A Tech Bro Walks Into a Publisher: 13 things I learned from writing a book
becoming a better writer one Scorsese movie at a time
(A slight detour this week: the last two years I’ve gone deep into how publishing works. That’s because I just put out my debut, The Billionaire’s Folly, about working for the co-founder of Ethereum for three years at an experimental startup run amok. Get it on Amazon or help me out with an upvote on Reedsy!)
Are books dead?
We’ve read such fearful headlines since the Harry Potter series ended. What’s fascinating is that we read more than ever - text is the universal interface, roon writes - yet bookstores are closing everywhere we look.
And from what I learned the last two years, it’s bad and likely to get a lot worse. The industry is too slow, and too data-deprived, and too easily gamed to avoid a death spiral that forces publishers to rely on celebrity over quality.
But don’t take my word for it - listen to the Big Five CEOs who are desperate to merge with each other, arguing “they had no idea what they were doing with all their money.” The only hope is that we might already be at the bottom.
But there were a lot of positives too - including priceless tips my agent gave me on becoming a better writer.
The numbers are pretty ugly
An author recently wrote on Twitter that half of all publishers’ books sell only a dozen copies. An eye-catching claim!
But others were quick to correct the numbers as not that terrible - but even so, for around 45k books from the top 10 publishers, a huge number are losers. Around 94% sold fewer than 10,000 copies, which is generally “breakeven” for a book. The average book sells around 5,000, but that’s because of a few runaway bestsellers - the rest do under 2,000, a major loss.
Some data scientists tried to come up with methods for predicting publishing success, with some accuracy. Unfortunately, the best metrics were the author’s “visibility” (using traffic to their Wikipedia page) and previous sales - meaning it’s still hard to predict first-time authors, especially non-celebrities.
Interestingly, the prestige of the publishing house itself also mattered a lot, but that’s a data conundrum - like Ivy League colleges, is it that they foster success because of their quality or because they get the cream of the crop? Most evidence for college at least points to the latter.
The most predictable winners were biographies of famous people, like A Promised Land by Barack Obama. For the rest of the list, it basically comes down to chance - which many publishers can barely afford.
Partly because books can’t compete with viral videos
Books don’t have many features. Unlike photos from your trip to Rome, there’s no “share” button below that beautiful ragu. If you want to share a good quote with your friends, copy-pasting (even from a digital reader) to tweet or share on Instagram is a lot more work than sharing that dancing cat video.
That lack of virality means books really are reliant on word of mouth. That’s hard - and often random.
In fact, my agent at one point said, “If you just had 10,000 Twitter followers, this would be a slam dunk to sell.” Publishers need the author to have platform, and that’s why so many books nowadays are by celebrities.
But even that isn’t working. The NYT notes that a publisher paid Billie Eilish $1 million for her memoir - but with 100 million Instagram fans, she could only sell 64,000 books (.064%!). That seems like a lot, but at $5-10 in revenue per copy, the publisher may have lost as much as half a million dollars without marketing costs.
Publishers badly need a few books to become home runs (Harry Potter!) - but they have no idea how outside of a few tested genres. Twitter and Instagram followings are a proxy for popularity, but those platforms can be fickle, as a book-related post itself needs engagement to get any visibility.
The other benefit of platform is it takes a pay-to-play element. When I worked with big-time agents, they showed me proposals of business books by CEOs or professors - who often guaranteed that they would buy 5,000 copies for all their stores, or would assign it to their large classes to guarantee some sales.
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…but also because publishing is stuck in the last century…
Another reason publishing is dying is because it is stuck in a 20th century model that values text and relationships. (Of course a tech guy would say that, right?)
But let’s take a look. For a publisher to even consider your book, you need a literary agent. They say pitch 70 agents before you give up.
Agents determine their “niche” mostly based on taste. That means they pick up books on a mix of their personal passion and commercial expectations. There’s nothing stopping a huge imbalance of agents being interested in nautical memoirs, even if that’s very niche. When I was looking for an agent interested in “tech,” I found agents interested in AI, or dystopian sci-fi, or dry explainers, or CEO tell-alls, but only 2-3 wanted startup stories. Then I had to hope they might see my email amidst the 20 pitches they get a day.
Agents are also data-deprived. Their assessment of the market is based on last year’s sales numbers. That’s why 2022 saw a surge in “startup failure” stories - WeWorks, Theranos, Uber - even when these happened 3 or more years ago. They are not scanning their inbox based on Google Trends, real-time sales numbers, or other analytics.
They do look at BookScan, the one data source available, but the numbers aren’t the most accurate - it only covers 75% of physical retail locations, and it can be difficult to assess the numbers when there are multiple editions or audiobooks, etc.
Instead, like journalists, literary agents and publishers spend a lot of time on #booktwitter to keep up with trends. But Twitter is a terrible platform to track “everyday” tastes, skewing their data further.
Agents also work on a ~15% commission. That means they are strongly disincentivized against taking risks - they might only make $5,000 off a new author with potential versus $150,000 for another Trump tell-all. That was a deep irony for me to learn - publishing, a mostly progressive industry full of idealists, runs on cutthroat economics that basically relies on passionate agents taking on a ton of the work for a small cut.
That’s why as I got close to pitching my 70th agent I almost gave up…until the 67th, and 68th, both replied at once. Like I said, a lot of it is random!
How does anyone make money? Luckily, Netflix is flush with cash to option any exciting story in sight. The promise of content becoming content helps. There’s also a burgeoning industry to support those dreaming to write a book - agents consulting, pay to play blogs, and “marketing” support (often paid courses
…though agents are amazing
This silly structure is not agents’ fault - they’re working within the system. And many are amazing!
I was incredibly lucky that I got to work with not one but three top notch agents. (It’s actually kind of preposterous given the joint probability of finding an agent is usually the rate-limiting step.)
All three - Caitlin, Bill, Esmond - have an incredible sense of telling a story. My first drafts were like attending a “boring meeting” according to them, and they knew exactly how to change that. They taught me how to make a simple Uber ride feel like an adventure scene from an action movie.
The most impressive part is that nothing about my story changed - it is still mostly verbatim dialogue from my life and a precise timeline of that era. But they taught me the way to tell the story, to turn my humdrum consulting job into an Alice in Wonderland story, just with the power of narrative.
And sadly, two of them made no money for literally months of work.
Empathy sells - that’s good and terrible
The first thing my agents told me was that empathy sells. My first drafts contained nothing about me personally, so that’s where we spent the most time.
But take a stroll through LinkedIn to see the terrible results of that strategy. Everyone is pouring their heart out for likes - to boost their digital marketing reach. And yet it works in going viral, time after time.
On one hand, it’s a good thing empathy still works to bind us all together. But in a world bursting with content, the competition for eyeballs has rendered most of the Internet into a desert for any real authenticity.
Make the archetypes your own
One funny thing I did to help with writer’s block was watch a lot of movies. Martin Scorsese movies, in particular. In the first two minutes with any character he hammers home a key trait that really makes their personality stand out. That brevity and uniqueness keeps the audience’s attention.
Making experiences seem relatable - a crappy boss, a stressed friend - without being cringe or formulaic is the hard part. Observing my friends helped. Even “normal” seeming friends will have enough quirks - an unusual catchphrase, a notable hobby - to seem totally weird on close enough observation.
There’s a lot more time than you think
Honestly, it’s hard to write on Substack once a month on top of a job, which makes me wonder how I finished 250 pages. We’re trained to waste a lot of “interstitial moments” - waiting for the elevator, deep in the subway - with endless scrolling. Looking back, I was passionate enough about the project to keep finding ways to juice each one of those.
I used to keep a dozen iPhone notes with thoughts for scenes and dialogue. Long drives became time for mental drafts, and long flights became time to bang out every word I could on the keyboard. Writing is a great hobby since it can be done anywhere, but there’s not many pastimes, whether design or even sports, that can’t be game-planned with pen and paper.
Writing is good for your thinking (and career)...
Aside from telling my story, the book was a great exercise for me to tease out some thoughts that I’d never really been able to make sense of.
Did I think technology was good for society in the long run? Believe it or not, Henry David Thoreau is one of my favorite authors - the guy who said we should all live in the woods by ourselves. I hate staring at screens. The problem was, I had to give the reader a story that made sense, and that meant a logical conclusion for what I thought about crypto. (You’ll have to read the book to find out!)
Sharpening my ability to tell a story also helped me a ton with presentations and interviews. As a Product Manager, you have to convince people your feature idea is the future. What better way than to weave a story around it?
…but bad for your mental health
You know that little voice inside your head that narrates your day? The one that thinks ah, should have said that instead while recalling your latest debate with your spouse or boss?
Well, writing is a great way to give that voice a megaphone. Whatever circuits in there you use for accessing words are strengthened infinitely by doing that all day, and it doesn’t go away when you put down your proverbial pen.
I think part of the reason COVID was tough on people was we became a very textual society - emails, text messages, tweets. It’s the (mentally) quiet moments where we recollect ourselves.
If anything, the hours you are forced to spend alone writing make that effect compound - you are flexing these social muscles (communication/speaking), but with no one responding. While I’m lucky, it’s an understated risk, and now I see why so many writers historically have been depressed.
Omit needless words
For the fans of Strunk and White. My book was originally 320 pages, which means I cut over 60 pages - 20%! - from what I thought was the final draft.
I write terrible, wordy first drafts. Splatter the page with every idea you could ever think. But in final form, a subject and verb are often all you need (“My boss exploded”).
Make your own luck
It sounds really cheesy, but there were many, many times I gave up on this project - finishing writing, finding an agent, redrafts - and some bizarre, lucky break kept me in.
Like Jack Dorsey tweeting my blog. Or that my 67th agent pitch got a reply after months of silence. Or that Bitcoin was up $10,000 the week I pitched that agent. I don’t have much to say, other than that it was weird.
But I also was hacking my way all along. I knew Jack Dorsey hated web3. I even A/B tested different spellings of my name (that’s where Fais comes from) to see if it got better responses (it did). So I was using my inside knowledge and data-driven approaches all along.
Time is friend and enemy
My takeaway is actually it is neither skill nor luck. It was the fact that I spent so much time on the project that gave me the best chance.
I don’t know if it’s good advice. If time is your ally, it’s also your enemy - we can only take so many big swings that take years and years. What passion projects are worth it?
That’s also the problem with books. It takes 1-2 years even for fast writers to finish, and weeks to months for editors and then the audience to read. Bayesian statistics basically tells us the more frequently we can update our data, the more accurate we’ll be ultimately.
Publishing is up against other information industries - podcasts, Substacks, TikTok - that can get feedback, iterate, and adjust to changing tastes. That frequency means better honed content and fewer wasted words. Each book we buy and never finish reading conditions us to reconsider our next purchase a little more.
The last big publishers trying to merge could give them the chance to invest more in taking risks on new authors and genres - or it could result in them monopolizing all the likely hits and killing the rest of the industry.
In my view, it’ll take new models - serialized stories, more digitally interactive writing, better research - if the status quo for publishing is going to get better, if it does at all.
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