Great question. Someone asked me about funding last night at the HN Chicago meetup. In all honesty, I haven't thought a whole lot about it. I reached out to

Great question. Someone asked me about funding last night at the HN Chicago meetup. 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.