Wisdom and entrepreneurship. What does it all mean?

I watched an episode of Supernatural this morning as a kickstart to the day. I know…it’s not a great show, but my mom got me addicted early. Remember the old WB? Buffy, Supernatural, Felicity, Sabrina the Teenage Witch, Charmed, Smallville, Roswell. It was this amazing moment in high school when all these shows were on that tackled fantasy as a genre that had serious insights into the mind of a teenager. Of course, none of them were as good as Buffy, but here I am twenty-eight and a still nostalgic for the good old WB, still watching one show from that bygone era, Supernatural…which endures…occasionally in a tiresome way.

How is this related to entrepreneurship? Well…it really isn’t especially since Sam and Dean Winchester don’t get paid for their bloody efforts. But, take the most recent episode of Supernatural which sees Dean take Death’s ring for a day as a bet. If he can wear the ring and take Death’s duties for a day, he can get Sam’s soul back. (Yeah yeah yeah…I know…ridiculous stuff. I know!!)

Anyway, this does not go off without a hitch. Dean takes some lives and every time he does, the newly dead person asks ‘What does it all mean’…to which Dean optimistically replies “It’s all just dust in the wind’.

He quickly loses the pithy answer.

Tonight Jeff Revesz (@infogasm) and I spoke on a panel at Wisdom 2.0 NYC, a first-run conference (sister to the larger one on the West Coast) bringing the ‘wisdom’ community (yogis, meditation experts, activists who have actually been catalysts for social change efforts in their lifetimes) and the technology community (startup founders, hackers, social media people).

The panel was kind of amazing. Full of people with serious social change cred. I felt a bit intimidated to be honest.

A couple of the questions got me thinking. the first, ‘What is the role of audience in tech development’ and another “Is it better to focus on building your product to a point where you’re completely happy and then releasing it, or is it better to focus on building it to a point where you can release it and get feedback?”

What is the role of audience, really? Well…when we were running ASI we had a smallish audience. We were B2B, so the role of audience was ‘audience as market’…it would either squash us or reward us for our work. It was like having to please a capricious god..a media god that only bought software in Autumn and left you to starve during the summer.

I tell you…meditative it was not. But it did teach me something. Wisdom? Maybe…

It gave me insight into this thing called market…into the buying cycles of a certain segment of the market. It gave me insight into the needs and desires of a whole industry and the necessity of quick and targeted response. It forced us to pivot— to change and enhance our product offerings.

This were not things I knew when we started the company. No…not at all. Jeff and I…we were driven by ego. We wanted to be on the front page of Techcrunch. We wanted to be in Wired. The How’s and the Why’s unfolded over time.

What is the role of audience? Well, audience is market. It’s individuals acting as a crowd. In B2B the audience is a bit obscured, less immediate. Both are unforgiving.

Now, at The Huffington Post I am a Product Manager. I work with my developers on between 10-20 or so projects at any given time. It’s interesting to break these projects down into groups. One group consists of totally new products. Another consists of fixes and improvements to existing products.

The new products either come from the brains of our edit and tech teams, or from suggestions made by our community. The fixes and improvements usually come from our community. Sometimes suggestions are given to us directly. Other times we track usage data and end up tweaking the product to improve our numbers. Occasionally we have actual bugs that require fixing.

In all cases, we have to listen carefully to our community to know when to build something new, when to pivot an existing product, and when to fix something that’s broken. It’s a really interesting exercise in humility and reflection from the moment you conceive of a new app to the moment it is released and finally bug-free.

In a conference full of meditation experts and wisdom seekers, I realized that Entrepreneurship, and even the more cushioned version (Product Development) is a path to both.

To have your livelihood depend upon the reception of your idea by the market and/or the mob…is to be completely humbled. There were times when I had to choose between paying rent or paying for servers and getting us to a conference where potential clients would be. Playing it that close to the bone means feeling the needs of your customers at a very acute level.

Beyond that, starting a company is an act of faith. It’s a thought experiment. And it leads to a lot of other experiments. It erodes the ego even as it makes you aware of others in the form of the market. It makes you want to optimize yourself to the task of building the company, of devotion to the idea. For me, that meant a series of experiments with diet and exercise regimens on top of the grueling work of running the company. At one point, in the zeal to optimize myself to the task, it meant cutting out caffeine, sugar, and most salt from my diet and running 5 miles a day. The startup made me a fanatic for a time. A zealot.

Now, I am striving for balance. A thing not easily achieved when actively involved in a startup. I know few ego-less founders. Few founders who sleep or eat healthily or don’t drink and eat to excess to manage the stress. When we’re not bragging, we’re in despair. When we’re not in despair, we’re bragging.

We can be pretty insufferable as many of my non-startup founder friends found out.

So what wisdom in the end can be gained from that life? What does it all mean?

I want to say that you become ego-less for a time…after all the bragging and all the despair. That there are moments when you really ‘see’ into the scrying bowl of the market and ‘know’ what it wants like a bolt of lightning. That after a while, as with any creative act, you begin to feel like something is driving you…something outside of yourself. That a path opens up for you which offers far more freedom and self-acceptance than any other professional path other than the full-time pursuit of art/writing/music.

I also want to say that simple life-affirmative acts emerge as important and devotional. Eating dinner with a loved one. Writing a letter to a friend. Walking in Central Park. Simply because you have very little time and less energy to allot to anything unimportant.

And finally, that you begin to see people differently. The breakdancing group on the R train stops being annoying because you realize they are entrepreneurs like you. The summer crowd outside of the Broadway and Prince St. Station stops pissing you off because it’s partially caused by Latinas selling hand-cut mangos and they too are entrepreneurs…so fuck yeah! Good for them!

What does it all mean? Well, seeing the world through entrepreneur-colored glasses really changes things. I have to say that it…i.e. life…really has little meaning if you are not doing what you love and doing it to your best ability.

I think that means I belong in startups and specifically on the product development side of things because that’s when I really start thinking outside of myself. That’s when I start to have a glimmer of that thing we call ‘wisdom’.