Books that read like the internet. The internet, edited like a book.
Walk into Holloway's corner of the internet and the first thing you notice is what is missing. There is no paywall demanding an email. There is no autoplay video. There is, instead, a table of contents - the kind your high school textbook had, except every line is a link, and every link goes somewhere useful. Hover a term and a definition appears. Click a citation and you land where the editor landed. A reader asked a question in 2021 and the answer is still in the margin in 2026. The book has been updated nine times since you started reading it.
Holloway is a publishing company in the older, stranger sense of the word - which is to say, it cares about sentences. Its founders, Andy Sparks and Joshua Levy, met in 2016 with the same complaint: the internet had broken something about how working people learn. The web democratized writing and, in the same gesture, democratized noise. The result was a generation of founders Googling "term sheet" at 11pm and getting fifteen unsigned Medium posts, four PDFs from 2014, and a thread on Hacker News that ended in an argument about Rust.
So Sparks and Levy did the thing engineers do when annoyed by a market: they built one. Holloway publishes book-length, expert-edited guides on the parts of work that get harder the closer you stand to them - raising venture capital, equity compensation, technical recruiting, remote teams. The guides are searchable to the paragraph. They are annotated by editors. They are updated for the rest of their lives.
Print publishing's first commandment is that a book, once printed, is finished. Holloway disagrees. Tax rules change. Venture terms drift. The right way to interview a senior engineer in 2018 is not the right way to interview one in 2026. A guide that goes stale is, by definition, no longer a guide.
So Holloway built a reader - their word, not a viewer - in which a book is a living document. Editors push corrections the way an engineer pushes a patch. Readers see the changes. The table of contents is searchable. The marginalia is real. A footnote can be a definition, a clarification, an entire essay.
The bet is small and serious: that the future of the business book is less wood pulp, more living text - and that a tiny press with strong opinions can do this better than a large one without them.
Professional learning you can trust.- Holloway, on the homepage
340 pages on every stage of the fundraise, from the first warm intro to the closing wire. The book that made Holloway a verb in a few SF group chats.
Options, RSUs, AMT, 409A. The guide engineers paste into Slack when an offer arrives. Originally an open-source project of Josh Levy's, now a Holloway pillar.
A playbook for the part of building a company that nobody enjoys but everybody pretends to be good at.
The handbook for distributed teams, written by people who actually run them.
The web app the guides live in. Full-text search, hover definitions, annotations, lifetime updates. A book that won't let you lose your place.
Holloway's pitch to outside authors: bring the book, they bring the press. A small alternative to traditional publishing's small advances.
Before Holloway, Sparks built early-stage companies and wrote long compendiums on subjects he wanted to learn - a do-it-yourself encyclopedia approach that turned out to be a business plan. He runs the press the way an editor-in-chief runs a magazine: voice, opinion, taste.
Engineering leader at Cuil, BloomReach and Viv. Author of the open-source Art of the Command Line and Open Guide to Equity Compensation, which collectively reached hundreds of thousands of readers before Holloway formally existed. Quietly proves the thesis works.
Seed: $4.6M, August 2019. Investors include NEA, Comcast Ventures, Precursor Ventures, South Park Commons, RBC, and The New York Times.
React on the front. Salesforce and Help Scout for ops. Segment, Pingdom, Slack, Route 53 in the background. The press of the future runs on a thoroughly modern toolbelt.
About 22, mostly remote. Engineers and editors share the same Slack channels, which is rarer than it should be.
Holloway's chapters and subsections are addressable as individual web pages, which is why Google sometimes ranks a single book passage above a thousand blog posts.
Levy's GitHub-hosted Art of the Command Line collected tens of thousands of stars before Holloway raised a dollar - the readership came first.
The business model is people paying for the guide. Quaint, almost.
Return to the table of contents. The paywall is still missing. The video still does not autoplay. The book is the same book you opened a thousand words ago, except - check the changelog - someone in San Francisco shipped a footnote while you were reading this profile. The book got a little smarter. The internet, for one strange moment, did too.
That is what Holloway sells. It is not a slogan. It is the product.