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

July 22, 2025 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: Impossible” episode. Listen in to learn what really happens when clean books meet messy business changes.
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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
15 min
July 08, 2025 QuickBooks Chaos to Clarity Case Study: S5E7
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 gets into the gritty details of how he actually solves these problems using both traditional and unconventional QuickBooks methods. He highlights the importance of client communication, the reality of adjusting workflows on the fly, and why he’s now focusing on respectful, high-quality clients
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
14 min
June 17, 2025 Bookkeeping Off-Season Planning That Pays Off: S5E6
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 a foundation for smoother, more accurate reporting when business picks up. The episode delivers a clear message: by investing effort when things are quiet, you buy yourself control, confidence, and breathing room when it’s sheer chaos. Whether you’re a bookkeeper managing big projects or a business owner trying to stay ahead, this episode is a masterclass in planning with purpose.
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
14 min
June 16, 2025 Get Early Access to New Episodes
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😄 Send Paul a message. (add your email for a reply). https://www.buzzsprout.com/twilio/text_messages/2188873/open_sms

🎧 Podcast production & Growth: https://www.coffeelikemedia.com/

💸 Website: https://bookkeepermensch.com

🎵 Music: SourceAudio: https://www.sourceaudio.com/

📨 Email: [email protected]

2 min
June 06, 2025 Prepare Your Bookkeeping Deductions Early: S5E5
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 medical expenses to powerful business deductions like Section 179 and bonus depreciation. In essence, what matters most for 2025 tax prep.
Speaking of deductions, why did the bookkeeper bring a ladder to work? Because they heard the deductions were through the roof!
Links:
Tax rate chart:
https://www.linkedin.com/posts/paul-rosenblum-b284a3_smallbusiness-taxes-accounting-activity-7336864838956015619-J2-U
Episode 1:
https://www.buzzsprout.com/2188873/episodes/12836059-start-up-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
12 min
May 22, 2025 Why Accrual Accounting Costs More: S5E4
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 bar at the finish line.
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
19 min
May 08, 2025 Bookkeeping Without the Burnout: S5E3
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 than mixed finances is your client’s idea of “organized.”
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
18 min
April 24, 20252024 Bookkeeping Checklist: What to Do After Tax Season: S5E2
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, he's got you covered—with just enough dry humor to keep it fun. After all, when it comes to getting your books in order, sometimes you need a laugh as much as a ledger.
Accounting software: eps 3, 30, 31
Accrual or cash accounting: ep 4
Start up expenses: ep 1
Chart of accounts: eps 7, 35, 36
Relationships in Bookkeeping: eps 14, 38
Partnership, LLC or S-Corp: eps 28, 44
Accounts receivable & accounts payable: eps 18, 19
McDonald’s hot coffee case: ep 40
Common bookkeeping mistakes: ep 39
Paul’s bookkeeping origin story: ep 20
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
9 min
April 10, 2025 No Income Tax: Boom or Bust? S5E1
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 spreadsheets were harmed in the making of this episode.
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
16 min
March 27, 2025 Classifying Workers: Rules, Risks, and Red Flags: S4E10
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 these rules. Turns out, bookkeeping isn’t just about numbers—it’s also about dodging financial punches… speaking of which, why did the bookkeeper break up with the calculator? It couldn’t handle their negative balance!
Episodes mentioned:
- W2 or 1099...The Question That Haunts Business Owners (ep 5)
https://www.buzzsprout.com/2188873/episodes/12836055-w2-or-1099-the-question-that-haunts-business-owners
- W2 or 1099: A closer look (ep 6)
https://www.buzzsprout.com/2188873/episodes/12836054-w2-or-1099-a-closer-look
- 1099 Reporting Changes (ep 21)
https://www.buzzsprout.com/2188873/episodes/13852295-1099-reporting-changes
- QuickBooks no more? (ep 26)
https://www.buzzsprout.com/2188873/episodes/14240698-quickbooks-no-more
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
14 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…