Writer (Definitions)

San Francisco, CA
About Us

Holloway is a new publishing and technology company in San Francisco that publishes comprehensive, practical Guides researched, written, and refined by experts. Our first Guide, The Holloway Guide to Equity Compensation, is now one of the most trusted resources on the web for navigating the swamp of challenges related to equity-based compensation.

We’re a six-person team with deep experience in writing, machine learning, and search that believes we can create a world where access to existing knowledge isn't a barrier to making progress in our careers.

We are seeking a freelance lexicographer to create, improve, and iterate on our growing library of definitions and their associated editorial guidelines. We currently have a small but rapidly growing set of definitions associated with our Guides, one of which you can see here. Our titles and our product are created by experts and designed to improve with community contribution over time—you can find our Editorial Principles here


    • Write definitions of technical business and finance terms from scratch
    • Improve a small set (<200) of existing definitions
    • Source new terms to define
    • Complete competitive analysis of other content online (as appropriate)
    • Assist in refining our guidelines for writing definitions as needed


    • Detailed business and finance knowledge: You have broad knowledge of business and finance, with depth in one or more areas, such as startups, investment banking, or venture capital. When needed, you can get your head around the subtle nuances of AMT and stock options, or the terms of convertible note.
    • Great at research: You can easily research, consume, and reconcile all kinds of information on the web. You track sources of facts and figures to see if they’re trustworthy.
    • Rigorous writing abilities: You love language and have the ability to write with precision, rigor, and clarity. Technical nuances of language matter to you. You also prefer direct language over opaque or highly academic writing. Have written material with a high need for accuracy before.
    • Self-awareness: You're comfortable with "knowing what you don't know." When you don't know something, you have a knack for finding expert or primary sources to fill in the gaps, and discussing and reconciling conflicting viewpoints with them.
    • Strong logical and analytical skills: You hate misleading statements, sloppy thinking, circular reasoning, logical fallacies, and other abominations.
    • Attention to detail: You can systematically apply (and update) guidelines for high quality.
The Holloway Story

Holloway started with two people: Andy Sparks and Josh Levy. Andy left his last company fascinated by one question, "What are all the questions Google doesn't provide a good answer for?" Josh, inspired by Doug Engelbart's theory of "intelligence augmentation (or IA)" not "artificial intelligence (AI)" wanted to create a place to share and collaborate on deeply practical knowledge.The two got together in early 2017 with a shared commitment to spend at least ten years working on creating a company that would make it easy for everyone to find the best knowledge, you know, the stuff the top 1% of people in a field know.

Many of the ideas for Holloway came from open source experiments Josh ran on GitHub from 2015-2016. First, he publishedThe Art of the Command Line, which would go on to see more than 800K visitors. Second, he publishedThe Open Guide to Equity Compensation, in the fall of 2015, a collaboration between Josh and several startup lawyers. Third, he publishedThe Open Guide to Amazon Web Services (AWS) in the summer of 2016. The latter two each saw hundreds of thousands of visitors to the GitHub README page and hundreds of contributors.

Andy, on the other hand, had just left a company he co-founded, Mattermark, had spent months researching the clean water industry, and kept finding the best knowledge on clean water wasn't showing up in Google searches, but instead through conversations with venture capitalists he knew from Mattermark. What if the knowledge these experts knew was widely available? What would the world look like then? To test whether people would care, he began exploring publishing collections of knowledge on specific subjects for others to learn from such as "Everything You Should Know About CRISPR—And Where to Learn More."

Shortly thereafter, a mutual friend put two and two together and introduced Andy and Josh. The two spent months learning about each other and reconciling their differing ideas, and decided to join forces in February of 2017