Douglas Karr joins host Justin Gray in episode 4 of the “How Did I Get Here? podcast. Doug is the CEO of DK New Media and co-founder and CMO of CircuPress, an email service provider. He has grown to become an established leader in the marketing technology space and is a serial entrepreneur.

What did you want to be when you grew up?

For a long time, I think I wanted to be an architect of all things. I loved drafting and drawing. I don’t think I had a schoolbook that didn’t have some sort of creature or building in it.  Where did that lead you? Did you go to school for architecture? No, that’s the weird thing. When I went through high school, I was always getting in trouble, and partying way too hard, and reckless. I wound up messing up my chances of ever going to college. I graduated high school, and I went straight into the US Navy. 

After you’re done with the Navy, where do you go at that point?

In the Navy, I was an electrician, and after I got out, the workforce was pretty tough back then so I bounced around. I delivered pizzas for Pizza Hut – I did whatever I could do for money – changed peoples’ brakes, worked at the shipyard for a couple years. Then a job opening came up to work at the local newspaper as an industrial electrician. That was really my first dive into media.

We were switching all of our equipment over to internet based, we reinstalled fiber and started networking all of the equipment. We started to do predictive maintenance on the equipment based on failure rates and monitoring productivity over time. That’s when we saw the opportunity for database marketing and I started to make the shift from monitoring and troubleshooting databases and equipment to monitoring and troubleshooting marketing. 

What was the big catalyst to move from a database marketing manager to what you’re doing right now? How did you come to own your own business? 

The catalyst was easy, I got fired. So that puts you on a different road. I was really frustrated when I was working in the newspaper industry and the slow adoption of digital. I knew the future was absolutely in digital marketing. I had a string of incredible successes. I worked for the Indianapolis Colts during the year that they won the Super Bowl. We implemented Exact Target, and Exact Target figured out that I was doing stuff with their system that they hadn’t done yet. They offered me a job.

I then went on to co-found Compendium, which eventually sold to Oracle. It was at Compendium that I really started to see the light that you know what, I think it’s time for me to start doing my own thing. What we saw in the industry at the time were marketing agencies that were specializing. I wanted to start my own agency that was more cross channel to help marketers kind of dial in and connect the dots. I started DK New Media seven years ago, and it’s been a great road ever since.

What led to the confidence to go out and do that? Was there a big influence that led to that?

You know there really was and it was probably during that string of successes that all of a sudden, I’m sitting in all these board rooms and I’m figuring out that these people are paying attention to me and they respect the decisions that I’m making. I start to wonder why I’m not sitting in a board room all the time. It took me doing that for a while before I started opening my eyes that, “hey, why aren’t you leading a company, and why aren’t you driving this change?”.

What advice would you give to your younger self?

You do what you have to do to pay the bills. It may not be what you’re passionate about, but you can find things to get passionate about and you can find opportunities along the way. If you just keep driving, you’ll eventually see those opportunities. If you don’t take any, you’re missing the boat.

Do you think you could hire someone else to do your job? If so, what would those traits be if you had to hire someone to replace yourself?

One of the biggest things is to know what you’re good at and what you’re bad at. Sitting across the room from me right now is my business partner. She is everything that I’m not. I made it a point to not hire someone like myself. One of the key things that you’ll find with any entrepreneur is they recognize their weaknesses, and they play to their strengths. They hire people who can make up the difference or partner with people who can do those other things.

As you are staffing your organizations, what is your favorite interview question that you feel really gets to the heart of who someone is?

I never read resumes. I go straight to online, and straight to portfolios, and Facebook pages, and everything else. I often ask people what they love to do on the side. You’ll find people with some kind of creative outlet, whether it’s music or gaming. When they have these creative outlets, I think they have really good balance.

Takeaway quote: What I figured out eventually was leadership was one of the components that everybody has.