The (Not Boring) Boring Small Business Bookkeeping and Accounting Podcast
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 QuickBooks, this podcast is for bookkeepers and small business owners who know business is about more than just numbers.
🎧 Listen to episodes like:
-Bookkeepers Are More Than Bean Counters
-How Communication Impacts Your Bookkeeping
-Plus hands-on tools like QuickBooks basics, startup expenses, and chart of accounts.
Episodes
71 episodes
Haunted by 1099s: PayPal, Venmo & the New Rules
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. Betw...
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Season 6
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Episode 4
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11:47
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Getting Cash, Payroll, and Petty Cash Right
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...
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Season 6
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Episode 3
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12:11
What does ‘cash on hand’ mean in bookkeeping?
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 P...
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Season 6
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Episode 2
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25:13
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Bookkeeping Q&A: Get Ahead Before Tax Season Hits
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...
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Season 6
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Episode 1
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19:06
Two Bookkeeping Mistakes That Cost More Than You Think
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 di...
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Season 5
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Episode 10
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13:23
Two Connected Businesses, One Bookkeeper’s Brain
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 interconne...
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Season 5
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Episode 9
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10:14
LLC to S Corp? A Bookkeeper’s POV
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 ...
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Season 5
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Episode 8
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14:11
QuickBooks Chaos to Clarity Case Study
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 car...
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Season 5
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Episode 7
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13:43
Bookkeeping Off-Season Planning That Pays Off
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 clien...
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Season 5
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Episode 6
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13:17
Prepare Your Bookkeeping Deductions Early
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 ow...
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Season 5
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Episode 5
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11:04
Why Accrual Accounting Costs More
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 ...
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Season 5
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Episode 4
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18:13
Bookkeeping Without the Burnout
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...
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Season 5
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Episode 3
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17:10
2024 Bookkeeping Checklist: What to Do After Tax Season
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 ac...
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Season 5
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Episode 2
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8:49
No Income Tax: Boom or Bust?
What if your paycheck came with zero income tax deductions? In this episode, Paul explores a proposal to eliminate federal income tax for those earning under $150K—and what that could mean for small businesses, economic classes, and yo...
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Season 5
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Episode 1
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15:09
Classifying Workers: Rules, Risks, and Red Flags
How can businesses determine whether a worker should be classified as a W-2 employee or a 1099 subcontractor? Our resident bookkeeping mensch, Paul Rosenblum, breaks down the two main tests—the Common Law Test and the ABC Test—used by states an...
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Season 4
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Episode 10
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13:12
How to Handle Large Budget Deposits
How should businesses handle large budget deposits in their bookkeeping and tax reporting? Our resident Bookkeeping Mensch, Paul Rosenblum, walks us through three different accounting approaches, focusing on whether to report these deposits as ...
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Season 4
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Episode 9
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12:18
Bookkeping Ethics & Tax Prep: Does your Tax preparer owe you a Fiduciary Duty?
What happens when ethical dilemmas and financial reality collide in tax preparation and bookkeeping? That’s what our resident Bookkeeping Mensch, Paul Rosenblum, is going to unpack in this episode. Specifically, where the fine line between fidu...
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Season 4
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Episode 8
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17:41
Bookkeeping Ethics and Fair Pricing
Are bookkeepers charging fair prices, or are some taking advantage of clients? Our resident Bookkeeping Mensch, Paul Rosenblum, dives into the ethics of pricing, exposing common practices like overcharging for 1099 filings. Through real busines...
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Season 4
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Episode 7
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16:24
Bookkeeping Trend: Less But More And More
The flavor of business always changes over time but what our resident Bookkeeping Mensch, Paul Rosenblum, has noticed recently in his own bookkeeping practice is going to surprise you. Less but more is the best way I can explain it but Paul doe...
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Season 4
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Episode 6
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12:22
Your Complete 2025 U.S. Tax Checklist
It’s a new year and you’re ready to get on top of your small business taxes. Our resident Bookkeeping Mensch, Paul Rosenblum, is here with a handy checklist of super important items that you need to know about (and follow up on) to make sure yo...
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Season 4
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Episode 5
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12:44
Twelve Days of Christmas Bookkeeping
We can’t wrap up the year without a playful holiday episode, can we? That’s why our resident Bookkeeping Mensch, Paul Rosenblum, is here to share his bookkeeping take on The Twelve Days of Christmas. He outlines key bookkeeping tasks h...
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Season 4
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Episode 4
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10:08
Signs of bad bookkeeping
After you find a suitable bookkeeper for your business, it can be easy to assume that your job is done. Now it’s their turn to do the books and you can do anything else in the business, right? But our beloved Bookkeeping Mensch, Paul Rosenblum,...
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Season 4
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Episode 3
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17:40
How Communication Impacts Year-End Bookkeeping?
What do $12,000, lending company money and 3 LLC's have to do with one another? These are the examples that our resident Bookkeeping Mensch shares with us to demonstrate that communicating with your Bookkeeper all year is essential.
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Season 4
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Episode 2
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12:47
What Leadership Changes Could Mean for Small Business
As Americans process recent political events, our level-headed resident Bookkeeping Mensch, Paul Rosenblum, offers thoughtful reflections on how upcoming leadership changes may impact small businesses. He provides a big-picture view on possible...
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Season 4
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Episode 1
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13:22
Balancing Business Divorces Brilliantly
Why did the bookkeeper break up with the partnership? Too many outstanding issues and not enough balance! But don't worry, our very balanced Bookkeeper Mensch, Paul Rosenblum, is here to share how to avoid such issues. He talks about five LLCs ...
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Season 3
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Episode 18
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14:35