Bookkeeping Q&A: Get Ahead Before Tax Season Hits: S6E1

The (Not Boring) Boring Small Business Bookkeeping and Accounting Podcast · Sep 4, 2025 · 19m

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…