In hindsight I shouldn’t have been going out and doing the things that I was. If you can say, “I don’t need to eat this week, I’d rather grow the co mpany,” then that’s what I wish I would have done. If you’re a small business starting without a big checkbook behind it, there is no difference between the company funds and your salary and your ability to go out and have dinner. I think everyone has their own comfort zone and when your gut tells you to grow faster than you’re comfortable with, that’s probably the toughest decision. I always opted to go within my comfort versus my gut and in hindsight I should have gone with my gut. If I would have grown faster, quicker and larger my business would be in a much different place than it is now.
What is your biggest piece of advice for young entrepreneurs? If you have a product or service or website, whatever it is that authentically connects with a user, that’s the great idea. I think any business out there that consumers authentically like and enjoy is a good idea. With all of the startups in Chicago, can you spot a good idea when you see one? No one tells you just how hard it is but if it were easy then everyone would do it. That only lasted about four months! So then you’re trying to figure it out, you’re selling your car and taking loans from mom. I started CouponCabin when I was 25 years old with the philosophy of, “build it and they will come.” I had $30,000 when I started the site and that was all of the money in the world to me at the time. For every good day I’ve had five bad ones that no one knows about and you don’t expect that. Does that count? What’s one thing you didn’t expect going into the bootstrapping process? How did you raise capital to turn your idea into a reality? We had grown to 350 folks so it became very structured and organized and that just wasn’t the way I did my business. I had gotten to a point where I was unhappy with the red tape and politics of it all so I said, “Why not try and start a coupon site?” At the time there weren’t any sites like that. In late 2002 the light bulb went off to build a site that had coupon codes. When I left Sears I was kind of running from something, not to something. We would use coupon codes to save money on what we purchased. While I was working at Sears we would shop at a lot of our competitors’ stores to see how they boxed things and how they shipped things. draws millions of repeat visitors each month. Now to be stamped for Groupon, 1871, all of these great national tech brands and to have that level of entrepreneurs, founders and venture capitalists in Chicago talking tech is fantastic for the city and also just for tech itself. Over the years Chicago had been dog tagged as a banking or commodities city. I guess it’s just the collaboration of a lot of really smart folks in a great city. You made this year’s Techweek100 list in Chicago, what excites you most about Techweek? I never expected to live downtown full-time because my business was in the ‘burbs, but I bought in this building and just fell in love with it.
I grew up in Lakewood, Ohio which is not a place that has a whole lot of view.
Thank you so much for thinking of me! How did I get the nod for this? It’s not a bad view from the 92nd floor of the Hancock. Have you always wanted to live in this building?
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