Every business owner hits a point where the tax questions start stacking up.

Can I deduct this? Should I switch to an S Corp? Is this still a business if I have not made money yet? And what happens if I did something before I had my systems set up the right way?

In this episode, Mike opens the floor to questions from business owners and breaks down the tax answers behind them. From zero-activity LLC filings and Schedule C concerns to family payroll planning, vehicle deductions, and rental strategies like the Augusta Rule, this episode covers the practical decisions that shape how much tax you pay and how well your strategy holds 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

(03:22) Do You Need a CPA for a Zero-Activity Partnership Return?
A new LLC owner asks about filing a Form 1065 with no business activity. Mike breaks down why even a zero return can be more complex than it looks and what to consider before self-filing.

(04:47) Can a First-Year Business Loss Offset W-2 Income?
Mike walks through hobby loss concerns, material participation rules, and when a side hustle loss may be used to reduce taxes on other income.

(06:35) Is an S Corp Worth It at $120,000 of Profit?
This section covers the tradeoff between added payroll and tax prep costs versus potential self-employment tax savings, along with the importance of setting a reasonable salary.

(12:01) Where Can You File Business Taxes Online Yourself?

For business owners thinking about self-filing, Mike shares general software options and explains why second eyes matter on more complex returns.

(13:12) Can You Deduct Business Expenses Paid on a Personal Credit Card?
Mike answers a common startup question and explains how to handle valid business expenses paid personally before a business bank account is opened.

(14:27) How Does the Family Management Company Strategy Work?
This section breaks down how business owners with an S Corp may use a separate sole proprietorship to hire children, reduce payroll taxes, and stay compliant.

(20:56) How Does the Augusta Rule Work for Business Owners?
Mike explains how the Augusta Rule works, what records you need, and how to back it up in an audit.

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.

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 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

(00:52) Why IRS Tax Numbers Change Every Year
Tax brackets, standard deductions, retirement limits, Social Security wage caps, HSA limits, and mileage rates are adjusted annually based on inflation and tax policy changes.

(01:24) 2026 Standard Deduction and Why It Matters
The new standard deduction amounts affect whether it makes sense to itemize and also shape strategies like hiring your children, since income below the standard deduction may avoid federal income tax.

(06:12) The 2026 Social Security Wage Cap
Wages are subject to Social Security tax only up to the annual wage cap, which makes this number especially important for payroll planning and S Corp salary decisions.

(08:15) Retirement Contribution Limits for 2026
Updated IRA and 401(k) contribution limits create new opportunities for tax deductions, especially for business owners using retirement plans to reduce taxable income.

(09:43) 2026 HSA Contribution Limits and Why HSAs Are So Powerful
HSA contribution limits increased for 2026, and the account remains one of the most tax-advantaged tools available because contributions, growth, and qualified withdrawals all receive favorable tax treatment.

(11:13) 2026 Mileage Rate Increases
The higher mileage rate can create a larger deduction for business owners who use the standard mileage method, making accurate mileage tracking even more important.

(12:57) Capital Gains Tax Thresholds for 2026
Long-term capital gains are taxed under a separate set of thresholds, which makes timing important when selling investments, real estate, or a business.

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.

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 to build a smarter system for quarterly payments that improves cash flow and reduces surprises.

👉 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

(02:15) Why Business Owners Fall Behind on Quarterly Taxes
Without an employer withholding taxes, business owners are responsible for making estimated payments themselves, and many ignore them until penalties and interest build up.

(03:45) Why Last Year’s Income Is Not Enough
Many business owners base estimated taxes on last year’s income or send in whatever feels safe, but income, deductions, entity structure, and tax law can all change.

(04:30) The Safe Harbor Rules You Need to Know
To generally avoid underpayment penalties, you need to pay 100% of last year’s tax liability, 110% for certain higher-income earners, or 90% of this year’s tax liability.

(06:30) The Cash Flow Cost of Overpaying and Underpaying
Overpaying estimated taxes can tie up money that could be used for marketing, debt reduction, equipment, or other business needs, only to result in a refund later, while underpaying creates pressure when tax time comes, especially if business profits rise and estimated payments were never adjusted upward during the year.

(08:40) How to Calculate Estimated Taxes More Strategically
The process starts with a quarterly profit analysis, then projecting the rest of the year forward, and finally adjusting payments intentionally based on current numbers.

(10:40) Estimated Tax Due Dates Every Business Owner Should Know
Quarterly estimated tax payments follow a set schedule throughout the year, and knowing those due dates is essential for staying compliant and avoiding surprises.

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.

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 with an advanced strategy, and how business owners should think about their own risk tolerance when building a tax plan.

👉 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

(02:00) Why Business Owners Fear Tax Planning
People don't go to jail for legal tax planning. They go to jail for fraud, lying, and backdating documents.

(05:00) Why Tax Strategies Exist in the First Place
The tax code is designed to encourage certain behavior. Congress uses tax incentives to push homeownership, healthcare benefits, investing, and charitable giving.

(12:00) When a Legal Strategy Becomes Illegal
A strategy can be perfectly valid in theory, but fail when implemented poorly.

(24:00) How to Vet an Advanced Tax Strategy
When someone pitches an advanced strategy, transparency matters. Ed explains what questions to ask, what red flags to look for, and why business owners need to understand who they are dealing with before moving forward.

(27:00) How Business Owners Should Think About Risk
Tax risk is just another business risk. The real goal is to understand your own risk tolerance, know where your advisor falls on the conservative-to-aggressive spectrum, and make informed decisions.

(31:00) A Favorite Strategy for the Right Client
Ed closes by sharing one tax strategy he likes for the right candidate, the charitable lead trust, and explains why the best strategy always depends on the client’s goals, income, and long-term plan.

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.

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 difference between W2 employees and 1099 contractors, the real cost of payroll taxes, how to stay compliant with state and federal requirements, and why payroll software is a must.

👉 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

(01:00) Employee vs Contractor: What the IRS Looks At
Classification comes down to control. Who sets hours, pay, tools, and how the work gets done determines W2 vs 1099.

(04:00) The Payroll Tax Reality Business Owners Miss
Hiring an employee makes you a tax middleman responsible for withholding and paying multiple taxes.

(06:00) What You Need Before Running Payroll
You need an EIN, state withholding accounts, unemployment accounts, and workers’ compensation set up first.

(07:30) Why Payroll Software Is Non-Negotiable
Payroll software handles tax calculations, filings, deposits, and compliance to avoid penalties and costly mistakes.

(09:30) The Risk of Missing Payroll Tax Deadlines
Late payments trigger immediate penalties and interest, and payroll mistakes can shut down businesses.

(12:00) Benefits Without Breaking the Bank
Health reimbursement arrangements and simple retirement plans offer affordable ways to provide benefits.

(14:30) Hiring Employees in Other States
Out-of-state hires require additional registrations, tax accounts, and possible foreign entity filings.

(16:00) Key Takeaways
Hiring is a growth milestone. Set up systems correctly, use payroll software, and build processes that allow your business to run without you.

Need payroll software? We recommend https://gusto.com

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.

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 actually work, clear up common myths about audit risk, and explain what to do if you cannot afford your tax bill.

We also cover why ignoring the IRS is the worst move you can make, how penalties work, and the payment plan options available to business owners who need more time to pay what they owe.

👉 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

(02:30) Key Tax Deadlines Every Business Owner Should Know
Partnerships and S corporations file by March 15. Personal returns and C corporations file by April 15.

(04:00) What a Tax Extension Actually Means
A tax extension gives you more time to file your return, but your taxes are still due by the original deadline.

(05:30) Common Myths About Filing a Tax Extension
Extensions do not increase audit risk, and many high income taxpayers file them every year.

(07:00) The Most Common Reasons Business Owners File Extensions
Unfinished bookkeeping, waiting on K-1 forms, or planning opportunities like retirement contributions or cost segregation.

(11:00) The Cost of Not Filing Your Tax Return
Failure to file penalties can reach hundreds of dollars per owner per month for business entities.

(13:00) Why You Should Still Estimate and Pay Taxes With an Extension
Making an estimated payment reduces penalties and interest if you expect to owe.

(15:30) What to Do If You Cannot Afford Your Tax Bill
The IRS offers short term payment plans, installment agreements, and other options if you communicate.

(20:00) Key Takeaways
Tax extensions are not a red flag. Used correctly, they give business owners time to plan, reduce mistakes, and stay in control of their tax situation.

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.

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 the new system, who loses, and how smart business owners can still give generously while protecting their tax strategy.

👉 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

(01:00) Charity First, Strategy Second
Giving should start with the causes you care about before considering tax benefits.

(02:00) Current Deduction Rules and AGI Limits
How itemized deductions work and the limits for cash, appreciated assets, and non-cash donations.

(04:20) New Deduction for Non-Itemizers
Starting in 2026, standard deduction filers can deduct up to $1,000 (single) or $2,000 (married) in cash donations.

(07:00) The New 0.5% AGI Deduction Floor
Itemized charitable deductions only apply to donations above 0.5% of AGI.

(09:40) Deduction Cap for High-Income Earners
Taxpayers in the top bracket now receive a maximum 35% tax benefit from itemized deductions.

(11:00) How Business Owners Handle Charitable Giving
Most charitable contributions flow through to the owner’s personal tax return.

(13:30) Planning Strategy: Bunching Donations
Combining multiple years of giving into one year may increase deductions.

(16:00) Planning Strategy: Qualified Charitable Distributions
Taxpayers age 70½ and older can donate from an IRA to bypass itemized deduction limits.

(17:00) Key Takeaways
Charitable giving rules are more complex in 2026. Strategic planning helps preserve the tax benefits.

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.

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 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

(00:00) The Tax Trap Nobody's Talking About

How the One Big Beautiful Bill created a situation where breaking even at the casino still leaves you with a tax bill, and why every gambler needs to pay attention.

(00:45) The Old Rule: How Gambling Losses Used to Work

If you itemized and broke even, no tax. If you took the standard deduction, losses did not count.

(02:00) The New 90% Rule & Phantom Income

Starting in 2026, only 90% of your losses are deductible, even if you itemize. Win $10,000, lose $10,000, and you're now paying tax on $1,000 you never kept. That's phantom income, and it's the new reality.

(04:00) Professional Gamblers: It Gets Worse

Pro gamblers file on Schedule C and can deduct business expenses like travel and lodging. But losses plus expenses cannot exceed gambling income. They cannot offset other income, cannot carry losses forward, and starting in 2026, the 90% loss cap applies to them too.

(09:00) Good News: The W-2G Threshold Finally Goes Up

The slot reporting threshold rises from $1,200 to $2,000 in 2026 and will adjust for inflation. This does not change what you owe. All gambling income is still reportable. It only reduces the number of W-2Gs issued.

(10:00) Record Keeping: Your Most Important Tool Right Now

Casino reports can overstate income. Keep your own log with the date, casino, type of wager, and net win or loss per session. Track sessions, not individual bets.

(12:30) Key Takeaways

All winnings are taxable. Losses only offset if you itemize. The 90% cap creates phantom income. Plan under current law.

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.