PODCAST
The Discussing
Stupid Podcast
Transforming digital facepalms into teachable moments - all in the time it takes to enjoy a cofee break!
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Intentional AI: What the rise of conversational search means for your website
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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: What the rise of conversational search means for your website
SEASON
3
EPISODE
13
When you put an LLM on top of years of unmanaged content, the AI does not skip the bad parts. Virgil and Cole bring in Will Noble from Squiz to talk through what conversational search actually requires - and why your content foundation matters more than your technology choices.
April 7, 2026
27:03
min
Special Guest:
Will Noble
PODCAST
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Intentional AI
Intentional AI: AI might struggle with creativity, but coding isn't creative
SEASON
3
EPISODE
12
Coding runs on patterns and repetition, which makes it one of the better fits for AI... at least in theory. In this episode, Virgil, Cole, and returning guest Chad put Claude, ChatGPT, and GenSpark to the test building an accessible web component, and unpack what AI can and can't do depending on who's behind the keyboard.
March 24, 2026
25:52
min
Special Guest:
Chad Heinle
PODCAST
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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
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