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Discussing Stupid

@DiscussStupid

Discussing Stupid returns to the airwaves to transform digital facepalms into teachable moments—all in the time it takes to enjoy your coffee break!

 Minneapolis, MN
discussingstupid.com
Joined February 2018
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A party that wants every vote should have a website every voter can use. We reviewed the DNC, RNC and Green Party sites for accessibility. None came out clean.  highmonkey.com/episode/s4e3-…  #Accessibility #ElectionDay
Episode thumbnail for Discussing Stupid Season 4 Episode 3, featuring hosts Virgil and Cole, with episode title text on a dark background.

ALT Episode thumbnail for Discussing Stupid Season 4 Episode 3, featuring hosts Virgil and Cole, with episode title text on a dark background.

Blocking paste in a password field can fail WCAG 2.2. Part 2 covers that, plus dragging, target size, and the AAA criteria. Out now: highmonkey.com/podcast #WCAG22 #Accessibility
Episode thumbnail for Discussing Stupid Season 4 Episode 2, featuring hosts Virgil, Cole, and Seth, with episode title text on a dark background.

ALT Episode thumbnail for Discussing Stupid Season 4 Episode 2, featuring hosts Virgil, Cole, and Seth, with episode title text on a dark background.

Your site keeps the help link in the same place on every page. Then you hit checkout and it vanishes. WCAG 2.2 made that a Level A failure. Season 4 of Discussing Stupid starts here. Part 1 of 2. highmonkey.com/episode/s4e1-…
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.

ALT 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.

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Season 4 of Discussing Stupid starts 10/6 Last season: 18 episodes on AI. What we learned? Most AI problems aren't AI problems, they were already there. Season 4 zooms out. Accessibility, UX, design trends, content, search, all of it.. Teaser out now! highmonkey.com/episode/seaso…
Dark navy background with bold white "SEASON 4" and a teal rounded bar reading "THE TEASER". Small "Discussing STUPID" logo bottom-right.

ALT Dark navy background with bold white "SEASON 4" and a teal rounded bar reading "THE TEASER". Small "Discussing STUPID" logo bottom-right.

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AI is a mirror. Whatever you bring to it gets reflected back. That is the takeaway from 18 episodes of testing. Season 3 finale is out now. highmonkey.com/episode/s3e18…
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.

ALT 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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Most AI prompting advice is about how to write the prompt. Episode 17 of Discussing Stupid backs up a step and asks what actually makes prompts work in the first place. highmonkey.com/episode/s3e17…
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.

ALT 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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A dashboard nobody questions is just a very expensive way to feel informed. New episode on AI and analytics - and what has to change before the tools matter. highmonkey.com/episode/s3e16…
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.

ALT 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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Social media is oversaturated. No question about it. You can use AI to add to the noise, or you can use it to say something you actually believe. That choice happens before you ever open a tool. Newest episode of our Intentional AI series - out now. highmonkey.com/episode/inten…
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.

ALT 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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Agentic AI is everywhere. Most people using it cannot explain what it does. Today we dropped a new Discussing Stupid with Virgil, Cole, and Sean Wright from Kentico. highmonkey.com/episode/s3e14…
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.

ALT 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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Your AI search is only as good as your worst piece of content. Virgil, Cole, and Will Noble from Squiz on what conversational search actually requires. highmonkey.com/episode/s3e13…
Promotional graphic for Discussing Stupid Season 3, Episode 13.1, titled "Intentional AI: What the rise of conversational search means for your website." Features bold episode title text, an "Out Now" indicator, and the Discussing Stupid logo.

ALT Promotional graphic for Discussing Stupid Season 3, Episode 13.1, titled "Intentional AI: What the rise of conversational search means for your website." Features bold episode title text, an "Out Now" indicator, and the Discussing Stupid logo.

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The commercials make it sound simple. Just describe what you want, and boom... your app is built. But unless you handed AI a 20-page spec, you're probably not getting exactly what you pictured. #VibeCoding #AICode #DiscussingStupid #IntentionalAI #NoCode
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AI and coding. Finally, an episode where things mostly work. highmonkey.com/episode/s3e12…
Season 3, Episode 12 YouTube thumbnail, Virgil, Chad, and Cole's faces, and the text "Intentional AI: AI might struggle with creativity, but coding isn't creative" showing.

ALT Season 3, Episode 12 YouTube thumbnail, Virgil, Chad, and Cole's faces, and the text "Intentional AI: AI might struggle with creativity, but coding isn't creative" showing.

Discussing Stupid just crossed 1,000 listeners this season! Seven episodes still to come, including our first external guests. We're just getting started. highmonkey.com/blog/discussi…
Celebrating graphic for Discussing Stupid Season 3 reaching 1,000 listeners, featuring bold text and the Discussing Stupid logo.

ALT Celebrating graphic for Discussing Stupid Season 3 reaching 1,000 listeners, featuring bold text and the Discussing Stupid logo.

We tested 3 AI video tools with the same prompt. The results? Wildly different. New episode of Discussing Stupid is live now. highmonkey.com/episode/s3e11…
Promotional graphic for Discussing Stupid Season 3, Episode 11, titled "Intentional AI: AI video rewards planning, not your ideas." Features bold episode title text, an "Out Now" indicator, and the Discussing Stupid logo.

ALT Promotional graphic for Discussing Stupid Season 3, Episode 11, titled "Intentional AI: AI video rewards planning, not your ideas." Features bold episode title text, an "Out Now" indicator, and the Discussing Stupid logo.

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Discussing Stupid has a new home. After a few seasons on its own site, the podcast now lives on High Monkey’s website under the Podcast section. Same episodes. Same format. Same biweekly release schedule. Find everything here: highmonkey.com/podcast
Screenshot of the new Discussing Stupid section on the High Monkey website, with a backdrop graphic of dark clouds and lightning.

ALT Screenshot of the new Discussing Stupid section on the High Monkey website, with a backdrop graphic of dark clouds and lightning.

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AI showed up in 23% of this year’s Super Bowl ads. A lot of claims were made to say the least. This week on Discussing Stupid, we break down the gap between AI marketing and AI reality, and why automation can't & shouldn't replace thinking. Listen here: discussingstupid.com/episode…
Promotional graphic for Discussing Stupid Season 3, Episode 10, titled “Intentional AI: The Super Bowl didn't sell AI, it exposed it” Features bold episode title text, an “Out Now” indicator, and the Discussing Stupid logo.

ALT Promotional graphic for Discussing Stupid Season 3, Episode 10, titled “Intentional AI: The Super Bowl didn't sell AI, it exposed it” Features bold episode title text, an “Out Now” indicator, and the Discussing Stupid logo.

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AI images feel like a shortcut. They also come with ethical, legal, and trust risks most teams never plan for. S3E9 of Discussing Stupid breaks down where AI image generation works and where it fails. discussingstupid.com/episode…
Promotional graphic for Discussing Stupid Season 3, Episode 9, titled “Intentional AI: Just because AI can create images does not mean you should use them.” Features bold episode title text, an “Out Now” indicator, and the Discussing Stupid logo.

ALT Promotional graphic for Discussing Stupid Season 3, Episode 9, titled “Intentional AI: Just because AI can create images does not mean you should use them.” Features bold episode title text, an “Out Now” indicator, and the Discussing Stupid logo.

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AI can generate wireframes fast. That does not mean they are finished. In S3E8 of Discussing Stupid, we test AI wireframing tools and explain why human judgment matters more than the layout itself. discussingstupid.com/episode…
Promotional graphic for Discussing Stupid Season 3, Episode 8, titled “Intentional AI: The real value of AI wireframes is NOT the wireframes” Features bold episode title text, an “Out Now” indicator, and the Discussing Stupid logo.

ALT Promotional graphic for Discussing Stupid Season 3, Episode 8, titled “Intentional AI: The real value of AI wireframes is NOT the wireframes” Features bold episode title text, an “Out Now” indicator, and the Discussing Stupid logo.

AI promises easy personalization. In reality, it often makes things worse. S3E7 of Discussing Stupid breaks down role based vs behavioral personalization and tests how AI handles audience targeting. discussingstupid.com/episode…
Promotional graphic for Discussing Stupid Season 3, Episode 7, titled “Intentional AI: Why AI can make your content personalization worse.” Features bold episode title text, an “Out Now” indicator, and the Discussing Stupid logo.

ALT Promotional graphic for Discussing Stupid Season 3, Episode 7, titled “Intentional AI: Why AI can make your content personalization worse.” Features bold episode title text, an “Out Now” indicator, and the Discussing Stupid logo.

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I hope everyone is settling in nicely to 2026. As things start to pick back up, it feels like a good time to check in on how AI is actually showing up in practice.
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Links to Episodes 5 and 6: discussingstupid.com/episode… discussingstupid.com/episode…
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If you want to explore how these topics connect across the rest of the Intentional AI series, the full list of episodes is below. View the full series: discussingstupid.com/episode…
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