W-9, 1099-K, and the Tax Benefit Rule: What Every Accountant Should Know (Fall 2025 Update)

W-9, 1099-K, and the Tax Benefit Rule: What Every Accountant Should Know (Fall 2025 Update)

In this episode, Jason Dinesen breaks down three big updates affecting accountants, tax preparers, and small business owners in Fall 2025: 🔹 1. Draft W-9 Changes The IRS has released a draft of Form W-9 that could significantly change how sole proprietors and single-member LLCs report their Taxpayer Identification Numbers. Jason explains: What’s in the draft (and what’s not official yet) Why sole proprietors might soon be required to use their Social Security Number How to keep tabs on the official IRS W-9 page for updates 🔹 2. 1099-K Thresholds and the “Big Beautiful Bill” The so-called “Big Beautiful Bill” rolled back the $600 threshold for third-party payment reporting. Jason discusses: Why the $20,000 / 200-transaction rule is back How this impacts gig workers, small sellers, and payment apps like Venmo and PayPal Whether the IRS really gained anything from the lower threshold 🔹 3. The Tax Benefit Rule Returns With the new $40,000 SALT cap and permanent standard deduction increases, more taxpayers may again face taxable state refunds. Jason explains what the tax benefit rule is, how it works, and why it’s suddenly relevant again. 🎧 Listen and Learn 🎓 Earn CPE Credit: You can earn continuing education credit for watching or listening through My-CPE.com (remember the hyphen!).

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

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).

Summertime Tax Moves, Expiring Credits, and That Big Beautiful Bill

It’s summertime... but there’s still tax planning to do. In this solo episode of Accounting in the Wild, Jason Dinesen breaks down what tax professionals (and taxpayers!) need to know right now — before key deadlines and credits disappear. In this episode: * ⚡ Energy credits are going away — EV, solar, appliances, and more * ✉️ IRS will no longer accept paper checks after September 30 * 🏕️ Day camps and the daycare credit: what counts? * 💸 Overtime and tip deductions — where do they go on the return? * 🚗 Also the new deduction for certain car loan interest deduction -- where does it go? * 🧾 Written Information Security Plans (WISPs) — are you in compliance? * 🧓 Did Congress eliminate tax on Social Security? Nope — here's what they actually did Timestamps: 00:00 – Welcome 00:27 – Expiring energy credits (EV, solar, windows) 04:34 – Section 179D update for commercial projects 06:48 – IRS ends paper checks (big change alert!) 10:35 – Day camps and the child care credit 12:49 – Daycare credit changes under BBB (starting 2026) 14:32 – Dependent care FSAs increase to $7,500 16:49 – Tip/overtime deduction ≠ AGI deduction 18:53 – Car loan interest deduction: the rules 20:48 – Written data security plans (WISP) 22:37 – Social Security taxation myths 24:47 – Final thoughts CPE Credit Available: Want continuing ed credit for this episode? Listen on MyCPE.com — search “Accounting in the Wild” to get started. Hosted by: Jason Dinesen, EA Founder of Dinesen Media Ventures | Tax Pro | Educator | Storyteller Brought to you by: MyCPE.com — offering 15,000+ hours of online CPE & CE for CPAs, EAs, and tax pros. 🎧 Subscribe on your favorite platform and stay up to date on tax topics, stories from the trenches, and interviews from the frontlines of accounting.

Data Security for Accountants, with Nick Mullen of Entoo Security

In this episode of Accounting in the Wild, Jason welcomes Nick Mullen, Chief Advisor at Entoo Security, for a critical conversation about cybersecurity for tax pros and accounting firms. ***DISCOUNT*** Mention Accounting in the Wild when you sign up for services with Entoo Security and they'll give you a 50% discount on your onboarding fees! Topics: * Why “just don’t click the link” isn’t real protection * How hackers use DocuSign, QuickBooks, and even deepfakes to target small firms * Why antivirus is no longer enough * MFA: what works, what doesn’t, and how criminals get around it * How to securely offshore work (hint: it’s not just handing over your passwords) * What the FTC Safeguards Rule and the IRS’s WISP template mean for your firm * Where and how to get started on protecting your data 🎁 Special offer: Mention Accounting in the Wild and get 50% off onboarding at Entoo Security 🌐 https://www.entoosecurity.com [https://www.entoosecurity.com] 📩 info@entoosecurity.com 🎙️ Hosted by Jason Dinesen — accountant, educator, former radio guy, and passionate explainer of the real world behind the spreadsheets.

Unlocking Tax Savings: Cost Segregation and Section 179D

In this episode of Accounting in the Wild, Jason is joined once again by Randy Eickhoff of Acena Consulting for a real-world discussion on two powerful tax strategies for real estate investors and building designers: cost segregation and the Section 179D deduction. They explore: * What Section 179D is and who qualifies * How cost segregation works and when it makes sense * IRS audit considerations and Form 3115 catch-up strategies * The surprising connection between 179D, cost seg, and the R&D credit * Why these strategies are about more than just tax savings—they’re cash flow tools Whether you're a tax pro, real estate investor, or just tax-curious, this episode will give you practical insights into using the tax code to your advantage. 🔗 Learn more about Randy’s firm at acenaconsulting.com [https://acenaconsulting.com]