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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

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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: Bookkeepermensch@gmail.com

🦉 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

😄 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: Bookkeepermensch@gmail.com

🦉 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.

Support the show

😄 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: Bookkeepermensch@gmail.com

🦉 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

😄 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: Bookkeepermensch@gmail.com

🦉 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!

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

Support the show

😄 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: Bookkeepermensch@gmail.com

🦉 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!

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.

Support the show

😄 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: Bookkeepermensch@gmail.com

🦉 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!

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

Support the show

😄 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: Bookkeepermensch@gmail.com

🦉 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!

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.

Support the show

😄 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: Bookkeepermensch@gmail.com