Business consultant and full-charge bookkeeper Charlie Montgomery has released a three-book series aimed at helping small and mid-sized business owners protect themselves from what she describes as one of the most underreported threats to their companies: theft by their own bookkeeper. The series includes 36 Ways Your Bookkeeper Steals From You, How To Hire And Manage A Bookkeeper, and Blueprint for a Successful Pickpocket Bookkeeper, all available now.
The announcement matters because the risk it addresses is easy to overlook. Montgomery has spent 45 years consulting with small businesses, often brought in after a company's books became too inaccurate or incomplete for a CPA to handle. Over the course of that work, she kept encountering the same problem: trusted bookkeepers quietly draining cash from the businesses that depended on them, sometimes for years before anyone noticed. For owners who delegate financial recordkeeping to a single trusted employee, the series reframes that delegation as a risk that requires structure, oversight, and specific safeguards.
The first book, 36 Ways Your Bookkeeper Steals From You, lays out the specific methods Montgomery has uncovered firsthand, from skimming cash to manipulating company financial systems, and explains why this kind of theft so often goes undetected. How To Hire And Manage A Bookkeeper follows with practical guidance for owners on vetting candidates, structuring interviews, writing job descriptions, and managing a bookkeeper once they are hired, so the problem never starts in the first place. The series closes with Blueprint for a Successful Pickpocket Bookkeeper, which breaks down how theft schemes are typically set up and escalated, the warning signs owners should watch for, and what to do once theft is suspected or confirmed, illustrated throughout with real case studies, including several drawn from IRS cases.
In a statement accompanying the release, Montgomery said the topic is difficult but widespread. "Theft by a bookkeeper is a really tough subject to discuss, yet it's much more prevalent than most business owners realize or care to admit," she said. "This is an underreported crime that is very costly to businesses, and can be especially devastating to small businesses."
Montgomery's background extends beyond bookkeeping. She has consulted with more than 100 clients across industries including real estate, construction, retail, and manufacturing, managed large residential and warehouse operations, and helped small business owners navigate PPP loan compliance during the pandemic. That experience shapes all three books into plain-spoken guides rather than academic texts, a format that may make the material more accessible to owners without formal accounting training.
The practical implications reach beyond individual companies. Small businesses often operate with thin margins and limited staff, leaving little room to absorb losses that go unnoticed for extended periods. By documenting both the methods used in bookkeeper theft and the hiring and management practices that can prevent it, the series gives owners a framework for tightening internal controls before losses occur, and a reference for responding if they already suspect them. All three books are available now for purchase on Amazon.
