startup principles, practices, and paradoxes

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Scholars have theorized while pundits have, well pundit-ed, about the phenomenon of entrepreneurship for centuries and yet we still struggle to agree over just what entrepreneurship is. Similarly, we have continued to disagree on just who or what is ”the entrepreneur.”

We have conceived of the entrepreneur, and in turn entrepreneurship, in many ways, only a few of which would be: an uncertainty-bearing economic agent (Cantillon, 1755; Knight, 1921); an “adventurer” (Say, 1834); a coordinator of labor, capital, or land (Marshall, 1890); the instigator of innovations that lead to creative destruction (Schumpeter, 1942); the enactor of a mindset (Timmons, 1989); the founder of new ventures (Gartner, 1985); the savvy bricolageur of otherwise disparate resources (Levi-Strauss, 1966; Baker & Nelson, 2005); someone who discovers, evaluates, and exploits opportunities (Shane & Venkataraman, 2000). As Kilby remarked nearly three decades ago, “Alfred Marshall’s fourth factor of production has proved very hard to nail down” (Kilby, 1983, p. 107).

Archetypes of the Entrepreneur

Five archetypes of the entrepreneur emerge from cultural mythology: gambler, gunslinger, grandstander, genius, and guru. Biographies and memoirs of (in)famous founders often suggest that success hinges upon one or more these characteristics, further supporting the myth that successful entrepreneurs are somehow special people from the start. As a result, these otherwise general traits are treated as either the genotypes for a select human species, or the basic building blocks from which the DNA of a true “entrepreneur” is coded.


The gambler is willing to act despite or in spite of the odds. Their behavior is the result of an undeniable preference for risky situations and (melo)dramatic leaps of faith.

The gambler archetype owes its origins, at least in part, to certain economic theories of entrepreneurship. If markets are assumed to be efficient (i.e., perfectly competitive, perfect information, etc.), then returns in these markets reflect the risk taken to earn these returns. In order to earn above-normal returns from their actions, entrepreneurs must either be (a) lucky or (b) be willing to take risk that most other people are unwilling to take.


The gunslinger never really fit in with society—or, more specifically, corporate society—and chose, inevitably, to go it alone and “be their own boss.” Gunslingers often shoot first and ask questions later, facing a adversity with a steely gaze.


The grandstander (often self-described as the gamechanger) loves to put on a great show. Their products or services are always disruptive, revolutionary, once-in-a-lifetome opportunities, that have never, ever been seen before.


Possessing extraordinary brilliance, the genius discovers opportunities few others have even noticed, and/or develops (usually technical) solutions that it seems no one else has been able to imagine. This brilliance is considered innate, or somehow refined through the sort of education appropriate for an innovator.

Like the gambler, the genius owes its origins to economic theory. If we relax the conditions of efficient markets and begin to assume information is not only asymmetrically distributed, but also imperfectly available, then the ability of the genius to access and interpret otherwise inaccessible or uninterpretable market signals becomes necessary for success. In other words, if this success is not purely by chance, then it must be the result of extraordinary insight or knowledge.


Indwelled with inexplicable understanding, the guru simply “knows” and acts accordingly—no tinkering, fumbling, or pivoting are required on the way to success. The guru’s innate awareness is often limited in scope, however, leading to various sub-species, such as: sales gurus, design gurus, product gurus, management gurus.

Most importantly, gurus can do no wrong. Any failure is seen as inexplicable foresight—the guru was simply ahead of the curve and had to wait for the rest of society to catch up.


For this collection of notes we are going to sidestep the various myths that surround “the entrepreneur.” We will avoid, as well, the effort to propose some new factor, mindset, or behavior that not only has evaded the understanding of scholars until now, but also would distinguish founders from the rest of the so-called “normal” people.

Instead of asserting that we have finally found that single kernel of something-or-other that is the essence of the entrepreneur, we will accept that these people and this phenomenon are complex—yet—commonplace.

Entrepreneurs are not special people at all, indwelled with an extraordinary sense of “the new,” persistence through adversity, or penchant for risk. Startups that make big news tend to operate at the boundary of new trends. People who have a greater tolerance for risk are simply more likely to take the risk of starting a new venture. Individuals possessing an overzealous drive to persevere simply have more time  to bump into something good — or bad — along the way.  

Starting a new venture may be a rare event, but the underlying raw stuff from which the urge to start something emerges is commonplace.  In fact, we will all start some thing, if not many things, during our lives.

And so, the notes herein are not about being an entrepreneur. These notes are about the art and science of starting something. This bundle of principles and practices that emerge from this mix of art and science will be called **enterprising, defined as: organizing unknown oppourtunity.

Furthermore, these notes should be seen as triggers for making sense of a challenge that has proven—at least for myself and many others—to be far less explicit than as pitched in many textbooks or bestselling business books. In other words, you are not about to be presented with a three-, six-, seven-, or twelve-step process for success and prosperity.

Instead, you are about to be presented with a bundle of principles and practices through which founders, funders, and average folks try to make sense of, succeed within, or just survive the startup challenge.