Introducing The First Holloway Guide

I promise nothing complete; because any human thing supposed to be complete, must for that very reason infallibly be faulty.Herman Melville

It’s an immensely personal day. An exciting day. Two years ago, I made a commitment to spend the next decade of my life working to make practical knowledge more accessible. In February, Joshua Levy and I announced Holloway. A few hours ago, we published our first title: The Holloway Guide to Equity Compensation.

The systems and institutions we all run through can really rule our lives when we’re not given a chance to understand how they work. Knowing the path through and learning to take it slowly requires someone who’s been through it before. They can lead you, and together you make the path easier to navigate, broader and clearer, for the person who comes next.

If they’re lucky enough to find the path.

If you’re lucky enough to meet the person who built it.

And if they’re willing to share it.

Finding the path through something complex often comes down to luck. Some people will always have access to the right path, to better information, by virtue of who they know. Those who don’t should not have to trudge through a forest of search results and news feeds supplied by people and companies who don’t always have our best interests at heart.

Since 2015, Joshua Levy, now my business partner, has run a few experiments to test what would happen if he assembled and distilled the best knowledge on and offline — from published works to people’s practical experience — into a single work and invited others to contribute on GitHub. The Open Guide to Equity Compensation, written with Joe Wallin, was one of them, and it attracted hundreds of thousands of readers, dozens of contributors, and genuinely constructive feedback on Hacker News — no small feat.

We applied everything we learned from those experiments and hundreds of conversations with experts in media, publishing, and technology to start developing a better way to publish long-form reference works. To publish Josh’s original work on Holloway, we expanded the scope, added resources and created interactive visuals, filled in gaps, and drew on the help of veteran lawyers and operators. On top of that, we tailored the first version of Holloway to the idea that each Guide — like everything at Holloway, like everyone — will always be in process. It’s iterative publishing.

We’re doing a lot of the writing on our first few Guides, but we won’t always. Each Guide will be a collaboration between one or two expert authors, experienced contributors, some expert reviewers, and our editorial team. We’ve already started building a community, those who reviewed and contributed to the expansion of this Guide. Now we’re ready for that community to grow. We’re building features to enable Holloway readers to suggest improvements, contribute new sections, call out anything that might be missing, and share practical experience.

Holloway will publish Guides to complex and messy stuff — health, finance, business, technology — stuff that, if you only had a Guide, you could breathe easier, avoid catastrophe, or materially improve your life (or, hey, all three).While it would be a delight to write, The Guide to Drinking Tea might be a ways off. But a Guide to Medicare would make a lot more sense for us to get to work on.

We want to set ourselves up to be here for a long, long time. The way we see it, the best way to do that is to work for you. That means that in the near future, we’re going to ask you to pay us. And that means we’ll have to keep creating work worth paying for. It also means no advertising, no lead-gen for credit cards, no paid links, no nonsense — ever. This first one is free.

I believe you get the future you build. We want the world to be a fairer place. So we’re building a path through complex systems, institutions, and events.The more people who find it and walk it, the broader and clearer it becomes.

Check back. We’ll always be improving, just like you.

Read The Holloway Guide to Equity Compensation now