Three months after deciding to write a book about building, launching, and maintaining a web application, the progress is good. I’d like to be further along, but took a break from writing to spend some time on Sifter. So where are things at and what have I learned about self-publishing an eBook?

First and foremost, the logistics took a lot of time. Planning the content, understanding the world of digital publishing, settling on a good workflow for both the writing and editing, as well as choosing the right tools all took quite a bit more time than I would have liked. Thankfully that’s all behind us now.

PDF, epub, etc.

The first thing I wanted to work out was how the whole process would work. I didn’t want to write in one format/tool only to have to later go through and manually edit everything to put it into the final format. Similarly, I wanted to make sure that the process worked well for our editor and the various other people providing feedback. Long-story short, given limited resources and the goal of having a lot of graphs and visualizations, I wanted to keep everything as simple as possible, and we settled on publishing only a PDF.


Since we’re only doing a PDF, I chose to put everything together in iBooks Author. Given that decision and the usefulness of tracking changes in Pages, I’m writing everything in Pages and storing it all in Dropbox for easy sharing with the editor and various others providing feedback.

As the files are updated, we simply update the file name with “(Assignee Name)” at the end. The beginning of each file name is in a “#.#” format where the first number indicates the section and the second indicates the chapter/topic within that section. So each file looks something like “1.2 Topic Name (Assignee Name)”. This makes it easy enough to reorganize content without involving too many different applications.

With all of this, the only challenge has been that Keith, my business partner, is a Windows user and can’t easily edit Pages documents. Fortunately, he’s providing higher level feedback, so this hasn’t been a significant problem.

Planning the Content

One of the most challenging parts was narrowing down the scope. In some cases, each of these topics could be 10,000 words by themselves. The way that I narrowed it down was to focus purely on logistics. While I mention technical bits that need to be in your plan, I’m primarily focusing on things that need to be done, things that are easily overlooked, or things that are tempting to cut out.

While I expect it to evolve a bit, the book is primarily broken up into 4 sections of 9 topics each. Each topic is about 900-1,200 words. Fortunately, now that this is about 90% locked down, the writing has been flowing nicely.

The Research

With the book, I want to share a lot of the data that I’ve used to make some of our decisions over the years. This has required doing a fair amount of legwork and writing a few more SQL queries than I would prefer, but fortunately it’s all done. I’ve been swimming in data, and found some really interesting things to discuss.

The Spreadsheet

Originally, I wasn’t sure if I wanted to do more than a book, but as I started writing, I realized that much of our decision making is an extension of the information that we have in a rather complex spreadsheet that I update monthly. So, I spent a few days and redesigned and rebuilt the spreadsheet from scratch so that it would be easy to use and compliment the book.

The goal of the spreadsheet is to help get a clearer grasp of the costs of starting and running a web application. It can help make the numbers very real and let you quickly adjust numbers to understand the impact of charging $9 a month or $29 a month. Honestly, I might argue that the spreadsheet is almost as helpful as the book itself. They’re a team, though, and the spreadsheet should really help anyone who’s trying to put together a budget.

The Vendor List

In addition to the spreadsheet, I’m also compiling a vendor list for the wide variety of services that one would need to enlist in order to build a web application. Hosting. Transactional email. Help desk. Domains. DNS. Continuous integration. Email newsletters. Log monitoring. Performance monitoring. Uptime monitoring. Source control. Team communication. And more. I’m not going to review any of the products, but the list should definitely make it easier to quickly narrow down which tools are best for a given team’s needs.

The Writing

This is where I’m spending my time these days. The book is about 25% complete, including editing. I expect to finish all of the writing this week, and then it’s off for feedback and editing. Once that’s complete and all of the content is laid out, I’ll be passing it along to a handful of other folks who’ve launched their own applications in order to get some final feedback and additional perspective. Then I’ll incorporate their suggestions and it’s just a matter of picking a day and finishing propping up the store.

Due Date

I’m not sure exactly when it will be ready, but I can say that I’ll be wildly disappointed if it’s not available by the end of March. I’m racing to get it out long before that, but that’s my current drop-dead date. My main concern is that I want to allow the reviewers plenty of time to read it and share their feedback.

Some Random Thoughts

As I progress on the book, I’m more and more excited to get it out there. It’s not rocket science, but I constantly imagine myself five years ago and wish desperately that I could have had access to all of this information rather than just figuring it out as I went along.

I truly believe that this information would have saved me at least a month’s worth of development effort if not more. It would probably have also saved me about two weeks worth of research. The spreadsheet alone incorporates several years of acquired knowledge that should make it dramatically easier to plan your finances or at least make a much more educated guess.

Ultimately, I’m really excited to help people get better products out the door in a shorter period of time with a whole lot fewer mistakes and less pain. I figure the sooner it’s available, the sooner others can begin benefitting from all of these lessons.