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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3
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Intentional AI: AI can't fix your social media if you have nothing to say
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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: AI can't fix your social media if you have nothing to say
SEASON
3
EPISODE
15
Social media is oversaturated and AI is making it worse. Most people using AI for social posts are skipping the hard part - knowing what they actually want to say. Cole and Virgil get into why that is the real problem, and what doing it better actually looks like.
May 5, 2026
26:09
min
PODCAST
|
Intentional AI
Intentional AI: AI agents are only as good as your workflow
SEASON
3
EPISODE
14
Agentic AI sounds autonomous, but it is only as good as what you put in front of it. Virgil and Cole bring in Sean Wright from Kentico to talk through what agents actually do in a content workflow, why context determines everything, and what evals have to do with keeping it all on track.
April 21, 2026
29:01
min
Special Guest:
Sean Wright
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
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