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September 3, 2025 63 mins

Is AI the biggest opportunity or the biggest threat to your business? In this episode of The Overlap Podcast, Sid and Keith sit down with AI strategist and entrepreneur Kai Gray to unpack what AI really means for small business owners. From large language models to practical, agent-based tools, Kai explains how to start using AI today, what to watch out for, and how to avoid being left behind as the technology accelerates.

What You’ll Learn

  • The difference between large language models and agent-based AI

  • How to train AI with projects so it learns your business

  • The secret to writing prompts that actually deliver useful results

  • Why starting small is the best way to build confidence with AI

  • Real-world examples of AI saving time and cutting costs for small business

Key Topics Discussed

  • Why today is the “worst AI will ever be”—and what that means for you

  • How agents are quietly transforming customer service, reporting, and operations

  • The role of privacy and trust when integrating AI into business systems

  • Why choosing one AI tool at first can save you frustration

  • How adopting an “AI-first” mindset gives small businesses an edge

Sponsor Spotlight

  • C2 Wealth Strategies – Personalized financial solutions to help you create wealth and achieve freedom. https://c2wealth.com

  • Roadmap for Growth – An online course from Chris Francis and Rick Miller to help small service businesses scale, build teams, and create systems that last. https://treebusiness.com

  • Content Fresh – Driving a 2,235% increase in reach for The Overlap Podcast with expert social media management. https://contentfresh.com/overlap/

  • Barranco and Associates – Trusted accounting and financial consulting from Johnny Barranco and his team, aligning your finances with long-term goals. https://barrancocpas.com

Quote Worth Remembering

“Never before have you had this kind of PhD-level expert sitting on your shoulder in every domain—for $20 a month.” – Kai Gray

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