Jordan Cooper's Blog: startups, venture capital, etc…

What’s Next?

Posted on August 29, 2012. Filed under: Uncategorized |

I was walking on the beach today, as I have done almost every day for the last week and a half, and as usual, over the sounds of crashing waves, the mind wanders to one of 3 or 4 topics that are not fully resolved in my mind.  Today and in general I have been grappling with the question of “what’s next?”  There have only been a few times in my life where I have stared at a blank slate and agonized over what to draw.  When I left General Catalyst to start my first company the slate was not blank.  Even before I knew what I would build, I knew the next step was to build something, and that was direction enough. I had such a chip on my shoulder after GC decided not to blank check invest in me as a founder that I had rocket fuel in the tank driving me toward entrepreneurship right out of the gate.  That endeavor was less about what I was going to build and more about becoming an entrepreneur…one of the many lessons I learned from that failed experience was that all the will in the world to start something is not enough to succeed at building something.

Fast forward about a year and half, I had just shutdown my first company, lost 50% of my investors’ money, returned the other half…and again…I faced a blank slate.  This time I wasn’t so sure I would build again.  Maybe I was supposed to be an investor? Maybe I was better at that? Maybe I was supposed to build again…but what?  Would I be able to raise capital again even though I lost money for investors? Was I emotionally ready to jump back in or did I want the safety of sitting behind some Sandhill desk, working hard, but working for someone else…not putting my identity and name on the line…collecting a cushy salary and waxing philosophical…

In making the “what’s next” decision in the face of a blank slate, I created a new set of filters…they were different than the first time I decided to start a company.  I had already been a CEO and gone through the process of raising money, building a product (sort of), managing a board etc…so just those activities didn’t feel like enough anymore…what I would build had to satisfy a more rigid set of filters.  Industry became much more important to me having flamed out in a market that I didn’t understand and never really figured out.  Team chemistry and DNA was a much deeper focus. Ability to generate revenue immediately was a new filter (b/c I wasn’t sure I’d be able to raise capital without traction now, and I was basically out of $ and living pretty poorly), social proximity to the value chain was a filter (or more broadly “actionability”)…and so on and so on.

I kept a spreadsheet where I power ranked all of my ideas by an aggregate of these various filters…and ultimately decided to jump back in and build what became Hyperpublic.

Now again, I find myself facing the blank slate. In many ways, it is blanker than ever before.  More is possible, less constraints, and more knowledge/domain expertise.  I have batted around a bunch of half baked shit over the past few months…not jumping into the blank slate fully…mostly because I knew it would be healthy and valuable to heal and recover from a hell of a battle with HP.  As the summer winds to an end and I walk along the beach, I have begun to bring some real process back into “what’s next?”  I always keep an ideas spreadsheet, but today on the beach I realized something that was causing me great angst.  I haven’t been able to build real conviction around a new goal/direction, and I realized it is because I haven’t built new filters…new to fit a new context…I am very gut driven, and my gut has held me back from many potential directions over the past few months…but that is just intuition listening to new filters that the mind has not properly articulated or realized.

Today I isolated the first major new filter that a new company must satisfy.  I made a new spreadsheet. Many of the filter columns are the same as before, but I added a box: “Would I be happy living in this company for the next 10 years (Y/N)?  This is not will this be successful or can we make money or can we do it or is this the direction the market is going or anything else like that.  This is, “change your focal length, don’t build to sell, forget about following your passion, passion is powerful, but this is will you be happy and comfortable in this space building this thing with this impact and mission, because once you push your stack in, it’s for the long haul. Reality changing innovation takes a long time to come to fruition.  The larger the vision, the longer the focal length and time it takes to get there.  Are you patient enough?  Can you live in this new vision and company for a long time, without getting bored or antsy?  Can you build a life and a family and identity around this new company? Is it sustainable, not just as a company, but as your company?”

It is a tremendously unforgiving filter, but it is now defined, and into the Fall we hurl, head first, and for the first time not angry or defensive, not with any chip on the shoulder, but wrought with anticipation, excitement, and a sense of pace…no need to frontload the conversion of ambition into action and energy. What does a company look like where we amortize our ambition and energy over a longer term horizon…still acting with urgency in the throws of the fight, but having bitch slapped the shit filter that is “satisfies my fear/insecurity of failure (Y/N)” so far down that it can only be heard on a day when the ocean is still and not a single wave crashes as we walk on the beach, contemplating what’s next.

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