Dreamers, Dealers, and Doers

by Bonnie Robertson

By cashing out of corporate-type careers or cashing in with savings we managed to tuck away, we are well on our way to one of the largest entrepreneurial booms in decades.  Whether the motives are frustration with managers that “just don’t get us” or ideas “that just won’t go away”, the drive for new start-ups or the remake of existing business is happening with renaissance-like enthusiasm. As usual, we celebrate the courage and creative innovation of entrepreneurs, although we rarely understand them.

In spite of the enthusiasm, the odds are not good.

More than 75 percent of new businesses fail within the first three years. It is not for lack of money or capital or hard work. Along with this rebirth of entrepreneurialism are those willing to invest financially and intellectually. So how do we improve the odds of us as entrepreneurs, our ventures, and those that support them? Recent surveys of venture capitalists attributed 65 percent of failures within their portfolio companies to the company’s start-up management teams and the entrepreneurs themselves.

With smart people, significant innovations, and available money, what are we missing in our analysis, planning, managing, creating, and sustaining of entrepreneurial companies? In more than three decades of working with, curiously studying, and learning from hundreds of entrepreneurs, I have come to the conclusion that understanding the primary personalities of the entrepreneurs themselves is key to leveraging opportunities as well as mitigating risks.

Meet the Personalities

People are too interesting to be pegged into “one” type of personality. Most of us have a mixture of traits that make us unique. We are also adaptable, which means we will change at times to better adjust or even to fight or flight. With this as a disclaimer, I have found that most entrepreneurs have stronger traits in one of three personality types: dreamers, dealers, or doers.


Dreamer entrepreneurs have an authentic “save the world” mission at heart. They are committed to making the world better in some way.  Dreamers are also visionary.  They see ahead and beyond in the market. They can “see” potential products or services that most others can hardly imagine – and, they can sell it.  Dreamers are excellent at convincing others along the way of their vision. Dreamers are at their best at the time of start-up or during the time of needed re-invention.

The danger zone for dreamers is when the business is functioning with a certain consistency, which can be viewed as boring. When dreamers experience boredom, they have a tendency to lose focus and follow-through. Dreamers have been known to create and re-create and re-create again and again in order to avoid solving a current day problem.


To a dealer, business is a strategic game. The type of product or service is not nearly as important as the opportunity to win – and make money. Dealers are in constant negation with all they come into contact with, team, vendors, customers, and the market in general.  Dealers use numbers to play their game of business and can often be found calculating formulas and scenarios on napkins in their quest to find the formula that results in true return on investment.  Dealers are at their best when negotiating financing, determining pricing, and testing business models.  Dealers can become obsessed with “current numbers” and miss the bigger picture of what is possible with the business.  Lack of view of the bigger picture can cause dealers to continue to “deal” long after the opportunity is gone.


Doers have a passion for what they like to work on. Often seen as artists, craftsmen, or inventors, they greatly enjoy the craft of their work and the end results of what they “do”.  This type of entrepreneur can fall into the trap of perfection, placing all the efforts into “doing” and even “re-doing” a process or product, delaying it from touching customer hands. This intense focus with “doing” in the business day by day often keeps them from working “on the business” or in making decisions for the longer term strategic outcomes of where the business is headed.

A Blend is Best

Whether entrepreneurs find other partners or senior leaders to balance their strength and create a balanced “soul” for the business is crucial to sustaining a business beyond start-up or a new strategy.

The first balanced entrepreneur I ever met was my father. Each year he prayed and hoped for a bumper crop, for the perfect show cattle. Despite dream-shattering hailstorms and winter losses of prime calves, he awoke each spring with a renewed hope. It’s probably why I still love springtime. His definition of success was not necessarily to get rich, but rather to provide the opportunity for family fun while fishing, for an education for his children, and for care for his aging parents.

By today’s standards, it is questionable whether or not he succeeded, but his sense of hope, hard work, and determination are his greatest legacy. Regardless of the cruel summer storms or winter freezes, there was always spring. Always a new day. Always a new possibility. This was the dreamer in him – the belief that you could impact the world around you and the tenacity to try to do so above all odds.

My father was also a dealer. He was a cattle buyer and trader. He bought and sold cattle and horses for himself as well as others. He earned his “dealer” status in a front row seat at the stockyard sales ring, where he had a reserved status on a cozy seat. His Stetson hat and his cigar were his calling card. His signals to the auctioneers were secret; they were even secret to me who often sat on his lap during major cattle buys. Only years later would I come to understand what a true dealer my father was. That was the day he walked into a reputable jeweler and attempted to negotiate the price of a “mother’s ring” for my mom’s birthday. As a young girl I was embarrassed. Today, having watched brilliant entrepreneur dealers over the years, I realize it was simply the way he saw business being done.  Everything was negotiable; you just needed to decide what you were willing to “pay”.

While he was all of these parts, he was also an accomplished doer. There were occasionally “hired men” to assist with the endless hours of work to be done, but his true expectation was that he and his family would and could “do” most of what needed to be done to run the operation successfully. My brothers were mechanical engineers who could fix, tinker, and weld sizeable machinery. They and our mother were veterinarians who could vaccinate, diagnose, and even assist in the birthing process of a cow or a horse. They were resource managers who had to determine the amount of feed to be leveled out for months of winter and keep water flowing in frozen springs. They had to “do” because that is what was done to keep the business of the farm and ranch afloat.

In the upcoming columns in The Partner Channel magazine, I will share the stories of dreamers, dealers, and doers I have met along the way. Other than my father, the other entrepreneurs will all have fictitious names. Nonetheless, their stories are real. Their successes and their struggles. Their wins and their losses. I have witnessed and at times contributed to them in some way – good or bad. It is with pride and great humility that I attempt to tell their stories.  My purpose is that learning from their successes as well as their failures, with the hope of a new spring, could improve the odds of success for anyone who has started a business, bought a business, worked for someone who owns a business, or has a family member who has done so.


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