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

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 bookkeepin...

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 sti...

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 ju...

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 cards, tangled business and personal transactions, and even a surprise closed bank account with missing rent payments. Unlike past episodes that offer broad tips, this one g...

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 client projects, catch up on multi-year financials, and prepare for the busy season ahead. You’ll see how strategic bookkeeping during quieter months builds...

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 own business, knowing what to track now will keep your books in top shape — and your future self will thank you. In this episode Paul covers personal med...

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 business owners more. If cash-based accounting is a jog, accrual accounting is a marathon... and your bookkeeper deserves more than just a granola...

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 real-world stories, hard-earned boundaries, and bookkeeping wisdom that helps you work smarter, not just harder—because sometimes the only thing messier th...

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 actually get your bookkeeping act together, starting with a simple checklist and some friendly guidance. Whether you're sorting receipts or sorting your life,...

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 your vacation fund. Spoiler alert: spending may go up, prices might follow, and the long-term effects could reshape the economy as we know it. But don’t worry—no sprea...

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 and the IRS to assess worker classification, highlighting the serious tax implications of misclassification and the challenges employers face in navigating th...

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 revenue or only include management fees. Understanding these choices is crucial for business owners, bookkeepers, and accountants to ensure accurate financi...

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 fiduciary duty and ethical responsibility, exploring how tax preparers navigate unpaid clients, financial missteps, and tricky legal gray areas. From handling o...

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 business examples, he helps bookkeepers and small business owners spot fair fees, value expertise, and make smarter pricing decisions. Send us Fan Mail Support the...

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 does a better job at laying out all the details for you. Let’s just say that if you’re a deep diver, you’re going to love this trend. Listen for the full detai...

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 you dot all those i’s and cross all those t’s (except in number form, because Bookkeeping, right?) Paul covers inheritance, insurance, workers comp, capital g...

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 he focuses on in December to prepare for tax season, such as prioritizing clients, reconciling accounts, and reviewing new tax laws. These preparation tasks help him...

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, is here to show you why this would be a mistake. A very big one. He’s even got specific examples when this type of situation goes wrong. Very wrong. Good i...

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.  Episode mentioned:  American Fast Food's Perception Problem, https://www.buzzsprout.com/2188873/episodes/15686396-american-fast-food-s-perception-problem Se...

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 shifts in tax, regulations, tariffs, minimum wage, and healthcare, focusing on what these could mean for business operations without diving into political...

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 that hit major bookkeeping snags because the partners weren’t communicating and didn’t have clear roles. They shared QuickBooks subscriptions, payments...

Have you thought about how the event that we dare not be reminded of from 2020 reshaped the way businesses manage their finances? Our resident Bookkeeping Mensch, Paul Rosenblum does. In this episode he’s sharing how accountants had to navigate constantly changing rules and regulations throughout that time. And now in 2024 the PPP program faces audits for potential fraud, which means that business...

"Why are fast food sales plummeting in the U.S.?" Our resident bookkeeping mensch, Paul Rosenblum, explores this surprising turn in the market. Rising prices and shifting consumer expectations, especially post-pandemic, have hurt major chains like McDonald's, Starbucks, and Subway. In response, some fast food companies are rebranding, offering discounts, and improving customer exper...

Vacation is supposed to be relaxing, but what if your stay doesn’t live up to your expectations? That’s what happened to our resident Bookkeeper Mensch, Paul Rosenblum, during his recent South Carolina getaway. While most of the trip was great, the accommodations had a few problems. But instead of just complaining, Paul is here to share the surprising outcome and what small business owners can lea...

Why should you, a small business owner, prioritize treating customers well instead of focusing solely on your bottom line? That’s what our favorite bookkeeping mensch,   Paul Rosenblum, has been doing for over 2 decades. So on the 30th anniversary of the McDonald's Hot Coffee Case (yes, it’s been that long), he’s taking a look at what happened and what could have happened instead. Because as...