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

Hosted by Paul Rosenblum | 25+ Years of Bookkeeping, Small Business Finances, and Tax Insights

Business Entrepreneurship Education

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Aug 2026

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If you’re a small business owner or bookkeeper trying to make sense of bookkeeping, business finances, QuickBooks, cash flow, and tax-ready systems without drowning in accounting jargon, this podcast is for you. Welcome to The Not Boring, Boring Bookkeeping and Small Business Podcast , where bookkeeping meets real business life. Beyond spreadsheets and expense tracking, our favorite Bookkeeping Mensch, Paul Rosenblum, explores the human side of small business finances and the relationships between bookkeepers, clients, accountants, and financial professionals that keep businesses running smoothly. Paul is a New York-based bookkeeper with over 25 years of experience and decades teaching QuickBooks. In this podcast he shares practical bookkeeping tips, small business finance insights, tax deduction guidance, and real-world lessons from working with business owners every day. Whether you’re managing your own books, learning QuickBooks Online, or trying to build better financial systems for your business, you’ll find approachable, experience-based advice without the boring lecture style. 🎧 Listen to episodes like: -Bookkeepers Are More Than Bean Counters -How Communication Impacts Your Bookkeeping -Plus hands-on tools like QuickBooks basics, startup expenses, and chart of accounts.

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August 20, 2026Episode 514 min

How to Spot Bad Bookkeeping Before It Becomes a Tax Problem: S10E05

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 deposit lands in the wrong category. That same pattern shows up in a second cleanup, this time involving a business that started as a sole proprietorship before becoming a corporation in 2023. Unpaid sales tax, unfiled taxes, and business expenses running through personal accounts have turned the job into a years-long reconstruction. Together, these two projects make the larger point clear: bookkeeping is much more than reconciling accounts, and business owners need someone who understands the accounting behind QuickBooks, asks the right questions, and knows when the numbers don’t make sense. The longer those mistakes sit, the harder and more expensive they become to untangle. Part 1: https://pod.link/1688000860/episode/QnV6enNwcm91dC0xOTUwMjg1NQ Part 2: https://pod.link/1688000860/episode/QnV6enNwcm91dC0xOTU3MDIzNA Send us Fan Mail Support the show About the host Paul Rosenblum has been doing hands-on bookkeeping for over 30 years, starting with QuickBooks Desktop and adapting to the world of cloud-based QuickBooks Online. He shares practical, in-the-weeds lessons from real client files every episode. 😄 Send Paul a text or 📞 voice message (include your contact info if you want a reply) https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms 📨 Email: Bookkeepermensch@gmail.com 👀 $20 discount when you host your podcast on Buzzsprout: https://www.buzzsprout.com/?referrer_id=2022201 💸 Website: https://bookkeepermensch.com 🎧 Producer Steph: https://linktr.ee/stephfuccio 🎵 Music: SourceAudio: https://www.sourceaudio.com/ 🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/ 👀 We got reviewed! Why an Indie Accounting Podcast Is Not Boring! https://vocal.media/trader/why-an-indie-accounting-podcast-is-not-boring

August 13, 2026Episode 43 min

Roth vs. Traditional IRA: Which One Fits Your Tax Picture? S10E04

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 Send us Fan Mail Support the show About the host Paul Rosenblum has been doing hands-on bookkeeping for over 30 years, starting with QuickBooks Desktop and adapting to the world of cloud-based QuickBooks Online. He shares practical, in-the-weeds lessons from real client files every episode. 😄 Send Paul a text or 📞 voice message (include your contact info if you want a reply) https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms 📨 Email: Bookkeepermensch@gmail.com 👀 $20 discount when you host your podcast on Buzzsprout: https://www.buzzsprout.com/?referrer_id=2022201 💸 Website: https://bookkeepermensch.com 🎧 Producer Steph: https://linktr.ee/stephfuccio 🎵 Music: SourceAudio: https://www.sourceaudio.com/ 🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/ 👀 We got reviewed! Why an Indie Accounting Podcast Is Not Boring! https://vocal.media/trader/why-an-indie-accounting-podcast-is-not-boring

August 6, 2026Episode 310 min

Fixing 6 Credit Cards and a Bookkeeping IRS Mistake: S10E03

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 reality. Along the way, he uncovers a compliance issue that goes beyond typical cleanup: one business partner had been running a separate, wholly-owned LLC that was billed as a subcontractor to the company. This is something that the IRS doesn't allow when that partner also owns a stake in the business being billed. With the profit and loss nearly finished, Paul turns to the balance sheet: sorting out the equity split between two partners, tracking down company assets and home-office expenses that were never recorded, and weighing a tricky judgment call on categorizing meals between business partners, all against unclear new 2026 rules on meal deductions. This is a grounded look at what it actually takes to turn a multi-year mess into books a tax preparer can trust. No shortcuts, and no AI required. Part 1: https://pod.link/1688000860/episode/QnV6enNwcm91dC0xOTUwMjg1NQ Send us Fan Mail Support the show About the host Paul Rosenblum has been doing hands-on bookkeeping for over 30 years, starting with QuickBooks Desktop and adapting to the world of cloud-based QuickBooks Online. He shares practical, in-the-weeds lessons from real client files every episode. 😄 Send Paul a text or 📞 voice message (include your contact info if you want a reply) https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms 📨 Email: Bookkeepermensch@gmail.com 👀 $20 discount when you host your podcast on Buzzsprout: https://www.buzzsprout.com/?referrer_id=2022201 💸 Website: https://bookkeepermensch.com 🎧 Producer Steph: https://linktr.ee/stephfuccio 🎵 Music: SourceAudio: https://www.sourceaudio.com/ 🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/ 👀 We got reviewed! Why an Indie Accounting Podcast Is Not Boring! https://vocal.media/trader/why-an-indie-accounting-podcast-is-not-boring

July 30, 2026Episode 23 min

Who Decides If a Business Expense Is Tax Deductible? S10E02

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. Send us Fan Mail Support the show About the host Paul Rosenblum has been doing hands-on bookkeeping for over 30 years, starting with QuickBooks Desktop and adapting to the world of cloud-based QuickBooks Online. He shares practical, in-the-weeds lessons from real client files every episode. 😄 Send Paul a text or 📞 voice message (include your contact info if you want a reply) https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms 📨 Email: Bookkeepermensch@gmail.com 👀 $20 discount when you host your podcast on Buzzsprout: https://www.buzzsprout.com/?referrer_id=2022201 💸 Website: https://bookkeepermensch.com 🎧 Producer Steph: https://linktr.ee/stephfuccio 🎵 Music: SourceAudio: https://www.sourceaudio.com/ 🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/ 👀 We got reviewed! Why an Indie Accounting Podcast Is Not Boring! https://vocal.media/trader/why-an-indie-accounting-podcast-is-not-boring

July 23, 2026Episode 116 min

How Bad Bookkeeping Hurts Your Business: S10E01

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 appeared to be a routine cleanup uncovered missing bank accounts, unrecorded credit cards, unreconciled transactions, and financial reports that couldn't be trusted. Along the way, he explores the importance of tax loss carryforwards and demonstrates why bookkeeping is far more than data entry. Accurate books provide the foundation for business decisions, tax planning, financial reporting, and long-term growth. Paul continues untangling this client's books in the episodes ahead, working through the credit cards, balance sheet, and compliance issues that emerge along the way. Mentioned in this episode: Does Bookkeeping Need To Be More Regulated? S7E4 https://pod.link/1688000860/episode/QnV6enNwcm91dC0xODcxMTY0Ng Send us Fan Mail Support the show About the host Paul Rosenblum has been doing hands-on bookkeeping for over 30 years, starting with QuickBooks Desktop and adapting to the world of cloud-based QuickBooks Online. He shares practical, in-the-weeds lessons from real client files every episode. 😄 Send Paul a text or 📞 voice message (include your contact info if you want a reply) https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms 📨 Email: Bookkeepermensch@gmail.com 👀 $20 discount when you host your podcast on Buzzsprout: https://www.buzzsprout.com/?referrer_id=2022201 💸 Website: https://bookkeepermensch.com 🎧 Producer Steph: https://linktr.ee/stephfuccio 🎵 Music: SourceAudio: https://www.sourceaudio.com/ 🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/ 👀 We got reviewed! Why an Indie Accounting Podcast Is Not Boring! https://vocal.media/trader/why-an-indie-accounting-podcast-is-not-boring

July 16, 2026Episode 112 min

What Debts Are Forgiven When Someone Dies? S9E11

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. Send us Fan Mail Support the show About the host Paul Rosenblum has been doing hands-on bookkeeping for over 30 years, starting with QuickBooks Desktop and adapting to the world of cloud-based QuickBooks Online. He shares practical, in-the-weeds lessons from real client files every episode. 😄 Send Paul a text or 📞 voice message (include your contact info if you want a reply) https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms 📨 Email: Bookkeepermensch@gmail.com 👀 $20 discount when you host your podcast on Buzzsprout: https://www.buzzsprout.com/?referrer_id=2022201 💸 Website: https://bookkeepermensch.com 🎧 Producer Steph: https://linktr.ee/stephfuccio 🎵 Music: SourceAudio: https://www.sourceaudio.com/ 🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/ 👀 We got reviewed! Why an Indie Accounting Podcast Is Not Boring! https://vocal.media/trader/why-an-indie-accounting-podcast-is-not-boring

July 9, 2026Episode 1018 min

How to Reduce Bookkeeping Errors in QuickBooks Online: S9E10

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 smoothly for your QBO experiences. Send us Fan Mail Support the show About the host Paul Rosenblum has been doing hands-on bookkeeping for over 30 years, starting with QuickBooks Desktop and adapting to the world of cloud-based QuickBooks Online. He shares practical, in-the-weeds lessons from real client files every episode. 😄 Send Paul a text or 📞 voice message (include your contact info if you want a reply) https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms 📨 Email: Bookkeepermensch@gmail.com 👀 $20 discount when you host your podcast on Buzzsprout: https://www.buzzsprout.com/?referrer_id=2022201 💸 Website: https://bookkeepermensch.com 🎧 Producer Steph: https://linktr.ee/stephfuccio 🎵 Music: SourceAudio: https://www.sourceaudio.com/ 🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/ 👀 We got reviewed! Why an Indie Accounting Podcast Is Not Boring! https://vocal.media/trader/why-an-indie-accounting-podcast-is-not-boring

June 25, 2026Episode 93 min

2026 Tax Brackets Overview: S9E9

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 Send us Fan Mail Support the show About the host Paul Rosenblum has been doing hands-on bookkeeping for over 30 years, starting with QuickBooks Desktop and adapting to the world of cloud-based QuickBooks Online. He shares practical, in-the-weeds lessons from real client files every episode. 😄 Send Paul a text or 📞 voice message (include your contact info if you want a reply) https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms 📨 Email: Bookkeepermensch@gmail.com 👀 $20 discount when you host your podcast on Buzzsprout: https://www.buzzsprout.com/?referrer_id=2022201 💸 Website: https://bookkeepermensch.com 🎧 Producer Steph: https://linktr.ee/stephfuccio 🎵 Music: SourceAudio: https://www.sourceaudio.com/ 🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/ 👀 We got reviewed! Why an Indie Accounting Podcast Is Not Boring! https://vocal.media/trader/why-an-indie-accounting-podcast-is-not-boring

June 18, 2026Episode 814 min

The Hidden Bookkeeping Money Decisions You Make Every Day: S9E8

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. Send us Fan Mail Support the show About the host Paul Rosenblum has been doing hands-on bookkeeping for over 30 years, starting with QuickBooks Desktop and adapting to the world of cloud-based QuickBooks Online. He shares practical, in-the-weeds lessons from real client files every episode. 😄 Send Paul a text or 📞 voice message (include your contact info if you want a reply) https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms 📨 Email: Bookkeepermensch@gmail.com 👀 $20 discount when you host your podcast on Buzzsprout: https://www.buzzsprout.com/?referrer_id=2022201 💸 Website: https://bookkeepermensch.com 🎧 Producer Steph: https://linktr.ee/stephfuccio 🎵 Music: SourceAudio: https://www.sourceaudio.com/ 🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/ 👀 We got reviewed! Why an Indie Accounting Podcast Is Not Boring! https://vocal.media/trader/why-an-indie-accounting-podcast-is-not-boring

June 11, 2026Episode 73 min

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 give you something to think about. Send us Fan Mail Support the show About the host Paul Rosenblum has been doing hands-on bookkeeping for over 30 years, starting with QuickBooks Desktop and adapting to the world of cloud-based QuickBooks Online. He shares practical, in-the-weeds lessons from real client files every episode. 😄 Send Paul a text or 📞 voice message (include your contact info if you want a reply) https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms 📨 Email: Bookkeepermensch@gmail.com 👀 $20 discount when you host your podcast on Buzzsprout: https://www.buzzsprout.com/?referrer_id=2022201 💸 Website: https://bookkeepermensch.com 🎧 Producer Steph: https://linktr.ee/stephfuccio 🎵 Music: SourceAudio: https://www.sourceaudio.com/ 🔉 Sound effects: https://freesound.org/people/metalfortress/sounds/611788/ 👀 We got reviewed! Why an Indie Accounting Podcast Is Not Boring! https://vocal.media/trader/why-an-indie-accounting-podcast-is-not-boring