Two years after graduating from the University of Kansas, Todd was working in real estate—the career he thought he wanted in college—but he wasn’t quite happy.

Todd and his soon-to-be partner Louis Amoroso, then an associate at Andersen Consulting, were hanging out a lot, and Louis happened to mention one night that a friend of his had joined a wine-of-the-month club with 20,000 members. Could the same thing be done with beer? They decided to find out.

“It was the perfect time. The draft brewing industry was really starting to evolve. We said, ‘Why don’t we try this with beer?,’ not knowing anything about the marketing business or anything about the alcoholic beverage business and how complicated it was.”

Todd and Louis dubbed their new start-up Beer Across America. The idea was simple: Each month they’d send their customers two six-packs from different microbreweries.

“WE POOLED TOGETHER OUR LIFE SAVINGS, WHICH AT THE TIME WAS $2,000 OR $3,000. We went out and got a liquor license and told the city of Barrington what we were doing. I was living in the city at the time, so it seemed like a logical place to start the business off. We were working like mad men. We both had day jobs, so we would both come at night and work until midnight.”

“We started off as a beer club and took out some ads in Chicago Magazine. It was great for cash-strapped start-up entrepreneurs because we were getting all this money up front. We were able to grow the business in three years to about $22 or $23 million in top-line revenue. We thought we were the kings of the world. It was crazy. We went from a 1,000-square-foot warehouse to 5,000, and 10,000 to 80,000.”

Beer Across America was the first of several new ventures for Todd, and he knew from a young age that he liked working hard and making money. The high energy and entrepreneurial drive that inspired him to start his first company at 24 became apparent a decade and a half earlier when he was growing up in his hometown of Barrington, Illinois.

“I had twelve to fifteen different lawns I was cutting when I was ten years old. My business partner, whom I’ve known forever, lived three doors down from me, so the two of us kind of did it together, and then I did it on my own.”

Not one to sit still, Todd kept working through high school. But growing up wasn’t all hard work. Barrington was still rural for horseback riding and snowmobiling, and during high school, he’d go waterskiing down the Fox River before class.

“I was in between a troublemaker and a good kid. I was always having fun, probably a little too much fun, and at the same time I was senior class president. I was on the football team, the basketball team, and having a great time. I had lots of friends and really made the most out of high school.”

“I’LL NEVER FORGET THIS, I HEAR OVER THE SCHOOL’S PA SYSTEM: ‘TODD HOLMES COME TO DR. DEYOUNG’S OFFICE.’ I was like, ‘Oh my God, what did I do now?’ I go to his office, and he sits me down and says, ’Todd, you’ve done a lot here.’ He looks at me and says, ‘I want to make sure that this isn’t your be-all-end-all existence.’ He thought I fell into one of these categories, that high school is as good as it’s going to get for me. I just started laughing and said, ‘Are you kidding me?’”

The next step was college. Not wanting to stick around Barrington indefinitely, Todd went down to the University of Kansas and tried out for their football team.

“I went in as a walk-on, and they were recruiting me and some other guys from my high school. When I got down there, I just fell in love with the school—I just didn’t fall in love with football.  I was like ‘I gotta get out of here,’ so I joined a fraternity.”

He continued to hold down jobs through college and interned at his father’s real estate company. Although his post-collegiate real estate career was short-lived, starting Beer Across America kept him close to his entrepreneurial roots.

The next big opportunity came at Christmas 1993, when Todd got a call from an investment banking group that was looking to take a public brewery private. They introduced Todd and Louis to John Hall, founder of the Goose Island Brewpub on Clybourn, who wanted to buy a facility to make and bottle his beers.

“John is my dad’s age, a super nice guy. We started working together because we thought that if we had a big enough facility we could contract brew the beer. If it was in Chicago, we wouldn’t have to truck the beer across the country, and we could help offset some of the fixed costs we had in terms of building a much bigger brewery.”

“It was really a nice tradeoff. Myself; my partner, Louis; and then our chief operations officer, Bob Beaubien, ended up building it out. We owned half the equity in Goose Island, and John and his partners owned the other half.”

But investing in a Goose Island wasn’t the only change brewing at Beer Across America.

“Over the course of the first couple of years, we ended up developing wine clubs, which eventually became our biggest seller. Because we could charge more for the wine, we had better margins, and we were going after customers who were sticking around. When we looked back on it after a couple of years, we took our lifetime value from people sticking around for seven months to twenty-two or twenty-three months.”

“I WAS DOING DOUBLE DUTY. My expertise was running marketing on both sides of the equation. I was doing all the customer-acquisition stuff and everything from Beer Across America and International Wine Cellars, and I was helping to develop the brand for Goose Island as it relates to retail trade.”

“I stayed really actively involved with Goose Island for about three or four years, and I was on the board until we sold it to Budweiser in 2011. I really got into the weeds in terms of how we ended up growing that business.”

By the late nineties, the business had grown to the point where they could hire a sales and marketing team, freeing Todd to chase the next big thing. Dot-coms were booming, and online retailers were offering more selection to their customers than a traditional brick-and-mortar store or a drink-of-the-month operation. Todd wanted to get in on the action.

“We created the world’s largest liquor store. It was called Drinks.com, and we went out and raised $22.5 million. It was crazy. The liquor business is so daunting because you have different products that are available for sale in a bunch of different markets. We weren’t just selling one product; we were selling everything.”

“We were becoming friends with the distributors because we were buying products directly from them. You want to talk about bad margins, the margins went from okay to really crappy. So we looked at how this business was going to grow and it is going to be an advertising model. We are going to get money from Budweiser and Smirnoff and Absolut and you name it, and they are going to advertise on our website in order to sell their products direct to our consumers.”

“It was a dot-com model to the point where we had an SAP backend. It was such a strange period of time. We were probably processing 150 to 200 orders a day. What the heck do we need a SAP backend to run these kinds of numbers? All our venture capitalists were Harvard grads telling us this is what we need to do, and I’m thinking to myself, ‘I’m thirty-one. I’ve already done this. We’ve already processed a lot more than this on systems that we built. You don’t need to spend this kind of money. Let’s figure out how to grow into it.’ … And long story short, we blew through all the money.”

BY LATE 2001, WITH NO MORE CASH TO KEEP DRINKS.COM AFLOAT, IT WAS TIME TO START SOMETHING NEW. The beer and wine clubs were still going strong, but Todd and Louis couldn’t grow that business without bringing in more capital. Todd decided to go off on his own and started Liquidus with Chris Carlton.

“How I got to Liquidus was myself and my partner who worked for me at Drinks.com were going on a lot of sales calls to huge ad agencies. I was like, ‘Oh my God, I can do such a better job than these people.’”

“I thought we would be the booze kings of the Internet.  Our first client was Heineken. We built micro-sites for these guys and different types of online marketing programs.  We got clients right out of the gate. I would sell it, he built it, and we started bringing on more people.”

Fast forward to 2004. Comcast called looking to build a classified advertising business using video on demand. Todd’s company won the project, but it quickly evolved into something much bigger.

“Comcast quickly realized that everything from developing the technology to on-ramping the clients to the maintenance and support of this product were all things that needed to be resourced over to us. They couldn’t internalize a lot of the things we were doing so we started building a team around it, and it grew really rapidly in 2006, 2007. It took us really through 2005 to develop all the different portals and in verticals. It was a lot of work. We went out and got some outside investment to help the business grow.”

“Internally, we built this product, and externally, within Comcast, they are having a hard time selling it. The Comcast sales force is great, but they weren’t necessarily great at selling this product. It’s not like selling a thirty-second spot. It becomes a very, very different type of offering, and one that local sales teams at the time were not necessarily really equipped to sell. Comcast came back to us and said, ‘Would you guys be interested in starting to sell this stuff on more of a national basis?’ So, we worked very closely with them to help grow out… We built the technology and we owned it.”

“I started going out on a lot of sales calls with our local teams and the first words, out of a lot of the car dealers’ mouths were, ‘I kind of like the Video on Demand (for TV) piece, but what I really need is video for my website.’ So, we started building out that product, , and we ended up building out a product that became better, cheaper, and faster than anything that was available.”

“IN AT LEAST THE AUTOMOTIVE SPACE, OUR VIDEOING PRODUCT IS REALLY THE 800-POUND GORILLA IN TERMS OF VIDEO PRODUCTION. Then we said, ‘God, could do this with individual videos so when you click to see a video of a car on Cars.com it is all powered by us? All the General Motors Certified stuff like that. And what if we took and compiled all of these pieces of inventory into a rich-media banner?’ So, we created a product called BannerLink and started selling it to other re-sellers, like Comcast, ABC, CBS, stuff like that. It really kind of expanded the way we went to market. It wasn’t until the late 2000s, like 2009, that we are really able to do a good job of taking our products, productizing them, pricing them out into the marketplace, and then getting them into the sales force with the right information, the right sales sheets, and everything else.”

Although beer and food have been an undercurrent of his work, Todd sees himself as more of a marketing and technology guy. He and Louis sold their beer and wine clubs in 2006 to a UK-based company called Direct Wines, but recently Todd invested in an organic farm in Wisconsin. Still, having one foot in technology and the other in the food and beverage industry can reap rewards of its own.

“I entertain a lot of people for Liquidus, and we got great season Cubs tickets. I’ll take people up to the Goose Island Brewpub before going to the game. It’s interesting how few people really want to talk about technology when they really want to talk about the brewery. For us, it has been a great thing to leverage. It has been really cool and something I will look back on and my kids will look back on, and they will think, ‘Oh my God, my dad was part of that.’”

A self-described ten-year guy, Todd’s career has been marked by a series of transitions from one business to the next, but leaving Chicago isn’t part of his plans.

“WE ARE IN CHICAGO FOR TWO REASONS—THE PEOPLE AND THE CUBS. Wrigley on Friday afternoon with the sun shining down, to me, is enough reason to stay in Chicago for the rest of my life and die here.”

“I love the people. I love the energy. I travel all the time: I’m in New York, I’m in San Francisco, I’m in LA. You just meet people in Chicago, and granted, there are scumbags here, too, but you get what you pay for and you get guys who work hard.”

“Chicago is unbelievably prideful for me. It’s the greatest city in the world. It’s truly the most American of all cities. I think to be able to make it here and give back to the community and be involved in charities here is really prideful for me.”

“I’m on the board of directors of the Starlight Foundation, and I’m working towards getting on some more boards where I can end up giving back. I think it’s important for anyone who has been successful in business to do that. It’s good and it’s good for business. I think Chicago has a lot of people who have made a lot of money here and who I think are doing a really good job of giving back to the community in a variety of ways.”

Photo by Erika Dufour Photography

“I WOKE UP ONE MORNING AND I HAD THIS LUMP IN MY LIP. I’m sort of a hypochondriac so I was convinced I was dying. I searched the web and everything said, ‘Oh, you have oral cancer and you’re going to die.’ It kept getting bigger so I went to the doctor and was told that it was just a mucous retention cyst, which is when the salivary gland gets clogged, turns into a cyst, gets bigger and you have to get it removed. He took it out with a little oral surgery, piece of cake.”

“When I searched the Internet, everything still pointed to oral cancer.’ Then I wrote a post on my blog about if you got a lump in your mouth it might be a mucocele. Everything that was describing mucocele on the web was using words that nobody would ever use to search for those symptoms. That blog post became very popular and still is: it gets about 30,000 hits a month. I had 200 and some comments so I made a forum called LumpInMouth.com. I got all this traffic. I’d look at my analytics and thought, ‘God, wow, where is all this traffic coming from?’ I’d try to figure out how to make it better. I wanted to build a community and get people to work and interact with the forum in a better way.”

“At that time I was living in San Francisco. I remember I was at some bar hanging with friends on a Saturday night. Then Kevin Rose, the founder of Digg.com who sold it for millions, walked in with his posse. I thought to myself: I want to go home and work on that forum. I need to work on my stuff. Why am I hanging out at this bar killing time when I could be finding my happiness?”

FINDING HIS HAPPINESS is how David Kadavy has created his entrepreneurial path. It probably stems from his curiosity for the world around him, which can border on obsession at times, like when it has to do with a lump in the mouth. He used that love of exploration when he authored his seminal book, Design For Hackers, in which he explained principles of design for the coder set. When it launched in the fall of 2011, it immediately ranked at #18 on Amazon’s Best Seller List.

It was evident that others had a thirst for what he knew about design, lumps in the mouth, and whatever else David was eager to explore and share.

That curiosity ride started when he was a child. As David puts it, ‘‘My mom told me I was always good at entertaining myself. I’ve always been curious and always enjoyed that ride of where my curiosity took me.” And that curiosity has sometimes been different than those around him, especially growing up in Omaha Nebraska where the mindset was more about going to school, getting married, buying a house and staying with the same job for an entire career.  As David put it, “In Omaha it’s all about the job. That’s everything.”

“I grew up in suburban Omaha surrounded by K-Marts, McDonald’s and gas stations. Our version of an adventure when I was a kid was riding our bikes across dangerous intersections to go to the strip mall and buy a soda. I didn’t know any different, but it didn’t seem right.”

“Then for college I went to Iowa State for graphic design. I also did a semester in Rome studying typography. I graduated in 2002 and got my first job starting the graphics department at an architecture firm in Omaha. Initially they just wanted to show clients graphic work of what a building was going to look like, but I ended up working on all sorts of projects. It was ridiculously stressful, crazy hours and for one reason or another we never hired anyone else, not even an intern. I was doing the one-man show, nobody was really managing my time, and I could be interrupted at any moment and asked to scan somebody’s picture of their grandson or fix a printer jam. I was expected to do things like that while I was coding or dealing with clients, and I didn’t get much guidance on how to scale things. I felt a sense of obligation to do a really good job but it stressed me out to the point where my hand seized up. I mouse with my left hand now because my hand got repetitive stress injury.”

“I also just didn’t understand the motivations of anybody around me. They had different priorities. They would ask me when I going to get married and buy a house. I heard over and over again about how buying a house was the best investment one could make. It didn’t make sense to me. I was 23 years old and I just saw the idea of buying a house as something that would limit my mobility.”

“At that time I was also very active in the graphic design and architecture community, the AIA. We had organized a tour of architects’ homes and I designed the brochure using great letterpress printing and great paper. It was my first big print job and I won a massive award for it from Communication Arts Magazine. Being in Communication Arts was supposed to be the greatest thing you could ever accomplish in the design world. That’s what you’d strive for in your career and it happened for me very early. But I didn’t find it nearly as gratifying as I thought I would. That caused me to re-evaluate things.”

WHILE DAVID WAS BUSY RE-EVAULATING THINGS, HE WAS ALSO SAVING EVERY PENNY HE MADE.  He would eat dollar meals for lunch every day and shovel the rest of his money into a stock portfolio so he could someday not worry about risk, having a job, or how he was going to afford to leave Omaha.

“I bought Apple and Google. They seemed like such no-brainers. I remember reading about analysts questioning whether Apple could continue to innovate. I didn’t think these critics understood how creativity worked. If somebody knows how to make something innovative, they know the process and they can do it over and over again. It just means combining certain factors together. With Google, the analysts thought it needed to go beyond search. I don’t think they understood the business model very well. To me, it was like the Internet was information and this was going to be the portals of all the Internet information in the world. It seemed pretty obvious to me.”

“So I worked at the architecture firm for about three years, working late hours and saving every penny. Then around 2005 I met this entrepreneur from California who was running a locally targeted test market for a job search website”

“So this guy would come to Omaha often and we started working together because he needed a lot of design work done. Then he would disappear for months at a time and all of a sudden show up again. He kept talking about how he was trying to raise his VC money and wanted me to work for him. I didn’t really know what he was talking about at the time, so I thought he was crazy.”

“Eventually he raised venture capital, $1.7 million or something. He was a typical Silicon Valley entrepreneur: sort of scatter-brained and erratic, but fun. We’d do some work and then we’d go out for drinks when he was in town. He was really proactive and made you feel special. He talked about moving me out to California to be their designer. I thought that would never happen because he was from the Bay Area and there were already so many great designers out there. That wouldn’t make any sense. Why would they do that? But they did it, and I moved to San Jose in August 2006.”

“When I told everyone in Omaha that I was moving to California, it seemed like people couldn’t be happy for me. Instead it was ‘The traffic is terrible there, the cost of living is really high, and you’re not going to get paid enough to live out there.’  All those things weren’t important to me. The important things to me were enjoying the work I did and working with people I liked and had a lot of respect for.”

DAVID WAS EXCITED, BUT THE NON-FLUSHING TOILET AND THE URINAL ON THE FLOOR where it had fallen from the wall, along with the old stained wood paneling on the walls of David’s “new” office in downtown San Jose made him think, “What did I get myself into?” But then he started working and felt like he was finally with people who understood him.

“They respected my opinions and ideas, they never said no to an idea and they wanted to work. There was a lot of energy. I was with them for a year. Again, I was the one-man graphics department designing and managing everything form the website to business cards for the sales team. I worked long hours. At first, it was just exciting and I loved it, but slowly I became unhappy living in suburban San Jose and with the way the company’s resources were being used. The Board included some of the most successful VCs and I thought that they must not have known what was going on because there was no way that this was the way they would run a company. We had grown from 15 to 90 people in less than a year, and there was no measurement going on how to best get sales, optimize the e-commerce flow for posting jobs, or measure how much money it cost to get somebody to post a job via e-commerce versus somebody calling from sales.”

“But the exciting thing was I was around all these entrepreneurial types. I was friends with people at startups like Meetro which was a bunch of guys working and living together trying to grow a company. It was exciting. I felt like I was surrounded by people who made sense. They weren’t worried about things that seemed really mundane. They were interested in following their curiosity and solving problems.”

“Then around 2007 after moving up to San Francisco, I found out about a design position at another start up, which was basically a Yelp for green and sustainable products and services. I was really searching for better meaning in my work, and working for the green sector seemed like it could satisfy that need. So I quit my job and started there. I remember when they hired me they told me they had previously gone through 11 designers. So I just tried to structure the conversation around business objectives like what was the company’s direction. They were thrilled with my work at first, but the problems within management were manifesting themselves in the branding and marketing of the company. If you don’t know what your company is, it’s hard to represent that.”

“They weren’t a technology-led company. The CEO had an entertainment background and was very talented at raising money, but didn’t have an understanding of how to grow this kind of company organically. Instead, it was like ‘Let’s throw money at this and see what happens.’ It was surreal. There were organic fruits at the office all the time. We would get massages and have company parties where they’d cater organic, farm-raised meat and vegetables. But it felt frivolous. I really wanted to feel like there was a sense of importance to the work. I think that’s when I realized that if it wasn’t mine, I wasn’t going to care about the work very much.”

“I was at that company for eight months until I got fired. I don’t know how I got fired. I didn’t really ask a lot of questions because there were battles going on in every direction. The company was trying to do so many different things at the same time. At that point I had enough money in my stock portfolio that I couldn’t find any reason to care about the job. I probably should have quit sooner but I still was that Nebraska boy who was afraid of not having a job. When they fired me I said to my boss, ‘Well, this will be a special day in my life, July 17, 2007.  This is the last day I work for somebody.’ People thought I was being dramatic, but I was serious.”

THIS IS WHEN DAVID STARTED THE PROCESS OF EXPLORING WHAT MOTIVATED HIM, and he found it to be tough. First, he had to get over the idea that he didn’t have a job, but cashing out 40% of his portfolio when the market was high helped quell that fear. Now he just had to figure out what to do with his time.

“I felt drained from working at my jobs – having to compromise my standards of quality and deal with the consequences of other people’s decisions when I felt I could make better ones. I wanted to do work that I thought was good and that I could be proud of, and wanted to recapture the feeling of being totally immersed in something, being in the zone and shutting out the world.”

“So I came up with this idea, ThroughAFriend, a Facebook app that was like a socially-intelligent craigslist. It used your social connections in Facebook by using a profile box. You could hit the support button on your friends’ listings all looking for, say, roommates. I spent months just on the specs because I couldn’t build it myself but I wanted to think through the whole product and really just make it awesome and get into all the details.”

“I made this PDF spec sheet to share with engineers to get quotes and stuff. I changed my schedule so that I could work until 4:00 a.m. and then sleep until the afternoon so there were no distractions. I worked on that for about a month-and-a-half, just doing graphics and thinking through everything. I hired a friend who was a fantastic engineer to design the back end while I designed the front end. We built this app, got it out there and it grew.”

“Then Facebook changed their API and removed the profile box and it just went straight down. I realized that it wasn’t a good idea to build on top of somebody else’s platform. Also, I wasn’t equipped to fix it. I didn’t really have the resources. The drive to raise money and get a staff going wasn’t there. That’s just not the way I operate. But I felt very good about the work.”

“It was fun because I was starting to take on this identity of being an entrepreneur, even though many people still thought of me as a designer. But I knew I was becoming an entrepreneur, and that I was interested in exploring and solving problems.”

“Then I decided to move to Chicago. I realized I’d gotten everything I could out of San Francisco. It unlocked creativity and built confidence that I never would have found otherwise. But I also felt that things had gotten out of control there, like there was a bubble going on. I was tired of constantly meeting that type of entrepreneur who was able to raise a bunch of money over a half-baked idea. I just couldn’t look into their eyes and see the motivation – to understand why they were doing what they were doing. Was it because they just wanted the prestige attached to raising the money? I felt there was all this noise, even though there was also a ton of opportunity. I also missed being around people who did regular things. I missed brick buildings, trees and seasons. I didn’t feel like I could just bear down and work on a project like I did when I lived in Omaha when it was snowing; that’s how I learned how to program, that’s why I worked on my blog. When there’s 12 inches of snow falling and you’re not going anywhere, what else are you going to do?”

“So I sold everything, packed a suitcase and moved. I got a place in the Ukrainian Village and shared office space with a couple of my friends who were running creative companies, which was great because I learned so much from them about that. Thanks to my connections from The Valley, I was able to land some big clients, and I started experimenting with projects. I was also writing a lot and realized how much I liked it. I found the Hacker News audience and figured out what sort of things they liked to read about and how to make blog posts that were useful and got traffic.

Then I remembered that I had done this presentation called Design for the Coder’s Mind where I did reverse-engineered visual design. I talked about design, color and geometry of grids in designing layouts. My goal was to present it at South By Southwest. So I came up with this idea about how to create something appealing.”

DAVID WASN’T FAMOUS, BUT HE KNEW HOW TO DRIVE TRAFFIC. To speak at the conference he had to get votes from a panel, so he figured he’d write a really great blog post to get the attention he needed. He wrote about the typeface Garamond and how it was designed so long ago as a lead type for print, which meant it didn’t translate well on screen with pixels. Since pixels are the unit used, that defines what makes good typography onscreen.

“I spent a couple of weeks working on it then posted it on my blog in July 2010. It was called Why You Don’t Use Garamond on the Web. It was an instant hit. It had 20,000 views within a couple of days. Then I got an email from John Wiley & Sons telling me how much they loved this idea of reverse-engineering beauty and offered me a book deal. It all happened so fast. I didn’t get a SXSW panel that year, but I did get a ‘book reading’.”

“It took me about six months to write the book. I was in my apartment by myself during a terrible Chicago winter. I had hardly any social life because I worked so much. But I didn’t consider myself disciplined, just paranoid. Just motivated. I joke that I don’t think I am a perfectionist because if I were, I’d do even better. Sometimes you just have to get it done, and sometimes those things turn out really good.  I think a lot of creative work is impulse and things that you don’t understand yourself. Like Steve Jobs says, ‘You can’t connect the dots moving forward.’ ”

“I had so much to say. I discovered that sometimes the things that are the most powerful to explain are the things that are so obvious to you but you don’t realize that the information you know might be helpful to others since not everyone else knows those things. I felt like I had been waiting a long time for this to happen, so I was going to seize this opportunity after spinning my entrepreneurial wheels long enough. I was worried about doing a good job. I had to organize all this content and it was a lot of work. I had a lot of anxiety about writing this book and meeting the deadlines.”

“Then I did an entrepreneurial retreat in Costa Rica with some friends, Noah Kagan of AppSumo told me to put everything on a calendar and break it down into steps. Once I spent some time doing that, everything was okay. That’s when I started to get into a rhythm. There were moments that really sucked, but then I caught myself one late night sitting in my apartment with books strewn about and the whiteboard on the floor, and it felt very natural, like, this is what I should be doing right now. It was natural but it was also painful. Pain is always a part of the creative process for me, just freaking out about stuff and then finally reaching a moment of clarity about what I’m doing. I’ve gotten better at managing that creative process after doing it time and time again.”

“The book is doing really well. I don’t know what that means yet. I’m discovering that there’s an audience with a hunger for this sort of stuff. It’s all part of my entrepreneurial process: finding what makes my heart beat fast and tickles my brain, yet other people also want. I love entrepreneurship and start-ups. If I ever have enough money I would love to be an angel investor. That would be so cool to make ideas happen and enable other people to navigate the entrepreneurial process because I think that self-actualization in our society is being a successful entrepreneur; that turning your passions, interests and relationships into a sustainable living is the definition of happiness in our society.”

“You’re on a team with 15 people and you’re all friends. You all hang out. All the pool time is social time. We were competitive with each other, too. You develop this culture where if you slack off, if you start slowing down, if you don’t try your hardest, you’re letting down your teammates. It was a simple and powerful lesson. If you start falling behind, complaining about the pain or how tired you are, people make fun of you, and don’t take you seriously. You end up trying your hardest every day.”

“Once I realized I was not going to be an Olympian, I changed focus to academics and worked hard on that. In middle school I was just getting by, until I went to our graduation ceremony and saw everyone but me deliver a speech on stage. Then in high school, I got A’s every semester and became very competitive. It became a game. I just wanted to be the runner ranked as a top speed.”

” I always knew I only have myself to blame. If I screwed up because of something I did, I would be upset. If somebody else screwed me over, it never bothered me. I could only screw myself over. My parents never pressured me. They never said, ‘If you don’t get these grades you have to do this or you have to do better in school.’ There was never any of that. It was just a big game to me and I love to compete.”

HIS BROTHER WOULD DESTROY HIS LEGOS, Erdem would destroy his computer disks. That was the language the two brothers would communicate in during their competitive upbringing. His brother already showed symptoms of a becoming a computer wiz at the early age of six and Erdem’s father contracted the entrepreneurship bug in his fifties. Needless to say, Erdem caught both viruses.

“My brother and my dad are both engineers. My dad ended up in the United States via Turkey to do his Ph.D. after he finished his undergraduate work. He did his Ph.D. at Berkeley in civil engineering and then went back to Turkey for two years. He met my mom and they got married then moved back to the Bay area. He worked at Bechtel until he was 52 and then he quit and started his own two-man engineering company.”

“I was 17 at the time when he launched it. I was excited because I knew it meant he was going to be home a lot more. I admired him for taking the risk because I knew he still had to pay for my brother’s college tuition, and mine was coming up. He just said, ‘I’m tired and I’ve always wanted to do this.’ He never expanded beyond two employees. His company has a great reputation as being the best in its category and always highly ranked in magazines. He’s a really talented civil engineer and software developer, which is a rare combination in one person. He was never into being a big business guy. He didn’t have a desire to build a huge company, he just wanted his own business.”

ERDEM‘S GUMBALL KIOSK would have made his father proud. “My earliest experience as an entrepreneur was when my friend and I had a little store in elementary school. We set up a table and we would sell gumballs and trinkets and little things. The kids would skip their lunch and buy stuff from us. We would go to Costco and buy the giant size. It was so easy. We would put five gumballs in a cup and sell them for ten cents a piece. I don’t know how many gumballs were in a jar but we sold it for $8. It was a huge mark-up on each gumball but the kids would come to us with a quarter or two quarters, whatever they had for lunch money. It was great.”

“Then during the dotcom era I was in my senior year in high school, and there were all these websites doing pay-per-click. You’d set up a website, take ads and put it on your site and if you got clicked on, you would get one dollar per click. It was a recipe for disaster because it was all pay-per-click and it was generous. You would get a dollar just for someone signing up. So in my conniving thinking back then – now integrity would stop me from doing such a thing – I would set up my computer in my room while I was in school, dial in, the thing would click the ad, go to the website, drop in a text file, put in fake information, submit, go back, click again, submit fake information, then repeat. The first month I made $440. The second month I made $2,500, and then the company went out of business. My thinking then was this is crazy, but I’ll take advantage of it while I can. That $440 funded my trip to go to the Junior National Championships in Texas later that summer.”

ERDEM ALMOST BELLY FLOPPED, his application to MIT. “I had already applied to Harvard, Stanford, and Berkeley, and my parents said I should apply to MIT just to see what would happened. I ended up turning in my application incomplete. MIT called me and said, ‘Hey, you’re missing some pieces here.’  I said, ‘Oh, don’t worry, I’m not done with the application. I’m going to send you the rest of it later on the final application’. They get the final application and called again to say, ‘We still don’t have certain pieces of your application. You haven’t taken the SAT II.’ They told me the deadline to sign up for the last testing session had past. They told me if I showed up to the test, they might still let me sign up right there and take it. I’d only studied some biology but I figured, what’s the worst that could happen? I took the exam and did well. The whole time I didn’t seriously think about going to MIT but for whatever reason, I pursued it and finished the test. I got a good enough score and got accepted. So that’s where I ended up going, making it by the skin of my teeth.”

“At MIT I swam competitively and joined a fraternity. Back then everybody had to pledge. I started off pre-med to follow in my family’s footsteps: my grandfather was a doctor, my great uncle is a doctor, my cousins are doctors, so lots of people wanted me to be a doctor, too. So, I was pre-med but I didn’t like biology too much. A buddy of mine suggested I try electrical engineering. It was one of the best programs at MIT. I took some introductory classes and liked it. So I kept doing it and ended up with a degree in electrical engineering and computer science.”

BAILING WATER ON THE S.S TITANIC.COM, Erdem interned at a procurement company, Areba, in Silicon Valley during the summer of 2000. It was one of the biggest boom-and-busts of the “dot com” era. A friend and I were living in the South Bay, saving every penny and living off of rice and beans. When we weren’t working we amused ourselves with cheap thrills like joining the YMCA at a discount, playing old Nintendo games and just hanging out.”

“Then I started working on a mix of finance and software development, so that next summer I got an internship in London at UBS working as an IT developer for the foreign exchange desk helping traders calculate certain rates and spreads. London was exciting. During that summer, I discovered that I wanted to be more on the trading and investment side than on the computer science side. In a banking environment, the software developers are not the hot shots.. So, from my perspective as a 19-year old kid, it was more exciting to be on the front end. The trading and investment side of it was interesting to me and not totally unfamiliar since I got my first stock account when I was 12. I had bought Unicom, a company in Berkeley that was installing wireless modems on telephone towers. They were way too ahead of their time, but it was awesome technology that enabled me to carry my desktop anywhere and get Internet connection. They were just so brilliant and it was fun being in on it from the start before everyone else.”

“Then the summer after my junior year, after not getting an internship at Goldman Sachs, I started another internship at the lab for Financial Engineering at MIT where they were research testing trader decision-making in emotional/high stress situations. That same summer, I reconnected with my old boss from Ariba and launched a company called Accelovation. It was important that the name of the company start with the letter “A” so that whenever we got listed, it would always land at the top of the list. The idea was that all these companies like IBM develop technology and file patents for everything, but some are off-the-wall things or for specific things that no one knows how to apply to anything and they just end up being filed and never used, and never monetized. Companies like DuPont and Dow Chemical have all these patents, a small fraction of which is used for anything. Intel files 3,000 patents a year or something crazy like that. We wanted to see if we could connect all this technology with solutions to problems people were having and automate the solutions somehow. We got in touch with a woman at DuPont whose job it was to just sift through patents and figure out what to do with all of them. She really had no tools to do anything but read something, figure it out, and then brainstorm about how it could be used. That’s difficult.”

“We talked to her about how she did her job and how we could do it better. We did an alpha project for DuPont for free where they gave us a portfolio of 30 patents they thought were interesting but weren’t monetizing. We thought our technology could be very useful to patent lawyers and people were trying to find new uses for technology even for science fiction writers who were trying to figure out new uses of technology. It really worked, but it was laborious. We had to filter through the results ourselves, and probably half the results were total junk.”

“Then I came to a decision at the end of my senior year that my partners had more experience than me and were moving the business ahead while I was contributing less to the process. I had done all the software development to build the system and now they were busy running the business. I felt I couldn’t do as much for the business as a 33% stakeholder would warrant. At that point, I didn’t have the experience needed to help push the business further. I think it was the right decision. Plus, I still own a small fraction of the company so the better they do, the better it is for me.”

“So I left to join this hedge fund in Chicago, and I didn’t know what an income statement, balance sheet or a cash flow statement was. I didn’t know much accounting. So, I went through a summer training course where for two months they brought in professors from Chicago to teach quick classes. It was like a quick and dirty MBA program. I went through that and came out the other side ready to do some financial analysis and was put into their rotational program. I learned to be really creative about using all sorts of resources, like talking to top-level management at all these companies. I got to know all of these CEOs of various companies in a wide range of industries and learned how they founded their companies and how they got to the point where they were. Some of them were the children of the founder. I learned to spot which companies were and weren’t good. I got to study commonalities and what made a good business model. This began to inspire me to start my own company again.”

SWIMMING SOMEONE ELSE’S LAPS seemed just as silly as working for someone else to Erdem. “The idea of working for somebody never appealed to me. So, I saved as much of my bonus and salary as I could. They were good bonuses. I was hoping to bootstrap the whole thing and never need outside capital. At that point I was talking about launching something with my friend Kale McNaney. He grew up in Buffalo and also went to MIT, did a bunch of engineering computer science, and had interned at Merrill Lynch.’

“I was still working at the hedge fund when we launched our new company called OddJobs. It quickly became clear that our business wasn’t going to go anywhere if I stayed full time at my job where I was working from 7:00 a.m. to 8:00 p.m. I was trying to work with Kale from 8:00 p.m. to midnight but my mind just wasn’t there. So I waited until my last bonus check cleared and by March 16 I said that’s enough, I’m ready. I’m going to go off and do this full time. That was just over nine months ago, and Kale came on full time in August.”

“Our company was based on the idea of a text messaging network where you could text a message to anybody within a certain distance and ask them to run errands for you. You could say ‘I need flowers delivered here.’ Then somebody who was walking by a flower store would receive that text message with an offer like ‘For $10, will you pick up these flowers and bring them to me?’  And that person would reply yes or not reply at all. I was interested in this idea of making ‘local human labor’ more efficient. It made sense, but the logistics were difficult. We thought a lot of our competitors were interesting, so we did some research on one of them and found out that over the 12 months that they’d been in operation they had made about $10,000. We knew from the marketing we had seen and the staff they had that they were spending way more than that. We didn’t know immediately what they were doing wrong. It just made us question the whole market, how big it really was, no matter how much money they were raising from VC funding. We lost that excitement of errand running being this huge future financial opportunity. So we switched focus from local, neighbor-to-neighbor services to professional services like Service Magic, Angie’s List, Yelp, and Google to see how they worked at attacking technical challenges. (We try to avoid using the word ‘problem’. I try to stay strict about that. I don’t like the word ‘problem.’ I like ‘solutions’ and ‘challenges’.)”

ERDEM GOT THE DIRT ON ENTREPRENEURSHIP AT A CLEANING INDUSTRY CONFERENCE in Phoenix. Erdem didn’t expect much excitement, but he ended up learning a lot more about entrepreneurship than cleaning. These entrepreneurs had never worked for anyone else in their lives. Some had high school or college degrees, but all had built their business from the beginning with revenues anywhere from $300,000 to $10 million. They were all passionate and interested in how to grow their business. Erdem was anxious to talk to these guys about his ideas and ask them what they thought of all those products like Yelp, Angie’s List and Service Magic competing for SEO, social media and advertising, local ad networks. He just listened to what they had to say.

“We wanted to do it differently. We first started out with a business model based on 10% commission but that constrained our growth.   We had to collect a credit card from every business before they offered a quote on a job. At this point we figured out that we had two options. We could work harder to recruit businesses to pay us in a certain area as soon as the job was posted. For instance, if someone posted a job in San Francisco, and we had no plumber in San Francisco, for the next 24 hours we could call plumbers trying to find people to sign up and pay us 10%. Or we could make the number of businesses in our system independent of the consumer experience, which is what we ended up doing. We decided that it didn’t matter if we had businesses signed up or not, we could just connect the customer to the business. So we got rid of the commission. Everything was free. But at the same time, we went from being able to handle only half our jobs in Chicago to being able to handle any job anywhere, which was great. Now we can handle most anything. We even had an actress ask for headshots and she got six quotes in a day. It’s totally seamless for businesses.”

We’ve recently reinstated a commission structure so that businesses can choose to pay a commission but we let them choose what they pay.  We figured no one knows a business as well as the business owner so now we just ask them to choose a commission they feel is fair.  Then we do our best to deliver them more customers within those constraints. We operate on the honor system, we figured if we can’t trust businesses to pay us what they promise, how can we expect our users to trust them either.”

GETTING UP IN THE MORNING IS EASY when you look forward to your workday as much as you look forward to playing your favorite video game. “It’s a lot of fun. I’ve been looking for that feeling, you know, like when I was seven or eight years old and I got my first Nintendo. We got the Super Mario Brothers and all I wanted to do was wake up as early as possible to play for an hour before school and play an hour after school. That was all I wanted to do: play Super Mario Brothers. I was looking for that feeling of excitement, that all I wanted to do was cut my sleep short, go to sleep later, or skip lunch to do more of this. I actually have that feeling now. That’s exciting.”

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Tom Kuczmarski spends every waking moment of his life making sure that tomorrow is far more interesting than today. He’s been a teacher at the Kellogg School of Management for three decades, a seasoned consultant, and an innovator’s innovator. He also knows that things don’t always come-up-roses, like when he ventured into the flower business.

An aggravated customer offers a dead flower to a shopkeeper who suddenly loses interest in staying in the flower business. “The day I knew it was over was when a woman came in on a Sunday and she came up to me with her one hand on her hip and this bouquet of dead flowers in her hand and she said, ‘I bought these flowers ten days ago and look at them – they are dead. I want my money back.’  I thought, ‘It was ten days ago! They should be dead!’”

Home of the Basketball Hall of Fame (and Tom), Springfield, Massachusetts doesn’t just host’m, it creates Hall of Fame talent. Family life was pretty low key and laid back for Tom and his folks living in the rural outskirts of Springfield proper. Tom stayed in Springfield through college at Holy Cross in Worcester, Massachusetts, until grad school came banging down his door and brought him to the Big Apple and Columbia University. “I was a good kid, and at about age ten I started my first entrepreneurial business. My parents had given me a movie projector and I charged a quarter for kids to come watch movies in my basement. And I still have my record of the money that came in. I think it was twenty-two bucks—it was big money!”

“Growing up, I had my own lawn service as a teenager and by the time I went to undergrad I had all sorts of jobs. Then by the time I went to graduate school, at Columbia University, I was teaching eighth grade English at the Cathedral School of St. John the Devine, had my own ‘bartendering’ business, Tomski Bartendering, with a tag line of ‘Feel like a guest at your own party.’ I would do private parties. I also did American Indian dancing at the same time, so I was busy in graduate school.”

“Early on it was the same goal an entrepreneur would have—how do you do something and survive, grow it, make money? Yeah, I needed money. When living in New York I found that the energy, anonymity, and the diversity—all these things just coalesced. I was doing the bartendering, the American Indian dancing and teaching at the Cathedral School. And I got paid big bucks for that—I got paid $100 a performance for that Indian dancing. I would dance through a hoop that would be on fire, all sorts of cool stuff. I started the troupe. We did events. It was something I got involved with as a kid. It didn’t have a name but I kept it very authentic and very real as opposed to ‘woo woo woo’ type of mockery you see on TV about Native Americans. When I was at Columbia I took a course with Margaret Mead and I did a paper on the Iroquois League of Six Nations and their Democratic Approach. She wrote four pages of notes on this paper which is pretty cool.”

Working for “the man” is part of a complete breakfast, and a great reason for Tom to take his talents Chicago.

“Being at Columbia was great. I got a Master’s in International Affairs and then an MBA. After graduating with a Master’s in International Affairs, I got a $10,000 a year job offer from the United Nations and a $10,000 a year job offer from AID. Both were great, but I couldn’t live on $10,000 a year in New York City with school loans in 1974.”

“Not knowing if I would get a job offer or not, I actually ended up with a bunch of them and I took one with the Quaker Oats Company here in Chicago. I wanted a job—I wanted to pay these school loans. I wanted to go work for ‘the man’ and make some money. Of the offers I got, I liked Quaker Oats the best because of the people there. I was going to stay here for two years and then move back to the East Coast. Quaker Oats was great and I was starting to understand a little bit about business, but I wouldn’t say I was totally cognizant of the underpinnings of business, but I was starting to get it, and like it. “

“They put me in charge of new products at Quaker and I didn’t have any idea of what I was doing. In 1976 through 1978, I worked on two projects; I worked on Aunt Jemima Frozen Crepe Batter, which lets you pour in your frying pan and have beautiful crepes. That was launched and lasted in the market about nine months before it died. The other was Chewy Nut Granola Bar and I was always fascinated at—here you have two products—what makes one a success and what makes one a failure.”

“After that, I went to Booz, Allen & Hamilton and worked for them. They were a management-consulting firm but I was able to focus on new products and new services while I was there, so I did a lot of work in that field and really got turned on by it. I guess I saw, shockingly, that so many companies were doing it wrong and I kept thinking—why are they doing it this way?  That lasted five years and that is when I finally said, ‘I gotta go back and do my own thing!’”

Fearing the golden handcuffs, and with a child on the way, Tom needed to make a switch, and fast. “Between Quaker and Booz Allen, it was about eight-and-a-half or nine years. I was in my early thirties when my wife told me she was pregnant with our first child. I said, ‘Oh, my God, I gotta get out of this before I get sucked in forever!’ But two years into good old entrepreneurship, with my total income having significantly decreased from what it was at Booz Allen, I decided to go back to Booz Allen and say ‘I’ve found the right path and I learned my lessons.’ I went back and I just couldn’t do it. I left there saying to myself, ‘Oh God, I’m screwed. I’ve got to make this entrepreneurial thing work.’”

Tom was a hungry man filling his plate up at the buffet of business, but much like a food buffet, after the third or fourth, you’re quickly reminded of your own mortality and that last half-eaten samosa is just gonna have to be left behind.

“When you are a super star you think you can start multiple businesses at once, so at the age of 32, I started Kuczmarski & Associates which was consulting for cash-flow purposes. I actually was teaching at Kellogg and I’ve been teaching there for thirty-one years. I started a flower business called ‘Blossoms Anytime’, I tried to start a nightclub called Tommy K’s, and then my wife and I were going to open the Oxford School, which was going to be a private school, and we put a bid in for a place on Magnolia. Do you see any problem with starting five businesses all at once?  I would say it is pretty ridiculous.”

“My primary income was coming from the new products and services at the consulting business. Early on the teaching was covering the cash flow. The flower business lasted for two years and the nightclub never got off the ground. It was fantastic because I learned, by the time I was thirty-four, who I was as a professional, a teacher-writer-consultant. It was writing books and teaching consulting and that’s who I was. I was pretty lucky to figure that out at age thirty-four.” (Tom has been consulting for twenty-eight years, spent thirty-one years at the Kellogg School of Management, and is releasing his newest book (his sixth) coming out on November 8th.)

You’re only as good as your last innovation, in the world of consulting. “We have twelve full-time people and five contractors so it is small in terms of its size.  We try to take on only three or four projects at any point in time so we can all be involved, as opposed to just sell the work and not do the work. It works out really nicely. We like it. We have four, five, or six people on a team working with a client and we do B2B and B2C. What we’ll do is develop the innovation strategy for a company. Then we will go out and do the qualitative research with consumers or with the customers to find out their problems, the user needs. Then, we will help generate the ideas or the solutions, turn those into concepts, take those back out and test those concepts.”

“A big thing for us is putting together a business case so you can provide real-world numbers to a client so they are able to make a decision.  Then we go to a Gravitytank like company and start having designs and prototypes made and start implementing things in the market place. It is the type of business where you are only as good as your last job sold, so our projects are four, five, or six months in length.  You constantly need to market yourself and get the word out and continue to focus on selling—prospecting while you are doing the work. It goes in waves, where people will get it, and there will be a good balance, and then we’ll be too focused on doing the work. It’s like riding a bicycle and then you take one wheel off—you fly off. I think that balance between doing the work and selling the work is always a challenge.”

“Innovation usually gets wrongly defined as high-tech. I define it this way:  it is any new offerings—so new offerings can be a service, a product, a business, a process—that provide new benefits to some end-user—whether it is B2B or B2C, or constituent, or employee—that is differentiated from competition and ultimately is valued by the consumer or by the customer. If you have those conditions in place, that is an innovation and in turn, that is what drives economic value within a company.”

“Too often, companies start there and they say ‘we have to fill a growth gap or we have to increase our margins, so let’s come up with some successful new products and new services and some new businesses,’ as opposed to going out and understanding first what the un-met needs are in the market place. And, then, of course, everybody says, ‘but with technology in particular, people don’t know what they don’t know.’ People have frustrations and they have pain points, but it is how you enable technology to try to address that to make people’s lives easier or better, improved, etc., where the two come together.”

“In the short form, innovation is a solution to a customer or consumer’s problem, frustration, or a need. Whoever does that the best, wins.”

Silicon Shmilicon, Tom was sick and tired of hearing about Silicon Valley juxtaposed to Chicago with the implication that Chicago is an inferior place to do business.

“There was a reason the Innovation Awards started eleven years ago, and it was two-fold. I love Silicon Valley and I think it is fantastic but there is a heck of a lot of great stuff going on here in Chicago. So first, how can we shine the spotlight here, and second, I just find in most organizations they do a lousy job of recognizing and rewarding people. In most companies people get paid the base salary and some bonus to develop some great new services, new business, new products, and rarely do they get any other form of recognition—in large companies, for sure that has been the case.”

“I wanted to try to do something that would say, ‘Hey, wait a minute—this innovation stuff is difficult, it is important, and it is valuable and we should be recognizing people more for it.’ So, I went to a couple of periodicals here in Chicago with this idea and they said ‘that’s a dumb idea.’ Then I went to the business editor of the Chicago Sun Times, Dan Miller, and he said ‘that sounds like a darn good idea. Let’s give it a try one year.’ So, we did.”

“Ten years ago we had seventy-five people come to the first Chicago Innovation Award at The Sutton Place Hotel across from Gibson’s. Dan said to me ‘there is a lot of energy in this room’ and I say, ‘yeah, there really is, it’s really amazing.’ At the first Chicago Innovation Award event, we had the inventor of the remote control, Gene Polley, and he was eighty-two or eight-four years old and he just thought this was great. So, Dan says, ‘well, should we try it again, one more year?’  And I said, ‘okay, let’s try it again one more year,’ and so then every year it has continued to grow and grow and grow. Five years ago is when we started saying, hey, let’s not have this be a once-a-year event, let’s start adding additional activities and different events each year.  Now we are up to six, so that has really gotten the word out.”

Keep your patents off my stage! It takes more then a couple of trademarks or patents to win admiration at the Chicago Innovation Awards.

“One of the ground rules set forth from the very beginning was not to reward people for just a great idea or just because they have a patent or a trademark. That is not what the Chicago Innovation Awards is all about. You must have demonstrated success in the marketplace. We never set any minimums or tried to define what an acceptable range of success means but you have to have some revenues.”

“People in the marketplace have to be saying something good about your service, or your product, or your business, and there has to be a real strong connection between what you are doing and a need in the marketplace. It’s great if it’s a new whiz-bang technology or something that is cool and satisfies a real need in the marketplace, but, it’s even better if you created a new category, or created a new space or a new segment. What we have also tried to do is create a portfolio for each year—a portfolio of innovations going on in Chicago is important. That is the other thing—it is innovation across industries, it is high-tech, low-tech, no-tech, small start-ups, and big corporations.”

“14 judges meet four times for 3 hours each and we start with the folks in my firm and, you know, Luke and Bryan and the other Chicago Innovation Awards people, and they do a really good job of sorting through those 409 nominations. The next meeting, we get it down to the top 75 and the top 75 are then the ones that go on the website—they are the candidates for the Peoples’ Choice Award and people can go vote on those top 75. Then the judges take it from 30 to 10 which is painful because there are not just 10 good nominations. There could easily be 15 or 20 winners.”

“The challenge for the event is, what is the business model that makes sense? From day one, you go to the awards and all these other events that we have—the nominee session, the media day, the Kellogg Practical Innovator Training Day—all of these things are for free and nobody pays anything for any of it. Our funding has come from sponsors, relationships and pride of the community, etc. What I’ve always said to these other folks is, you have to find those two or three folks—a media partner, a corporation, and an academic institution. You get those three onboard, and you’ve got the start of something really good.”

“The only thing that we haven’t talked about that could make sense is if it was on a national level—the American Innovation Awards or the U.S. Innovation Awards. That would be something I would be interested in trying to think about and even some of our media partners in the past, like when we’ve had Bloomberg Business Week, are ones that could certainly be a national sponsor. We wouldn’t drop the Chicago Innovation Awards, it would be in addition to the Chicago Innovation Awards—we could have the U.S. Innovation Awards.”

“This is the 10th anniversary and it was about a year-and-a-half ago when we said ‘there will be 100 companies that will have won the Chicago Innovation Awards on November 8th. Wouldn’t it be cool if we could do a book that would portray their stories in it?’  Although 10 companies said they did not want to participate, we have 80 of the 90 so far portrayed in it.  In each one of the stories, we talk about the consumer/customer problem, the solution they came up with, what makes this unique, what was the break-through moment, what was the impact of their innovation, and what they see for the future. That’s cool.”

“We are using Bookends Publishing, which is a small regional house, to help publish the book. The myopic problem for a couple big book publishers, which we didn’t agree with, was ‘this is Chicago, only Chicago people will buy the book.’  I said read the subtitle—it says ‘How Local Innovators are Building the National Economy,’ so this should be viewed as a great model for other cities throughout the entire country of why entrepreneurship, why innovation is so important.”

There is no final hurrah, when you eat, breathe and sleep innovation.

“I have written so many books because it is the same thing for an entrepreneur. Does an entrepreneur build just one business and leave it at that?  If you are a true entrepreneur you are going to keep coming up with stuff. Why do you?  I don’t know why you do but you do. It’s the same thing if you are into writing books; you are coming up with new books all the time. But for me there are two categories when thinking differently about leadership—Values-Based Leadership came out in the mid-1990s and then the most recent one before this one was Apples are Square.  That one was published by Kaplan and that one has done great. That was picked by Fast Company in 2007 as one of its top fourteen best business books of the year and it sets up a whole new leadership archetype and basically says that the old boy control and compete form of leadership is now dead and gone. Well, it’s not dead; but it should be dead.”

“The new leadership construct that we talk about in this book is one that is based on humility, compassion, relationship building, collaboration as opposed to competition, decisiveness (but decisiveness is based on values, not just on profits), transparency or openness, and inclusivity as opposed to exclusivity. When you think of that type of leader, somebody who is humble and compassionate, cooperative, transparent, and open and vulnerable, it is a different type of person but it is someone I feel strongly is going to be leading more progressive innovative companies in the future as opposed to the old Jack Welch’s of the past. I can’t say it didn’t work because it did for him. So, one category is leadership books and then the other is innovation because those were Managing New Products, Innovation, Innovating The Corporation, and now Innovating Chicago-Style.”

To say Tom is a busy bee is an understatement.  Tom is currently still working with Kuczmarski & Associates, the Kellogg School of Management, the Chicago Innovation Awards, and is prolific author of six books.

As for one Tom believes in Chicago so deeply, he quickly fired off a memory from an old friend who was speaking out in ‘The Valley’.

“I was with my good friend Dipak Jain, the Dean at the Kellogg School, on the west coast and we were at a conference. There was the Dean of Stanford, the Dean of UCLA, and I think Harvard, and Kellogg. Somebody asked a question about the two deans at Stanford and UCLA—what role does the weather play in attracting students to your schools?  They laughed, and said ‘Everybody loves the weather here…’ and Dipak was the third person in line and they said, ‘Well, Dean Jain, I imagine you have a very different answer to that question given that Kellogg is in Chicago.’

“He said, ‘Oh, no, to the contrary. What we experience in Chicago is called the Refrigerator Effect and the Refrigerator Effect is that our people are sharper, they are smarter, and they are crisper than anybody on the West coast.’”

“I always loved that as an argument against the weather on the West coast. To some extent it is true. I find people in Chicago have a set of values that are just terrific—I see a desire for doing the right thing, doing good things, a sense of community—and sure you have some people in this town that think they are bigger or better than others, but honestly, I think that is a tiny, tiny portion. It is a small town and as soon as you start getting your feet out there, you keep running into the same people, it is really cool, it is really neat. I think it is the best city of all.”

http://www.chicagoinnovationawards.com/

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 ChicagoWorksForYou.com 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 ChicagoCrime.org, which was basically dots on a map showing every crime in the city. I pitched my concept for ChicagoWorksForYou.com 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 ChicagoWorksforYou.com.”

“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, CityPayments.org, 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.

A quick glance over the room and my first reaction was, “Is it time to call the TV show Hoarders?” There are pictures, creations, papers, and gadgets covering every inch of his office. It’s not until you start to look closer that you realize, this is not junk, it’s all part of the magic show you are about to experience.

Those aren’t just pictures on the wall, they are Hollywood’s A-list in candid shots with Howard. That junk on his desk? Some of the most cutting edge prototypes in the interactive space. Drawers and file cabinets full of past, present, and future innovations; some of which have earned Howard’s companies a large fortune.

Trying to wrap one’s mind around the life accomplishments of Howard Tullman is an exercise in pure futility. As our interview progressed I stopped trying to dissect the details of his life and simply tried to keep up with his relentless energy. The chairs in front of his desk should come with seatbelts.

Where does one of the most prolific entrepreneurs in Midwest history credit the beginnings of his success to? Magic.

“Early on I started practicing magic when I was about ten and that was a big deal when I did that for ten or fifteen years. I don’t do it now but it always felt to me that it was very instructive at that very young age. It wasn’t learning the tricks that was the issue, it was managing the adults. It was hard when you were ten years old and they were going to pay you to come perform at this party.”

“It wasn’t hard to handle the audience of kids; it was hard to keep the parents from looking behind the tricks. You had to be really aggressive in terms of like, ‘You sit down there, too. You are part of the audience.’”

“I know some asocial entrepreneurs, but I don’t know any entrepreneur who is incapable of standing up and sort of presenting an idea for better or worse, as if it is the best conceivable idea in the entire world. I think it could be debate team, which I did. It could be public speaking or maybe it was my magic. I just think that having one of those activities that helps you organize your ideas and present is really important. But in addition to that, the presence and the need to present yourself and everything else is a big part of what magic is about.”

THE SON OF A SALESMAN, Howard saw what it meant to be out there in the daily grind and it had a lasting effect on him.

“My father was a sales guy and he ran a number of sales organizations. He worked for different companies but what he had built up over the years was a group of guys who sort of moved with him. If you grow up in a sales household, it is very clear that you eat what you kill and you gotta get up every morning and put your track shoes on and get going.”

Borrowing from his father’s handbook, he put a sales force to work to do his school fundraising. (Editor’s Note: In many of the Technori interviews so far, there seems to be a strong correlation between children who set up candy rackets and future success as an entrepreneur.)

“I think my first entrepreneurial experience was probably selling those World Famous Chocolate bars. I built a small army of people to sell them for me. It was a classic Tom Sawyer kind of thing. It was just a way of making some spare change. I used my Boy Scout troop to be my vendors. I was the wholesaler and they were the retail outlets.”

Practicing magic and hawking bulk candy were some of the highlights of his youth. For the rest, Howard describes it as being a “typical family.” The oldest of six brothers and sisters, Howard was originally born and raised in St. Louis, before his family moved to Highland Park at age 10.

“Highland Park was a very different environment. Highland Park was sort of an upper class thing so I was exposed fairly early on to this culture where I never would have guessed that when you were sixteen, you would get a new car. Maybe you might get some junker, but entering into this affluent community was really interesting. It was a big change from St Louis.”

“Highland Park was also peculiar in that it was the first time I had ever been exposed to one of these environments where you go to school and the teachers would know two and three generations of the kids who were the older siblings of my peers. It was very disconcerting to be the only one that Mrs. Miller didn’t know who your older brother was.”

AT NORTHWESTERN UNIVERSITY, Howard was drawn to the allure of becoming a lawyer. As with everything he takes on, second place is never an option.

“I went to Northwestern for undergrad (Double major of Mathematics and Economics) and law school and I was the Chairman of the Board of the Law Review.“

After excelling at Northwestern, Howard quickly moved onto what would be a short, but highly prolific law career. In just ten years of practicing law (1970-1980), he would be involved in a series of cases that reshaped the world of business law forever.

“I practiced a very peculiar kind of law. My first five years I practiced almost exclusively large scale class action law. Multi-billion dollar cases where there was no precedent at that time. We literally invented the law and we wrote the class action law that seems so commonplace today.”

“I argued in front of the Supreme Court and I was the youngest guy by twenty years in these rooms . . . As far as the work goes, I was the one who would do it. All these senior partners at all these big law firms didn’t want to do the work. It was great! I had sixty people working for me, traveling hundreds of thousands miles a year. There were about twenty-five large scale class actions in that five years and I was involved in about fifteen of them. Things like price-fixing for antibiotic drugs, price-fixing for drywall, and all kinds of different cases where the government would first investigate it and then the private litigants would come in and file these class actions.”

After five years of dealing with class action suits, Howard decided to make a big change and entered the brand new world of Chapter 11 bankruptcy cases. If you haven’t noticed by now, Howard doesn’t enter a new space, he aims to dominate it.

“I represented Continental Bank and Chase-Manhattan, the biggest financial institutions in the world, in these huge actions and they were all Chapter 11 reorganizations. The law was so new that I would take the cases with me when I would go from district to district. I would literally go to Atlanta and I would say, “The only way you are going to find out what the precedent is in this case, is to call the judge in New York because I was there yesterday and here is how he handled this.” My clients were always the biggest guys in the world and they hired me in particular because I was the national roving asshole. That was my job description.”

SUMMING UP HOWARD’S ENTREPRENEURIAL EFFORTS in one article is quite a task. To tell the story of each would push Technori’s typical 3000 word articles into a word count range that even a PhD philosophy student would dread reading. So, for the sake of brevity, in Howard’s words, here is condensed list of his businesses.

“In 1980, I retired from law to start a business that was the first of what turned out to be four different very large-scale, very public multi-million dollar information management businesses. The first one was in 1980 and was called Certified Collateral Corporation and thirty years later it is still operating, has thousands of employees, a multi-hundred million dollar revenue stream and still a monopoly which basically tells insurance companies what to pay if your car is lost or stolen. I started that business in 1980 with $250 and I hired a couple of other people and then it grew. I financed it originally and then brought in some other employees and investors. We took it public, sold it in about 1987 for about $100 million bucks. That was the first of these information businesses where we developed large-scale, real time databases and then I did about seven more of those businesses. I did cars, real estate, boats, insurance, and customer satisfaction – every one of them was a variation on taking data that was historically being represented and making it current.”

“The second business was called Original Research which did about 12 million phone calls a year to consumers to measure customer satisfaction. Then there was Boats .com and UsedCars .com. Tunes .com was my music business I sold for $140 million and Tunes was started in 1995. UsedCars and Boats were early 1990s. I did the first jobs database in the world and sold it to a group of newspapers. So, I think those were the first twelve businesses. Then there was a restaurant, Hats and Shades, a jeans company, Top Hat, some venture capital investments, CD rom games, and a car business which we just sold for $300 million to ADP. It ran the websites for roughly 6,000 car dealers, about half the dealers in America. More music stuff, more career stuff, more job databases, EBuilder, and experiential marketing. I was the Chairman of the Board of the Princeton Review as well.”

Welcome to the magic show. The more he talks, the more the room starts to fill with energy. There might as well be an orchestra building to crescendo as he quickly changes subjects from the past and enters into a dizzying demonstration of several new Tribeca Flashpoint inventions.

BUILDING THE ULTIMATE PLAYPEN (…I MEAN INNOVATION LAB) is what Tribeca Flashpoint Academy (TFA) is truly about for Howard.

“Here, I do a bizarre amount of things. The first year I wrote fifty ads. A new ad every single week for The Reader for fifty weeks in a row. It defined the whole school. It was really the story of the school. I have a very clear commitment to the fact that I think we have to have one voice. When you introduce something new you absolutely have to beat it to death, you have to really know exactly what the messaging is and you have to enforce it to an amazing extent. Considering that we have been at this for four years we already have an internationally recognized brand as a school in digital media.”

“We probably have ten more businesses that we are about to launch. All of these are new technology-based businesses that we’re spinning out of here. I think that I am a little rare in that most guys who are pure entrepreneurs sort of work themselves out of a job and can only grow with their business to a certain extent. I have been fortunate to do this for as long as I want to in any one business and then bring in a sort of operating CEO.”

“I think that education is really important, but I built it to be the biggest sand box possible. I get to do new businesses, new products, and new projects constantly. The operation of the school will fund and will generate real results and some very impressive things for all of the students; and in the meantime, I also have those same resources for myself.”

“Everyday when I come in I have my business responsibilities, but mostly, my job is to look over the horizon with the new technologies to create new industries and new kinds of jobs for the students. That is a lot of fun and that is why I spend the time that I spend here. I might run out of time but I’m never going to run out of the opportunity to morph things and change things and figure out how to do it.

SUCCEED OR FAIL FAST AND MOVE ON QUICKLY is how Howard operates the projects that TFA takes on. The underlying goal of nearly any academy is to create meaningful and lasting jobs or opportunities for all graduates. When things aren’t moving forward, Howard is notorious for his pragmatic and laser focused way of dealing with people and projects that aren’t cutting it.

“I think what has saved me from having to say, ‘Gee, that was a really gross failure’, to me, is that we fail fast. That is the real discipline. The real discipline is if it is not working, you set some concrete metrics and then you change the game.”

“You see people who just want to go for the cosmetic solutions and we can’t do that. We gotta go hard for the core things. We tell people what sacrifices we expect, and hopefully what rewards there will be, and what bumps there are going to be along the way. They either buy in or they don’t.”

When it comes time to make those tough decisions and figure out who is cutting it or not, Howard doesn’t mince words.

“I guess I could have spent a lot more time focusing on being liked, but that just doesn’t work. You just have to make too many hard decisions. President Clinton once said and he was exactly right, that all the easy decisions are staffed out. It is only the impossible choices that come to the boss.”

“When did it get to be a bad thing to have a short attention span? If you are serious and committed, that is what focus and prioritizing is all about. It’s okay, I’ve spent my time with you. I’m sorry that socially I’m supposed to spend another three hours with you to make you feel good, but that is not why I’m on this earth – I’m on this earth to accomplish things.”

“People ask me all the time if I am having fun and I always say no, it’s not fun. It’s stimulating, it is challenging, it’s super worthwhile, I’ve created thousands and thousands of jobs. I have people come back thirty years later and thank me. I have parents come in here every week and say this school changed their kid’s life – all of a sudden he has purpose, he’s focused, and he loves what he is doing and thank you so much.”

“I get a lot of strokes and a lot of gratification, but I work like a fucking pig. I work about 100 hours a week and I know what 100 hours really represents! I always hear people who say they work eighty hours a week. Try doing the math on those kinds of numbers. What you realize is that you have about seven hours in the entire week that you are off, apart from sleeping, maybe four hours. Essentially, my day starts around five and I’m here by six or six-thirty. I leave around six or six-thirty, I don’t eat lunch, and I don’t stop. It’s not like I put my feet up and read. Then I go home and I have dinner with my wife if she hasn’t already eaten by the time I get home which is a 50/50 bet and then she retires at nine or nine-thirty and I usually work until about midnight. I sleep from about midnight to three or four and then I start again. That’s how it goes. Part of that is an outgrowth of businesses on both coasts. The calls never stop and part of it is this is what I love doing.”

CREATING BUSINESSES THAT PERFORM AND LAST is more important to Howard than anything else. His love of innovation and disrupting industries might drive him to take the lead, but he knows when to back away and he has one of the single most important leadership qualities: the ability to get people to rally around an idea as if they came up with it themselves.

“Around here I have had a lot of employees and a lot of partners over the years. If you asked them what their impressions were of me, they would say the exact same thing which is that: I learned a great deal, I worked really hard, I understood the difference between settling and never settling and we extend this to every single person who we engage.”

“None of these people will ever say anything other than I am ridiculously insistent on a standard of performance that is always a raising bar and they also will never say that I sat back and watched. They will say that I was the first one over the raised bar and it may be unrealistic to expect that everybody will do that. We don’t settle, we do it the right way 100% of the time and if you really live by that, either they will quit or they will drink the Kool-Aid and most of them drink the Kool-Aid”

“Over the years I have a presentation that says “Make Room for People” and what it says is that if you want to build a series of successful companies you will be kidding yourself if you think they will all be in your image, that’s just a bad strategy. You have to get people who are just as crazy as you, and you have to get other people who just want a really good job and people who want to go home at the end of the day and don’t take it as a mission. They both bring a set of different talents and skills and you need them all, no question about it. If you try to have everybody be Type A crazy people you will drive yourself crazy and that is not important for success. That is a huge difference. It took me a few years to learn that and it also took me a few years to really understand what the value is of having advisors, boards and investors.”

CALLING CHICAGO HOME SINCE CHILDHOOD, Howard has yet to find another place in the US that can produce the all around quality of life he has here in Chicago.

“I’ve lived in Seattle, Miami, New York, spent a huge amount of time in Texas, but Chicago has always been the place that I thought you got the most bang for your buck. It is the most workable and livable city I have lived in. I have friends and employees in New York and Seattle, but it’s catastrophically expensive just to live every single day and it’s a struggle. There is no quality of life associated with that.”

“Chicago is also unique in that it has never had to re-invent itself. It has always been a multi-pronged city. It wasn’t Detroit, it wasn’t Hollywood, and it wasn’t Cleveland which were essentially one-horse towns. When people say to me why are you here with an entertainment school – guess what? Half of my kids are going to go work for McDonald’s and CPG companies, and employers. This isn’t the film capital of the world, but it may be one of the media hubs of the world and maybe one of the technology hubs of the world.”

“For our kids and for our student graduates, this is such a better market than to be on either coast where you have 10,000 kids sitting at Starbuck’s wondering how they are going to get their resume in the door. Believe me, I’ve never felt that I couldn’t go or be anywhere that I needed to be. I have never felt constrained for opportunities.”

A JUVENILE BUSINESS IDEA WITH POMPEII-LIKE REPERCUSSIONS gave Kevin his first lesson in business ethics.

“I was about 11 in 1980 when I made my earliest foray into business when Mount Saint Helen erupted. For some reason, my friend and I got the idea that we could sell this volcanic ash as a souvenir. The trouble was, we were here in Illinois so in order to get the ash, we had to substitute the Mount Saint Helen ash for the ash out of our fireplace. We got a couple of mason jars, scooped up some ash and started pounding the pavement around the neighborhood trying to sell this bogus ash for $5 as souvenirs. One guy actually bought a jar. I think he just did it because he felt sorry for us, but we were so happy. That night, after reflecting on what we had done, I felt terrible. I woke up in tears and I told my friend ‘This isn’t right’, so we went back to the man’s house and gave him his five dollars back and fessed up. I don’t remember what his reaction was but needless to say it was all a poorly thought out, crazy idea. That was my first attempt at entrepreneurship. But then when I got into my late teens, I began percolating new business ideas, legitimate ones.”

A MILITARY BRAT TINKERING WITH HIS FATHER’S TECH-FOSSILS sowed the seeds for Kevin’s fascination with creating programs straight from his imagination. Kevin was born in Panama City, Florida. His dad, a retired Air Force sergeant turned computer technologist moved his family to Illinois to work for the “Google” of it’s times, Bell Labs in the late 1970’s.

“When my father was working for Bell Labs, they were busy inventing the UNIX operating system amongst other things, and for me a couple of early defining moments besides moving around a lot was eagerly watching my dad bring home his very early UNIX terminals on the weekends. He would bring his computer home, which was a keyboard with thermal fax paper and telephone modem. He would plug the handset of the telephone into it and type away. The output was basically burned onto the thermal fax paper. I would sit there on the weekends and he taught me how to program, how to write simple shell scripts and how to write simple C code. That really sparked my interest in software and technology.”

While some of Kevin’s friends were disassembling and reassembling TVs and radios, Kevin was living in a fantasy world where anything was possible.

“I wasn’t much of a tinkerer. But programming really grabbed me and now I was tinkering in a medium I was very comfortable in. Once I discovered the code and the software medium, I just became absorbed in it. I was able to create my own worlds just as a writer would create new worlds in a novel. I was creating worlds through these games.As a software programmer, you have complete control of your world, which is true even today. It’s one of the biggest attractions I have to software. Everything else in the world you have very little control over or it may feel at times that you have very little control over what’s going on, but damn it, that computer does exactly what I tell it to. For a lot of people that is a very alluring attribute.”

Looking at an early computer was like looking at a blank canvas with a foreign palette and paints to match. Kevin’s imagination was high jacked by one of the first video games created with this new medium.

“Cutting edge computer technology up until that point consisted of keyboards connected to thermal fax paper powered by metaphorical diesel engines operated by pull strings and kick starts. So, when I went to my dad’s office I saw the code magically appearing on a CRT monitor. Then he showed me a game, something called Star Command, where you pilot a space ship represented by an “=” sign around the galaxy and the stars were represented by “*” asterisks. I became infatuated with this game and I started teaching myself a little bit about programming to the point where in 1983, I saved up $419 (a lot of money for a 13-year old) and bought a TSR-80 color computer which was a screaming 16 MBs of memory and a little cassette tape deck for storage. By the age of 13, I began to build my own video games.”

CREATING A BUSINESS WAS ALWAYS ON KEVIN’S RADAR, but for the most part, it was a trait unique to him.

“My parents were not entrepreneurial at all. Only my grandfather on my mother’s side was an entrepreneur. Back in the 1930s and 1940s, he worked as a crop duster in Louisiana and built a small county airport. He also had three or four fishing/crabbing/shrimping boats down in the Gulf of Mexico, which made him the only entrepreneurial influence I had.”

As so many military children do, Kevin moved frequently from state to state growing up. Looking back now, he can see it helped him hone the very skills he uses today to grow companies.

“When you are moving from state to state as a kid, you learn very quickly to leave the friends you’ve made behind and move on to the next town, go to a new school, and start the process all over again. It is a very unique aspect of military life that at the time was very confusing, but now as an adult, as a business owner, it really helps me to successfully make new relationships.”

AT 19, KEVIN DECIDED TO COMPOSE HIS FIRST PROGRAM THE HARD WAY because it meant working on an IBM 80386 machine or 386, a creature from the Jurassic period of personal computing. Kevin’s first business, called Bay Area Billing, was created around an invoicing program.

“We were living in the San Francisco Bay area at the time. It was a program that small businesses could use to keep track of accounts receivable. It didn’t tie into any accounting system. It was basically a table that stored client information like name, address, invoices, line items and so forth. But the cool thing was that it printed out very nice looking invoices on dot matrix printers, which at the time was hard to do. That was my first attempt at a real business and it failed miserably because I couldn’t sell it. I just couldn’t figure out how to do the business side of it.”

Many entrepreneurs take a break after a business failure to collect their thoughts, repair the financial damage, and find whatever the next thing is. Kevin decided to throw his life in a completely different direction and the next six years were a roller-coaster of changes.

“I went into the Navy, served on a submarine for four years, broke my leg playing rugby, got out and went to college. I got married to my wife while she was going to San Francisco State. When she graduated we moved back here and I went to DePaul and got a degree in economics and started building websites.”

WHILE IN COLLEGE KEVIN DECIDED TO SWITCH MAJORS, WHICH WAS MAJORLY SMART for an already seasoned programmer needing the knowledge of economics to level up his next move in life. Kevin wanted to beef up his brain to aid in the creation of his next company.

“I started off as a business major at DePaul and I took macro economics. I was really taken with the concept of supply and demand, and the applied mathematics of figuring out efficiencies, minimums and maximums. It just seemed like a real interesting tool, so I switched my major to economics and I didn’t study computer science because I felt like I already knew what I needed to know.”

As a college kid, he made more then just pizza money after he launched his second business, ‘Chapter One Books’. It was a primitive online bookstore created with HTML and featuring a Maker Pro database with a website coded in CGI Scripts and written in C.

“We would basically export our inventory to flat files and then we had a Cron Job that would pick up the text file and update our inventory on the web. Then when somebody ordered a book, it would decrement the inventory by one in the Filemaker Pro database. Later that day, we would go through the process again, which meant our inventory listings on the web were always out of date. We thought we were so cutting edge. This is late 1995 or early 1996. At its peak, it was generating $1,000 to $2,000 a month. When you’re in college, man, that’s great. I was building websites, too.”

A MODERN GIANT PLACES AN ORDER with Kevin’s little bookshop. In the early days of web entrepreneurship, you never knew whom you would bump into. Even the heavy hitters of today began as little startups that just kept on growing.

“Occasionally other bookstores would order from us but then we started getting orders from this company called ‘Amazon.com’ and we’re like, ‘Who are these people?’ Amazon ended up ordering more and more books from us and ended up being our biggest customer during the three years that we ran the company. To us it was like a part-time job. Amazon was just buying a crap load of books from us. I only dealt with their purchasing people. Who knows what could have happened, I could have been buddies with Jeff (Bezos).”

“But it was still a really scary time. Companies were boarding up their doors and jobs were vanishing into thin air. Any start-up between 1999-2001 that existed before 9/11 that has managed to survive today, have probably seen the toughest times they will ever see in this country. It says a lot as far as tech goes. To make it through that, it says a lot about those entrepreneurs because most people didn’t make it. At that point my wife turned to me and told me I had to get a full time job.”

“So I got my first real full time software job as a C++ programmer in early 2000 at a little dot com called ‘Honesty.com’. At the time, anyone who could spell his or her own name could get a programming job. I worked there four months, four crazy months. They got bought out after my fourth month and basically eliminated most of the Chicago jobs and moved the operations to Silicon Valley. But at least I got a big $10,000 severance check. I was like ‘Wow, let me do that again’. Soon after, I got another programming job at ‘The Pampered Chef’ which was a very large consumer products company. I was one of their lead developers and we grew the team there from about six people when I started to maybe 18 when I left. I learned a lot when I was there and they were good to me. They had a 50,000-person sales force distributed across maybe four countries.”

YOU CAN THANK DIAL-UP CONNECTIONS AND EARLY VERSIONS OF WINDOWS FOR OBTIVA EXISTING. At The Pampered Chef their sites were served from such dilapidated systems before Kevin arrived. This was how business was done in cyberspace, but he wanted to change all of that.

“We built a brand new cutting edge rich client application (an application with limited connectivity to a central server) for The Pampered Chef to manage orders and a very comprehensive website with online tools for all their sales people to communicate. That is where we started using ‘Agile Practices’ both on the development side and on the product management side. After I worked with them to help bring on these Agile Practices, I decided that I wanted to do that with other clients. I wanted to teach people how to use these software development techniques and plan their software projects successfully. So I quit and started Obtiva. I revisited the Pampered Chef and pitched Obtiva’s services to their VP of IS and they took us on as our first client.”

“So my first idea about Obtiva was creating a very small specialized team of fire jumpers who could drop into this big mega corp’s software development team and whip them into shape over the course of a couple of weeks or couple of months, then we would pop out and go onto the next engagement. We wanted to teach them good developer practices and how to manage a project well.”

“I was on my own at this point in the game. I thought I didn’t need a partner. I had the clients and I could hire the employees. What I didn’t have was the cash. I started the company with $1,000 and as soon as I started hiring those employees I learned about cash flow and the fact that employees expect to get paid every two weeks and clients don’t until the net thirty terms that they’ve agreed to. So the first three months I had to go up to their accounts payable department and beg to get paid early. Luckily, they were awesome. They paid me two weeks early for the first three months – every invoice cycle. I would go up there and say PLEASE and they’d advance me the money each time. That got us through those first three months and after that we finally had enough excess to cover our cash flow needs. “

“Soon I realized that having the right partners can be a tremendous asset that gives you someone to lean on. You’re in it together and you don’t feel so isolated. I tell people one of the best business decisions I ever made was making Dave Hoover my partner. I think it was August 2005 when we incorporated and we had a big client right out of the gate. Things started to fall into place, but we needed more than one client.”

LIFE WAS LIKE A WHIRLWIND from August 2005 to September 1, 2007 for Kevin’s budding company. Working on little sleep, “spare time” was a term Kevin just wasn’t familiar with.

“I was writing code 40 hours a week and running a business the other hours of the week. My office was at Panera Bread so I would work with the client from nine to five, go home and see my family for an hour-and-a-half, go out to Panera Bread and work there for two or three hours. I did that for a couple of years. September 1, 2007 is the day I had just enough money to stop coding full-time and really work on my new company. All of a sudden I had all this free time to go talk to people about our services and actually check up on our clients to make sure they were happy. I finally got to do all those things you should do when running a healthy business. We really started to take off once we started doing that.”

“Around 2007, Dave Hoover and I read E Myth Revisited by Michael Gerber. He talks about the technician, the entrepreneur and the manager and how in most small businesses, the owner never gets past being the technician. So I decided I had to learn how to be a businessperson, learn about sales, and how to build repeatable processes in the company. Now I have to start being an entrepreneur and manager while still being a little technician.”

“The second big thing that really grew the company was when we hired Kat Nelson-Reid, our first operations manager with corporate process experience. She came in as a trained accountant who had run marketing and operations at a multitude of different companies. She came in and just started ripping things up, throwing out the old away, and redesigning everything from our accounting systems, to writing an employee manual defining what happens when we get a new client, to getting the information you need from the client and getting them into the billing system, setting up the time cards. All that stuff we never got around to doing.”

OBTIVA HAD ENOUGH BUILDING TALENT TO PROGRAM A VIRTUAL PYRAIMID OF GIZA, but dreaming of digital monuments wasn’t worth focusing on for them.

“We could build apps, but the problem is we needed a visionary to tell us what to build. You need a person who sees opportunities and can solve problems. The problem is we’re builders. Dave and I decided to be really good at being builders; just be kick ass at building stuff for those visionaries that we work with and let’s understand how to pull that out of them and be able to help them shape it so we could build it.”

Kevin has seen a lot of technology entrepreneurs fail, but the ones that have come out on top have one thing in common: Passion.

“We have clients who have an idea for a product and we tell them how high our expectations are of them to come with a strong vision and we’ll be with you throughout. We are a very hands on, high collaboration company.”

Basically Kevin wanted to create a company that employed a bunch of kick ass builders that wouldn’t be known for just unique software development, but also focus on developing people.

“When clients come to Obtiva, they know we are going to build awesome stuff for them. But in order to appease that hunger inside all technology people to build their own thing, we actively encourage our own people to have their own side projects. If one of my developers build an interesting prototype and he’s passionate, I will invest in his start-up and I’ll give him time to take it to market. I’ll even help mentor him, but he’s got to be willing to be up late at night working on it. Once a month we have a start-up lunch where people get together and talk about their side projects. We invite start-up entrepreneurs from the community to come in and talk to the group about their businesses and we have 15, 20, 30 people pounce on the idea which provides a lot of good candid feedback.”

Kevin practices what he preaches when it comes to working on side projects because he works on his own all the time. His current one is EventWax.

“EventWax is a really cool, simple to use online event registration tool that is very focused on selling seats for an event, whether it’s a wedding, a training class, or a conference. It makes it really easy to collect payments and manage your audience. It doesn’t have all the bells and whistles EventBrite does, but that is by design. It is made to be a great tool for the occasional event planner. The tool was actually released in 2006 in the UK by Patrick Griffiths and Dan Webb. In 2009 we were using EventWax for Obtiva’s training classes, then I got an e-mail saying they were shutting down EventWax and to go ahead and remove all my events off of it. I responded with ‘Well’, how about I buy it.?”

Chicago has been and will remain an excellent environment to grow and expand upon existing businesses. In Kevin’s case he uses the company he acquired, EventWax to organize industry conferences and training classes for Obtiva.

THERE IS SOMETHING SPECIAL ABOUT CHICAGO to Kevin Taylor.

“I have lived all over the country as a kid and as an adult. In Chicago, and it may be like this in other Midwestern cities, but there is definitely a vibe in Chicago where it is real. If you want to generalize, there is an attitude of people working really hard all over Chicago. People take their jobs seriously. I don’t know the stats, but I would guess they tend to stay at their jobs longer. It is a really solid city and work force.”

“So what does that have to do with technology? What I mean is, in California people are chasing funding. At some level, getting funded is considered an end in itself. Chicago is different. People are starting real businesses that they want to make profitable. They hire people who are really salt of the earth. I come in and work my ass off. It makes me really proud to be in that type of environment. It’s interesting to see that now we are starting to see some high profile technology start-ups. I teach a technology entrepreneurship class at DePaul for their computer science school, which has been a lot of fun. I like to have six guest speakers come in and just talk about where did the idea come from, how did you figure out that the idea was a real opportunity versus just an interesting idea.”

“I love what we are seeing in the last four or five years in Chicago. I like to call it ‘the Chicago School of Entrepreneurship’, which encourages the practice of creating a real company, working really hard, and making it a success.”

“When I was growing up, I was the type of person that if there was something I wanted to do, I figured out a way to make it happen. I remember my church hosted a trip that lasted three days and they didn’t tell you where you were going. It was $300, but that was just too much money for my mom. They gave us the option of being able to raise the money with a candy bar fundraiser. I sold so many candy bars, more than anyone had ever sold in the history of the church. I didn’t sell enough to cover my trip, but they were so impressed with my saleswoman-ship that they got the pastor to donate the rest of the funds, so I got to go for free.”

That kind of chutzpah helped inspire Desiree to start a business later in life. But before a business can be created, one must come up with an idea. Desiree created GiveForward with co-founder Ethan Austin and $5000 in angel investment money from her late grandfather, to streamline the online fundraising process to help those in need while maintaining a viable business model.

A COSTA RICAN GAL FROM HUMBLE BEGINNINGS, Desiree was born in Escazú, Costa Rica, a suburb of San Jose. Her will and strength were forged at an early age.

“I was dying to study in Spain when I was in high school. I applied even though I knew we couldn’t afford it. I was eligible for a scholarship, but wasn’t going to know till the very last minute. So my back up plan was to apply to all these community centers and small non-profits that gave out money in case the scholarship didn’t go through. I scraped together enough money and I worked my butt off. Between that and working a job putting together urinalysis kits for drug tests, I made enough money to go on this trip for a month. I think that is entrepreneurial behavior.”

DESIREE’S ROOTS AS AN ENTREPRENEUR came from butting heads with her grandfather. “My grandpa played an important role in my life. I think he was very much a men-rule-this-world-type of guy and I liked butting heads with him a lot about things, so he helped me to be driven.”

Though Desiree never took her grandfather’s old world stereotypes to heart, the fact remains that women are in the minority when it comes to pioneering a business in the US. This statistic coupled with her head butting sessions with her grandfather was something that Desiree always kept in the back of her head, but never let it deter her.

“I think men have a better way of dealing with the anxiety that comes with having their ego married to their business. They think, ‘Yeah, it’s my company, this is my ego and they are tied together.’ I think women are a little more sensitive about it. But what I have seen is strong women starting companies in Chicago. We are all fighting so hard to make a place for ourselves among the men who are doing the same thing. I don’t want to be known as a woman entrepreneur. I want to be known as a successful entrepreneur.”

“Also, how do you ride the line without coming across as a bitch when you are just trying to be a decision-maker? How do you talk to male employees who are actually older than you are and who consider you to be less experienced than their last boss? I am excited that there are so many more women coming into the spotlight. I think Excelerate (a Chicago based incubator) did a lot to help. That’s very rare for an incubator and I hope that continues to happen. I hope that we can figure out a way to help each other and build a network that is maybe a subset of BuiltInChicago. (a resource for “digital professionals” working to build web and mobile businesses in Chicago)”

GETTING A GOOD EDUCATION WAS A MANTRA IN DESIREE’S UPBRINGING. She knew it was the only way to level up in this world. Growing up with less then most of her classmates meant that she needed to snatch up every possible opportunity, whether it was a scholarship, a study abroad experience or an unpaid internship. Desiree’s upbringing made her painfully aware of the limitations that are organically placed in front of you without a solid education.

“My mom didn’t finish school until I was in school, so I grew up learning that if you don’t go to college, your life is going to be a lot harder. Getting into college was always my priority and I was working really hard in high school. I only played hard on the weekends. But I thought once I got in, basically I was done with having to work hard. That sounds so silly to think that now.”

FOR AS LONG AS DESIREE COULD REMEMBER, she dreamt of going to Georgetown to pursue international studies. But after one visit to Yale, coupled with a desire to be with an “edgier crowd” the decision was clear: Yale. But how to pay for it?

“I decided to write a letter to the Admissions Office at Yale saying I really want to attend, but Princeton made me this offer that was pretty hard to refuse. I got a letter back saying that they would match the offer, and I was eligible to take advantage of a unique scholarship program, so I took it.”

After graduation, Desiree was tested again. When she couldn’t afford to take an internships in big cities like New York or Washington D.C, she instead had to take an unpaid internship back in Kansas. It was during this internship that her future began to reveal itself.

“I couldn’t find a job so I was waiting tables in Kansas City at a bar and grille. I ended up waiting on this guy who said he worked at the Kaufman Foundation (an organization that educates, promotes and connects entrepreneurs) and that if I gave him my resume he would see if he could help me get it to the right person. I gave him my resume and he said it was terrible. He helped me fine-tune it a little bit. He circulated it and it ended up on the desk of this woman named Judith Cohen who was the Vice President of Entrepreneurship. I didn’t know it at the time, but the guy who had my resume just scheduled meetings for the Conference Center. He had no clout at all, so the fact that it got into her hands was pretty incredible.”

“She gave me this job that didn’t exist at the time: being a specialist in collegiate entrepreneurship. I didn’t have any responsibilities. I was just kind of her right hand while she was building this program called the Kaufman Campus Initiative. The whole point was to help non-business school students recognize entrepreneurial potential. It was about teaching students how to recognize good ideas, conducting feasibility studies and seizing entrepreneurial opportunities. Whether it’s about getting to be student council president or marketing yourself in the right way to get the job you want at the company you desire, an entrepreneurial mindset can push you forward in a lot of different areas of your life, even if you are not actually starting a business.”

A BORN BUSINESSWOMAN ON A MISSION, Desiree knows that it is so easy for startups to become set back by defeat, whether it’s investors falling through or facing personal financial hardships. What separates the businesses that fail from those that succeed is owning the fact that you’ve only failed if you quit. Startups need to see the difference between a roadblock and the end of the line. That is why the percentage of failure in the startup world is so high, especially in the tech business, where a virtual graveyard has been formed by great domain names without a site.

“It is a hard thing to quantify and at the same time it is really important to teach people that the don’t need to get a job at a big company so they can rise, rise, rise. As a 22- year old you can step outside of that mold and consider start-ups as a great place to learn as much as possible. They can learn so much that can be applied to another job or to their own company. That was a big part of what the work was like while I was there, and I got bitten by the entrepreneur bug.”

“My contract was coming to an end and I decided to move to Chicago where my boyfriend was living. The relationship ended up not being a good fit but it was a big life-learning lesson. I think when you grow up without money and you meet someone who is very comfortable and well-off and is willing to take care of you, it is easy to think ‘I’ll give this a try’ but ultimately you have to go with what makes you happy. The relationship didn’t work out, but it was the start of a new chapter in my entrepreneurial life. I’m glad I learned that lesson at 25 instead of 35.”

GiveForward is a web-based business that empowers donors to generate financial support for friends and family in need. “I had the idea for GiveForward before I left Kansas City. We were talking about Hurricane Katrina and complaining about how we were forced to give to a charity through our paychecks without knowing where the money was going, especially when you know that 40% is going to overhead. I don’t really have a problem with non-profits using money for overhead when they don’t have super-inflated salaries and they are smaller, but at the time it seemed so ridiculous that an employee is forced to blindly give “x” amount of their paycheck without control over the money’s destination.”

“I remember talking about how great it would be to give directly to families who were affected by the hurricane. This way we would have a greater sense of accomplishment and we would feel connected to the recovery in New Orleans. At the time we were disappointed that there wasn’t an easier way to give directly to the people. That got me thinking about the role of small-scale donors and how they really are the backbone of American philanthropy, but they don’t have much of a say in where their money goes. I was thinking how there should be a better tool.”

But how to go from point A to B?

“One thing I learned from Kaufman was that a lot of entrepreneurs make the mistake of thinking that they have to hold onto their idea tightly so no one else will steal it. But really what they should be doing is telling everyone so others can help.” It was painfully obvious to Desiree that networking and sharing war stories while trying to breathe life into a start-up was simply the right thing to do. Desiree became a sponge for information as her own startup began to take shape.

THE CONCEPT OF GIVEFORWARD coalesced during a trip to Costa Rica.

“I put even more thought into what GiveForward could be. I had already named it GiveForward in my mind because of an idea I had heard from an entrepreneurship professor. He was talking about the current generation of entrepreneurs needing to give forward to the next generation not by giving them money, but by giving them expertise and teaching them how to succeed. I had never heard the words ‘give forward’ put together before. I started to think about it in terms of small-scale donors: if people gave small amounts of money throughout their life versus waiting till after they died, they could create a bigger impact. I was trying to think of it as the opposite of ‘giving back’. So in November 2007 I bought the URL for GiveForward. Now I had a domain name, but what was the business going to be?”

“One night I woke up to this little voice inside my head telling me just to get started. I sat down in front of my computer and I wrote out this three-page executive summary about how this company would be a donor driven site that created a way for donors to feel connected to projects around the world.”

“I sent that three-page write-up to a professor at Northwestern whom I didn’t know, but was a part of a small business clinic inside their law school. I asked him how I could launch this company. He wrote back the next day and said, ‘If you are half as good at selling the concept to others as you are at presenting this idea to me, you are going to be a great success.’

“After hearing words like that, I was inspired to launch our company. So with my business partner Ethan, we launched with a Mardi Gras-like celebration targeted to sororities and fraternities, long distance runners and small non-profits. We hired cute interns dressed in GiveForward swag to give out free hugs and beads to them. Then in March 2009, a girl named Amy Cowan came to our site because she needed to raise money for her sister’s kidney transplant. Her sister had maxed out her coverage when she had a heart transplant at 10-years old. Amy had some previous experience with fundraising, so with the help of GiveForward they put together a 24-hour Facebook campaign that helped them raise $30,000 and get their story into the Chicago Tribune and USA Today.”

“From that experience we discovered is that our brand lent itself so well to medical space, and we decided to focus our attention just on medical fundraising. Before we were trying to service all types of fundraising, but we learned that without a focus, it is hard for a small company to grow. When we focused, we started to see a real change in our SEO and the type of people coming to our site. Word of mouth was strong with medical fundraisers, and we were getting a lot of referrals from other fundraising organizations. Nurses really loved what we were doing. Patients really loved our blogging tools and how we looked more like a patient blog site with a fundraising component. In March 2010, less than six months after we started and on the birthday of my late grandfather, we hit our first million dollars in donations.”

Today, GiveForward continues to grow into a successful business that generates revenue for the company while providing a noble service to its users. Recently they closed on a $500,000 round of funding as well to further boost their growth.

“I feel like we are in a really lucky place because we are helping people give to others without much donor fatigue. Our goal for 2011 is to be the number one site that people think of when a friend is in need. I think we can do it. I think we might be getting close to being that site.”

“I started my first company my junior year at University of Illinois. I studied mechanical engineering and looked forward to my senior design project where you actually got to build a product for a corporate client. As it turned out, there wasn’t enough corporate involvement my senior year and I was asked to do finite element analysis of the car designed by the Society of Automotive Engineers. This was a pretty crushing blow but I channeled all the energy I would have poured into a new product development project for a major corporation into starting my own company, LeverWorks, instead. Lever Works had 3 offerings custom web software, hosting services, and off the shelf web software products. In December 2001, 6 months after graduating and a year and a half after starting the company, it was bought out by LeoMedia. The next month we went to Disney World to celebrate.”

“As a college student, owning that consulting company was exhilarating. From running it, I learned that when you are selling your time it is very hard to scale. Although our rates were relatively inexpensive compared to the big 1,000+ person consulting companies offering website development the profit of the company was directly proportional to the number of hours we could bill to the client. It was hard to grow that kind of business because revenue was directly coupled to our time.”

ZACH LOVED BUILDING THINGS while growing up in Northbrook, Illinois. He often dreamt of becoming an architect and would draw his future house. He would build elaborate roller-coasters, go-carts, and robots with parts from Lego kits without any instructions.

In grade school, his earliest entrepreneurial memory was selling special markers he had bought and modified so that his fellow 4th graders could blow in them and spray marker ink everywhere. That experimental spirit stayed with him through the years and being as resourceful as he is, when Zach first arrived in college he would once again find himself selling a unique product to make a little extra pocket cash.

“My sophomore year I was selling the cell phone from the movie The Matrix on e-Bay. I would order them in bulk from Europe and then sell them on-line in America. The funny part was the phone didn’t work in America and we clearly stated that on the posting. Our customers didn’t care, they were huge fans of The Matrix and just wanted the phone from the movie because it was the first phone to shoot out. At the time the phone was a coveted collector’s item and since they weren’t sold in America if you whipped it out people’s jaws dropped. I think we were buying them in boxes of ten or twenty for about $50 or $70 bucks each and we were selling them on e-Bay for $350 or $400. It was a time-sensitive arbitrage because obviously the sheen of The Matrix faded off and so did the little business.”

BEING AN ENTREPRENEURS WAS IN ZACH’S BLOOD. Both his grandfathers owned their own companies; one owned a custom electronic transformer business and the other owned a soda pop bottling company. So when Zach was graduating college, he told his family he wasn’t going the traditional corporate job route. Their reaction was, “Whatever you want to do.” They were even one of his first angel investors in his next business.

After the success of LeverWorks and the trip to Disney World, the seeds for Zach’s next company, Inventables, were planted. First came the name Inventables, which was invented in a brainstorm before the company was even born. Zach and his business partner at the time thought it was the perfect name to represent the energy and the “anything is possible” attitude they wanted to capitalize on.

In essence, Inventables is an online hardware store for R&D professionals. They sell materials and technologies to folks doing product development. The company has create a giant online catalog that includes materials for laser cutting, machining, and molding but also some inspirational and highly specialized materials; things like translucent concrete, gel magnets, aluminum foam. The company switched to its current business model of an “Innovator’s Hardware Store” in late 2010 after working exclusively as a subscription service for the past nine years.

“We wanted to change our business model to be more accessible to ‘the little guy’, not just Fortune 500 companies. Now we can service a one-person company, a start-up, or multi-billion dollar company. Customers regardless of size can go to the website and order any of our products with a credit card.”

While the company may be highly successful today, they got off to a rocky start.

“We started out by interviewing potential customers, mostly industrial designers and engineers in big companies and consulting firms that worked on product development. We wanted to understand how they learned about new materials and how their process went from inception to a product on the shelf. I think after 40 or 50 of these interviews, the idea for Inventables started to evolve.”

“Then we hired a team of five interns one summer and set up office in Urbana. During our pilot program, we built three of what we called ‘innovation centers’ – a library of our vast collection of products – and traded three months free access to the library in exchange for customer feedback, mostly from the three major consulting firms who designed products for all the Fortune 500 companies. It turned out the customers all told us they thought our product was awesome.”

“In the final meeting at the end of the 3 months excited by their positive response I asked, ‘Would you pay $2,000 for it?’ They said, ‘Absolutely not.’ I was devastated.”

“Hearing that we had an awesome product juxtaposed to ‘But we’re not going to pay for it’ was gut-wrenching and confusing. I remember being in a meeting with a consultant and getting glowing reviews and thinking, ‘Oh, my God, we’re going to get our first order!’ And they were like, ‘We’re not paying for this.’ We knew our idea was great, but the feedback was very hard to understand. We didn’t know at the time that consultants didn’t really have budgets to do material research because they were just being hired by a client. Lucky for us after rejecting us one of them introduced us to a client of theirs and after hearing our pitch the client asked to place his order before we even had the chance to discuss price with him. We thought, ‘Whoa – who is this guy?’ It was a roller coaster of confusing emotions, but once we realized that it was the clients who were our target, things started to take off.”

LIKE SO MANY OTHER START UPS, Zach and his partner started out by working out of their apartment with no office rent or staff to pay. But they already had their first order two months before officially launching the company, and started generating revenue right when they launched around November 2002. They saw that they were onto something in March of 2003 when their customer base started growing.

There seemed to be an insatiable curiosity and demand for new materials because of a need to innovate for the marketplace. A huge percentage of products are commodities, so how a brand can differentiate itself in the marketplace sometimes comes down to materials or design. Once Zach and his partner realized this, they started to feel much more confident in the business model.

“We scoured everywhere for interesting materials: trade shows, the Internet, trade journals, even cold calling vendors. Most vendors thought it was really interesting and a novel idea – they had never heard of it before. We were offering a unique product: a subscription similar to a magazine to a vast library of materials that could help differentiate a new product. On top of that we had fun ordering all the materials, photographing the products, writing the articles, and shipping out the catalog.”

Even though the customer base was growing quickly, Zach took protecting his company’s vision and not losing control over the company very seriously and he waited years before looking for outside investors to further expand.

“I waited six or seven years before raising an institutional round of financing because I wanted to figure out the right business, the right way to approach it, and be sure to stay true to the vision. In the early days when I would speak to investors I was not able to articulate the vision well enough. Investors always wanted to change the business so I felt that if we took money before we were ready, we would risk being directed in a way that wasn’t aligned with our vision.

I grew up with the company. After about 5 years I bought out my co-founder and re-focused the team on why I started the company in the first place – to help companies innovate. Over the next two years the company grew 50% a year and we hit record revenue levels.

“At this point I looked for investors because we were at a point where we had built up the brand and the clients, we were profitable, and I was ready to take it to the next level. I thought the best way to grow was to leverage the Internet. When we first launched our company, the primary way customers found materials was by calling vendors they worked with or talking with their friends or peers. Six years later, the primary ways they find materials is Google. Eventually I took some investments from TrueVentures to scale up the business.”

HELPING OUT THE “LITTLE GUY” is fundamental to Zach’s life. It’s obvious that he has deep seeded sense of duty to all the inventors out there; to all the geeks, nerds, tinkerers, techies, hackers, builders, and scientists. Zach wants to help you build incredible things.

“We support anyone who wants to go out there and tinker and explore, and we’re working to make our resources more easily accessible to small business owners, students or inventors. And I’m excited about that!”

“In late 2010 we launched the innovator’s hardware store in an attempt to democratize access to the tailored library of materials we sold to our Fortune 500 customers. With the library subscription if you were working on tools, you could get materials related to tools. If you worked on shoes, you could get materials related to shoes. As the years went on customers wanted the materials we showed them to be even more specific. We responded by putting everything online in the hardware store and working on software that gets “smarter” the more it is used. The more our website is used, the more it will show you things you might find useful. The response has been tremendous and we continue to work on ways to make product development inspiring and easy to do. Our software engineering team is working on some exciting things that will launch next year.”

“We also host a lot of usability tests so designers, engineers and entrepreneurs who are building stuff can come to our office and share their experience of how they found their materials. We love meeting these folks. I want to start telling the stories of what they’ve done with these materials in a more meaningful way. We have so many great stories. It’s even inspired me to start building a few things of my own.”

“In the long run, my dream is that we make the site so easily accessible that you can find anything yourself and don’t need our concierge services. We are working on embedding our concierge capability into the software and the site itself, making it more collaborative so it learns what you are interested in, and connects you to other folks that can help you overcome obstacles.”

EMPLOYEES AT INVENTABLES DON’T WORK, THEY EXPLORE. Zach has been very mindful of how to maintain the innovative work culture that has helped his business grow and keep’s his customers so happy.

“We’ve put a lot of thought into keeping the culture the way it is. We have what we call Five-Minute Madness every Thursday where we buy lunch for the employees and they shares their updates on what they’re doing or put on a demo for us. We have Free Point Friday where every Friday the technical folks work on whatever they think is most important – no questions asked. We have an innovation budget that our employees use to build a product. This gives them the opportunity to experience what customer’s experience. It puts everyone in our office in the customer’s shoes and forces them to bump up against the same struggles a customer has doing their job. Every morning we have breakfast catered so we can socialize, get to know each other, then hit the ground running with work.”

“The work we do demands a lot of creativity from the people who are involved. That means they have to be given a chance to explore, try new things, and feel comfortable with stepping outside the lines. I find that when people are happy and like each other, they’re more likely to collaborate and come up with new ideas and work together on things beyond what you ask them to. If this were a more ‘traditional, corporate-punch-the-clock, go to your cubicle, type up your reports’ type of environment. If we had that, at best we would get exactly what we asked for, as opposed to that extra special something that you can’t ask for that comes from inspired employees.”

ZACH WANTS THAT “EXTRA SPECIAL SOMETHING” FROM EVERYONE, not just his employees. To get Chicago excited about innovation and disruptive ideas, Zach co-founded with Brian Fitzpatrick of Google Chicago, an invite only, two-day weekend camp every year called ORD Camp. The event includes some of the most well-known and interesting people involved in technology with a strong focus on the Chicago community.

Zach was invited by the Museum of Science and Industry to sit on the advisory committee for the Fast Forward exhibit. This exhibit showcases what modern day innovators are creating in the world in an attempt to keep the museum at the forefront of science and industry.

Zach wanted to contribute to the Chicago startup community, with the same kind of great mentoring he was given growing up and through college.

“I also got involved in Excelerate Labs because through their events I met people who were genuinely excited about what they were doing, unlike other networking events where people were just trying to find investors or the next customer. And as someone who had been running a company for a while, I was happy to share my lessons learned.”

And Zach isn’t done by a long shot.

Zach is also involved with the Technology Entrepreneurship Center, a new department started at the University of Illinois, along with 120 other companies. They help students start their own companies. In the last year he donated an Inventables material library formerly sold for $70,000 each to 10 Universities. The donations went to schools including IIT, U of I, UIC, Stanford, MIT, Carnegie Mellon, RISD, and a few more. “We chose Universities that are striving to grow their programs in the fields of industrial design, engineering, science and technology. We believe these programs will be responsible for the future growth of our country’s economy and the main source of people that will improve the quality of human life.

A WORLD FULL OF INVENTORS tinkering in basements, bedrooms, and garages is the future Zach wants to be a part of and he is determined to have Inventables play a leading role in that revolution.

“I’ve poured my whole adult life into this business and I’m encouraged by the progress. I think there is a compelling, interesting idea that is driving this business I see customers respond to. I’m excited to help private developers all over the world get access to materials to build and realize their dreams. I think democratizing access to materials for prototyping and R&D is a really powerful concept. I love sharing our inventive spirit with everybody in the world and watching what new products folks create.”

“The online hardware store has provided a scalable platform for Inventables. We’re really starting to put our foot on the gas and grow. So far the results have been encouraging but as we know from past experiences, being an entrepreneur can be a roller coaster ride filled with higher highs and lower lows than a traditional corporate job.”

“In business schools and in business plans, they ask for exit strategies,” Leitner says. “I find that absurd. What I’ve learned at every stage in my career is that I learn more on the first day of doing whatever it is I’m doing than I will ever learn by planning for it.”

There have been quite a few “stages” in the winding, wending career of Leitner, founder of the Insight Labs. From military school to journalism to working on a kibbutz to working in social work and politics, his life experiences have trained him for his current passion, Insight Labs, which focuses on one thing: solving the toughest, most meaningful problems for non-profits and government agencies.

Growing up in Texas, he didn’t regard himself as a trouble-maker — or trouble-shooter — but problems always seemed to sprout up around him.

“I was the guy who never overtly did anything wrong, but things seemed to be going on. I seemed to be orchestrating them. My version of being a pain in the ass was just orchestrating larger movements that were pains in the ass.”

He was a “mostly smart kid,” played a little sports, dabbled in student government, but was mostly trying to over-achieve academically. He never grew up to be terribly tall or athletic, so “it was the only card I could play.”

After military high school, he went to the University of Texas to study government because of “my fascination in how big systems worked, like legislatures and constitutions.” He joined a fraternity and became involved in student government.

“We held the first campus-wide elections after they were banned in the 60’s due to riots. The student body, in its collective wisdom and in appreciation of the administration allowing ‘student government’ again, elected a cartoon character as its first class president.

“It was a heady time.”

AFTER COLLEGE, THE ROAD LEITNER WAS TRAVELING ON TOOK ANOTHER TURN. He ended up doing social work at a psychiatric hospital for adolescent girls for over two years. It was an introspective time for Leitner where he studied himself as much as his clients. He also saw it as his own version of the Peace Corps.

“Standing where I stand now, I start to see threads,” he said. “I seem to be going down this pretty conventional frat boy, government, law school track and then suddenly turning and being a social worker. My friends could not figure out what the hell I was doing. Nobody understood what I was doing. If you talk to people in social work or psychiatry or psychology, there is a recognition that you have to be a little nuts to do it because it helps you sort out whatever you are trying to sort out. There is a deep, deep, introspection involved in any of those jobs “

Then another life change occurred, all because of a movie:

“I saw ‘Broadcast News,’ this great movie about broadcast journalism, and loved it. I decided at that moment I was going to grad school for journalism, even though I’d never taken any of the classes. So I researched and called every top school in the country. I finally got a hold of the Dean at Ohio State. I said, ‘Will you accept me?’ He said, ‘Alright.’ I hung up and realized I didn’t know where Columbus, Ohio was. But I gave notice at my job, loaded up my Jetta, and drove north until I got there.

“That’s how grad school started.”

JEFF COULDN’T TYPE, HAD NO MONEY, and had never taken a journalism class in his life. But his joy of taking on a challenge led him on. Through one of his professors he got a teacher’s assistant position that covered his tuition and then in a classic case of “you never know where life will take you,” Leitner stumbled into Broadcast Journalism through a classroom incident:

“I became a research assistant, which waived all my tuition and they gave me all my money back. They paid me $10,000 on top of tuition waiver. So I took the stipend and bought my first computer in 1988, an Apple MacIntosh. It had a little gray-green screen in the middle of a big white plastic thing. I didn’t know what to do with it and didn’t know anybody who knew what to do with it.”

“One day I’m in Journalism 101, and the teacher writes up some facts on the board and says, ‘Write a lead.’ I said, ‘May I handwrite it? I don’t know how to type.’ I was kicked out. That was alarming. I walked down the hall and I enrolled in Beginning Broadcast Journalism because they didn’t ask me if I could type.”

Then he threw himself into the most intense learning and working experience of his entire life:

“I finished in one year. I’d never experienced anything that intense. I didn’t date. I didn’t want any distractions. All I did was study because I wanted to drill down as far as I could. It was like being in a monastery. I wanted to watch myself think and push myself to see if I could do it and experience something as purely as possible.”

AFTER CLOISTERING HIMSELF IN ACADEMIA, Leitner did what everyone American does after college. That is, if by everyone you mean maybe 100 Americans a year. He joined a kibbutz in Israel, which could best be explained as taking share-cropping, socialism, and commune living ideals and mashing them into some sort of hybrid alternative lifestyle.

“I lived on a kibbutz doing chores half the day and taking classes the other half. I went because of the romance of it and I wanted to test my thoughts about socialism. I’m a do-good guy and I wanted to immerse myself in an experience where nobody owns anything and the Collective decides what you do for a living. It was amazing but it turns out I wasn’t a socialist. And neither were they. I found out that they kept sneaking things in, like TVs, which they would hide from the rest of us.”

Leitner can best sum up his experience living on the kibbutz with story about box-making:

“One day I am assigned to work in the factory and they ask me to assemble cardboard boxes and my supervisor says ‘I’ll be back to get you for breakfast. Please build 10 boxes.’ And he doesn’t come back for a while. So I built 10 boxes and then I built 12 boxes, and then I built 15 boxes, and then I built 20 boxes, then I built 30 boxes.”

“The guy comes back to get me and he’s livid because I’ve have exceeded my goal, which throws the whole eco-system out of whack. So it really is for each according to his abilities and to each according to his needs. That’s how socialism works. You are not in America anymore, where if I had been told to make 10 boxes and I made30 boxes, I would get a scholarship. If I made 40 boxes, I would win an award.”

“There was a cultural presumptuousness to it over there. It was as if I were showing off or saying,  ‘I’m better than everybody else.’ In the States, we admire that. We admire people who at age 15 make a billion dollars; there, it was just obnoxious.”

NEVER ONE TO PASS UP AN OPPORTUNITY FOR PROBLEM SOLVING, Leitner set out on a backpacking trip through 20 countries, only to end up getting stuck in the West Bank in the middle of the night with no money. And lost in the Alps. And trapped in a Paris train station.

“I can’t remember who said it, but they said, ‘Democracy is the worst system in the world except for all the others.’ You are acutely aware of it when you’re traveling. You’re aware of what works and what doesn’t work – all of which is really important to me now in retrospect.”

“I don’t know that I could have done the things I’ve done since or been the guy I am now if I hadn’t screwed up in those places. I once got on the wrong bus and ended up alone in the West Bank in the middle of the night and no more buses were running. There is something to that. That stuff helped me a lot. There is not a lot in business that scares me now, because that was truly scary.”

“I got stuck in the Paris train station because I didn’t know the word ‘sortie’ means ‘exit.’ I got lost in the Alps with a friend who as clueless as I was. I ran into all sorts of trouble on that trip that shrunk the world for me in a profound way that, I think, influenced my worldview.”

After getting back to the US in one piece, Leitner made crazy bet with his then-girlfriend about moving to wherever one of them got his/her first job. They both ended up in Chicago because his girlfriend landed a gig at City News Bureau. The relationship ended, but Leitner’s career in journalism began.

“When I moved to Chicago in 1990, I got a job as a newspaper reporter covering local politics. I didn’t know what I was doing, so I followed good reporters around all day. They didn’t mentor me much, but they let me hang out, which trained me in how to be a reporter and ask questions.

“Reporters are fascinating because the good ones have an amazing ability to go into a situation where they know nothing, and after researching for three hours they can clearly explain the entire story to anyone. I was very serious about learning how to do that. It wasn’t about the writing; it was the process that fascinated me. After a while, I found myself teaching the people I was reporting on about how they could position their story better.

In 1996, Leitner’s reputation for knowing how to position a politician’s story preceded him because he got his first chance to run a political campaign.

“I was hooked. I joined a public affairs firm in 1997 and for the next six to seven years I managed strategy, messaging, and fundraising for candidates running for office, as well as representing corporations trying to navigate governmental waters. It was a lot of fun figuring out how to get things done in a city where I was considered an outsider and had no power or influence.”

TIRED OF WORKING FOR EVERYONE ELSE, he set out to make his own name in the Chicago political world. No small task, even for a seasoned Chicagoan, let alone a kid from Texas.

“I launched my own consulting shop in 2003. I did it for the purest reason: I wanted to do it my way. I didn’t think about the word ‘entrepreneur,’ though I’d been around them all my life without knowing it. My best friend in college was a serial entrepreneur, though it was hard to tell since he started out by selling screen printed t-shirts out of the trunk of his car. My mom was a lawyer with her own practice, and other doctors and lawyers in my family had their own practices. But, again, I wasn’t aware that they were business owners.

“I watched several of them sell their businesses but it still didn’t compute. So when I started my own business I didn’t know I had any reference points, didn’t know what I was doing, and I had no power. But what I did know was how to solve problems.”

And that’s exactly why Clear Channel contacted him after the company failed to make any headway on an effort to put billboards on top of taxi cabs to sell national advertising.

“It was a big problem,” Leitner says. “Mayor Daley thought it was visual clutter and was strongly against it.”

Clear Channel had tried all traditional ways to get it done. They flew in the CEO to have dinner with the Mayor. They worked the commissioner. In short, they had done it exactly the way it is supposed to be done and it hadn’t worked.

“A guy I had worked with at my previous public affairs firm told [Clear Channel] they should hire me. It was very kind of him to do it and I will be eternally grateful.”

After striking a deal with the media company, Leitner had to actually figure out a way to make the mayor happy, make Clear Channel happy, and make sure everyone walked away feeling as if they had won.

“Here is how we got it done. I started poking around at something that was bothering the City a lot: taxi cab drivers would show up every few months at City Hall with placards and they would protest in favor of a rate hike because they have a pretty tough job. So I called City Hall and said I had an idea. I told them that I thought I had a way to get cab drivers more money and they said, ‘Really?’”

Leitner helped Clear Channel design a new financial model– the first one anyone had ever done that pays the drivers of the taxis who are driving around with billboards on their car.

“So, we created a model in Chicago that is now being replicated elsewhere that says when you drive around, the company who owns the taxi gets money, the City gets a lease tax, Clear Channel gets a fee, and the guy who is driving around all day gets a percentage as well.

“It solved a problem for the City. The mayor ended up championing it himself and it passed the City Council 50 to nothing.”

ALWAYS FALLING FORWARD INTO THE NEXT ENDEAVOR, Leitner finds himself with more projects than he can fulfill in a lifetime.

He and his wife launched Blanket Week, through which they collect thousands of new blankets for the millions of homeless in the US. But his biggest project, Insight Labs, was launched with colleagues at Manifest Digital.

In 2009, Leitner became friends with Jim Jacoby, founder of the creative consultancy at the now-famous 600 West Chicago building. Early conversations focused on bringing together great minds and shaking up the status quo.

“I’m a big fan of making myself the dumbest guy in the room. That’s what gets me off. That means that the longer I do something, the harder I have to make it – just to keep myself engaged.”

Insight Labs are monthly sessions, for which Leitner recruits senior corporate executives, founders and wild-cards – like artists, playwrights and physicists – for a 3-hour, full-contact strategy session to try to solve an impossible problem for a non-profit, government agency or entire industry.

“I had done work like this a few times with my first business and learned that people want to help as long as you don’t waste their time. You have to curate for talent and brains. I like to make new friends and I’m sure we do good. The whole experience is an adrenaline rush.”

There’s a waiting list for organizations that want the Insight Labs to tackle their challenges. But Leitner has strict criteria. One: The nonprofits involved have to understand that there is a value to the process. Two: They have to possess the resources to do something about it once a solution is created. And three: The problem has to be an interesting one to solve, which means it has to be interesting to Leitner, and give others a reason to get involved or “leave their desks,” as he likes to say.

“I want to solve the hairiest problems with the most interesting people. For me, the harder it is, the more exciting it is. Jim and I both say we look for opportunities that terrify us. Like the time midVentures asked if I would speak about Insight Labs at their conference, and I offered to host a lab onstage instead.”

“Or when we launched UX for Good, which is a wildly ambitious effort to come up with design-focused solutions by packing some of the most talented and creative people we can get into a room for 48 hours to solve giant social challenges.”

Leitner believes a roomful of people with different experiences and expertise in a controlled, confined space creates amazing results:

“Creativity and innovation happens when you kill politics and posturing. I also strongly believe that a single, shared vision is more powerful than an ocean of suggestions, even if the shared vision isn’t entirely right. If everyone’s rowing in the same direction, whether or not it’s a little off-course, you can win.”

When he’s not constructing and running Insight Labs, Leitner is part of a new, dedicated strategy practice at Manifest, predicated on the same ideals: very smart people, no pride in authorship and a commitment to being scared every day.

Clearly, it’s a journey without maps. Or exits.

“True,” he said. “But remember, wandering maps worlds.”

For Leitner, a lifelong sojourner, it also solves problems.