That Founder Feeling

Lots of ink gets spilled on the mechanics of starting a business (I guess readers and search engines both love “how to” content), but I haven’t come across many accounts of the emotional experience of starting up that feel true or accurate to me. (Marc Andreesen has one of the better posts on the subject, but he only deals it a glancing blow on his way to a different point altogether). From my experience, the emotional side of creating a new company is at least as challenging and complex as the tactics of building a business, and worth a closer look.

My experience of starting companies is pretty limited: I was an “honorary” co-founder of my first startup, Adjacency, because I gave them their first e-commerce job (building Patagonia’s inaugural online store) before joining them as a partner. After selling Adjacency to Sapient, I co-founded Judy’s Book with my business partner, Andy Sack. I’ve been working closely with my friend Sree on his company, IndieMarketer, from concept through its many phases of development (and now, hopefully, to Product/Market Fit). And I recently co-founded (again, with Andy and a great operating team) Cooler Planet, a company that connects residential solar customers with local installers.

All of these businesses were built in the same basic domain: Web-based software and services. But the example that really helped me see the underlying emotional patterns in the founder experience came from a completely different sphere. Earlier this year my brother relinquished his partnership in a big New York law firm to start a boutique firm specializing in online commerce and digital intellectual property. Despite operating in a completely different business universe, his emotional experience as a co-founder of his firm, DeVore & DeMarco, would be immediately familiar to any of the technology founders I’ve worked with.

This was surprising to me, mostly because I think of lawyering as one of the less entrepreneurial vocations out there. (For clarity, I don’t consider ambulance-chasing and other forms of low-grade litigious opportunism as lawyering, entrepreneurial though they may be). In my experience, law firms resemble universities more than businesses, hoary with tradition, bound by the rituals of the court and steeped in a culture of seniority. And lawyers, by temperament, are cautious and methodical people, much more inclined to avoid or mitigate risk than they are to seek it.

But after following the white shoe legal trajectory for over a dozen years (law review, clerkship, federal prosecutor, senior associate, partner) my brother arrived at the emotional certainty that ultimately animates any founder: “no matter how hard it proves to be, I would rather write my own story than follow someone else’s script for my life.” When it arrives, this certainty goes off like an emotional bomb, triggering a nausea-inducing cocktail of elation, fear and anxiety. It also unlocks previously unknown reserves of energy, a “fight or flight” response that fuels the creative effort of shaping and implementing a new business.

There’s much more to be said about the many emotional phases (high and low) that follow this initial explosion, but to me it represents the point of no return that any entrepreneur has to reach before setting out, a “burn the ships” moment that makes it impossible to imagine doing anything else. The fact that my brother and I now share this experience has added a layer of understanding and mutual support to our relationship; this fellow-feeling among founders is another theme that I want to explore in a future post.