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.

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.

👉 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) The Augusta Rule: What’s a Reasonable Rental Rate?
How to properly rent your home to your business, why documentation matters, and whether to use hotel comps or Airbnb rates.

(03:00) Hiring Foreign Contractors: W-8 vs W-9
What forms you need on file when paying international contractors and when 1099s apply.

(04:30) Partnership Owners: Should You Use an S Corp?
How S Corps can reduce self-employment tax, why ownership structure matters, and how to structure it correctly.

(09:00) Business Expenses Paid from a Personal Account
Can you still deduct them? What co-mingling means during an audit, and how to fix it going forward.

(12:00) Do Insurance Companies Need Your Subcontractor’s Tax Return?
Why a signed W-9 is typically all you need and how to protect yourself.

(14:00) Can I Deduct Free Food? Restaurant and Bar Tax Rules
How to deduct employee meals and promotional giveaways correctly. Cost vs retail value explained.

(17:00) FSA vs HRA: Which One Actually Makes Sense?
When high out-of-pocket medical costs justify setting up an HRA and what thresholds to consider.

(19:00) $10 Million in a C Corp: Smart Strategy or Tax Trap?
The personal holding company rules, double taxation, and when retaining earnings in a C Corp actually makes sense.

(22:00) Free Resources for New Business Owners
Where to start if taxes feel overwhelming and how to build a foundation before filing.

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.

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 strategically, reduce taxes, and increase your impact.

👉 Ready to turn your charitable giving into a real tax strategy? Open a donor-advised fund with Daffy and start giving more strategically today: https://www.daffy.org/taxsavings/invite

👉 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) What Is a Donor-Advised Fund?

The basics: how DAFs work as a tax-advantaged account for charitable giving, similar to a 401(k) for retirement.

(04:45) Tax Deduction Limits: 60% for Cash, 30% for Stock

How much you can deduct from your AGI and why bonuses, windfalls, and liquidity events are ideal times to use a DAF.

(06:30) Why DAF Donations Are Irrevocable (One-Way Trip)

Understanding that donor-advised funds are 501(c)(3) charities and why you cannot take the money back.

(09:00) The Double Tax Win of Donating Stock

How donating appreciated stock gives you a full market value deduction and eliminates capital gains taxes.

(11:30) The New 0.5% AGI Floor and Bunching Strategy

How the recent tax law created a deduction floor and why bunching multiple years of giving into one high-income year makes sense.

(15:00) How to Actually Use a DAF Day-to-Day

The mechanics of contributing, distributing to multiple charities, and setting up recurring donations.

(20:45) Setting Up a DAF in Under 60 Seconds

The simple setup process, Daffy's flat monthly fee structure, and how it compares to percentage-based pricing models.

(28:30) Investment Options and Portfolio Control

How donated funds are invested tax-free and what level of control donors have over portfolios.

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.

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 payroll returns, and a critical but often-missed strategy involving self-employed health insurance and HSA contributions that can reduce FICA taxes.

If you’re an S Corp owner trying to pay yourself the right way and avoid IRS attention, this episode walks you through exactly how to do it.

👉 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) The Reasonable Salary Requirement for S Corps
Why S Corp owners must take W-2 payroll and why determining reasonable salary is the first step.

(03:10) Payroll Software and Filing Requirements
Why using payroll software matters and how missed filings create serious problems.

(04:00) Monthly and Biweekly Payroll Explained
How spreading your salary evenly works and why this is the most common recommendation.

(05:30) True-Up Payroll. Quarterly and Annual Options & Cash Flow Risks
How quarterly and annual true-ups work and how draws get reclassified as wages. Large quarterly tax payments can create cash crunches.

(08:45) Zero Payroll Returns and Compliance Traps
Why you still need to file payroll returns even when no payroll is run.

(09:30) Catch-Ups, Slowdowns, and Bonus Payrolls
How to adjust payroll when income, workload, or profitability changes.

(11:45) Self-Employed Health Insurance and HSA Adjustments
How S Corp owners can increase reasonable salary without paying extra FICA taxes.

(15:30) The Safest Payroll Strategy for Most Owners
Why consistent payroll timing protects cash flow and reduces IRS risk.

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.