The cynical entrepreneur

Cynicism is a two-edged sword. On the one hand cynicism can lead to a debilitating fear of taking strategic risks. Such fear does not bode well for life in general, much less building something.

On the other hand, cynicism often comes from experience & is often seen as the opposite of naivety. One who’s naive may well jump in to entrepreneurship head first, but the odds of them ending up breaking their own necks is also nearly certain.

So how does one balance this out? Is there even any one balanced solution? What if I said that no one individual has to find this balance on their own to be successful?

Like most things, the devil is in the details. While most functioning humans find balances in these areas occasionally, in business it’s critical to recognize that businesses are usually more complex than any one person & as such requires a balanced team. While your marketing guy will undoubtedly need to be an unabashed optimist, you certainly want your technical guy to be an unapologetic realist. Surrounding oneself with clones of oneself is a sure bet that one will fail to produce anything of significant scale. Even Steve Jobs needed to be brought back to earth on occasion. He was known for his “binary” evaluation of team members, they were either: “insanely great” or “crappy.” Nothing in between. That being said, Apple would never have produced anything worth owning had his definition of “insanely great” been reserved for his own doppelgangers. Nope, his dichotomy extended to his prerequisites for these judgments, most simply described here:

This means Steve Jobs may have been responsible for inventing the staffing equivalent of the Agile Method, leading Steve Wozniak to point out that: “Some of my very best friends in Apple, the most creative people in Apple who worked on the Macintosh, almost all of them said they would never, ever work for Steve Jobs again.” However, there was a method to that madness that should be understandable to any high performer on the planet, Woz adds:

“He would directly confront people and almost call them idiots,” explained Wozniak. “But you know what? When they confronted him back and told him why they were right in understandable forms, he was just testing and learning, and he would respect those people and give them high privileges in the company.”

What’s going on here? Is he a know-it-all egotist or not? Not at all, he’s cynical enough to know that he can’t be surrounded with false-confidence… he needed people whose abilities are commensurate with their rhetoric.

Think that through, “high privileges” going to the ones that don’t kiss up? Think that through again, because it’s profound. Could it be that the secret to his success wasn’t his tech chops, or even some “prophetic” foresight, but instead the lack of naivety (read cynicism) to recognize that when the rubber met the road he needed to be surrounded by confidence, not con men?

Jobs is a relatively extreme example, success can be found without producing a multi-billion dollar company. The balance doesn’t need to exist in one person either, but that leader who’s looking to maximize the potential? Well, unless they are chasing around sweetheart government subsidies, they will need to make their first priority assembling a team that gets things done, not one that blows sunshine where the sun don’t shine. That requires some well placed cynicism, especially concerning your own omniscience (or more likely lack thereof). As the good book says: if you judge yourself you wouldn’t need to be judged!

Any business plan that includes actual results as a deliverable will require accountability and that accountability will only exist with a wise (cynical) leader at the helm. Yet if that leader is fearful (cynical), they will avoid accountability and ultimately fail. So cynicism in-and-of itself is neutral, it’s how it’s used that defines it.