My Startup (WindyCitizen) named one of Chicago's New Essentials

My Startup (WindyCitizen) named one of Chicago's New Essentials
chicago.timeout.com

In all honesty, I haven't thought a whole lot about it. I reached out to alumni entrepreneurs from my university when I was starting Windy Citizen to get advice. One of them, a guy who works in VC in the energy field, pointed out that I had no clue what I was doing, so:

a) Evaluating a technical partner would be extremely difficult. b) Evaluating potential angel investors would be just as hard.

He offered to give me a call every Sunday for a year for advice and moral support if I promised to go it alone for one year, build my own tech (tricky considering I'm a decent designer but not a backend guy), and not take any money from anyone.

That first year was miserable as I iterated through a few versions of the product and lived on about $10k that I earned from freelance writing and design gigs. The first idea was to build a big blog network for Chicago. I found about 20 writers, but ran into two big problems:

1. Drupal's content creation forms are not suitable for non-technical users or people without special training. They have some WYSIWYG add-ons, but they're frankly terrible compared to Wordpress/Squarespace/MT. This meant I had to post up most of the blog posts myself and my writers were always frustrated and demoralized. On my end, I lacked the skills to build a good writing UI or the funds to hire someone to do it for me.

2. With my time swallowed up by posting and editing stories, I had no time to even worry about ad sales or recruit new writers. I think a local blog network could work really well...if you had 2-3 guys. As a solo project, no dice.

So 9 months in, I switched to letting anyone join up and share links to their favorite local news, blogs, and events. We've been doing that for the last 14 months. Midway through that, I picked up someone to handle ad-sales on commission with some opportunity to earn equity in the business. Together we've reached a healthy "ramen profitablity" position and are having a lot of fun.

4 months ago, I scored a $35k grant from the Chicago Community Trust to invest in our tech. We've spent a bit of it on performance improvements and are looking to spend a bit more on FB/Twitter integration (if you're good at that stuff, drop me a line!).

So I've been pursuing the slow growth strategy. All bootstrap so far. I believe we're very close to "cracking the code" for doing this sort of thing which then could change things a bit, but in the meantime we're working on incremental improvements to our sales strategy and product.

Please don't give away any information that might hurt you or that you would be uncomfortable sharing.