When most of us dream of making it big as an entrepreneur, we imagine all the pleasures our success would afford us. But many in Silicon Valley who have managed to build billion dollar companies, rather than make themselves comfortable, opt to regularly torture themselves instead. 

Take Twitter and Square founder Jack Dorsey's recent Twitter comments about his unusual eating habits as one example.

Dorsey isn't the only founder with profoundly uncomfortable habits.

Not eating for three days? That sounds, in a word, miserable. And Dorsey isn't the only famous founder who likes to make themselves profoundly uncomfortable. Digg founder Kevin Rose walks around in the snow in flip flops. Tony Robbins favors morning ice plunges.

"A surprising number of YC's best founders are also into some sort of extreme physical something," Y Combinator chairman Sam Altman has observed.

Outdoor Magazine has also noted the over representation of rich people in endurance sports of all kinds. That's partially down to the fact that training for triathlons requires money and time that the less well off might not have, but it's also often about character and the pursuit of meaning, according to the magazine.

"By flooding the consciousness with gnawing unpleasantness, pain provides a temporary relief from the burdens of self-awareness," researchers who investigated the phenomenon are quoted as saying. "Pain helps consumers create the story of a fulfilled life."

Or maybe it's just an eating disorder?

So is that what's going on here -- are ultramarathons, an affinity for ice water, or a failure to eat just an extension of extreme personalities looking to prove how far they can push themselves? Twitter isn't so sure. Here's one representative response to Dorsey's musings from author Roxanne Gay:

She wasn't the only one calling out Dorsey for publicly normalizing behavior that looks a heck of a lot like anorexia. Others wondered how the world would react if a successful woman announced she fails to eat for days at a time.

There is some scientific evidence that fasting can prolong life, though the matter is far from settled. But the annoyed response to Dorsey's comments suggests one possible explanation for his behavior isn't "biohacking" but something more akin to mental illness. Though the question of where to draw the line between extreme personalities and outright unhealthy ones is always tricky. Is Elon Musk crazy? Probably a little, but that's what makes him Musk, right?

Or perhaps it's stoicism?

There's one more possible explanation for the extreme behavior of a strikingly high percentage of successful founders, which comes from the New York Times' Nellie Bowles. Many of these fans of extreme self-deprivation, she points out, are equally enthusiastic followers of the ancient philosophical school of stoicism (though not Dorsey, at least not publicly), which "argued that the only real treasures in life were inner virtues, like self-mastery and courage."

If you're rich and bored and have it all, the only thing left to strive for may be the discipline to not eat or walk barefoot in the snow.

But from Roman times on up to today stoicism has also always been a favorite philosophy of the elite. At least in part that may be because of its relentlessly inward focus. It calls on the individual to shape him or herself to be better, not to shape the world to be better.

"Stoics believed that everything in the universe is already perfect and that things that seem bad or unjust are secretly good underneath. The philosophy is handy if you already believe that the rich are meant to be rich and the poor meant to be poor," Bowles writes.

So in the end, is extreme behavior like Dorsey's an extension of an extreme (even possibly ill) personality, a quest for meaning in a life of material plenty, or a way to avoid looking at one's responsibilities in regards to the larger world? The exact answer probably varies by the individual (and maybe even by the day), but there' no denying that many of Silicon Valley's most successful sure do like to torture themselves.

What's your take on Dorsey's fasting: extreme but understandable biohack or simply unhealthy?

Published on: Apr 10, 2019
The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.