How to Write a Non-Fiction Book

As a result of writing THE FUZZY AND THE TECHIE this past year, I’ve had the privilege to hear from many friends and colleagues about their own desires to publish a book. Here are a few of the key steps and things I learned along the way. While there are obviously many ways to get from start to finish, this is my journey and story.

The Back Story

With a day job in venture capital, the concept of writing a book evolved, but wasn't something I set out to do. The original impetus was a desire to crystalize my thoughts in a very high-frequency, interactive job. I was meeting half a dozen founders a day, and struggling to pin down where I stood on particular issues, directions, and beliefs. I started writing, first at Forbes and then at Inc. because I wanted a platform to lock in my own thoughts. The process of writing for a public platform served two immediate needs: 1) I had to put in a bit more time and effort to post something publicly than I might have allowed myself on a personal blog I knew no one was reading, and 2) publishing on a respected platform creates the secondary windfall of making your pre-packaged thoughts on an idea appear validated. “What do you think about AI?” Easy, read this piece I wrote. “What do you think about online to offline commerce trends?” No problem, take a look at this article I posted in Forbes last week. It’s a great way to ship your ideas in a tight, validated form-factor. Moreover, it also led to inbound deal flow.

As I wrote, other publications reached out for me to write. I realized that while trying to place a story is hard, publications are content businesses dying for good content. When you flip the equation, you realize that the bottleneck is not the outlet, but the good idea.

In 2013 at a startup dinner in San Francisco I sat at a long table. Most of the attention was directed at a few known people at the table, and so I turned to a quiet gentleman to my left. It turned out he was the author of a NYT best seller. At the end of dinner he handed me his card, introduced me to his literary agent, and it all began. He had already read some of my articles; that gave him sufficient confidence to make the intro.

Literary Agent

When next in New York I scheduled a coffee with the agent at Trident Media, and made my way to her high-up floor just off Madison Square Park. The walls were made of books, and her window perfectly framed the Empire State Building. I felt like I was looking at the real life cover of a Tom Wolfe book. One coffee turned into five. Her assistant kept filling the mugs, and we kept talking, mulling over different trends and ideas. Over the course of half a dozen such meetings over a year, we happened upon a paradigm I really liked. It was “the fuzzy and the techie,” and I immediately knew that was going to be the title of my book. I started picking away at the idea, and the next time I checked the Trident Media Group website, I was on it. There hadn’t been anything formal, no contract, but I’d demonstrated enough conviction, and suddenly there I was, represented by one of the top literary agencies in the book world.

Without having written for Forbes and Inc. and coincidentally meeting a New York Times best selling author at a dinner, the other way I think I would have gone about getting an agent was to pull out 20-30 books in a similar genre to the one I’d try to write. I’d immediately flip to the back “Acknowledgments” section, and write down everyone they thank who’s affiliated to the book world. I’d write down agent’s names, firms, publishers, editors, assistants, etc. I’d look those firms and people up on LinkedIn, and I’d make a spreadsheet of everyone to go after contacting.

Writing A Proposal

For a fiction book, you write the manuscript. You make it as perfect as you can, and then you hope that literary agents and publishers give it more than a quick skim. For non-fiction, the process parallels my world of startups and venture capital. The publisher wants to see a book proposal, not a first draft of your ideas. The proposal eluded me for months. I wrote 100 pages of what I thought was the book, only to scrap nearly every page of it. I had a call with a retired publisher from Random House, and she gave me the basic bones of an outline for what I needed to pull together:

• Abstract (half a page)
• Bio of me and my "platform" (one page)
• List of potential blurbs / important people you can access (one page)
• Short outline (one page)
• Narrative outline (3-4 pages per chapter on people to interview, ideas, studies, etc.)
• (For 8 chapters, this was about 30 pages for me)
• Sample Excerpt (10-15 pages)

In total, my proposal was 40-50 pages. This wasn’t 50-pages of the book, but this was a very specific framing of my ideas, structuring, outline, and whom I might feature in each and every chapter. The sample excerpt was about the only 15-page block out of the one hundred pages on the floor that proved to be somewhat useful in my book proposal.

To test the waters on my proposal, and because I was also under the age limit of 35, I also submitted my book proposal to the Financial Times and McKinsey & Company's Bracken Bower Prize competition. The prize is offered for the best business book proposal of the year for an author under the age of 35. I submitted mine, and in 2016 it was long-listed, then short-listed, then named a Finalist for the Bracken Bower Prize. This platform offered me an incredible stamp of international validation for the idea, and further impetus for my agent and future publisher to stand behind the ideas.

My agent believed that my proposal was finally ready. This process took me one year. I wrote the proposal over and over, refined it, edited, deleted, etc. Finally we sat down over lunch, and ironed out final chapter titles before sending it off to editors.

Pitching Publishers

My agent sent my book proposal to about a dozen editors of very specific imprints. Imprints are the names on the spines of books, names like “Portfolio.” You don’t know until you get into the book world, but “Portfolio,” is for example, the business imprint of Penguin Random House. There are only five or six main US publishing houses, and nearly all of the book brands you see are various imprints of those houses. One is for fiction, another for academic books. One is for business, and another for mass-market trade non-fiction. We received word from a number of publishing houses that they wanted to meet . Within two weeks of sending out the book proposal I was in a number of different New York publishing boardrooms, books stacked all around me, defending why my idea was worth pursuing. This process exactly paralleled my world of startups and venture capital, except I was on the other side. My agent “ran an auction,” meaning they ask for the top bid of each publisher. The process is “blind,” so no publisher knows what any other publisher is bidding. The bid is your “advance,” or the advance payment you receive against which your future royalties first deduct. Within two weeks of pitching publishers, I had a book deal with Houghton Mifflin Harcourt. While the contract was in negotiation for months, and I didn’t receive my first (of three) advance payments for a few months thereafter, I began writing the book the very next day.

The Manuscript

Once you get a book deal, the clock starts. You have a due date for the book, and the second third of your advance is usually tied to the “delivery and acceptance” of your manuscript. In other words, if you never get it done, or they don’t like it, your book doesn’t happen. Moreover, you might be obligated to give back the first third of your advance. In venture terms, the publisher has a “full ratchet.” You might write a chapter or a section at a time, or you might write the whole book and submit all at once. If you miss your deadlines, your chariot becomes a pumpkin, and all of the obligations in the contract become options. The book might happen, but it no longer has to.

For non-fiction, 60,000-75,000 words is a standard length for something meaty enough to want to buy, but not so much that you won’t pick it up in an airport. Page length is a function of typography and spacing, margins and design. Whether it’s 225 or 300 pages, chances are the word count is fairly similar, but the buffering has happened in the font.

The Writing Process

Most people think the process of writing a book means getting to run around, not chained to a desk. While there is certainly the allure of long train rides and interviews with interesting people, a schedule that is what you make of it, what’s also true is you have to grind out words on a page. However you do that. For me, and for many, this is more of a "groundhog’s day" approach than one of excitement. I went to the same Brooklyn café at 8am for about 50 days straight through the bulk of the writing. I went before breakfast, when I was hungry and had only one black coffee to drive me. I went without my laptop charger, so the clock was ticking on my morning productivity.

For a work of non-fiction, chances are you have interviews, which require scheduling. Tools like Calendly can help with scheduling. Tools like Pocket can help you keep track of articles and trends. Tools like Rev can help you transcribe from audio to text, and IFTTT and Zapier can help automate processes such as saving items to Dropbox.

The process is therefore less simple than just writing. It’s figuring out the structure of the book, outlining it, doing research enough to consider who might be a good interview or person to illustrate a concept, and then coordinating to get in touch with them, read their work, listen to various podcasts that have perhaps featured them, etc. Therefore for non-fiction I found the process to be a few different phases, which I’d block and tackle at different times of the day, and in different physical spaces or cafes:

1.    Basic book structuring

2.    Pre-research to fill in rough sketch of who to profile where

3.    Coordination of interviews, learning about stories

4.    Transcribing interviews into notes (often using Rev's tool)

5.    Writing narrative from notes

6.    Narrative blocking of stories and studies, finding voice and flow

7.    Re-structuring in Scrivener

8.    Polishing

Some aspects of this process are very straight forward, for example, schedule interviews, conduct interviews, transcribe notes, and flesh out narrative from the notes. Once you have narrative sections, these help psychologically, as you’ll have word count. You’ll have a lot of content about interesting people who are fun to write about. Let’s say you conduct 20 interviews, and you can flesh your notes out into five pages on each subject. You already have 100 pages of content, and are well on your way at 25,000-30,000 words. You're already roughly a third of the way done.

Next you need to find a balance and flow between stories and research, or studies that back up some of the narratives, and help weave them together. For this process I found a Google spreadsheet to keep track of concepts for each chapter to be helpful. For each concept, I would write out a one-page summary of the idea. Let’s say you have 6-8 concepts for each chapter, and you have 2-3 stories, if you add that up it’s 6-8 pages of research (one page per concept), and it's 10-15 pages of narrative (2-3 stories). Suddenly you have on the order of 20 pages, which is almost a full chapter (20-25 pages).

At this point, as you have these big blocks, and little blocks, a tool like Scrivener becomes very useful to be able to move around your narrative blocks without cutting and pasting long sections into and out of Microsoft Word. The longer your book, the more terrible Word can be. Scrivener gives you a folder view that allows you to nest these blocks within folders, which you can create for each chapter in your book.

If you’re targeting 75,000 words for your book, plan on writing more. At one point I had 110,000 words imported into Scrivener, but this is because I had too many stories. I cut it down to 60,000 words, and then beefed up the word count by adding more research and analysis. Ultimately I turned in around 80,000, which we cut down to around 75,000. There’s no right mix of narrative and research, but you can think of these in some ways as your gas and break pedals in the flow of the read in your book.

Editorial Process

Once you “deliver” your manuscript, and it is accepted, this is the juncture for payment of the second third of the book advance. The third is on final publication of the book. Once delivered and accepted, the book enters the editorial phase. In this phase you’ll likely receive structural feedback, which hopefully is light, if you’ve given chapters one at a time, and gotten good feedback from your editor along the way. Editorial will touch content choices, stories, perhaps length of stories, and the mixing of narrative blocks.

Once the structure of the book is complete and finalized, the manuscript will be sent to copy edit. Copyediting means consistency of voice, and some basic stylistic choices such as when numbers should be written out versus put into numeric format. Each publishing house likely has its own stylistic choices around whether book names are italicized or whether to refer to characters by last name only, such as in a formal publication. Choices also relate to the notes section of the book, if there are to be superscripts or not, if notes are to be footnotes, or endnotes, and how detailed they are.

After copy edits are done the book goes “to production.” In this phase the book is laid out as it might be in the final version of the book. The margins and typeface are set, the chapter spacing laid out, and the final page count for the book considered. The first pages are a PDF version of what your final book will look like. There is still time to tweak small sections, add in a line, or edit another out, but the book takes its form.

Finally, the first pages take shape, and the index is confirmed. As the index refers to the text, and the text has been moving around until this point, pinning down the index is the final step to pinning down the text as it will appear and be laid out in the final book.

The book is printed as a “Galley” or an “ARC” (advanced reading copy), and those are distributed out to long-lead journalists and publications. A couple dozen are also probably reserved for the author to send out to solicit “blurbs” from various people. Blurbs are the “advanced praise” for the book, typically from notable industry figures. I hand embossed and wrote 50 such letters for potential blurbs, and received 10 back. These early endorsements can help catalyze press, or other interest in the book.

About a month before the “pub date,” or publication, you should receive the hard copies of your very own book. I received 30 copies, and it’s a pretty surreal moment. Most of your friends will ask for one; most of your good friends will already have bought two.