Breaking
The Art of Command Line: 150,000+ GitHub stars Holloway raises $4.6M from NYT Company and NEA 2M+ readers on the Guide to Equity Compensation From SRI International's Siri team to reinventing publishing 14 languages. 150K stars. One GitHub repo changed everything. Holloway: digital books that don't go out of date by design Now building AI-native tools: Markform + Kash shell The Art of Command Line: 150,000+ GitHub stars Holloway raises $4.6M from NYT Company and NEA 2M+ readers on the Guide to Equity Compensation From SRI International's Siri team to reinventing publishing 14 languages. 150K stars. One GitHub repo changed everything. Holloway: digital books that don't go out of date by design Now building AI-native tools: Markform + Kash shell
Joshua Levy

Joshua Levy / San Francisco

Profile / Founder + Engineer + Publisher

Joshua
Levy

Co-Founder & CEO, Holloway - San Francisco, CA

A mathematician who became an engineer, who became a publisher - because nobody else was building the library the internet deserved.

Holloway CEO 150K GitHub Stars Ex-Viv Labs / BloomReach Open Source Author

Feature Story

He wrote a GitHub guide as a personal note.
Two million people read it.

Joshua Levy didn't set out to reinvent publishing. He set out to remember how to use xargs. The document he wrote - "The Art of Command Line" - started as a private reference, the kind of thing any engineer keeps in a notes file. Then he put it on GitHub. It now has over 150,000 stars, has been translated into approximately 14 languages, and has been read by more than 2 million people. It sits in the top 40 most-starred repositories on all of GitHub.

That's not a lucky accident. It's a pattern. Levy has a talent for taking knowledge that exists only in scattered places - in experts' heads, in Slack messages, in decade-old Stack Overflow threads - and making it findable, readable, and permanent. Holloway, the company he co-founded in late 2016, is the institutional version of that same instinct.

"Assemble and publish reliable knowledge from experts for all to learn from and build on."

- Holloway's founding mission

Before Holloway, Levy was employee number two at BloomReach, a cloud marketing platform he helped grow from a two-person startup to nearly 200 employees. The engineering and operations foundation he built there - infrastructure, team structure, hiring pipelines - prepared him for exactly the kind of scaling work that Holloway would require. After BloomReach, he joined Viv Labs, the AI startup founded by the creators of Siri. It was acquired by Samsung in 2016. A month later, he was building Holloway.

His academic background is unusual for a tech CEO. Levy studied advanced mathematics, including a stint with Budapest Semesters in Mathematics - a program that typically attracts math olympiad veterans and future academic researchers. Earlier, he worked at SRI International alongside the team that built the original Siri. The thread connecting SRI's conversational AI, BloomReach's data infrastructure, Viv Lab's ambient intelligence, and Holloway's knowledge platform isn't obvious from the outside. But it's there: Levy has always been building systems for how humans access information.

150K+ GitHub Stars
The Art of Command Line
2M+ Readers
Equity Compensation Guide alone
$4.6M Seed Funding
NYT Co. + NEA + South Park Commons
14 Languages
Art of CLI translations
⚡

Open Source Impact

The Art of Command Line

What started as a personal cheatsheet became one of the most-starred educational repositories on GitHub. Levy published it openly, the community translated it into approximately 14 languages, and millions of engineers have used it to master the terminal - from complete beginners to those who had been using the command line for years and still found something new.

150K+ GitHub Stars
~14 Translations
2M+ Readers
Top 40 All GitHub Repos

Career Arc

From SRI's Siri team to rebuilding publishing

Early Career

SRI International - Where Siri was born

Software engineer at SRI International, working on conversational AI systems alongside the team that would go on to build Siri for Apple. An early glimpse of what AI-assisted information access could look like.

Search Era

Cuil - Director of Engineering

Led engineering at Cuil, a web search engine startup that attempted to challenge Google's dominance. Built for scale and learned the hard realities of information retrieval at internet scale.

Scaling Up

BloomReach - Employee #2

Founding Engineer and Head of Operations at BloomReach, a cloud marketing platform. Grew the company from 2 employees to nearly 200, building the engineering and operational infrastructure from the ground up.

2014

The Art of Command Line - goes viral

Published a personal reference guide on GitHub as "The Art of Command Line." It spread rapidly through the engineering community, accumulated over 150,000 stars, and became one of the most-read technical guides in the world.

2016

Viv Labs - Head of Operations, acquired by Samsung

Joined Viv Labs, the AI startup co-founded by Siri's original creators, as Head of Operations and Infrastructure. Samsung acquired the company in 2016, validating the team's vision for a new kind of intelligent assistant platform.

2016 - Present

Holloway - Co-Founded, Now CEO

Co-founded Holloway with Andy Sparks to create a new kind of digital publishing platform - searchable, hyperlinked, expert-reviewed, and updatable. Raised $4.6M in 2019 from NEA, the New York Times Company, and South Park Commons. Published comprehensive guides on equity compensation, technical recruiting, and professional development that have reached millions of readers.

The Holloway Story

Books that update themselves.
PDFs that fight back.

The problem Holloway set out to solve is both obvious and stubborn. Professional knowledge - how to negotiate equity, how to hire engineers, how to run a startup - exists in scattered, incomplete forms. A blog post from 2017. A Twitter thread that got deleted. An expensive consultant. A book that was accurate when published but hasn't been touched since.

Holloway's answer was to build something more like a living document than a published artifact. The platform features custom reader software with search, hyperlinked glossaries, sectional breakdowns, and expert citations. Guides are written by practitioners with actual experience - lawyers, CFOs, hiring managers - and updated as the landscape changes.

The Holloway Guide to Equity Compensation became the platform's breakout hit. It covers everything from stock option basics to secondary markets in exhaustive, practical detail. Over 2 million people have read it. For many startup employees, it's the first place they've ever seen their compensation explained in plain language.

The business model is deliberately clean. No advertising. No user data sold. Holloway charges for access to its most comprehensive guides - the first guide was free; in-depth titles require paid access. It's a publisher that acts like one.

The $4.6M seed round, raised in August 2019, included a notable participant: the New York Times Company. A 170-year-old media institution backing a startup that wants to rebuild publishing from scratch isn't a small signal. NYT has been selective about technology bets. The fact that they participated alongside NEA and South Park Commons suggests Holloway's model resonated with people who understand both journalism and scale.

Holloway at a Glance

Expert knowledge, searchable and alive

Custom reader software with hyperlinked glossaries, search, sectional navigation, and regular updates. No ads. No data sales. Written by practitioners, edited for permanence.

"Most professional knowledge is locked in PDFs and blog posts that nobody can actually find."

- Joshua Levy on Holloway's founding premise

Key Achievements

01

The GitHub Phenomenon

Created one of the top 40 most-starred repositories on GitHub with a document that started as a personal cheatsheet. Over 2 million readers. Approximately 14 community translations.

02

Employee #2 to 200

As founding engineer at BloomReach, Levy built the operational and engineering foundation that allowed the company to scale from 2 to nearly 200 employees. A rare combination of technical depth and organizational thinking.

03

Siri's Extended Family

Worked at SRI International alongside the team that built Siri, then later joined Viv Labs - the Siri co-founders' follow-on company - before Samsung acquired it in 2016.

04

The NYT Bet

The New York Times Company invested in Holloway's $4.6M seed round - a signal that legacy media institutions recognized what Levy was building as a genuine evolution in expert publishing.

05

The Equity Compensation Guide

Co-authored the Holloway Guide to Equity Compensation - now the most widely read plain-language guide to startup equity on the internet, with 2M+ readers and counting.

06

AI-Native Tooling

Currently building next-generation AI tools including Markform (structured Markdown for agents) and Kash, an AI-native shell - extending Holloway's knowledge infrastructure into agent-driven workflows.

Background

Budapest and Berkeley. Then the terminal.

Levy holds a Master of Arts in Mathematics from UC Berkeley. Before that, he attended the Budapest Semesters in Mathematics - an elite program in Hungary that draws students who competed in international math olympiads and aspire to careers in research mathematics. It is not a typical tech founder's starting point.

The trajectory from advanced mathematics to software engineering to publishing isn't as strange as it looks. Mathematicians are trained to find the clean formulation - the statement of a problem that makes the solution visible. Levy has applied that approach to knowledge systems: find the structure underneath the chaos, then surface it for other people.

Richard Feynman - physicist, explainer, and relentless simplifier of the complex - is noted as an inspiration on his GitHub profile. The connection isn't just aesthetic. Feynman was famous for his belief that you don't understand something until you can explain it simply. Levy has built a company around that premise.

Education

University of California, Berkeley

Master of Arts in Mathematics. Advanced study of pure mathematics following an undergraduate foundation.

Budapest Semesters in Mathematics

Advanced Mathematics Program

A prestigious program in Hungary known for attracting top math students globally. Typically populated by Putnam fellows and olympiad competitors.

Inspiration

Richard Feynman

Physicist famous for making complex ideas accessible. Levy cites Feynman's approach to knowledge and explanation as a core influence - the Feynman Technique in practice.

What He's Building Now

Holloway's next chapter: AI-native knowledge

Levy's current work sits at the intersection of AI infrastructure and knowledge management. On GitHub, he's actively developing tools for what he calls "AI-native" workflows - software that treats LLMs not as add-ons but as first-class participants in how humans process information.

Markform is structured Markdown designed for agent workflows - a format that makes it easier for AI systems to read, generate, and act on structured documents. Kash is an AI-native shell, rethinking the command-line experience for a world where language models can assist with every step of a workflow.

Both projects reflect the same instinct that drove Holloway's founding: the tools we use to access and create knowledge are inadequate for what they need to do. The internet didn't fix this. Blogs didn't fix it. PDFs didn't fix it. Now Levy is exploring whether AI can finally change the equation.

At Holloway, the platform has grown to include dozens of expert guides covering technical recruiting, remote work, distributed teams, startup sales, and career development. The company's model - expert knowledge, searchable format, no advertising - has remained consistent even as the content library expanded.

The bet Levy made in 2016 - that people would pay for expert knowledge when it was well-organized and reliable - has held. The New York Times, NEA, and South Park Commons all agreed. Millions of readers confirmed it.

"The internet broke publishing, and someone had to rebuild it. Levy decided not to wait for someone else."

- Profile framing

Six things worth knowing

// 01

His GitHub repo "The Art of Command Line" sits in the top 40 most-starred repositories on all of GitHub - alongside projects from Google, Facebook, and Microsoft.

// 02

He studied at Budapest Semesters in Mathematics - a program that typically attracts international math olympiad competitors and future academic researchers.

// 03

Holloway charges for guides but sells no advertising and collects no user data - a deliberate stance that's increasingly rare in digital media.

// 04

He was employee #2 at BloomReach and helped scale the company to nearly 200 people before joining the original Siri founders at Viv Labs.

// 05

The New York Times Company - a 170-year-old media institution - invested in Holloway's seed round. Traditional publishing backing the startup that wants to replace it.

// 06

His GitHub profile cites Richard Feynman as an inspiration - the physicist famous for the principle that you don't understand something until you can explain it simply.

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Find Joshua Levy online

🌐 Website holloway.com 💻 GitHub @jlevy 💼 LinkedIn jlevy 𝕏 Twitter/X @ojoshe ⭐ Open Source Art of Command Line 📚 Holloway Guide Equity Compensation 📘 Holloway Guide Technical Recruiting 📣 Facebook Holloway Guides