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Handling the Entrepreneur’s Conundrum

Anyone who has taken the leap and started a business faces challenges almost daily. Being an entrepreneur means, you are the CEO alright, but it means Chief EVERYTHING Officer when you first start out.


I can remember the days after I started my first enterprise. I had about 20 employees and my wife and I had to make runs to Sam’s Club after work to buy toilet paper for the bathrooms in our office. Then we had to stock it after dragging it in. There was no glory in doing that I promise you. But heck, it had to be done. We were a small business trying to grow.

Those of you who have been there know what I’m talking about. You start out with some little idea and you hope it takes off. As it begins to build momentum, you have to start making bigger and bigger decisions. The thing you hope for of course is to succeed at what you set out to do.

Growth as a business creates a conundrum for most company founders and start-up entrepreneurs. I call it the Paradox of Success. The very fact that you might be thriving creates the need for organizational change that is bigger than the founder’s mindset. A person must be willing to change from founder/entrepreneur and become a true CEO. The choice is to make that change or find someone who will do it for you (be CEO that is).

Here’s the Rub

There is nothing wrong with that model of change other than the founder’s willingness to give up such control. This is where the conundrum comes in. Most founders I’ve ever known struggle with the ability to relinquish control. They are control freaks by nature. That is why the idea became successful; the founder insisted that things be done a certain way all along.

Growth beyond the simple start-up phase demands a broader way of thinking. This is not to say you have to change the secret sauce or the product formula. Rather it says the way you go about executing on the production or delivery of the good or service has to change. Change is needed to handle the growth and keep things scalable and repeatable.

Have you ever known a quaint little bistro in your neighborhood that served “to die for” food? As soon as the owner tries to expand, the quality of the food suffers. There might be three times the tables, but the food is no longer the delicacy it once was. The same holds true for many businesses.

Staying stuck in the founder’s mindset can be death to a business. Failing to flex with success can work against you.

I am thinking of an experience I had with a regional firm who wanted to be national. They made their wealth in one particular segment of an industry but had visions for expanding into other, complementary services. The idea was great on paper, but the CEO had no idea what the truth was about those added services they went after.

There was some respectable success. Enough growth happened to fund some acquisitions allowing the company to be truly national, coast to coast presence. Yet several things started to happen.

First, the post-merger activities adding the other firms into the fold were a dismal failure of cultural clash. The two entities were not very well aligned in purpose and practice.

bright idea

More importantly, the founder felt his love for his original vision calling like the siren song. He could not support the expansion service visions from his own slanted view of the way things should be. The executives who were responsible for making the add-ons happen soon fell out of favor. As most high achievers will do, they left when the climate changed.

Enter the Smart Owner

The wise owner/founder is willing to reach beyond themselves; seeking advice and counsel along the way. Perhaps you establish a small core group whom you believe you can trust. Great things have been done with small, core groups. Jesus only had 12.

Yes, you can find great comfort in working with a smaller, trusted group. Yet I’ve still seen this fail. Why? Because the founder stayed deeply entrenched in his/her own narrow ideas. No, the wise founder will yield to greater strength in numbers, letting new blood take charge of the effort.

An owner/founder can still govern from a formalized seat as Chairman of the Board. As an enterprise grows, there is often a need to separate the person providing the vision from the one(s) responsible for day-to-day delivery or execution of the business. The founder is usually the vision person. Growth may dictate a need to expand the leadership team to bring in someone who can execute on the business.