When Bookkeeping Goes Wrong: A Mission-Driven Advisor On Protecting Your Business

If you run a business, this episode could save you from sleepless nights and costly mistakes. Rachel Michaelov, founder of Empire Tax Advisors and partner in Practice Wealth Partners, shares the deeply personal story that fueled her career and the practical systems that keep owners audit ready, tax efficient, and in control. You will learn how to choose the right entity, what your bookkeeper might be missing, and the exact questions to ask so you never assume someone else has it covered. Whether you are a solo founder, a growing service firm, or a dentist building wealth, this conversation turns “I didn’t know” into “I’ve got this.”

What You’ll Learn in This Episode

The Hidden Cost of Assumptions: Why relying on “someone recommended my accountant” can still lead to sales tax trouble, IRS notices, and avoidable audits. How to set roles and expectations in writing so nothing falls through the cracks.

Entity Choice That Actually Saves You Money: When staying a sole proprietor or single-member LLC becomes a tax trap. How and when electing S Corp status can reduce self-employment taxes once you cross the 60–70k income range.

Bookkeeping for Taxes, Not Just for Data Entry: The difference between generic categorizing and tax-smart books. Why every transaction needs a purpose under IRS rules and how proactive questions turn trips, meals, cars, and phones into properly documented deductions.

Sales Tax Compliance Made Understandable: The rule New York State cares about most. Why “I didn’t charge it” does not mean “I don’t owe it,” and how to set simple quarterly systems so you are never surprised.

Payroll, Depreciation, and Accountable Plans: The S Corp basics owners miss. How to pay yourself correctly, depreciate big purchases the right way, and reimburse mixed-use expenses like your phone with clean documentation.

For Dentists and Practice Owners: The all-in-one approach Rachel’s team uses to bring books current, resolve liabilities, and implement strategies that have saved clients significant amounts in taxes while restoring peace of mind.

Due Diligence You Can Use Today: A short checklist to vet your accountant: licenses (EA, CPA, or attorney), years of relevant experience, proactive planning, monthly reconciliations, tax-driven bookkeeping, and clear written scope.