Why I Look for Obsessive and Competitive Founders

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 sine qua non.

Kobe is kobe because he practices more than even the most elite professionals in a hyper competitive industry and because he is simply more dedicated to his success than many other people are.

In our society we revere athletes. We revere musicians. We glorify their successes and we marvel at their achievements.

Yet somehow many people think that startups intended to operate at massive, Internet scale can be casual affairs. I see founders who think they can be at every conference, advise multiple companies, do side investments in angel deals, leave the office at 6pm and have a balanced life. I don’t believe it’s possible to compete at Internet scale and have balance.

I’m not making a qualitative statement that I believe obsession in startups is necessarily a good thing. In fact, I have written about the negative health consequences and sometimes mental consequences of doing so.

But I would make the observation that if you stumble on to a really important idea that has the potential to be really valuable know that others will enter into the market precisely because markets are competitive and a lot of money and prestige is at stake. In fact, think about it. Even MORE money is at stake than what Kobe or even the best rock bands in the world can make by being at the top of their game. Zuckerberg. Larry / Sergey. The founders of DropBox, Airbnb, Uber — you name it.

So if you’re going to raise venture capital and compete in large, growing, winner-take-most markets you had better be prepared for other people to want to knock you off your stool, steal your limelight, grab your customers and muck you up.

I don’t know Mark Zuckerberg. But I’m willing to bet (and certainly from the profiles I’ve read) that he was pretty obsessive and all in at Facebook for many years (if not still) to drive their success. It isn’t as if there weren’t other people trying to dethrone Facebook all along.

I write all this because I am constantly asked “what I am looking for when I make an investment” and the most honest answer I can give is that I’m looking for maniacally driven individuals who are obsessive in their pursuit of an idea and who are so competitive and driven that they can’t accept failure.

I know it sounds cliché.

But I would ask you this. If it takes compulsive individuals to be at the absolute peak in sports or music — why wouldn’t it take the same to create a disruptive product or service that can change an industry. It’s not a 9-to-5 job. It’s not for people with soft elbows or compressed egos.

I look for many things. I’ve even written about the Top 12 attributes of an entrepreneur here (each number is clickable).

But I’ve also got to be able to observe the inner Whiplash.