What if software had a final season? Josh Williams is back for round two, and this conversation goes places the first one didn't. We get into designing as a generalist instead of a specialist, why some of the best products (RIP Gowalla, RIP Path) might have worked better as limited series instead of forever-apps, and what it actually feels like to use AI tools day to day — not the hot-take version, the real one, where the hardest part isn't the tech, it's knowing when to stop adding features.

Josh also breaks down how the Mosaic icon pack came together, Jory reflects on why his dad's Vermont highway signs are a kind of legacy he thinks about often, and Josh shares his advice for those getting into icon design today. Spoiler: it involves not knowing the rules yet, and that's a good thing.

What We Cover

• Why physical, tangible work sticks with you in a way digital work — which can vanish with a hard drive — never quite does.
• Jory's dad's landscape architecture and signage firm, and how that legacy is scattered across Vermont
• The Mosaic icon pack, and how Scott Riley's Mindful Design site used FA's Slab icon set in a way the team never expected
• Generalist vs. specialist: why Josh keeps circling back to brand work but can't stay in one lane
• The venture-capital pressure that pushes good products toward becoming "everything apps"
• Gowalla, Path, and the idea of software with a beginning, middle, and end — like a TV show's final season
• The early App Store era of one-off apps that just were what they were (RIP the beer-drinking app)
• Font Awesome's own internal AI experiment weekend, and what came out of it
• Taste and discernment as the new bottleneck now that building is fast and cheap
• Why "don't be obsequious" should now be a standing instruction in AI prompts
• Josh's advice for anyone starting out in icon design today
• What's next for the Uni calendar, and a wishlist for a fully custom, build-your-own version

Timestamps

00:00 – Reaching the edge of current tools and processes 

00:00 – Intro: what this episode covers 01:00 – The joy of physical, tangible design work 

02:00 – Jory's father's legacy in Vermont signage 

04:00 – How the Mosaic icon pack might get used and remixed 

05:00 – Generalist vs. specialist: where Josh lands 

07:00 – Bringing different people and disciplines together 

08:00 – VC pressure and the "scale infinitely" mindset 09:00 – Software with a beginning, middle, and end 

11:00 – Gowalla, Path, and products as a moment in time 

13:00 – Building an intentional, sustainable studio model 

14:00 – The early App Store's one-off apps 

17:00 – Font Awesome's internal AI experiment weekend 

19:00 – Taste and discernment as the new bottleneck 

20:00 – Prompting AI to not be obsequious 

21:00 – Advice for getting into icon design today 

23:00 – Breaking the rules you don't know exist yet  – The Mosaic pack vs. the Uni calendar rules 24:00 – A wishlist: fully custom, build-your-own calendars 

25:00 – Where to find Josh, and what's next for him

Credits

• Featuring Josh Williams and Jory Raphael
• Hosted, Produced, and edited by Matt Johnson
• Theme song by Ronnie Martin
• Music interstitials by Zach Malm
• Video editing by Isaac Chase

Links

• Font Awesome Mosaic icon pack
• Josh Williams: @JW on Instagram and Threads

Hashtags

#PodcastAwesome #IconDesign #FontAwesome #DesignPodcast #AIandDesign #ProductDesign #BrandDesign #TechPodcast #CreativeIndustry #DesignCareers

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