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.

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 prohibited unless you have an S corporation election.

We walk through how each method is taxed, how it shows up in your financial statements, and why owner draws do not reduce business profit even though they reduce cash.

👉 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

(00:45) Why Paying Yourself Correctly Matters
Improper owner pay can create audit risk, illegal compensation setups, and accounting problems that surface later during tax season.

(01:25) Owner Draws and Distributions Explained
What an owner’s draw actually is, how it works, why no taxes are withheld upfront, and why draws don’t reduce business income.

(02:55) Guaranteed Payments for Partnerships
How guaranteed payments work in partnerships, when they’re used, how they’re taxed, and why they’re different from draws.

(04:10) Paying Yourself as a Single-Member LLC
Why single-member LLC owners can only take owner draws, and why running payroll to yourself is not allowed by law.

(05:05) Paying Yourself in an LLC Partnership
The two legal options for partners.

(06:00) Paying Yourself as an S Corp Owner
Why S Corps require a reasonable salary, how payroll and distributions work together, and where tax savings come from.

(07:00) How to Document Owner Pay Correctly
How draws hit the balance sheet, how payroll hits the income statement, and why documentation matters for audits.

(09:30) What to Do Next as an LLC Owner
How to choose the right pay method, set up a system, plan for taxes, and avoid common compensation mistakes going forward.

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 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 and protect it the right way.

If you want your LLC to survive and thrive, not just exist on paper, this episode shows you what to fix now before it becomes expensive later.

👉 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) Mixing Personal and Business Finances
Why commingling funds breaks liability protection and how to properly separate accounts without overcomplicating things.

(02:00) Failing to Maintain LLC Compliance
Annual reports, renewals, and filings business owners forget that can cause administrative dissolution.

(03:20) Ignoring the S Corporation Opportunity
How LLC owners overpay self-employment taxes by not exploring an S Corp election at the right time.

(04:10) Misclassifying Owner Compensation
The difference between owner draws and W2 payroll, and why paying yourself the wrong way creates tax problems.

(05:45) Operating in the Wrong State
Why forming an LLC in one state but operating in another requires foreign registration.

(06:40) Skipping Tax Planning
Why taxes are often a business owner’s biggest expense and how proactive planning changes everything.

(07:30) Failing to Update State Filings
What happens when partners, addresses, or business purposes change and filings are not updated.

(08:10) Treating the LLC Like a Hobby
How hobby loss rules work and why consistent losses without profit motive raise red flags.

(09:00) The LLC Audit Checklist
Simple steps to audit your LLC today, fix weak spots, and build better habits going forward.

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.

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 confusion.

👉 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) Why Form an LLC in 2026
The 3 core reasons business owners form LLCs. Liability protection, credibility, and flexibility for future tax planning.

(02:10) Why an LLC Is an Insurance Policy for an S Corp
How an LLC allows you to elect S Corp status later and why sole proprietors do not have that option.

(03:00) What “Free” LLC Setup Really Means
State filing fees, unavoidable costs, and what online “free” services actually do.

(03:55) The Step-by-Step LLC Setup Process
Choosing a business name, selecting a registered agent, drafting an operating agreement, filing with the state, getting an EIN, and opening a business bank account.

(06:05) The Biggest LLC Mistakes Business Owners Make
Why not using the LLC, mixing funds, missing renewals, and following bad internet advice cause legal and tax issues.

(07:40) Bonus Tips to Strengthen Your LLC
Operating agreements, separating finances, tracking expenses, and setting up bookkeeping the right way.

(08:30) When to Consider an S Corporation
$50,000 in profit is a common tipping point and how an LLC makes the transition easier.

(09:00) Final Takeaway
How to use an LLC to protect yourself today while setting up smarter tax planning for the future.

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 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 document, meeting the January 31 1099 deadline, and building a proactive tax plan early in the year instead of scrambling in December.

If you want 2026 to be more profitable and less stressful, this episode shows you exactly where to start.

👉 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

(00:37) Close Out 2025 Before You Move Forward
Why unfinished bookkeeping follows you into the new year.

(01:00) How to Review Your Books the Right Way
What to check in your income statement and balance sheet for accuracy.

(02:55) How to Organize Tax Documents Properly
Why storing receipts and records now saves stress later.

(03:50) The Financial Summary Document Every Owner Needs
A simple snapshot that shows assets, liabilities, and insurance in one place.

(06:36) Why Advisors Love This One Document
How it leads to better advice, faster decisions, and smarter planning.

(08:00) The January 31 1099 Deadline
Who needs a 1099, who does not, and what payments count.

(11:07) Implementing Tax Strategies Throughout the Year
Why spreading strategies across the calendar leads to real savings.

(13:24) The Bottom Line for a Strong 2026
Clean books, clear visibility, timely filings, and a tax plan that works.

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.