
Discussing Stupid: A byte-sized podcast on stupid UX
High Monkey
Discussing Stupid returns to the airwaves to transform digital facepalms into teachable moments—all in the time it takes to enjoy your coffee break! Sponsored by High Monkey, this podcast dives into ‘stupid’ practices across websites and Microsoft collaboration tools, among other digital realms. Our "byte-sized" bi-weekly episodes are packed with expert insights and a healthy dose of humor. Discussions focus on five key areas: Business Process & Collaboration, UX/IA, Inclusive Design, Content & Search, and Performance & SEO. Join us and let’s start making the digital world a bit less stupid, one episode at a time.
Visit our website at https://www.discussingstupid.com
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Why search systems fail without semantics
Discussing Stupid: A byte-sized podcast on stupid UX
12/03/24 • 13 min
In Episode 4 of Discussing Stupid, host Virgil Carroll and co-host Cole Schlotthauer from High Monkey dive into the complex world of search systems and the importance of semantics in delivering relevant results. This episode explores the frustrations users often face when search systems fail to recognize variations in spelling, synonyms, and context, which can drastically impact user experience.
Virgil and Cole discuss common issues with search systems, such as treating every search term the same and ignoring common phrases and alternative names. They share real-world examples, like a bank where users searched for one name in numerous ways, illustrating the need for search systems to recognize and account for these variations. The team also emphasizes that improving search functionality requires more than just turning it on—it involves continuous work, testing, and understanding of user behavior.
To wrap up, Virgil highlights best practices, including using “push search” technology to guide users to the right results and leveraging search analytics to understand how people are searching. By the end of the episode, listeners will gain practical insights into making search more intuitive and user-friendly.
Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.
(0:00) - Intro
(1:26) - A lot of search systems suck
(1:57) - Search needs semantics
(3:04) - Search with VS without semantics
(4:48) - When AB&T meets AB and T
(6:14) - The English language is funny
(8:00) - The power of curated results
(10:50) - Virgil's biggest piece of advice
(12:41) - Outro
Subscribe for email updates on our website:
https://www.discussingstupid.com/
Watch us on YouTube:
https://www.youtube.com/@discussingstupid
Listen on Apple Podcasts, Spotify, or Soundcloud:
https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0
https://soundcloud.com/discussing-stupid
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Font mistakes that are costing you big time
Discussing Stupid: A byte-sized podcast on stupid UX
12/17/24 • 15 min
In Episode 5 of Discussing Stupid, host Virgil Carroll and co-hosts Chad Heinle and Cole Schlotthauer from High Monkey explore the often-overlooked mistakes organizations make with typography and the significant impact it can have on user experience and performance. From excessive font usage to unreadable design choices, this episode dives into the dos and don’ts of effective typography.
The team discusses:
- Why using too many fonts on a website creates confusion and slows down performance.
- The importance of keeping fonts readable and how font size and weight affect usability.
- Real-world examples of font mistakes, including when and where decorative fonts can work—and when they don’t.
- How poor typography choices can kill website performance, particularly through improper font loading.
To wrap up, they discuss actionable best practices, including limiting font selections, optimizing font files for performance, and always keeping your audience in mind when choosing typography.
By the end of this episode, you’ll gain practical insights to help your website achieve both aesthetic appeal and functional clarity—without sacrificing performance.
This marks the final episode of 2024, and we want to thank all of you for joining us this year! We’ll be taking a short break for the holidays but will return in 2025 with more episodes, more “stupid,” and more expert advice to help you avoid common digital mistakes.
Until then, like, review, and subscribe on your favorite podcast platform, and visit www.discussingstupid.com for updates and resources.
Happy holidays, and see you in the new year!
(0:00) - Intro & holiday spirit
(1:44) - Welcome back, Chad
(2:20) - Too many fonts = chaos
(4:05) - Learning from print design
(5:25) - Typography as Art vs. Function
(6:23) - The hidden cost of fancy fonts
(8:04) - Should some fonts be banned?
(10:11) - Know your audience and the context
(12:06) - With fonts, less is more
(14:28) - Outro & happy holidays!
Subscribe for email updates on our website:
https://www.discussingstupid.com/
Watch us on YouTube:
https://www.youtube.com/@discussingstupid
Listen on Apple Podcasts, Spotify, or Soundcloud:
https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0
https://soundcloud.com/discussing-stupid
Check us out on socials:
https://www.linkedin.com/company/discussing-stupid
https://www.instagram.com/discussingstupid/

Finding the metadata "Goldilocks zone"
Discussing Stupid: A byte-sized podcast on stupid UX
04/01/25 • 18 min
In Episode 12, host Virgil Carroll is joined by co-host Cole from High Monkey to dig into a deceptively tricky topic: metadata—what it is, how it works, and why getting it right is more about balance than perfection.
Metadata plays a huge role in findability, search accuracy, and content structure. But when it comes to tagging your content, more isn’t always better—and less definitely isn’t enough. That’s where the concept of the “metadata Goldilocks zone” comes in.
They unpack the most common metadata mistakes and what to do instead, including:
✅ Why under-tagging leaves your site relying on search engine guesswork
✅ How over-tagging renders metadata meaningless
✅ What makes a tag actually useful (and when it’s just noise)
✅ How to approach metadata as an evolving strategy—not a one-time fix
Virgil shares hard-won lessons from consulting across industries, explaining why metadata success depends on both the structure and the context of your content. From internal file systems to public websites, they explore how to build better tagging frameworks without falling into analysis paralysis.
To wrap things up, they offer a practical rule of thumb for anyone managing metadata: optimize for the 80% of user needs first—and let real usage data guide the rest.
For more conversations about digital strategy, search, UX, and all the ways we get it wrong (and how to get it right), visit www.discussingstupid.com and subscribe on your favorite podcast platform.
(0:00) - Intro
(2:27) - What even is metadata?
(4:10) - Metadata is not one-size-fits-all
(7:20) - The dangers of under tagging
(10:00) - The dangers of over tagging
(12:43) - Finding the “Goldilocks” zone with metadata
(15:30) - Virgil’s verdict: Follow the 80/20 rule
Subscribe for email updates on our website:
https://www.discussingstupid.com/
Watch us on YouTube:
https://www.youtube.com/@discussingstupid
Listen on Apple Podcasts, Spotify, or Soundcloud:
https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0
https://soundcloud.com/discussing-stupid
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The hype and sensibility of Artificial Intelligence in Search | Ben Tilley, Funnelback
Discussing Stupid: A byte-sized podcast on stupid UX
04/11/18 • 34 min
On our very first podcast (episode 1 YEAH!!!), Virgil is joined by Ben Tilley from Funnelback, an Australian-based search company, to break through all the hype around the use of artificial intelligence in search and talk about real world implementations and pitfalls.
Listening to this discussion, you will discover that implementing AI in search is not all that easy (shocker!!) and still requires you to follow good content and search practices. Where AI has many practical applications in search, effort is still needed and fundamentals need to be followed. In the end, AI cannot fix your search if your content still sucks.
There is reason to hope, good AI can be very helpful. According to Ben, "Being able to use some form of natural language processing to extract information out of your written text and turn that back into structure is a great way you can start to improve search."
Throughout this episode, Virgil and Ben will share the challenges you will face while giving you thoughts on how you can get your content and search ready to be able to use AI to its full potential.
Resources discussed:
- https://www.wolframalpha.com/ - one of the first search engines to use AI
- https://www.westpac.com.au/ - example organization using AI in their search
Helpful articles from Funnelback:
- https://www.funnelback.com/blog/artificial-intelligence-why-the-farmer-killed-the-fox
- https://www.funnelback.com/blog/intelligent-question-answering
- https://www.funnelback.com/blog/is-the-future-of-search-proactive
Subscribe for email updates on our website:
https://www.discussingstupid.com/
Watch us on YouTube:
https://www.youtube.com/@discussingstupid
Listen on Apple Podcasts, Spotify, or Soundcloud:
https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0
https://soundcloud.com/discussing-stupid
Check us out on socials:
https://www.linkedin.com/company/discussing-stupid
https://www.instagram.com/discussingstupid/

Big images, slow loading
Discussing Stupid: A byte-sized podcast on stupid UX
10/29/24 • 16 min
In Episode 2 of Discussing Stupid Season 2, host Virgil Carroll, along with Chad and Cole from High Monkey, dives into the topic of page performance and SEO, specifically focusing on how oversized images can slow down your website.
They discuss common mistakes people make with large images—like shrinking images in HTML without optimizing file size—and how these errors can negatively impact both the user experience and SEO rankings. The team shares insights into how to avoid these pitfalls and explores how tools like RIOT (Radical Image Optimization Tool) can help reduce file sizes without sacrificing image quality.
You'll also hear about the often overlooked balance between mobile and desktop optimization. The team highlights why simply resizing images for mobile isn’t enough and explains how poor image handling can lead to sluggish performance on mobile devices, frustrating users and hurting your site's overall effectiveness.
By the end of this episode, you'll walk away with actionable tips on optimizing images for both performance and SEO, ultimately improving your site’s speed and user experience.
Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.
LINKS
Tools mentioned:
Riot (Radical Image Optimization Tool): https://riot-optimizer.com/
Riot demo clip from this episode: https://www.discussingstupid.com/p/episode-2-image-optimization-demo
Subscribe for email updates on our website:
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Watch us on YouTube:
https://www.youtube.com/@discussingstupid
Listen on Apple Podcasts, Spotify, or Soundcloud:
https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0
https://soundcloud.com/discussing-stupid
Check us out on socials:
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https://www.instagram.com/discussingstupid/

Are websites evolving or devolving?
Discussing Stupid: A byte-sized podcast on stupid UX
01/07/25 • 14 min
In Episode 6 of Discussing Stupid, host Virgil Carroll and co-host Cole Schlotthauer from High Monkey reflect on the evolution of web design and discuss how websites have grown increasingly complex over the years. This episode delves into the challenges of balancing form and function in web design, examining how trends have influenced modern websites—often at the expense of user experience.
Virgil and Cole explore the history of web design, from the simplicity of early 2000s websites to the rise of stylistic trends like Flash, hero images, and parallax scrolling. They discuss how the pursuit of flashy, modern designs can overshadow usability, creating obstacles for users trying to complete tasks. Drawing on decades of experience, Virgil shares insights into the “form vs. function” debate, emphasizing that good design prioritizes purpose and user needs.
To wrap up, the duo highlights the growing trend toward simplicity in web design and the importance of finding a balance between aesthetics and practicality. Listeners will leave with a deeper understanding of how to create websites that are both visually engaging and user-friendly.
Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.
(0:00) - Intro
(1:26) - Websites have gotten too complicated
(3:13) - Evolution of web design trends
(4:43) - Form vs Function: An age old battle
(6:59) - When did style over substance get big?
(8:53) - The pressure to keep up with trends
(10:15) - It's about balancing form and function
(13:55) - Outro
Subscribe for email updates on our website:
https://www.discussingstupid.com/
Watch us on YouTube:
https://www.youtube.com/@discussingstupid
Listen on Apple Podcasts, Spotify, or Soundcloud:
https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0
https://soundcloud.com/discussing-stupid
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Your poorly written alt text doesn't go unnoticed...
Discussing Stupid: A byte-sized podcast on stupid UX
10/15/24 • 16 min
Welcome to the first episode of Discussing Stupid Season 2, where your host Virgil Carroll, along with Chad and Cole from High Monkey, dive into the importance of inclusive design. In this episode, they focus on the often overlooked but crucial aspect of alt text for images.
Virgil, Chad, and Cole discuss the significance of alt text in creating an inclusive digital experience. They emphasize that alt text is not merely about ticking boxes for WCAG or ADA compliance. Instead, it plays a crucial role in enhancing accessibility and inclusivity for individuals who rely on screen readers. The discussion covers the various types of images—decorative, practical, and informative—and offers insights on how to accurately describe them to improve the digital experience for everyone.
The episode also explores the limitations of relying solely on AI to generate alt text, underscoring the importance of human-crafted, meaningful descriptions that can profoundly impact users who depend on assistive technologies. Furthermore, the team shares practical tips on integrating inclusive design practices into your content creation process, ensuring that your digital content is accessible and understandable to all users.
Throughout the episode, you'll gain valuable knowledge on how to implement best practices for alt text and learn why it's essential to consider inclusivity at every stage of your content lifecycle. By the end of the discussion, you'll be equipped with the tools and insights needed to make your digital content more accessible and inclusive.
Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.
LINKS
Tools mentioned:
Wave: https://wave.webaim.org/
Lighthouse: https://developer.chrome.com/docs/lighthouse/overview/
Alt text examples from the episode: https://www.discussingstupid.com/p/episode-1-alt-text-examples/
Resources from the Web Accessibility Initiative:
Decorative images: https://www.w3.org/WAI/tutorials/images/decorative/
Informative images: https://www.w3.org/WAI/tutorials/images/informative/
Tips and Trick
Subscribe for email updates on our website:
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Listen on Apple Podcasts, Spotify, or Soundcloud:
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The challenges of translating design into a responsive website build
Discussing Stupid: A byte-sized podcast on stupid UX
03/18/25 • 19 min
Discussing Stupid has a new look! This episode marks the beginning of our refreshed brand—featuring a brand new website, sleek color scheme, updated album cover, and a restructured intro sequence. While our look has evolved, our mission remains the same: breaking down the biggest digital mistakes so you don’t have to make them.
In Episode 11, host Virgil Carroll is joined by co-host Cole from High Monkey, along with developer Chad, to tackle a common but frustrating issue—why web designs that look perfect in Figma often fall apart when built for real-world use.
They explore the biggest challenges of translating static designs into fully responsive websites, including:
✅ The problem with designing for just one screen size
✅ Why text, images, and layouts often break in development
✅ What developers wish designers knew about responsive design
✅ Lessons learned from their own website redesign mistakes
Chad shares a developer’s perspective on why rigid, pixel-perfect designs don’t always work and how to approach layouts with flexibility in mind. Through real-world experiences—including High Monkey’s own site rebuild—the team discusses the need for good communication between design and development and how to avoid the most common headaches.
To close things out, they share practical tips on designing for multiple screen sizes, working more effectively with developers, and ensuring that your website doesn’t just look great—it actually functions for all the devices browsing your website.
New intro, new look, new website, same crew ready to help you avoid dumb digital mistakes! Join us every two weeks for fresh episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.
(0:00) - Intro
(2:06) Design is checkers... development is chess
(4:53) Common responsive design fails
(7:18) Unfortunately we are speaking from experience.
(11:09) How many breakpoints do you design for???
(15:40) Designers & developers need to talk
(18:07) - Outro
Subscribe for email updates on our website:
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Watch us on YouTube:
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Listen on Apple Podcasts, Spotify, or Soundcloud:
https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0
https://soundcloud.com/discussing-stupid
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The Semantics of Search | Brett Matson, Funnelback
Discussing Stupid: A byte-sized podcast on stupid UX
05/15/19 • 46 min
In this episode of the Discussing Stupid podcast your host Virgil Carroll has a conversation with Brett Matson, the Managing Director of Funnelback Search Technology, about search, semantic search, knowledge graphs, artificial intelligence in search, and the related leverages and pitfalls.
Brett shares that there are several big things coming in the area of search, after reaching a plateau and stagnation for a few years. Some of these are paradigmatic (understanding the search has multiple purposes, not just page rankings,) and some include changing the approach (i.e. modifying queries,) changing presentation of results (modules,) knowledge graphs, semantic search (detecting the intent of the query,) and many more.
Brett explores how some of these new technologies are intrinsically more attractive to people. For example, knowledge graphs are (or can be) visual and show relations between entities in them. Thus, they are much more intuitive in contrast to being faced with a wall of data to choose from. The point is, of course, making content a lot more intelligent and hence more useful, by treating it as a product and perfecting its delivery.
In Brett’s opinion, during the next decade we will see a real proliferation of smart tools that will help users and companies perform a significantly better search. Virgil and Brett also discuss how it is very important to avoid making too many connections when using a new, powerful technology that can do that. This can bog down the whole organization, its data servers, employees, and finally, users.
Virgil’s conversation with Brett is very rich and diverse, so make sure to listen to the whole episode and pay close attention to what he had to share.
Links:
Episode mentioned:
Future-proofing your experience delivery strategy with Intelligent Content by Kate Skinner.
Siraj Raval's YouTube channel is full of short, fun videos that teach all different aspects of machine learning and AI.
Coursera's Machine Learning course, one of the original online machine learning courses, delivered by leading AI researcher Andrew Ng.
A great article by Sebastien Dery discussing the challenges of knowledge graphs.
Subscribe for email updates on our website:
https://www.discussingstupid.com/
Watch us on YouTube:
https://www.youtube.com/@discussingstupid
Listen on Apple Podcasts, Spotify, or Soundcloud:
https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0
https://soundcloud.com/discussing-stupid
Check us out on socials:
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Episode 1: The hype and sensibility of Artificial Intelligence in Search | Ben Tilley, Funnelback
Discussing Stupid: A byte-sized podcast on stupid UX
04/11/18 • 34 min
On our very first podcast (episode 1 YEAH!!!), Virgil is joined by Ben Tilley from Funnelback, an Australian-based search company, to break through all the hype around the use of artificial intelligence in search and talk about real world implementations and pitfalls.
Listening to this discussion, you will discover that implementing AI in search is not all that easy (shocker!!) and still requires you to follow good content and search practices. Where AI has many practical applications in search, effort is still needed and fundamentals need to be followed. In the end, AI cannot fix your search if your content still sucks.
There is reason to hope, good AI can be very helpful. According to Ben, "Being able to use some form of natural language processing to extract information out of your written text and turn that back into structure is a great way you can start to improve search."
Throughout this episode, Virgil and Ben will share the challenges you will face while giving you thoughts on how you can get your content and search ready to be able to use AI to its full potential.
Resources discussed:
- https://www.wolframalpha.com/ - one of the first search engines to use AI
- https://www.westpac.com.au/ - example organization using AI in their search
Helpful articles from Funnelback:
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FAQ
How many episodes does Discussing Stupid: A byte-sized podcast on stupid UX have?
Discussing Stupid: A byte-sized podcast on stupid UX currently has 26 episodes available.
What topics does Discussing Stupid: A byte-sized podcast on stupid UX cover?
The podcast is about Ux Design, Graphic Design, Marketing, Content Strategy, Podcasts, Technology, Digital Strategy, Digital Marketing, Business and Search.
What is the most popular episode on Discussing Stupid: A byte-sized podcast on stupid UX?
The episode title 'Consistent UX across multiple channels | Kanwal Khipple, 2toLEAD' is the most popular.
What is the average episode length on Discussing Stupid: A byte-sized podcast on stupid UX?
The average episode length on Discussing Stupid: A byte-sized podcast on stupid UX is 24 minutes.
How often are episodes of Discussing Stupid: A byte-sized podcast on stupid UX released?
Episodes of Discussing Stupid: A byte-sized podcast on stupid UX are typically released every 14 days.
When was the first episode of Discussing Stupid: A byte-sized podcast on stupid UX?
The first episode of Discussing Stupid: A byte-sized podcast on stupid UX was released on Apr 11, 2018.
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