Looking back on my career, many of my biggest mistakes were not taking myself as seriously as my co-founder. My first startup was nkdguru, a company I was brought into due to another co-founder who was leaving. It was a Java Struts app. That means it used a language called Java and a web framework called Struts. Struts was an MVC framework for Java. I knew a little Java from my programming days in first year university but had never done web programming before. My HTML and CSS experience was limited to a Lynda.com course and building my Dad’s website, rossfenwick.com.

While eating pasta at East Side Marios on Front Street, sometime in June or July, I signed up to join the nkdguru team. Our fearless leader, Andre Charoo, was thrilled to have me onboard and I was too. They called me a CTO, I was 20 years old and had been programming for 2 years, I felt really good about this.

I hated Struts and quickly ported the entire site over to Ruby on Rails, that felt better. I felt more like a CTO too. Here’s the thing though, I wasn’t really the CTO, I wasn’t even really in the company. I mean I was, but I was going through the motions, just playing a role really. Andre was in, he had business plans, he had investor meetings. He had a vision. I just listened and said, “ya I can build that”, I am the CTO after all. It all feels so stupid in hindsight, nkdguru was a good idea but I don’t think I really knew that. I didn’t even want to be rich and famous, I didn’t want to move to San Fransisco or anything like that either. I think I just wanted to build stuff.

Incentives play a huge role when it comes to projects, not just financial incentives but mental ones too. For Andre, he wanted to be rich and he wanted to get away from where he came from. He was too good for Ajax and dreamed of NYC and SF, the startup was a means to those ends. I didn’t take my job that seriously, I mean I built everything, I worked long hours, I took calls I did everything to make it look like I was serious but I would still help my wife’s company with their servers and computers to earn my living. I was still building this company, Ewakened, I was making websites and charging people for them.

Looking back we could have made it. We could have been 10X more successful than we were, but I didn’t realize what it meant to be a co-founder then. It would take me a lot longer to learn that lesson, in fact I think I am still learning that lesson now. If there is advice to be had in this post, it’s this: if you are going to spend your time on something with someone know why you are doing it and make sure others do too. I wasted so much time and time is all we really have. I wouldn’t trade it, Andre and I are still friends, without Andre and those early experiences, I wouldn’t be where I am today writing these words, but what did I really do? If you are going to spend time, time that you could have been taking and laughing with those you love, time learning new things, know why you are doing it. Don’t wander aimlessly through life. Have a purpose for everything that you do.