95: !Boring Software — Andy Allen

95: !Boring Software — Andy Allen

July 1, 2026 · 1h 24m · Episode 95

About this episode

Andy Allen discusses his journey from designing the Microsoft Courier tablet to founding !Boring Software, emphasizing the importance of design and staying small in business.

On the podcast: Andy Allen shares how he went from designing the never-shipped Microsoft Courier tablet and co-founding the Apple Design Award-winning drawing app Paper to starting !Boring Software (Not Boring Software) — a deliberately tiny, 2-person studio built around one rule: never make boring software again. He talks about why staying small on purpose protects you from getting trapped in a business you hate, how a "patron plan" with no extra features outsold expectations, why sound design and haptics are the most underused tools in app development, and how 3 years of false starts led to Not Boring Camera — an app that strips out all of Apple's photo processing so you can take expressive photos instead of technically perfect ones. Top Takeaways: 🎨 Design can be the entire value proposition — not just a nice-to-have People pay premiums for notebooks, furniture, and cars based on aesthetics, yet the software industry still assumes you need feature differentiation to charge money. 🔒 The biggest risk isn't failure — it's getting trapped in a business you don't want to run Structure your company, your incentives, and your product roadmap around the work you actually want to do…

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