What’s In An Entrepreneur’s Weaknesses?

Two things. Reality and perception.

Every single person has strengths and weaknesses. Those who excel are stronger than others in at least one performance aspect, and those we take as mentors or leaders generally outperform everyone else on many counts. Appearances will only take you so far, it is ability and skill on which you go the distance and, especially, stay there. For most of my life, until recently, I believed that perception and spin were nothing but an extra edge, and did not give handicaps or weaknesses much thought until recently.

Being highly competitive, I always play to win, and playing every card I’m dealt to its highest advantage is a given to me. Weaknesses must be fully assessed and covered, and strengths properly exploited. The winning hand is as much about how you play the cards as about which ones you are dealt, and a slew of high cards or trump make a single weak card of little consequence. End of analogy: the little guy playing against the house or a stacked deck isn’t relevant here.

The most successful of us are, among other things, the best at:

  1. Identifying our weaker areas
  2. Understanding exactly what dangers result and how to avoid them
  3. Compensating through alliances with others whose skills and talents are complementary
  4. Concealing our weaknesses
  5. Leading with our strengths

Having had the privilege of working with and knowing many self made men, I can say that every one that I observed applied these 5 criteria. These people divide roughly into 3 categories, those who made it and never fell, those who fell from a lofty height and climbed back up, and those who fell and never managed the full climb again. The difference in perception of weakness among the 3 groups at any given stage is dramatic. The reality is that #4 in the list above can, all by itself, create failure. This plays out in a way that is utterly primal. Still, a seriously wounded animal can not only still win a fight, but can become supernaturally stronger and more ferocious. Some of that is pure adrenaline, a body’s natural narcotic as well as fuel, but the greater part of it is simply how much the fight matters, or what the stakes are.

Humans, though, are a lot more complex than animals. Common wisdom tells us that the player who has least to lose has an advantage because of being willing to risk more. That easily explains why there are many 20 year old entrepreneurs (who do not yet have spouses, children, and mortgages) for every 40 year old one. It doesn’t explain, though, how to get in the ring, keep getting back in after losing, and stay there. More importantly, it doesn’t explain who the prize fighters are, or how to recognize whether you, or others, are one.

Here’s an example where handicaps, including age, didn’t matter:
“I was 52 years old. I had diabetes and incipient arthritis. I had lost my gall bladder and most of my thyroid gland in earlier campaigns, but I was convinced that the best was ahead of me.” Ray Kroc, on the founding of McDonalds Corporation

This was an entrepreneur who understood perception and spin to the max. He was a consummate salesman whose greatest sale, it’s been said, was the purchase of the original restaurants. I did not meet this man personally, but would make a bet that one of his self acknowledged weaknesses was a penchant for risk. Was he, perhaps, over compensating in the rigid, old fashioned management style he employed in building his final empire, and if so, did that over compensation turn into a bastion of strength?

Leaders, whether successful entrepreneurs, businessmen, or politicians, boast among their number a disproportionate percentage of manic depressives (now called bi-polar disorder) and borderline (BPD) personalities. Although the personal styles they present to the world can vary widely, can as easily present as brute strength and charisma or as suave and sophisticated, they are all, underneath, powerful alpha creatures. Most learn quickly that much can be achieved via perception and psychology, once primacy has been established. There are also plenty of normal guys who originally entered the fray with plenty of ability and ambition. A majority of them elect to semi-retire by or before middle age, and most, given a trust level, will confide the event that made them withdraw from the ring. The sentence I’ve heard most frequently in describing the turning point was, “I realized I didn’t have the stomach for it.”. At a higher trust level, and providing you know all the players, you might hear a specific story of betrayal.

The alpha fighters I am describing, often have what should be really serious weaknesses.

Weaknesses that have to do with literacy, or numbers, or money management. I’ve frequently marveled at the fact that there are invariably at least several, and sometimes a lot more, people around such an individual, who contribute to covering and compensating. This would argue that the serious weaknesses should become widely known, yet they do not. I hardly think that all enablers in such relationships are simply co-dependent and dysfunctional. What does become clear with experience and observation, is that the ability, scope, and skills of these individuals are such that even serious weaknesses are outweighed.

In the case of those who succeed, sustain no serious falls, and go the distance, the compensation mechanisms become as smooth and finely tuned over the decades as a hand built exotic car. The presentation dazzles, the engine purrs, and all is right with the world. Steve Wynn had already lost most of his vision when he lost the Mirage and started on the Bellagio, long before the recent painting accident. Many people, likely in the thousands, had knowledge of this, yet would tell you how incredibly smart the man is without a thought of mentioning the loss of vision.

Those who are truly determined and have outstanding ability are usually spurred to greater determination and performance by handicaps. This can sound perverse to some, but it really isn’t at all. If you have the personal power and drive and ability to achieve, the fire and passion to grab life by the short hairs and give it your all, then the never-ending contest itself, with both its losses and gains, is your motivation.

There is plenty of writing and advice on business and entrepreneurial success. If you aren’t out getting an MBA first (no determinant of success in itself), study and familiarize yourself with the materials relevant to your business activity anyway. How much you learn through studying, and how much through firsthand experience, though, is not the deciding factor in whether you want to and can, get and stay in the ring. This type of reading, a blog called Leaders on Leadership, is just as important to understanding the challenges and how to use your own abilities in terms of combining reality and perception.

We live to develop and exercise our talents and abilities to their fullest, and strive for happiness and success (in or out of the ring). Knowing our weaknesses and addressing them fully is the one critical factor far less spoken of or written about. Perception of strength or weakness is equally critical.

One of the most powerful individuals I met over the years, Edward J. DeBartolo Sr. (you used the full moniker until granted the right to address him by his given name), was a fairly small man physically. Few people, however, could stare back into those piercing eagle eyes for long, or stand up to the iron will. Even at the age of 90, this man still answered his business phone beginning at approximately 5 am, every single day.

If the fierce intensity of such a gaze is revealed to and turned on you, there’s only one involuntary response that signals your place in the ring. That response is a thrill of excitement and anticipation in the knowledge that you also will do whatever it takes to achieve your goals and stay there.

Those closest to you will know who you really are, but in business you deal with hundreds and sometimes thousands of individuals who will stubbornly see you as the first impressions you offer them. Making good ones may not matter substantially if you’re in the position to continue and perform brilliantly, but occasionally it will matter, and the rest of the time it’s like a free opportunity to put some extra money in the bank. It is also a gesture of respect, and that is always a good way to begin.

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