Hi! In case you want to get to know me, this is your cheat sheet. Generally, my interests lie at the intersection of AI, writing, engineering, design, and knowledge tools:
-
Recent work: I started and built most of Holloway, a small startup 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.
-
Startups and entrepreneurship: I've been a founding engineer a few times and a founder. I like working with founders and sometimes consult for or advise selected startups and investors. I wrote the most widely read guide to equity compensation in startups.
-
Writing: I've written and edited few popular guides (2M+ readers), including the equity compensation guide, The Art of Command Line and AWS. I’ve also edited (and published) about a dozen books by other authors.
-
Tech: I’ve worked on conversational AI systems since early days with the original Siri team at SRI. I’ve built search engines with prominent ex-Google engineers. I have a broad interest in the theory, the practice, and the human elements of software engineering, and the history of software and AI.
-
Engineering: I've loved programming since I was a kid. I have been a founding engineer and engineering leader at several startups in AI, SaaS, and web search, some failed, some successful (backend/distributed sysems, full stack web/JS/Node/TypeScript/React, Python, Java, C/C++, and older esoteric things like Lisp and Prolog). Also devops—AWS has given me the honor of being an "AWS Hero."
-
Inspiration: I believe the purpose of technology is to improve our collective knowledge and intelligence and to solve human problems. The technologist I most admire is Doug Engelbart. His work is as relevant today as it was 50 years ago. By sharing a vision of what was possible, he shaped how we use software for decades. I feel privileged to have met him a few times.
-
Personal: I aspire to know a few things about many topics and many things about a few topics. My interests include good books of all kinds, philosophy, psychology, politics and media, startups and entrepreneurship, AI (history and future), product design, typography, software engineering, logic and foundations of mathematics, mental and physical health (and their interactions), fitness and nutrition, running or hiking the mountains and deserts of California, fingerstyle guitar, 15th-18th century lute music, early American blues, Brazilian Portuguese, truth, kindness, and some other arcana. I majored in physics, math, and computer science and my graduate degree is from Berkeley.
Selected open source code and writings:
- on-books: Readings and notes on the past, present, and future of books
- the-art-of-command-line: Master the command line, in one page (155K+ stars, available in ~20 languages and one of the top 40 most starred GitHub repos of all time, but in need of an update, which I hope to do soon!)
- simple-modern-poetry: A minimal, modern Python project template (with Poetry 2.0 and ruff/black/mypy/GitHub actions/PyPI publishing)
- frontmatter-format: A micro-format for YAML metadata on any file
- flowmark: Better line wrapping and formatting for plaintext and Markdown
- prettyfmt: A tiny library for more beautiful Python outputs
- repren: Rename anything
- strif: Tiny, useful Python lib for strings and files
- og-aws: A practical guide to Amazon Web Services (35K+ stars, for a while one of the most popular docs ever for AWS)
- og-equity-compensation: Original open source version of a guide to equity compensation for startup employees and founders (9K+ stars)
Find me:
Please reach out if you think you should! I'd be glad to hear from you if we share interests. :)