Post-mortem report of my free online dating service; Part 1 of 2

By | February 7, 2011

I registered the domain for my free online dating service,, in October of 2007. I decided that along with making my first real startup that I would invest money in that it would be a good idea to do in a language I didn’t already know (ASP.NET), with a database I wasn’t familiar with (MSSQL) and on a platform I had not deployed anything on before (IIS6).  My thinking was that along with creating this sure fire website that I could make money though advertising off of I would try and learn as many things along the way as possible. I worked on this project in my evening times while also supporting a medium-core World of Warcraft habit. When I say something took days of research it’s real time passed after work, WoW and a little life.

I had modest goals to measure the success of the site. My first goal after launching was to make more money than I spent in hosting and advertising. After that I wanted to invest all actual profits back into the site so it would continue to grow. I pictured a power point graphic of exponential growth and with a little patience I would be rich!

I broke the site down into smaller and smaller chunks and for every small milestone or functionality I completed I patted myself on the back. Milestones such as getting Visual Studio Web Express to pre-compile DLLs so I didn’t have to place source files on my webserver, which I had none setup at the time, or migrating my new found zip code database from MySQL to MSSQL. Every step I took involved several days of thinking and research.

I swear it wasn’t intentional but I felt like I put as many technical obstacles in between myself and launching the site as possible. I vividly remember spending several evenings, days I felt like, trying to decide on which source control solution I should use. I kept hearing Git this and Git that at the time but it took me a while still to figure out there was no easy way to run a Git server on my home Windows machine. I finally settled into VisualSVN and celebrated when I checked a file in from my laptop and got latest from my desktop! I was on my way.

I stressed over membership and security for a long time as well. Don’t store passwords in plain text, watch out for all user input and SQL injection worries. I had created a pretty full registration and login web of pages before I even thought about creating a admin interface for my users. That’s no problem I thought at first, Visual Studio Web Express came with this very helpful ASP.NET Web Site Administration Tool that I found out, after several more nights, couldn’t be installed remotely on my newly acquired shared hosting environment. Screw it! At that point I had a text file of SQL scripts I was running to do development work that ended up being my “admin” interface to the site.

I had been using my free time since registering the domain working on the site and learning C# but by December 2008 I still seemed far away from launching anything I was proud of. I was doubting my plans and if I didn’t do something drastic soon I would never launch the site. In January 2009 I quit playing World of Warcraft, I disbanded the guild I had put together, transferred onto another server and kept no ties to anyone I knew. Even my real life friends didn’t know where my characters went. Shortly there after I actually canceled my accounts. Suddenly I had all the time in the world during my evenings to work.

Within 5 months of cutting out video games I was able to launch the site in May of 2009. I actually did a soft launch first, running through all of my test cases a few times just to check for any obvious bugs. All of my testing, research, learning and code was live. It took me far to long to get here I told myself and I knew that the hardest hurdles were still to come. No one knows me, I have no track record of success, how on Earth am I going to get people to sign up or even visit my freshly unwrapped free online dating service.

Continued in Post-mortem report of my free online dating service; Part 2 of 2 to read about the end of DiveIntoThePool

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