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

How I spend my time as a startup CEO

Posted on November 27, 2013. Filed under: startups, venture capital |

Last night I had the following exchange with Semil on twitter:

“@jordancooper what does it take to be startup CEO, in first year? can you squeeze it into 140?”

“@semil vision, ambition, empathy, discipline, passion, humility, language, listening, hustle, support, great cofounders, special team, love”

I responded in an instant without deep thought or analysis…but those are the ingredients that I guess were top of mind…my gut response. It was an unusual position to find myself in…where someone well respected and authoritative in the startup community was asking me, as a CEO, what I believed it took to be good at my job…embedded in the question was an assumption that…well…I am good at my job. Having been in this seat, now 3 times, this is the first tour I’ve done where I am not constantly defending myself and my worthiness in the seat…that is a huge part of being a founder…and a young founder…simply justifying that you are good enough to warrant the position you’ve assumed…so before going forward…i guess…thanks Semil for believing in me. Anyway, beyond the personal characteristics and components that I find valuable as a startup CEO, I have been spending a lot of time recently thinking about…well…time. How am I spending mine? Is this optimized? Where can I change or improve or shave or reallocate to be more effective as CEO of Wildcard. I go through this process of self analysis every so often…it is usually when my activity is breaking the structure that I had previously put in place…i feel sub-optimization in my body and my mind…I go from energized to exhausted…and from consistently thoughtful and creative to spottily thoughtful and creative if that makes sense…spurts of magic as opposed to flow states…anyway…recently I have been feeling my structure cracking…not yet broken in the sense that things are moving forward and fast…but I can sense that a reflective optimization is on the horizon…

Generally I have two goals as CEO of Wildcard.

1) Support the exceptional people I sit next to everyday in any way I can. This can be in thought, in emotion, in sustenance, in vision…whatever I can do to unblock and unleash the greatness in everyone else…I will do…and the time I spend doing this, weather it manifests in something as mundane as taking out the trash, as substantive as an analytical conversation, or as nuanced as a thoughtfully timed hug…these actions are always optimized and priority..the time I spend thinking about and caring about everybody at Wildcard will never fall to the coming reoptimization.

2) Clear everything else off my plate…every task…every to do…every meeting…every request…and find the time and space to focus on the one thing that will push us forward the fastest and most dramatically…that thing can change from moment to moment…but more realistically it changes from week to week or even month…One month it can be “secure investment,” another month it can be “better define product” and another month it can be “recruit Design Leader”…but generally I find that I can maintain many balls…but really only excel at one important thing at a time…if “excel” or “excellence” is a true requirement of the task at hand. Context switching is a big part of my job…being able to dip in and out of different problems and questions and thoughts…while contributing meaningfully to each….but every switch takes a toll…which is why i try to only switch off the one most important thing when it is in the spirit of supporting someone on our team to achieve their “one most important thing.”

So how do I clear every moment and task that does not fall into one of these two categories and make space to do these things well?

1) extreme honesty and discipline: I say no to a ton of meetings, a ton of emails, a ton of opportunities…with no remorse and sometimes lacking a little bit of social grace (although i try to be human about it). I’ve never had a problem saying no before…it’s a requirement of time optimization.

2) I invest in people who are better than me at everything I do. I constantly look for ways to replace myself…to upgrade in areas where I can push things forward…but not nearly as well as someone better than me…I pay deep attention to my efficiency in all realms…and sense when I am not achieving the desired result in the same amount of time as another could…that is an opportunity to upgrade

3) I force reflection: at least once a week, and often once every few days…no matter how focussed or involved I am in a given task, I force myself to look at my own time and our entire business from a birds eye view…I write out priorities and observations on blank index cards…and I visualize my own and our team’s efforts in semi-real time as opposed to on our traditional 90 day roadmap axis…

4) I walk to and from work every day: I know this sounds like a sub-optimization of time…but in fact it is built in, uninterrupted focus within the chaos of meetings and conversations and inboxes and bullshit…it is a meditation that actually calls less on directed analysis and more on surfacing the things that are “running in the background” of my mind…this is key for me…because awareness of what’s going on can be stifled by concentration and focus…I need space to surface the unsolved…and my walk is that space.

5) I am disciplined about believing in my decisions. I would estimate I make about 10 decisions a day that impact our company…some of them are big…some of them are small…but once they are made, I almost never look back…they will not all be right…often they are…but second guessing or even reexamining in the absence of new information or data is a complete waste of time and energy.

Anyway, I’m sure there are more, and I could go on this track for much longer…but I’ve been writing this post for over 20 minutes now…and I am getting diminishing return on these next minutes…I’ve written to the point where I understand the thought I was trying to explore…time to get back to the “one thing that will push us forward the fastest”…in this case…it’s finding a truly excellent owner of this position and side of our business. Happy Thanksgiving.

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