How did I become an entrepreneur?

To learn how to become an entrepreneur I’d first have to ask myself why I want to be an entrepreneur. The answer to that now is the standard, traditional, not very exciting or unique response of: I want to build something that changes the world, have my own company with my own culture and challenge myself everyday. Right.

What’s odd is that I never once did ask myself “why do I want to become an entrepreneur?” Why not? Because I never wanted to be one, at least, never intentionally. It wasn’t my aspiration to be one, it wasn’t even a thought in my mind.

That’s what makes the story of how I got to where I am now and how I ended up an entrepreneur a bit more interesting…

I’m an entrepreneur today out of trying to take shortcuts and a lack of identity.

In high school I was an avid gamer (counter-strike 1.6). In fact, I was pretty good. That said, I wasn’t a professional eSports level guy and never got to travel to the cool tournaments or make money playing games. So what did I do? I went on mIRC, lied about my age and told some international multi-gaming organizations that they needed a head of US operations to take advantage of the US sponsors/market. This was my excuse to help the organizations while getting free rides to tournaments, events and being a part of the scene. I was 16 at the time and had no clue what ‘US operations’ even was. Didn’t matter, it worked (somehow)! A German multi-gaming organization picked me up and I went ahead with my plan. Not for the job really, but I sure as hell wasn’t going to become part of the scene through my skills in the game. This was my first opportunistic shortcut.

Next, I dropped out of high school at 17. No, not to start a company or be the next Silicon Valley whizz kid. So, why’d I do it? Well, I went to a private all guys Jesuit high school, Bellarmine, with amazing academics and even stronger sports. I transferred there after attending a public high school for my freshman year. At my public high school, I did quite well. I was in speech and debate, did really well at school and things were looking hot. At Bellarmine though, everyone was smart. Everyone kicked ass at a sport. I was thrown into the mix and had no clue how to stand out. While everyone was dominating their SATs, I was doing average. While everyone went to state championships, I was the soccer team manager due to bum knees from cross country and a lack of humility to just play JV. I was just another person in the mix.

So, when the summer after my junior year rolled around and I had a chance to be a black box QA tester for Yahoo! Mobile, I made the jump without even a flinch. Dropping out of high school is not that okay in society, but I was that determined to, just for the love of god, do something that would make me stand out. It was a severe lack of identity that had me not looking back for even a second. Keep in mind, black box QA was not a dream job or even a remote interest of mine. It was literally just something no one I knew had done before at my age. I think I was the only guy at Yahoo! that was kicked off a team (mobile search) for being underage during their release of adult content.

Now, I did get the opportunity to work on my own project to bring the pro gaming industry into Yahoo! as a content vertical through Yahoo! Mobile apps. But, I doubt they really took me seriously considering my pitch was 50 slides long and took an hour and a half to get through (thanks Ben Strong and Kyle Laughlin for not falling asleep!).

After a year and a half, it dawned on me that I needed to get out of QA or that would be my life…forever. My only option really was to get back into the swing of things at school as I didn’t have the credentials to take another serious position outside of QA. I also realized I had a lot of growing up to do and so I didn’t want to attend school for vocational training but really just to mature as an individual.

Fortunately, I got into UC Berkeley and studied Philosophy. Talk about being just another person in the herd….Berkeley was even worse for me than Bellarmine. I went from being a 4.2 student in high school to a straight B+ student in a school with 35,000+ students - many of whom kicked my ass academically. So, what did I do? I rebelled. Instead of attending class, I built a digital whiteboard social network on buddy press (Wordpress extension) in the world of dream theory. I worked at a magazine company helping them with SEO and building a mobile app as print publishing in ‘09 was desperate to get into digital. All the while sort of attending class. At this point, academics were going nowhere, so I was constantly on the prowl again for anything to get me back out in the world doing something that others around me weren’t. To regain my unique identity.

Then….the inevitable. I got a job offer and dropped out of Berkeley to join AOL at the end of my sophomore year at age 19. I was helping the team with buy vs build for mail and mobile, which was great. Though, 5 months in, I quickly realized I am not a big company guy (politics totally ruin the fun) and went on to co-found trigger.io for nearly 2 years. Just 6 months ago, I was granted the opportunity to finally be the founder and CEO of my own company, AdStage.

From AOL onwards, it was your typical story of wanting to have my own company, my own culture and wanting to change the world. Nothing wrong with that at all and I love it.

But, it’s important for me to remember how I really got here. It wasn’t my last 3 moves, but my first 3. It was my obsession with standing out due to a lack of self-confidence/esteem/identity that I just said “to hell with it” and ran with anything that could set me apart and make my story just a bit more unique.

So now, when I ask myself why I want to be an entrepreneur, the answer is simple - being an entrepreneur makes me something.