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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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🎧 Podcast production & Growth: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

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

📨 Email: [email protected]

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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.

IRS $6K deduction

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🎧 Podcast production & Growth: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

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

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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

Sound effect: 

old cash register open and close with a bing by clubmydia+ -- https://freesound.org/s/584168/ -- License: Creative Commons 0

Support the show

😄 Send Paul a message. (add your email for a reply). https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms

🎧 Podcast production & Growth: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

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

📨 Email: [email protected]

Send us a text message! But please include your email or a way to get in touch with you. This feature is not two way!

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

😄 Send Paul a message. (add your email for a reply). https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms

🎧 Podcast production & Growth: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

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

📨 Email: [email protected]

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When two businesses blur the lines.Our resident Bookkeeping Mensch, Paul Rosenblum,  isn’t just cleaning up books—he’s navigating tangled ones in real time. This episode spends time on a rare challenge: managing finances for two interconnected businesses, where rent flows between an auto shop and the real estate company that owns it, while also handling an LLC-to-corporation transition that’s still overlapping. Add in mismatched credit lines, reconciliation headaches, and a full year-end merge ahead, and it’s clear this isn’t your average summer catch-up. Paul also begins testing alternatives to QuickBooks and shares a clever IT workaround that extends the life of an old office computer. For a behind-the-scenes look at layered bookkeeping decisions and the calm, strategic thinking they require, listen to the full episode.

Support the show

😄 Send Paul a message. (add your email for a reply). https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms

🎧 Podcast production & Growth: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

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

📨 Email: [email protected]

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Bookkeeping summer projects aren’t for the fainthearted. Our resident Bookkeeping Mensch, Paul Rosenblum, is here to share the behind-the-scenes reality of juggling routine monthly tasks with complex, thinking-heavy projects like transitioning a client from an LLC to an S Corp, navigating unclear tax advice, and digging into forgotten 2021 transactions. It’s a glimpse into how bookkeepers make judgment calls, set priorities, and stay focused—even when the work feels like a “Mission: Impossible” episode. Listen in to learn what really happens when clean books meet messy business changes.

Support the show

😄 Send Paul a message. (add your email for a reply). https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms

🎧 Podcast production & Growth: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

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

📨 Email: [email protected]

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Messy Books, Real Fixes, No Fluff. This episode isn’t theory—it’s what bookkeepers really deal with. In this episode, our resident Bookkeeping Mensch, Paul  Rosenblum, shares the chaos of a real client’s finances: seven credit cards, tangled business and personal transactions, and even a surprise closed bank account with missing rent payments. Unlike past episodes that offer broad tips, this one gets into the gritty details of how he actually solves these problems using both traditional and unconventional QuickBooks methods. He highlights the importance of client communication, the reality of adjusting workflows on the fly, and why he’s now focusing on respectful, high-quality clients

Support the show

😄 Send Paul a message. (add your email for a reply). https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms

🎧 Podcast production & Growth: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

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

📨 Email: [email protected]

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Summer’s quiet—Paul’s workload isn’t. While others slow down, our resident Bookkeeping Mensch, Paul Rosenblum speeds up. Come along as he shares how the summer months become his most productive time. It's perfect for him to tackle complex client projects, catch up on multi-year financials, and prepare for the busy season ahead. You’ll see how strategic bookkeeping during quieter months builds a foundation for smoother, more accurate reporting when business picks up. The episode delivers a clear message: by investing effort when things are quiet, you buy yourself control, confidence, and breathing room when it’s sheer chaos. Whether you’re a bookkeeper managing big projects or a business owner trying to stay ahead, this episode is a masterclass in planning with purpose.

Support the show

😄 Send Paul a message. (add your email for a reply). https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms

🎧 Podcast production & Growth: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

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

📨 Email: [email protected]

🦉 Send us a text message! But please include your email or a way to get in touch with you. This feature is not two way!

Thank you for your support. 

Support the show

😄 Send Paul a message. (add your email for a reply). https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms

🎧 Podcast production & Growth: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

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

📨 Email: [email protected]

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Tax prep starts now — not later. Getting your deductions organized early can save stress, time, and money when tax season rolls around. Our resident Bookkeeping Mensch, Paul Rosenblum, knows that whether you're a W-2 employee or running your own business, knowing what to track now will keep your books in top shape — and your future self will thank you. In this episode Paul covers personal medical expenses to powerful business deductions like Section 179 and bonus depreciation. In essence, what matters most for 2025 tax prep. 

Speaking of deductions, why did the bookkeeper bring a ladder to work? Because they heard the deductions were through the roof! 

Links: 

Tax rate chart: 

https://www.linkedin.com/posts/paul-rosenblum-b284a3_smallbusiness-taxes-accounting-activity-7336864838956015619-J2-U

Episode 1: 

https://www.buzzsprout.com/2188873/episodes/12836059-start-up-expenses

Support the show

😄 Send Paul a message. (add your email for a reply). https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms

🎧 Podcast production & Growth: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

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

📨 Email: [email protected]