show notes

    Have you ever considered how advanced tax strategies, from customized retirement contributions to optimizing home office deductions, might lower your overall tax burden?

    In this Q&A episode, host Mike Jesowshek answers listener questions on various tax topics. He covers issues ranging from retirement planning strategies, such as after‑tax contributions and Roth conversions in a solo 401(k), to the proper methods for paying oneself as a sole proprietor versus an S corporation. Mike also explains home office deductions, board meeting expenses, handling duplicate tax forms, and business entity conversions.


    [00:00 - 05:02] Retirement Contributions and Solo 401(k) Options

    • Mike discusses using after‑tax contributions and a Roth conversion in a solo 401(k) for high‑income earners.
    • New members receive immediate access to a comprehensive suite of tax-saving tools and consultations.


    [05:02 - 10:42] Owner Draws, Home Office Deductions, and Board Meeting Expenses

    • Mike explains how to oneself as a sole proprietor using owner draws versus payroll for S corporations.
    • Understand that taking money out of a business as an owner draws does not reduce taxable profit.
    • Ensure that business spaces are used exclusively for business, and document meetings carefully when using home space.


    [10:42 - 15:32] Hiring Family Members, Deducting Mileage Expenses, and Entity Conversion

    • Mike discusses claiming mileage expenses when an employee uses a personal vehicle for business.
    • Recognize that converting a C corporation back to an LLC may trigger taxable events; professional consultation is advised.


    [15:32 - 20:17] Handling Duplicate 1099 Forms and Short-Term Rental Deductions

    • Work with the issuer to correct mistakes or offset the extra reporting with a matching expense entry.
    • Understand the timing of deductions and whether expenses need to be capitalized based on service start dates.


    [20:17 - 27:20] S Corporation and Subsidiary Structures; Home Office with Additional Facility

    • Mike details the benefits of an S corporation holding company structure for multiple LLCs and addresses home office deductions when using a separate facility.
    • Proper structuring can consolidate profit and loss reporting, and the administrative office rule allows a home office deduction even when an additional business location exists.


    Direct Quotes:


    "If you are helping out family members, and those family members can also do some work for your business, why not get a business deduction for that help that you want to do anyways?" - Mike Jesowshek, CPA


    Check out this episode’s blog post! Visit https://www.taxsavingspodcast.com/blog/tax-q-a-short-term-rentals-1099-confusion-entity-conversions-and-creative-tax-strategies


    Click here to book a demo call or you can visit https://taxelm.com/demo/

    ______


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

    Join TaxElm: https://taxelm.com/


    -------


    Podcast Website: https://www.TaxSavingsPodcast.com

    Facebook Group: https://www.facebook.com/groups/taxsavings/

    YouTube: www.TaxSavingsTV.com



    2025 Tax Changes Every Small Business Owner Needs To Know Feb 05, 2025
    Show notes

    Are you making the most of the new 2025 tax changes, or could a simple tax strategy adjustment save you thousands?

    In this episode, Mike breaks down key tax changes for 2025 that small business owners need to know. He covers adjustments to tax brackets, increases in the standard deduction, new mileage rates, retirement contribution limits, and updates to gift and estate tax exclusions. He explains how these changes impact tax planning, emphasizing strategies to optimize deductions and avoid unnecessary tax burdens. Additionally, he highlights potential future tax changes with the incoming administration and the importance of staying updated.


    [00:00 - 05:21] Understanding the 2025 Tax Brackets

    • Tax brackets adjust annually for inflation, ensuring more income is taxed at lower rates.
    • Mike explains how tax brackets work and why crossing into a higher bracket doesn’t mean all income is taxed at that rate.
    • Knowing your tax bracket can help with strategic tax planning, such as Roth conversions and deductions.


    [05:22 - 10:24] Mileage Deduction Increase for 2025

    • Mike discusses when to use the mileage method versus actual expenses for vehicle deductions.
    • Choosing the right deduction method (mileage vs. actual expenses) depends on vehicle costs and business mileage.


    [10:25 - 14:44] Standard Deduction Updates

    • The standard deduction increases to $30,000 for married filers and $15,000 for single filers.
    • How can this impact taxpayers deciding between itemized and standard deductions?
    • Most taxpayers will benefit from the standard deduction, but strategic "bunching" of itemized deductions can provide tax advantages.


    [14:45 - 18:53] Retirement Contribution Limits Increase

    • Employee 401(k) contribution limit rises to $23,500, while IRA limits remain at $7,000.
    • Maximizing retirement contributions helps reduce taxable income and build financial security.


    [18:54 - 21:53] Gift & Estate Tax Changes

    • The gift tax exclusion increases to $19,000 per recipient.
    • Estate tax exemption rises to $13.99 million, affecting wealth transfer planning.
    • Strategic gifting can help reduce taxable estates and transfer wealth efficiently.
    • Proactive tax planning ensures business owners take advantage of new tax laws while avoiding potential pitfalls.


    Quotes:


    “Simply going into a new tax bracket doesn’t mean all of your income is taxed at that higher rate.” - Mike Jesowshek, CPA


    “More of your income being taxed at a lower rate is good news—it means you’re keeping more of what you earn.” - Mike Jesowshek, CPA


    Click here to book a demo call or you can visit https://taxelm.com/demo/


    ______


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

    Join TaxElm: https://taxelm.com/


    -------


    Podcast Website: https://www.TaxSavingsPodcast.com

    Facebook Group: https://www.facebook.com/groups/taxsavings/

    YouTube: www.TaxSavingsTV.com



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