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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 4 Episode 2, featuring hosts Virgil, Cole, and Seth, with episode title text on a dark background.
PODCAST
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The new WCAG 2.2 rules you're already breaking (part 2)

SEASON
4
EPISODE
2
Virgil and Cole are joined again by High Monkey accessibility specialist Seth Moline to finish the list of what WCAG 2.2 added to 2.1. Part 2 covers Dragging Movements, Target Size, Accessible Authentication, and the three AAA criteria. Several of these change decisions that design and security teams already made, like how big a button is and whether a login form lets people paste a password.
October 20, 2026
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27:16
min
Photo of Seth Moline
Special Guest:
Seth Moline
Podcast thumbnail on a dark navy background. The title reads "The new WCAG 2.2 rules you're already breaking (part 1)," with "WCAG 2.2 RULES" set in a green highlight box. Below it, headshots of the three hosts, the one on the right wearing headphones.
PODCAST
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The new WCAG 2.2 rules you're already breaking (part 1)

SEASON
4
EPISODE
1
Virgil and Cole are joined by High Monkey accessibility specialist Seth Moline to walk through what WCAG 2.2 actually added to 2.1, one success criterion at a time. Part 1 covers Consistent Help, Redundant Entry, and Focus Not Obscured. None of it is new thinking. These are UX practices people ignored long enough that they ended up written into a standard.
October 6, 2026
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24:28
min
Photo of Seth Moline
Special Guest:
Seth Moline
Episode thumbnail for Discussing Stupid Season 4: The Teaser, with the episode title on a dark background.
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Season 4: The Teaser

SEASON
4
EPISODE
0
Season 4 is here. In Season 3, Virgil and Cole spent every episode on AI. They found that many of the problems people blame on AI are not caused by AI at all - those problems already existed, and AI just made them easier to see. This season, the show covers the full range of digital work again, including AI, accessibility, user experience, content, search, and design.
September 15, 2026
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5:11
min
Episode thumbnail for Discussing Stupid Season 3 Episode 18, Intentional AI series, featuring hosts Virgil and Cole, with episode title text on a dark background.
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Intentional AI

Intentional AI: Series takeaways - the real reason AI isn't working for you

SEASON
3
EPISODE
18
In the Season 3 finale, Virgil and Cole reflect on 18 episodes of AI testing and discussion & share what actually held up. The conversation centers on a real lesson: AI reflects what you bring to it. Strong process knowledge and domain expertise get results. Gaps and blind spots get amplified.
June 16, 2026
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29:53
min
Episode thumbnail for Discussing Stupid Season 3 Episode 17, Intentional AI series, featuring hosts Virgil and Cole, with episode title text on a dark background.
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Intentional AI

Intentional AI: How to get better results from AI prompts

SEASON
3
EPISODE
17
Virgil and Cole close out the heart of Season 3 by looking back at the prompts used across the Intentional AI series. The conversation gets at something most AI content skips: the quality of a prompt comes from the clarity of thought behind it, not the technique used to write it.
June 2, 2026
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22:55
min
Episode thumbnail for Discussing Stupid Season 3 Episode 16, Intentional AI series, featuring hosts Virgil and Cole, with episode title text on a dark background.
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Intentional AI

Intentional AI: The most important operation in analytics - understanding your "why?"

SEASON
3
EPISODE
16
AI should be a natural fit for analytics, but most people skip the step that makes it actually work. In this episode, Virgil and Cole dig into why knowing your "why" before you touch the data is the most important thing you can do - and what happens when you do not.
May 19, 2026
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23:07
min
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.
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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.
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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

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