Benjamin Stein

Benjamin Stein

CEO of SuperDuper. President of Piedmont Makers. Oakland, CA.

Ayo! I'm Ben. I live in Oakland, CA with my illustrious wife, two teenage boys, and a pup named Soup. I love birds, bridge, beer, bots, bears, beets, Battlestar Galactica. And losing at pub trivia. Electrify everything.

Current Status: Reading Dikkens with two Ks, the well-known Dutch author
Previously: Memorizing jokes from Cap'n Billy's Whiz Bang


Writing

I Was Wrong About LLM Writing

I spent two years treating all LLM writing as slop. Turns out there's a crucial distinction between using AI as a microwave burrito and using it as a compiler for...

February 12, 2026

The Blinking Cursor

We launched Teammates to create virtual colleagues that actually understood you. The hard truth: 9 out of 10 just sat there.

February 2, 2026

How to Protect Yourself Online (2026 Edition)

Every year I write an updated guide for friends and family who want a New Year's Resolution that might actually stick. Here's my latest for 2026.

November 14, 2025

The Stein Family Pet Naming Tradition: A Comprehensive History

Our dog is named Matzah Ball Soup. Before him, our beagle was named Kugel. The hamsters were Falafel and Babka. Our family has been naming pets after Jewish foods since...

November 13, 2025

Sisyphus Only Had One Boulder (I Have Four)

I love a clean house. My family is the opposite. One day I'll win. Or will I?

November 13, 2025

How to Make Your Blog AI Agent-Friendly (And Why You Should)

I added two lines to my blog's HTML header. Those two lines enabled AI agents to read my blog posts directly—not just humans with browsers anymore.

November 12, 2025

Everyone Says They Can Spot AI Writing—Can You? 🤔

I built a collaborative team of copywriters that run inside Claude Code (what?!) that automate my writing process--without sounding like an LLM

November 12, 2025

On Approaching 50 with Hot Pink Hair

Nine months ago, I walked into a hair salon and asked for hot pink hair. I get lots of questions. This answers some of them.

November 5, 2025

We Let Our AI Deploy Itself to Production (And Accidentally Created Your Next Favorite Pixar Character)

Our staging server writes poetry, calls me 'Skipper', and wants a promotion. Let me explain.

October 28, 2025