Podcast Awesome

• Living the Dream: Dan Cedarholm's Creative Journey (Part 1)

  SummaryDesigner, author, and co-founder of Dribbble, Dan Cederholm joins Podcast Awesome to chat with Matt Johnson and Jory Raphael about finding joy in creativity later in life, making fonts just for fun, and the art of embracing imperfection. From typefaces and merch to dice games and design detours, Dan shares how side projects, constraints, and a healthy dose of curiosity keep the creative spark alive.This two-part conversation is full of laughter, nostalgia, and lessons about learning new things just because they’re fun. You’ll walk away inspired to make something— anything — awesome.Key TakeawaysCreativity thrives in curiosity: Dan reminds us that learning new things (even outside your job) can reignite your creative energy.Constraints fuel originality: Sometimes not knowing everything — or having limited tools — can sometimes help create the most human, interesting work.Merch can tell a story: From fonts to dice games, playful side projects become part of a designer’s personal brand.Imperfection = personality: The best designs often come with flaws that make them real, memorable, and relatable.Spend time not doing your job: Font Awesome’s team philosophy — creativity grows when you step outside your usual sandbox.Timestamps00:00 — Introduction and catching up with Dan Cederholm02:00 — Typefaces as creative puzzles06:00 — The joy of passion projects10:00 — The first font and lessons from “Chameleon”18:00 — The lineage of icon design and learning from imperfection26:00 — Failures, Field Notes, and finding the next fun thing30:00 — Creative constraints and the beauty of not knowing everything36:00 — Humor, joy, and “making stuff that makes you laugh”38:00 — The icons that exist just because they’re funny42:00 — Hidden glyphs, zombie hands, and bonus icons in fonts44:00 — Wrap-up and where to find Dan onlineRelated LinksSimpleBits.com — Dan’s home for fonts, merch, and creative experimentsDan’s Newsletter — The one Font Awesome staffers never skipDribbble — Co-founded by Dan, still inspiring designers everywhereCreditsProduced and edited by Matt Johnson Video editing by Isaac Chase Theme music by Ronnie Martin Interstitial music by Zach MomStay up to date on all the Font Awesomeness!

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• How We Built Web Awesome with 11ty (and Why It’s So Fast)

  Build once, run everywhere. In this full-nerd, front-end-leaning episode of Podcast Awesome, Matt sits down with Zach Leatherman (creator of Eleventy) and Konnor Rogers (Web Awesome developer) to chat about how a static site generator just might be the key to building some of the most powerful, performant documentation on the web.We dig deep into Eleventy’s evolution, Web Awesome’s hybrid architecture, and how a team of devs found a way to keep docs fast, flexible, and secure — without rewriting everything from scratch or giving up on open source values. Spoiler: they didn’t go full ExpressJS for fun.Whether you’re a seasoned dev or a newb, this one's packed with insight, edge-case explorations, and some seriously satisfying build-time nerdery.In this episode, we explore:⚡️ Why Eleventy’s simplicity still scales 🧠 Making static sites feel dynamic (without a heavy JS framework) 🔐 How Web Awesome handles auth + private docs with minimal friction 🚫 Avoiding vendor lock-in and runtime gotchas 📦 The future of Eleventy in browsers, edge runtimes, and beyondPull up your terminal. This one’s for you.🔗 Links & Credits🎵 Theme by Ronnie Martin🎛️ Audio mastering by Chris Enns (Lemon Productions)🎹 Interstitial music by Zach Malm🎥 Video support by Isaac Chase🔗 Eleventy🔗 Web AwesomeStay up to date on all the Font Awesomeness!

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• Clippy Cult: The Paperclip That Wouldn’t Quit

  Inside the UX lessons, internet lore, and surprising comeback of ClippyLove him or loathe him, you remember him. Clippy — the googly-eyed paperclip that lived inside Microsoft Word — has become a permanent fixture in internet culture. But how did a productivity tool become the patron saint of annoying-yet-adorable UI? In this episode of Podcast Awesome, we’re digging into the cult of Clippy with behind-the-scenes insights from Clippy's original creator Kevan Atteberry and Microsoft designer Sam Cundall. From meme fame to Microsoft Teams emoji, Clippy's legacy is more layered than you think.📝 What We Cover in This Episode:📎 Why Clippy was loved and hated🧠 The psychology of nostalgic design🔁 When Microsoft secretly brought Clippy back🤖 What Clippy might teach us about the future of AI assistants✍️ thoughts on reviving legacy designs the right way⏱️ Timestamps: 00:00 – Welcome to the Cult of Clippy 02:00 – The origin story: from helpful to hated 04:30 – Nostalgia and annoyance: why we love to hate him 06:00 – Microsoft’s secret Clippy emoji comeback 08:00 – What makes emoji design "work"? 10:00 – Fun at work: why weirdness builds culture 14:00 – The creator's take: Kevan Atteberry on designing Clippy 20:00 – From embarrassment to pride: Clippy's redemption arc 24:00 – Clippy vs. Siri: The rise of personality-driven UI 26:00 – Final thoughts: where personality fits in UX🔗 Links & Resources:Sam Kundal on LinkedInKevan Atteberry's booksHow to add a paperclip emoji to your UIVote a favorite icon up the leaderboard🎥 Podcast Awesome on YouTube 🎶 The Font Awesome Theme Song – Composed by Ronnie Martin🎸 Music Interstitials by Zach Malm🎬 Produced and edited by Matt Johnson with some extra help from Isaac Chase Stay up to date on all the Font Awesomeness!

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• 🎙️ Rage Coding, Headless Web Components, and the Future of DX with Burton Smith

  Have you ever rage-coded your way into building a developer tool that actually fixes things? Burton Smith has. And we’re here for it.In this episode of Podcast Awesome, Matt and Web Awesome's boss, Cory Laviska chat with Burton Smith. Burton is an open source wizard and creator of the Web Components Toolkit, and he tells us about the gap between the promise of Web Components and the messy reality devs often face.💻 Burton’s toolkit bridges that gap like Gandalf on a DX bender.In this episode we dive into: ⚙️ Developer experience pain points 🧩 Custom Elements Manifests (CEMs) and real-world tooling 🎯 Form-associated custom elements, declarative shadow DOM, and why they still have rough edges 🚀 Why frameworks finally (mostly) play nice with Web Components 📦 How open source tools can fix the stuff we all silently suffer through 🧠 And why making components “just work” should be table stakesThis one’s for devs who are tired of wiring up wrappers, fighting with VS Code autocomplete, or wondering why their component still doesn’t show up right in Storybook.✨ Bonus: We get a little spicy about SSR, headless UI, and whether a global design system is even a thing we want.⏱️ Timestamps00:00 – Welcome to Podcast Awesome 02:00 – Meet Burton Smith: The Stuff Breaker 04:00 – Why Web Components Tooling is (Still) a Pain 06:00 – Closing the Gap Between DX and Dev Reality 12:00 – CEMs, ASTs, and Metadata Magic 20:00 – Form-associated Custom Elements (and the Weird Gaps) 24:00 – Declarative Shadow DOM: Blessing or Band-Aid? 28:00 – SSR, Frameworks, and the Next Frontier 34:00 – Global Design Systems, Gatekeeping, and Interop 42:00 – Headless UI vs. Useless DX 44:00 – How to Support Burton + Where to Find the Toolkit🔗 Links & Resources🌐 Burton’s Toolkit: https://wc-toolkit.com🧙‍♂️ Follow Burton on GitHub: https://github.com/Breakstuff🐦 Burton on Social: @StuffBreaker📄 Learn more about Custom Elements Manifest: https://github.com/webcomponents/custom-elements-manifest🛠️ Web Awesome: https://webawesome.dev🧡 Shoutout to all you open sourcers building magic after hours🎥 Podcast Awesome on YouTube 🎶 The Font Awesome Theme Song – Composed by Ronnie Martin🎸 Music Interstitials by Zach Malm🎬 Produced and edited by Matt Johnson with some extra help from Isaac Chase Stay up to date on all the Font Awesomeness!

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• 🖇️ Podcast Awesome: The Story Behind the Stapler Icon

  🔴 “Excuse me … I believe you have my stapler?”One line. Infinite memes. A red-hot icon.In this episode of The Story Behind the Icon, we dive deep into the surprisingly rich lore behind the humble office stapler — and how a cult classic film, a soft-spoken cubicle dweller, and a spray-painted prop turned it into a cultural artifact.🎧 Whether you’ve got 37 pieces of flair or just enough sarcasm to survive corporate life, this one’s for the design nerds, Office Space devotees, and UI jokesters looking for the perfect button metaphor.🔍 What We Cover in This Episode🔴 The origin story of Milton’s beloved red stapler 🎞️ Mike Judge’s animated roots and early Office Space shorts 💻 Remote work, legacy office gear, and the evolution of workplace design 🧑‍💼 Font Awesome’s very own “Milton” and the logic behind the madness 🎨 How to recreate Milton’s soul in HTML with our duotone icon 🎬 The real reason Swingline started making red staplers⏰ Timestamps00:00 – Welcome to Podcast Awesome 01:25 – A new take on the old office 02:40 – Meet Milton: The patron saint of passive resistance 04:20 – Mike Judge: From Beavis and Butthead to box office satire 05:55 – The stapler becomes an icon 06:35 – Meet FA’s own Milton (Hi, Steve 👋) 07:20 – Grumpiness as UI insight 08:05 – Milton’s stapler wasn’t red... until it was 09:00 – Design challenge: Where will you use the stapler icon? 09:50 – Commission your own icon or vote one into existence 10:30 – Credits and a final plea: Return. The. Stapler.🔗 Links & Resources🖇️ Stapler Icon on Font Awesome 📽️ Office Space (1999) 🎨 Vote for an icon on the leaderboard 📝 FA Blog: The Story Behind the Icon Series🎥 Podcast Awesome on YouTube – Full uncut convo with extra music nerdiness 🎶 The Font Awesome Theme Song – Composed by Ronnie Martin 🎸 Music Interstitials by Zach Malm 🎬 Produced and edited by Matt JohnsonStay up to date on all the Font Awesomeness!

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