Bad Asses Make Peace with Unanswered Questions

Posted on February 7, 2013. Filed under: startups, venture capital |

As I walked to work this morning, I found myself extremely aware of how wound up I am in moving forward on our new mobile web endeavor. I found myself hurrying. Hurrying to shorten my morning routine at home, hurrying to make progress on product design and definition…hurrying to get administrative tasks done…and if I had to take a step back and examine the hurry more holistically…it’s really a hurry to answer all the unanswered questions between today and the future I want to build into the world. At Hyperpublic I lived hurrying for two years…a founder is never satisfied as long as questions are outstanding…but the question I arrived at today, which I already knew the answer to, I just hadn’t articulated it in my mind, is as follows: “Is hurrying a necessary state of mind for a startup to succeed?”

There is no doubt, when a tone of hurry is introduced into a founder’s mind, and by extension a team’s mind and culture, things get done. We see founders all the time setting artificial deadlines, things to run at…as though creating a sense of urgency is a necessary catalyst to stretch a team to produce. Urgency is real, and sometimes a deadline is the difference between getting a deal and not. Sometimes, when building a startup, you have to be in a hurry or someone else comes along and eats your lunch. But there is a difference between recognizing moments when we are in a hurry, and creating a culture where the only way to find the finish line is to live and work in a state of perpetual hurry. It doesn’t take a rocket scientist to know that running a marathon is not simply a consecutive set of strung together sprints…but there is more to this question than just strategic pacing.

Hurrying can be at odds with thoughtfulness, happiness, health, etc…I have seen some repeat-founders, in recognition of this truth, slow down too much. Having isolated the truth, that hurrying is not the way to win a marathon, they attempt to create a new culture and personal lifestyle that takes urgency out of a startup’s culture…often these repeat founders have had a success in the past, and now in their wisdom, they say “this time, it’s important to be as zen as I was in that lovely 12 month break between gigs, so this is what our new culture looks like.” Almost invariably, those founders either fail in the new endeavor or realize they swung the pendulum too far, that they lost a full cycle of development and progress, and now it’s time to “get serious and buckle down”…at which point they inject hurry into a culture that isn’t as ready to accept it.

On the other end of the spectrum, I have seen young first time founders hurry the entire way through and either succeed wildly or burn out while running at the finish line. I think you get to do this once, and only once, in your life. I have never seen a repeat founder attempt to sprint wire-to-wire the second or third time around.

So where does that leave me? Sort of retraining myself…My mind and my body recognize this period of deep uncertainty/opportunity as a state where we hurry to answer the unanswered…we’ve been here before…and when we hurried we did well…so I wake up and instinctually I am hurrying…taking deep hacks at the unknown…but as I walk through my day…my experience and rational is talking to my mind and body and saying, “dude, chill the fuck out. You are not in a hurry right this second. You are not going to lose this market if you enter a week later. In fact, you don’t even know yet if your timing is 6 months early or 6 months later than optimal. You haven’t raised capital and you don’t have any burn…time is not running out, it is just beginning. THESE UNANSWERED QUESTIONS THAT YOU ARE ATTACKING LIKE CANCER WILL GET ANSWERED OVER THE NEXT 5-10 YEARS. STOP TRYING TO ANSWER THEM ALL TODAY.

So the CAPITAL LETTERS in my head are my experience yelling at my founding instincts…saying “you asked to be in this ocean of unknowns…I told you how nice it was to chill on the beach and let the world pat you on the back…and you just couldn’t let us graduate into the life of a non-hurried venture capitalist…waiting for other people to answer the unanswered for you…FINE…we’re back…answering the future ourselves…and making up the answers where no answers exist…I accept this, but remember you are a mother fucking bad ass, don’t act like a fucking kid.”