At this time, Matt was admittedly more of a programmer than I was.  While our web "programming" skills were roughly equal, Matt was also into C/C++ programming.  He wrote an Asteroids-like game to teach his brother math, and he would dissect gaming engines like the one used in Doom.  At one point we even thought of developing our own first person shooter based on our neighborhood and school, the premise being, we had to rescue everyone from zombies and aliens.  Again, youthful ambition, and not a bit of naivety.  Sometime in 1995 or 1996 we registered our first domain name, perplexed.com, with a $100 investment from my grandmother.  The name "perplexed" represented everything about us at the time: young and curious, but sometimes confused about the state of the world we were in.  Why did people do certain (illogical) things?  What were we going to do with our lives when we got to college?  Will the Knicks ever beat the Bulls in the playoffs?  It is my contention that perplexed.com is the greatest domain name ever registered, and I cannot articulate how angry we are with ourselves that we didn't renew it. More on that later

We decided perplexed.com would host two different sites: Matt's Game Programming MegaSite, and my VB Programming MegaSite.  This arrangement allowed us both to build sites related to our interests.  We tried to keep the layouts the same so we'd have a consistent design across the domain; two frames, the left being the menu, the right being the content.  The color scheme was black background with white text.  We tried to make all our images using PhotoShop.  They came out ok in a cheesy way, as you'd expect from two programmers.  GPMega would focus on all aspects of game programming, especially engine design and DirectX.  Matt had a ton of C/C++ code up, as well as tutorials, links, software, and even a MIDI player so you can listen to a MIDI version of Van Halen's "Panama" while you browsed.  VBMega was concerned with Visual Basic programming, and the main focus was on programs that you could use to manipulate earlier versions of AOL.  For example, posting ASCII art in chat rooms, knocking people offline, pinging the service every few minutes so you wouldn't get knocked off, as well as other more nefarious features.  I ran this portion of the site, which allowed me to learn VB programming while at the same time piss off my friends by booting them off AOL over IM.  Everyone was a winner!

We made money the old-fashioned way, by selling ad space.  We signed up for various banner exchanges before settling with 24/7.  They had a different name back then, I just can't remember what it was.  In any case, the sites both grew very quickly, and the checks were arriving.  The first few months we made $150, then $200, then $300.  At the high point we were pulling in $1500 a month, strictly through ads.  When you're 15 years old in high school and you're walking around with that kind of money in your pocket, you feel on top of the world.  While the rest of our classmates ate the cafeteria food, we walked over to the deli across the street and treated ourselves to bacon egg and cheese sandwiches.  Going to the mall was fun: your girl wants some lunch?  No problem.  New shirt?  Done.  New programming book?  Buy two!  One month, perplexed.com accounted for a little more than 1% of the total ad impressions for every site that advertised with 24/7.  We were experiencing impressive growth.  Perhaps the most stunning thing to happen to us during this time was one day when we were in CompUSA.  Matt was leafing through a book, Tricks Of the Windows Game Programming Gurus, when he saw GPMega mentioned!  We didn't even know the author had referenced us.  It was shocking; we were open-mouthed.

Unfortunately, all good things must come to an end.  In retrospect, the way Perplexed ended is sad indeed, and the only way I can explain it is stupidity.  In October of 1998, my family and I moved to another town, which was only 15 minutes away from where Matt lived, but to two kids with no cars who would now be going to different schools, it might as well have been a million miles.  We kept in touch and continued to hang out, but it was hard to run the sites at the time.  So many of our ideas came from lunchtime brainstorming, playing ball after school, or Friday night coding sessions.  Now that we weren't seeing each other on a day to day basis, the importance of the sites and the partnership that created them began to fall.  It sounds insane in this age of telecommuting, but back then we didn't know any better.  And priorities changed as we got older.  When you get a new car and you're hanging out with your girlfriend, and doing whatever high school kids do, who wants to be up at 3am on a Friday writing HTML and answering emails?  The nail in the coffin was the failure to renew the domain name.  To this day I don't know why we didn't do it.  I can't explain it; it was a stupid decision and one of the biggest regrets of my youth.

At this point, Matt and I are seniors in different high schools, preparing to attend different colleges.  We're still great friends but the lack of face time has meant that our priorities diverged a bit.  It's worth mentioning that my grades were better in high school and college after I moved away.  I failed out of Advanced Math in seventh grade, but got A's in Calc I, II, and III in college.  Go figure!  In all seriousness, the fact that Perplexed.com is now part of an ad farm is a huge source of pain and regret.  But all is not lost.  Stay tuned for Part III, where I will bring the story up to the present time, and offer my reflections on the business and pleasure of web programming.

Related posts:

1. 13 Years On The Web – A Retrospective, Part I
2. Ad Revenue as a Business Model – Eat Dinner First
3. Breaking Radio Silence