From the “Bridging the Gap” Series

You can have a bookkeeper, a CPA, and still be losing money.
Not because someone’s doing anything wrong—
but because no one’s looking close enough.

In Part 1, we broke down the roles.
In Part 2, we talked about the questions no one else is asking.
Now let’s talk about the cracks—
the places where money quietly disappears unless someone’s trained to notice.

Common Places Where Money Slips Through

1. Misclassified Expenses

That $500 Zoom invoice?
It’s sitting under “Software – Office” when it could’ve been under “Training & Communication,” which would’ve given you a stronger deduction depending on your industry.

Why it matters: Misclassification doesn’t just hurt tax strategy—it distorts your reporting. 

I myself have encountered this, I classified Spotify as ‘Continuing Education’ and my CPA classified it as ‘Dues/Subscriptions/Memberships.’ Too much in one category is a red flag, as well as throwing my numbers off. 

2. Duplicate Charges or Subscriptions

I once found a client was paying for two versions of the same CRM, one billed monthly and one annually.
Nobody caught it—not even the bookkeeper—because the names were slightly different on the statements.

I also had my bookkeeper list my reimbursements as duplicate charges. 

Why it matters: These small leaks compound. And you can’t cut what you can’t see.

3. Personal Expenses Hidden in Business Accounts

Let’s be real—blended spending happens, especially for solopreneurs.
But what often slips through?

• Grocery store stops during supply runs

• Amazon charges that mix personal and business

• Meals with no documentation

Why it matters: If left unaddressed, these can trigger IRS red flags—or missed legit write-offs.

4. Recurring Expenses That No Longer Serve You

Are you still paying for:

• An old email platform?

• A coaching program you forgot to cancel?

• Apps or tools you haven’t used in months?

Why it matters: Every unused subscription is a quiet profit drain.

5. Revenue Looks Good—But the Bank Balance Doesn’t

One of the biggest wake-up calls is when a client says:

“We had our best quarter ever… but we’re still tight on cash.”

Why it matters: That disconnect usually means:

• Poor receivables follow-up

• Overextended credit

• Pricing that isn’t aligned with cost

My Process: How I Catch What Others Miss

When I come in, I don’t just read the numbers—I listen to them.

I:

• Review transactions line-by-line

• Cross-check vendor names, payment patterns, and logic

• Ask “Does this make sense?” before categorizing

• Create a clean picture that supports decisions, not just filings

Final Thought

This is where the gap gets expensive.
If no one is zooming in and asking the right questions, money will keep slipping through—even if the reports look “clean.”

Want a second set of eyes on your financial cracks?
Schedule a consultation—I’ll show you what’s being missed and how to fix it.