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 includes 36 Ways Your Bookkeeper Steals From You, How To Hire And Manage A Bookkeeper, and Blueprint for a Successful Pickpocket Bookkeeper, all available now.
Montgomery, who has spent 45 years consulting with small businesses, often found herself brought in after a company's books became too inaccurate or incomplete for a CPA to handle. Through that work, she repeatedly encountered trusted bookkeepers quietly draining cash from the businesses that depended on them, sometimes for years before anyone noticed. Her series directly addresses this pattern, offering owners both awareness and actionable steps.
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 for owners on vetting candidates, structuring interviews, writing job descriptions, and managing a bookkeeper once hired, aiming to prevent 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, illustrated with real case studies, including several drawn from IRS cases.
"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," Montgomery said. "This is an underreported crime that is very costly to businesses, and can be especially devastating to small businesses." Her 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.
The announcement matters because bookkeeper theft is a silent vulnerability for small and mid-sized enterprises, which often lack the financial controls of larger corporations. Montgomery's series provides a rare, insider's view of how these schemes operate and how they can be stopped, empowering owners to safeguard their cash flow and long-term viability. By combining real-world case studies with practical hiring and management advice, the books offer a comprehensive defense against a crime that many businesses do not even know to watch for. All three books are available for purchase on Amazon.
