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, which includes 36 Ways Your Bookkeeper Steals From You, How To Hire And Manage A Bookkeeper, and Blueprint for a Successful Pickpocket Bookkeeper, is all available now.
The announcement matters because bookkeeper theft is a underreported crime that can be especially devastating for small businesses, where owners often trust a single individual with financial oversight. Montgomery draws on 45 years of consulting experience, during which she was frequently brought 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.
The first book, 36 Ways Your Bookkeeper Steals From You, lays out specific methods Montgomery has uncovered firsthand, from skimming cash to manipulating company financial systems, and explains why such 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 after hiring, 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.
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, making the information accessible to owners who may not have financial expertise.
For business owners, the implications are significant. The series provides concrete tools to identify vulnerabilities, implement preventive measures, and respond effectively if theft occurs. By shedding light on this hidden threat, Montgomery aims to reduce the costly impact of bookkeeper fraud on small and mid-sized enterprises.
