Category Archives: Publishing

Why is Great Marketing Like Sailing?

Illustration of Pond Island, MaineThere is something powerful about a personal recommendation from a trusted source. A trustworthy friend’s “all-time favorite, must-see place to visit” and their “you’ve absolutely got to read this” statements have credibility—much more credibility than paid ads displayed in your Facebook feed recommending the same things. So how can personal recommendations spur better marketing?

A comparison of marketing and sailing can provide some insight.

Why is great marketing a lot like sailing a boat?

Just like a gust of wind, word-of-mouth is a force that occurs naturally in the world. A sail boat requires the power of the wind to move forward. Similarly, a brand can employ people’s innate desire to share great experiences. Brands offering remarkable products can employ the naturally occurring phenomena of people making personal recommendations on the brand’s behalf. Think of it as putting up a sail to capture the wind. This is called Advocacy Marketing.

Brands that offer a remarkable product experience can be propelled forward by the power of Advocacy Marketing. Brands that don’t—they’ll have to do some rowing.

Marketing should be less like rowing.

Today, marketing feels a lot more like rowing a boat. Each movement forward requires the exertion of energy. Marketing departments will spend vast amounts of money on TV commercials, radio ads, Web links and banners, etc. to compete for your attention. None of these methods have the power to influence you like an authentic recommendation from a trusted friend. And all of them require a constant input of energy and capital to sustain.

This analogy became very clear in my mind while recently kayaking in Maine. My destination was to see a historic lighthouse on Pond Island. The experience of rowing to the island was enjoyable, but I remember thinking how the natural forces all around (i.e. the wind, current, and waves) were so much more powerful than my own efforts to propel myself forward with only a paddle. It was a much easier return trip with the wind at my back and current pushing me forward.

When Timing is Everything

Predicting the future: How ocean kayaking compares to picking the next bestselling book.Illustration of Pond Island, Maine

Only once we concede that we cannot depend on our ability to predict the future are we open to a process that discovers it.
- Duncan J. Watts [1]

Just several hours earlier, I had been walking through soft mud on the spot we now sat floating. My wife and I had been rowing our rented kayak in Sagadahoc Bay, Maine during high tide and had stopped for a rest. The shoreline in the bay will move by over a mile depending on the high and low tide, so our break needed to be short. We stole one more look at the beautiful trees on both sides, and then started in again towards Pond Island. Our plan was to get a quick glimpse of the historic lighthouse standing on the island prior to the tide going back out.

We had been informed by Pat (the person who rented us the kayak) that Pond Island would be straight ahead and to the right when coming out of the bay. Sure enough, as we rounded the right shoreline at the mouth of bay, there sat the small island in the distance.

After leaving the protection of the enclosure, the waves became much choppier, in part, from motor-powered boats passing through the waterway between the shoreline and the island. The larger waves and traffic meant less opportunity to cruise along and take in the surrounding beauty. Our focus was straight ahead on the island, or scanning to avoid the much larger, faster boats.

It occurred to me while rowing in the rougher stretch of water that predicting the behavior of other boaters was considerably more difficult than predicting the historically documented high and low tide water marks. This comparison was spurred in part by reading about the complexity of predicting the future in Everything is Obvious : Once You Know the Answer by Duncan J. Watts. Using book publishing as an example, Watts describes how challenging predictions can be:

When a publisher offers an advance for a book, the book itself is typically at least a year or two away from publication; so a publisher has to make a prediction not only about how the book itself will turn out but also what the market will be like for that kind of book when it is eventually published, how it will be reviewed, and any number of other related factors. [2]

Rowing with our eyes closed and guessing where another boat might be in ten minutes is a pretty silly strategy. Similarly, predicting a book’s success two years in advance requires a whole new way of thinking in this rapidly changing marketplace. Whether it is in ocean kayaking or book publishing, it’s important to recognize the limitations of using common sense and intuition as methods (please see the The Gatekeeper is Guessing by Michael Boezi) when trying to predict a future outcome in complex world.


1. Duncan J. Watts. Everything is Obvious : Once You Know the Answer (New York: Crown Business/Crown Publishing Group/Random House, Inc., 2011), 196.
2. Duncan J. Watts. Everything is Obvious : Once You Know the Answer (New York: Crown Business/Crown Publishing Group/Random House, Inc., 2011), 164.

Time Will Tell

Using technology as a platform—not the reason—for change in the publishing industry.Illustration of the Jefferson Market Library in Greenwich Village

At the intersection of relevance and obsolescence is the ability to recognize opportunities for change based on shifting consumer behavior and the subtle coalescence between emerging and disruptive technology.
-Brian Solis  [1]

The book publishing industry is in a state of transition, and there appears to be two polar differences in perception about what this change means for the industry. On one side, there are pronouncements that book publishing as it is known today is on a path to obsolescence, the only option being to delay the decline for as long as possible. However, there are others in publishing who state that the industry must be completely remade to survive in the long term. Those advocating for fundamental transformation will often refer to new technology development and application as the reason to disrupt the status quo.

My own opinions about the future of publishing were greatly influenced by a recent trip to New York City. Traveling by foot down Sixth Avenue, I discovered the historic Greenwich Village. While I stood at the stoplight waiting to cross 12th Street, my eyes looked up to see a beautiful building that appeared to be a church.  After doing some research later that week, I was surprised to learn that this building was operating as a public library. Even more unexpected, the structure originally served as a courthouse after the initial construction was completed in 1877. Now called the Jefferson Market Library, the building was almost torn down in the late 1950s after sitting vacant, no longer in use as a courthouse. It took the advocacy and support of some influential and concerned residents to save the historical landmark by converting it to a library. [2]

I believe the evolution of the Jefferson Market Courthouse to the Jefferson Market Library serves as a wonderful example of modernization without sacrificing the historically significant. This example of preserving a historical foundation while embracing progress acts as a powerful metaphor for the book publishing industry. I was again reminded of the future of publishing when reading Brian Solis’ new book, What’s the Future of Business? in which technology is not described as a “catalysts for change, but merely among its agents.” Emerging and disruptive technologies are not the reason to transform book publishing. They are a platform for the industry’s evolution.[1]

1. Solis, Brian. What’s the Future of Business? (Hoboken, New Jersey: John Wiley and Sons, 2013), 150
2. Acquired from New York Public Library Website – NYPL.org

The Ground Worth Struggling For

Finding that key competitive position: a great lesson for the innovative leader from Sun-tzu’s The Art of War.City of New York Public Library Lion

When the ground
Offers advantage
To either side,
That is
Strategic ground.
- Sun-tzu  [1]

A few hours before my train back to Boston departed from New York’s Penn Station, I stopped by the public library for the chance to reflect at the end of a demanding business trip. There was a strong pull for me to the familiar lions who guard the entrance to New York Public Library Schwarzman building now and for the past 100 years. [2] These silent guardians sat as reminders of one my favorite thinking places in Boston, the public library that also has lions (please see A Storied History), lying couchant, protecting the thoughtful.

This trip to New York is one of the many I will have to make in my work to try and develop a business around innovation in the book publishing space. My work for an early stage startup provides the privilege of seeing raw innovation morph into something valuable to the world– this is the intersection where scientific experiment meets practicality during the evolution of a business.

I sat there quietly in the library’s grand reading room making follow-up notes about the potential strategic partners and customers I had met on the trip. During this time a realization began to form about strategy based on a lesson from Sun-tzu regarding the different types of ground in which to do battle in The Art of War. Sun-tzu’s instruction tells us that strategic ground is “[l]eternally, ground worth struggling for…” as translated by John Minford. That being said, it has been my great surprise as an entrepreneur how challenging the act of identifying a key strategic position can be that is both advantageous and accessible for a developing business. Accordingly, it is my belief that great entrepreneurs are effective because they have the capacity to abstain from seemingly strategic opportunities that are not yet accessible to a new business.

Jason Freeman is the founder of Work of Start.


1. Sun-tzu (Sunzi); translated with an introduction and commentary by John Minford. The Art of War (New York: Penguin Group, 2009), 268.
2. Acquired from New York Public Library Website – NYPL.org