In this episode of Behind the Story, host Jelani sits down with Todd Merrill—fractional CTO, software executive, private pilot, and host of Tales from The Sky Lounge—for a practical conversation on what AI is actually changing in business and software.

Todd breaks down why we’re entering an era where coding as a moat is fading, how AI coding tools are getting “shockingly good,” and why the real differentiator is context engineering: clearly defining the user, problem, constraints, and outcomes before letting AI generate anything.

We also unpack key shifts shaping the AI wave—Model Context Protocol (MCP), tool-using assistants that connect to email/calendar/CRM, and what that means for non-technical founders, startups, and established companies trying to move fast without breaking trust.

What you’ll learn

• Why AI lowers the cost of building software—and unlocks more ideas from non-technical founders
• How to avoid “vibe coding” and build like a CTO: planning → artifacts → context → execution
• The leadership gap Todd sees: curiosity at the top vs. adoption friction across teams
• Trust, safety, fraud, and the human risks we’re not confronting enough yet
• Todd’s personal grounding practices—and why “touching grass” matters more than ever