From Door-to-Door Bookkeeping to a 1,000-Client Cloud Firm w/ Nick Pasquarosa

In this episode, Rory speaks with Nick Pasquarosa, Founder and CEO of Bookkeeper360, about building a modern accounting firm from the ground up and why innovation starts with listening to small business owners. Nick shares how a door-to-door side hustle in high school evolved into a nationwide cloud accounting firm serving nearly 1,000 clients with a fully remote team across 26 states. He explains how his role shifted from boots-on-the-ground bookkeeper to strategic CEO, and why leadership communities like EO, YPO, and Hampton helped accelerate that growth. The conversation dives into the firm’s technology roadmap, including the development of its proprietary AI tool BOLT, designed to deliver CFO-level insights at scale while preserving the human relationship. Nick also unpacks how AI is being used internally to surface advisory insights, streamline month-end analysis, and reduce burnout without sacrificing value. Want to know how firms can leverage technology without losing their human edge? Curious how AI can enhance advisory conversations rather than replace them? Find out the answers to these questions and more in this forward-looking conversation with Bookkeeper360's CEO Nick Pasquarosa.