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A Missing Piece of Entrepreneurship – Oliver DeMille

determinedyoungmanI write a lot about entrepreneurship, even though my main focus is freedom.

The reason for this is simple: free nations are always nations with a strong entrepreneurial sector. There are no exceptions in history.

Put simply, the great free nations of human experience had a flourishing free enterprise. This was true in ancient Athens and ancient Israel, the Swiss free era and the Frank golden age, the free periods of the Saracens and also the Anglo-Saxons, the American founding era and the modern free nations of Britain, U.S., Canada, Japan and Europe, among others.

Take away free enterprise, and a nation’s freedom always declines. Shut down the entrepreneurial spirit, and liberty rapidly decreases.

The main reason freedom rises or falls with entrepreneurialism is simple:

  1. To succeed as an entrepreneur, a person must exhibit the character traits of initiative, innovation, ingenuity, creativity, wise risk-taking, sacrifice, tenacity, frugality, resilience, and perseverance.
  2. These characteristics are precisely the things that through history have proven necessary for free citizens to stay free.

The large majority of responses when I write about entrepreneurship are thoughtful, insightful, and even wise.

But once in a while when I write an article pointing out the importance of free enterprise and entrepreneurship to freedom, I get a strange response. I call it “strange” because it shows that some people don’t quite understand what I mean by entrepreneurship. Such comments go something like this:

“I’m a born entrepreneur, and I’ve started dozens of businesses, so I understand that…”

“I have a list of ideas for successful entrepreneurial projects — could you suggest which of these might be the best options…”

“My spouse is constantly starting entrepreneurial ventures and using up our capital in such schemes, and your article made him want to do several more of them…”

These types of sentences are a real head-scratcher. Why? Because this isn’t what successful entrepreneurship and free enterprise is all about. Not at all.

Successful entrepreneurs typically start 2-4 businesses during their life, not dozens, and at least one of them becomes an important enterprise. The free market just doesn’t reward people who start dozens of businesses, frequently jumping around from business to business.

People who are constantly engaged in their latest “start-up” aren’t really following the entrepreneurial path. They’re just endlessly repeating the first part of it. Free enterprise rewards those who stick with a business until it becomes a real success, or who learn from the mistakes of the past and then stick with the next venture until it truly prospers.

A lot of successful entrepreneurs have had a failure or two, but not many of them have spent their years working on dozens of businesses. They soon learn to pick one and do what it takes to succeed. They buckle down and go through the process of turning their company into something.

In fact, many successful owners have suggested that it takes about 10,000 hours, or even more, to become good enough at a business or economic sector to make it profitable. Those who are constantly jumping around just can’t ever get there.

When people talk about an entrepreneurial attitude or viewpoint of always starting another business, that’s one thing. But it’s not the same thing as tenaciously persevering until one business flourishes — and then tenaciously persevering as it keeps thriving.

This latter approach is the kind of entrepreneurship that builds a nation. It’s more than just a posture or a habit of starting a bunch of businesses. It’s more than liking the idea of business ownership. It’s more than talking about being your own boss.

It takes an incredible amount of hard work and tenacity to make a business truly work. Nothing else really gets the job done — for entrepreneurship, or for freedom.

This might seem like a little thing, like a meaningless play on words, but it isn’t. It is huge!

Entrepreneurship doesn’t spur liberty in a society just because some people have an independent, “I’ll do it myself” or “I’d rather be my own boss” attitude. That’s part of it, but there’s more.

Free enterprise is great when the enterprises work. This happens only when the small business owner pays the price to become a successful leader and make the enterprise blossom and grow.

Again, this might not always occur — and it never comes easily — but the leaders who build a free nation are those who hunker down and do the hard work to make it happen. Even if they fail, they make it happen the next time. One dedicated day at a time. Through all the hard times and challenges. Even when everyone else would have given up.

A nation with a lot of such entrepreneurs has a real chance at freedom.

A nation without them never does.


odemille Oliver DeMille is the New York Times, Wall Street Journal and USA Today bestselling co-author of LeaderShift: A Call for Americans to Finally Stand Up and Lead, the co-founder of the Center for Social Leadership, and a co-creator of TJEd.

Among many other works, he is the author of A Thomas Jefferson Education: Teaching a Generation of Leaders for the 21st Century, The Coming Aristocracy, and FreedomShift: 3 Choices to Reclaim America’s Destiny.

Oliver is dedicated to promoting freedom through leadership education. He and his wife Rachel are raising their eight children in Cedar City, Utah.


  1. Was the gap widened or narrowed by this article?


    The “types of sentences” that have you perplexed do seem to show that many individuals do not understand what it means to be an entrepreneur. But it seems to me that following the head scratching there might be place for filling in some gaps between being a “wantraprenuer” and a productive individual. Is it possible that the gap, instead, may have been made even wider by describing the tenacity of a Steve Jobs or stick-tuitiveness of a Tony Hseih.

    I believe that individuals can be true entrepreneurs and not have to stick with one business or idea (or two to four, for that matter). There are different ‘parts’ of entrepreneurship, and if an individual finds he (or she) can prosper in any one of the segments, he’ll flourish individually while increasing prosperity in his community, state, and so on. AND, I believe, he can effectively call themselves ‘Entrepreneurs.’

    If a person is talented at starting businesses and can better fulfill his or her own self interests by starting and selling businesses, then that is what they should do. Others may have talents for buying businesses, ideas, or innovations that have been proven and be able to take these toward greater prosperity. Others, still, may have a talent for buying into businesses that are hurting and turning them around (Marcus Lemonis, Bain Capital come to mind). I believe anyone proficient in any of these (or other) segments of entrepreneurship, then they are indeed entrepreneurs.

    (The argument can then be made that working in a given segment IS the entrepreneurial enterprise, not the ideas or businesses that are passing through the process. This would be correct, of course. But the article’s description appeared to ward off one’s focusing on segments in general — or, at least, starting multiple businesses).

    Certainly there is a gap between what I’ve referred to as the wantrapreneur and what I’ll call the “Segment Entrepreneur”, but I think it’s a smaller one. In either case, I’d like to see this gap shrink even further by seeing more information on getting from the wantrapreneur stage to the “I’m making money, exchanging value for value” stage; and from there to being economically independent, and further on.

    One challenge with filling these gaps is that many successful entrepreneurs are busy, and often writers can only observe and interpret. However, there are those entrepreneurs out there who want to see more entrepreneurs, who see entrepreneurship as a path to ensuring, growing, and promoting freedom (I’ve plans to pursue championing entrepreneurial education myself, but I want to ensure my own house is in order, first).

    Oliver, I enjoy your articles. Also, we’re starting TJED this year. Keep up the great work.

    ~Dave Charbonneau

  2. Oliver,
    I love your emphasis on character traits needed to build a free nation!
    Who we are and how we act really matters in the end. It is up to the individual to make great choices (win-win choices) to build businesses and freedom. It takes a lot. Keep encouraging us!

  3. btw,
    My friend has started an entrepreneurial club for young adults. We take them thru the business building process with a real business. The goals include developing character such as you mentioned, business skills and life skills and abilities. She wants me to read this article to all the young adults tonight at our meeting. Thanks again.

  4. Hunting.Targ says

    I have to say, that it wasn’t your article, but Dave’s opening paragraph, that really unpacked the issue for me.
    ‘Wantrapreneur’ is a great term, I think, and helps explain the astronomical failure rate of small business in America. I do not know, but I have a doubting suspicion that 18th-Century North America had the same failure rate; most of the time people simply couldn’t afford to fail in business, because it was their means of survival. When you’re working to ease your circumstances, it’s not that difficult to stop early, take a rest, and engage in reassuring speculation that one doesn’t have to work quite so hard, so long, that success will somehow cross the finish line and meet you partway. People working to survive do not have such thoughts. When failure means starvation or slavery, self-delusion is hardly a problem. As Seth Godin would put it, when it’s a matter of survival, your amygdala, your lizard-brain, gets very loud and screams at you to take action. Without that survival imperative, its easy to throttle down and become lazy. That’s what visualization is about; replacing that survival motivation with an imperative from the other side of the brain, a visual image that stimulates the desire to excel and win.

    The other word in that paragraph that I found stimulating was ‘stick-tuitiveness’. This is a very personal word for me, because I heard it many times growing up. It was espoused as a necessary quality, almost a virtue. It was something that I was often told I needed more of. What seemed to get overlooked and dismissed was the fact that from 7th to 12th grade, I went from being a C and D student (there were even a couple Fs in there) to being an A and B student, taking the most challenging classes, studying all on my own, and still taking part in community activities.
    I do not say this to sound my own horn, but to illustrate a point. Many would say that this is worthy and commendable. But I do not remember hearing it. After many disciplinary episodes, I made the decision, despite my consistently negative feelings, to work towards the top. The reward I got for my effort was not praise, but neglect. And I still heard about the need for ‘stick-tuitiveness’ now and then. This is not intended to be a personal expose, but a personal illustration. My efforts were not motivated by fear; my personal choice to excel academically was born out of a desire for recognition and acceptance: I wanted to REACH something, not AVOID depression and delinquency. I was positively motivated; and still I heard ominous reminders about that ‘stick-tuitiveness’. Many years later, I realized that what I heard was borne out of the expectation that I would eventually -have to- become like those guiding me; that I would -have to- get a job and run the rat race, that I would -have to- (insert cultural paradigm), because that’s what everybody else in the family did, because ‘that’s just the way it is’, ‘that’s just what you gotta do’. To those counseling me, ‘stick-tuitiveness’ meant doing what was expected by peers or society, no matter how unappealing or unnatural it might seem.
    Horse manure.
    The main benefit of survival thinking is that it forces you to take action. The main drawback of survival thinking is that it forces you to take action at the expense of imagination and creativity. The proliferation of employeeship has affected the West in many ways, not the least of which is that it has reinforced survival mentality by proscribing fixed ‘slots’ or niches of opportunity within a defined structure. This initially placates both the lizard-brain and the imagination (more technically, the amygdala and the Pre-Frontal Cortex), and may even stimulate the latter; but as time goes on, when the burdens of life weigh more and more heavily on a fixed opportunity, the lizard-brain starts to speak again, exerting the pressure to act; and we tend to act within the system, without much creativity or ingenuity, without looking for alternatives to the situation of being someone else’s paid servant.

    To tie it all together: My interest in Dave’s two terms is in understanding why the majority of people don’t ‘see’ entrepreneurship as an alternative, and why most who do don’t put in the effort to make it work: They’re seeking to survive, not succeed; they’re dreading failure, not dreaming of winning. The Fifth Law of Decline, the Law of Inertia (or the ‘doom loop’, as Jim Collins called it), is what pushes people into survival thinking and away from entrepreneurial thinking. This is not the only reason for the slim success rate of entrepreneurs, but I think it is an important one. What tends to not be understood is that fighting inertia and natural inclinations isn’t important only for the moment, but over the long haul as well; that’s what ‘stick-tuitiveness’ REALLY means.

    Reposted at http://huntingtarg.wordpress.com/2014/08/04/the-real-struggle/

  5. @Dave Charbonneau: “(The argument can then be made that working in a given segment IS the entrepreneurial enterprise, not the ideas or businesses that are passing through the process. This would be correct, of course. But the article’s description appeared to ward off one’s focusing on segments in general — or, at least, starting multiple businesses).”

    Well said! I totally agree with this. Good clarification!


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