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PODCAST

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

Paul Rosenblum, The Bookkeeping Mensch | 25+ Years of Bookkeeping, Small Business Finances, and Tax Insights

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

16:07

Small Business Growing Too Fast? Accounting and...

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

2026/04/09

Send us Fan Mail Your business is growing, but your systems aren’t keeping up. Our favorite Bookkeeping Mensch, Paul Rosenblum, is seeing this everywhere, and let’s just say he’s not popping champagne about it. He’s watching clients add more LLCs, more accounts, more moving parts, but not more structure, and somehow he’s the one who gets to sort it all out later. That’s where the problems sneak in. Books fall behind, decisions get harder, and small issues quietly turn into expensive one...

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12:17

Should You Be Talking to Your Bookkeeper More?

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

2026/03/26

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! How about a candid and lighthearted vent about the hidden frustration bookkeepers face when small business owners don’t communicate or engage with their bookkeeping, financial reports, and business finances? It’s time for our favorite Bookkeeping Mensch, Paul Rosenblum, to share real situations, from miscategorized transactions to years of ignored reports, to show how poor c...

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13:34

Is AI Driving the Need for Bookkeeping Standardization?

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

2026/03/12

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! While AI may improve data entry, it still lacks the judgment required for tax code decisions, loan splits, fixed assets, and meaningful financial analysis. In this Season 8 opener, our resident Bookkeeping Mensch, Paul Rosenblum, explores how artificial intelligence is beginning to influence the bookkeeping profession. But the bigger issue is structural. Pricing for bookkeep...

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10:49

Should Bookkeeping Be More Regulated?

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

2026/02/26

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 has no real guardrails. What happens when a profession has no required standards? That’s the heart of the “listener” question our favorite Bookkeeping Mensch, Paul Rosenblum, explores in this episode. As he thinks it through, he zooms out and looks at the structure of the entire bookkeeping profession, from certification and continuing education to pricing,...

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19:32

How Bookkeeping Improves Profitability for Small...

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

2026/02/12

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! Your numbers should work harder. Our favorite Bookkeeping Mensch, Paul Rosenblum, has a simple message: your books should help you think. In this episode, Paul answers a listener question from Jenny and walks through what good bookkeeping is actually meant to do. Create clarity. When bookkeeping is done well, it shows how a business really makes money, where it quietly...

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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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84 results

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