Scott Kleinberg is the social media director and web editor of  RedEye, the Chicago Tribune’s commuter tabloid. He manages @RedEyeChicago, which has more than 30,000 followers and is used to gather news, tips and photos for the newspaper. He also co-created #RedEyeRoyalty, a passionate group of social media ambassadors and has experimented with new ways of connecting with readers.

We recently spoke with Scott about how he’s created a community around @RedEyeChicago and how businesses can use Twitter effectively.

Tell us how you originally started the RedEye twitter account. It’s a great story.

It is a great story, isn’t it? It makes me happy. I noticed Twitter really starting to take off in 2008 and I knew RedEye had to be a part of that conversation. I wasn’t officially doing social media then – no one really knew what social media was – but I knew RedEye needed a voice. RedEye has always done such an amazing job talking to readers and this just seemed like a natural extension.

When I pitched the idea of creating a RedEye Twitter account, one of my bosses responded “no, thanks. I don’t think we’re interested in that.” As someone who always respects authority but has a tough time taking no for an answer, I went home and created @redeyechicago – and I made a deal with myself. Self, I said, we’re not going to tell anyone about this until we reach 1,000 followers. That happened two weeks later. The rest as they say is history.

This whole thing reinforced a very valuable lesson: There is no such thing as a terrible idea, so don’t be afraid to try. Certain things in social media will be a slam dunk and others will flop, but you can’t succeed without the occasional mistake.

Today @RedEyeChicago has more than 28,000 followers. How did you grow its following?

29,000! Remember those mistakes I just mentioned? It was a lot of trial and error. It certainly helps that so many people in Chicago know what RedEye is, but one of the things I did early on was buck the trend. Many media outlets choose not to identify the person behind the tweets. I started along that route thanks to advice I got from friends and colleagues – including a certain gentleman in this building that I’d never name (he wears a paper hat).

But it was a @redeyechicago Twitter follower that changed my entire philosophy. I’ll never forget the exchange. He tweeted me and then direct messaged me to thank me for the great content. And then he asked my name. Following what I had learned about Twitter and social media and brands to date, I told him he could call me Red because I was RedEye. He said it wasn’t good enough and I replied that I had to follow “the rules.”

But I didn’t know what the rules were, and, as you saw earlier, I’m not afraid of breaking them. He thanked me again but said he could no longer follow me because it’s like talking to someone without a face. He then went on to say that he thought RedEye was so personal and what I was doing didn’t feel personal. It took me 10 seconds to send my next DM, which started with my name. I think I even told him my favorite cereal – it felt so good to be me. He was so right, and I’ve never forgotten the exchange.

To this day, people say they can’t believe I “outted myself.” I didn’t out myself – I made what we’re doing a personal experience. It is social media, right? Piece of advice? If you use social media or plan to use it, you have to be social. It sounds like a no-brainer, but so many people approach it the wrong way.

How do you decide what to tweet about? You are representing an entire newspaper after all.

I’m like a chef creating something without a cookbook. First and foremost, I think about the ingredients and how to mix them. What I never want to be is a link machine that only talks about what’s in RedEye. That makes me feel like a used car salesman (and I apologize to every used car salesman that I just offended).

So normally, I tweet once every 30 minutes. I tweet a RedEye link no more than once an hour. On the half hours, I tweet the things happening in the world that I think will interest our readers based on what we know about our print readership and online readership. In many cases I’m guessing, but the amount of retweets I get tells me when I’m doing something right.

Oh, and at 8:30 every weekday morning, I do the Tweather – which is pretty well known in Chicago. It always starts off “Good morning, Chicago … Tweather in a word is XXXXX.” Sometimes, I include little weather icons – my favorite is the little snowman. The rules are simple: The tweather in a word always has to be one word and it has to be something fun. So when it snows, you might see “snowballs.” And when it’s 100 degrees you might see “crispy.”

And here’s something you might not realize even if you follow @redeyechicago – the 10 am spot is always reserved for a video. I think a viral or fun video is needed every morning to put a smile on people’s faces. You might have to convince your bosses that it’s beneficial to talk about things other than what’s in your paper or on your site, but trust me when I say it’s worth it. I think of @redeyechicago as a destination. You read RedEye on the bus or train in the morning, but what happens when you’re done with what’s in the paper?

And then there are tweets, like this one from @amazemeack, that make it all worth while: “@redeyechicago You are the reason I come on to Twitter. Thanks for being my favorite thing I follow.” I felt my eyes getting a little moist after reading that 🙂

At the same time, you’re also @ScottKleinberg and many people know you’re tweeting for RedEye. How do you separate @ScottKleinberg from @RedEyeChicago?

First off, I make sure I’m transparent in both profiles. People who follow @redeyechicago know I’m @scottkleinberg and people who follow @scottkleinberg know I’m “the voice of @redeyechicago.” My personal account also includes links that I think are interesting, but maybe not the same kind that would be interesting to RedEye readers. So there’s more of a social media/80s music/Chick-fil-A/iPhone vibe. Plus, @scottkleinberg holds more conversations with other Twitter users – more so than on @redeyechicago.

You’ll see some @ replies on @redeyechicago, but I subscribe to the philosophy that if it requires 2 or more tweets to talk to a follower, the conversation should be moved to a direct message. Holding a private conversation in public with 29,000 followers is like screaming from the upper deck to the club boxes at Wrigley. You might see more than two tweets on @scottkleinberg, but I try my best to ensure you won’t be bored.

You manage several Twitter accounts. Have you ever tweeted with the wrong account? Or worse, sent a public DM?

I’m afraid to answer this question because I know it will happen. Yes and no. I’ve never personally done it by hitting the wrong button. But once, while testing out SCVNGR, I guess I logged in as @redeyechicago instead of @scottkleinberg. And when I checked into an Italian restaurant in Evanston, it tweeted on @redeyechicago that I was “having a great anniversary dinner with Kelly.” A few people tweeted “who’s Kelly?” (my wife) and “don’t forget the garlic bread” (oh, I didn’t!) but nothing horrible. And no, all of my deep dark secrets are still deep and dark – I’ve never sent a public DM. Honestly, my DMs aren’t all that exciting anyway.

What’s the funniest tweet you’ve ever seen? The saddest? The strangest?

Funniest? There are lots, but this is one I love: “This is the way Facebook ends. Not with a bang, but with a friend request from your own mother.” Thinking about that, my mom isn’t on Facebook and I’m still undecided as to whether or not I’d follow her. Have you given that some thought?

I remember the saddest one to this day. It was last year and it was from someone who just got back from his father’s funeral. He said something to the effect of being more alone than usual now that his dad was gone and all he could think of doing was mourning via Twitter. It brought a tear to my eye, but sometimes your followers can actually be a great support system so maybe he was onto something.

As for strangest, for me that’s still the day the plane crash-landed in the Hudson River. Like such offline gems as “I cannot tell a lie” and “that’s one small step, …” I think the tweet from @jkrums “There’s a plane in the Hudson. I’m on the ferry going to pick up the people. Crazy.” is going to go down in history as incredibly awesome yet strange.

What’s your typical day like? Are you always tweeting? How do you disconnect?

I tweet a lot, but I wouldn’t say I’m always tweeting. Sometimes, I actually am mad that I don’t tweet enough on @scottkleinberg and on my iPhone blog account at @iptib. Luckily, my wife is the official tweeter for our Puggle. Seriously. @MacThePuggle is on Twitter. You should follow her – she’s the cutest dog in the world (talk about your shameless plugs, right?)

As far as disconnecting? I have a few ways. First off, when the weather isn’t brutal, I really like walking home from work. It takes me about 25 minutes. Then, I enjoy having dinner with my wife and dog and watching all the shows I missed on the DVR. Oh, and then there’s Angry Birds – I think I get a lot of frustration out through those birds.

Where do you see the revenue in Twitter? Can businesses expect to make money from Twitter?

Even after all this time, Twitter is still an experiment when it comes to making money. To me, the best part of Twitter is being able to know who is following you and why. And while there isn’t much in the way of analytics from Twitter, you can usually tell who your “regulars” are. Knowing your community is really important.

I think businesses need to resist the urge to think that paid or sponsored tweets are going to go over well with audiences. My takeaway is you use Twitter and other social media tools to figure out who the audience is and then you go after the audience to make money. It would be nice, though, if you could push a magic button and make Twitter translate into profit.

Speaking of businesses, what advice do you have for businesses that want to start tweeting?

I’m so glad you asked me that question. First things first: Engage. I can’t stress how important engagement is. It drives me crazy when I see people “interact” by posing questions but never getting back in the conversation. I see businesses on Twitter that have so much potential just because of who/what they are, but they don’t take the time to talk to their followers.You might think you don’t have time, but you do. You’ll get out of Twitter what you put into it.

Besides engagement, know your audience. If you see one or ten people that are constantly retweeting your message, follow back and reach out and thank them. You’d be amazed at how a quick thank you – either as an @reply or as a direct message – resonates with your audience.

And, on that note, NEVER set up automated direct messages. They make me mad. Automated direct messages like “we’re like two peas in a pod – let’s talk soon!” is a slap in the face and goes against everything social media is supposed to be – and that’s social. My last piece of advice? If you aren’t sure, ask. Ask me, even. I’m happy to help.

As we speak, Chicago is hunkering down for a blizzard. How are you using social media to gather news and reaction about the storm?

Where to start? Our social media fans and followers are amazing. First, we launched a callout to give the blizzard an official name – you know, like President Obama called the December storm that hit the East Coast “Snowpocalypse.” We got 116 entries – everything from #Snowprah to #Blizznasty. The idea was to create a name we could append as a hashtag to all storm-related tweets.

The winning hashtag boosted us to the top of the Twitter trending topics for Chicago for an entire day! After 1,188 votes, #SNOMG! won by 2 votes over #SnowtoriousBIG. Today, everyone is using it – in Chicago and beyond. FEMA even picked up on it. We also put out a call asking people to guess how much snow will fall in 3 key Chicago spots: O’Hare, Midway and the lakefront at North Avenue Beach. That and we’re putting out the call for the mother of all photo galleries – everything from features to traffic to dibs.

All told, in 24 hours leading up to the storm (the snow is just starting), we’ve received more than 150 comments on Facebook, almost 100 likes, more RTs than I can count, more than 7,000 page views, a piece on WGN-TV evening news, countless mentions on tumblr and hundreds of new Twitter followers. I can’t wait to see what happens during the rest of the storm!

If you could have one person follow you personally on Twitter, who would it be?

Great question! Well, let’s see … I already have my wife, my dog and Rick Bayless following. So I’m happy in general. But my ultimate Twitter follower – on @redeyechicago, @scottkleinberg or both – is Conan O’Brien. I’ve tweeted him with ideas but he never responds. I know, I know … He’s busy doing that show and stuff. But I’ve had my share of celebrity love.

Alyssa Milano tweeted me about my baseball wedding, Greg Grunberg has tweeted and retweeted me on several of my accounts and Mc Hammer tweeted me a Twitter movie review that we actually printed in RedEye. But I’m still holding out for Coco. Or Steve Jobs.

Every Wednesday, we’ll post an interview with a leading social media icon. Recent interviews include @JayRosen_NYU and the Huffington Post’s @Ckanal. Have someone to suggest? Let us know via twitter @435digital.