For The Culture: On beauty, AI slop, and what lasts when software companies die with Andy Allen Artwork

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Poets & Thinkers explores the humanistic future of business leadership through deep, unscripted conversations with visionary minds – from best-selling authors and inspiring artists to leading academic experts and seasoned executives.

Hosted by tech executive, advisor, and Princeton entrepreneurship & design fellow Ben Lehnert, this podcast challenges conventional MBA wisdom, blending creative leadership, liberal arts, and innovation to reimagine what it means to lead in the AI era.

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Poets & Thinkers

For The Culture: On beauty, AI slop, and what lasts when software companies die with Andy Allen

March 11, 2026 • Benedikt Lehnert • Season 2 • Episode 20

0:00 | 55:31

What if the best business advice ever came from a five-year-old: “I think you should add some googly eyes and rainbow colors!”

In this episode, Ben sits down with Andy Allen, co-founder of Not Boring Software, 2 times Apple Design Award winner, and former co-founder of the groundbreaking startup FiftyThree – makers of the Paper app and Pencil stylus.

Andy challenges the dominant narrative of software design: While the industry has matured and systematized around efficiency and automation over the last 30+ years, he argues we've lost the cultural impact, the playfulness, the human expression that makes software worth making. As he draws parallels to fashion and industrial design, Andy reveals why software designers have no heroes to look up to – only billionaires – and why that's a problem. His students at the University of Washington taught him to remember why he became a designer in the first place: not to optimize conversion funnels, but to make things that matter.

This is a conversation about slowing down and embracing play.

Resources & References

For The Culture (Andy’s manifesto): https://notbor.ing/words/for-the-culture

Not Boring: https://notbor.ing/

FiftyThree launches Pencil: https://www.theguardian.com/technology/2013/nov/19/fiftythree-paper-pencil-ipad-stylus

Connect with Andy Allen

Linkedin: https://www.linkedin.com/in/andrewsallen/

Bio:

Andy Allen is the Alaskan-born, founder of !Boring Software Ltd creating fun software for life's boring routines (2x Apple Design Awards). Co-Founder of FiftyThree and the popular drawing app, Paper (acquired). Adjunct Professor of Software Design at the University of Washington's School of Art.

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