A Focus on Chicago Entrepreneur: Darren Guccione

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.”


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.

Start-Up Spotlight – “The Paraders”

This week, we interviewed Rachael Hammon, of The Paraders, an online vintage e-commerce retailer about her start-up story and success. We had so much fun talking to Rachael about how she turned her hobby into a full-time, income generating business.

Rachael also recently launched and completed a successful Kickstarter project to fund her own vintage fashion line.


Excerpts from our interview below:

How did you start your company?

Rachael has been working on The Paraders for over three years now. “[Vintage clothes] was just a hobby that I had and thought I’d test out buying and re-selling online.” In the beginning, Rachael used “just a corner of the living room out of the apartment” which rapidly expanded over the years. Growth came quickly as she started listing on Etsy and reinvesting her profits into new inventory. Clearly, testing your market and validating the idea is something that Rachael is quite good at. Rather than jumping full in with a website and office space, she took a “step-by-step approach” by investing in things that were important. First and foremost, she invested in high quality inventory, photos, and defining her customer experience. Once those items were in place, she later expanded her web presence, found an office, and hired some part-time employees to help manage the growing business. Rachael says of that first year, “It was really slow, but getting started is always the slowest” and it’s all about the “little adjustment and tweaks” you make to grow your business and build a brand.

What compelled you to create a business out of your hobby?

“I was always interested in vintage, not just to wear it, but also in the history.” Prior to creating a dedicated online e-commerce platform to sell her merchandise, Rachael would often buy and sell vintage clothing that did not fit on online exchanges or at local markets.

In addition to her interest, Rachael comes from a long line of entrepreneurs and she was “familiar with the [entrepreneur] lifestyle and mindset from a very early age.” She “always knew that she would own her own business” and her hobby was the perfect launchpad to create a business.


What did you do while The Paraders was starting-up?

In order to launch her startup, Rachael took up nannying, which not only provided her with income, but also, an opportunity at “nap time to get out the computer and work on her business.” Those nap times, gave her a dedicated time every day to work on her business which she feels is extremely important in the early stages of a start-up to succeed.

Tips on avoiding start-up roadblocks:

• Be persistent – Dig deep inside of your passion to “keep up, when the times get tough.”
• Stop procrastinating – Do the things you don’t want to do first. Rachael experienced this first hand as she says “early on, I wasn’t sure what to name the business so I procrastinated for months in setting up my Etsy store.”
• Get out of your comfort zone – Every day, pick one thing that makes you uncomfortable and tackle it. As Rachael says, “power thru the [tough things] and make the hard decisions and make those cold calls” because no one else is going to care about your business the way you do.
• Pay attention to detail – Don’t underestimate the importance of all the small things that make up your business. “Small details make the big picture.”


Has digital marketing helped your business? In what way?


“The big key with social media is that it constantly puts us in front of our customer and target audience.” Whether they’re willing to buy or not today, “the element of being constant and consistent is key.” The Parders uses a variety of social media tools, including, Facebook, Twitter, blogging and email marketing to stay in touch with its customers. “Some of our biggest sales are from social media and email marketing” and a lot of people pay attention to our messaging

All businesses take time, love, and passion, and sometimes, a defining moment. At one point, Rachael reached a point where she had to make a decision. Either she put all of her eggs in the Paraders and went all in, or walked away. She chose the former, and invested in a new office, a clothing line, and staff and she immediately saw success. With her passion, talent, and eye for design, we know that the Rachael and the Paraders will be one of the leading e-commerce retailers and fashion companies in the near future.