“I was ready to frame my bookkeeper… for fraud or for incompetence. I wasn’t sure which.”
Meet Nina Castillo, a boutique wedding and lifestyle photographer based in the Berkshires of Massachusetts. Known for capturing those soft, golden-hour glows and candid love-drenched moments, Nina was a wizard with a camera. But when it came to the books? Let’s just say the picture wasn’t so pretty.
Part I: The Illusion of Trust
Like many creatives, Nina hired a freelance bookkeeper from a local Facebook group. The woman, let’s call her “Tina the Bookkeeper,” was warm, friendly, and reasonably priced. “I’ve worked with lots of small businesses,” she said. “I’ll keep you organized and ready for tax time.”
At first, things seemed fine. Nina handed over access to QuickBooks, bank feeds were linked, and she was told she’d get monthly reports. But then, three months in, Nina’s tax preparer emailed asking for year-end financials.
And Tina?
Ghosted.
She hadn’t reconciled the accounts in seven months. Bank feeds were a tangled mess. The PayPal account (where Nina collected half her deposits) wasn’t even connected. Expenses were all thrown into “Miscellaneous” or, worse, personal and business were mixed like a bad cocktail.
Part II: The Escape Attempt
Nina tried to sort it out herself. “How hard could it be?” she thought. But QuickBooks gave her a digital panic attack. Nothing balanced. Vendor names were misspelled, duplicates ran wild, and when she clicked on her profit and loss report—she burst into tears. It said she made $178,000 in profit.
She hadn’t even cleared $40k in the bank.
When she confronted Tina, she got a classic:
“Well, I just go off the bank feed. I thought you were handling receipts and categorizing.”
Tina had no engagement letter. No formal offboarding. Just a Google Drive folder and a mess.
Nina was stuck. She didn’t want to pay someone again to redo what she’d already paid for. But she knew she needed help.
Part III: Enter the Countess
When Nina finally contacted a professional bookkeeper (someone like the Countess, naturally), she was embarrassed.
Her opening email read:
“I know my books are a disaster. I’ve been trying to DIY them, and I hired someone who wasn’t qualified. Please don’t judge me.”
Oh, darling.
We never judge. But we do clean.
The Cleanup Plan
After a diagnostic review, here’s what we found:
- Two years of unreconciled accounts
- Duplicate income showing up from Stripe and PayPal
- Overstated income by nearly $90,000
- No mileage or home office tracked
- No Schedule C-ready reports for her CPA
Cost of Cleanup:
- $2,200 flat cleanup fee for two years
- $125/hr consulting to help Nina understand her reports, set up a workflow, and track expenses properly
- Monthly Bookkeeping: $275/month ongoing
- New Chart of Accounts setup: included in the cleanup
Total cleanup + onboarding: $1,750
Worth it? Absolutely. Her CPA estimated it saved her over $6,500 in overpaid taxes and missed deductions.
The Aftermath (a.k.a. Financial Clarity Looks Good on You)
Now, Nina checks her P&L each month with a glass of wine in hand and a tiara on (figuratively speaking, of course). She has clear revenue reports by service (weddings, portraits, product shoots), knows exactly what to set aside for taxes, and has monthly check-ins with her new bookkeeper who actually knows what they’re doing.
And Tina?
Let’s just say she’s no longer recommended in that Facebook group.
Countess’s Closing Thoughts:
Hiring the wrong bookkeeper can cost you more than money. It costs time, stress, and sometimes trust in your own business. A true professional doesn’t just plug in numbers—they partner with you.
If you’re a Nina—or you suspect you might be—don’t wait until tax season to find out. Book a cleanup consult with someone who can actually clean, not just cover up.
