TheWaterRat

As many of you know I am now focusing most of my efforts on my new venture, CityandOut. So, finally, for the last few months, I have been considering myself an entrepreneur for real.  I was of course aware of most challenges facing an entrepreneur, some for having been through before directly and some for reading a lot about all things venture, early stage and entrepreneurial.

I believe I am doing all by the books (if something like that were actually possible in startup land): I got a technical co-founder, we released early with lots of bugs and are fixing and adding stuff to the site as we go along, we have a few trusted and supprtive friends providing feedback and we are experimenting all the possible social web tools out there (we have a Facebook page, a blog, a tumblr, a twitter account, we are profiled on Tech Crunch, VentureBeat, YouNoodle, KillerStartups, BigStartups, RateitAll, etc. etc. etc.). We are actually getting some traction – our usage stats are ahead of my projections – and some positive feedback. We are doing the bootstrapping, I might say the ultra-bootstrapping. I am annoying people and getting lots of good stuff for free. We have experimeted and failed with outsourcing some of the development. I have self-taught myself html and CSS and even Photoshop and Illustrator (I wouldn’t want to be branded as the idea guy…. There’s no room for the idea guy). We are approaching softly some potential investors and other business contacts to slowly build interest until we have a decent website to showcase. I am obessing over the entire process everyday and every waking hour and I am loving it.

But, there are a couple of things that are bugging me a lot: speed of development and of virality or, better, the lack of both.

With regards to speed of development there is not much we can do about it. Mark, my partner is working all hours he can on it juggling another job; but it’s just him so there is not much more that can be done about it. My friend Nichol suggested we tried ‘crowd development’, basically offering a chunck of equity to all developers who can complete some features on the site for us. We are going to discuss this idea over the next few days and perhaps we’ll launch some sort of competition. In the meantime, any ideas, suggestions or tools that may be useful are all welcome.

With regards to the other problem I am getting really annoyed. I am experimenting with all possible tools and we are pushing SEO to the maximum we can given our current resources but we are not getting any viral effect or significant level of engagement. Nowhere near the level of traction some similar FB pages or websites are getting.

I have just had an email exchange and some conversations about it with some friends and the consensus seems to be that it’s not clear what CityandOut is about and that our message via Facebook or other tools is not focused enough. There are some easy and some less easy fixes to these issues and I agree that we lack some clarity in the message, in part by choice, in part by necessity, in part by mistake. I remain convinced though there is still something else missing I can’t quite figure out. Why would a FB page get 200,000 fans in 2 weeks (seemingly by chance) and another get less than 200 in a month? How do we get to the 200,000 mark? Does it matter?

There seems to be an issue of positioning as well – are we niche or are we cheap? these seem to be the obvious options. Ultimately, the objective is to be the cheapest and the best but that takes time and I don’t think it actually matters that much. I think it’s important to make sure you’re doing everything you can to be the cheapest and the best, and your users know about that (There are two kinds of companies, those that work to try to charge more and those that work to charge less. We will be the second – Jeff Bezos - Jeff, Amazon and I).

The beauty of this wonderings are that I am learning in the process and enjoying it and that I have some good people helping out with their feedback. In truth, I also think that most of these issues are easy to solve, it’s just a matter of fine tuning the message by listening to people and the market and adjusting as you go along. The challenge is staying sane while you push as hard as you can. Some days you get over the moon for something that is probably not particularly important, some days you feel like you’ve been beaten for hours by the Gods for no apparent reason. That is the beauty of being an entrepreneur which probably means that you are a self-involved, self-destructive, driven, compulsive and a bit crazy individual who likes to play (The man in the arena).