Holloway

Story

No one wanted to leave.

When Andy Sparks and Josh Levy met in 2016, they had both been trying to tackle the same problem: What would happen if more people had access to expert knowledge? It ended up being a conversation they wanted to keep having for years.

Josh, formerly director of engineering at Cuil, a founding engineer at BloomReach, and head of operations at Viv, brings more than 10 years of experience building and scaling engineering teams at startups. Inspired by Doug Engelbart’s theory of intelligence augmentation, he wanted to create a place to share and collaborate on deeply practical information. He had been working on open source projects, publishing The Art of the Command Line, which saw 800K readers, The Open Guide to Equity Compensation, and The Open Guide to Amazon Web Services (AWS), which received hundreds of contributions and saw hundreds of thousands of readers. He wanted to learn how to scale up these efforts and figure out how to help people have a better learning experience online.

Andy, on the other hand, had just left Mattermark, a company he’d cofounded, and was ready for something new. He wanted to work on a project relating to clean water, and spent months researching clean water companies, initiatives, and technologies. But his extensive internet research on the topic wasn’t yielding helpful results or the guidance he really needed. He realized there was an even more fundamental problem at stake: how to make expert knowledge more widely available to those who wanted to tackle big problems. Andy wasn’t going to create a clean water company that would change the world. But he knew a lot about business. So instead, he would help the next person who came along to try. He started by publishing collections of knowledge on specific subjects for others to learn from, like his compendium, Everything You Should Know About CRISPR—And Where to Learn More.

Together, Josh and Andy knew that they wanted to build something that would help people tackle the challenges of modern work better, faster, and smarter, with fewer years of failure, fewer wasted dollars, and a lot less pain. They spent a couple of months learning about each other, challenging each other’s ideas, and reconciling their differences, using this framework to determine whether they should work together. Taking it slow and moving carefully forward, they developed a basis for the idea that would become Holloway, inspired in part by a mutual love of the work of physicist Richard Feynman: understanding from first principles was the best way to innovate practices and systems, and improve the world.

Bill Waterson put it best: “The truth is, most of us discover where we are heading when we arrive.” Holloway is still arriving. We’re now six core team members, split between engineering mavericks and editorial mavens, with a few close and dear collaborators working to help us develop our content and product.

What we know for sure is, wherever we arrive, we want to stay there as long as we can.