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

Paul Rosenblum, Bookkeeping Mensch
  • 5.0 (8)
  • ENTREPRENEURSHIP
  • UPDATED SEMIMONTHLY

If you’ve ever felt stuck in the digits, this show brings your business personality to the forefront. We go beyond spreadsheets to talk about the relationships that make businesses thrive—between bookkeepers, clients, accountants, and financial professionals.Welcome to The Not Boring, Boring Bookkeeping and Small Business Podcast—where we explore the human side of bookkeeping and business.Hosted by Paul Rosenblum, a New York-based bookkeeper with over 30 years of experience and decades teaching QuickBooks, this podcast is for bookkeepers and small business owners who know business is about more than just numbers.🎧 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.

  1. When DIY Bookkeeping Meets Pre-Tax Season

    NOV 6

    When DIY Bookkeeping Meets Pre-Tax Season

    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 📞 Leave a voice message for Paul: https://www.speakpipe.com/PaulRosenblumPodcast 😄 Send him a text message (remember to include your contact info) 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: Bookkeepermensch@gmail.com

    18 min
  2. Haunted by 1099s: PayPal, Venmo & the New Rules

    OCT 23

    Haunted by 1099s: PayPal, Venmo & the New Rules

    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 📞 Leave a voice message for Paul: https://www.speakpipe.com/PaulRosenblumPodcast 😄 Send him a text message (remember to include your contact info) 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: Bookkeepermensch@gmail.com

    12 min
  3. Getting Cash, Payroll, and Petty Cash Right

    OCT 9

    Getting Cash, Payroll, and Petty Cash Right

    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 📞 Leave a voice message for Paul: https://www.speakpipe.com/PaulRosenblumPodcast 😄 Send him a text message (remember to include your contact info) 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: Bookkeepermensch@gmail.com

    12 min
  4. What does ‘cash on hand’ mean in bookkeeping?

    SEP 18

    What does ‘cash on hand’ mean in bookkeeping?

    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 your POS totals don’t match your bank deposits, the mystery usually comes down to three little words.  Don't worry, our favorite Bookkeeping Mensch, Paul Rosenblum, is here to break down the tricky world of cash on hand. From POS systems and sales tax to tips, deposits, and those frustrating month-end discrepancies, he explains how this account works, why it’s so confusing, and what both bookkeepers and business owners need to understand, including: 💳 How POS systems track sales, tax, and tips🏦 Why deposits rarely match end-of-month sales📊 What “cash on hand” looks like in the books💵 Common mistakes with cash, checks, and payroll🤝 How communication between owners and bookkeepers prevents messy booksWith real-world examples and clear explanations, Paul gives you the clarity and confidence to spot cash-on-hand issues before they snowball into messy books and costly fixes. Be a part of the podcast by asking a question. Leave your voice message here: https://www.speakpipe.com/PaulRosenblumPodcast Support the show 📞 Leave a voice message for Paul: https://www.speakpipe.com/PaulRosenblumPodcast 😄 Send him a text message (remember to include your contact info) 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: Bookkeepermensch@gmail.com

    25 min
  5. Bookkeeping Q&A: Get Ahead Before Tax Season Hits

    SEP 4

    Bookkeeping Q&A: Get Ahead Before Tax Season Hits

    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! QuickBooks, 1099s, Affirm, Cars, Chaos. 👉 Bookkeepers and Business owners can’t afford to wait until tax season to get organized. In this first-ever Q&A episode, Paul Rosenblum — Our Favorite Bookkeeping Mensch — tackles real listener questions about: ✅ When to start fresh in QuickBooks ✅ How to reconcile every account (banks, loans, investments) ✅ What the new 1099 thresholds mean ✅ The right way to handle Affirm loans and vehicle financing Paul also shares a candid story about client delays and missing access that turned into a last-minute scramble, raising the bigger question: why do bookkeepers stop everything at the wrong time?  💬 Send your questions anytime at BookkeeperMensch.com Sound effect:  old cash register open and close with a bing by clubmydia+ -- https://freesound.org/s/584168/ -- License: Creative Commons 0 Be a part of the podcast by asking a question. Leave your voice message here: https://www.speakpipe.com/PaulRosenblumPodcast Support the show 📞 Leave a voice message for Paul: https://www.speakpipe.com/PaulRosenblumPodcast 😄 Send him a text message (remember to include your contact info) 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: Bookkeepermensch@gmail.com

    20 min
  6. Two Bookkeeping Mistakes That Cost More Than You Think

    AUG 21

    Two Bookkeeping Mistakes That Cost More Than You Think

    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 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 bookkeeping changes can spiral into time-consuming, expensive messes—and how to avoid costly manual work and delays through better planning and access sharing. These simple communication habits will keep your books (and your bookkeeper) in great shape. Support the show 📞 Leave a voice message for Paul: https://www.speakpipe.com/PaulRosenblumPodcast 😄 Send him a text message (remember to include your contact info) 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: Bookkeepermensch@gmail.com

    13 min
  7. Two Connected Businesses, One Bookkeeper’s Brain

    AUG 7

    Two Connected Businesses, One Bookkeeper’s Brain

    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 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 still overlapping. Add in mismatched credit lines, reconciliation headaches, and a full year-end merge ahead, and it’s clear this isn’t your average summer catch-up. Paul also begins testing alternatives to QuickBooks and shares a clever IT workaround that extends the life of an old office computer. For a behind-the-scenes look at layered bookkeeping decisions and the calm, strategic thinking they require, listen to the full episode. Be a part of the podcast by asking a question. Leave your voice message here: https://www.speakpipe.com/PaulRosenblumPodcast Support the show 📞 Leave a voice message for Paul: https://www.speakpipe.com/PaulRosenblumPodcast 😄 Send him a text message (remember to include your contact info) 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: Bookkeepermensch@gmail.com

    11 min
  8. LLC to S Corp? A Bookkeeper’s POV

    JUL 22

    LLC to S Corp? A Bookkeeper’s POV

    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 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. Support the show 📞 Leave a voice message for Paul: https://www.speakpipe.com/PaulRosenblumPodcast 😄 Send him a text message (remember to include your contact info) 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: Bookkeepermensch@gmail.com

    14 min
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About

If you’ve ever felt stuck in the digits, this show brings your business personality to the forefront. We go beyond spreadsheets to talk about the relationships that make businesses thrive—between bookkeepers, clients, accountants, and financial professionals.Welcome to The Not Boring, Boring Bookkeeping and Small Business Podcast—where we explore the human side of bookkeeping and business.Hosted by Paul Rosenblum, a New York-based bookkeeper with over 30 years of experience and decades teaching QuickBooks, this podcast is for bookkeepers and small business owners who know business is about more than just numbers.🎧 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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