Send us a text

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Most people think an HSA is just for doctor visits—but it’s actually one of the most powerful retirement tools available. In this episode, Mike breaks down how to use your Health Savings Account to save on taxes, grow your money, and even invest for the future. If used right, it’s like a secret weapon for building wealth.

Chapters:

(00:32) What is an HSA?

Mike explains how an HSA works, what makes it different from an FSA, and what medical expenses qualify.

(01:35) The Triple Tax Benefit

You get a deduction when you put money in, tax-free growth, and tax-free withdrawals if used right.

(03:50) HSA Contribution Limits for 2025

Learn how much you can contribute depending on whether you have an individual or family plan.

(05:04) HSA Eligibility Rules

Mike walks through what qualifies as a high-deductible health plan and other requirements you must meet.

(07:23) How to Use an HSA for Retirement

This part explains how to grow your HSA like a retirement fund by investing and saving receipts.

(10:05) Avoid the Withdrawal Penalty

If you withdraw funds the wrong way, you’ll pay penalties—unless you follow these simple rules.

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

🚀 Visit https://taxelm.com/webinars/ to save your seat!

On May 14 at 2 PM EST, join Mike for a live webinar to unveil a brand-new feature inside TaxElm that will transform the way small business owners approach tax planning. It’s simple, powerful, and built specifically for real business owners who want less stress and more clarity when it comes to their taxes.

Here’s what you’ll learn in the webinar:

• How this new TaxElm feature simplifies your tax planning process
• Why it’s designed for entrepreneurs—not accountants
• How to use it to build a smarter, more proactive tax strategy

🎯 Save your spot now: www.taxelm.com/webinars

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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/

What if everything you thought you knew about retirement planning was just scratching the surface? In this episode, Mike sits down with retirement expert Matt Ruttenberg to break down advanced retirement strategies that go way beyond the traditional 401(k).

Chapters:

(01:22) Understanding the Retirement Plan Stack
How business owners can layer a safe harbor 401(k), profit sharing, and cash balance plan to maximize tax savings while customizing benefits for themselves vs. employees.

(04:55) High-Income Dentist Case Study ($750K Income)
How a 50-year-old dentist can contribute over $200K pre-tax annually, avoid costly employee contributions, and potentially boost deductions by another 35% using life insurance inside a cash balance plan.

(11:36) The Qualified Swap Strategy
Using IRS Code §7702 to mimic a Roth account by funding a life insurance policy inside a qualified plan, then legally moving it out tax-free after five years.

(15:20) Online Consultant Case Study (Retire by Age 50)
How a 42-year-old solo S-Corp owner can combine a self-directed solo 401(k), mega backdoor Roth, and future Roth conversions to retire early while minimizing taxes on withdrawals.

(21:40) Real Estate Investing Inside a 401(k)
How self-directed plans can allow for non-traditional investments like crypto or property.

(26:44) Real Scenario #3: Seasonal Landscaping Business

How solo 401(k)s can be used even with employees (if structured right)

(34:12) When to Use Non-Qualified Retirement Plans
Non-qualified plans can help business owners bypass traditional testing requirements and reward only specific employees, without triggering mandatory contributions across the board.

(39:01) How to Properly Design a Life Insurance Plan
Why poor design ruins tax benefits and how to build a policy that acts like a Roth

(45:30) Common Misunderstandings Around 401(k) Plans
Why many business owners avoid retirement plans due to misconceptions about complexity or cost.

(48:16) Matching the Right Plan to the Right Goal
How to choose between a traditional 401(k), profit sharing, cash balance, or non-qualified plan depending on your goal.

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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/

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.

[01:08] 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.

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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/

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.

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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