How would you want to be eulogised?

A major challenge facing financial alchemists is to analyze the personality traits of successful entrepreneurs. If only we could assess in advance whether the person before us meets the criteria of "the successful entrepreneur," we would certainly invest some of our money in him, work with him or in some other way benefit from this knowledge.

In reality, the situation is far more complex. Entrepreneurs are made from different fabric and successful ones are not cut from the same cloth. However, a look at the profile of the successful entrepreneur shows, not surprisingly, that most share one trait that drives almost all of them. Entrepreneurs are not primarily motivated by the desire to get rich, as many believe.

Anyone who has spent enough time in the investment industry knows that entrepreneurs interested only in economic achievements should be avoided like the plague. In contrast, the desirable entrepreneur is motivated primarily by a sense of mission and strives with all his might to leave a mark on his financial endeavors - some sort of footprint in the sand.

Or to paraphrase the words of Napoleon, a political and military entrepreneur of the first order, "Fame is fleeting, but oblivion is forever." "Where would you like to be ten years from now?" This is one of the most commonly asked questions in interviews with entrepreneurs, and its main objective is to assess the candidate's level of ambitiousness as reflected in his personal and business vision.

A blunter, but particularly effective way of assessing this same characteristic is encompassed in the question "how would you want to be eulogized?" We hereby offer an alter-native version: "Imagine that in ten years this journal publishes a cover story about you. What would you like to see in the lead headline and in the sub-headline?"

There are generally two types of responses to this challenging question. One is along the lines of: "Mr. Israeli was very successful, but did not compromise on moral and ethical issues/did not lose his modesty/did not forget his friends from school" (erase whatever is extra), and so on. These are the entrepreneurs for whom prestige and honor are especially important, and success in their entrepreneurial activity is likely to establish a presence in their relevant group.

The other response is something such as: "Mr. Israeli did it his way, his original and unique way." These are the entrepreneurs seeking to leave a mark. Do not be misled. Both types of entrepreneurs can supply the goods. My personal preference is the second group, as they have greater efficiency. The entrepreneurial drive aimed at prestige and status is indeed a powerful one, but occasionally it is tainted with fuel that is not totally free of odor. And ego odor is one of the main obstacles confronting the business world.

On the other hand, whoever is driven by a burning desire to leave a mark, equips his engine with a compass that promises to navigate toward the goal in the most efficient way possible without any delays that can impair the process's efficiency. Another common question seeks to have the entrepreneur identify a role model in the business world.

There is a lot of information in the answer to this simple question, and I would include the question even if the interview were a short one. And indeed, who would you prefer, the entrepreneur choosing Donald Trump as a role model or the one who favored Warren Buffett? Someone who has spent time in the company of successful entrepreneurs knows they are not satisfied with themselves and, as a rule, are marked by the unease of those who must really prove themselves.

The successful entrepreneur is, how shall I put it delicately, a bit neurotic. An obsessive nature, the need to control and perfectionism are some of the qualities encountered in many successful entrepreneurs. These traits, it turns out, largely stem from a lack of security that has accompanied the entrepreneur like a shadow during his early years. The reasons are varied - rejection in childhood, emotional distance on the part of one or both parents, social isolation or another emotional offense. We are all that way more or less.

The entrepreneur is that way more. The successful entrepreneur is determined to undue his early wound using business success to provide relief - so he believes subconsciously - for his ailing soul.

Too great an emotional blow, needless to say, is likely to leave the entrepreneur helpless or unable to cope with the entrepreneurial burden, and instead of a necessary dose of neurosis, we face a poisonous brew of personality traits that will eventually impair the entrepreneurial effort. The other fuel that feeds the entrepreneurial drive and supplements the lack of confidence is optimism. Without it, the entrepreneur has no chance of recovery.

Optimism is seeing the world as a place filled with opportunities that the entrepreneur could one day use for his own needs. Optimism is what enables the entrepreneur to stride confidently ahead from one failure to the next without losing any of the sense of basic enthusiasm. It also enables the entrepreneur to err in making a risk assessment, when the correct assessment would have weakened him, occasionally even to the point where he drops out of the entire venture. But, as in the other fuel - insecurity - it is all a matter of dosage.

There is a delicate balance between the entrepreneur being sufficiently neurotic in order to be the motivator and level-headed enough to correctly assess the reality he encounters. Excessive optimism may affect the ability to assess reality and bring the entrepreneur to ignore warning lights. And in most financial debacles, warning lights flash before the crash. Luckily for those who interview entrepreneurs, optimism is a quality that is easy to identify and the entrepreneur's personal testimony on this matter is very reliable.

Two questions that are usually included in interviews with potential entrepreneurs trace significant events in the interviewee's past. Firstly, "What is the most painful fiasco in your career that you can recall?" is intended to assess the interviewee's subjective perception of failure, as well as his ability to cope with the event and perhaps even to become stronger while learning important lessons. The other question, aimed at that same target, is "What is the one decision in your professional career that, in hindsight, you would have wanted to change had you been able to?"

Surprisingly, the optimistic entrepreneur does not grimace upon hearing any of these questions. As far as he is concerned, the sequence of events in his life serves as a continuing process of personal and professional development. In this process, there are no exceptions for a given event or decision. They all serve the road map to the much sought after end - leaving a personal imprint. And money, how is it related to the matter?

Well, to the entrepreneur money is like an accessory, and its importance lies in the fact that it is the only means that can serve as an objective measure of success or of a measure of the depth of the imprint left behind.

This article appeared in the Israel Venture Capital & Private Equity Journal. IVC Research Center publishes the Israel Venture Capital & Private Equity Journal (IVCJ), a quarterly review of trends and developments in the Israeli-related venture capital industry. IVCJ, distributed worldwide, is dedicated to provide wide-range coverage of Israel's venture capital industry. For more information please visit http://www.ivc-online.com

The article was reprinted in the Israel Venture Capital & Private Equity Journal with permission of The Marker, where it originally appeared in Hebrew.