A Focus on Chicago Entrepreneur: Darren Guccione

Posted on February 12, 2013

I recently had the opportunity to meet Darren Guccione, CEO of Keeper Security. Keeper Security is the top grossing Utility app in the World. Darren has been through some crazy ups and downs in his life. His story is inspirational and helps me stay on course when things become difficult. I wanted to share some of the valuable insight I received from him with you. Enjoy!

“To make something simple is extremely difficult.”

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Darren Guccione
Founder and CEO @Keeper Security

Since the early 90s, Darren has had his foot in the water in all sorts of industries. Darren got his bachelor’s in Industrial and Mechanical Engineering from U of I Urbana-Champaign in ’91. After a gratifying position in product design, he decided to make a big switch and got his master’s at DePaul University for Accounting and Finance. He worked in accounting, specifically mergers and acquisitions, and he had a client who quickly teamed up with him to create the first e-commerce software engine for the computer reselling industry. In 2000, it was sold to CNET Networks Inc. In 2011 he cofounded Keeper Security.

How did you have the resiliency to keep moving forward when things were going wrong?

D: In order to be successful, as an entrepreneur, it’s 95% behavioral. It’s the things you probably hear, but you don’t understand until you experience what it is like to suffer and go through pain. That’s what makes you really strong. That’s what makes entrepreneurs succeed. It’s being able to feel like one day you are on top of the world, and the next day you’ve been kicked in the stomach like ‘what the hell just happened?’ But it makes you even more determined to succeed. Rational people go to work at an office, because starting a business is freaking hard. Starting a business, even if it’s a hot dog stand, or a bar, or a technology company… technology is different because starting a business is hard, (but) starting a technology company is really hard because the technology itself is hard. Most people can’t build a tech asset amazingly well, let alone turn it into a business. You have got to be relentless in your behavior no matter how many times you screw up or how many times people say ‘you can’t do it’ or ‘that idea sucks.’ If your heart or your gut… but it’s really your gut, tells you otherwise, then you have got to follow it.

Besides resiliency, we know it takes a great team to get through those moments…

D: It does, and you have to be a strong leader. If you have a business, your employees either emulate you or they go against you. There is no in between. If you are a whiny CEO or you complain, not good. Don’t ever complain or whine in front of your team. Think of yourself as a lion: “you’re tough as ****”

And if you’re afraid?

D: No, no, no. You have to think about it like this. Fear is the best thing in entrepreneurship. Fear makes you focus. The key is… there are 168 hours, not 40 hours. That’s 128 extra hours (working) compared to the average human. Entrepreneurs are in the 128 hour range. After 40, I go home at night, and that’s what I come up with my strategy. “Where is keeper going next year?” “What’s the future?” That **** doesn’t happen during the day, are you kidding me? I got 300 e-mails during the day, phone calls. I’m putting out fires, you know? All kinds of craziness. But at night time, it’s quiet. When everyone else is asleep I work like a mad scientist. And on Sunday, after I play with my kids, I’m planning my ****. And on Monday I execute. If you think about this, if you are working 100 hours a week… let me tell you something: luck is where opportunity and persistence collide.