Hi! In case you want to get to know me or my work, this is a cheat sheet.
Generally, my interests lie at the intersection of AI, writing, software engineering, design, and knowledge tools:
Recent work: ✨new!✨ Lately I’m working on some new ideas for knowledge tools, including an AI-native command line, some open source Python libraries for LLM, and tools related to uv. (See below and do reach out you’re interested or have ideas related to any of these!)
Writing and open source: I’ve edited (and published) about a dozen books and I’ve written a few popular guides (2M+ readers), including the The Holloway Guide to Equity Compensation (the most widely read guide to equity compensation in startups), The Art of Command Line (150K+ stars on GitHub), and a guide to AWS. And I’ve written an number of open source libraries in Python. Popularity isn’t the best measure of value, but I’m in the top 20 most-starred accounts on GitHub.
Publishing: 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.
AI and software: 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.
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 startups and investors.
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.
Values: There is great beauty in understanding the essential complexity of life. But the opposite of a great truth is another great truth: what matters is simple—truth, helpfulness, and kindness.
Miscellaneous: I aim to know a few things about many topics and many things about a few topics. I majored in physics, math, and computer science and my graduate degree is from Berkeley. I like to think or talk about 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.
Some new projects (mostly Python): ✨new!✨
New knowledge tools
Document/Text/LLM libraries
flowmark: Better auto-formatting for Markdown
chopdiff: Parsing, diffing, diff filtering, chunking, and windowed transforms of text to support LLM applications
tminify: Modern JS/CSS/HTML minification with terser plus Tailwind v4 compilation as a CLI and Python library
frontmatter-format and sidematter-format: Simple conventions and formats for metadata and assets on any file or alongside any file
repren: Rename anything
Python infra
simple-modern-uv: A minimal, modern Python project template, good if you’re starting a new project, with uv/ruff/Pyright/GitHub actions/PyPI publishing (used by uvinit)
uvx uvinit: Start a new Python project with one command
py-app-standalone: Standalone, relocatable Python app builds using uv
strif: Tiny, useful Python lib for strings and files
funlog: Minimalist decorators for logging, timing, and tallying function calls
prettyfmt: A tiny library for more beautiful Python outputs
A few new writings (these are rough and would appreciate feedback) ✨new!✨
The Philosophy of Command Line: Some philosophical reflections on software
Linters for Thought: Reflections on Software Engineering and Collective Intelligence (draft!)
Other projects:
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 (150K+ 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!)
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)
@ojoshe on Twitter/X (this is best for DMs)
LinkedIn (slow on messages here but I try)
see email on my profile
Please reach out if you think you should! I’d be glad to hear from you if we share interests. :)
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