There has to be something different about the DNA of entrepreneurs. Something in the blood that makes us look at the world through a different perspective. Something — either wonderful or terrible — that puts us very much outside the box. I come from a long line of entrepreneurs, following in the proud footsteps of both my grandfathers (an electrician and a silver plater) and my own father (founder of a series of successful software companies), and I couldn’t really imagine leading life any differently.

I’ve been an entrepreneur as long as I can remember, starting my first business in grade five. A good friend appeared at school one day with something quite surprising: his own, personalized letterhead. He pulled it out on the playground, proudly showing me the manila file folder like it contained state secrets, then revealing the striking black and white design inside. He had made them at his dad’s office, carefully lettering his name and address, drawing a personal logo, photocopying them on what must have been a fairly massive and quite new machine. He was rightfully proud of them and saw a long and shiny future of handwritten correspondence but I saw something different. I saw our ticket to untold riches.

I was wrong, of course. It turns out that our fellow grade fivers just weren’t in the market for customized letterhead. And, naturally, that the world had plans that didn’t involve a whole lot of handwritten letters. Never mind that, though. The important thing was that I bravely launched something, failed quickly, and learned a whole lot from the lesson. I’m on venture #3 now — 4 if you count the letterhead debacle — and I’ve certainly learned the lesson of customer development and the value of shoot first, apologize later. Plus, I have a whole pile of unused letterhead for all those fancy apology notes :)

—

Jay has been providing a human side to technology for over fifteen years as a technologist, user experience specialist, and visual designer. Jay co-founded and led Radiant Core, was the Head of Marketing at Rypple, and is now VP Strategy at Klick. He has been proudly published in the Harvard Business Review and wrote The Facebook Cookbook for O’Reilly Media.