You must play to win....

An excerpt from Entrepreneur turned VC, Mark Susters blog: Both Sides of the Table...

One attribute that I believe most VCs look for in entrepreneurs is competitiveness.  I know I do.  I like to work with people who hate to lose.  Anyone who has ever been around me when I’ve lost at anything I care about will tell you I’m not pleasant.  I’m not a poor loser at all.  It’s just that I stew on it.  I don’t recover easily.  I lose sleep.  If I have any angle of changing the outcome I will.  I replay things in my mind about why I lost and I try to correct my mistakes.  

I look for people who share this obsession about winning.  If you stumble on to a really good idea believe me it will get competitive really quickly.  It amazes me how quickly a modest success story gets replicated and any initial product / market advantages get narrowed.  You can’t accept simply ceding part of the market to someone else because it’s big.  You need to fight for every inch.  Every win.

The trait spills over from personal life to business and back again.  My wife finds it curious.  Family scrabble games are fun – but I still want to win.  We played against her parents and I was focused.  I wanted to take them down!  Poker night is social, but if I’m playing, it’s to take your money.   GuitarHero is seriously chilled out way to hang out with friends.  But even more so if my score is higher than yours.  I ran a marathon with my colleague in 2003 – I’m still bummed that he beat me even though he was clearly more athletic.  For me winning IS the fun.

I know that people who aren’t competitive always find competitive people slightly distasteful.  They feel that there’s something egalitarian about everybody getting a trophy.  They complain that trying to win at everything is in being over zealous and is unnecessary.  Maybe.  Anyway, I’m sure this will play out in the comments section – it won’t be the first time I’ve heard it.

It is what it is. But I want to work with people who thrive on winning.  I look for that fighting spirit in those that present to me. Entrepreneurs play to win and they take losing seriously.  Think Mark Zuckerberg doesn’t have some sleepless nights about Twitter despite having more than 350 million users himself?  Think Yelp doesn’t wake up daily thinking about how to crush FourSquare?  Think Marc Benioff is content with being a billionaire?  I’m sure he seethes at any losses to Larry Ellison.

Steve Jobs is famously known for being obsessive about people not leaking Apple information prior to announcements (unless it’s intentional.)  It is rumored (and much debated) that Jobs dropped McGraw Hill (the book publisher) from any iPad announcements because their CEO went on CNBC the day before and talked about the iPad.  Certainly sounds plausible to me.  You don’t like leaks? Send a message and people will think twice next time.

leo the lipDon’t take it from me.  Take it from Leo “The Lip” – “nice guys finish last.”  Steve Jobs isn’t a “nice guy.”  Nor are Bill Gates, Steve Ballmer, Marc Benioff, Larry Ellison, Tom Siebel, Rupert Murdoch, Barry Diller or any number of people you’ll find who built empires.

I’m not looking for people to be mean and certainly not unethical.  Just people who play to win – every time.