Releasing the second edition of my Dropbox guide

A few months ago, the second edition of Dropbox In 30 Minutes was published. It’s one of our most popular guides in the In 30 Minutes series. In fact, some people mistakenly confuse it with Dropbox For Dummies. This post will get into the thinking behind the second edition of the guide, from content to production to marketing.

Dropbox on a mobile device

Dropbox In 30 Minutes was the first guide published in the In 30 Minutes series. Released in the summer of 2012, it quickly began to sell in channels such as Amazon and Apple’s iTunes store. The paperback edition, released in the fall of 2012, also was a hit. The first edition was downloaded or purchased as a paperback thousands of times over an 18 month period. It currently is listed as one of the top Software Utility guides on

Not long after making the title available, I recognized a problem: Certain information tended to quickly become outdated. While the core concept of Dropbox — software that helps you sync files between computers and mobile devices — has remained the same, specific aspects of the software have shifted. For instance, the Dropbox logo has had several noticeable tweaks in the past few years. Of a more practical concern for readers, the interface for mobile devices — iPhones, iPads, Android phones, etc. — has been completely overhauled. The desktop program for Windows PCs and Macs has also changed, albeit in a more restrained manner (for instance, right-clicking on a file brings up different options for sharing or manipulating the file in question).

For a while, I made incremental tweaks to the text of the guide and simply updated the content files for the ebook and paperback editions. But then I became aware of two additional issues that needed to be addressed:

  • The “publish date” for the guide, which was listed on the product pages on Amazon, Barnes & Noble, Apple and Bowker’s ISBN database began to look old. For fiction books, “2012” is considered “new”, but in the world of how-to manuals for popular software programs, a two-year-old title starts to look a little long in the tooth.
  • Older versions of the paperback guide were being resold on Amazon. I don’t blame readers for doing this, but the problem is a reader in early 2014 purchasing a used edition from July 2012 would be getting a fair amount of outdated information. This resulted in understandable frustration.

The second edition of the Dropbox book hits the market

Because of this, I decided to issue a Dropbox In 30 Minutes, Second Edition. I hired a review editor to go through the original guide and flag bits which needed to be rewritten and have new screenshots. I also redid the annotated screenshots of the Dropbox mobile application, and added new sections relating to Camera Uploads, security, Dropbox for Business, and more. I’ll continue to do small tweaks as conditions warrant, but I already have my eye on Dropbox In 30 Minutes, 3rd Edition!

If you are interested in downloading or purchasing a copy of the guide, please see the options on this page.

Startup publishing and managing early growth

At a certain point in the lives of most product-oriented ventures, founders confront a slew of growth-related issues. In this post, I am going to talk about growth in the context of startup publishing, and the challenges that my own publishing company i30 Media has faced over 18 months of growth.

Startup publishing example: In 30 Minutes guidesA bit of backstory: i30 Media publishes how-to guides under the In 30 Minutes® imprint, as well as several fiction titles. The most recent release is Windows 8 Basics In 30 Minutes. The venture started in mid–2012 as a Lean Media experiment with just a single title written by myself and distributed on Amazon’s KDP self-publishing platform. Since then I have incorporated the venture. I30 Media has released about ten In 30 Minutes guides in various ebook formats as well as in paperback, and distributes to every major ebook platform (Kindle, iBooks, Nook) as well as growing platforms (Google Play Books, Kobo).

In the first six months of the venture, I was occupied with figuring out the publishing landscape, expanding distribution channels, cranking out early releases on my own. While I was new to book publishing, I am not new to the media industry, and applied domain knowledge from magazine/news publishing, online media, and the mobile app space.

Startup publishing: scaling production

One of the first growth lessons was being forced to give up the “one-man band” idea. That guy attracting a small crowd on the local town common with a drum pedal strapped to his foot, a tuba around his waist, a harmonica in his mouth, a xylophone in one hand and maracas in the other is technically able to mimic a real band. But he will be limited in what he can do with his instruments (e.g., the xylophone sounds better using two hands than one) and quality ultimately suffers. Actually, let’s not beat around the bush — one-man bands sound terrible. Can you imagine listening to their stomping, honking tunes on the radio, or downloading the music to play at home? People enjoy one-man bands for the spectacle, not for the music.

I was a one-man band in the first month. I did everything, from writing to setting up the websites to designing the cover image. And I wasn’t doing it for the spectacle. I did it because it was cheap and I could do everything. But I could see there was a quality gap with the competing titles available on Amazon and elsewhere. The covers looked amateurish, and I was worried about the quality of the copy. I began to look for things to outsource, and one of the first was cover design. I contacted Steve Sauer, a graphic designer I used to work with, who was happy to take on the freelance work for his consulting firm Single Fin Design. His first cover, for Dropbox In 30 Minutes, was a big success. I decided to have him do new covers for other In 30 Minutes guides going forward, starting with the Google Drive and Google Docs guide and our Excel Basics book.

I also found people to handle other tasks, including copy editing and market research. But the big growth impediment was writing. It was quickly apparent to me that I could not grow In 30 Minutes guides into a successful brand unless I found other authors. While the guides don’t take long to write (I tell prospective authors that the first draft of a 10,000–15,000 word guide typically takes 5 or 6 weeks, writing on nights and weekends) there is so much other stuff to do when it comes to growing a business — marketing, expanding sales and distribution, accounting, dealing with production issues, etc. As i30 Media grew, I knew that I would have less time to spend on writing. The only way to keep growing and strengthen the brand was to find other authors to write new titles, including topic areas in which I had no expertise.

The impact of my recruitment efforts is apparent when looking at the In 30 Minutes catalogue. Of the first 5 titles, four were written by me, including the Dropbox book and the Google Docs for Dummies substitute. Of titles #6 through #10, only one was written by me.

Startup publishing: scaling sales

Besides production, the other side of growth relates to sales. As mentioned earlier, I follow Lean Media principles when it comes to marketing and sales. That entails lots of experimentation with everything from advertising to sales calls to potential enterprise customers. But it’s not just about identifying opportunities, and then measuring the impact of pilot experiments. In order to expand growth, it’s also necessary to identify which opportunities not to pursue.

One area which I have stayed away from so far is bookstore distribution, based on early discussions with (mostly disinterested) bookstore managers, an evaluation of visibility and competition within B&N and Staples, and the industry standard requirement that demands 55% discounts and the right to return or destroy unsold copies. I haven’t completely written off the opportunity (in fact, I have made many titles available through the back-end ordering systems that bookstores use) but I don’t want to spend loads of time fighting to get In 30 Minutes guides in a channel that may ultimately be unprofitable.

I have also avoided ebook platforms that have too much overhead, are weak on terms, or look like they could undermine or cannibalize other sales channels. I stayed far away from Sony’s ebook platform, owing to the way it basically demanded that independent publishers beg to join. I have also been a skeptic of Scribd’s ebook subscription service.

What does the future hold for i30 Media? Certainly, more guides and more sales. In addition to the Windows 8 user guide, I have a new title about jQuery plugins in the works as well as a non-technology title (still in stealth mode). I am also planning growth of the company itself. Already I have begun thinking about hiring my first employee. The numbers aren’t aligned yet, but we could see action on this front in 2015.

Positioning: A powerful marketing concept (with some limitations)

A few years ago, I picked up Positioning: The Battle for Your Mind, by Al Ries (with Jack Trout). It’s a quick read, and an old book (it was written in the 1980s, and based on a series of articles for Advertising Age that date from the early ’70s) but it was recommended by Lean Startup practitioner Ash Maurya, author of Running Lean. When I began writing books, I used some of the ideas in Positioning to position Dropbox In 30 Minutes as well as a second guide that is like a Google Docs for Dummies alternative. But it wasn’t just the technical topics that appealed to people — I actually created a series of guidebooks that can be read in 30 minutes. I learned from customers that this “positioning” is very compelling. It’s worth digging into the concept to learn how it can be applied elsewhere, while keeping in mind that there are some limitations.

Positioning, by Jack Ries with Al Trout

Summary of Positioning by Ries and Trout

Positioning starts with several compelling premises. First, we are constantly bombarded with marketing messages. “We have become the world’s first overcommunicated society,” Ries writes. “Each year, we send more and receive less.” As a result of the huge volume of marketing messages, advertising is like a “very light fog that envelops your prospects.” Note this was written long before the advent of the World Wide Web and mobile phones!Beyond the challenge of getting noticed, is the issue of convincing people to believe in the messaging. According to Ries, this is where many companies make a big mistake — trying to change audiences’ minds that their products are better than the market leaders.

“Were the average consumer rational instead of emotional, there would be no need for advertising,” Ries says. The reasoning here: Customers would gravitate toward better-quality products, regardless of who produced them or how they were marketed.

Of course, that’s not what happens — people tend to gravitate toward the familiar brands and products at the “top of the ladder” for each product category. And knocking the market leader off that ladder with claims about quality is nearly impossible.

Therefore, according to Ries, it makes sense to work with what customers already know. Strategy should be built from the perspective of the “prospect”, rather than the perspective of the company (and the ego of company executives). Often, this involves finding the hole that the market leaders have neglected or don’t serve well.

These are the concepts that lie at the heart of Ries’ and Trout’s thesis, and they use many case studies and examples to illustrate the companies, brands, and products that have successfully positioned themselves in the mind of the consumer. Consider these examples from decades past, and the holes that they filled:

  • 7-Up: “Uncola”
  • VW Bug: “Think Small”

In the first example, 7-Up was introduced to a market which associated “soda” with “cola”. It filled a hole for people who wanted something other than cola, which was at the top of the sweetened carbonated beverage ladder. The original VW Bug couldn’t compete with what drivers saw in the size and power of cars from Detroit, so its marketers sidestepped those issues and concentrated on the hole that Detroit had neglected — small vehicles, which have their own advantages in the minds of the prospect: price, parking, fuel use, etc.

Other marketing strategies in Positioning

There are other strategies Ries mentions in Positioning. One involves invoking other successful products. One clever example involved positioning Jamaica as “The Hawaii of the Caribbean.” It’s a great line, but it apparently fell victim to micromanagement at the highest levels of Jamaica’s government.

However, I had to question other parts of Positioning. For instance, Ries spent a lot of time discussing the importance of of having the right name. Some of this makes sense, such as the example he used of “Hog Island” being a poor choice for a tropical resort until it was renamed “Paradise Island.”

But should companies completely avoid “coined names” like Coca-Cola? I think the jury is still out on this one. Ries states that it’s “dangerous” to have “mean-nothing” names, and it only seems to work when the product is first-to-market, like Xerox. But in the digital age, we have seen a slew of successful companies and products that have obscure or semi-relevant names (Google and Google Docs, Apple and the iPod, Nintendo and the Wii, etc.) None were first-to-market in their respective categories, yet all have been runaway successes.

On the other hand, some people in the digital realm are still firm believers in using easy-to-remember and easy-to-spell names. At a conference a few years ago, I heard Mint cofounder Aaron Patzer talk about spending a lot of time on finding (and paying for) the right name. The personal finance tracking site had to be easy to understand, spell, and enter into a browser address bar. He also thought his competitors were crazy for choosing names that were hard to spell or pronounce — he specifically mentioned and

Ries also struggles with disentangling positioning problems from other business problems. For instance, he suggests that Eastern Airlines was failing at the time of the book’s writing because of its name (“when prospects are given the choice, they are going to prefer the national airline”). No mention was made of deregulation, new competition, Eastern’s fleet, or the titanic management/labor struggles Eastern was dealing with at the time.

Positioning a big company vs. positioning a startup

It must be noted that the ideas in Positioning are often best suited to major national brands and multinational corporations. Startups may find some lessons here — I certainly derived value in the hole and ladder concepts described above. But other theory and examples will resonate best with people who work for Google, G&E, and other giants of the corporate world, in which big-budget advertising campaigns and months-long market research studies are possible. Ries is clear that it takes time and money to follow his advice (e.g., “If you don’t spend enough to get above the noise level, you allow the Procters & Gambles of this world to take your concept away from you”). Of course, time and money are two things that most startups don’t have.

Lastly, Positioning is a book from another era — the golden age of one-way mass media. It was written long before the Web, social networks, and mobility had a chance to impact the way people communicated and formed opinions. Technology-driven trends such as the Web or mobile phones as well as game-changers such as Google search results must be considered in any discussion about marketing, but these developments came too late for Positioning. On the other hand, it leaves a few holes that I am hoping other authors, bloggers, or experts will try to fill.