Business consultant and full-charge bookkeeper Charlie Montgomery has released a three-book series aimed at helping small and mid-sized business owners guard against a threat she says is far more common than most owners realize: 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 the crime Montgomery describes is both costly and hard to spot. Drawing on 45 years of consulting with small businesses, she says she was frequently brought in only after a company’s books had become too inaccurate or incomplete for a CPA to handle. In the course of that work, she kept encountering the same pattern: 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 the specific methods Montgomery has uncovered firsthand, from skimming cash to manipulating company financial systems, and explains why such theft so often goes undetected. How To Hire And Manage A Bookkeeper follows with practical guidance on vetting candidates, structuring interviews, writing job descriptions and managing a bookkeeper once hired, with the goal of preventing the problem before it 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. That volume is illustrated with real case studies, including several drawn from IRS cases.
Montgomery said the subject is difficult but necessary. “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 stakes are particularly high for smaller firms, where a single trusted employee often controls payments, records and reconciliations with little oversight, leaving limited reserves to absorb losses that may compound over months or years.
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, according to the release, shapes all three books into plain-spoken guides rather than academic texts, a format intended to make the material usable for owners without accounting backgrounds.
All three books are available now for purchase on Amazon.
