Are You an Entrepreneur?

“You are forty, out of a job, a newlywed, your wife is expecting a baby, you don’t own your own home, you have no specialized qualifications, the only company you ever launched went bankrupt and you have just been sentenced to one year in jail.”

Source: Harold Evans, They Made America

Pop Quiz: Who was this person and what did they ultimately do with the cards dealt them? The answer is at the end of this entry.

Hint: He was an entrepreneur. Are you?

A Writer Is Someone Who Writes

A writer is someone who writes, not someone who goes about telling their friends that they are “a writer”. The same is true of entrepreneurs.

Robert Johnson, the famed Delta Blues guitarist, taught himself to play guitar by nailing various lengths of wire into the door frame of his parent’s shotgun shack. He was driven to play music, even though he could not afford a proper instrument. As he plucked the wires in the doorway, did Robert gloat to himself regarding his new-found musician status? Unlikely. He was too busy trying to make music.

Entrepreneurship is so highly valued in the Western World that some people try to convince themselves that they are an entrepreneur, when in fact they would be better off at a Big Dumb Company (“BDC”). These would-be entrepreneurs are best classified as Wantrepreneurs, as discussed in Entrepreneurial Enterviewing.

Wantrepreneurs were particularly prevalent during the Dot Bomb era when many folks who should have stayed well within The Herd. Most of these instant entrepreneurs were in it for one reason – quick money. As soon as the bubble burst and it was apparent that early retirement was not just around the corner, the Wantrepreneurs scurried back to their BDC cubicles.

Entrepreneur Does Not Equal Inventor

Some first-time entrepreneurs mistakenly believe that they are not entrepreneurs because they have never invented anything nor have they come up with a novel idea upon which a company could be built. I am firmly in this camp as well. None of the ventures that I have been involved in have been my idea, nor have I ever invented anything. However, these facts make me no less of an entrepreneur.

Only a small percentage of entrepreneurs are also inventors. Conversely, most inventors are not entrepreneurs. As discussed in Inventors vs. Innovators, most entrepreneurs iterate on preexisting ideas to the point that the inventions represent marketable value propositions upon which sustainable companies can be created.

If necessity is the mother of invention, obsession is the father of innovation. Innovations are often sussed out by entrepreneurs who cannot let go of an idea. As noted in The Fringe, most successful entrepreneurs are compelled to succeed by creating something from nothing, not by the lust for money, power or fame. ‘Creation’, not ‘conceptualization’, constitutes who is an entrepreneur and who is a dreamer. Dreaming is great, but if you never wake up and act upon your dreams you might as well stay in bed.

The Past Is Prologue

To answer the question, “Am I an entrepreneur?”, it is often helpful to look into your past. The actions of your youth, when you were not influenced by societies’ norms or the lure of wealth, may offer insight into your true desires and proclivities.

For instance, when you were growing up, did you partake in any of the following activities?

• Repeatedly organize yard sales in which you sold your broken toys, books you wrote and illustrated, along with overly sugared lemonade and burnt cookies

• Distribute gum / candy / school supplies from your locker in Junior High

• Master a musical instrument without your parents hounding you to practice

• Become proficient in a martial art

• Sell the most Girl Scout cookies each year and become depressed when the selling season ended

• Rebel against organizational hierarchies and resent being forced to take orders from someone just because they ‘put in more years’ than you

• Prefer to put yourself in situations where you could make an immediate impact, even it was in a ‘smaller pond’

• Hold several jobs in college, finish college early, and/or earn multiple degrees in less time than most people earn a single degree

• Excel at classes that interested you and perform poorly in those which did not

• Partake in high-energy, extreme sports

Falling Further From The Tree

It is not always relevant to look at your parent’s career and extrapolate your propensity to be an entrepreneur. One or both of your parents may have the personality of an entrepreneur, but if their parents were struggling entrepreneurs who put in long¬-hours and netted meager returns, then your parents may have rejected their latent entrepreneurial tendencies.

However, genetics certainly play a role regarding who is wired to become an entrepreneur and who is not. An alternative way to assess the relative depth of your entrepreneur gene pool is to think of extended relatives who were / are entrepreneurs.

To this end, ask your immediate family which relative they think your personality most resembles. Is it your Uncle Harry, the life-long government bureaucrat or Grandpa Jim who was a career door-to-door Fuller Brush salesman? If people who know you well think that you share traits with good old Uncle Harry, then you may want to think twice about leaving The Herd.

No matter whom you may take after in your family, perform a self-assessment and determine to what extent you exhibit the following entrepreneurial personality traits and characteristics:

• Sincerity
• Humility
• Honesty
• Naivety
• Impatience
• Optimism
• Influencer

This list may strike you as so much “Mom and Apple Pie”. However, these traits are shared by most successful serial entrepreneurs.


The origin of the word sincerity is, “without wax”. In ancient Greece, unscrupulous ceramic potters filled the cracks of damaged ceramics with wax. Once the repaired ceramic was painted, the wax was undetectable. However, when heat was applied to the ceramic, the wax would melt and the imperfections would become apparent. Clearly, buyers of such flawed ceramics felt cheated and wronged.

Successful entrepreneurs need to be “without wax”. As noted in Your Personal Pitch, entrepreneurs benefit greatly from relationships with Donors and stakeholders who can aide in the adVenture’s success. If your character cracks under the heat of a startup, your stakeholders will feel cheated, just like the ceramic customers in ancient Greece.


Winston Churchill was once asked if he was pleased that people filled large halls to hear him speak. He indicated that it was a nice feeling but that he also realized that twice as many people would come to the same hall to see him hang. Like a successful entrepreneur, Winston did not believe his own press clippings.

John Lennon once said that every time he began to think the Beatles were geniuses, he would look at Ringo and all such allusions were immediately dispelled. In fact, one of the most appealing aspects of the Beatles is that they remained self-deprecating, despite their enormous success. They seemed as surprised by their popularity as the reporters who covered Beatlemania. Their humility went a long way to winning over even the most jaded journalist.

Humility is the honey that will attract donors. As noted in Your Personal Pitch, people enjoy helping appreciative people who are in need. Hubris might be an entertaining trait for an entrepreneur in a Hollywood movie. However, in the real world, hubris will only make your journey more difficult.


As discussed in Time Wounds All Heels, successful serial entrepreneurs know that what Momma told them is true, “honesty is always the best policy”. Suppliers, customers and employees are more likely to support an entrepreneur and work with them to ensure their collective success when the entrepreneur honestly communicates the challenges they are facing.

To poorly paraphrase Abe Lincoln, you can screw some of the people some of the time, but you cannot screw all of the people all of the time. No matter where you launch your startup, it will be within the confines of a relatively small community of industry professionals who will frequently communicate. Every market, no matter how large it may seem from the outside looking in, is equivalent to a small town where the key players all know each other. In this small town atmosphere, dishonest people are quickly identified and reputable folks will eventually ostracize them.

Naïve and Not Courageous

I look with amazement upon our audacity in attempting flight with a new and untried machine”.

-Orville Wright

Entrepreneurs do not acknowledge limitations or barriers. They often have a naive view of the future - not Pollyannaish, but one in which failure is just not a potential outcome. Is it because they read a passage in a self-help book that told them to ‘wish away’ failure? – No. It is because they are too busy contemplating on all the opportunities that surround them to see the associated risks. Entrepreneurs have the audacity to believe that the odds do not apply to them, because they know they are going to win. If a world rich in opportunity and free of risk is a foreign concept to you, you might be well served by a career in accounting, insurance or the government.

If the typical entrepreneur acknowledged the risks and had the foresight to fully comprehend the work required to make their startup successful, they would be in immediate need of a defibrillator. In Mark Twain’s “The Adventures of Huckleberry Finn”, Huckleberry closes the book by saying, “…because if I'd a knowed what a trouble it was to make a book I wouldn't a tackled it…”.

Many entrepreneurs feel the same way at the end of their adVenture. Although they enjoy a sense of satisfaction, if they had known what they were up against at the outset, it is likely that they never would never have made the 'Base Jump' required to launch their adVenture. Entrepreneurs run through walls of fire without knowing what lies on the other side, constantly solving problems with minimal resources, inadequate sleep and a major case of bad nutrition. Does this make them courageous? Hardly.The definition of courageousness entails not being deterred from a particular action, even when you fully understand the associated risks. Entrepreneurs are not courageous. They are militantly optimistic, naive and compulsive. However, once the adVenture is launched, entrepreneurs often do courageous things in order to keep their adVentures float.


Nothing happens fast enough for an entrepreneur. Outside third parties may think the startup is moving at light speed, but progress may seem to move at a glacial pace to the entrepreneur. Do not despair.

The best selling book of all time (I’ll let you figure out the title) refers to life as a “battle” four times, a “race” three times and a “walk” over 400-times. Sometimes your adVenture will be a ‘battle’, sometimes it will be a ‘race’, but most of the time it will be a walk, a journey to be enjoyed and savored. OK, so maybe it will be a brisk walk (as compared with other vocations), but it will not be an out-and-out sprint, contrary to what many entrepreneurs believe when they first cast themselves out from The Herd.

Most ventures are marathons, not 100-meter dashes. No matter how fast and efficient you and your team are, products take time to develop, markets take time to mature and customers take time to understand and appreciate your value proposition. If you attempt to operate your adVenture in perpetual sprint-mode, you and your team will eventually run out of gas (emotionally, physically, or both), no matter how Herculean your stamina.

If you just read this and thought, “That advice is crap – my venture will be a nonstop sprint not a brisk walk”, then you may be an entrepreneur after all. Just as entrepreneurs are often in denial regarding the risks they will face, they also tend to believe that somehow their adVenture will be different and will not be forced to conform to the realities faced by everyone else.


There was once a pair of twins. One was a pessimist and the other an optimist. On their tenth birthday, their parents tried an experiment in which they hoped to temper the optimist’s Pollyanna view of the world, while encouraging the pessimistic child that sometimes good things do happen.

First they took the pessimistic child to their barn, which they had filled to the rafters with wonderful toys. To their dismay, the child began to cry. Through his sobbing, they learned that he was afraid that he would break some of the toys, that others would get lost and that some might be stolen.

Dismayed, they then took the optimistic child to his room, which they had filled with manure from the barn. Undaunted, the child jumped into the middle of the manure and began laughing as he tossed the manure in the air. The confused parents asked him why he was happy and through his laughter he said, “With all this manure in the room, there must be a pony in here somewhere.”

Successful entrepreneurs prepare for the best. They mentally pack a beach chair and sunscreen, not an umbrella and pepper spray. This approach makes the journey far more enjoyable. Entrepreneurs know that it is better to expect to find a pony in a pile of poop than to worry your way out of success.

Influence not Manipulation

One definition of a manipulator is someone who changes the behavior of others without changing their heart. Successful entrepreneurs change peoples’ hearts. Entrepreneurs lead by influencing their team, not by manipulating them. Manipulation might work in the short term but a manipulative management style will not result in sustainable results. Like the soldiers in Making Stone Soup, encourage people to follow you by welcoming their contribution to your adVenture’s ultimate success. Entrepreneurs must instill a belief deep enough for the stakeholders to pass the Blondin Test and figuratively place their livelihoods, fortunes, reputations, etc. on their back. If you manipulate people into following your lead, it is unlikely you will be able to sustain such manipulation for the duration of the average, four to six year, adVenture.

So Are You An Entrepreneur?

The most definitive way to determine your entrepreneurial status is to walk-the-walk of an entrepreneur. Create something from nothing. Fortunately, you do not have to quit your job and mortgage your house in order to live life on The Fringe. See Small Ideas, Big Benefits for suggestions regarding how you can test the entrepreneurial waters before taking the plunge.

Just as Robert Johnson did not waste time contemplating his status as a musician, if you are asking yourself if you are an entrepreneur, then the answer might in fact be “No”.

Answer to Pop Quiz

Thomas Watson, Sr. Founder of IBM – an entrepreneur who felt that the world only needed a handful of computers. Good thing Thomas Watson, Jr did not agree.

Interview Question Exercise
Draft five interview questions that you would ask someone in order to determine if they are an entrepreneur (see related entry, Entrepreneurial Enterviewing).

Post the questions and your brief answers as a Comment to this entry.

Do you think your answers indicate that you are an entrepreneur? If you are unsure, ask others whom you trust to evaluate your responses, including other John Greathouse readers.

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John Greathouse is a Partner at Rincon Venture Partners, a venture capital firm investing in early stage, web-based businesses. Previously, John co-founded RevUpNet, a performance-based online marketing agency sold to Coull. During the prior twenty years, he held senior executive positions with several successful startups, spearheading transactions that generated more than $350 million of shareholder value, including an IPO and a multi-hundred-million-dollar acquisition.

John is a CPA and holds an M.B.A. from the Wharton School. He is a member of the University of California at Santa Barbara's Faculty where he teaches several entrepreneurial courses.

Note: All of my advice in this blog is that of a layman. I am not a lawyer and I never played one on TV. You should always assess the veracity of any third-party advice that might have far-reaching implications (be it legal, accounting, personnel, tax or otherwise) with your trusted professional of choice.

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