High school, at Coral Gables Senior High, was probably when I really became an entrepreneur. Thing is, I never consciously set out to be an entrepreneur, it just came naturally.

In the beginning of 9th grade I’d been playing around with developing websites for myself, nothing exciting, simple stuff, hosting it on tripod or geocities or angelfire. I got a few friends together and we decided to make websites for other people, we called ourselves Internet Page Makers, or IPM for short, our website was pagemakers.net. We ended up building 1 or 2 websites before the team got bored and disbanded. That’s when I started Infinimedia, inc (the same company I’m running today, just different biz model).

I kept building sites here and there, and was into Apple computers around this time. This was when it was decidedly uncool to be into Macs. Apple was in a state of turmoil, I think there were Apple clones out, Steve Jobs wasn’t back at Apple yet. I found myself reading a handful of Apple news sites, and thought it would be fun to run my own (I wasn’t solving any problem, or really reacting to any clear market indicators, 100% because I felt like it. I was only 14 though.). So I built and launched Mac Mania (mac-mania.com – still have the domain). Mac Mania was one of the earlier mac sites, I ran news articles on it that I initially wrote myself, most of which were re-written press releases or sourced from other mac sites. We also reviewed products which companies sent me (I kept most of them, had no idea journalists weren’t supposed to do this). To make money off of it, we sold ads to various Mac oriented e-commerce stores. I eventually hired a group of writers, mostly teenagers, and paid them a few hundred bucks a month to write my articles. We had a network of sites (MacGamez.com, iMacOnline, iBookOnline, etc)

For the first two years of Mac Mania, it was very much a figure it all out as I go enterprise. I knew nothing about the online ad market, but most of the other people at the time didn’t know much either. At its peak we were doing 15,000 pageviews a day in 1999 on Mac-Mania.

Eventually I partnered with other sites and started selling ads for them on their sites, effectively creating a mac oriented ad network. I’m pretty sure this was ahead of its time too. At its peak in 1999 I was pulling in around 40k/year in revenue, paying out around 20k. So our margins were close to 50%, not shabby for a 17 year old’s business I was building in 10 hours a week after school and soccer practice.

After a few years, and the implosion of the dot com market, we folded up Mac Mania, which had rebranded to macinstart.com (bad move, lost lots of traffic).

So what did I learn during the lifespan of Infinimedia v1? I learned about building a product around something you were passionate about. I learned that if someone threatens to sue you, chances are you’re doing something right, and are at the very least getting lots of attention. I also learned that if you are forced to build the tools you need yourself to solve your own problems, chances are others have the same problem (we were very early in the display ad network business, but didn’t realize we were building tools we could resell).