Information Return Intelligence

In this episode of Information Return Intelligence , Jason revisits last week’s big topic: the new overtime deduction created by the One Big Beautiful Bill (OBBB). After initially believing there was no scenario where qualifying FLSA overtime could ever appear on a 1099… Jason discovered there is a rare situation where it actually can. Join Jason as he breaks down: What counts as “qualifying overt...

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 re...

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...

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 profes...