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

Payroll taxes are not just paperwork, and Paul Rosenblum shares a quick but important reminder about how bookkeepers can face serious legal consequences when payroll taxes are not filed or paid correctly. Using a real Rhode Island case, our favorite Bookkeeping Mensch reflects on bookkeeper liability, professional responsibility, and why ethics matter so much in bookkeeping. If you’ve ever wondered whether a bookkeeper can be...

Fast Food Chains Are Reinventing Themselves Again. If eating out has felt more expensive, less personal, or just different lately, there’s a reason, and our favorite Bookkeeping Mensch, Paul Rosenblum, is here to explain why. What starts as a conversation about fast food quickly becomes a bigger look at how restaurants are struggling to adapt to changing customer habits and economic pressure. Along the way, Paul shares observ...

Signing a commercial lease can feel like just another business task, but one missed detail can create expensive problems for years. Our favorite Bookkeeping Mensch, Paul Rosenblum, explains why commercial leases are major long-term financial decisions that can directly affect the survival and stability of a business. He walks through the real-world consequences of missing important details, including massive rent increases, respons...

Shared expenses. Missing communication. Bookkeeping chaos. What happens when one business owner starts moving between multiple companies, reimbursable expenses, partnerships, and credit cards… but forgets to tell their bookkeeper what’s actually happening?

In this episode, our favorite Bookkeeping Mensch, Paul Rosenblum, walks through a real bookkeeping situation involving reimbursements between businesses, partnership ...

Business meal and entertainment tax rules have changed, and many small business owners still aren't sure what's deductible in 2026. Don't worry, our favorite Bookkeeping Mensch, Paul Rosenblum, is here to explain meals, sports tickets, country clubs, and how to handle reimbursable expenses the smart way in a new experimental episode. 

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That desk, laptop, or company vehicle might affect your taxes more than you think.Get clear on how these items should be handled in your bookkeeping.

Many business owners buy equipment without knowing whether it should be depreciated over time, written off with Section 179, or treated as a smaller expense under de minimis rules. Those choices can impact taxes, bookkeeping accuracy, and how clearly you understand your business financ...

Your profit might be lying to you. Not all profit tells the truth. In this episode, Paul breaks down EBITDA, a key number that banks, buyers, and investors use to evaluate your business. While your standard profit and loss includes expenses like interest, taxes, depreciation, and amortization, EBITDA strips those out to show what your business actually earns at its core. That matters if you’re thinking about selling, merging,...

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 fal...

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 communication leads to errors, delays, and disc...

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 bookkeeping services varies wildly, certifications are inconsistent...

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, professional identity, and even the idea...

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 loses money, and which decisions affect profitability over ...

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, fees, and inventory start to blur together at...

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 little clarity now can save a lot of confu...

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.

This episode isn’t really about podcasting. It&rsq...

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, P...

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, th...

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 me...

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 proce...