Dear Dangerously in Love with Finance,
I’m a dentist in Portland and I’m sick to my stomach. Last month, I found out my office manager of seven years stole at least $180K from me. Maybe more. I trusted this woman completely. She handled payroll, insurance claims, vendor payments, everything.
I finally caught on when supply costs kept rising but we weren’t seeing more patients. When I looked at bank statements (yeah, should’ve done that sooner), there were random transfers to accounts I didn’t recognize. She’d set up fake vendors and paid herself through those. She was also skimming cash payments that never got deposited. I was signing checks to companies that didn’t even exist. She’d just hand me a stack and I’d sign them without looking.
I filed a police report, got a lawyer, and fired her. But now what? How do I make sure this never happens again? I can’t afford some big accounting firm. Honestly, I don’t know what I’m looking for when I look at financial reports. She was writing checks, moving money around. I had no clue what was normal and what wasn’t. My dad always said “stick to teeth, hire good people for the rest.” Well, look where that got me.
Do I need to check things weekly? Hire two people so they watch each other? How do I interview without being paranoid about every candidate? I’ve got staff freaking out. Patients are asking questions. And I’m supposed to go back to doing root canals like nothing happened.
What should I be doing here?
Signed,
Drilling for Answers in Portland
Dear Drilling,
Stop beating yourself up. You’re not an idiot—you got conned by someone who knew exactly how to exploit trust. This happens to smart people every day, especially in dental practices.
Here’s what you need: a fractional CFO who specializes in dental practices and knows fraud inside out. Not your regular accountant—someone who’s seen this exact situation and knows how to fix it.
First thing they’ll tell you? No single person should control the whole money trail. The person writing checks shouldn’t also be the one balancing the bank account. That’s how she got you. Break that chain, and you break the opportunity for theft.
And while we’re at it, why are you still writing paper checks in 2025? Switch to digital payments with dual approval requirements. Makes it way harder for someone to move money without you knowing.
Look, I get that you can’t watch everything. That’s why you need someone to build you a system—automated alerts for large payments, weekly reports that make sense, quarterly reviews by someone who knows what shady looks like.
Have them do a forensic review first so you know exactly what happened and how much is actually gone. Then they’ll build you something custom based on your practice size. They’ll train your new hire on proper procedures and set up software that flags weird patterns.
🍃 Mindful Thoughts
The financial loss from embezzlement is a gut punch, but the betrayal cuts deeper. It’s easy to fall into a cycle of self-blame, replaying every moment you missed a red flag, every check you signed without a second thought. The first step in recovery is to give yourself grace. You weren’t foolish; you were targeted by someone who expertly manipulated the trust you extend to your team every day.
You cannot change what happened, but this event has given you something invaluable: clarity. You now see your business not just as a practice where you help people, but as a significant financial asset that requires and deserves protection. This is the moment you evolve from being a provider who owns a business to a CEO who runs one.
Your dad’s advice needs an update: stick to teeth, hire good people, AND verify everything. Trust, but make damn sure you’ve got systems that catch problems before they hit six figures.
And hey, good employees actually like working somewhere with proper systems. It means they won’t get blamed for someone else’s mess. Get yourself that fraud-savvy fractional CFO and get back to what you’re actually good at.
You didn’t cause this. But you get to control what happens next.
Lots of Love, Coffee and Chocolate,
Dangerously in Love with Finance and the HBoF Family
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