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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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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!).
14 episodes
