Both Sides of the Table


 

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. I loved the intensity. I loved the drive to succeed, to compete and to be one’s best. As you can imagine – all great films have conflict and the tension is this – what is an acceptable level of obsession to put into success, whether instructor or student?

The rest you should see for yourself.

But the film has my brain buzzing all week about obsessive and competitive people. Think about Kobe Bryant. Kobe is famous for waking up crazy early every morning and practicing for longer and harder than nearly anybody else in the NBA. Kobe isn’t Kobe just because he was born naturally tall and athletic – although that is a

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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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I was at a dinner recently in Chicago and the table discussion was about building great companies outside of Silicon Valley. Of course this can be done and of course I am a big proponent of the rise of startup centers across the country as the Internet has moved from the “infrastructure phase” to the “application phase” dominated by the three C’s: content, communications and commerce. But the dinner discussion included too much denial for my liking.

I think startup communities being simple cheerleaders doesn’t help anyone. Those of us outside Silicon Valley need to make an effort to effect change not just wish for it.

At the dinner some of those arguing that Chicago has everything it needs now that it has built: GroupOn, Braintree, GrubHub and others and that it has “come along way” and “will never get the full respect it deserves just because it’s not Silicon Valley.” But I think this misses the point. I’m a very big fan of Chicago. I started my career at Andersen Consulting (now Accenture) so I went to Chicago many times a year for nearly 9 years.

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Let me start with the news that I’m excited to share with you. After years of trying to persuade Kara Nortman to become a partner at Upfront Ventures I can officially announce now that she’s joined us effective immediately.

I have known Kara for 7 years and knew almost immediately after meeting her that I wanted to work with her one day in some capacity. Thus began my marketing campaign. It is rare to find somebody who matches exactly what I’m looking for in a partner so when you find it you act:

Academic rigor (Princeton undergrad, Stanford MBA)
Competitive (Athlete: skier & rowed at Princeton, hates losing at everything she does)
Investment experience (5 years a VC at Battery Ventures)
M&A experience (Morgan Stanley and later co-headed M&A for Barry Diller at IAC)
Operating experience (Helped run parts of CitySearch & UrbanSpoon, tons of product management experience, Board of Hatch Labs which helped spawn Tinder)
Startup CEO experience (Founded P.S. XO along with my good friend Soleil Moon Frye.

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