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

Send us Fan MailShared 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 remote work environment.If you've ever thought bookkeeping was “just data entry,” or assumed your accountant or bookkeeper would somehow magically figure everything out later, this episode explains why that mindset can become expensive fast.Support the show

Send us Fan MailBusiness meal and entertainment tax rules have changed, and many small business owners still aren't sure what's deductible in 2025. 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! Support the show

Send us Fan MailThat 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 their tax preparer now that things are a bit calmer post tax season. This episode could save you money and reduce confusion.Links: NOLO: IRS De Minimis Rule for Deducting Business Property: https://www.nolo.com/legal-encyclopedia/new-irs-de-minimis-rule-deducting-business-property.html#:~:text=BasicallyQuickbooks Small business tax deductions cheat sheet: chrome-extension://efaidnbmnnnibpcajpcglclefindmkaj/https://digitalasset.intuit.com/render/content/dam/intuit/sbseg/en_us/Blog/Downloadable-assset/Checklist/small-business-tax-deductions-checklist-us-en.pdfIndeed, What Is the Definition of De Minimis in Business? https://www.indeed.com/hire/c/info/de-minimisSupport the show

Send us Fan MailYour 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 EBITDA helps highlight earning potential, not the full picture. Paul also shares real client examples to show how these adjustments play out and what buyers may look for beyond this number. Listen to the full episode to understand how EBITDA works and when you should actually use it.EBITDA download: https://drive.google.com/drive/folders/1C_4Owq5WyWFsjIndVUAG_iXlQdY7AelN?usp=drive_linkSupport the show

Send us Fan MailYour 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 without systems puts pressure on everything underneath, especially the humans trying to keep it all running. But he also shares what it looks like when a client gets it right, and why that makes his bookkeeping heart very, very happy.Support the show

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 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.Support the show

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 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 from data entry to review, explanation, and advisory work, then standards, accreditation, and clearer industry expectations may need to evolve alongside it. Do you agree or disagree? Let Paul know. Contact details are below. The last episode on bookkeeping industry regulations:https://pod.link/1688000860/episode/QnV6enNwcm91dC0xODcxMTY0NgSupport the show

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, 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 comes to pricing and client expectations.This episode doesn't push a final answer. It opens the door to a bigger conversation about where bookkeeping is headed.Links mentioned:American Institute of Professional Bookkeepers, https://aipb.orgNational Association of Certified Public Bookkeepers, https://nacpb.orgInstitute of Certified Bookkeepers, https://www.bookkeepers.org.uk/The Bookkeeping Cooperative, https://bookkeeping.coop/home/Support the show

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 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 episode is about using bookkeeping as a practical tool, not an abstract report.Support the show

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, 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 help you sleep better, not keep you up at night.Support the show

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 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, he reminds us (again) that good bookkeeping isn't about perfection or software shortcuts. It's about judgment, context, steady communication throughout the year, and the human element that no software can replace.Ask Paul a question: https://www.speakpipe.com/PaulRosenblumPodcastSupport the show

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.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 example, Paul shares how trust guides his decisions, from how he communicates to how he shows up for clients.When trust comes first, processes follow. And that mindset changes everything.Happy Holidays everyone!Be a part of the podcast by asking a question. Leave your voice message here: https://www.speakpipe.com/PaulRosenblumPodcastSupport the show

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 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 into the business side of letting go, the emotional weight of being the person everyone relies on, and the very real questions around semi-retirement, succession, and where bookkeeping fits in an AI-shaped future.Support the show

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 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 that bookkeeping isn't data entry, it's responsibility, accuracy, and boundaries.Sound effect: https://freesound.org/people/metalfortress/sounds/611788/Be a part of the podcast by asking a question. Leave your voice message here: https://www.speakpipe.com/PaulRosenblumPodcastSupport the show

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 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.Support the show

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 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.Support the show

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 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 document unusual transactions, and why open communication between business owners and bookkeepers is essential to avoid costly mistakes. Because in bookkeeping, every dollar tells a story—and it's never just data entry.Support the show

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! Ever wondered what happens when a business partnership breaks up and the bookkeeper is left to pick up the pieces?Season 3 of The (Not Boring) Boring Small Business Bookkeeping and Accounting Podcast dives into the messy, human side of bookkeeping. Host Paul Rosenblum shares lessons from PPP audits, client complaints, and team-building wins and missteps. You'll get practical tips for starting a bookkeeping business, explore software alternatives to QuickBooks, and hear what really builds client trust during tax season chaos.This season isn't just about numbers. It's about the people behind them.

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! Ever wondered why bookkeepers are the real superheroes of the business world? It's because they master the intricacies of the chart of accounts, ensuring every income, cost of goods, and expense is perfectly categorized in the profit and loss (also known as the income statement). It may not sound like a superhero task to you when you first start tracking these accounts, but trust us, it IS! That's why our resident bookkeeper mensch, Paul Rosenblum delves into these 3 accounts … and more! More? Yes! There can be more to the income statement than these 3 accounts so be sure to listen through to the end for those extra special crispy accounts (okay, they may or may not be crispy but they are special and Paul will explain why). Episode 4: https://www.buzzsprout.com/2188873/12836056-accrual-vs-cash-based-accounting