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 often-overlooked 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 announcement matters because bookkeeper theft is a silent drain on businesses, often going unnoticed for years. Montgomery, who has spent 45 years consulting with small businesses, frequently encountered situations where trusted bookkeepers quietly siphoned cash from the companies that depended on them. Her first book, 36 Ways Your Bookkeeper Steals From You, details the specific methods she has uncovered firsthand, from skimming cash to manipulating financial systems, and explains why such theft so often evades detection.
The second book, How To Hire And Manage A Bookkeeper, shifts to prevention, offering practical guidance on vetting candidates, structuring interviews, writing job descriptions, and managing a bookkeeper after hiring. This proactive approach is critical, as Montgomery notes that the crime is "much more prevalent than most business owners realize or care to admit." The final book, Blueprint for a Successful Pickpocket Bookkeeper, breaks down how theft schemes are set up and escalated, the warning signs owners should watch for, and what to do once theft is suspected or confirmed. It includes real case studies, several drawn from IRS cases, adding weight to the warnings.
Montgomery's extensive background lends credibility to the series. 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. This experience shapes the books into plain-spoken guides rather than academic texts, making them accessible to busy owners who may not have financial expertise.
The implications of this release are significant for small and mid-sized enterprises, which are often most vulnerable to bookkeeper theft due to limited resources and oversight. By exposing the methods and warning signs, Montgomery provides owners with tools to safeguard their assets and avoid devastating losses. The series also addresses a taboo subject, encouraging business owners to confront a risk that many would rather ignore. As Montgomery states, "This is an underreported crime that is very costly to businesses, and can be especially devastating to small businesses." With these books, she aims to change that narrative, equipping owners to detect and deter theft before it cripples their operations.
