We have lionized Steve Jobs, and the set of characteristics that he brought to bear over his extraordinary tenure at Apple. I might go so far as to say we have internalized them as the archetype of success for a founder.

Fittingly, one description of him, coined by his colleague Bud Tribble in 1981, is his ability to create a “reality distortion field”. Described simply, it’s the way that really dynamic individuals can make listeners believe in things that otherwise should not be possible, or that tickle the edges of reason, by virtue of their storytelling ability. I have looked for that trait in founders, though describing it in somewhat different terms:

The best founders bend time.

Some fit 25 hours into a day.

Others live in the future, but can invite in you for a peek.

— Kanyi Maqubela (@km)

August 26, 2015

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In either circumstance, but particularly in the latter, it is not the laws of physics that are bending, so much as the truth. And often those founders who can tell a superior story about the future; who can make the impossible sale, or convince the out-of-reach hire, measure truth in a different way than the average person. After all, a dataset can be interpreted in infinite creative ways.

And as I’ve reflected further on this, and discussed it among mentors, I’ve noticed the same thing, over and over again: the ability to use this superpower, which is certainly what it is, invariably cuts both towards the good and the bad, and in non-trivial amounts. To put it more specifically, creative interpretations of data allow for logic-defying moves, but they also result in logic-defying vulnerabilities, mistakes, and oddities. Strangely enough, however, in my conversations nobody has been surprised by this, and they take it as old hat. Moreover, many investors who specifically look for this trait in an individual founder have acknowledged that it comes with a big old bag of complicated. And others, to that point, have decided they would rather not engage with those types of founders, and believe they can drive returns and create huge success while avoiding them. And yet, it is well-understood – conventional wisdom, even – that many of the best entrepreneurs and most innovative companies of all time, were manifest in precisely this way.

So what’s the deal? As always, comments welcome and appreciated.