All posts by Jason Freeman

Ready, Aim, Aspire: Why Your Startup Story Matters

Cannon on Georges Island.What happens if your aim is a little off when launching a startup? You better have a great story. A story is not an excuse. It’s the reason why every miss is just the calibration required to do great things.

What’s in a great story?

A story needs to authentically connect. As Seth Godin says in his book All Marketers Are Liars, “A great story is true. Not true because it is factual, but true because it’s consistent and authentic.” [1]

Whenever possible, address a problem head-on. That’s a true lesson from one of my first professional stories. It comes from my days selling motorcycles when I was nineteen years old.

I was brand new to selling. In fact, this story is about the first bike I ever sold from a catalog. And this first sale happened to be with a rather large man who looked the part of a tough biker dude.

When we made the order, both the customer—the tough looking gentleman—and I thought it was for a black motorcycle. A week or so later the bike comes in to the dealership and it’s not black. It’s painted a deep purple.

I vividly remember pacing the floor in the dealership’s repair shop trying to come up with some reason that would justify my mistake…more accurately, trying to pin blame somewhere else. The pacing stopped when the head mechanic walked over. He looked me right in the eyes and said “Jason, don’t ever be afraid to address an issue.” I wasn’t aware he even knew my name.

Well, the customer shows up and the first thing that comes out of my mouth is “the bike is purple. I know we both thought it was black. But it’s not. It’s purple.”

The customer stood there and smiled after my confession. And after thinking for a moment he placed a hand on my shoulder and calmly said “let’s go check it out.”

As we approached, the motorcycle sat outside gleaming in the sun with its deep purple. The customer took a moment to walk around the bike and then he exclaimed “I love it!” I finally exhaled the breath I was holding and made myself a promise to always work to address a problem head-on. Funnily enough, it struck me sometime later that the head mechanic had put the bike in the perfect spot to bring out such a rich color under the sun.

A consistent story in a changing world

I recently picked up a very interesting story. It’s a story of how advances in technology can be transformative. On a day trip to Georges Island (one of the Boston Harbor Islands) I learned that this was the spot of the now decommissioned Fort Warren. The fort was closed due to advances in weapons technology, mainly long-range missiles. The story of Georges Island did not end with the military fort closure. The island has since been converted to a recreational area where visitors come and learn about an important piece of history by seeing where the soldiers lived and trained.

In All Marketers Are Liars, Seth Godin also writes about how a story is required to survive in a changing world. He uses the curse of the Red Queen to provide insight through analogy:

“Just as in evolutionary biology, the game is always changing. The evolutionary paradox called the curse of the Red Queen states that what worked yesterday is unlikely to work today. When Alice was busy playing chess in Wonderland, the Red Queen kept changing the game whenever she moved. The same thing occurs in our marketing wonderland. One competitor makes a change and suddenly the entire competitive landscape is different.” [1]

The cannon displayed on Georges Island may no longer be effective in military use, but it now serves as a remnant of a different time. The story of Georges Island is still being told and it continues to be interesting.

A startup must also tell an authentically compelling story because every new venture has to adapt in order to survive. It’s an aspirational story of why a startup was created in the first place that can stay consistent through this evolution.

1. Seth Godin. All Marketers Are Liars: The Power of Telling Authentic Stories in a Low-Trust World (New York: Portfolio/Penguin Group (USA) Inc., 2005), 8, 25-26.

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.

Picking a Better Path

Progress as a decision maker: Chip and Dan Heath advocate for using a process to make life’s significant choices.

Cathedral of Saint John the Divine

In life, we spend most of our days on autopilot, going through our usual routines. We may make only a handful of conscious, considered choices every day. But while these decisions don’t occupy much of our time, they have a disproportionate influence on our lives.
– Chip and Dan Heath [1]

There is something quite remarkable about the Cathedral of St. John the Divine (please see Always Seeking Resistance), located in Morningside Heights neighborhood of Manhattan. This Gothic cathedral is one of the largest churches in the world, but the truly notable part for me is that the original plan was to create a grand Romanesque, Byzantine cathedral and not Gothic. Almost two decades of building had been done before the decision to change to a Gothic architecture was implemented, which required the amalgamation of the past construction that was already completed in the Romanesque and Byzantine design. [2]

Chip and Dan Heath describe in their new book, Decisive – How to Make Better Choices in Life and Work, a process for making the types of decisions that have a major impact in a person’s life. In order to highlight the importance of these types of decisions, they borrow the analogy of driving, pointing out that “…in our cars, we may spend 95% of our time going straight, but it’s the turns that determine where we end up.” [1]  Having gone through various twists and turns since construction began over a century ago, the Cathedral of St. John the Divine’s journey is still not yet complete since this beautiful building stands unfinished to this day. [2]

Jason Freeman is the founder of Work of Start.

1. Chip and Dan Heath. Decisive: How to Make Better Choices in Life and Work (New York: Crown Business/Crown Publishing Group/Random House, Inc., 2013), 28.
2. Acquired from the Cathedral of St. John the Divine website –

Always Seeking Resistance

Creating art requires moving outside of a comfort zone: insight from Seth Godin about the nature of being an artist.

Peace Fountain next to Cathedral of Saint John the Divine

The resistance is the confused and angry noise in our heads that shows up whenever we put our creativity on the line…The resistance is a symptom that you’re on the right track. The resistance is not something to be avoided; it’s something to seek out.
– Seth Godin [1]

At the end of a book publishing conference in New York, I met a friend for an excellent Thai lunch in Morningside Heights. She then offered to show me a neighborhood landmark and one of the largest churches in the world, the Cathedral of St. John the Divine. The Gothic church is enormous and its edifice is beautiful, but it was the visually interesting statue within the outdoor Peace Fountain that first caught my interest. The statue demonstrates a collage of imagery including angelic battles, animals with distorted proportions, and a sleepy Man in the Moon, interwoven together as if part of some fantastical dream. A plaque near the fountain states that the “Peace Fountain celebrates the triumph of Good over Evil, and sets before us the world’s opposing forces–violence and harmony, light and darkness, life and death–which God reconciles in his peace.”

The contrasting imagery of good and evil the artist conveys with the Peace Fountain statue pushes the observer into a confusion of perception to challenge the mind. This chaotic representation of “the world’s opposing forces” shown in the statue has become a symbol for me of what Seth Godin describes as the resistance: the anxiety born from the risk of failure when sharing something original with the world. Seth Godin explains in his book The Icarus Deception: How High Will You Fly? that in order to create meaningful art “the artist seeks out the feeling of resistance and then tries to maximize it.” [1]

Jason Freeman is the founder of Work of Start.

1. Seth Godin. The Icarus Deception: How High Will You Fly? (New York: Portfolio/Penguin, 2012), 133-136.

Protective Armor Against Terror

How meeting one of the victims of the Boston Marathon bombing changed my perspective on studying history through art.


Art studies the world, in all its manifestations, and renders back to us not simply how we see, but how we react to what we see and what we know as a consequence of that seeing.
– Kit White [1]

A few weeks after the Boston Marathon bombing I was, much like the rest of the community in the Boston area, trying to get back to life as normal. This “normal” activity included going to a bakery one Saturday morning for breakfast and a session of drawing. The seating area in the bakery was busy and after purchasing a bagel and cream cheese I began to hunt for a spot to sit down. Upon seeing an open table right next to a gentleman sitting quietly with his coffee, I rushed over to set the food tray down in order to stake out the spot. I noticed the man at the neighboring table had severe injuries to both arms, and I immediately got the impression this person would be open (not always the case in Boston) to a friendly gesture.

For several minutes, while working up the courage to offer half of my breakfast to a stranger, I began to draw in my sketch pad the next in a series of illustrations inspired by a samurai armor exhibit at the Museum of Fine Arts in Boston (please see Contributing to the Conversation). The noise of the busy bakery made the offer to share breakfast hard to hear, but the man at the next table understand my intention and graciously accepted half of the bagel. It was several more minutes before he very politely interrupted my drawing with a wave—I had by that time put in earphones—to share that his injuries had come from the Boston Marathon bombing.

We sat in conversation for ten minutes or so about the extent of the injuries suffered– a nearly detached hand and severe ongoing headaches– as well as discussing the medical treatment received over the prior weeks. He explained that the physical trauma was devastating, but there was also a constant mental anguish about reliving the experience in memory. My heart went out to this man as he shared his struggle to cope with the after effects of such a terrible ordeal. It turns out that on the morning of the attack he was in the very same bakery where we were sitting, and the staff had wished him well before he went off to the marathon festivities.

Once the story was finished we did not speak again until the man got up to leave. As he was collecting his various bags and items, I offered him one of the samurai drawings with the grand hope that the armor depicted could act as some symbolic shield to the mental trauma, or at the very least some small distraction.

Jason Freeman is the founder of Work of Start.

1. Kit White. 101 Things to Learn in Art School (Cambridge, Massachusetts: MIT Press, 2011), 6.

Contributing to the Conversation

A lesson from Kit White: how creating art adds to the historic dialogue.


Art is a continuing dialogue that stretches back through thousands of years.
– Kit White [1]

My favorite spot to visit in Boston is the Museum of Fine Arts. This place has numerous opportunities to get lost in rooms full of spectacular artwork. While wandering through the MFA I have discovered art from around the world, which many times has traveled to this place and time over hundreds, sometimes thousands, of years. The last trip to the museum offered the chance to see a new exhibit, “Samurai! Armor From the Ann and Gabriel Barbier-Mueller Collection,” and I acted on some inspiration to draw–this was my first time drawing at the museum–some of the samurai armor on display.

While I was drawing quietly in front of a magnificent suit of armor (shown above) an art student from a local university came over to see the sketch. He seemed very thoughtful and interested, so I offered him a pencil and paper. This offer was eagerly accepted and we both sat quietly working for the next ten minutes or so. After finishing the drawing he gave a sincere thanks and went on to explore the rest of the collection.

There were many objects that caught my attention, and by the end of the exhibit the original sheet of paper was filled with a half-dozen sketches.  I was sitting on a bench in front of the final display when an older gentleman came over to chat. He had trouble talking and hearing, but it was surprisingly easy for us to connect over the beauty of the samurai exhibition. As the conversation gradually came to a close  it  became apparent in my mind that this man should have the drawings. The gift was happily accepted.

The opportunity to connect over artwork with strangers at the MFA reminded me of a lesson from Kit White in the book 101 Things to Learn in Art School. Art is the opportunity to make “…your contribution to that dialogue. Therefore, be conscious of what has come before you and the conversation that surrounds you.” [1]

Jason Freeman is the founder of Work of Start.

1. Kit White. 101 Things to Learn in Art School (Cambridge, Massachusetts: MIT Press, 2011), 16.