Debbie Rosler – CEO Embezzled $1.5M From His Own Startup
In this episode, James Kennedy sits down with Debbie Rosler, fractional CFO at Burkland, to dig into the uncomfortable but critical topic of waste, fraud and abuse inside venture-backed startups. Drawing on a career that spans investment banking, private equity, Levi Strauss, dot-com startups and a career-defining embezzlement case where a CEO “borrowed” $1.5M from his own company, Debbie walks through exactly how it happened, why the board didn’t catch it, and the practical controls that saved the business. They also explore how SaaS founders can use “two sets of eyes,” approval matrices and even purchase orders with lawyers and contractors – and why phishing, payment-redirection scams and AI deepfakes make 2025 a dangerous time to be casual about controls. James closes by introducing redflag.procurementexpress.com, a 30-second AI QuickBooks scan that flags unusual spending patterns before they blow up into a crisis.
