Sep 25, 2026

Raise the ceiling: how to scale intent, quality, and artistry with Al | Katie Dill (Stripe)

Katie Dill from Stripe discusses how the rapid advancements in AI risk leading to "zombie UI" – generic, uncared-for digital products. She draws parallels to post-WWII architecture, highlighting the dangers of building without intentionality or a clear point of view. Dill then offers four key recommendations for developers and designers to leverage AI not just for speed, but to create original, soulful, and user-centric products: defining a strong point of view, encoding quality standards directly into AI tools, embracing meticulous editing beyond the first AI-generated draft, and actively using AI to foster new forms of creativity and unique interfaces.

Sep 08, 2026

Why 95% of All AI Projects Fail - Boris Scharinger | Podcast #174

Boris Scharinger, Industrial AI Strategist at Siemens and author of "Industrial AI: From Pilot to Profit," discusses why 95% of AI proofs of concept fail in industrial settings. He highlights the 5-10x cost multiplier from pilot to production, the critical role of the "harness" around AI models, and the unique challenges of data access and legacy systems in physical environments. Scharinger advocates for a two-tiered investment strategy, separating foundational data capabilities from use-case-specific ROI, and addresses cultural resistances from engineers. He provides guidance on differentiating commodity from strategic AI applications and how to effectively scale industrial AI for profit.

Aug 16, 2026

OpenAI’s Head of Design: This is the best time in history to be a designer | Ian Silber

Ian Silber, OpenAI's Head of Design, discusses the paradoxical anxiety among designers despite AI's transformative potential. He explains why this is the best time to be a designer, emphasizing curiosity, systems thinking, and the human element in an AI-amplified world. The conversation delves into ChatGPT's evolution as a "super app" and the unique design challenges of building for vastly diverse users.

Aug 14, 2026

Susan Kare: How I Designed the Original Apple Mac Icons

Susan Kare, the legendary designer behind the original Macintosh's iconic visual language, shares her journey from art history to computing. She discusses the creation of typefaces like Chicago and memorable icons such as the Happy Mac and the Command key symbol. Drawing lessons from Steve Jobs, Paul Rand, and others, Kare highlights key design principles: focusing on meaning and memorability, embracing technical constraints, iterating constantly, and using just enough detail to ensure instant clarity and universal appeal in human-computer interaction.

Apr 22, 2026

How Stripe Built Their New Website

Stripe's Head of Design, Katie Dill, provides a behind-the-scenes look at their recent homepage redesign. She discusses the strategic shift from a product-list to a narrative-driven approach, the intricate design process behind key elements, and how AI is fundamentally changing their design workflow and empowering their team to fight the "gravitational pull to mediocrity".

Jan 30, 2026

Inside The New YC Website

YC's Aaron Epstein and Eve Bouffard detail the redesign of the YC homepage, shifting from a utilitarian, B2B-style site to an inspirational, founder-centric narrative. They discuss the new design's focus on storytelling, the unconventional AI-assisted development process, and the future of interactive web design.