Jay Two smart October tax strategy moves

By: Jay Parks

Slot machine showing all 7's.

Running a business means staying ahead of the game, not just in your industry, but with the IRS, too. Two major tax changes deserve your attention as we enter the last quarter of 2025. One is surprising (yes, it's about gambling), and the other could save your business thousands if you act fast.

Let's break it down.

If you're gonna gamble, do it before New Year's Eve

Okay, I'm only half-joking here.

Under current federal tax law, if you win money gambling in 2025, whether it's slots, poker, sports betting, or horse racing, you can deduct 100% of your gambling losses, but only up to the amount you won.

So if you won $10,000 and spent $13,000 getting there (which is how gambling usually goes), you can deduct $10,000 in losses and report $0 in net winnings. The remaining $3,000 is gone—no deduction, no refund. But it's still a clean break.

Next year, you'll only be allowed to deduct 90% of your gambling winnings, not 100%. That means even if you lost more than you won, you'll still owe tax on 10% of your winnings.

So, if gambling is your thing? Do it this year, and be done with it. January 1 is too late.

Heads up for parents: Gambling winnings can hurt your student's federal financial aid eligibility. It shows up as income even if you blew it all trying to win it. Same goes for health insurance subsidies through the marketplace. I've seen more than one client caught off guard by this.

To be clear, this is federal law. States like Oklahoma don't play nice with gambling deductions, and that's a whole other issue.

Bonus depreciation is back at 100% (but you need to plan now)

Now for the good news.

As part of the new Big Beautiful Bill, bonus depreciation is back at 100% for certain business asset purchases, but only for assets placed in service after January 19, 2025.

That's a big shift from where we were. In 2024, bonus depreciation was only 40%, phasing out fast. This new change? Permanent.

What qualifies?

  • Office equipment (like that new computer or copier)

  • Furniture and fixtures

  • Certain vehicles (keyword: qualifying)

  • Software

  • Machinery

And yes, that new office couch could count, if it meets the business use test.

If you want to take advantage of 100% bonus depreciation, October is the time to act. Here's why:

  • Lead times for vehicles and equipment are long

  • Delays can bump deliveries into 2026 (no deduction!)

  • Special orders or custom equipment require planning

Reminder: You can finance the asset and still write off 100% this year. Paying cash isn't required, but placing the asset in service before year-end is.

Two tax tracks: How you pay vs. How you write off

Here's something most business owners miss:

There are two timelines you need to keep in mind when you buy something for your business:

  • How you pay for it — cash, credit, financing

  • How you depreciate it — slow and steady or all at once

These don't have to match.

  • Finance a vehicle over 5 years, but write it off in one

  • Pay cash for a computer and still depreciate it slowly

The bonus depreciation option gives you flexibility. Use it wisely, especially before December 31.

The bottom line: Get strategic before year-end

Whether you're feeling lucky or planning your next business upgrade, October is the time to act intentionally and protect your bottom line.

So if you've got assets to buy, or you're still trying to write off that slot machine streak from summer vacation, this is your reminder: Plan now, or pay more later.

Need help timing your deductions or planning purchases?

Let's talk. My team and I are happy to explain what qualifies and what could cost you more in 2026.