The Philosophical Entrepreneur

Today’s article in Entrepreneur on philosophy and entrepreneurialism got my attention. You see, I was a Classics major at UC Berkeley (my senior thesis was on Plato’s Lesser Hippias and its discussion of Homer’s Iliad and Odyssey).

What does this have to do with being an entrepreneur? Don’t yawn yet. People have often asked me the value of that liberal Western philosophy education and my career as an entrepreneur – and it’s huge.

After all, I launched my first software company while a student at Berkeley, so why didn’t I just join the College of Computer Science? The main reason was that I was already earning a princely living as a programmer/tech entrepreneur, so I thought, why bother? The other reason was that as a result of earning that nice living, my grades – full disclosure here! – didn’t quite get me to the requisite 3.9 GPA to make the CS cut.

The author of the article, Nicholas Miller, cites five great reasons why a strong base of philosophy helps entrepreneurs succeed. I’d like to add five more which have been keys to my successes – and strengths in my failures.

1.      Strong Intentions, Lightly Held

This is #1 on my list for a reason. How can we have strong intentions – a startup business and the desire to make zillions of dollars – and not be crushed by the small and large disappointments that buffet us every day? When our startup fails, how do we pick ourselves up and continue? For me, having strong intentions lightly held is the key because things simply don’t work the way we want them to. We don’t control everything, dammit. So holding your intentions lightly, allowing them to bend and adapt with reality, with what is, with the changing currents of your startup’s river is crucial to remaining centered and equanimous – i.e., key to remaining strong and resilient.

2.      Resilience

And if there’s anything an entrepreneur ever needed, it’s resilience. Your ability to realize that attachment is pain (Buddhism) is your path to equanimity – “mental calmness, composure, and evenness of temper, especially in a difficult situation.” And every entrepreneur faces difficult situations just about every day – fundraising, payroll, sales, hiring, firing – the list is seemingly endless.

3.      Pragmatic Optimism

Look, it’d be pretty tough launching a new company if you’re not optimistic about the outcome and having strong intentions (lightly held!) to make it happen. Otherwise, you wouldn’t do it. But a strong sense of pragmatism must prevail to look at what is with a level of objectivity and detachment. A solid base of philosophical learning helps develop that.

4.      Unstructured Thinking

In my experience, my philosophy education has certainly played a strong part in me being an unorthodox thinker. Assimilating different traditions, seeing things from multiple perspectives, viewing problems from a high level of abstraction, appreciating divergent thinking from others – all these are the fuel to seeing opportunity through inspired creativity.

5.      Inspiration

Which brings us to inspiration, perhaps one thing that we entrepreneurs truly must have in common. Plato famously said (through Socrates in the Apology) that the unexamined life is not worth living.

So with posthumous apologies to Plato, Kuhn’s corollary is that the unexamined startup is not worth starting. Finding the right startup business and model requires deep reflection and true inspiration. I have found deep inspiration from having studied Buddha, Kant, Descartes, Heidigger, Hume, and others at Cal. And that’s why I believe that a base of philosophy is so important for a successful entrepreneur. I love seeing that foundation on someone’s CV – it’s a predictor of a broad, expansive mind.

I'd love to hear who or what is your source of inspiration as an entrepreneur. Please share your thoughts.