All posts by Jason Freeman

Responding to ‘Tough Times U’

When you choose to be in a startup, you’re enrolling in the school of tough times. My time as an entrepreneur has been no exception. Now on my third startup, I had a chance to reflect recently on some tough times from my first entrepreneurial experience.

Responding to tough times

Ray Kliewer passed away on July 11th, 2009. Ray was one of the cofounders in my first startup.

I first met Ray along with his management team in the spring of 2008 at the headquarters of the engineering company he started nearly 25 years earlier. The meeting was organized by my MBA classmate to present a new product idea to their group. Our hope was to explore a partnership with Ray and his team, which included son Jay Kliewer, knowing their strong reputation and expertise (environmental, health, and safety regulation compliance) in the business problem we were trying to solve.

Ray, Jay, and team were open to the exploring the idea of a partnership and not long after the first meeting we formally partnered to develop a new compliance reporting technology. The passing of Ray nearly a year after partnering was very challenging. During that tough time, I remember being impressed by Jay’s strength when he stepped up to run the company his father started nearly a quarter century earlier.

Around this same time, I recall reading The Breakthrough Company byKeith R. McFarland. In his book, McFarland talks about responding to adversity in the chapter titled “Graduating from Tough Times U.” He shares that:

“…[I]t is not the surviving of tough times that defines a breakthrough company; rather, a breakthrough company is defined by how it uses those tough times to adapt, learn, and redefine its thinking.” [1]

Observing how the company his father started rallied around Jay as a leader was a powerful thing to see. It’s been even more impressive to watch Jay live up to that responsibility by advancing the company into new opportunities and growth in subsequent years.

Partnership grows stronger

Thankfully, our year old startup had formal agreements in place to handle the loss of one of our founders. It’s now remarkable to look back and recognize that our preparation for the unexpected can be greatly attributed to Ray’s foresight and experience. Because of this prudence, our cofounder group was able to come together and stay focused on creating a business and, united as a team, we believed the best tribute to Ray would be continuing to build something valuable.

It’s because of this challenging time that it was possible to truly see the type of people I had partnered with. These are good people. As McFarland also observes:

“Nothing quite brings out the truth about one’s character like difficult times.” [1]

My first entrepreneurial experience was a chance to learn through “Tough Times U.” I’m very grateful for the opportunity to grow with an amazing team during that challenging time, and likewise, I’m so very lucky to have a wonderful team during my current startup experience.

Keith R. Mcfarland. The Breakthrough Company: How Everyday Companies Become Extraordinary Performers (New York: Crown Business, 2008), 189, 191.

Developing Your Influence

I discovered early on when learning to oil paint that applying background color was important to forming a complete painting. That discovery was true even when the underlying paint could not be consciously seen– somehow the background color comes through. A similar phenomena is true for influencing others, whether it’s during a casual conversation or public speaking with a large audience. When talking on a subject, it’s the in-depth understanding of a topic which offers a real chance to influence others. And, the things that go unsaid (the background paint) is just as powerful as that which is spoken.

Building a Business from an Idea

There is a time in a startup when an idea becomes real. It’s quite an odd, almost jarring transition. One day your relying on a abstract belief or leap of faith to push forward and the next you have something tangible. There are various triggers for a change in perspective: validating some core assumption of the business, bringing in revenue, and obtaining investment are all perspective changing events. Additionally, it may be that others are willing to commit to the idea such as securing a true cofounder or channel partner. The point is, a startup founder should wake up the next morning and say “things are different today…this just got real.”

A Break from the Ordinary

There is nothing like having a break from your ordinary routine—for me this break is quite literally a broken ankle and foot—to see things a little differently. My break happened with an unfortunate accident at my local fight sports gym during a wrestling class, and it required a trip to Mass General Hospital for some surgery. And with a mix of snow and required elevation I’m, for the most part, bound to the apartment for the first couple weeks after the injury.

This time has given me a chance to see my startup team step up and keep our company moving forward. They not only have taken on extra load during my unexpected absence but also have tried to make it more comfortable for me to get back into the work routine. This accommodation includes the group coming and setting up shop from my apartment on many days.

Having a work team that will stand by you through challenges seems uncommon in this world, and it took a break from the ordinary to appreciate just how lucky I am to have such a luxury.

Three Critical Elements for Building Innovative Teams

Building a startup offers the chance to work alongside people so passionate that they are willing to sacrifice professional certainty. That certainty sounds like “I’ll get my raise this year with a good performance review,” and “if I just put in the time I’ll get that promotion.”

Why sacrifice professional certainty?

In my experience, people will give up their sense of certainty to follow a belief that their world should change. And it’s when people come together to work around a common belief that extraordinary collaboration can take place.

In the book Midnight Lunch: The Four Phases of Team Collaboration Success from Thomas Edison, Sarah Miller Caldicott describes the power of collaboration through studying teamwork in the famous Menlo Park Laboratory, founded by Thomas Edison. Describing teamwork in Edison’s lab, Caldicott states:

“…[True collaboration] embraced both the uniqueness of the people who engaged in Edison’s team efforts as well as their deeper, shared experience in laboring toward a common purpose.” [1]

 Element One: Share a common purpose

The common purpose, (often referred to as an organization’s mission) described by Caldicott is the first and foremost element of building a team. A bond of shared purpose offers the strongest link for startup founders, just as it was for Edison’s team, and it can sustain the group through the toughest of times.

As a short break from the challenges of startup life, my startup cofounders and I recently had the opportunity to visit The Museum of Fine Arts in Boston as a team one afternoon. During this visit, we saw John Singleton Copley’s “Watson and the Shark,” one of my favorite paintings on display.

Watson and the Shark by John Singleton Copley

Acquired from Boston Museum of Fine Arts Website ( on February 13th, 2014

Copley’s painting shows the dramatic scene the moment before a shark takes a young swimmer’s leg. The victim of the attack is a cabin boy named Brook Watson who grew up to commission Copley to create the painting.

“Watson and the Shark” is a beautiful piece. What I appreciate most about Copley’s painting is the common determination displayed by the rescuers in the boat, each playing their part to save Watson from the attack.

Element Two: Empower unique talents

Just like Watson’s rescuers, individual members have to play a unique part in order to build an innovative team. To play that part effectively, a team should focus on empowering individuals to apply their own unique talents and strengths.

The concept of playing to people’s unique talents and strengths is simple, but it’s contrary to much of what we are taught in today’s world. For the most part, we’re all encouraged to improve on our weaknesses instead of identifying those ingrained and innate talents in each of us.

Fixing weaknesses isn’t the best way to develop a team capable of innovation. As Marcus Buckingham and Donald O. Clifton identify in their book Now, Discover Your Strengths:

“Most organizations take their employees’ strengths for granted and focus on minimizing their weaknesses. They become expert in those areas where their employees struggle, delicately rename these “skills gaps” or “areas of opportunity,” and then pack them off to training classes so that the weaknesses can be fixed.” [2]

Buckingham and Clifton go on to make the argument that—as learned through extensive research—truly successful people owe that success to “…their ability to discover their strengths and to organize their life so that these strengths can be applied.”

By working through the enormous challenge of innovating, individuals test and build on their talents, and have the opportunity to turn innate talent into actual strengths. The terms often used for this type of individual development is to be “refined by fire” or “battle tested,” and it’s the third critical element for team building.

Element Three: Overcome challenges together

A team that’s battle tested has individuals who have been through challenges and have learned to work together through these tests of strength and determination.

In the search for a group that overcame enormous and sustained challenges, there are few better examples than how British citizens stood up to the tyranny of Nazism during World War II. Their defiance sustained through devastating air raids on Britain by the Luftwaffe’s bombers. If fact, as the destruction sustained, it has been well documented  that the nation’s resolve to stand as one only increased.

Thankfully, a startup that is trying to innovate will not face the same challenges as British citizens had in World War II during the bombing of their cities. That being said, the impact of moving through tough times as a group cannot be understated, even if those challenges come from experiences such as bringing a new product to market or building a business around an innovative idea.

1. Sarah Miller Caldicott. Midnight Lunch: The Four Phases of Team Collaboration Success from Thomas Edison (Hoboken: John Wiley and Sons, Inc., 2012), 18.
2. Marcus Buckingham and Donald O. Clifton identify. Now, Discover Your Strengths (Gallup Press, 2013).

The Lean Startup Critique: Avoiding the Innovator’s Blind Spot

If you’re an entrepreneur, The Lean Startup by Eric Ries is a must read. This book has been established in startup lore (along with The Four Steps to the Epiphany by Steven Gary Blank) as the canon for entrepreneurs. My own thinking around innovation has been greatly influenced by this work, and I believe the methodologies outlined are absolutely worth learning and applying.

There’s another book I would like to add to the entrepreneur’s reading list: The Wide Lens by Ron Adner. I’m an advocate because Adner exposes an area of potential weakness in the lean startup methodology for the would-be innovator.

Avoidable Failure in The Lean Startup

Adner does not counter The Lean Startup central thesis that innovation requires “Validated Learning” [1] through experimentation, scientifically testing innovative ideas. He simply says that knowing the customer and developing a product using validated learning is not enough for the would-be innovator.

Using the term “Innovation Blind Spot,” [2] Adner describes when “…smart companies and talented managers invested, implemented, and succeeded in bringing genuinely brilliant innovations to market. But after the innovations launched, they failed.” [2] Adner argues this type of failure can be avoided. He goes on to discuss companies that fail to realize value through innovation:

“The companies understood how their success depended on meeting the needs of their end customers, delivering great innovation, and beating the competition. But [they fall] victim to the innovator’s blind spot: failing to see how their success also depended on partners who themselves would need to innovate and agree to adapt in order for their efforts to succeed.” [2]

Avoiding the Innovator’s Blind Spot

As readers of this blog know, I enjoy going to the Museum of Fine Arts in Boston. One of my favorite places to visit in the museum is the Impressionists section where you can see paintings from world-renowned artist (only needing a last name to recognize) including Renoir,  Degas, and, my favorite, Monet.

La Japonaise  - Camille Monet in Japanese Costume by Claude Monet in 1876

Acquired from Boston Museum of Fine Arts Website ( on January 2nd, 2014

Over the past year, one of Monet’s paintings was on display during a restoration process. The painting is called La Japonaise (Camille Monet in Japanese Costume), and during the restoration it could be seen from different viewpoints including upside-down, giving observers a fantastic opportunity to see the painting in a new way.

In the book, David and Goliath, Malcolm Gladwell talks about how the Impressionists had to find new ways to share their innovative, and often scorned, creations with the world. In his description, Gladwell calls the Impressionists outsiders who were repeatedly rejected by the Salon—the place where traditional French artists would be discovered and shown. Monet, along with other innovative artists, had to change tactics and display their work independently to be seen. Regarding Monet’s decision to find a way around the Salon, Gladwell states:

“We strive for the best and attach great importance to getting into the finest institutions we can. But rarely do we stop and consider—as the Impressionists did—whether the most prestigious of institutions is always in our best interest.” [3]

Monet had to avoid the innovator’s blind spot and see that relying on the Salon to adapt their exhibits to the Impressionists was folly. Like Monet, entrepreneurs must also understand the bigger picture when trying to create something new which requires working around, often difficult to see, obstacles to innovation.

1. Eric Ries. The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses (New York: Crown Business/Random House, Inc., 2011), 9-10.
2. Ron Adner. The Wide Lens: What Successful Innovators See That Others Miss (New York: Portfolio/Penguin Group(USA) Inc., 2013), 2-4.
3. Malcolm Gladwell. David and Goliath: Underdogs, Misfits, and the Art of Battling Giants (New York: Little, Brown and Company, 2013), 68.

Learning by Experimenting: When Just Doing is Not Enough

Innovation requires dedication to challenging the status quo. And, in order for the world to change through innovative thinking, new ideas must have impact and spread. These two statements are not ground-breaking, but they represent formidable tests of a would-be innovator.

It’s been my experience that aspiring innovators struggle with testing their own assumptions while dogmatically fighting to protect their ideas from being challenged. These untested ideas become the accepted truth for a would-be innovator. Regretfully, there have been many times in my own entrepreneurial career when I stubbornly stuck to flawed assumptions without testing whether an idea has a positive impact and can spread through the world.

Master artist remains a student

The Daughters of Edward Darley Boit Painted in 1882 by John Singer Sargent

Acquired from Boston Museum of Fine Arts Website ( on January 1st, 2014

One of my favorite paintings at Boston’s Museum of Fine Arts is the  “The Daughters of Edward Darley Boit” by John Singer Sargent. This oil painting is unique, capturing what feels like an impromptu snapshot in the life of four sisters. Displayed next to the painting are two tall vases shown in the piece, increasing the effect that you are looking at a real life scene and not a contrived sitting for a portrait.

In describing how innovative the painting was at the time, the MFA notes that:

“While some critics praised Sargent’s technical abilities, most found the composition troubling for its unconventional approach to portraiture.” [1]

Now showing at the MFA is a special exhibition of John Singer Sargent watercolors. Being a fan of Sargent’s other works, I was excited to see this temporary exhibit of more than 90 paintings.

The exhibition is arranged by the theme (as an alternative to arranging by date or location), so it gives visitors an opportunity to see how Sargent experimented and progressed as an artist. The notes next to the individual paintings also describe how Sargent worked alongside and learned from other great artists from that time.

Failure is important

As Eric Ries talks about in his book The Lean Startup, failure is critical to an entrepreneur’s progress towards becoming an innovator. Ries makes the point that an entrepreneur who cannot fail will not be able to learn how to succeed. He states:

“…If the plan is to see what happens, a team is guaranteed to succeed–at seeing what happens–but won’t necessarily gain validated learning.” [2]

Just as John Singer Sargent iterated and practiced on numerous sketches of the human form to refine his craft, so must an entrepreneur give form to true innovation through validated learning by experimentation and testing.

1. Acquired from the Museum of Fine Arts Boston website –
2. Eric Ries. The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses (New York: Crown Business/Random House, Inc., 2011), 56.