Business consultant and full-charge bookkeeper Charlie Montgomery has released a three-book series aimed at protecting small and mid-sized business owners from what the announcement describes as one of the most underreported threats to their companies: 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 significance of the release lies in the gap it addresses. Montgomery has spent 45 years consulting with small businesses, frequently brought in after a company's books became too inaccurate or incomplete for a CPA to handle. Across 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. The announcement frames this as an underreported crime that is very costly to businesses and can be especially devastating to small businesses, where a single trusted employee often controls payments, records and reconciliations with little oversight.
The structure of the series moves from diagnosis to prevention to response. 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 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 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 with real case studies, including several drawn from IRS cases.
For owners, the implications extend beyond awareness. The announcement suggests that the vulnerability is often structural rather than simply a matter of bad luck: hiring practices, job descriptions and day-to-day management of the bookkeeping function all shape whether theft becomes possible, and the books are positioned as plain-spoken guides rather than academic texts. Montgomery's background supports that framing. 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.
Montgomery said the subject is a difficult one for owners to confront. "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." The release of the three books gives owners a structured way to examine their own operations, from the hiring interview to the moment a discrepancy first appears in the books, and to recognize warning signs before losses compound.
