Hacker Turned VC Can a hacker go to the darkside?

Mom: Wasn’t DEFCON the hacker event you went to when you were 15?

Me: Yes.

Mom: How did we allow that?

Me: You didn’t know because I didn’t tell you.

I went home to VT this past weekend to visit my parents and pick up this insanely cute kitten.

The kitten has nothing to do with this story, I just wanted to show her off.

Over dinner my father mentioned that he had heard an NPR story about DEFCON earlier that day. I was a part of the crew that put on DEFCON for 10 years, and I’ve been just an attendee more than a few times.

I had been at Purdue studying CS the summer before my senior year of High School. Ostensibly, it was to see how I liked the program, but I had hacker friends there and I mostly wanted to hang with them and read about the intricacies of the TCP/IP protocol.

I read this cover to cover that summer.

So that explained how they didn’t know that I went to Vegas. But then the question: how had I paid for the plane ticket. It took me a few minutes to remember; I sold t-shirts.

To finance my trip I created a t-shirt with two quotes.

Front: In this age of digital darwinism some of us are ones, you’re a zero.

On the back across the shoulders like a players name on a jersey, it said: 31337 

Which is Leetspeak for elite.

It also had a quote from the “famous” hacker Erik BloodAxe: I only hack for money

I borrowed enough money  from a friend to print a run, and then sold them at DEFCON. The proceeds were enough to cover my trip, and it was how I met the organizer, Jeff Moss, and became a Goon for the next 10 years.

I hadn’t thought about this in so long I had almost completely forgotten.

So I have a confession to make:  I own a pinball machine.  And not some little toy either, a full sized, modern, 300 pound piece of awesome. And what makes this really ridiculous is that I live in a studio apartment. So what does this have to do with investing? If you live in a NYC apartment and you buy a pinball machine, then you buy your absolute favorite.  You only have room for one, so you don’t settle. I love that Spiderman machine; it is, by far, my favorite game.  Since I only have room for one I didn’t worry as much about price, I went for the best. Early stage investing is similar, there are only so many deals an investor can do since their time is a limiting factor. And since the big winners are worth many times the initial investment, price is not as important. If a partner can only do one or two deals a year they have to choose the best, their absolute favorites.