The Intersection of AI, People & Business Growth with Ryan Kononoff

On an Inner Circle call, host interviews Ryan Kononoff, CEO of Clearbridge Business Solutions, about building at the intersection of people, technology, and growth. Ryan shares his early start in IT, how Clearbridge was founded to bridge the gap between tech-focused and business-focused thinking, and why he leads with family-first priorities and a people-development mindset. Ryan explains Clearbridge’s work across IT, cybersecurity, automation, and process improvement, emphasizing solving business problems with clear ROI rather than “tech for tech’s sake.” The conversation covers why owners resist strategic tech, how AI should be introduced through experimentation and trust-building, common gaps between AI theory and deployment, security guardrails and policies, and practical first steps like getting a paid AI account, identifying internal AI champions, and using an AI readiness assessment. Want in on the live Q&A? Join our OBS Inner Circle — where entrepreneurs connect, learn, and get their biggest business questions answered live. Join Today — don’t just listen, get involved! www.optimizebusinesssystems.com 00:00 Welcome and Guest Intro 01:02 Ryan Origin Story 02:19 Why Clearbridge Exists 03:26 People First Leadership 06:34 Generalist Mindset and ROI 08:19 What Clearbridge Does Today 10:29 Why Owners Resist Tech 16:24 AI From Theory to Practice 20:04 Where to Start With AI 23:23 Job Fear and Change 28:39 AI Security and Policies 33:31 Monday Morning Action Plan 36:10 AI Tools Tier List 39:16 Connect With Ryan Closing