Writing and Startups

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About a year ago, I became a full-time writer. The great master plan was -

  1. Build a content agency
  2. Write fiction novels
  3. ???
  4. Profit

To be honest, I never planned beyond step two. The idea of making a living by building fantasy worlds seemed, well, fantastical. There was this nagging thought in my head that things wouldn’t work, people wouldn’t like the book, and somehow, my life would fall apart if I failed.

So I did what any rational person would do, I went all-in and hoped for the best. With another writer, RC, we asked our clients to transition to per-piece pricing and started writing our first fiction book.

It failed.

But the world didn’t crash down. We learned what we could from the failure and started a second book called Deadworld Isekai in July. This new book found near-immediate traction, gathering over 5k readers in a matter of weeks.

Publishers started reaching out to us in August and after countless Zoom calls, we signed with one of the largest publishing companies in the genre in October.

I’m still pinching myself at how quickly everything happened. When I think back to our journey, we got a lot of things wrong. And we made some pretty big stumbles. But we also got a few really important things right.

Two is better than one

In some ways, writing a novel is a bit like building a startup. Most startups don’t fail because they run out of money. Instead, at some point, they slow down and stop being able to belt out high-quality shots on goal. [1]

Writing a novel is a bit of the same. People generally start with a bunch of great ideas for their story and as they write, motivation slowly drains out of them. Writing is demoralizing, it’s tough, and it’s even worse when at the end of everything, only a handful of people read the story. A writer never runs out of words, they just run out of courage to transfer those words from their ideas to paper.

So as long as people have been writing, they’ve found support in having someone at the other end who can say, “hey, this wasn’t so bad. It’s all in your head. What do you think about this?”

For most authors, that person is their spouse or agent. In a content agency, it’s the relationship between the writer and the editor. In startups, it’s often the technical writer working with the engineer or PM.

Here, I want to emphasize how important morale is to writing. Most people are inspiration writers. What that means is that they sit down one day and write a couple hundred words. Then they go off into their lives and don’t come back to the writing until weeks or even months later. I used to be one of those people.

At first, I thought it was because there was some background process running in my head that was working out the sentences so that when I did sit down, the words would flow out of me like water. But when I started writing professionally, I realized that the words were always there, I just built a dam to stop them because I was afraid of writing something that wasn’t up to some imaginary standard.

The two-person writing team is more than just two people writing a single story, it’s the best way that I’ve found to write seriously without burning out.

Specialize, specialize, and then specialize some more

I wasn’t kidding about specialization. Our first book, Deadworld Isekai, falls squarely in the Young Adult Fantasy genre. The best way to we’re doing is that we’re filling the gap between really young adult like Harry Potter and more serious fiction like Moby Dick or Dune.

Now, going even deeper, within the fantasy genre, our book is an Isekai LitRPG. Isekai is a Japanese term that means “another world,” and stories in the genre have the premise of a protagonist being sent to another world after dying in the modern, today world. LitRPG is a bit more simple, the stories add game elements such as stat screens and skills to the character.

If you think that this is getting really niche, you’re not wrong. Both the Isekai and LitRPG genre are incredibly niche, and yet, it’s big enough to support dozens, if not hundreds, of authors making seven figures or more a year.

Startups want to be playing in a market of one. A new fintech company doesn’t want to compete head-to-head with Visa, they want to find a specific underserved customer demographic, and grow from there.

The other side of specialization is knowledge. Both RC and I have read a lot in the specific young adult fantasy genre that we write in. You could probably measure it in terms of man-months or even man-years. As a result, when we started writing, we had a vague intuition of where to start finding initial readers, what the bar for quality looked like, and why some books succeeded while other books failed. While it wasn’t a silver bullet for success, it did mean that we weren’t fishing in the dark.

Now, if instead of picking young adult fantasy, we chose to write in women’s romance fiction, life would have looked pretty different. Although the market for romance is far bigger than fantasy, we’d have to start by reading the books by Colleen Hoover, Barbara Davis, and Emily Henry [2]. To use game terminology, we needed to understand the meta before we could start playing.

There’s a lot of valid advice on which genre to pick and how to write for a specific market. My take is to simply pick one that you like and go deep, spend time in it, and write seriously. At the end of the day, while romance is a different beast than fantasy, they’re all fiction. And the core of fiction are emotions, values, and beliefs.

Quantity over quality

A startup that only tries a single idea is likely to fail. A startup that tries dozens to even hundreds of ideas (without getting stuck in pivot hell) is much more likely to succeed.

The same thing applies to books.

Every year, thousands if not millions of books are published. Most of them don’t see more than 25 readers.

Naturally, the conclusion most people come to is that if a writer writes a book that’s super high quality and amazing, then it’ll cut through the noise and succeed. And every year, new writers will write a chapter, decide that it could be better, spend a few days rewriting it, and then fiddle around with it over the course of the next few months. Then, when they release their book after years of work, it doesn’t take and despair starts to set in.

Unfortunately, quality is not the metric best correlated with success in the writing world.

The name of the game is quantity. The only way to cut through the noise is more words, which leads to more books, which draws in more readers, and the law of big numbers means if the book is good enough, you can drown the writers focusing purely on quality.

That’s pretty much what we did. We started at a pace of 12-18k words per week, and we now write anywhere from 20-40k words per week. Per day, that’s around 4-8k words per day.

That’s not to say the secret to success is writing novels at the fastest pace known to man and disregard plot or character development. Rather, it’s to say that writing should be treated like work, serious work. Scientists don’t go into the lab on the days that inspiration hits them, writing is no different. It’s daily, continuous work.

At a higher level, the quality of a piece of writing has two parts. Quantifiable stuff like scenes, plot, prose, structure, and word count. And then intangible stuff like characters, memorable quotes, and pacing.

It’s really hard for a single person to keep all of those things in mind while writing. This is where having two people working on the same project makes a big difference. In our first book, RC and I tried different combinations of writing together, in part to understand who should tackle which parts of the writing puzzle. We tried 1-2-1, I write, he edits, I proofread, and also 1-2-2-1, I outline, he writes, he edits, I proofread.

When our first story failed, we had a couple of theories. Maybe the base story idea that I had come up with wasn’t very good to begin with, or maybe RC was ill-suited to write the story because it wasn’t his idea. But one thing we knew for sure was that we needed to change how we collaborated together.

For our second book, we settled on 2-1. He writes in 4-8k word chunks and I edit, often cutting out anywhere from 200 to 1,000 words. I think it’s working pretty well.

In general, quantity is thought of as the opposite to quality. But the reality is that the two are actually complements. No writer creates a perfect first draft. But the second draft inches a bit closer to being good. And the third draft is where the story starts to shine through and develop a life of its own.

Post online and have thick skin

The traditional publishing industry measures itself in books. A writer spends months to years perfecting a book, publishes it, and then does it all over again. On average, this cycle takes about a year.

Posting online is measured in terms of chapters. It takes a day, maybe two, to write a chapter, edit it, and hit publish. In doing so, as an author, you can gather readers and improve the craft of writing at a rate far quicker than with the traditional publishing model.

In some cases, readers will say, “The characters all feel completely real. They may be flawed, but they’re internally consistent and never feel like their choices are being forced for the sake of the plot.” And as the writer/editor, we feel a tap-dance of joy.

Looking at the stats, we saw what readers really resonated with (shovel fighting, protective authority figure) and where the reader immersion was broken (too many coincidences too quickly). With the data, we knew which parts to lean into and which devices to avoid in future chapters.

But, there’s no free lunch in the world.

Almost everyone has seen a brutal 1-star review on Amazon or a Yelp page. They’re a byproduct of the internet, where everyone’s opinions are a bit more extreme and a bit less polite. The same thing happens in books posted online.

Every so often, we get a comment or review along the lines of, “Pretty good for the survival part at the beginning but it goes downhill fast. The story has large plot holes and has drastically shifted from what it originally was so 0.5/5.”

Sometimes these 0.5 or 1-star reviews are justified and an honest opinion of the reader. Sometimes, they even help us become a better writer. But sometimes, it’s just someone who had a bad day and took their feelings out on the book.

Writing is an intensely personal act. One brutal ratings can turn a good day sour. Ten brutal ratings can derail an entire plot line. And unfortunately, there’s no way to avoid the negativity. It’s just part of writing on the internet.

At the end of the day, opinions and reviews are part of just that. Every successful author has thick skin in one form or another. And in some ways, that’s just as important as the craft of writing.

Writing and more

There’s a healthy dose of luck involved in how we were able to find success so soon out of the gate. But I think where we really struck it lucky was getting the broad strokes right. We just so happened to be two writers who liked working with each other, agreed on quantity over quality, had experience posting online, and read in the same genre. The odds of something like that happening are probably astronomical.

At the same time, some part of our story wasn’t luck. None of this would have been possible without taking that initial leap of faith. In startups, it’s easy to look at a fast-growing company and say that the idea was obvious or that execution was easy. But at the start of the every company is someone who decided to put their skin in the game and try. Writing a book is the exact same.

[1] Shoutout to Dalton Caldwell (YC Partner) who first introduced this idea to me in a batch talk.

[2] Highly recommend reading Beach Read by Emily Henry. Incredible book.

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