Generally, my interests lie at the intersection ofAI,writing,softwareengineering,design, andknowledge 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, andtools 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’vewritten a few popular guides (2M+ readers), including theThe Holloway Guide toEquity Compensation (the most widelyread guide to equity compensation in startups),The Art of CommandLine (150K+ stars on GitHub), anda 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’min the top20 most-starred accounts on GitHub.

• Publishing: I started and built most ofHolloway, a small startup that has rebuilt thedigital book publishing process with dozens of in-depth, web-based guides inentrepreneurship, creativity, and personal growth.We also publish print books.

• AI and software: I’ve worked on conversational AI systems since early days withthe original Siri team at SRI. I’ve built search engines with prominent ex-Googleengineers. I have a broad interest in the theory, the practice, and the human elementsof software engineering, and the history of software and AI.

• Startups and entrepreneurship: I’ve been a founding engineer a few times and afounder. I like working with founders and sometimes consult for or advise startups andinvestors.

• 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, fullstack web/JS/Node/TypeScript/React, Python, Java, C/C++, and older esoteric thingslike 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 collectiveknowledge and intelligence and to solve human problems.The technologist I most admire isDoug Engelbart. His work is asrelevant 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 issimple—truth, helpfulness, and kindness.

• Miscellaneous: I aim to know a few things about many topics and many things abouta few topics. I majored in physics, math, and computer science and my graduate degreeis from Berkeley. I like to think or talk about good books of all kinds, philosophy,psychology, politics and media, startups and entrepreneurship, AI (history andfuture), product design, typography, software engineering, logic and foundations ofmathematics, mental and physical health (and their interactions), fitness andnutrition, running or hiking the mountains and deserts of California, fingerstyleguitar, 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

  • Kash: A new kind of shell (experimental butusable!)

  • Textpress: Simple publishing for complexideas

  • simplexng: A repackage of the localSearXNG web search engine you can run with one command

• Document/Text/LLM libraries

  • flowmark: Better auto-formatting forMarkdown

  • chopdiff: Parsing, diffing, diff filtering,chunking, and windowed transforms of text to support LLM applications

  • tminify: Modern JS/CSS/HTMLminification with terser plus Tailwind v4 compilation as a CLI and Python library

  • frontmatter-format andsidematter-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, modernPython project template, good if you’re starting a new project, withuv/ruff/Pyright/GitHub actions/PyPI publishing (used by uvinit)

  • uvx uvinit: Start a new Python project with onecommand

  • py-app-standalone: Standalone,relocatable Python app builds using uv

  • strif: Tiny, useful Python lib for strings andfiles

  • funlog: Minimalist decorators for logging,timing, and tallying function calls

  • prettyfmt: A tiny library for morebeautiful Python outputs

A few new writings (these are rough and would appreciate feedback)✨new!✨

• The Philosophy of CommandLine: Some philosophicalreflections on software

• Linters for Thought: Reflections on SoftwareEngineering 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 oneof the top 40 most starred GitHub repos of all time, but in need of an update, which Ihope to do soon!)

• og-aws: A practical guide to Amazon WebServices (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 employeesand 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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1. the-art-of-command-linethe-art-of-command-linePublic

   Master the command line, in one page

   159k 14.8k

2. frontmatter-formatfrontmatter-formatPublic

   A simple convention for YAML metadata on any file

   Python 19 2

3. simple-modern-uvsimple-modern-uvPublic

   A minimal, modern Python project template using uv. An instantiated version of this template here

   Jinja 240 17

4. uvinituvinitPublic

   A time-saving CLI to start new, modern Python projects

   Python 49

5. strifstrifPublic

   A tiny, useful Python lib of string, file, and object utilities

   Python 126 10

6. flowmarkflowmarkPublic

   Modern Markdown formatter with smart typography and paragraph wrapping

   Python 42 6