Crossword Perspectives with Nate Stewart
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Oct 23, 2026 Nate Stewart, a technology entrepreneur and founder of Runtype, discusses rescuing chickens, failed retirement, and the future of AI-assisted development. He explores skill atrophy, taste, and keeping AI outputs human. The conversation also tackles commercialized addiction, WordPress’s open web, collaboration across its ecosystem, and a distributed AI future inspired by GeoCities.
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Neutral Community Roles Can Bridge WordPress Rivals
- WordPress partnerships can benefit merchants while still satisfying Automattic, WP Engine, and the wider community.
- Jonathan recommends a dedicated, neutral community representative who focuses on WordPress rather than corporate conflict.
Nate’s Retirement Turned Into An AI Startup
- Nate tried retiring in Puerto Rico, spending time at the beach, practicing permaculture, and exploring theme parks and sailing.
- Experimenting with vibe coding exposed recurring problems in building complete AI products, motivating Runtype.
AI Products Need More Than A Working Prototype
- Runtype treats AI development as a complete product lifecycle, not merely an API call or generated prototype.
- It helps teams test interfaces, select models, add guardrails, estimate costs, and simulate architectures.