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When the year ends, reflection begins. In this unusually personal episode, our favorite Bookkeeping Mensch, Paul Rosenblum, takes a pause and looks back at a year filled with loss, change, and a few big reminders that even bookkeepers have limits. He talks openly about grief, shifting energy, evolving client relationships, and what it feels like to age in a profession that runs on precision and stamina. As he looks ahead to 2026, Paul starts sorting through which clients, tax preparers, and workloads actually support his well-being and which ones might need to be gently shown the door. He also digs into the business side of letting go, the emotional weight of being the person everyone relies on, and the very real questions around semi-retirement, succession, and where bookkeeping fits in an AI-shaped future.

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When clients cross the line, how do you hold yours? Bookkeeping isn’t about keeping quiet, it’s about keeping standards. Our favorite Bookkeeping Mensch, Paul Rosenblum, answers a listener’s fan mail about a newer bookkeeper, Katie, whos is struggling with some issues related to this distinction. It’s a full-on masterclass in bookkeeping confidence. Topics covered include the ethical heart of bookkeeping, the importance of documentation, and why saying “no” is sometimes the most professional thing you can do. Along the way, he shares stories from decades in the field, a few tax tips, and a clear reminder that bookkeeping isn’t data entry, it’s responsibility, accuracy, and boundaries.

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📞 Leave a voice message for Paul:

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💸 Website: https://bookkeepermensch.com

🎵 Music: SourceAudio: https://www.sourceaudio.com/

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This pre-tax season, our favorite Bookkeeping Mensch, Paul Rosenblum is having fun because he’s knee-deep in one of his favorite things—a DIY bookkeeping cleanup. He takes us along on the clean up journey, including two tangled LLCs, years of unreconciled accounts, and more. He finds joy in the process by relabeling accounts, sorting out equity, and turning confusion into clarity. It’s a reminder that not every mess is a nightmare, especially when the client is cooperative, communicative, and appreciative. As pre-tax season ramps up, Paul’s feeling—dare we say—pre-seasoned and proud of this bookkeeping cleanup.

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🎧 Producer Steph: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

🎵 Music: SourceAudio: https://www.sourceaudio.com/

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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 means for 2025 taxes—and why Zelle might (or might not) escape the chaos.

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🎧 Producer Steph: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

🎵 Music: SourceAudio: https://www.sourceaudio.com/

🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/

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Cash, Payroll, and Petty Cash Puzzles: Bookkeeping isn’t just “data entry”—it’s detective work that keeps your books accurate and your business safe. Our favorite Bookkeeping Mensch, Paul Rosenblum, gets into the messy reality of handling petty cash, payroll checks, tips, and owner contributions in this episode, using a real client case as a guide. From partner paychecks cashed through the register, to undocumented utilities paid with personal money, to tips that must be reported correctly, Paul explains how these situations can create a jigsaw puzzle if not recorded properly. He shows where cash on hand belongs, how to document unusual transactions, and why open communication between business owners and bookkeepers is essential to avoid costly mistakes. Because in bookkeeping, every dollar tells a story—and it’s never just data entry.

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🎧 Producer Steph: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

🎵 Music: SourceAudio: https://www.sourceaudio.com/

🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/

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When your POS totals don’t match your bank deposits, the mystery usually comes down to three little words. Don't worry, our favorite Bookkeeping Mensch, Paul Rosenblum, is here to break down the tricky world of cash on hand. From POS systems and sales tax to tips, deposits, and those frustrating month-end discrepancies, he explains how this account works, why it’s so confusing, and what both bookkeepers and business owners need to understand, including:

• 💳 How POS systems track sales, tax, and tips
• 🏦 Why deposits rarely match end-of-month sales
• 📊 What “cash on hand” looks like in the books
• 💵 Common mistakes with cash, checks, and payroll
• 🤝 How communication between owners and bookkeepers prevents messy books

With real-world examples and clear explanations, Paul gives you the clarity and confidence to spot cash-on-hand issues before they snowball into messy books and costly fixes.

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📞 Leave a voice message for Paul:

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🎧 Producer Steph: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

🎵 Music: SourceAudio: https://www.sourceaudio.com/

🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/

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QuickBooks, 1099s, Affirm, Cars, Chaos.

👉 Bookkeepers and Business owners can’t afford to wait until tax season to get organized.

In this first-ever Q&A episode, Paul Rosenblum — Our Favorite Bookkeeping Mensch — tackles real listener questions about:

✅ When to start fresh in QuickBooks

✅ How to reconcile every account (banks, loans, investments)

✅ What the new 1099 thresholds mean

✅ The right way to handle Affirm loans and vehicle financing

Paul also shares a candid story about client delays and missing access that turned into a last-minute scramble, raising the bigger question: why do bookkeepers stop everything at the wrong time?

💬 Send your questions anytime at BookkeeperMensch.com

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Support the show

📞 Leave a voice message for Paul:

https://www.speakpipe.com/PaulRosenblumPodcast

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https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms

🎧 Producer Steph: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

🎵 Music: SourceAudio: https://www.sourceaudio.com/

🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/

📨 Email: Bookkeepermensch@gmail.com

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When your bookkeeper says, “Call me before you make big changes,” this is why.

Two unexpected summer projects pushed Our Favorite Bookkeeping Mensch, Paul Rosenblum, to the edge of his patience gene—one with endless QuickBooks disconnects and surprise Amex accounts, the other a full switch to Square with quirky deposits and a surprise loan.

Listen in to learn how last-minute banking and bookkeeping changes can spiral into time-consuming, expensive messes—and how to avoid costly manual work and delays through better planning and access sharing. These simple communication habits will keep your books (and your bookkeeper) in great shape.

Support the show

📞 Leave a voice message for Paul:

https://www.speakpipe.com/PaulRosenblumPodcast

😄 Send him a text message (remember to include your contact info)

https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms

🎧 Producer Steph: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

🎵 Music: SourceAudio: https://www.sourceaudio.com/

🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/

📨 Email: Bookkeepermensch@gmail.com