The Person Most Likely to Steal From Your Small Business Is Not Who You Think
The Story Of Ann
The following story is copied and pasted from a News 8 article:
DUNEDIN, Fla. (WFLA) — An employee at a Dunedin restaurant was arrested over the weekend after authorities said they learned she was canceling items on orders and pocketing the money.
According to an arrest affidavit, 44-year-old Ann Milewski had been carrying out her alleged scheme to defraud the Douglas Avenue business since 2021, resulting in nearly $57,000 in losses.
Officials said the restaurant’s owner recently noticed suspicious activity and, upon asking an accountant to investigate, found that Milewski had several thousands of dollars in canceled transactions.
The amount missing was significantly more than that of other employees at Home Plate on the Trail, the affidavit said.
Over the next three days, managers said they observed Milewski as she canceled items on cash orders and took the money from the register.
When confronted about the suspicious activity, authorities said Milewski claimed she “didn’t know how to explain the discrepancy” and eventually requested a lawyer.
Milewski was taken into custody shortly after she pulled up to work in her car on Saturday, Nov. 16. During her arrest, deputies said they found Adderall inside an envelope she was carrying.
She was charged with a scheme to defraud $50,000 or more, grand theft, possession of a controlled substance, and no valid driver’s license.
TLDR: Over the span of three years, a waitress named Ann stole almost $60k from the diner where she worked. She took advantage of the point-of-sale system by voiding items after cash payments were made, making it seem like orders were cancelled while she secretly kept the money.
Who Is Most Likely To Steal Money From Your Small Business?
It’s not the young hackers sitting at their computers or the scamming center set up somewhere in India.
Embezzlement happens wherever there is trust built.
“Ann” is likely someone who:
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you like or enjoy as a person
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you trust enough to give access to your financial data, whether you know it or not
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has no previous criminal history (as many embezzlers are terminated and not prosecuted when caught)
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is facing a (often financial, but not always) pressure
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is able to rationalize their own fraudulent behavior (“I needed to protect my family.”)
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is good at spotting holes in systems, where internal controls are weak or nonexistent
“Oh but Ann… there’s no way! She’s a PTA mom who goes to church every week!”
Yep. “Ann” could easily be your own brother or sister.
In fact, anybody could be “Ann”, even those of us who consider ourselves “morally on the straight and narrow.”
It can be a bit scary to think that “Ann” can look like anyone out there, including our own family members or people we would never, ever suspect.
How How To Minimize Your Chances Of Working With “Ann”
So if anybody around us could potentially steal from us, how do we protect ourselves beforehand?
1) Understand why the people we trust steal
Technology and ways to defraud constantly evolve, but human behavior stays pretty constant.
We already know that:
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“Ann” likely faces some perceived sense of PRESSURE.
Ex: she needs bail money for her son’s bond.
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“Ann” likely feels that her stealing is JUSTIFIED.
Ex: she feels underpaid, under-appreciated, or treated unfairly.
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“Ann” has the OPPORTUNITY to steal.
Ex: she is your longtime assistant who has access to your financial information, and there are few safeguards in place.
Maybe the theft starts with small withdrawals here and there, which then spirals into larger and larger amounts.
For many people, when PRESSURE + JUSTIFICATION + OPPORTUNITY are presented, their survival instincts kick in and override their relational focus. Even the most trusted people can make decisions they thought they’d never make when their survival (usually money) is threatened.
Assume that everyone is capable under the right conditions.
2) Tighten control around access to your information.
Before you start working with someone, make sure that you tighten control around all of your information, which includes finances.
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Regularly monitor transactions and do regular audits. Avoid giving one person full control over money or any accounts.
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Think about what personal information you’re willing to share and which boundaries are non-negotiable.
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When someone leaves or changes roles, immediately remove their access.
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How protected or secure are your passwords, accounts, etc.?
Find as many ways as you can to safeguard your information, especially when it is tied to finances.
3) Document everything from the start.
We recommend that you always document your communication.
This includes writing (contracts, agreements, customer support emails, invoices, internal messages, etc.) or recordings(security cameras, time-tracking, logs, etc.).
You never know when you might need evidence down the line.
4) Assess whether you are a good fit for each other on a deeper level.
You can use this checklist for business partnerships, which can apply to any working relationship.
Accepting only connections based on deeper core compatibility helps to minimize the chances of surprise sabotage later on.
Misalignment creates friction, resentment, and power struggles over time.
5) Clean up your “spread.”
Keep your business as simple and organized as possible before collaborating with others. When your business is messy, it’s easier for things to slip through the cracks. Too many apps, accounts, folders, and systems are hard to keep track of.
You can see who’s doing what, where money is moving, and when something doesn’t look right.
Use a password manager. Categorize things together if you can.
A simple setup protects you. When everything is easy to see, it’s much harder for mistakes or corruption to hide.
At the end of the day, “Ann” can come into our business in any number of ways. This is your first line of defense.
For more information on this topic, you can read Kelly Paxton’s book on pink collar crime.