15 Minute Interviews, The Cockiness Saga, and The Future of the Digital Space (Oh, My!)

I had a 15 minute interview today with an investment firm I have  a lot of respect for.  They tend to think about similar things as I do: things like digital media, education, and the transformative effects of the internet. They’ve done a great job of this.

15 minute interviews are tough and are always a little bit frustrating.  Not a whole lot of information can be communicated, and the results tend to have a much higher variance in my opinion.  After the interview, you’ll inevitably say to yourself, “Blast!  I didn’t get this huge point across!”

Whether it’s a pitch or an interview, short conversations such as this are a great exercise in communication.  You have to really try to get across the key points you want to say succinctly, and be polite about taking the conversation in the direction you want it to go (especially if you’re giving a pitch).  This particular conversation reminded me of a tamer version of my ~15 minute interview with Paul Graham of Y-Combinator (hopefully it went better…. )

A few of the questions are the same questions I figure some of my readers have also asked, so I’ll go ahead and address them:

On the “About” page of my blog, I mention that I consider myself to be “cocky”.  One of the questions I got was whether or not I was humble, as this was an important part of the job.  I mentioned that my father was a missionary doctor, I grew up in one of the poorest counties in the US, and that I had an upbringing that focused on humility.

However, I did not mention the fact that less than 3 months ago I was moving furniture on the weekends in order to live (very tough work, I have a lot of respect for the guys I worked with), that I had been turned away numerous times when I was raising funds for my startup, and  that my ideas have been completely shot down numerous times.  These things are very humbling.  However, without a certain level of Cockiness, I would’ve never had these experiences.  Thus, Cockiness has actually lead me to a greater level of Humility.

(Cockiness is good so long as it’s tempered by humility–otherwise it turns into Arrogance.  I acquired my cockiness later in life because I realized I needed it. I talk a lot about this in my book as it relates to the very Powerful Persona, The Cocky Son-of-a-Bitch. In a comment on my book, Bryan Hernandez captured a key delineation of Cockiness and Arrogance quite well, “Cockiness is an attitude towards the future, arrogance is more often an attitude towards the past.”)

The other thing I was questioned on was whether or not I have a position and thoughts on the future of the space/industry, as this is very important.  By this he was curious as to whether or not I have a position on what I refer to as The Digital Space.  I should’ve said, “Boy, do I ever.”

And with that, I’m happy to announce that, with the completion of my book 10 Powerful Personas (and completely unrelated to this interview), I can now continue my series of essays on The Future of the Digital Space.  I’m very excited about this. Keep a look out for them.

-Kevin
4.30.2010