My Startup (WindyCitizen) named one of Chicago's New Essentials | Hacker News Reader

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

chicago.timeout.com

68 pointsbrandnewlow38 comments

Congrats! No obligation for you to answer, but have you raised any funding yet? Would you be able to spend a lot of money to scale more rapidly or is going more slowly a better strategy for you?

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.

Could you elaborate more on the process of getting the grant? That is an avenue of funding I would love to hear more about.

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

I wish there was some magic to it. I've only applied for stuff that was aimed at supporting new news-related ideas. So far I've applied for 7 grants and won one of them. I have two applications in the hopper right now but both are longshots.

For this grant in particular, the Chicago Community Trust announced it had $500,000 and wanted to give it to Chicago-based, Chicago-focused, news-oriented projects. About 70 people applied and they gave money to 12 applicants. I received a little less than half of what I requested but am extremely grateful and excited to have some cash to play with. Considering the criteria, I probably would have done something drastic had I not made the cut for that one... :)

How do you hear about these grants? Are there any sites that specifically focus on available grants?

Here's a great example of how our users feel about Windy Citizen: http://www.windycitizen.com/chicago/media/2010/02/25/windy-c...

<blockquote>The nice thing about Windy Citizen is that is embraces a diversity of views -- even allowing stray libertarians and organic conservatives on board -- along with the usual multitude of bloviating Chicago nanny state enthusiasts. I just wish that WC could get someone to work out all of the computer programming glitches.</blockquote>

> 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.

sounds like a great guy, really good of him.

Yup. His friendship has been a big plus through this. Being buddies with his buddies who he's roped in to help from time to time has been another big plus!

Could you elaborate on your experiences of building out an ad sales program/team?

How much traffic did you have when you started selling ads? What type of CPM are you able to see?

The reason I ask is that I run a niche community site that gets a decent amount of pageviews but I'm not sure how much I could make by selling ads against it.

I found my ad sales person by asking for help on HN. See my post further downthread for the link to that thread.

I've interviewed maybe half a dozen sales people and worked with 2-3 who didn't work out. I have no advice other than to say it's really hard to find someone good. A great ad sales person is someone who wants to make a lot of money. Those people typically steer clear of early stage ventures because there might not be a lot of money to be made. That leaves people who are ok with not making a lot of money. If you hire those people, you won't make a lot of money.

I started selling ads on day one. It's always possible to find someone at some price who will want to advertise on your web site. We see extraordinarily high CPMs on our site because we work very hard to sell them on the quality and uniqueness of our audience. Basic salesmanship stuff.

Thanks!

Do you mind sharing how much commission you pay your ad sales person?

How is Drupal working out for you as a platform?

Lol. See comment above. Drupal's great at solving 80% of whatever problem you have. Unfortunately, consumers expect and deserve a finished product. So you either need to be a dev and hack your code yourself or hire someone else to do it for you. Very little "just works" out of the box in a way that consumers would recognize and take to.

Congratulations! What are some good examples of feedback from HN that helped you get there?

HN has been my secret weapon from day one:

1. You helped troubleshoot the first of my epic hosting/performance problems and helped get me onto Slicehost http://news.ycombinator.com/item?id=326012

2. You helped me find a dev to build a Twitter tracker for the special election to replace Rahm Emmanuel in Congress http://news.ycombinator.com/item?id=466468

3. You helped introduce me to my biz-dev guy (an HN reader forwarded this onto him) http://news.ycombinator.com/item?id=670204

4. And so on, and so on.

Congratulations! I see GrubHub is there, too. It's great to see the increased number of startups in Chicago, which is, you know, not a big startup hub.

Yes indeed! Last night's HN Chicago meetup was a lot of fun. This is the third or fourth one we've had. There's a great mix of bootstrappers, VC-types, CTO-types, and gainfully employed devs looking to make the leap.

Shucks, I didn't know we had HN Chicago meetings. I joined the Google Group. Will be there next time.

I'm in the same boat. Could you post a link to said group, if it's not too much trouble?

EDIT: Found it. For any looking: http://groups.google.com/group/hn-chicago

Where the fuck were the gainfully employed devs looking to make the leap when I was there? I didn't want to move to Boston... And it's baseball season, to boot. :(

There's always a gap between what people tell you over beers and burgers at an HN meetup and what they're actually willing to do...as you found firsthand...

Had a great time last night at the meetup. Didn't get a chance to meet you though! FYI, I'm in the latter group above.

This is awesome, congrats.

What really stands out is the way you engage this community, seek advice, and give back with your honest response. Part of what makes HN great.

What can we help with? I have a dev team that might be able to spare some bandwidth. If there's anything we can do, please let me know (email in the profile). No strings attached.

Thanks!

I'll drop you a line off HN.

Congratulations!

Thanks man! Your advice and support have been a big boost. Been following your suggestions about how to spend our cash so far. While it took 2-3 devs before we found someone who wouldn't whine about working with a non-programmer on a less-than-awesome codebase, we found a great guy and are getting stuff done in bits and bursts.

Congrats! I used to live in Chicago and would have loved this as a resource

The traffic growth is impressive. How did you first start getting traction? What methods did you use to promote the site early on?

A lot of that is the secret sauce. But direct e-mails to people who might be interested in your content, and a lot of them, is really the only tool that's worked.

How do you make sure that people are only posting news from Chicago?

Thus far it's been security-via-obscurity plus aggressive moderation.

How much time do you spend on moderation? Seems like it would be a lot of work. Problems with spam?

That's what interns and crowdsourcing is for. We've got a nifty "bury" feature that lets you hide stories you don't like just like on a lot of these sites.

Cool - Every major city should have one of these. Nice Job Man!

Great work, Brad!

Thanks, man!

Awesome!

Good for you!!! (Go Blackhawks!)

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