Bothsides of the Table


“It stops today.”

I spent the entire day yesterday in a deposition so I was offline from the world around me – a rare day of no email, no social media and even no news. I had been awake since 5am, returned home from work at 9:15pm and was exhausted with my only goal of decompressing and tuning out from the world.

I could not.

I barely slept last night. I read that a grand jury chose not to indict the police officer responsible for brutally killing of an unarmed black man: Eric Garner. I simply couldn’t believe it was true. I don’t remember feeling so angry at injustice in a very long time. I first saw the video of the police aggression towards Eric Garner when it was released and you probably did, too. If you haven’t re-watched it – as hard as that may be – please do.  If it doesn’t make your stomach churn, if it doesn’t bring tears to your eyes, if it doesn’t bring frustration to your soul and make your blood boil and make you want to shout, “STOP” from the top of your lungs – I don’t know what will.

In case you weren’t aware – the chokehold used by officer is banned by the NYPD as pointed out by this NY Times Op Ed.  In case you don’t know, Eric Garner’s death was officially ruled a homicide.  He was 43 and had 6 children.

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This week I wrote about obsessive and competitive founders and how this forms the basis of what I look for when I invest.

I had been thinking a lot about this recently because I’m often asked the question of “what I look for in an entrepreneur when I want to invest?” I look for a lot of things, actually: Persistence (above all else), resiliency, leadership, humility, attention-to-detail, street smarts, transparency and both obsession with one’s company and a burning desire to win.

In the comments section a clever question popped up about whether I would have invested in myself before I became an investor.

My first response mentally was, “Of course!” but then I realized I didn’t even need to answer the question. I had invested in myself for years. I quit a very well paid job at Accenture with very little time remaining before making partner and took a risk of having no job security at all. We had raised a $2 million seed round, which meant taking almost no salary so we could afford to hire staff.

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Obsession. The drive to succeed at all costs. When second place isn’t good enough because we live in winner-take-most markets. The desire to be better than anybody else in one’s field.

This blog started from a series of conversations I found myself having over and over again with founders and eventually decided I should just start writing them.It would often make my colleagues laugh because they’d hear me like a broken record and then the next week read my ramblings in a post.

Last week’s obsession was about obsession itself.

10 days ago I saw the film, Whiplash, which is one of my favorite films of the year. I would be shocked if it doesn’t win at least one Oscar. I won’t have any spoiler alerts here, don’t worry.

The protagonist in the film, Andrew, is a drummer and the story is his experiences in his freshman year of one of the most elite music conservatories in the country. He wants to compete to be the lead drummer in the competitive ensemble and study under Terence, an obsessive instructor who is hell bent on winning competitions for the school.

I absolutely loved the film. I loved the music.

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The story on Uber has been written about ad nauseam, which is why I’ve been reluctant to weigh in. But enough people have asked my perspective so I decided to weigh in with my non-conformist view. I love Uber and I don’t believe there has yet been a real scandal. Grievances – yes. But scandal? I’m not so sure.

For starters – I’m not an investor in Uber. I wish I were. I had a chance to be in the seed round and unfortunately didn’t do so. I didn’t invest in any of their fine competitors either like Lyft, Sidecar, Hailo, etc. I have no overt biases (we all have subconscious ones). I’m not friends with Emil Michael – I’ve never met him.

This post is nothing than a bystanders attempt to put this situation in perspective.

1. Is Uber evil?
No. That’s silly. It’s a fantastic startup that has had a amazing impact on society. It’s not just about people like me who can (and do) turn up in nearly any city in the US and immediately book a ride. On that front it has revolutionized my life. No more 45-minute queues at airports, no more stuck in the rain with no ride.

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One of the vivid memories I have from being a startup CEO is the feeling that most people in your company have a look in their eyes that like they can do your job as well as you. How hard could it be? You just assign out tasks to all of us.

In the early days the CEO is the jack-of-all-trades, doer-of-all, famously the “chief janitor” or coffee maker. But if you level up, raise capital and grow customers, revenue and staff – life changes. Eventually you need a VP of Product to handle your product roadmap, a CTO for engineering leadership and VPs of sales, marketing & biz dev. Most companies that are scaling have CFOs, heads of HR or talent. The “span of control” for a growing tech startup is probably 6-9 people. The “doers” in your organization.

This is when your job function truly starts to match the definition of “leader” because that’s exactly what your role is. You set direction. You hire great people. You help them prioritize their objectives and review the results. You course correct. You motivate, cajole, reassign tasks, hire, fire and push the organization forward.

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