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The Discussing
Stupid Podcast

Transforming digital facepalms into teachable moments - all in the time it takes to enjoy a cofee break!

Episodes

Episode thumbnail for Discussing Stupid Season 3 Episode 15, Intentional AI series, featuring hosts Virgil and Cole, with episode title text on a dark background.
PODCAST
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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
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26:09
min
Episode thumbnail for Discussing Stupid Season 3 Episode 14, Intentional AI series, featuring hosts Virgil Carroll and Cole Schlotthauer with guest Sean Wright from Kentico, with episode title text on a dark background.
PODCAST
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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
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29:01
min
Image of Sean Wright
Special Guest:
Sean Wright
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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
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27:03
min
Image of Will Noble
Special Guest:
Will Noble
Season 3, Episode 12 image, Virgil, Chad, and Cole's faces, and the text "Intentional AI: AI might struggle with creativity, but coding isn't creative" showing.
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
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25:52
min
Photo of Chad Heinle
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
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22:42
min
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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
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20:24
min
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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
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29:22
min
PODCAST
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Intentional AI

Intentional AI: The real value of AI wireframes is NOT the wireframes

SEASON
3
EPISODE
8
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
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28:31
min
Photo of Chad Heinle
Special Guest:
Chad Heinle
PODCAST
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Intentional AI

Intentional AI: Why AI can make your content personalization worse

SEASON
3
EPISODE
7
Content personalization sounds simple, but using AI for it often makes things worse. In this episode, the team breaks down role based and behavioral personalization, tests three AI tools, and explains why unclear goals and assumptions lead to generic or uncomfortable results.
January 13, 2026
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25:34
min
PODCAST
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Intentional AI

Intentional AI: You’re asking AI to solve the wrong problems for SEO/GEO/AEO

SEASON
3
EPISODE
6
SEO, GEO, and AEO are often treated as optimization problems. In this episode, we explain why that mindset often fails, how AI exposes weak structure and unclear intent, and what actually drives search visibility today.
December 16, 2025
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25:58
min
Photo of Seth Moline
Special Guest:
Seth Moline

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