The (Not Boring) Boring Small Business Bookkeeping and Accounting Podcast
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.
The (Not Boring) Boring Small Business Bookkeeping and Accounting Podcast
Who Decides If a Business Expense Is Tax Deductible? S10E02
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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.
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.
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S10E02: Who Decides If a Business Expense Is Tax Deductible?
I recently handed off a QuickBooks desktop file of a client to his tax preparer. He had a number of small questions about it.
One was the “Client Gift” category. Now, I know that the IRS allows $25.00 per year per client as a deductible expense, (and now you do too) and if the client gets audited, they could ask for the receipts.
This client had literally thousands of expense transactions during the year. I can’t, realistically, go through each and every one myself (even if the client has them all, which they don’t!). So, any transaction that I question, I put in the Ask My Client category (and send a spreadsheet every month to the client for them to fill out). I told him that I get the answers directly from the client on that monthly spreadsheet. The tax preparer suggested that I use my ‘judgement’, even if it is different from what the client puts on the spreadsheet. Do you agree with that?
I know the difference between a meal with a client or staff member is a deductible expense, and a meal only for the owner of a company in 2026 and moving forward should be entered as a ‘personal meal’ under an Equity ‘Draw’ or ‘Distribution’ account). But without receipts, sometimes it’s difficult to judge on exactly what category to enter these expenses in.
My philosophy is to tell the client what the rules are, and if they are having a meal by themselves, they should use their personal debit or credit card, and if with staff or a client, they should use their business debit or credit card. But in reality, that just doesn’t happen.
It’s the client’s tax return, not the tax preparer’s and not the bookkeepers. The tax preparers are responsible to make sure that there is no fraud on the tax return, but the client is responsible for the information that’s provided to the bookkeeper.
Bookkeepers out there -- How do you handle this? Leave me email or fan mail – I want to know!
As you do the bookkeeping, do you make decisions about what categories to enter transactions into to make the books 100% compatible with the IRS tax rules? How many tax preparers who you work with are this picky?
I’m Paul Rosenblum
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