Thanks for having us over.
Thank you so much for thinking of me! How did I get the nod for this!?
It’s not a bad view from the 94th floor of the Hancock. Have you always wanted to live in this building?
I grew up in Springwood, Ohio which is not a place that has a whole lot of view. 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. Now it’s five units combined that I’ve purchased over the course of seven years. It’s not even a view, it’s a picture.
You made this year’s Techweek100, what excites you most about Techweek?
I guess it’s just the collaboration of a lot of really smart folks in a great city. I think over the years Chicago had been dog-tagged as a banking or commodities city but now to have been 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.
CouponCabin.com draws millions of repeat visitors each month. When did the idea come to you?
I was one of the original leaders that started Sears.com and 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 and we would use coupon codes to save money on what we purchased. In late 2002 was when the lightbulb went off to build a site that had coupon codes. When I left Sears I was kind of running from something, not to something. Sears was very, very corporate. We had grown Sears.com 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.
How did you raise capital to turn your idea into a reality?
$5,000 from mom, does that count?
Was there one thing you hadn’t expected going into the bootstrapping process?
Probably just how hard it is. For every good day I’ve had five bad ones that no one knows about and you don’t expect that. 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. 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. No one tells you just how hard it is but if it were easy then everyone would do it.
With all of the startups at Techweek, can you spot a good idea when you see one?
I think any business out there that consumers authentically like and enjoy is a good idea. It doesn’t have to make money, you can figure that out later. It doesn’t have to have a great brand but if you have a product or service or website, whatever it is that authentically connects with a user, that’s the great idea.
What is your biggest piece of advice for young entrepreneurs?
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 verses 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. It all comes down to the mighty dollar. 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. If you can say, “I don’t need to eat this week, I’d rather grow the company,” then that’s what I wish I would have done. In hindsight I shouldn’t have been going out and doing the things that I was. My money should have been going right back into the company.
How do you overcome adversity?
The life of an entrepreneur is problem after problem. Whether it’s an HR problem, a cash flow problem or trying to figure out where your next customer is going to come from. When you’re an entrepreneur and you’re starting a business, it’s everyday. I do believe that there is a higher power pulling the strings and whatever is meant to be is meant to be. There are a lot of things that present themselves that will push you in the right direction that you wouldn’t have thought of otherwise but still everyday is a problem to a different degree.
Which business owners do you admire?
I think what’s most important is what you do after the business does well. I respect a lot of guys who go out and give back and do philanthropy and create foundations. I grew up very humbly and I’m so blessed to be where I’m at today. You have to reflect and see what’s important and that’s what I respect. There are a lot of folks out there who make a ton of money and then put their time back into making even more money when they’ll never spend one-third of it, let alone half. It sounds cliché but I think it’s more about what you give, not what you have.
Do you still use coupons?
Of course I do! I grew up in a small town outside of Cleveland, it was very middle-class so I learned to use coupons from my mom since day one. Her $5,000 investment has paid off pretty well for her! She still uses coupons to this day.
You were on the 2016 Olympic committee. How cool was that?
It was fantastic! I have a long family history of Olympic fans. I got to go to Copenhagen. The Olympics will be coming to Chicago someday, hopefully.
Where do you see yourself in 10 years?
Hopefully married with kids. I’ve sacrificed too many relationships and things like that for the business.
If you could have a drink with anyone, who would it be?
Abraham Lincoln. A lot of people had taken on slavery before him and failed, it was a monumental task that he ultimately paid the most important price for. To see people fail before you and still say, “I’m going to go after that,” is pretty ridiculous.