Accounting in the Wild

Overtime Deduction, Trump Accounts & 1099 E-Filing — Big Beautiful Bill Updates

Jason Dinesen

Jason’s back with a grab bag of timely tax and accounting updates pulled straight from his teaching sessions and client questions.

In this episode of Accounting in the Wild, you’ll hear about:

  • Big Beautiful Bill (BBB) — the brand-new overtime pay deduction, how “qualifying overtime” is defined under the Fair Labor Standards Act, and why W-2s aren’t changing in 2025 (but employers still have new reporting duties).
  • Trump Accounts — what they are, how they work, and the unanswered questions around the $2,500 employer contribution rule.
  • Electronic filing of 1099s — the difference between the IRS FIRE and IRIS systems, plus when using a third-party provider might make sense.
  • 1099-K reporting threshold — BBB restores the 200 transactions / $20,000 limit.
  • Contractor vs. employee — why the Department of Labor’s interpretation just shifted back to a pre-Biden stance.

Whether you’re a tax pro, CPA, EA, or just curious about the latest changes, this episode is packed with real-world explanations you can put to use immediately.

🎓 Earn CPE credit for listening to this program through our sponsor My CPE One: https://my-cpe.com (make sure to include the hyphen — my-cpe.com).