Story by guest author, Megan Weinerman.

DANIEL GOES ROGUE ALL THE TIME. He’s always taken the path less traveled by default because his personal history has taught him that you can do whatever you want and still have traditional success. His guiding principle: “Mess things up”. But he never seeks to destroy, just to change things for the better.

An example of his “Mess Things Up” theory is when in 2005, he started a wireless group that gave CTA riders a way to tell each other about service outages throughout the system. This was after he was frustrated with the CTA’s lack of clear communication with its customers. So instead of whining about it, he went in and “dive bombed” and started an outside group that could affect change. It did so well, the CTA quickly got on board.

But we’re jumping ahead, so let’s go back to the beginning….

THOUGH HE CAME FROM HUMBLE BEGINNINGS, that didn’t mean there wasn’t a good time to be had during Daniel’s childhood.

“We started out in the Northview Heights housing projects in Pittsburgh, Pennsylvania. I was the last of seven children, so my childhood was about never being first or the best. It was about being good with the hand-me-downs and never giving up. I had strong male influences in my life since I came from a family of six brothers and only one sister.”

“My father was a writer. He wrote TV and radio advertising and PR in the 1950s then got into PR for malls when that industry started growing in the late 1960s. We lived in the projects for two years then moved to another neighborhood that wasn’t much better. My father never did well in his career, while my mother was ‘steady-as-it-gets’ as a reservations supervisor at Trans World Airlines for 35 years.”

“We didn’t have much money and lived in a less-than-wonderful neighborhood— and we knew it —but our lives were still large, full, and fun. It was the 1970s and I had a lot of teenage brothers who were involved in craziness…sometimes illegal. But my parents handled it fine. They dealt with stuff as it came.”

“My brothers influenced me quite a bit because we were a big, rambling family and both of my parents worked. There wasn’t a lot of tight, parent-child interaction like I think a lot of families are used to now. I think siblings used to have a lot more affect on each other back then. My childhood was very much the Inner-City Post-Vatican II Catholic life: hanging out with a lot of nuns with guitars singing Day by Day, being an altar boy, doing First Communion and community service. Community service wasn’t something you thought about, you just did it. You cared about poor people, about helping people and about being part of the community.”

“I learned how to stay out of trouble by watching how my brothers always got into it. I did a lot of things wrong, but I also got a lot of breaks because I was the youngest and the comic relief in the family. I learned how to be smart – that meant not getting sloppy with cops, not being the one barfing when drinking at the party, and I knew to run when the cops showed up.”

“Then my mom, one of my brothers and I moved to Chicago from Pittsburgh after she got a divorce and a job transfer. It was a traumatic change at the time but ended up being the best thing in the world for me, mostly because it got me away from my alcoholic father. I developed my own taste for booze when about 13. I didn’t realize I was an alcoholic until I was about 22. Then at 33 I joined AA, which I was familiar with since my dad had been a long-time member. Don’t get me wrong, I had a lot of fun when I was a drinker, and actually most of the people in my life didn’t realize I was an alcoholic because I knew how to handle it so well. (Remember, I learned at a young age how not to be the sloppy drunk at the party.) But eventually I realized I had to create a change for myself. Now I love my sobriety and I find that the principles of the program are a great basis for both life and business: Honesty, thoroughness, and humility.”

BETWEEN LEARNING HOW TO MAKE TROUBLE WITHOUT GETTING INTO TROUBLE, getting good grades in school, partying, having a love for swearing (which we cleaned up for this article) and traveling the world with the help of free first class tickets through his mom, Daniel kept himself busy throughout different stages of his youth. Oh, and he wrote poetry. As a matter of fact, Daniel never thought of himself as an entrepreneur as much as a poet, and he’ll gladly tell you why.

“I’ve started lots of ventures—a poetry book company, a theater company, a consulting practice—but never considered those activities ‘entrepreneurial’. I just thought of them as a way to do what I wanted. Everyone I ever knew from grade school on always had something on the side. It was always about ‘Do what you want, and have it financed by your day job.’ In the entrepreneurial world, I usually hear a lot of anti-corporate sentiment. But I thrive in both cultures. I have no problem with either whatsoever.

I’m just driven to do things, to create. And I’m always looking to align my passions with my efforts, and figure out how to easily pay for them, rather than how to make money off of them. Then the money always follows because the new passion usually turns into a new job. Then I start all over again with finding a new passion.”

“And like I said, I don’t really think of myself as an entrepreneur. But I do define myself as a poet. I was always a poet and writer. I started writing when I about seven. It was just always a part of me. At my First Communion I performed On Children, a poem by Khalil Gibran, who was THE poet of the 1970s. Then later I was a poetry performer and a director. I wrote plays in the late 1980s and early 1990s. Even did some performing, too.”

“From sixth grade through high school, I was always the lector at the church, the dude that gets up and says the readings, which helped me get comfortable with performing in front of an audience. Then when I got out of college I was a full-out poet and totally into writing and performing it. I was writing plays and lived in Wicker Park in the late 1980s, which was a pretty ripe scene for theater and poetry. Things were happening like the poetry slam, which was invented by Marc Smith here in Chicago at that time. It was obvious to everybody that something good was going on right around then.”

“My poetry writing was kind of bombastic and theatrical. I always tried to make it actual literature rather than temporal bar fodder, which I think is what a lot of modern performance poetry ends up being—very hot button-y rather than literature.”

“Then in 1990, I went through a really creative writing period. I had just graduated from UIC with degrees in English and anthropology. I thought about being an ad copywriter since I had a good mind for taglines and snappy copy. But I didn’t want to do it. I thought it would ruin me as a writer and I didn’t want to be a frustrated artist. So I became a paralegal instead.”

“I got a job at a pretty big law firm. I was that creative guy that everybody liked to have around, like a mascot that made everyone proud of himself because they employed a poet. It must have been the perfect environment for me because during that time I wrote three books, all poetry and essays. I started a poetry book company so I could publish them, the first one being published in 1992. I was excited about making a real company out of it. My goal was to bring poetry into the center of American pop culture and entertainment. I even described myself as ‘The Worldwide Entertainment Juggernaut of the 21st Century’. But then I realized that I didn’t care enough about other people’s poetry, I just cared about publishing mine. So that didn’t work out too well. I consider my biggest failure in life to be not making that company work.”

“I really wanted to do it but failed, probably because I didn’t try hard enough, number one. Number two is because poetry is so fetishized and tokenized in our culture that it was hard to make it feel more accessible. People like poetry to be all about emotions and how someone feels. I think poetry is better off as art than feelings.”

“Then in 1994 I started doing poetry tours. I had an agent who booked my gigs and I’d pay him, like, five bucks out of the twenty I’d make that night, that type of thing. A couple years later he called me up and said he wanted to send me on a 10-city tour. I said ‘Alright’ and took a vacation from my paralegal job. We even had Camel cigarettes as a sponsor, which was huge. That meant I could afford to have an orchestra with a cellist that created all original music based on my poetry. It was a crazy windfall for an edgy performer like me. It was great. I ended up doing three or four national tours like that.”

“And since it was poetry, you never knew who would end up in the audience. I liked it when I would do a show with just three people in the audience. Even though I craved juggernaut status, being unpopular actually gave me an odd sense of power, like ‘You don’t know what you’re missing!’ During these tours I thought about the same things every artist deals with: ‘Am I going to be a sellout or an authentic artist? And if I live like a real artist, how am I going to have a normal life with a house and family?’ But I realized I didn’t have a conflict. I figured I was going to do things that people paid me money for and I was going to do whatever I wanted. Once again, I realized I just needed to follow my instinct of ‘Do want you want, and have it paid for by your day job.'”

THEN IN 1998, AFTER OBSESSIVELY FOLLOWING THE LAST CHICAGO BULLS CHAMPIONSHIP of the Jordan era, Daniel started working on the “Wide World Web” and never looked back.

“I got a job at a web marketing agency all because of a poster that a friend designed for one of my poetry shows. He was working for this company that needed a project manager, and my friend recommend me. I found out that I really loved the work. And the people who worked in it fascinated me. I learned that there were two domains that ruled the web world: technology and design—user interface and back-end. I loved the technologists and designers because they were cocky and liked to have their private language. They were a tight little guild and if you weren’t in their guild you were a zero. They liked to fool you into thinking that something couldn’t be done on a project because of a technical limitation but, in fact, they either didn’t want to do it or they just wanted to mess with you.”

“So that inspired me to jump in and start learning as much as I could about the technology. Around 2002, weblog technology and other simpler tools started taking off. One of the most empowering things about this technology was that it lowered the barrier of entry for people like me. What used to takes months in re-designs and a lot of dollars now could be done with a click of a button. I just really got into it and started a side business of making websites using this weblog technology, which to me was another way of ‘messing things up’ because I was taking something considered ‘elite’ at the time—making websites—and messing with it by making sites using easily accessible blog technology. But what really started to fascinate me was not the technology, but the data and content that was managed by these systems.”

DANIEL’S PASSION FOR DATA FOUND ITS HOME when he started to learn more about the open data movement, and eventually joined EveryBlock, a site that connects neighbors to what’s going on in their neighborhood, as a co-founder and “People Person”.

“In 2005 I started a project called which mapped every 311 service request, every building permit, and every restaurant inspection in Chicago, and included blogs for citizens and neighborhood groups so they could connect and share what was going on. I was inspired with this idea after seeing Adrian Holovaty launch, which was basically dots on a map showing every crime in the city. I pitched my concept for to the City of Chicago while I was a contractor for a small technology firm. They loved it and the project was funded and nearly completed, but for numerous reasons it was later shelved.”

“During this time I got to know Adrian, so when he received a grant to start EveryBlock, he asked me to join. So I became the fourth founder in June 2007 and became their ‘People Person’, someone who worked with people to provide and describe data. It was a new type of job that hadn’t existed before. I felt like working at EveryBlock gave me the chance to finish what I’d started with”

“I loved when I had to call a guy, say in San Francisco, and tell him that I wanted to get a list of all the building permits, and for him to ask me which one I wanted, to which I would respond, ‘No I want ALL of them, for every day.’ It blew people’s minds. I thought it was great, and I really dove into learning all I could about the open data movement. Lots of people at that time were starting to work on the principles of transparency and accountability within governments and companies. It was a very ‘storm-the-bastions’ time period.”

BEING PART OF THE OPEN DATA MOVEMENT can get you a free trip to the White House. Daniel can tell you how.

“I ended up at the White House because of a side project I was working on and my friend Harper Reed, the Chief Technology Officer of Obama for America. He and I became friends after working on some projects together.”

“I had found a City of Chicago website that listed every contract, vendor, and payment ever made to anybody the City ever had a contract with since 1997. It was an interface that let vendors find out the status of their contract. I was in love. I wanted to create something similar that everyone could have access to in order to see ALL the payment patterns in the City. I saw it as a great tool for transparency and minimizing corruption because people could study the patterns.”

“So I hooked up with Harper and he programmed a way to suck up all that data. Within a couple of weeks, we sucked out every single contract, payment and vendor to make our own database,, which anyone could access. It took a system that was good at answering some questions like ‘What’s the status of my payment?’ and answered a whole other set of questions around ALL of the payments and ALLof the data. Then the White House found out about it and invited us to come out.”

“Open data has now become an accepted part of any forward-thinking government. The next stage—and there is some danger in how well that stage will go—is to develop a mature market for data. That means we need more and more sophisticated services consuming the data, more legislation governing the broad use, and more developers focused on creating apps for the civic good. ”

DEVELOPING TECHNOLOGY FOR CIVIC GOOD is the focus of O’Neil’s latest ventures the first Executive Director of the Smart Chicago Collaborative, a civic organization devoted to making lives better in Chicago through technology. He joined the Collaborative, which was founded by the City of Chicago, the MacArthur Foundation, and the Chicago Community Trust, after leaving EveryBlock in 2011.

“A large part of our work revolves around infrastructure and programs that make the resources of high-speed Internet more accessible, useful, and beneficial to low-income people and neighborhoods. We also work on what happens once you’re connected, like how people can connect with city government and each other. One project we’re funding is the City’s Code for America project, which will allow the City to comply with the Open 311 standard and open up a host of opportunities for civic application.”

In other words, Daniel will be “messing things up” again for the greater good of Chicago’s civilians, and still getting paid for doing what he wants to do.