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.

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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

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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 🙏

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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.