What Makes Serial Entrepreneurs Tick?

Since debuting on this blog a number of entrepreneurs I coach have called to say how pleased they were to see me “doing something useful.” While I appreciated the thought, I ultimately focused on what a number of them suggested with regard to future blogs: “Why not just tell your readers what makes a serial entrepreneur tick and be done with it?” My initial response was, “Explain what makes these guys tick? I’d rather grapple with the Gordian knot or Proteus.”

But then I realized that a soup-to-nuts analysis of serial entrepreneurs wasn’t necessary in order to address my clients’ concern. I could discuss the defining attributes that make serial entrepreneurs tick, as I see them, on an “installment plan.” To this end, let me begin with a “definition” of serial entrepreneurs provided by a man who defines the breed: Sam “The Grave Digger” Zell. Zell offered his definition in response to a reporter’s question regarding why he crafted the incredibly intricate deal that enabled him to purchase the Tribune Co.:

"Because nobody has ever done it before. The true test of an entrepreneur is someone who spends his life constantly testing his limits. The definition of an idiot is someone who has reached his goals."

Apart from feeling that “idiot” is too harsh a term to describe a misguided or foolish business builder, I find Mr. Zell’s “definition” precisely on point. What he did not address, however, is why a serial entrepreneur is driven to chronically test his limits. To start addressing this issue –and the more general question of what makes serial entrepreneurs tick— I will look at Mr. Zell himself. Setting aside his incredible string of successes (that date back to 1969 or earlier), we see a man with an extraordinarily complex character: ● He is a fiercely private man – in an almost paranoiac way— as though he took Andy Grove’s advice regarding “how to survive” literally. ● He is crusty, often profane, and always combative. The nickname he gave himself –The Grave Digger— is thought by many to allude to something other than his penchant for buying distressed property and, after refurbishing it, selling it for a huge profit. Some say that the moniker refers to Mr. Zell’s eagerness to dig a grave for anyone with the temerity to oppose him. ● He expresses love passionately for the select few he feels deserve it. Any business professional Zell truly values receives a unique music box (re-designed annually) as Christmas gift. I once coached someone who received several of them. No “tombstone” award, or citation in that man’s office, instilled a greater sense of status in him than those music boxes. Yet the value of Zell’s music boxes pales in comparison to how he has kept the memory of his late partner, Robert Lurie, alive. Among other things, Zell created research institutes bearing his and Mr. Lurie’s names at The University of Michigan and The Wharton School.

Every time I read or hear about Mr. Zell I am reminded of a remark Freud made in his famous book, The Interpretation of Dreams: “An intimate friend and a hated enemy have always been indispensable to my emotional life…” Zell, it seems, has always had both. I often wonder to what degree this “orientation” to the world helps drive him to constantly testing his limits, while avoiding the delusion (that can come after attaining a goal), that it is possible to rest on one’s laurels and continue to derive psychic satisfaction. I’ll let you decide while I prepare to expand my analysis of what makes serial entrepreneurs tick for subsequent postings. All I ask, while you mull over if, or to what extent, Zell’s unique interpersonal attributes have caused his entrepreneurial passion, is to consider how many super-successful serial entrepreneurs share the attributes –paranoia, enemies, adored intimates— that seem to define Mr. Zell’s character. Three prototypic examples I know of are: Robert Edward “Ted“ Turner, III, Steven Jobs, and Lawrence J. Ellison. As you mull this issue over, be assured that I know that one swallow does not make a summer, and four serial entrepreneurs who share a unique mix of attributes do not make a psychological law. Or do they?

Note To Female Entrepreneurs: Most of the points I advance regarding the character structure of male entrepreneurs are irrelevant to you. In the norm, you are “built” differently and are driven by unique needs. I discussed this point in every entrepreneurship course I taught, and wrote about it in my last book, Reclaiming the Fire: How successful people overcome burnout. Yet I was never 100% positive that men and women develop an entrepreneurial spirit for non-overlapping reasons until I was captivated by how my daughter Katie developed businesses and business plans. In contradistinction to Sam Zell (and her daddy), Katie is never a curmudgeon, profane, or anything but wholly embracing of all people and most animals. I will discuss this “sex-difference” in detail in subsequent blogs.

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