Hi! In case you want to get to know me or my work, this is a cheat sheet.
Work and Interests
Generally, my interests lie at the intersection of AI, writing, software
engineering, design, and knowledge tools:
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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!)
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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.
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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.
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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.
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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.
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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.”
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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
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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.
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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.
Projects
Some new projects: ✨new!✨
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New tools to help with agent coding (and some that were fully agent coded)
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tbd: Git-native issue tracking for AI agents and humans, inspired by beads
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Markform: Structured Markdown documents for agents and humans
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Speculate: Extensive doc library and project structure for spec-driven agent coding
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tryscript: Golden testing for CLI apps (very useful for helping agents write CLIs for agents!)
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New knowledge and content tools
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Kash: A new kind of shell (experimental but
usable!)
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Textpress: Simple publishing for complex
ideas
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simplexng: A repackage of the local
SearXNG web search engine you can run with one command
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Document/Text/LLM libraries
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flowmark: Better auto-formatting for
Markdown
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chopdiff: Parsing, diffing, diff filtering,
chunking, and windowed transforms of text to support LLM applications
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tminify: Modern JS/CSS/HTML
minification with terser plus Tailwind v4 compilation as a CLI and Python library
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frontmatter-format and sidematter-format: Simple conventions and formats for metadata and assets on any file or alongside any file
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repren: Rename anything
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Python infra
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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 uvtemplate)
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uvx uvtemplate: Start a new Python project with one
command
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py-app-standalone: Standalone,
relocatable Python app builds using uv
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strif: Tiny, useful Python lib for strings and
files
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funlog: Minimalist decorators for logging,
timing, and tallying function calls
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prettyfmt: A tiny library for more
beautiful Python outputs
A few new writings (these are rough and would appreciate feedback) ✨new!✨
Other projects:
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on-books: Readings and notes on the past,
present, and future of books
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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!)
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og-aws: A practical guide to Amazon Web
Services (35K+ stars, for a while one of the most popular docs ever for AWS)
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og-equity-compensation:
Original open source version of a guide to equity compensation for startup employees
and founders (9K+ stars)
Reaching Me
Please reach out if you think you should!
I’d be glad to hear from you if we share interests.
:)