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Navigating Back Roads: How One Entrepreneur Found His Way to Success

Navigating Back Roads: How One Entrepreneur Found His Way to Success Credit: Reg Harnish

The road I took to become co-founder and CEO of my own company was in no way traditional. My story doesn't include awards that recognize achievements or motivational speeches to my peers. It doesn't even include a graduation day selfie. Go look. You won't find one.

The truth is, I didn't do well in college. I didn’t even earn a degree. I spent two years at Rensselaer Polytechnic Institute, and all I have to show for it are horrible grades and unpaid parking tickets.

School wasn't for me, but I made up for it by working hard every day. I wanted to be like my grandfather, who worked day and night as a television repair man. He inspired me, along with his willingness to make time for me no matter how busy he was.

When I was 13, he gave me my first computer; and that's when my life changed. Captivated by programming and coding, I became obsessed with zeroes and ones. I guess I got pretty good at it, too, because I was recruited straight out of college at 20 years old to work for a major government agency in Washington D.C. I was, however, immediately turned off by the bureaucracy and lack of energy there. It wasn't for me. So, after nine months, I left.

At this point, my career was already headed in a different direction. I was an entrepreneur at my core, which is probably why working for other companies and organizations, and watching them gratuitously waste money and resources, didn’t sit well with me.

The following years, I made stops at several businesses, ranging from established Fortune 500 firms to technology startups like SynQuest where, in 1995, I was the seventh employee spearheading the IT department and deploying software. That was the first time I got a taste of what it feels like to build a company from the ground up. And I liked it.

After SynQuest went public in 1999, I left and started my first software company with Elon Musk's brother, Kimbal, just prior to the dotcom crash of 2001. Unfortunately, it was short-lived.

We called it FunkyTalk. You could say we were ahead of our time, because the cloud-based video editing site failed to attract enough funding, as many investors had all but fled the dotcom world.

Was it bad timing? Yes. Did I give up? No.

After we sold FunkyTalk in 2001, I needed time to figure out my next move.

Most people experience doubts after taking a risk, especially when it doesn't turn out as planned. But, if anything, that uncertainty fueled my desire to keep pushing. After an eight-month hiatus, I was ready to jump back into the fold.

In 2002, I was hired as CTO of Autotask, a leading software development company. I spent five years building one of the world's most popular cloud-based applications and became the third largest shareholder in the company.

But, something was still missing. I wanted a company that was all mine.

The idea behind GreyCastle Security was born at a backyard barbecue in 2010 over frustration with current security solutions, a deep desire to make a difference and a plate of grilled vegetables. It was clear that cybersecurity was the next big thing, and I was once again inspired to take on the challenge of building a company that would tackle these issues.

It was, and still is, hard work. But for the first time in my career, I had the experience to ask the right questions and the mettle to push through any challenge. Six years later, GreyCastle Security is the industry's leading provider of cybersecurity risk assessment, advisory and mitigation services. We are a multimillion dollar firm, with clients in nearly every state, specializing in healthcare, higher education, utilities, retail and financial services.

This year, we landed on the Inc. 5000 and the Cybersecurity 500, and I was named North America's Cybersecurity Consultant of the Year by my peers in the 350,000-member Information Security Community on LinkedIn.

While I never doubted my success, I knew it would be hard work. I knew it wasn't going to be easy. I have my grandfather to thank for being an example of a hard worker who values family and discovery. Now, just like him, I get to fix things for a living.

About the author: Reg Harnish is an entrepreneur, speaker, author and CEO of GreyCastle Security, a leading cybersecurity risk assessment, advisory and mitigation firm headquartered in Troy, New York. Reg has been practicing cybersecurity for nearly two decades. His contrarian perspectives have established him as a highly-respected thought-"disrupter" in the industry.

Edited for brevity and clarity by Sammi Caramela.