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PODCAST

Small Business Tax Savings Podcast

Mike Jesowshek, CPA

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:

business entrepreneurship

All Episodes

20:05

2026 Tax Updates Every Business Owner Needs to Know

Small Business Tax Savings Podcast ·

2026/04/08

Every year, the IRS updates important tax numbers, that most business owners miss. This leads to missed deductions, poorly timed income decisions, and unnecessary overpayments to the IRS. In this episode, we break down the most important 2026 tax updates business owners need to know, including changes to tax brackets, standard deductions, Social Security wage caps, retirement limits, HSA contributions, mileage rates, capital gains thresholds, and Section 179 expensing. 👉 Get the Fre...

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14:24

Quarterly Estimated Taxes 101 (How to Stop Overpaying...

Small Business Tax Savings Podcast ·

2026/04/01

Estimated taxes should not feel like a guessing game, but for many business owners, they do. Underpay, and you face stress, penalties, and a big bill in April. Overpay, and you hand the IRS more cash than needed, limiting what you can reinvest in your business. In this episode, we break down how estimated taxes actually work, why the U.S. tax system is pay-as-you-earn, and how to avoid both overpaying and underpaying. We cover the safe harbor rules, why accurate bookkeeping matters, and how...

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34:07

Are You Going to Jail for Tax Planning? Tax Attorney...

Small Business Tax Savings Podcast ·

2026/03/25

Are you worried a tax strategy could land you in trouble with the IRS? In this episode, Mike Jesowshek sits down with tax attorney Ed Lyon to break down what tax risk actually means. They explain why most business owners do not get in trouble for smart tax planning, where the line between gray-area strategy and fraud really sits, and why proper implementation matters just as much as the strategy itself. They cover audit risk, common red flags, what to ask before moving forward wit...

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19:08

Hiring Your First Employee? Don’t Make These...

Small Business Tax Savings Podcast ·

2026/03/18

You’ve hired your first employee… Now what? Hiring your first employee introduces a new layer of tax responsibility, compliance, and systems that many business owners are not prepared for. You are now managing payroll taxes, filings, labor laws, and deadlines that carry real penalties if handled incorrectly. In this episode, we break down exactly what happens after you hire your first employee so you can avoid costly mistakes and set your business up to scale the right way. We cover the...

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23:20

Why Filing an Extension Is the Smarter Move for...

Small Business Tax Savings Podcast ·

2026/03/11

Filing a tax extension feels stressful for many business owners. Missing numbers, unfinished bookkeeping, and uncertainty about the tax bill can make tax season overwhelming. But filing an extension (in many cases) can be the smartest move you can make. A tax extension gives you more time to file your return so you can organize your records, receive missing documents like K-1s, and avoid rushing through a return that could contain mistakes. In this episode, we break down how extensions actual...

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21:03

New Charity Tax Rules in 2026. How the One Big...

Small Business Tax Savings Podcast ·

2026/03/04

Charitable giving rules are changing in 2026, and many business owners have no idea their tax deductions could quietly shrink. The One Big Beautiful Bill Act introduced new limits, floors, and deduction caps that change how charitable donations work depending on your income level and whether you itemize deductions. In some cases, you could donate the exact same amount and receive a smaller tax benefit than before. Today we're breaking down the new charitable giving tax rules, who wins under t...

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17:52

Broke Even at the Casino? You Still Owe Taxes in 2026...

Small Business Tax Savings Podcast ·

2026/02/25

Imagine breaking even at the casino and still owing taxes. Beginning in 2026, Congress approved a new rule that limits gambling loss deductions to 90%. That means if you win $10,000 and lose $10,000, you could still owe taxes on $1,000 of phantom income. Today, we're breaking down the new gambling tax rule that quietly slipped into law, why it creates phantom income for gamblers, and what casual and professional gamblers need to do right now to protect themselves. 👉 Get the Free Tax Savings

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26:44

He Put $5M in a C Corp to Avoid Taxes… Was That...

Small Business Tax Savings Podcast ·

2026/02/18

Can you deduct free food, rent your house to your business or avoid double taxation with a C Corp? In this Q&A episode, Mike answers rapid-fire tax questions submitted by business owners across industries. From restaurant deductions to partnership restructuring, foreign contractors, co-mingled expenses, and advanced C Corp investing strategies, this episode walks through what’s legal, what’s smart, and what’s risky. If you want clarity before you file, this is the one to listen to. 👉

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34:18

Are You Donating Wrong? How Donor-Advised Funds...

Small Business Tax Savings Podcast ·

2026/02/11

If you're already giving to charity, you're leaving thousands of dollars in tax deductions on the table. What is a donor-advised fund and why should you care? Mike sits down with Adam Nash, CEO of Daffy, to break down how Donor-Advised Funds (DAFs) work and why they can be a powerful tax strategy for business owners and high-income earners. If you regularly give to your church, your kids’ school, your alma mater, or other charities, this episode shows you how to give more strategi...

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17:47

How Often Should S Corp Owners Run Payroll | Payroll...

Small Business Tax Savings Podcast ·

2026/02/04

When should you pay yourself? Paying yourself on the wrong payroll schedule can create IRS red flags, cash flow crunches, and painful cleanup later. In this episode, we break down monthly, quarterly, and annual payroll for S Corp owners. You’ll learn what the IRS actually expects, how reasonable salary works, why quarterly “true-ups” can create cash flow problems, and how to structure payroll to stay compliant without overpaying in taxes. We also cover catch-ups, slowdowns, bonuses, zero pa...

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12:13

How to Pay Yourself as an LLC Owner in 2026

Small Business Tax Savings Podcast ·

2026/01/28

Paying yourself wrong can trigger IRS issues, messy books, and unexpected tax bills. In this episode, we break down exactly how LLC owners should pay themselves in 2026 based on their entity type and tax election. You’ll learn the 3 primary ways business owners get paid: owner draws or distributions, payroll, and guaranteed payments. We explain which payment methods are legally allowed for single-member LLCs, partnerships, and S corporations, and why running payroll as an owner is prohi...

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15:22

The 10 LLC Mistakes That Can Destroy Your Business

Small Business Tax Savings Podcast ·

2026/01/21

You formed your LLC. Good job. But many business owners unknowingly make critical mistakes after formation that quietly destroy liability protection, trigger audits, and limit growth. In this episode, Mike walks through the 10 most common LLC mistakes business owners make in 2026 and explains exactly how to fix them. From mixing personal and business finances to ignoring tax planning and misclassifying owner compensation, this episode gives you a practical framework to audit your business a...

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10:28

How to Set Up an LLC in 2026 for Free (Step by Step)

Small Business Tax Savings Podcast ·

2026/01/14

Thinking about forming an LLC in 2026? In this episode, Mike breaks down how to set up an LLC step by step, what “free” really means, state filing costs, common mistakes to avoid, and why an LLC can act as an insurance policy for future S Corp tax savings. Perfect for new and growing business owners who want clarity without the confusion. If you want a clean, simple business setup that protects you now and gives you flexibility later, this episode gives you the roadmap without the legal confu...

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15:13

Welcome to 2026: Make These 4 Financial Moves Right Now

Small Business Tax Savings Podcast ·

2026/01/07

If you are already behind on your taxes in January, there are four tax tasks you cannot skip. In this episode, we break down the four financial tasks every business owner needs to complete in January to start 2026 clean and organized. Mike explains why unfinished bookkeeping leads to missed deductions and unnecessary stress, how to properly review your financials, and why most tax issues begin long before filing season. We also cover the importance of creating a simple financial summary docum...

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17:14

The 1099 Rules Every Small Business Owner Needs to...

Small Business Tax Savings Podcast ·

2025/12/31

Are you still guessing when it comes to 1099s? Most business owners are. And every January, that confusion turns into stress, penalties, and last-minute cleanup that could have been avoided. In this episode, Mike Jesowshek breaks down everything small business owners need to know about 1099-NEC and 1099-MISC forms, who needs one, who doesn't, the deadlines and the penalties that add up fast. If you want January to feel calm instead of chaotic, this episode gives you the clear rules and ...

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4:47

Merry Christmas and Thank You for Listening!

Small Business Tax Savings Podcast ·

2025/12/24

Send us a text Happy Holidays, and thank you. This episode is a personal thank-you to the Small Business Tax Savings Podcast community. We reflect on nearly eight years of the show, including over 400 episodes and more than 1.5 million downloads. At the core of this podcast is one mission; Helping small business owners pay the least amount in taxes legally, without stress or confusion. Let’s make 2026 the year you get proactive about tax planning from the start. If thi...

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22:24

The Biggest Tax Planning Mistakes Business Owners...

Small Business Tax Savings Podcast ·

2025/12/17

Send us a text 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 retire...

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22:13

Q&A | LLC or Not, Home Office vs Augusta Rule, and...

Small Business Tax Savings Podcast ·

2025/12/10

Send us a text 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 t...

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26:40

Year-End Tax Strategies Every Business Owner MUST Do...

Small Business Tax Savings Podcast ·

2025/12/03

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. ...

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20:51

Write It Off Now. Depreciation, Capitalization...

Small Business Tax Savings Podcast ·

2025/11/26

Send us a text What if you could buy a computer, a machine, or new equipment and deduct the entire cost in the first year instead of waiting 5, 10, or even 30 years? Thanks to major updates in the One Big Beautiful Bill, you can now take a full write-off upfront. We break down how depreciation works, when to expense versus capitalize, and how the updated bonus depreciation and Section 179 rules give owners more control over their tax bill. You’ll learn how to time asset purchases, when to avo...

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405 results

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