Hi! My work and interests lie at the intersection of AI, engineering, writing, and knowledge tools.
I believe the purpose of technology is to improve our collective intelligence and to solve human problems. A bit more about me:
- Tech: Have build conversational AI systems since early days at SRI with the original Siri team. Built search engines with prominent ex-Google engineers. I have a broad interest in the theory, the practice, and the human element of software engineering, and the history software and AI. Even longer ago, I studied mathematics at Berkeley. Tech stacks I've used the most are a variety of frameworks in Web, React, JS/Node, Python, Java, C/C++, Lisp, and (yes) Prolog.
- Engineering: Have been a founding engineer and eng leader at several startups in AI, SaaS, and web search (some failed, some successful).
- Writing: Wrote and edited few popular guides (2M+ readers), including The Art of Command Line (which is apparently a top-40 most popular GitHub repo of all time), equity compensation, and AWS. Editor and publisher on about a dozen books.
- Recent work: I started and run Holloway, a platform that has rebuilt the digital book publishing process with dozens of in-depth, web-based guides in entrepreneurship, creativity, and personal growth. We also publish print books. I love to talk to authors, experts, and anyone who cares about sharing high-value knowledge.
- Inspiration: The technologist I most admire is Doug Engelbart. His work is as relevant today as it was 50 years ago.
- Random: I try to learn a few things about many topics and many things about a few topics. My interests include good books of all kinds, startups, AI, software engineering, philosophy, design, typography, psychology, fitness, fingerstyle guitar, Brazilian Portuguese, kindness, truth, and other arcana.
Find me:
I'd be glad to hear from you if we share interests. If you're trying to reach me, note I sometimes fall behind on messages. I don't mind reminders and more detail or context in a message helps. :)




