The (Not Boring) Boring Small Business Bookkeeping and Accounting Podcast
by Paul Rosenblum, The Bookkeeping Mensch | 25+ Years of Bookkeeping, Small Business Finances, and Tax Insights
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Estimated from 1 chart position in 1 market.
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- 🇨🇦CA · Entrepreneurship#1785K to 30K
- Per-Episode Audience
Est. listeners per new episode within ~30 days
2.5K to 15K🎙 ~2x weekly·83 episodes·Last published yesterday - Monthly Reach
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5K to 30K🇨🇦100% - Active Followers
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2K to 12K
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On the show
From 14 epsHost
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Recent episodes
Can a Bookkeeper Go to Jail for Payroll Taxes? S9E7
Jun 11, 2026
3m 12s
Why Are Fast Food Chains Bringing Back Cheap Meals? S9E6
Jun 4, 2026
13m 17s
Signing a Commercial Lease? Top Risks Small Business Owners Need to Know. S9E5
May 28, 2026
2m 42s
Why Shared Business Expenses Create Bookkeeping Problems Fast. S9E4
May 21, 2026
10m 53s
Small Business Meals & Entertainment Write-Off Rules 2026. S9E3
May 14, 2026
2m 50s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/11/26 | Can a Bookkeeper Go to Jail for Payroll Taxes? S9E7 | 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... | 3m 12s | ||||||
| 6/4/26 | Why Are Fast Food Chains Bringing Back Cheap Meals? S9E6 | 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 industr... | 13m 17s | ||||||
| 5/28/26 | Signing a Commercial Lease? Top Risks Small Business Owners Need to Know. S9E5✨ | commercial leasesmall business risks+3 | — | — | — | commercial leasesmall business+5 | — | 2m 42s | |
| 5/21/26 | Why Shared Business Expenses Create Bookkeeping Problems Fast. S9E4✨ | shared expensesbookkeeping problems+3 | — | — | — | bookkeepingshared expenses+5 | — | 10m 53s | |
| 5/14/26 | Small Business Meals & Entertainment Write-Off Rules 2026. S9E3✨ | tax rulessmall business+3 | — | — | — | business mealsentertainment write-offs+3 | — | 2m 50s | |
| 5/7/26 | Business Equipment: Section 179, Depreciation or a DeMinimus Expense. S9E2✨ | business equipmenttax implications+4 | — | desklaptop+2 | — | business equipmenttaxes+5 | — | 10m 28s | |
| 4/23/26 |  Understanding EBITDA: What Lenders and Buyers Look For. S9E1✨ | EBITDAbusiness evaluation+3 | — | — | — | EBITDAprofit+3 | — | 10m 31s | |
| 4/9/26 |  Small Business Growing Too Fast? Accounting and Bookkeeping Problems to Watch S8E3✨ | small business growthaccounting problems+3 | — | — | — | small businessaccounting+5 | — | 15m 45s | |
| 3/26/26 | Should You Be Talking to Your Bookkeeper More? S8E2✨ | bookkeepingcommunication+4 | — | — | — | bookkeepingcommunication+4 | — | 11m 55s | |
| 3/12/26 |  Is AI Driving the Need for Bookkeeping Standardization? S8E1✨ | AI in bookkeepingbookkeeping standardization+3 | — | — | — | AIbookkeeping+3 | — | 13m 12s | |
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| 2/26/26 |  Does Bookkeeping Need To Be More Regulated? S7E4✨ | bookkeepingregulation+5 | — | — | — | bookkeepingregulation+5 | — | 10m 49s | |
| 2/12/26 |  How Bookkeeping Improves Profitability for Small Business Owners: S7E3✨ | bookkeepingprofitability+3 | Jenny | — | — | bookkeepingprofitability+3 | — | 19m 32s | |
| 1/29/26 |  How to Do Bookkeeping for Etsy, eBay, and Online Side Hustles (Fees, Inventory & Taxes): S7E2✨ | bookkeepinge-commerce+3 | — | eBayEtsy | — | bookkeepingEtsy+5 | — | 11m 28s | |
| 1/15/26 |  Are Business Meals Deductible in 2026? A Bookkeeper Explains the New IRS Rules: S7E1✨ | business mealstax deductions+3 | — | IRS | — | business mealsdeductible expenses+3 | — | 17m 53s | |
| 12/18/25 |  Trust Centered Bookkeeping: S6E8✨ | trust in bookkeepingbusiness mindset+3 | Stephanie Fuccio | — | — | trust centered bookkeepingbusiness values+3 | — | 14m 16s | |
| 12/4/25 |  Where Bookkeeping Meets Immortality: S6E7✨ | bookkeepinggrief+3 | — | — | — | bookkeepinggrief+3 | — | 12m 23s | |
| 11/20/25 |  Bookkeeping Ethics and When to Push Back on Client Requests: S6E6 | 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 ... | 24m 05s | ||||||
| 11/6/25 |  When DIY Bookkeeping Meets Pre-Tax Season: S6E5 | 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... | 17m 46s | ||||||
| 10/23/25 |  Haunted by 1099s: PayPal, Venmo & the New Rules: S6E4 | 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 ... | 11m 47s | ||||||
| 10/9/25 |  Getting Cash, Payroll, and Petty Cash Right: S6E3 | 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, P... | 12m 11s | ||||||
| 9/18/25 |  What does ‘cash on hand’ mean in bookkeeping? S6E2 | 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: 💳 How POS systems track sales, ta... | 24m 12s | ||||||
| 9/4/25 |  Bookkeeping Q&A: Get Ahead Before Tax Season Hits: S6E1 | 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 de... | 19m 06s | ||||||
| 8/21/25 |  Two Bookkeeping Mistakes That Cost More Than You Think: S5E10 | 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 last-minute banking and bookkeeping changes can spiral into time-consuming, expensive messes—and how to avoid costly manual work an... | 13m 23s | ||||||
| 8/7/25 |  Two Connected Businesses, One Bookkeeper’s Brain: S5E9 | 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-corporation transition that’s still overlapping. Add in mismatched credit lines, reconciliation headaches, and a full year-end... | 10m 14s | ||||||
| 7/22/25 |  LLC to S Corp? A Bookkeeper’s POV: S5E8 | 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 into how bookkeepers make judgment calls, set priorities, and stay focused—even when the work feels like a “Mission: Impossibl... | 14m 11s | ||||||
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Chart Positions
1 placement across 1 market.
Chart Positions
1 placement across 1 market.