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

By Paul Rosenblum | 25+ Years of Bookkeeping, Small Business Finances, and Tax InsightsBusiness Entrepreneurship Education How To

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

August 06 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
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About the host
Paul Rosenblum has been doing hands-on bookkeeping for over 30 years, starting with QuickBooks Desktop.
👀 Why Niche Podcasts Are The Bedrock Of The Industry: https://podalization.substack.com/p/why-niche-podcasts-are-the-bedrock
😄 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: [email protected]
📰 Substack: https://paulrosenblum.substack.com/
💸 Website: https://bookkeepermensch.com
🎧 Get help with your podcast with PodcastSteph https://podcaststeph.substack.com/p/the-5-paths-to-podcast-discoverability
🎵 Music: SourceAudio: https://www.sourceaudio.com/
🔉 Sound effects: https://freesound.org
Interview with Mary: ...
11 min
July 30 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.
👀 Why Niche Podcasts Are The Bedrock Of The Industry: https://podalization.substack.com/p/why-niche-podcasts-are-the-bedrock
😄 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: [email protected]
📰 Substack: https://paulrosenblum.substack.com/
💸 Website: https://bookkeepermensch.com
🎧 Get help with your podcast with PodcastSteph https://podcaststeph.substack.com/p/the-5-paths-to-podcast-discoverability
🎵 Music: SourceAudio: https://www.sourceaudio.com/
🔉 Sound effects: https://freesound.org
Interview with Mary: ...
4 min
July 23 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.
👀 Why Niche Podcasts Are The Bedrock Of The Industry: https://podalization.substack.com/p/why-niche-podcasts-are-the-bedrock
😄 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: [email protected]
📰 Substack: https://paulrosenblum.substack.com/
💸 Website: https://bookkeepermensch.com
🎧 Get help with your podcast with PodcastSteph https://podcaststeph.substack.com/p/the-5-paths-to-podcast-discoverability
🎵 Music: SourceAudio: https://www.sourceaudio.com/
🔉 Sound effects: https://freesound.org
Interview with Mary: ...
17 min
July 16 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.
👀 Why Niche Podcasts Are The Bedrock Of The Industry: https://podalization.substack.com/p/why-niche-podcasts-are-the-bedrock
😄 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: [email protected]
📰 Substack: https://paulrosenblum.substack.com/
💸 Website: https://bookkeepermensch.com
🎧 Get help with your podcast with PodcastSteph https://podcaststeph.substack.com/p/the-5-paths-to-podcast-discoverability
🎵 Music: SourceAudio: https://www.sourceaudio.com/
🔉 Sound effects: https://freesound.org
Interview with Mary: ...
3 min
July 09 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.
👀 Why Niche Podcasts Are The Bedrock Of The Industry: https://podalization.substack.com/p/why-niche-podcasts-are-the-bedrock
😄 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: [email protected]
📰 Substack: https://paulrosenblum.substack.com/
💸 Website: https://bookkeepermensch.com
🎧 Get help with your podcast with PodcastSteph https://podcaststeph.substack.com/p/the-5-paths-to-podcast-discoverability
🎵 Music: SourceAudio: https://www.sourceaudio.com/
🔉 Sound effects: https://freesound.org
Interview with Mary: ...
19 min
June 25 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.
👀 Why Niche Podcasts Are The Bedrock Of The Industry: https://podalization.substack.com/p/why-niche-podcasts-are-the-bedrock
😄 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: [email protected]
📰 Substack: https://paulrosenblum.substack.com/
💸 Website: https://bookkeepermensch.com
🎧 Get help with your podcast with PodcastSteph https://podcaststeph.substack.com/p/the-5-paths-to-podcast-discoverability
🎵 Music: SourceAudio: https://www.sourceaudio.com/
🔉 Sound effects: https://freesound.org
Interview with Mary: ...
4 min
June 18 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.
👀 Why Niche Podcasts Are The Bedrock Of The Industry: https://podalization.substack.com/p/why-niche-podcasts-are-the-bedrock
😄 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: [email protected]
📰 Substack: https://paulrosenblum.substack.com/
💸 Website: https://bookkeepermensch.com
🎧 Get help with your podcast with PodcastSteph https://podcaststeph.substack.com/p/the-5-paths-to-podcast-discoverability
🎵 Music: SourceAudio: https://www.sourceaudio.com/
🔉 Sound effects: https://freesound.org
Interview with Mary: ...
15 min
June 11 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.
👀 Why Niche Podcasts Are The Bedrock Of The Industry: https://podalization.substack.com/p/why-niche-podcasts-are-the-bedrock
😄 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: [email protected]
📰 Substack: https://paulrosenblum.substack.com/
💸 Website: https://bookkeepermensch.com
🎧 Get help with your podcast with PodcastSteph https://podcaststeph.substack.com/p/the-5-paths-to-podcast-discoverability
🎵 Music: SourceAudio: https://www.sourceaudio.com/
🔉 Sound effects: https://freesound.org
Interview with Mary: ...
4 min
June 04 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 industry may be headed next. Just don’t listen while hungry unless you’re financially and emotionally prepared for a drive-thru run afterward.
Previous Fast Food episode:
https://pod.link/1688000860/episode/QnV6enNwcm91dC0xNTY4NjM5Ng
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.
👀 Why Niche Podcasts Are The Bedrock Of The Industry: https://podalization.substack.com/p/why-niche-podcasts-are-the-bedrock
😄 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: [email protected]
📰 Substack: https://paulrosenblum.substack.com/
💸 Website: https://bookkeepermensch.com
🎧 Get help with your podcast with PodcastSteph https://podcaststeph.substack.com/p/the-5-paths-to-podcast-discoverability
🎵 Music: SourceAudio: https://www.sourceaudio.com/
🔉 Sound effects: https://freesound.org
Interview with Mary: ...
14 min
May 28 Signing a Commercial Lease? Top Risks Small Business Owners Need to Know. S9E5
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 stress, disruption, and money in the long run.
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.
👀 Why Niche Podcasts Are The Bedrock Of The Industry: https://podalization.substack.com/p/why-niche-podcasts-are-the-bedrock
😄 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: [email protected]
📰 Substack: https://paulrosenblum.substack.com/
💸 Website: https://bookkeepermensch.com
🎧 Get help with your podcast with PodcastSteph https://podcaststeph.substack.com/p/the-5-paths-to-podcast-discoverability
🎵 Music: SourceAudio: https://www.sourceaudio.com/
🔉 Sound effects: https://freesound.org
Interview with Mary: ...
3 min

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

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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…