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Throughout history, entrepreneurs have faced harsh critics. From Shakespeare’s The Merchant of Venice through Oliver Stone’s movie Wall Street (“greed is good, greed works.” etc.) entrepreneurial efforts are cast in a dim light.

To paraphrase Lifebook founder Job Butcher, though, “no other social system can compete with the free market, entrepreneurial system in terms of productivity, raising living standards, and creating prosperity … Yet, despite its overwhelming contributions, some elements of society still associate profit-making with vice.”

To me, entrepreneurism is simply taking something that you are passionate about and turning it into capital so you can do more of it. Passion without monetization is called hobby.

I am what you would call a serial entrepreneur; I have tried (and more often than not, failed) at more businesses than you can imagine. Although failing is never fun, if you keep your mind open it will teach you more than success ever will. Here, I will discuss some characteristic of successful entrepreneurs and share a story or two about those traits.


Setting the integrity bar high is a must for the successful entrepreneur. At one point in our history, I had someone working for me who was the embodiment of hard work. She worked night and day and knew every aspect of the business. She just had two little issues.

The first was that she was like Chicken Little; the sky in her world was always falling, though she was always there to save the day. I learned over time that she devised dome of these tragedies so she could come to the rescue and prove her value. This trait, annoying as it was, was tolerable, at least for the short-term.

The other trait, embezzling, was the elephant in the room. She would enter one thing in the financial software, and then manually make the check out to her husband’s business. I eventually caught on. The problem was I was working day and night trying to mainline cash flow and took my eye off the books. Ergo, I was not detail-oriented. Such lack of attention, particularly during the start-up phase, can be disastrous.


Being visionary can be both a blessing and a curse. Decide if you are an innovator, early adopter, or superior operator.

The road to success is riddled with failed innovators. Who remembers the Altair 8800 personal computer? Or Atari, or the group (Seattle Computer Products) that sold DOS to Bill Gates for $75,000 (which, by the way, he did not have)?

Being an early adopter has some benefits. You let the innovator pave the way by educating the masses and hitting all the landmines. At the end of the day, a “superior operator” is something all entrepreneurs have to become to achieve any lasting success.

Unfortunately, many of the business ideas I have pursued have been “innovative.” For example, take the Vibrapon, which employs low-level vibrations to increase blood flow to muscle tissue, thereby relieving menstrual cramps caused by uterine contractions and lower blood flow to the uterus. I figured if a tampon could incorporate this small, non-disposable, removeable component, it would be a huge hit! I even had the first commercial written. “I used to hate that time of the month until I discovered the Vibrapon. Now I almost look forward to getting my period.”

Unfortunately, I learned that someone had already conceived and patented the Vibrapon, though the fact that no one has ever heard of it probably does not speak well for its success. lesson: You have to be non-risk averse to start a business and have the vision to see it through.

This also bears out an important tip: check the U.S. Patent and Trademark Office website ( before spending any capital on an innovative idea.


Pardon the vernacular, but if you want to be an entrepreneur you have to get your ass out of the chair and roll up your sleeves. Or, as I mentioned to one of our ED nurses who happened to be sitting in a chair for quite awhile while the ED sunk into chaos, “I am not sure if you have heard of Newton, but I can assure you, gravity will keep the chair from flying away if you get your rear end out of it.” Anyone can talk the game. Succeeding takes someone who is motivated to not just start a business but to see it through. Remember the old adage, if this was easy, everyone would do it.

One caveat: all the ambition in the world won’t save a bad idea. Or as the Successories poster says, “When you earnestly believe you can compensate for a lack of skill by doubling your efforts there’s no end to what you can’t do!”

A long time ago, I wanted to start a restaurant, I thought a good entry point would be to own hot dog stands. This all ended one day while working at one of the stands located in Home Depot. One of my customers said, “Don’t I know you? You served up my foot last week in the ER and you left some glass in it!” Fortunately, I had enough sense to say, “And that’s why I am selling hot dogs today.”

The next day I sold the business. No matter how ambitious I was, selling hot dogs was not going to provide the returns needed to grow the business and have lasting profitability. Nor could I bear to wear that stupid apron anymore!


I am optimistic to a fault. I am sure it irritates the rest of the team. I compare everything bad to the emergency department. “If no one is dying, how bad can it be?” In my time, this attitude has driven at least one CFO to insanity (though I think she may have already been DSM3 diagnosable).

Anyway, at one point of my business life we were trying to grow the business with very little capital. In 1995 I had the brilliant (not really) idea to franchise the concept. After two years, I thought we had a pretty good operating model that could be reproducible in other markets.

In essence, we adapted to our lack of capitalization by selling our platform. We learned, however, that providing healthcare is not a model which is easily franchiseable, mainly because there is no way to protect your brand. One bad apple could destroy the entire entity by providing less than acceptable service or care.

One day, while we were slugging it out trying to promote this concept, someone from Wall Street Journal left a message for me to call him as soon as possible. I thought that we were finally going to get some recognition for this, at the time, ground-breaking idea. After three days of phone tag. I finally got a hold of him. “Dr. Shufeldt, it is great to finally get to speak with you. Would you like to increase your subscription from one year to two?”

Needless to say, I remain optimistic.

Sense of Humor/Humility

A sense of humor keeps an entrepreneur sane. Failing to see the humor in all the crazy things you will experience (such as a provider who locks himself in the bathroom and threatens to start drinking) will make the ride much less enjoyable.

In healthcare, a lack of sense of humor can be your undoing, I cannot tell you how many times I have looked around an exam room for the Candid Camera film crew, believing that the only explanation for what a patient just said was that I must be getting “punked.” (Wait, you were standing on a bridge huffing paint and then you fell off the bridge and only broke your ankle and then stood up and were struck by a truck?”)

The challenge with arrogance is twofold. Everyone loves to see arrogant people fail and will often go out of their way to not help an arrogant person. As the late Notre Dame football coach Frank Leahy said, “Egotism is the anesthetic that dulls the pain of stupidity.” Arrogant people are usually deeply insecure and as such will never take risk that could result in being viewed as a failure. The most competent people I know are also the most humble.

The goal of any entrepreneur is to make a contribution and to be paid a fair price at some time for the business. However, the most important advice I can offer is this: While the payout is great, the fun is in the ride, not arriving at the destination. See you up the road!

Entrepreneurism—Or, How Not to Turn a Lot of Money into a Little

John Shufeldt, MD, JD, MBA, FACEP

Chief Executive Officer at MeMD, LLC, Mentor and Author at Outliers Publishing, Principal at Shufeldt Consulting, Founding Partner of Shufeldt Law Firm