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PODCAST

The (Not Boring) Boring Small Business Bookkeeping and Accounting Podcast

Paul Rosenblum, Bookkeeping Mensch

If you’ve ever felt stuck in the digits, this show brings your business personality to the forefront. We go beyond spreadsheets to talk about the relationships that make businesses thrive—between bookkeepers, clients, accountants, and financial professionals.Welcome to The Not Boring, Boring Bookkeeping and Small Business Podcast—where we explore the human side of bookkeeping and business.Hosted by Paul Rosenblum, a New York-based bookkeeper with over 30 years of experience and decades teaching

business entrepreneurship

All Episodes

11:06

How to Do Bookkeeping for Etsy, eBay, and Online Side...

The (Not Boring) Boring Small Business Bookkeeping... ·

2026/01/29

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! If you sell on eBay or another online marketplace and quietly wonder whether you’re recording sales, fees, or inventory the right way, you’re not alone, and you may be overcomplicating it. In this episode, our resident Bookkeeping Mensch, Paul Rosenblum, answers a listener question about how online sellers should actually handle bookkeeping, especially when platform reports,...

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17:31

Are Business Meals Deductible in 2026? A Bookkeeper...

The (Not Boring) Boring Small Business Bookkeeping... ·

2026/01/15

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! Let’s Talk Lunch… And Reality. This tax season comes with a few surprises. Season 7 kicks off with a friendly but practical walkthrough of one of the most misunderstood areas of bookkeeping: everyday food and drink expenses. Our favorite bookkeeping mensch, Paul Rosenblum, explains what’s changed for 2026, why certain habits no longer work the way they used to, and how a lit...

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14:49

Trust Centered Bookkeeping

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/12/18

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! Trust is the foundation of good bookkeeping, but it’s rarely talked about as a business mindset. In this year end episode, our favorite Bookkeeping Mensch, Paul Rosenblum, is joined by me, producer Stephanie Fuccio, for a reflective conversation about how values shape the way we work. What begins as a look behind the scenes of the podcast quickly becomes something deeper. Th...

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12:50

Where Bookkeeping Meets Immortality

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/12/04

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 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 r...

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25:00

Bookkeeping Ethics and When to Push Back on Client...

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/11/20

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 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 th...

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17:46

When DIY Bookkeeping Meets Pre-Tax Season

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/11/06

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! 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 cl...

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11:47

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

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/10/23

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! 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 ...

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12:11

Getting Cash, Payroll, and Petty Cash Right

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/10/09

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! 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 cas...

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25:13

What does ‘cash on hand’ mean in bookkeeping?

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/09/18

🦉 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 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...

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20:22

Bookkeeping Q&A: Get Ahead Before Tax Season Hits

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/09/04

🦉 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! 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

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13:23

Two Bookkeeping Mistakes That Cost More Than You Think

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/08/21

🦉 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

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10:55

Two Connected Businesses, One Bookkeeper’s Brain

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/08/07

🦉 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 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-corp...

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14:11

LLC to S Corp? A Bookkeeper’s POV

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/07/22

🦉 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! 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

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13:43

QuickBooks Chaos to Clarity Case Study

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/07/08

🦉 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! 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 tha...

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13:17

Bookkeeping Off-Season Planning That Pays Off

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/06/17

🦉 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! 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

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1:23

Get Early Access to New Episodes

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/06/16

🦉 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 🎧 Get early access to the podcast by subscribing: https://www.buzzsprout.com/2188873/supporters/new 😄 Send Paul a message. (add your email for a reply). https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms 🎧 Production & Marketing Assistance: https://www.coffeelikemedia.com/ 💸 Website: https://bookkeeper...

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11:04

Prepare Your Bookkeeping Deductions Early

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/06/06

🦉 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! 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

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18:13

Why Accrual Accounting Costs More

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/05/22

🦉 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! Think bookkeeping is just data entry? In this episode, Paul breaks down the world of accrual accounting to show why it's more than just tracking numbers—it's a complex, monthly process that requires detailed attention and explains why it costs business owners more. If cash-based accounting is a jog, accrual accounting is a marathon... and your bookkeeper deserves more

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17:10

Bookkeeping Without the Burnout

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/05/08

🦉 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! Feeling burned out after tax season and rethinking how (and who) you work with? Paul Rosenblum is right there with you—trading high-stress clients and tangled accounts for quality work with people who actually pay (and say thank you). He shares real-world stories, hard-earned boundaries, and bookkeeping wisdom that helps you work smarter, not just harder—because sometimes

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8:49

2024 Bookkeeping Checklist: What to Do After Tax Season

The (Not Boring) Boring Small Business Bookkeeping... ·

2025/04/24

🦉 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! Still haven’t touched your 2024 books because tax season left you emotionally (and spreadsheet-ly) drained? You’re not alone—but our resident Bookkeeping Mensch, Paul Rosenblum, is here to help you shake off the post-April 15th fog and actually get your bookkeeping act together, starting with a simple checklist and some friendly guidance. Whether you're sorting recei...

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79 results

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