Keenan — Creator of Gap Selling and Problem-Centric Selling

At 8, I was labeled hyperactive and put on Ritalin. I flunked out of my freshman year of high school with all Fs and had to start over. At 16, I got kicked out of the house and lived on my own for the last part of my junior year and most of my senior year. During my senior year of high school, my guidance counselor told me I wasn't going to college and to get back to class because I was wasting her time. I graduated high school after 5 years with a 1.5 GPA at the bottom of my class.

To say I was a problem child wasn't a stretch. Yet oddly, for those paying attention, I wasn't. I just didn't like doing things the way everyone else did them. I was anything but a problem.

Despite the 1.5 GPA after 5 years of high school, I convinced the admissions office at a small junior college in Boston to admit me under probation. After two years of JR College, I decided I wanted to be a ski bum, so I loaded up my 1987 Jeep Wrangler and drove to Vail, Colorado where I skied 130 plus days. I also managed to have my Jeep repossessed. I lived in the village, walked everywhere, and skied every day. Who needed a Jeep anyway?

After just one season, I was getting bored and decided to move to Boulder. After two years in Boulder, it happened. It was the Christmas Holiday. The school was closed. Most of the other kids had gone home. I was delivering matzo ball soup at 8:00 at night in a cold and snowy Boulder. As I passed the University, it hit me. I was becoming what everyone expected of me: nothing. I had nothing going on in my life. I was 24 years old, driving a piece of shit Ford Escort, over the Christmas holiday, delivering matzo ball soup in the snow to make rent. I had enough.

The very next semester, I was enrolled as a Sophomore at the University of Colorado, Boulder. A year later, I won a full scholarship to circumnavigate the world in the Semester at Sea program. A year after that I graduated from the University of Colorado with a BA in Political Science.

After graduating, I moved to Denver and then to South Beach Miami to model. Only after a very short stint in Miami, a good friend called and said, "You need to come back to Denver. I have a job for you." That job was selling Chamber Memberships for the Denver Metro Chamber of Commerce for $50,000 a year. This is 1996. Someone is going to pay me a thousand dollars a week to work. I'm in.

And this is how my professional sales career started. After just one year at the Chamber, I broke countless sales records. I was then hired to sell IT consulting services, knowing absolutely nothing about IT or technology, and became one of their top performers — named a partner after just two years. From there, I became Vice President of Sales for a large CLEC, responsible for $300 million in revenue and 125 people nationwide. In four short years, I went from the streets of South Beach to running a $300 million line of business.

Because I was only 32, I couldn't compete on paper with peers who had 15–20 more years of experience. So in February of 2009, I started the A Sales Guy blog. I posted every day for 712 days straight. The audience grew from a few hundred to tens of thousands. I was being asked to speak at conferences and help organizations fix their sales teams. With that momentum, I told the corporate world to pound sand and started A Sales Growth Company. Structured, hierarchical systems never worked for me. I got out and never looked back.

Since then, this hyperactive, 5-year high school flunky, ski bum, male model, corporate dropout has helped sales organizations all around the world — from Fortune 500 to startups. I've written for Forbes, Harvard Business Review, and MIT Sloan. I've been highlighted in Inc. Magazine, Entrepreneur Magazine, and Fast Company. I've been named one of the top 50 Social Sellers in the World by Forbes and one of the foremost experts in sales in the world.

I've refused to let the world around me tell me who I'm supposed to be, how I'm supposed to do it, and when. I've been the captain of my own ship — and there is nothing I regret.