Haunted by 1099s: PayPal, Venmo & the New Rules: S6E4 episode artwork

EPISODE · Oct 23, 2025 · 11 MIN

Haunted by 1099s: PayPal, Venmo & the New Rules: S6E4

from The (Not Boring) Boring Small Business Bookkeeping and Accounting Podcast | Taxes, Cash Flow, and Financial Systems · host Paul Rosenblum, Expert Bookkeeper

What’s scarier than Halloween? For bookkeepers, it’s the ever-changing 1099 rules. This October, our resident Bookkeeping Mensch, Paul Rosenblum, suits up in his “bookkeeper costume” and dives into the latest PayPal and Venmo 1099 updates. Between the ghosts of shifting IRS thresholds and the rise of AI-generated everything, Paul reminds us why the human side of bookkeeping still matters. He shares his process, his doubts, and his trademark humor as he untangles what the new $2,500 threshold means for 2025 taxes—and why Zelle might (or might not) escape the chaos.Send us Fan MailSupport the showAbout the hostPaul Rosenblum has been doing hands-on bookkeeping for over 30 years, starting with QuickBooks Desktop and adapting to the world of cloud-based QuickBooks Online. He shares practical, in-the-weeds lessons from real client files every episode.👀 Why Niche Podcasts Are The Bedrock Of The Industry: https://podalization.substack.com/p/why-niche-podcasts-are-the-bedrock😄 Send Paul a text or 📞 voice message (include your contact info if you want a reply) https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms📨   Email:   [email protected]💸  Website: https://bookkeepermensch.com🎧 Producer Steph: https://linktr.ee/stephfuccio 🎵 Music: SourceAudio: https://www.sourceaudio.com/🔉 Sound effects: https://freesound.org

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What’s scarier than Halloween? For bookkeepers, it’s the ever-changing 1099 rules. This October, our resident Bookkeeping Mensch, Paul Rosenblum, suits up in his “bookkeeper costume” and dives into the latest PayPal and Venmo 1099 updates. Between the ghosts of shifting IRS thresholds and the rise of AI-generated everything, Paul reminds us why the human side of bookkeeping still matters. He shares his process, his doubts, and his trademark humor as he untangles what the new $2,500 threshold ...

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Haunted by 1099s: PayPal, Venmo & the New Rules: S6E4

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This episode was published on October 23, 2025.

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