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.