The AI Riff (Ep17)

Episode 17 — AI’s Awkward Adolescence (with guest Ben Sizemore)

This week on The AI Riff, the crew gets a little bigger. Rob, Kyle, Mario, and Ruth welcome special guest Ben Sizemore, CIO of Land Gorilla, to dive into a theme every technologist knows too well: the messy teenage years of AI.

We kick things off with Taco Bell’s botched attempt at an AI drive-thru, where pranksters ordered 15,000 cups of water and chatbots got stuck in endless loops. Funny? Sure. But it’s also a case study in what happens when billion-dollar investments overlook edge cases, escalation paths, and real-world testing. From there, the team pulls on a bigger thread: why are companies racing to automate the lowest-wage tasks first, and what blind spots does that reveal about how AI is deployed?

The conversation stretches into the risky world of AI manipulation—how researchers “flatter” chatbots into breaking their own rules—and what that might mean if similar tricks creep into lending, underwriting, or compliance workflows. The crew wrestles with where human judgment must remain in the loop, and why combining deterministic rule sets with AI might be the safer path forward. Along the way, they swap tacos (vegan and otherwise), laugh about “meat robots,” and compare notes on what AI tools they actually used this week—from coding copilots to data-sorting assistants.

At its heart, this episode is about adolescence: that uneasy stage where a technology shows promise, but also immaturity, overreach, and insecurity. The payoff? A candid look at how companies can avoid Taco Bell-style faceplants and instead channel AI toward augmenting humans, not replacing them.