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

In this short episode, our favorite Bookkeeping Mensch, Paul Rosenblum, starts with a follow-up to Season 9, Episode 8, the bookkeeper arrested for nonpayment of payroll taxes during COVID. The defense attorney says the shortfall came from COVID-19 staffing and oversight gaps starting in 2020, with no malicious intent or personal enrichment, and that the tax obligations are being resolved. The criminal case itself still hasn't been settled.

Then Paul shares an unrelated story out of Illinois. Tasha Holbrook, a bookkeeper for a Bensenville business, is accused of stealing more than $1.3 million from August 2018 through August 2022. Charges at Macy's, Nordstrom...

The big summer project is nearly done! Our favorite Bookkeeping Mensch, Paul Rosenblum, reports that the corporation is filed and the accountant is happy, but the related LLC still has to be filed by October 15, and it never had a set of books. Paul takes us through the last leg of the project. There are business and personal accounts full of mixed expenses, shared credit cards, a home office that may need splitting, mystery bank transfers, and shareholder loans that have to match across both companies. He also explains why, if you own more than one company, you should...

The chart of accounts keeps popping up in business news feeds, so our favorite Bookkeeping Mensch, Paul Rosenblum, is taking a fresh look at it. Paul shares why he always designs it for the client, even if some accountants complain about all those subaccounts.

Then Paul gets honest about write-ups, the simplest (and his least favorite) form of bookkeeping. He also answers a question he hears a lot: is there a standard chart of accounts? 

Want more on the chart of accounts? Check out Season 1, Episode 7, and the two-part series in Season 2, Episodes 8 and 9.

Kicking off the next 100 episodes, our favorite Bookkeeping Mensch, Paul Rosenblum, shares a cautionary tale about what happens when third-party software quietly works against you. A client's industry-specific CRM was secretly exporting her invoices into QuickBooks Online as sales receipts. That doubled her sales, threw off undeposited funds, and nearly meant she would pay extra 2026 taxes for no reason. Two three-hour cleanup sessions later, the books are fixed, but it raises a bigger question: just because software CAN connect to QuickBooks, SHOULD it?

Paul walks through the third-party tools he actually likes, including inventory programs like Fishbowl...

One hundred episodes in, our favorite Bookkeeping Mensch, Paul Rosenblum, is taking a moment to thank YOU, the listeners, who turned this independent podcast into something much bigger than a weekly recording. After years of teaching in classrooms, Paul has found a new classroom behind the microphone, a place where he can keep sharing what he knows, connecting with people in the field, and talking about the work he still genuinely loves.

This milestone isn’t a goodbye, it's a celebration. Paul reflects on what reaching 100 episodes means to him, the unexpected recognition the podcast has received al...

Reaching 100 podcast episodes wasn’t something our favorite Bookkeeping Mensch, Paul Rosenblum, ever expected when he started the show in 2022. In this special 99th episode, Paul sits down with Stephanie Fuccio, Podcast Discovery Strategist, to look back at how and why the show changed and what he’s learned from the listeners who keep coming back for more. 

But this isn’t just a look back. A few unexpected moments turn the conversation in directions neither Paul nor listeners will see coming, while revealing more about the people, experiences, and decisions that shaped the show along the way. It...

Tariff refunds may be going back to big companies, but that doesn’t mean a check is coming to us. Our favorite Bookkeeping Mensch, Paul Rosenblum, looks at what those refunds could mean for prices at stores like Walmart, Target, Lowe’s, and Home Depot, and why consumers still need to pay attention to where the savings actually show up. As retailers decide what to do with that money, shoppers have a new reason to compare prices, question where the savings went, and vote with their wallets.

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If rising prices have you blaming inflation for everything, it may be worth looking at the spending habits that have become normal. Our favorite Bookkeeping Mensch, Paul Rosenblum, looks at the difference between expenses we can’t control and the choices that still belong to us. Ultimately, affordability includes how we decide what we need, want, and can actually afford.

With convenience making it easier than ever to spend without thinking much about it, Paul looks at where everyday choices can start stretching a budget too far. From credit cards to routine purchases that no longer feel op...

Some bookkeeping projects don’t just fill the calendar, they make you feel 20 years younger. Our favorite Bookkeeping Mensch, Paul Rosenblum, shares why difficult bookkeeping cleanup projects still give him adrenaline, purpose, and the deep satisfaction of knowing a client’s books are finally right. As he considers slowing down, he’s realizing that the work that lights you up may be exactly the reason not to step away too soon.

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Paul Rosenblum has been doing hands-on bookkeeping for over 3...

If you assume “clean books” means accurate books, it’s worth checking that assumption now, before tax deadlines or an IRS problem force the issue. Three previous bookkeepers had called the books clean, but our favorite Bookkeeping Mensch, Paul Rosenblum, is still finding major problems underneath, including missing credit card transactions, $15,000 in unexplained invoice payments, and a $25,000 shareholder loan that was being counted as taxable revenue. As he works through the mess, he shows how quickly one bad assumption can ripple through the books, especially when QuickBooks misses transactions, personal and business payments get mixed together, or a single deposi...

Choosing between a Roth and Traditional IRA comes down to one question: what tax bracket do you expect to be in when you withdraw. Our favorite Bookkeeping Mensch, Paul Rosenblum, breaks down the tax treatment, contribution limits, and Required Minimum Distribution rules for both, plus a quick look at how inherited IRAs work differently. A short, practical primer for anyone weighing retirement savings alongside their business finances.

Schwab IRA calculator: https://www.schwab.com/ira/ira-calculators

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When the accountant sent these books back as unusable, and three previous bookkeepers had all called them clean, our favorite Bookkeeping Mensch, Paul Rosenblum,  knew this cleanup would take a lot of time. Now he's deep into it and the books are starting to come together.

Picking up where Part 1 left off, Paul walks through the hands-on work of the last several weeks: two of six tangled credit cards now fully reconciled through 2025, months of "buy now, pay later" purchases separated out from cost of goods sold, and adjusting entries created to make beginning-of-year balances finally match r...

Who is responsible for deciding whether a business expense is tax deductible: the client, the bookkeeper, or the tax preparer? In this episode, our favorite Bookkeeping Mensch, Paul Rosenblum, shares his approach to handling missing receipts, client gifts, business meals, and other bookkeeping gray areas. He touches on where professional responsibility begins and ends, and whether bookkeepers should rely on client information or use their own judgment when categorizing expenses. 

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Paul Rosenblum has been doing hands-on bookkeeping for over 30 y...

Three bookkeepers said the books were clean. The accountant said otherwise.

Bad bookkeeping creates business problems, not just accounting problems. Inaccurate financial records can lead to overpaying taxes, missing valuable tax deductions, making decisions based on unreliable numbers, and creating challenges when applying for loans or funding. Our favorite Bookkeeping Mensch, Paul Rosenblum, is here to explain why accurate books matter long before tax season arrives and why getting the numbers right can save businesses significant time, money, and stress.

Using a real bookkeeping cleanup project as a case study, Paul shares how what initially...

Nobody likes thinking about death, but getting your finances in order now can make things much easier for the people you leave behind. To help with this, our favorite Bookkeeping Mensch, Paul Rosenblum, is here to explain the basics. He covers which debts are typically forgiven when someone dies, when an estate is responsible for paying what's owed, why family members usually aren't liable for debts they didn't co-sign, and how naming a beneficiary on a bank account can help avoid probate. It's a practical look at an uncomfortable topic that's worth planning for. 

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Online computerized accounting changes almost everything about bookkeeping. But don’t worry, our favorite Bookkeeping Mensch, Paul Rosenblum, is here to help you navigate the potential problems to come from these “advancements.” For example, QuickBooks Online creates problems that QuickBooks Desktop never had, like duplicate sales, mismatched credit card merchant fees, phantom accounts receivable, and sales tax reports that quietly go wrong. Paul draws on 30 years of hands-on bookkeeping experience to outline the challenges the transition creates for business owners and bookkeepers. And of course, he’s got advice on what to look out for to make sure things run smoo...

Wondering where you fall in the 2026 tax brackets? In this quick episode, Paul Rosenblum walks through the latest tax rates for single and joint filers and explains how they apply to different business structures. It's a simple way to get ahead on tax planning before next year's filing season arrives.

Tax brackets:

https://paulrosenblum.substack.com/p/bookkeeping-rates-for-single-and

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Paul Rosenblum has been doing hands-on bookkeeping for over 30 years, starting with QuickBooks Desktop. 

👀 Why Nich...

Bookkeeping isn’t just spreadsheets and accounting software. Our favorite Bookkeeping Mensch, Paul Rosenblum, reflects on how everyday money habits quietly shape our lives, from business spending decisions to the way people think about vacations, groceries, risk, and long-term planning. He explores “the human side of want and need,” showing how emotional spending, financial stress, personal history, and instinct all influence the way we handle money. This conversation reframes bookkeeping as something deeply human, revealing why some of us naturally think like planners, budgeters, and business owners without even realizing it. 

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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 held legally responsible for payroll taxes, this short episode will give you something to think about.

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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 observations, opinions, and a few personal stories about where the industry may be headed next. Just don’t listen while hungry unless you’re financially and emotionally prepared for a drive-thru run af...

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, responsibility for building problems, or even being forced to relocate after customers have become attached to a location. Careful attention to detail, along with hiring the right legal help during the process, can save small business owners major...

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 accounting, balance sheet loans, and how one missing piece of communication nearly created major tax filing problems. But this episode isn’t really just about bookkeeping entries. It’s about the growing communication gap between business owners and bookkeeping teams, especially in today’s...

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. 

Be sure to let us know if you like this small bites of bookkeeping! 

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Paul Rosenblum has been doing hands-on bookkeeping for over 30 years, starting with QuickBooks De...

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 finances. In this episode, our favorite Bookkeeping Mensch, Paul Rosenblum, breaks down these three key concepts in plain English and explains why business owners should talk with...

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, or simply understanding how healthy your business really is. A company can look profitable on paper but still struggle with cash flow, debt, or owner withdrawals, and EB...

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 ones. He walks through what this actually looks like behind the scenes, and why growth withou...

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 disconnect between bookkeepers, accountants, and clients. He hopes that for you this can be a humorous reminder to stay involved, ask questions, and treat bookkeeping as an ongoing partnership that helps you make better financial decisions.

Se...

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, and banks feed transaction data into accounting systems without standardized formatting. As AI becomes more integrated into tools like QuickBooks, these inconsistencies are becoming harder to ignore.

If the role of the bookkeeper is shifting...

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 of a union, Paul reflects on what might change if clear standards existed. He wonders whether introducing levels, credentials, or even a collective structure would strengthen the profession or complicate it, especially when it...

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 time. By comparing years side by side, organizing income and expenses with intention, and reviewing the numbers regularly, business owners can move from reacting to planning. This e...

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 tax time. He breaks down what really needs to be tracked, what doesn’t, and how to keep your books clean without turning your side hustle into a full-time accounting project, because spreadsheets should...

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 confusion later. Paul breaks down what still counts, what doesn’t, and how bookkeepers can guide clients through the shift without panic or awkward end-of-year conversations. Along the 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.

This episode isn’t really about podcasting. It’s about trust centered bookkeeping and the role relationships, clarity, and care play in long term client work. Using the podcast as a real world exampl...

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, Paul starts sorting through which clients, tax preparers, and workloads actually support his well-being and which ones might need to be gently shown the door. He also digs...

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, the importance of documentation, and why saying “no” is sometimes the most professional thing you can do. Along the way, he shares stories from decades in the field, a few tax tips, and a clear reminder tha...

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 mess is a nightmare, especially when the client is cooperative, communicative, and appreciative. As pre-tax season ramps up, Paul’s feeling—dare we say—pre-seasoned and proud of this bookkeeping cleanup.

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 process, his doubts, and his trademark humor as he untangles what the new $2,500 threshold means for 2025 taxes—and why Zelle might (or might not) escape the chaos.

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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 doc...

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:

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 a...