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Publishing Startups and the Great Fuzziness

Startups are strange little things


Content Magazine recently published an essay of mine, β€œOur New Shrines.” Take a peek. It’s a fun little thing …

Back? Weird, right? It’s unusual. But the circumstances that led me to think about Facebook from a publisher’s perspective have been unusual. So I thought I’d go into that a bit here …


In February of this year I found out I was one of twenty individuals chosen as a TechFellow. The TechFellow awards is a grant that you’re asked to use to invest in startups. No strings attached.

I’ve always tried to live lean, and so outside of slowly building my small portfolio of publicly traded tech stocks,1 the idea of investing in early stage companies never crossed my mind; I simply never had latent capital sitting around to do such a thing.

Money dropping out of the sky β€” earmarked for investing β€” changes that pretty quickly. So, grant in hand, I decided to embrace this as an unexpected chance to learn to think more critically about startups from the outside.

#Books, of course

Over the last decade I’ve engaged books and publishing on almost every level β€” from physical production and distribution, to working with printers and coaching authors, to international and domestic (US) sales. I’ve been involved as an author, a producer, a designer, a technologist, a cheerleader. I’ve organized events and helped build online communities. And all of that was just for β€˜classic’ books.

I’ve spent the last four years digging into the digital side of books and publishing. From essays, to Kickstarter projects (to essays about Kickstarter projects), to product design on a startup team. I’ve tried to make a point of doing.


Naturally, when I began to look for startup investments, my focus was squarely on books and publishing (and, tangentially, education) related companies.

In the searches and meetings that have emerged over these past few months, I find myself drawing on all of the above β€” from a holistic theory of physical book production, to an empathy born from authorship, to the understanding of digital product design.

Startups β€” books and publishing startups inclusive β€” are mostly small groups of motivated people trying to give shape and form to ideas yet actualized.2

What if everyone in the world had access to every book in the world?
How does that access change engagement?
How does it change business models?
What does it mean to read ‘socially’?
How do publishers and authors modify their behavior when distance to readers is zero?

Lurking behind all of these questions are even more atomic questions about tools. It’s necessary to question all of our tools. Almost every publishing focused writing, editing or design tool we use today was born in an age of unnetworked physicality. Will Adobe have a place in the future of digital publishing? Probably. Will InDesign be the end-all-be-all of digital publishing? Probably not.

How much of the old do we throw out to find the new?

All of the above are the sorts of questions publishing startups ask themselves. We don’t know the full answers because the platforms upon which answers may lie have yet to be built. And it’s hard to tell what other more interesting questions will emerge by tackling some of these more obvious questions. Sometimes seemingly boring questions lead to utterly fascinating ones.

#Fuzzy logic

In my head, I call all of this the great fuzziness.

The process of assessing or mentoring a publishing startup feels like looking at a pool of abstraction through the lens of a decade of doing. Book doing, in my case. There’s a balance you need to strike between total open-mindedness (because sometimes your experience blocks your ability to see) and framing the questions within the context of all of your experience (because sometimes your experiences helps skip unnecessarily circuitous routes).

The end goal in all of this being: help the great fuzziness coalesce into useful, sustainable, cogent things. Hopefully things that make books and publishing more pleasureful, engaging, sustainable, and, generally, socially better (which is, admittedly, a difficult thing to quantify).

Finally, one hopes books are more accessible β€” not less β€” because of technology.

#Mountain views

The shift from an engaged making and doing into a more meditative, high-level space has been β€” so far β€” a deeply fun and satisfying adventure. Thinking about startups from a macro-level is, unsurprisingly, unlike working on a single product. It’s given me an entirely different kind of empathy for companies raising money and investors contributing money. And I count anything that increases empathy as something valuable.

So it is I came to write, β€œOur New Shrines.” Already β€” even from just a few months of conversations around this domain β€” I find myself questioning the how and why we publish as we do, as we have. A year ago I wouldn’t have pegged Facebook as a viable platform to start a publishing enterprise. Now, I recognize there’s a subset of content creators that are crazy not to start with Facebook.

  1. I was a stock market geek back when I was 15. I used to give myself budgets and track fantasy investments. Let’s just say I was a weird kid. The end result is that I’ve cultivated the habit of buying small chunks of stock of companies I love, incrementally, over the past decade and a half. ↩︎

  2. For more lengthy thoughts on what a startup is, exactly, see: Steve Blank’s “What’s a Startup?” or Paul Graham’s “Why Startup Hubs Work” ↩︎

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