Aparna Chennapragada+

What is your Golden Gate Bridge?

The Overfitting Trap for Leaders and Companies

Every Maker Is Now a Manager (of AI)

RIP Maker Schedule. Unless we invent calmer human-AI interfaces.

2026: Year of Deep Work

(I spent some time during the holidays building with GitHub Copilot, Claude Code, and thinking about what's next for the agents our team builds at Microsoft, such as Researcher.

Thick Steps and Thin Steps in the AI era

What are the Fedex and Sears of the Intelligence Age?

The Latent Long Tail of Ideas

Investable thesis #2: Bet on tools and platforms enabling the next set of long tail amateurs.

Designing Intelligent Products: Category Collapse

Designing for Impact:

Design for Learning

(Part of the “Designing Intelligent Products” series, the first part starts here).

The Legibility and Control Trap

How We Mistake Control for Confidence

What's your WOW:WTH ratio

(This essay is part of the ongoing “Designing Intelligent Products” series, introduction here)

Designing Intelligent Products: Design for Trust

Principle: Make the UI Proportional to the AI

Designing for Trust

Principle #1 Show Your Work

Artificial Super Diligence - The Waymo lesson

We spend so much time debating Artificial Super intelligence (ASI) but the biggest value today is in Artificial Super Diligence. It's the idea hiding in plain sight: AI that never tires, never skips, never lets small mistakes snowball into catastrophe.

All Leaders are GPT-5s

Balancing between instruction followers and reasoners

Designing Intelligent Products

NLX is the New UX

Most Work is Translation

And LLMs are the first universal translators for work.

From Clickbait to Pleasebait

Clickbait and Pleasebait

The Bitter Lesson: Product version

Will Learning loops beat designed UX?

Doc is cheap. Show me the talk.

“Talk is cheap.

Prompt sets are the new PRDs

A lot of folks have heard me say (on Lenny’s podcast , for example, that Prompt sets are the new PRDs.

Beware The Six Finger Trap

Model continues to eat the product. So build to where the model puck is going.