Poets & Thinkers For The Culture: On beauty, AI slop, and what lasts when software companies die with Andy Allen
Mar 11, 2026
Andy Allen, co-founder of Not Boring Software and creator of the Paper app and Pencil stylus, is an award-winning software designer and UW adjunct professor. He talks about reclaiming play and beauty in software. He argues design lost cultural impact as the industry optimized for efficiency. He discusses remaking everyday apps, teaching’s influence, and how small studios can build expressive, lasting products.
AI Snips
Chapters
Transcript
Episode notes
Courier's Cancellation Sparked FiftyThree
- Andy described leaving Microsoft after the canceled Courier project to start FiftyThree and build Paper and Pencil, pioneering touch-first creative tools.
- Paper became a defining touch-era app and Pencil a top-selling stylus before the Apple Pencil arrived.
Software Grew Up But Lost Cultural Ambition
- Software has matured from handcrafted experiments into highly automated, systematized products, which improved scale but narrowed cultural and aesthetic ambition.
- Andy argues this shift left a gap: fewer software 'heroes' and less work that pushes design as cultural expression.
Students Remind Designers Why They Started
- Teaching design reignited Andy's optimism because students hadn't yet accepted efficiency-first narratives and instead pursued expressive, exploratory work.
- That contrast revealed software lacks the visible creative heroes that other design fields celebrate.