5 Questions for Aspiring Author-Entrepreneurs

For most of 2013, most of my nights and weekends have been consumed with a writing (and selling) a book entitled Mining the Social Web (2nd Edition). This makes the fifth tech book that I’ve written in approximately five years, and one thing I’ve come to learn over the course of my book writing adventures is that book writing is a skill in and of itself. Like anything else, the more of it that you do, the more that you learn and can share back with others.

This post presents the following questions (along with some anecdotal advice) that I’d recommend mulling over if you are an aspiring tech book writer.

What are your motives?

Writing a quality tech book of reasonable length is not for the faint of heart. Like any other long-lived effort in an age of waning attention spans and instant gratification, some of the pains involved will push you to a point where you’ll seriously reconsider whether or not this book-writing idea was worthwhile in the first place. On more than one occasion, you’ll contemplate the other things that you could be doing with your time. In the end, if you don’t have a good reason as to why you’re writing the book, you’ll probably quit and be just another publishing casualty along the way.

To be perfectly clear, your motives certainly don’t have to be altruistic or selfless. You just need to be honest with yourself, clearly articulate them in writing somewhere, and review them from time to time. A few of the possible reasons you might consider writing a tech book could include:

  • Rigorously learning a new topic
  • Building your reputation
  • Earning extra income
  • Altruistically fulfilling a need in the market

Of all the reasons to write a book, earning extra income is the one that I’d admonish you to consider the most carefully. The difference between doing something for fun versus doing it for profit can dramatically change the dynamics and relative enjoyment of the activity. The two motivations certainly don’t need to be mutually exclusive, but just make sure that your goal for the book is achievable by your own standards and that you really believe it’s worth a significant portion of your time to accomplish.


If money is your primary interest in writing a tech book, you may find that you don’t have very many problems at all.

How long will it take?

I’d recommend thinking about the amount of effort that it takes to write a quality tech book in terms of both overall effort involved as well as calendar time. The former is based upon estimates that you’ll derive from your outline of the book and can be used to comparatively think about the “opportunity costs” of not doing something else with your time. The latter partitions that overall amount of time into a schedule that fits onto the calendar and helps you to better understand the ramifications of those opportunity costs.

Just a few of the opportunity costs that you should consider:

  • Missed consulting revenue
  • Volunteer work
  • Exercise
  • Social relationships
  • Entertainment

After writing 5 books myself, the base metric I’ve settled upon from my own personal experience is that it takes about 2 hours per page after all of the detailed are worked out. That figure includes the earliest stages of brainstorming, the amortization of time diverted into research activities that inevitably happens along the way, and everything else that leads into the final round of proofreading in which I (re-)read every single word of the final manuscript that’s about to go to the printer. That number may seem high, and your own mileage may vary, but you might at least consider it as a a starting point or as an upper-bound if you think you’re considerably more efficient.


As with software projects, estimating the effort required to write a tech book can be quite difficult. Lots of early peer review on your outline and other efforts to ferret out the “unknown unknowns” that could adversely affect your project schedule is essential.

To illustrate,  let’s assume that you’ve produced a solid outline that suggests you’ll be writing a book that’s estimated to be around 350 pages. Using a heuristic of 2 hours per page, that translates to about 700 hours of effort, and unless you’ve enjoyed a recent windfall or other special circumstances that allows you to approach this endeavor as a full-time job, you’ll be inevitably sacrificing a substantial portion of your nights and weekends for the better part of a year to get it done if you’re moonlighting at the rate of 15-20 hours a week.

One other consideration that you should always take into account with any activity involving estimation is Hofstadter’s Law, which is defined as follows: It’s always takes longer than Hofstadter’s Law predicts that it will, even when you take into account Hofstadter’s Law.

Seriously, estimation is not easy, and you’ll find that there are gaps in your outline that you’ll need to fill along the way. Those detours can really start to add up. The bottom line is that it will almost certainly take longer than you anticipate to write a book that you’ll be proud of writing. Be sure to regularly reassess your original estimates and update them along the way.

To self-publish or not to self-publish?

Besides making that initial mental commitment to write a book, determining whether or not to work with a publisher and choosing a particular publisher is probably the biggest decision that you’ll make. I’d recommend approaching this very important decision with standard cost-benefit analysis as well as from the basis of whether or not you need a partner to achieve your goals for the book or if you can do it alone.

As with any other relationship in life, open and honest communication is key, and it’s imperative that you manage expectations properly. Your relationship with your publisher (and even more specifically, with your editor) is no different. A good way to think about “manage my expectations” is “don’t surprise me”. From the standpoint of working with a publisher, that typically translates into staying on schedule and adhering to the agreed upon outline for the content.

However, you’re the one who will be staying up late and making lots of sacrifice to produce the book as a moonlighting activity, so you should be sure that the publisher can meet your own expectations before engaging in a (legally binding) partnership with them. A few questions to consider during your initial conversations with a publisher:

  • What type and frequency of feedback will you provide?
  • How much grace is extended for missing deadlines or potentially extenuating circumstances?
  • How much can I deviate from the original outline without renegotiating the contract?
  • Will I ever be able to renegotiate any key financial metrics like royalty rates or advances?
  • How much “production support” are you providing for professional illustrations, proofreading, copyediting, etc.?
  • What will you do to market/sell the book once it’s complete?

There’s a real value that you can estimate and place on those factors. Sure, you could do it all yourself, but that would take up even more of your time and translate into even higher opportunity cost.


You could self-publish, but you could also do lots of other things with the time that it would take to produce a truly professional work. Carefully consider your motives and goals for producing the book before deciding that self-publishing is right for you.

In an era of self-publishing, ebooks, and print-on-demand services, I’d recommend that you hold the publisher to very high standards on at least the following fronts:

  • The shaping and refinement of your initial ideas
    • Don’t underestimate taking into account the importance of writing a book that the market needs as opposed to just writing a book that you want to write.
  • Constructive criticism about your manuscript as it evolves
    • You need the feedback, no matter how good you think that you are. You want your product to be the best that it possibly can be.
  • The application of quality production processes to the final manuscript
    • This is seriously tedious work that you really don’t want to do yourself and are paying a huge premium for by working with a publisher. Make them earn it!
  • A solid distribution channel with ample sales/marketing
    • Once your book is complete, it’s a product. At that point, it’s not not about writing; it’s about addressing the market and selling it.

In my recent book-as-a-startup experiences with Mining the Social Web (2nd Edition), it’s the application of production processes and the distribution channel that have provided the most value. Multiple rounds of proofreading, copyediting, professional illustrations, and the creation of cover art are all things that I’d rather not have done for myself and certainly took the professionalism of the book to a whole new level. In terms of distribution, suffice it to say that it is certainly in the publisher’s interest to see your work succeed, but you are only one of scores of authors that they are probably working with, so temper your expectations.

One expectation that you should certainly not not misunderstand is that your publisher is not your primary source of sales and marketing. You as the author are your primary source of sales and marketing. Once you have a final product in a distribution channel, there will probably be some momentum from a small PR campaign around your book that the publisher takes care of, but that’s really just to set off a spark. The real sales and marketing is up to you, and you’ll have to be enterprising to figure out what’s working and what’s not working. I highly recommend the application of Lean Startup principles, which is a good segue into the next topic.

Is it a project or a product?

Trick question! It’s both — though not quite at the same time. The distinction that I’m making between project and product can be illustrated with the following two pieces of advice:

  • The process of writing a book is a project
  • A book is a product that you sell

The takeaway here is that if you only think about your book as a project, then the project basically ends once you have a product in the publisher’s distribution channels. At that point, the project is “complete” aside from some ad-hoc work you might occasionally do to promote it. By the time the book publishes, you’re probably frazzled, exhausted, and just want to regain some balance in your life, so it’s a very natural reaction to feel a sense of accomplishment, breathe a sigh of relief, and trust that the publisher will sell it for you. After all, if it’s any good, it’ll just “sell itself”, right?


A project and a product are two entirely different things. Think carefully about them as your manuscript approaches final form and strongly consider treating your book as a startup. The experiential benefits can be tremendous and of incalculable value regardless of the success of the book itself.

I’m confident that you’ll make a few bucks with your book while you momentarily decompress from the surge to get it across the finish line, but I’d strongly admonish you to reengage and treat it like a product from that point forward. The decision to think of your book as a startup and yourself as the CEO of this tiny little startup is a lot more work compared to performing ad-hoc work whenever you feel like it, but it unlocks an entirely new perspective on life.

With a product and distribution channel in hand, you’ll be forced to think about things that you’ve always taken for granted (or thought of as unimportant/easy work) in other professional engagements. A few examples of the hats you’ll wear as an author-entrepreneur with your book-as-a-startup business to get you thinking:

  • As CEO, what should you be doing to maximally promote the book? Blogging? Speaking engagements? Book tour? Should you spend money on various sources of online ads? Should the book just be a prop for consulting?
  • As CMO, can you accurately estimate the size of your addressable market? Determine if your messaging is as effective as it needs to be?
  • As COO, can you explain the prior month’s revenue? Forecast the next month’s revenue?
  • As CTO, is there a way that you can simplify the user’s experience to try out the code? Perhaps a VM or a web app that’s trivial to install?
  • As the SVP of Customer Service, can you institute a system to respond to unhappy readers? Before they leave you a bad review?

At the end of the month, it really all boils down a single number: revenue earned. The arithmetic and accounting reports (as provided by the publisher or online publishing system) are pretty simple. As the author-entrepreneur, it’s your job to do something about them.

What is holding you back from selling more books? Is it a flawed product, or is it a marketing issue?

Writing a book is one thing. Selling a book is a different beast entirely.

Marketing is hard.

The following video is a short ~5 minute Ignite talk that provides some (hopefully motivational and entertaining) information on the notion treating a book as a startup.

What is its expected shelf life?

Last but certainly not least is the longevity of your book, regardless of whether you prefer to think of it as a project or a product. In either case, you’ve invested non-trivial effort into making it a reality, and you probably won’t look forward to the maintenance involved in keeping it up to date, or the day that you have to rewrite significant portions to reflect changes in the underlying technology that backs the dialogue and example code.

As much as you need to understand your addressable market, you need to understand the technology that you are including in your book, the community that backs it, and any roadmaps that may (or may not) exist. Take it from someone who has written a book that was affected by fairly major changes to the social web landscape (short-notice Twitter API changes, the retirement of Google Buzz and the birthing of Google Plus, OAuth 2.0 evolution, etc.) that it’s not enough to just write about what exists right now.

You need to craft your written message so that it’s as evergreen as possible. In the words of a famous Canadian hockey player, you want to “skate where the puck’s going, not where it’s been”. Be as prescient as possible in making the right bets in terms of what you introduce in written form (the book) versus what you can provide as an online supplement that will be much easier to maintain. As with (successful) software projects, the majority of the effort required is usually during the maintenance of the product after it’s been operationalized. Why should a successful tech book be any different?


How does the shelf-life of your book compare to the shelf-life of these Twinkies?

Revenue is trust. If your customers trusted you enough to pay for a product with your name on the front of it, you can either take care of them and show yourself worthy of that trust, or you can inevitably tarnish your reputation. And that’s not good for business.

Closing Remarks

Writing a successful tech book is an incredibly daunting endeavor, and if you really want to maximize the revenue opportunities associated with it, you’d be wise to think of it in terms of a tiny startup business, apply some Lean Startup principles, and treat yourself to the entrepreneurial education that only real world experience can bring. It will require more sacrifice than you think that it will, it will take more time than estimate that it will, things will go wrong, and the whole process will truly test you. However, you will come out the other side stronger, wiser, and with “street smarts” that you can’t get by just sitting around and talking about things.

Talk is cheap. Don’t be cheap. Get to work on that book, and let me know if there’s anything I can ever to do help you. I hope to share some more book-as-a-startup posts in early 2014.

1 Comments on “5 Questions for Aspiring Author-Entrepreneurs”

  1. Pingback: 5 Questions for Aspiring Author-Entrepreneurs | Enjoying The Moment

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