Becoming More Efficient At Making Stuff People Want – With Brad Flora

by Tim Jahn on November 12, 2010

Upon first glance, Brad Flora’s local Chicago news site appears to be running on the traditional advertising model.  But a closer look reveals the ads aren’t just regular banner ads; they’re real time ads, created by Brad himself.

I sat down with Brad to learn how he bootstrapped WindyCitizen into a profitable business and has now spun off his real time advertising idea into a new business called NowSpots.


Brad Flora:
My name is Brad Flora and I’m the founder of Windy and also now the founder of

Tim Jahn:
So what’s Windy Citizen for people that don’t know?

Brad Flora:
Sure, Windy Citizen is a website that makes it really easy for people in Chicago to share, and find cool local news.

Tim Jahn:
And why did you create Windy Citizen?

Brad Flora:
I started the Citizen two and a half years ago because the number of websites covering Chicago is growing quickly. I think at the time there were maybe 100 or so and now there’s more than 300. And it’s hard to find all the best stuff in one place. So Windy Citizen is like a real time 24/7 cheat sheet of stuff that you should read that’s local.

Tim Jahn:
When you actually had the idea and you said, “Okay, I’m going to create Windy Citizen”, how did you go about doing it?

Brad Flora:
Yeah, so when I was in grad school at Northwestern I had kind of two ideas that I thought would be fun that I hadn’t seen anyone try yet. One of them was to do like a local Huffington Post and then the other was to do a local Digg or Reddit kind of site. And when I got out of graduate school, this would have been in the spring of 2008. The Huffington Post idea was the one that seemed within reach.

I had contact with a lot of underemployed writers and so we kind of set the site up, we had 20 writers from day one and people just started going writing daily a couple of times a week, and about food, and technology, and politics, and the city. And so we did that for about eight months. The problem with that though was that the content was very inconsistent and maybe once a week, once every two weeks we’d have something that was actually really good that we could show off to the rest of the internet.
But the rest of the time, we had pieces that were very personal and weren’t all that interesting. And we had a hard time kind of growing the number of writers that we had and making that scale. So after about eight months of that, I shut that down. We still run a lot of those blogs but they’re kind of more on the side. So I think right now we have nine bloggers that write on a regular basis for the Citizen.

And then we fired up the link aggregator where we let people post local links, links to videos and soon photos. And just started posting stuff everyday and inviting people to join me over there. And eventually its grown to where we have I don’t know maybe a few hundred people that post several times a week and then a few dozen who post everyday. And together they seem to do a really good job of finding all the interesting stuff that’s out there and giving us a really cool front page.

Tim Jahn:
What did you do when the original idea didn’t work after eight months and then you said, “Oh crap, I have to rethink this.” What — I mean did you go out and have a drink?

Brad Flora:
Yeah. I — like I said, this has been a very humbling experience. There’s no super insight or genius, or anything going on behind the scenes with Windy Citizen. Its just I refuse to fail. And so if I try something and it doesn’t work, I try to admit that as quickly as possible so that we make a clean break and then try something else.

So that first year was pretty challenging. It was just me by myself. Everything that I was trying, I wasn’t that excited about and I was having trouble finding readers that were excited about it. And so I have a lot of experience now with making stuff people don’t want. And hopefully I think that helps you get better and more efficient at making stuff that people do want.

Tim Jahn:
And speaking of making stuff that people do want, you developed this ad system in Windy Citizen that you’ve been allowed by money to spin off a new business. Do you want to tell me about that?

Brad Flora:
Yeah. So, it’s funny how you work on one thing and you might be running off in one direction but in so doing that you might learn something that can take you in another direction. And so with Windy Citizen, we’ve always been focused on the content. If we want to have the best front page in Chicago. We want to have like ten links that will amaze, delight, surprise, and astound you on our front page every morning. And we do a pretty good job of that most weekdays.

But, eventually we had to figure out how to make money. And it was pretty apparent to me that with a site that had our size audience which I think the most we’ve ever done in a month is probably, it would be 250, 280,000 uniques. But on average, we’re doing about 100,000 unqiues a month on the site. And so that’s still pretty small. Like that’s just enough to qualify you for some of really crummy ad networks out there. And so if we were going to make really money that was going to support real humans working on this, I had to find a new way to approach online advertising.

And so we came up with this — I started thinking about banner ads which is what people typically sell and the fact that the pricings always down, nobody likes clicking on banner ads, nobody likes selling banner ads, nobody likes buying banner ads. So I had to think of well, if I had the same amount of space, what could I put there that someone might actually want to buy and pay for? So I came up with this idea of an ad that gives more value to the advertiser in the form of control. So if you’re an advertiser and you buy a banner ad on a website, maybe you change it once a month or you can change it once a week.

What if you had complete control over that spot and you could change it as many times as you want, whenever you want, however you want, from whatever device you like to use? And so that’s where we came up with this idea of real time ads where we pipe in the advertisers latest twitter update, or their latest Facebook post, or their latest headline from their blog directly into the ad spot. And anytime they want to change what’s in the ad, they just update it.

So we started doing those and we started doing that about a year ago. And since then we’ve sold I don’t know, probably about 20 of those. We sell them for a month at a time as sponsorships and the pricing starts at about $1,500.00 a month.

Tim Jahn:
What excites you most about this new idea?

Brad Flora:
Well, what excites me most is that we’re solving a really tangible problem. So that’s cool. With the Citizen, the problem that we’re solving is you’re bored at work. And that’s a great problem to solve but there’s a lot of people working on that problem. And so it’s a very competitive space. Getting headlines is, and getting readers, and people to refer to you, its always tough.

With NowSpots, we’re solving a problem and we’re solving a problem that is I would say zero orders removed from the making of money. So the closer you can be to the actual point of payment, the better. And so with NowSpots, maybe we’re one point removed because what we’re doing is we’re selling these ads white label to other publishers who then sell them onto their advertisers. So yeah, we’re a step away.

Whereas Windy Citizen’s probably like five or six steps away from making money from that point of sale. So that’s really cool to be in, working on something that’s directly tied to the making of revenue, and also something that in some way kind of sells itself.

Tim Jahn:
So with the Windy Citizen among other things I’m sure we’re challenging you, started it out with kind of the wrong idea in a sense you figured out the right idea, it worked. What about NowSpots? What have been the challenges so far in — and I know it’s so young.

Brad Flora:
Yeah, yeah. I mean, NowSpots it’s a different experience. So Windy Citizen bootstrapped early on, I sent, I’m a Princeton Alum and there’s and email list for people who are like Princeton entrepreneur alumni. And early on when I starting Windy Citizen, I send an email out to everybody and said, “I’m starting my first business, I have no clue what I’m doing. I need to find like a technical cofounder who knows how to program because I don’t really know how to do that stuff.”

And I heard back from tons of people, some of them were developers who wanted to work with me and so forth. But one guy who is like an investor in the like Green Energy space, wrote me and said, “You don’t know anything. You are a complete idiot and you have to acknowledge that in order for you to learn anything and be successful.” He said, “I’m not a programmer, I can’t help you with that. But I will call you and have a 30 minute conversation with you every Sunday evening fro the next year if you take my advice only and listen to no one else.”

So I kind of weighed my options and that was the best deal anyone gave me out of the email that I sent. So I said, “Sure, I’ll do it. What do I do?” And he said, “Do it alone, work with no one, collaborate with no one. You have to learn every piece of this business in order for you to learn how to maybe someday either turn it into a really good business, or start a new business where now you have all the skills and the experience, and have seen every side of building and delivering a product.” And so that was a hard teaching. And so that first year he said, “It’s going to be really painful and you’re going to be really lonely, and you’re probably not going to be very successful.

But no matter what you do in business the rest of your life, it will never be this bad, and so you will always have this time to look back on and know that you are tougher than whatever you are facing.” So that’s kind of what we did. And so every week I’d talk to him for a little bit and he didn’t really want to talk about the company or Windy Citizen. He just wanted to know like are you exercising? Did you go on a date this week?

Tim Jahn:
This guys like a Mr. Miyagi.

Brad Flora:
Yeah. Yeah, very much so. And so, and he’s only a couple years older than me. I mean, he’s been a great friend to me. And so — I’ve only met the guy once now in three years. But we would talk a lot on the phone; talk a lot online, a lot by email.

And so with Windy Citizen, that was very much the experience of teaching myself basic programming skills, doing the marketing myself, doing the outreach myself, finding the content myself, rather than trying to find a partner and having it be something that I own 100% of until I got to the point where I felt good bringing in someone to work on the advertising with me after I’d already defined the product. With NowSpots, its completely different and its really fun because we’ve got funding, we’re working on a space with a large opportunity. If you take the top 20 newspaper sites, they do accumulative of about three billion page views a month. So that’s a lot of inventory that we can possibly fill with these ads that we’re building.

So it’s a much larger opportunity and now, I have this perspective on building a product and selling it on the internet which has enabled me to get top quality co-founders. So it’s a guy, his name is Jason Rexilius; he’s worked on a ton of startups before. And so he’s my CTO, and he’s working on the product. We’ve got tons of publishers who’ve worked with me Windy Citizen stuff before and have always been intrigued by what I’ve been doing. And now I’m able to come to them and say, “Look, now I’m working on something that will put money in your pocket.”

And so I’m able to work my rolodex that way, defined our initial customers. And so it’s been night and day. A totally different experience but without having the kind of honestly like I wont say like gone through the Windy Citizen stuff would probably be more accurate. I wouldn’t have the confidence and I think the poise that I have to work on this NowSpots stuff. And to take a meeting with one of the top newspapers in the country and know without a doubt that I’ve got a great product, it’s going to do great things for them, and they would be fools not listen to my pitch.

Tim Jahn:
Where do you get that kind of confidence? Is in the product or is in your experience?

Brad Flora:
I don’t know. I mean, I’m kind of a glutton for punishment so I really do think — this is going to sound absurd, but like suffering. Like until you failed so many times that you know every possible point of failure and can steer away from them, I don’t think, I think that’s where a lot of the confidence in the product comes from is knowing like here’s everything that can go wrong.

And now that I’ve lived through those scenarios or at least pictured them mentally, I can steer clear of them and make sure that they don’t happen. Or know that if they do happen, I’ve been there before, be able to figure it out. If a developer bails, been there. If you know the code comes in and it’s terrible, I’ve been there.

If you have some kind of like a deeply hidden architectural fault in your product, I’ve been there before. So pretty much its like clown school over at Windy Citizen sometimes. But that’s been kind of by design and it’s been really helpful in giving me a lot of great tangible experience.

Tim Jahn:
So you’ve built one successful business in Windy Citizen and now you’re working on your second business with NowSpots. What’s one piece of advice you’d have for someone who’s still working on their first successful business?

Brad Flora:
Yeah, you know it’s tough. Like you really got to look at where you’re at in your life and how you want to approach doing something like this. With the Citizen, I’m quick to qualify that like the advertising money that we bring in supports one person on a very sensible but livable salary plus commissions for an ad sales guy.

So I think by the definition of success for a small bootstrapped internet business, yes, I do think it is one. But we’re not minting money or anything over here.

But I think it’s important for people to figure out where are you at in your life and what does that let you do? So in my case, I was 26, I was single, I was in pretty good health, and my family lives close by like two hours away from here so I could go see them if I needed human contact. And so I was able to take like the hard road of just walking into a wall until I figured out how to like shift through the wall. But maybe that’s not for everybody. So I think no matter what you do though, you’re success will only be a function of your friends.

And so if you look around at the people that you hang out with and none of those people can help you be successful, then you have to make new friends. And a lot of people don’t like doing that. I don’t really look at it as networking. Like it’s legitimately about making friends. And so if your friends aren’t the kind of people who can solve problems in your business, then you need to go out there and find the people who can, and then find the subset of those people who you enjoy their company and then make friends with those people. So 99% of the people I talk to on a daily basis, I’d never met before in the last two and a half years.

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