I developed an early love for listening to music and creating “mixtapes,” so I went out and got a paper route at age 13 to save money for a Nakamichi Dragon tape deck. I rode my bike through all weather: snow, hail, sleet, and rain on my daily paper route (if you have never experienced a winter in New Hampshire – believe me when I say it was not fun riding a BMX bike in 2 feet of snow with 50 newspapers slung over your shoulder). Delivering newspapers taught me the value of perseverance and overcoming challenges to achieve a goal. It also helped me to develop my entrepreneurial mindset.

I carried my work ethic into high school, where I trained and competed in competitive bodybuilding. I became very disciplined by doing the right things, eating well, and doing the hard stuff to achieve the success I was after. Those experiences continued to strengthen my work ethic at a young age, which was a critical factor in my development as I prepared to enter college and then the workforce. I even wrote a book on “How to Prepare For Your First Body Building Competition,” and sold it in the back of Muscle and Fitness Magazine – and yes, I was just 18 years old.

I went to college at the University of New Hampshire, where I majored in Business Administration and had a focus in Japanese. The summer before my senior year, I was approved to own a College Pro Painting franchise in southern New Hampshire. During that summer, I hired 15 friends and employees, and we painted over 25 homes. We generated approximately $50,000 to $60,000 worth of business – not too bad for a college kid.

A year later, I graduated from the University of New Hampshire and was hired to be an Inside Sales Representative for Cabletron Systems, Inc. – a computer networking company (bigger than Cisco Systems in the day…). My job was to make anywhere between 50 to 100 outbound calls a day to new prospects with the goal of scheduling appointments for my Outside Sales Representative. I was pretty good at sales, and within a year, I was promoted to Outside Sales.

In 1994, Cabletron relocated me from Dover, New Hampshire, to San Jose in Silicon Valley – California.

The second day after I moved out to Silicon Valley, I had my first sales meeting. There I was, the “new kid on the block,” and around the table sat eight or nine other sales reps and the VP of Sales – Tom M. That meeting was a MASSIVE eye-opener for me. The VP of Sales stared down every sales rep at the table and was merciless with them for not knowing the answers to basic questions like, “Why are your prospects looking to buy networking gear?,” “What are the challenges they’re trying to overcome?,” “Do they have a budget?,” “What’s their time-frame?”

As I was watching this happen as the new guy, I took meticulous notes of what questions the VP of Sales was asking. Those questions I wrote down that day became my checklist, and my success formula when I went out into the field. I always made sure I knew the answers to those questions so that when I was back in front of the VP of Sales, I didn’t get chewed out.

Most of the sales reps saw the VP of Sales as an aggressive jerk in the sales meetings. I saw it a little differently. He was coming across this way because he had an excellent track record as the number one sales rep for many years at his previous company, and he knew how to grow a sales pipeline and how to close deals. So I viewed my time under him as an opportunity to learn from a winner – as harsh as he was.

Unfortunately, the VP of Sales wasn’t a good teacher, and most of the sales reps didn’t figure things out as I had.

My lesson from this… KNOW YOUR STUFF if you want to be successful.

I never took a photo with the VP of Sales at my first job, but I did manage to get a photo with legendary coach Lou Holtz at a Cabletron National Sales Meeting.

The more I implemented the questioning and answer process that I started to perfect, the more successful I became. In 1997, I left Cabletron and went to Cisco Systems for about a year. In 1998, I got a once in a lifetime opportunity to become part-owner of a Cisco reseller that was in its early stages of development. Planetary Networks was a $6 million company when I signed on. Being a part-owner, I implemented the sales processes I had learned and practiced at Cabletron, hired 25 sales reps, and taught them my same methods. Within 18 months, Planetary Networks grew from $6 million to $60 million in revenue in a very competitive and commoditized market.

1999 was a hectic time for me because I had also decided to start training for the Ironman Canada triathlon that would take place on August 27, 2000. After a year of training and raising money for the Leukemia and Lymphoma Society, I’m happy to report that I completed Ironman Canada (2.4-mile swim, 112-mile bike, and 26.2-mile run) in 14 hours, 52 minutes and 52 seconds.

The planned exit strategy for Planetary Networks was to sell the company to a larger service provider, but unfortunately, that didn’t happen. When a suitor made us an all-stock offer to buy Planetary Networks, one of the co-founders didn’t want to sell, caused delays, and ultimately killed the deal. When that happened, I changed course and came back to the East Coast in 2000 to start my own company a week after completing Ironman Canada.

Cortex, LLC grew from zero to $3.5Million in sales, but it was a very different time where the economy had crashed after the bubble burst between 1999 and 2001. Many companies were going out of business in 2000 and 2001. But we managed to launch Cortex, LLC, and even excel in the “downturn” because of our agile model. Even though we had less revenue than Planetary Networks, our margin rates were typically 50-85% (which was unheard of in the tech industry), so we were incredibly successful at bringing dollars to our bottom line.

My sales and marketing process had given me the freedom to build and construct my life the way I had always dreamed of doing. I could work from any location and didn’t have to go to an office every day. I no longer had to be in “corporate meetings” that I viewed as a waste of time. I could take on the customers that I wanted and work with the businesses that valued what we brought to the table.