I was hatched in 1971 and raised in a middle-class neighborhood in Elmhurst, IL. My father was an entrepreneur in computer consulting and I remember growing up with punch cards all over the house. At a very early age, I was thinking about my own company when my father said, “You can go to any college you want, as long as you pay for it.” I started my first business buying and selling baseball cards along with several glamorous jobs like cleaning out an incinerator at the local grocery store, painting houses, driving a forklift at a gutter manufacturer, and a Chemlawn man to name a few. Fortunately, I made enough money to graduate from Indiana University with a degree in business with zero dollars in debt.

At Indiana, I was exposed to some great leadership opportunities through my fraternity and through the business school. I was able to leverage that leadership experience into a job with Procter and Gamble. P&G offered me amazing training and education on sales, marketing and business in general. However, after a few weeks on the job, I realized I didn’t have a passion for working with 120,000 co-workers. I understood I didn’t know much about the real world and spent the next 4 years focusing on building my skills, reading hundreds of books and being committed to doing a great job day in and day out. I was recognized with numerous awards at P&G and made a great salary but was unfulfilled.

In 1997, I was introduced to Rich Heise who was starting an Internet solution for radio stations called Magnitude Network. Rich explained the opportunity and growth potential and convinced me to forgo my six figure salary and go back to making $30k a year. However, he introduced a thing to me called equity. I dove in with both feet, worked 100 hour work weeks and in 1998 I worked 364 days that year (took off for Christmas). I taught myself as much as I could about the Internet, programming languages, development, etc all the while driving the sales engine. The original business plan called for 25 radio stations in the first year and I was able to close over 400 of them in 18 months. Shortly after, the company was sold to CMGi. Upon selling the company, I got my first equity check and lets just say, I have NEVER worried about salary again in my life.

I had a track record and technology experience and one of my old bosses at P&G called to bring me into an eProcurement/Reverse Auction company called PurchasePro based in Las Vegas. I was brought in to build the sales and operations in the central United States. After executing that, I held a number of executive level roles in the company and was part of the management team to take the company public. It was a very valuable three-year experience. I learned so much about myself and what it means to ‘go public.’ Most importantly, I learned a great deal by learning from many bad decisions others around me were making and that more than anything better prepared me for my future start-up companies.

Early 2002 brought me back to Chicago. I am a total Chicago guy and LOVE everything there is about the city and most importantly, the very talented people and their work ethic. I was able to reconnect with Rich and one of his colleagues Eric Lefkofsky. Eric was just starting InnerWorkings and he presented me with an opportunity to earn sizable equity to help grow this print management company. The company was doing less than a million dollars a year in revenue and I didn’t know a thing about commercial print. It wasn’t the world’s best business model but I learned the importance of over delivering in execution. I built a sales team with over 100 sales people, developed a world-class implementation and operational playbook and most importantly hired some of the most talented entrepreneurs on the planet. We didn’t have the Ivy League education or the big consulting background but man, did we have the heart, the passion and the overall WILL to succeed. I was always taught the importance of team but until you work with a group of folks that day in and day out deliver you truly learn ANYTHING can be achieved. In a few short years and without a lot of outside capital, we were able to take InnerWorkings public in August of 2006. In addition to all of my management responsibility, I couldn’t get away from my true passion of doing the big deal. I was the top sales person in the company by landing clients like, Circuit City, ServiceMaster and Citibank to name a few.

There were a few key events that took place while at InnerWorkings. We hired a young man, Andrew Mason, to be a computer programmer for us. I have met a lot of smart people but Andrew was one of the smartest. Since we were always frugal with our money, we were programming in a language called Servoy. No one knew Servoy and Andrew taught himself the code and recoded our entire application away from FileMaker (also very inexpensive but not scalable). When Andrew developed his idea for The Point, which eventually turned into Groupon, I had the opportunity to invest in June 2007. Also one day, we were white boarding where a dollar of print spend went. We identified paper and transportation as two opportunities to create more savings for our customers. We quickly realized there was not a big play for us in owning trees in Canada and turned our attention to transportation. The industry was much larger than print so Echo was born.

Starting in early 2008 I spent the next three years of my life in transportation at Echo Global Logistics. I was responsible for building out the outside sales force, building processes around implementation and landing some of our largest clients and handling M&A. Echo was another place where we had the great fortune of having some amazing people working there. They were focused on building a great company and really helping our customers enjoy tremendous value. We were able to deliver a successful IPO in October 2009.

As 2010 was winding down, I was tired and needed to recharge my start up fire and get away from the public spotlight. I took some time off and was assisting in evaluating business plans for Lightbank. July 2011, Andrew and Eric asked if I could help at Groupon as they were preparing to go public later that year. Over 18 months I helped in a number of areas in building a strong foundation. The exciting thing about Groupon is the extremely energetic and youthful talent that is all over the company. It is just a phenomenal business model that is adding tremendous value for both merchants and consumers (despite what the media sometimes says).

That is an overview of my journey to date. Over forty years on this Earth and twenty years as a professional. My next chapter is to work with entrepreneurs and companies that want a unique perspective on their own business as they write their journey.