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: 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
10
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
PODCAST
|
Intentional AI
Intentional AI: The real value of AI wireframes is NOT the wireframes
SEASON
3
EPISODE
10
AI can generate wireframes and page layouts in minutes, but speed changes the risk profile of design work. In this episode, the team tests AI wireframing tools, breaks down where they help and where they fail, and explains why human judgment matters more than the wireframes themselves.
January 28, 2026
28:31
min

Special Guest:
Chad Heinle
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