My Coach in a Box: Turning 30 Years of Coaching into an AI Expert — Douglas Pudney

In this episode of Founders, Future, with host Zach Young, Zach sits down with Douglas Pudney, founder of My Coach in a Box, to unpack three decades of hands-on business coaching and the new AI-powered strategic operating system Douglas is bringing to SME owners. Douglas traces his journey from early consulting and advisory work through Outcomes Business Group and Capital Bridge Studios, and explains how decades of proven frameworks inspired an “expert model” that packages elite coaching into an always-available assistant for clarity, rhythm, execution and exit readiness.The conversation dives into the product: My Coach in a Box (launching Q1 2026), the Freedom Bridge framework and the Freedom Index that measures business health, and “Clara Clarity” — the expert persona built from top strategic thinkers and hundreds of advisor inputs. Douglas explains how the system blends proprietary frameworks with large language model support to deliver DIY and DFY options, white-label possibilities for advisors, and a partnership-led go-to-market focused on advisory and PE ecosystems. Listeners will come away with practical ideas about turning strategy into repeatable rhythm, building optionality for exits, and how AI can amplify — not replace — human expertise.🌐 Connect with Douglas Pudney LinkedIn: https://www.linkedin.com/in/dougpudney