Insights

Essays, guides, and case studies on knowledge, AI, and the organizations putting expertise to work.

What does your AI value? The invisible layer shaping every answer

Newsletter

What does your AI value? The invisible layer shaping every answer

Every AI system encodes invisible assumptions about what counts as a good answer. This week, we unpack the layers shaping what your AI considers trustworthy — and what you can do about it.

by Alex Tryon

Perspectives on AI and expertise.

Dewey Named a Fast Company 2026 World Changing Idea

Dewey Named a Fast Company 2026 World Changing Idea

Why we're betting that human expertise matters more, not less, in the age of AI.

by Alex Tryon

What AI is Changing for Mission-Driven Orgs (And Why It Matters)

What AI is Changing for Mission-Driven Orgs (And Why It Matters)

For mission-driven orgs, the shift to natural-language search is a mission problem — not just a tech upgrade.

by Alex Tryon

Why "I Don't Know" is the Most Valuable Thing Your AI Can Say

Why "I Don't Know" is the Most Valuable Thing Your AI Can Say

Unwarranted overconfidence loses trust, while transparency and honesty do the opposite.

by Alex Tryon

Practical how-tos on knowledge tools.

Best Algolia Alternatives for Content-First Organizations

Best Algolia Alternatives for Content-First Organizations

Every Algolia alternatives list was written for e-commerce. If your organization's value is expertise, not inventory, here's what content-first sites actually need.

by Scott Carleton

Why DIY Chatbots Stop Working After Launch

Why DIY Chatbots Stop Working After Launch

Searching for customgpt alternatives? The real question isn't features — it's who owns the fix when your knowledge evolves and your chatbot doesn't.

by Scott Carleton

Stop Copy-Pasting Your Own Work Into AI

Stop Copy-Pasting Your Own Work Into AI

How MCP turns years of published expertise into a tool you call from anywhere

by Scott Carleton

Sterling Parents

Case Study

Sterling Parents

Members ask Obi instead of Googling at 2 AM — 4,000+ times a month