Aristotle believed that virtues were not necessarily a good thing: the key was to stay balanced between corresponding pairs of virtues and vices.
For example, what would you say about the "goodness" of courage? Courage is a classic virtue, one Aristotle would have certainly recognized, and, nowadays, most people would probably consider virtues "good" and vices "bad." You'd probably therefore say that courage is a good thing--right?
Aristotle would disagree with your unqualified categorization. If you asked him why, then he'd probably tell you about a brave foot soldier standing across the battlefield from the enemy's entire army. If that foot soldier charged the enemy by himself, wielding only his shield and spear, then his courage would be undeniable. Few men would have done such a thing. Few mean would have been so brave.
But the problem, of course, is that the lone foot soldier who charges the enemy's entire army is also incredibly stupid. He's brash, not brave.
Aristotle's "virtue theory" of balance and temperance went on to influence some of Western Civilization's most venerated leaders. Example, pictured above: Marcus Aurelius describes it in book 6 of his Meditations.
Now, we could stipulate some circumstances to create a situation in which either, the soldier had no other practical choice--say, if his entire force had already been defeated and his options were to either die fighting or be captured--or his brave sacrifice accomplished some greater good, perhaps for his fellow soldiers who are able to safely flee the enemy because of the brave soldier's distraction.
Let's not do that, though. Let's instead keep this simple. The soldier did have other practical options, but he chose to do the "courageous" thing. The result would almost certainly be that he would have died for no good reason, and that's why Aristotle held that the "right thing to do" in any given case was to strike a balance between virtues like courage and vices like cowardice.
The right thing to do, in all things, for Aristotle, was to find and stay at equilibrium.
(To dig deeper into Aristotle's "virtue theory," Thomas DeMichele does a good job breaking it down further in Vices and Virtues Explained.)
Now, I won't presume to make a blanket statement about all possibilities for all entrepreneurs who ever have been or will be. But for me, I've never been able to start a company at equilibrium.
Part of the reason for this, I've observed, is that I've only ever been interested in starting businesses based on (what Peter Thiel calls) contrarian ideas. (For example, Hubscriber.)
"Most people believe in x, but the truth is the opposite of x."
—Peter Thiel, Zero to One, page 6
Although I've not confirmed this yet firsthand, on one hand, I'm told that this is "where the money is" for entrepreneurs, meaning, more specifically, that the biggest financial rewards tend to only follow the biggest bets. When you believe something that most others don't, and you commit to build a business around it, that's like the performance-art equivalent of a really big bet. Your wager is your livelihood, and for as long as the dice are in the air, no one--including yourself--knows whether you're ever going to be able to climb back out of that hole you've chosen to dig under your feet.
It's hard to strike oil with a shovel, which is why it rarely happens. But that's a pretty decent metaphor for bootstrapping a contrarian business. You're either brave and dumb, or just brave enough to venture out in the direction in which you were also smart enough to know the pot of gold lay.
I can also tell you from personal experience that raising some seed capital doesn't change this much. Sure, it might mean that you can trade in your shovel for a backhoe. But you still have to be crazy enough to dig where no one else is digging, and, chances are, you'll pick the wrong spot. That's why I now have a personal bent against raising capital to work on untested, contrarian ideas. Committing to your contrarian business idea is one thing when the stakes are only your livelihood, present, and future. But committing to your untested, contrarian business idea can also be one of the best ways to wipe out about $500,000 or so of startup capital. I'm sure people feel differently about the idea of gambling with someone else's money. But for me personally, I don't like losing anyone's money but my own ;)
OK...so, is there a way to square Aristotle's view of the "right thing to do" with making a commitment to build a contrarian business, even when the danger is high and the balance (against prudence) yet unproven? I think so.
Well, really, I hope so, and here is the justification I apply to my own "foolish" business ideas. It comes from Seth Godin's Purple Cow, page 34, (pictured above). I imagine the future and look around to see what other people think about what I've built. If I can imagine a future in which people celebrate it, then I use that as a proxy for my not-yet-confirmed genius, for looking where no one else is.
Therein lies the paradox. The aura of a contrarian is one of "I don't care what other people think; here's what I know to be true." Yet what other people think, and what other people do, particularly with their time and money, is essential for one day proving yourself to have been this genius, contrarian entrepreneur all along.
The trick is to think for yourself when deciding where to dig and to rely on others to tell you whether what you've dug up is valuable.
That, dear reader, is easier blogged about than done.