PODCAST
The Discussing
Stupid Podcast
Transforming digital facepalms into teachable moments - all in the time it takes to enjoy a cofee break!
About the podcast
Discussing Stupid is hosted by Virgil Carroll, High Monkey’s CEO and Principal Human Solutions Architect, and Cole Schlotthauer, High Monkey’s Content Strategy Specialist. We work with teams every day on digital strategy, content, and platform decisions, so we see firsthand where projects stall, overcomplicate, or miss the point entirely.
This podcast is a space we've created to address these problems directly (AKA rant). Each episode focuses on one practical topic in modern digital work, from AI to collaboration to content practices. We break down what is actually happening, why it goes wrong, and most importantly, what to do instead. The goal is simple: clearer direction, practical solutions, and a better path forward for teams who want to get it right.
This podcast is a space we've created to address these problems directly (AKA rant). Each episode focuses on one practical topic in modern digital work, from AI to collaboration to content practices. We break down what is actually happening, why it goes wrong, and most importantly, what to do instead. The goal is simple: clearer direction, practical solutions, and a better path forward for teams who want to get it right.

Latest Episodes
PODCAST
|
Intentional AI
Intentional AI: AI video rewards planning, not your ideas
SEASON
3
EPISODE
11
AI video tools can generate promotional clips in seconds, but the gap between what comes back and what is actually usable is wider than most teams expect. In this episode, Virgil and Cole test three AI video tools using the same prompt and break down why planning, storyboarding, and clear objectives matter far more than the tool you choose.
March 10, 2026
22:42
min
PODCAST
|
Intentional AI
Intentional AI: The Super Bowl didn't sell AI, it exposed it
SEASON
3
EPISODE
10
AI dominated a noticeable share of this year’s Super Bowl ads, but what was actually being sold? In this episode, we break down the hype, the promises of effortless automation, and the gap between AI marketing and real world implementation. If you are trying to separate AI strategy from expensive noise, this conversation is for you.
February 24, 2026
20:24
min
PODCAST
|
Intentional AI
Intentional AI: Just because AI can create images doesn't mean you should use them
SEASON
3
EPISODE
9
AI can generate images and graphics in seconds, but visuals introduce ethical, legal, and trust risks most teams are not prepared for. In this episode, the team tests AI image generation tools, examines where they help and where they fail, and explains why judgment matters more than speed when AI starts producing visuals.
February 10, 2026
29:22
min
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