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A Missing Piece of Entrepreneurship

A Missing Piece of Entrepreneurship

July 25th, 2014 // 7:38 am @

What Some Entrepreneurs Are Missing

A missing piece of entrepreneurship-Free enterprise rewards

I 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, and 2) these characteristics are precisely the things that through history have proven necessary for free citizens to stay free.

 The Hidden Problem

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.

 The Real Thing

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.

a missing piece of entrepreneurship-hard work and tenacity

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 amazing 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 A Huge Surprise! by Oliver DeMille 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

Category : Blog &Business &Citizenship &Community &Culture &Current Events &Economics &Entrepreneurship &Leadership &Liberty &Mini-Factories &Producers &Prosperity

4 Comments → “A Missing Piece of Entrepreneurship”

  1. Sylvia

    9 years ago


  2. Stephen Palmer

    9 years ago


    Part of me understands, appreciates, and agrees with what you’re saying here. Persevere, really succeed with entrepreneurship rather than being an entrepreneur-in-name-only, I get it.

    Another part of me is really balking, for a few reasons.

    First, it doesn’t really ring true with my experience. All of the successful entrepreneurs I know have done TONS of things before they found/created something that worked.

    They went through an apprenticeship period before learning what they needed to learn to be able to succeed.

    I think that with many of the entrepreneurs you’re speaking of who have only done 2-4 things in their life, if you were to really study it they did a lot more things before those 2-4 things that you see.

    If they are naturally entrepreneurial, many of them had several ventures as children and youth. Do you not count those ventures? It’s all about the learning. They simply had their apprenticeship period earlier than most people.

    I think the challenge here is that most of your audience are people who have never really done entrepreneurship, they’re older, and they’re inspired to entrepreneurship. But they didn’t have that natural apprenticeship period that the natural entrepreneurs had.

    So what you’re calling essentially flitting, I would say a lot of that is just a delayed — and necessary — apprenticeship period.

    Also, in most cases it’s necessary to get a lot of experience doing various things. It’s about strategic learning, rather than noncommittal flitting. It’s like Kiyosaki says, work to learn rather than to learn.

    (Also, if you haven’t read Mastery by Robert Greene, I highly recommend it. TONS of amazing content on all phases of mastery, including the apprenticeship phase.)

    Finally, a lot of people try various projects not because they’re noncommittal, but because they’re overly idealistic, or they lack the necessary knowledge and skills to make something work, or they simply don’t have a viable economic engine.

    So they quit and move on to the next thing when they realize that their project isn’t viable. (See The Dip by Seth Godin.)

    Perhaps I’m just speaking for myself and projecting my experience. Over the past 15 years, I’ve done tons of things. 2 years in financial services. Window cleaning business. Freelance writing. Self-publishing. Life Manifestos. Trying to build online businesses. Now building a network marketing business.

    I don’t regret any of these experiences — in fact, they were vital to my progression. I haven’t been flitting; I’ve been learning, growing, preparing. Failing in order to prepare myself for the big success.

    It’s actually a form of persevering. I have a vision in mind, I’m super clear on my purpose. With everything I’ve done, there’s been a strategic reason, and common threads. All of the experiences coalesce into one grand purpose.

    I don’t consider myself a successful entrepreneur yet by your definition here. But I know that my experiences have prepared me to be so, and I’m on track.

    But I NEVER could have just picked one thing and made it work. Maybe I’m too dumb, I dunno. I’ve just needed real-life experiences to figure out the whole entrepreneur thing.

    I just think you need to be careful with your characterization. I agree that too often people quit and flit when they should commit and stick.

    It’s also my experience that a wide range of experiences prepares us for ultimate success.

    Make sense? Thoughts?

  3. Stephen Palmer

    9 years ago

    Let me make this more concrete, with my personal experience.

    I was inspired to jump into financial services. I gave it everything I have for 2 years, including cold-calling. I learned a TON. Learned that it wasn’t for me. I didn’t quit, I moved on because it was the right thing.

    I was inspired to start a window cleaning business. I moved on when I learned the business well and realized that I didn’t want to scale a service business. I didn’t quit — I learned what I needed to learn from the experience and took that experience on to the next venture.

    My financial services experiences (among many other things) prepared me for freelance writing.

    I started Life Manifestos as an idealistic, passion-based idea. I had no idea if there would be market demand. I gave it everything I had for two years before realizing that it just is not a viable economic engine. (It will always be there, but will just never go big. Always a forever a side project.)

    See, I’m not a natural entrepreneur. I’m an idealist. True, natural entrepreneurs start by finding something with market demand. They look for the money. I’m just not built that way — it’s been a learned skill through experience.

    I couldn’t start to think like an entrepreneur without trying a few things and being forced to deal not with what I wish and hope, but what IS. Learning to accept reality as it is. I view my last 10-15 years as an apprenticeship period.

    But by your definition, I’ve simply been jumping from thing to thing.

    I really wish I had the natural aptitude for entrepreneurship. But I don’t. It’s been a long, hard road to figure it out, to think like a legitimate entrepreneur, rather than a wishful idealist.

    I think you need to stress that a “flitting” apprenticeship period is okay — so long as people stay committed to entrepreneurship, that they keep at it until they figure it out and really succeed. And don’t knock that vital apprenticeship phase.

  4. Oliver DeMille

    9 years ago


    I agree with everything you said, and would like to clarify one detail. We both agree that there is great learning that takes place in trial and error, and even in failure. This is not to be dismissed lightly, or undervalued. And yet, learning and earning are not usually the same process. The apprentice period doesn’t need to be taught, per se. Most people do it anyway. They don’t need it reinforced; they’re not going to move on until they’re good and ready, and to teach it, as such, is to perhaps give people a reason to stay in their comfort zone longer than is right for them, and not move past it. Those who have (like you and me) know that the apprentice period is helpful, but that the real magic happens once we focus and commit. So: you’re totally right! And, I wanted the message to be that financially, the success comes once a person focuses. And the sooner one focuses, the sooner the 2-4 endeavor pays off. Until then, it’s not fully-realized entrepreneurship, really; it is, as you say, practice entrepreneurship. Valuable, and related by degrees, perhaps. I think your clarification in the comments is great, and true. I just want the focus to be on entrepreneurship, not just the preparatory, gearing-up stuff that (and I know you’ve seen ’em too) so many people get stuck cycling through over and over and over. I’m hoping to poke the beast a little bit and get the journeymen to rise up and become masters. For all successful entrepreneurs, a time of focus must inevitably come.


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