The IRS has issued new guidance on reporting tips and overtime, and while these topics usually live in the W-2 world, they now have implications for 1099 filers as well.

In this episode, Jason Dinesen — The 1099 Guy — explains how the Big Beautiful Bill created a new personal tax deduction for qualifying tips and qualifying overtime, and how upcoming changes to Form 1099-NEC and 1099-MISC will reflect this. Jason also breaks down the difference between voluntary and non-voluntary tips, why most overtime won’t qualify for contractors, and what AP and payroll teams need to track — even though processing the payments themselves won’t change.

You’ll learn:

• The new tip & overtime deduction created by recent legislation
• What counts as a qualifying tip (and what doesn’t)
• Why qualifying overtime rarely applies to contractors
• How upcoming 2026 1099 forms will include new boxes
• What issuers must track for future reporting

Information Return Intelligence delivers weekly insights to help accounting and finance pros stay compliant with 1099, 1042-S, W-9, and related reporting rules.

🎙️ Hosted by Jason Dinesen, EA — The 1099 Guy

The IRS quietly released a draft Form W-9 in mid-September — and one proposed change could have a major impact on how businesses collect taxpayer identification numbers from sole proprietors and single-member LLCs.

In this episode, Jason Dinesen — The 1099 Guy — breaks down what’s in the draft, why the change matters, and what AP, procurement, and vendor onboarding teams should do now (and not do yet).
This is a big one: the IRS is proposing that sole proprietors would no longer be allowed to provide an EIN — only a Social Security Number. Jason explains why this shift is happening, how LLC confusion plays into it, and what you’ll need to update if the draft becomes final.

In this episode:
00:00 — Welcome to Information Return Intelligence
00:30 — Draft W-9 released in mid-September
01:40 — New digital asset broker checkbox
02:05 — The major proposed change: SSNs only for sole proprietors
03:00 — Why LLC confusion is driving this
04:20 — Current rules vs. proposed rules
06:25 — Why draft status matters (don’t change anything yet!)
07:40 — How to monitor the IRS W-9 page
09:10 — Will you need to re-solicit W-9s? Jason explains
11:00 — What to do now (and what not to do)

🎙️ Hosted by Jason Dinesen — The 1099 Guy

#1099 #W9 #TaxCompliance #VendorManagement #Accounting #InformationReturns

Information Return Intelligence delivers weekly, practical insights on 1099s, 1042-S, W-9s, and the full ecosystem of information reporting — helping professionals stay compliant and a step ahead.

🎙️ Hosted by Jason Dinesen, EA — The 1099 Guy

The $600 reporting threshold for 1099s has been with us since 1954 — older than Elvis and untouched by inflation. But starting with 2026 payments, it’s finally changing to $2,000 and will be indexed going forward.

In this episode, host Jason Dinesen — The 1099 Guy — explains why the threshold lasted so long, what’s changing under the Big Beautiful Bill, and what steps accounting and finance professionals should take to prepare.

You’ll learn:

• The history and legal background of the $600 rule
• How and when the new $2,000 threshold applies
• What forms and transactions are affected
• How to prepare your systems for annual updates

Information Return Intelligence delivers practical insights for accounting and compliance professionals who work with 1099s, 1042-S, and other information returns — helping you stay compliant, confident, and a step ahead.