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Affluent Christian Investor | September 19, 2017

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Malcolm Gladwell of David and Goliath: An Entrepreneurial Dilettante?

David gegen Goliath (Painted by Gebhard Fugel) (turn of the 19/20th century)

David gegen Goliath (Painted by Gebhard Fugel) (turn of the 19/20th century)

Malcolm Gladwell’s latest book, David and Goliath, is a typically-intriguing array of interesting anecdotes, tales, and research reports strung together by a thread, very thin at times, that makes for good airplane reading. At various points throughout his book, he refers to entrepreneurs, innovators and “creatives.” Is this useful or misleading? Does his approach reflect knowledge or superficiality? Is he an expert or a dilettante?

The subtitle of the book is “Underdogs, Misfits, and The Art of Battling Giants.” The gist of the book is that perceived disadvantages may in fact be advantages in some ways and in some circumstances, that misfits develop important coping skills that help them succeed in life, and that battling giants is possible because giants are not always as powerful as they appear to be.

The highlight of his latest book is relates to the title. No one will likely think of the tale of David and Goliath the same way ever again. Goliath never had a chance. I won’t spoil it. Read the book and find out why.

I want to focus on how this book relates to entrepreneurs. Gladwell discusses the concept of “desirable difficulties” (p. 102). Gladwell focuses on one particular disadvantage.

“An extraordinarily high number of successful entrepreneurs are dyslexic.” (p. 106).

A recent study at City University London puts the number at one third (p. 106). Gladwell’s basic idea is that they work very hard to overcome their difficulties

Gladwell focuses on another dimension: “Dyslexics are outsiders as well.” (p. 115). The “outsider dimension” is a common component of entrepreneurs, who typically challenge conventional wisdom and think outside the box. This is, of course, much easier as an outsider—you have no fear of being outside the box or caring about a disapproval of a peer group. Gary Cohn, President of Goldman Sachs, who is dyslexic, says,

“our [entrepreneurs] ability to deal with failure was very highly developed.” (p. 123)

Mainstream academic research and my own with 100s of entrepreneurs indicates clearly that there are often elements in their backgrounds that provide added incentives to strive for success. Often entrepreneurs grew up poor—and vowed they would not relive that experience. In other cases it was lack of education or of high-quality, gilt-edged education—so they had a chip on their shoulder to show others they could succeed. In other cases, they were immigrant kids who were classic outsiders—they didn’t understand the customs and language of the new country and thus buckled down to succeed. There are many factors.

Gladwell refers to another apparent disadvantage.

“In the early 1960s, a psychologist named Marvin Eisenstadt started a project interviewing “creatives” –innovators and artists and entrepreneurs-looking for patterns and trends. A surprising number had lost a parent in childhood.” (p. 140).

The main point: this is not an argument for orphanhood and deprivation, but the existence of these eminent orphans does suggest that in certain circumstances that a virtue can be made of necessity (p. 143). This is not new. A sad joke among entrepreneurs is that to succeed you need a dead parent who had excessively high expectations—you will spend your lifetime leaving up to expectations that cannot be matched.

Does being part of a particular peer group (i.e. other highly successful, well-educated people) provide some type of advantage? Gladwell explains:

“To answer that question, it is worth thinking about the kind of personality that characterizes innovators and entrepreneurs.” (p. 115)

Gladwell notes that

“The psychologist Jordon Peterson argues that innovators and revolutionaries tend to have a very particular mix of…openness, conscientiousness, and agreeableness.” (p. 116).

He further highlights:

“But crucially, innovators need to be disagreeable.” (p. 116)

Gladwell gives example of Ingvar Kamprad, founder of IKEA who was highly disagreeable (p. 117). He was disagreeable—and succeeded! One anecdote, no matter how interesting, does not provide a point.

Gladwell is a journalist and not an analyst, a storyteller and not a researcher. His strength is to focus on the counter-intuitive or to challenge conventional wisdom. His books often resonate with people because we recognize that his points ring true. The basic thrust of his book is worth a read.

On entrepreneurship, Gladwell adds no insights, but rather points out things that are common currency and well-trodden in the field of entrepreneurship. His points related to entrepreneurship, innovators and creatives, range from simplistic to misleading. Some might call him an entrepreneurial dilettante.

Gladwell makes a telling admission about his previous bestseller Outliers that he was in retrospect naive as,

“I was not familiar with relative deprivation theory at the time.” (p. 287).

He might be making a similar admission in his next book about this one with respect to knowledge of entrepreneurs.


Originally posted on Entrepreneurial Leaders Organization.

Richard (Rick) J. Goossen, BA, LLB, LLM, PhD., works with Covenant Family Wealth Advisors (Vancouver & Toronto) (, as a Relationship Manager and Strategic Advisor. He is Director, Entrepreneurial Leaders Institute, Wycliffe Hall, University of Oxford. He is Chairman, Advisory Board, Entrepreneurial Leaders Organization, which organizes the world premier events for Christian marketplace and entrepreneurial leaders. For information go to


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