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

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