Startup zen: Knowing when to pitch, when to punt and when to pray. 

Dedicated to John Startup of @Secret_Startup& his blog: “45 days to raise Series A” 

I read with tortured simpatico the blog of “John Startup” describing his 45 day sprint to a Series A (he is at Day 6 today). It is a poignant and agonizing window into the secret, tortured soul of any thinking startup CEO.

His journey resonates excruciatingly for me because we share many characteristics. We are both trying to launch not just a new “thing-y” but a new way of “doing”.

Like John, we have done umpteenth versions of investor decks, presentations and VC pitches. We have performed the passion play for investors so many times we have to guard against just “phoning it in.”

And like John, the “burn rate” meter incessantly rings in our ears, getting ever louder as the bank account dwindles.

But mostly, I share John’s “knot in the stomach” feeling that feeds our insecurities as we muddle through every day. This must be how a bug feels as it clings for dear life on a windshield barreling down the road at 75 MPH.

In this existential moment, though, we define ourselves as entrepreneurs and human beings.

Will we succumb to spewing an overabundance of BS to compensate for the gaps we sense investors think we have?

Will we maintain our grace with our colleagues as the pressure increases?

Will we continue to be transparent despite our desire to crawl up into a fetal ball and hide?

We agonize over whether we are doing enough, fast enough and in the right way. We try and pitch investors but the goal posts keeps moving. If we manage to get something built, then we are required to get users. But wait — if we do that — now we have to get customers.

And just when we think we have it together enough to approach investors — they move the post again and want to see how successful “it” is.

This is when we consider punting — generating revenue any way we can to live to fight another day.

But if pitching and punting are not working fast enough — what then?

In the exquisitely difficult startup journey, there are times when the only way forward is to surrender to the situation; harness every ounce of focus you can to maintain a vision of what you know is possible instead of being overwhelmed by the gaps you have right now. Prayer or meditation or whatever you want to call it — is the key. It can give us the heart space to find inspiration to continue to look for some angle or twist or maneuver that lets us carry on for another month or even just another day.

This is what Startup Zen is about — mastering the reality that the highs are exhilaratingly high and the lows are mind numbingly low. Grace lies in maintaining your balance in the maelstrom.

Judy Shapiro