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 an underreported threat: theft by their own bookkeeper. The series comprises 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 release matters because bookkeeper fraud is both costly and frequently overlooked, and Montgomery's decades of frontline experience give the books a practical, case-based foundation that owners can act on immediately.
Montgomery has spent 45 years consulting with small businesses, often called in after a company's books became too inaccurate or incomplete for a CPA to handle. In that work, she repeatedly encountered trusted bookkeepers quietly draining cash from the businesses that depended on them, sometimes for years before anyone noticed. Her first book, 36 Ways Your Bookkeeper Steals From You, lays out the specific methods she has uncovered firsthand, from skimming cash to manipulating company financial systems, and explains why this kind of theft so often goes undetected. The second, How To Hire And Manage A Bookkeeper, offers practical guidance on vetting candidates, structuring interviews, writing job descriptions, and managing a bookkeeper once hired, so the problem never starts. 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 with real case studies, including several drawn from IRS cases.
The implications for small and mid-sized businesses are significant. Bookkeeper theft can be especially devastating to smaller firms with limited cash reserves and thin oversight, and because the perpetrator is often a trusted insider with access to financial systems, the crime can persist for years. Montgomery's series addresses both prevention and detection, giving owners tools to screen hires, establish controls, and recognize red flags before losses mount. By framing the issue in plain language rather than academic theory, the books aim to make fraud awareness accessible to owners who may not have formal accounting training.
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. As Montgomery notes, theft by a bookkeeper is a tough subject to discuss, yet it is much more prevalent than most business owners realize or care to admit, and it is an underreported crime that is very costly to businesses and can be especially devastating to small businesses. The series arrives as a timely resource for owners seeking to close a gap in their financial oversight.
