Meet Keenan

My Story

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. The school football team had just played for the National Championship, and it looked like another dope place to party.

So, this time, I got a ride, ‘cause my Jeep was gone, and headed to Boulder.

After two years in Boulder partying and having a blast IT happened.

It was the Christmas Holiday. The school was closed. Most of the other kids had gone home to visit family. Boulder was mostly a ghost town over Christmas. Unable to afford to go back to Boston to see family, I was delivering food to make rent. It was a cold and snowy night (No, really. It was a really cold and snowy night). I was driving down Broadway, with the campus on my left-hand side. I was driving an old Ford Escort, owned by the restaurant where I worked. I was delivering matzo ball soup at 8:00 at night. There was no one on the road other than me. It was dumping, the road wasn’t plowed, and the streetlights glistened off the snow. It was picturesque, but I didn’t see it that way. At least not at that moment. As I passed the University, it hit me. I was becoming a failure. I was literally becoming what everyone expected of me: nothing. I had nothing going on in my life. I was partying, hanging out, and delivering soup!  It was right then and there I knew, it was time to stop fucking around. I was 24 years old, driving a piece of shit Ford Escort, over the Christmas holiday, delivering matzo ball soup in the snow, so I could make rent for some shitty apartment. 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 around 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 (Ok, I walked, I had 3 credit hours to finish. That’s another story.)

After graduating, kind of, I moved to Denver and then to South Beach Miami to model. I guess I didn’t get it all out of my system. Yet, 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. I’m thinking, 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 and was crushing it. I was then hired by a guy named Mike Sexe (pronounced sexy, I can’t make this shit up), to sell IT consulting services for a consulting firm making 100k plus a year. I’m now 28, you didn’t have to ask me twice. I knew absolutely NOTHING about IT or technology yet became one of their top performers and was named a partner after just two years.

After three amazing years at the IT Consulting company, I became Vice President of Sales for a large CLEC (Competitive Local Exchange Carrier), where I was responsible for 300 million in revenue and 125 people nationwide. For those of you at home doing the math, you are correct. I went from the streets of South Beach Miami to running a 300 million dollar line of business and overseeing 125 people in 4 short years. It was meteoric! And I doubled my salary AGAIN!

It was this meteoric rise that brought me to where I am today. Because I was so young, only 32 at the time, when it came time to find a new gig, I was unable to compete with my peers for the same positions. They were consistently 10-20 years older than I was with 15-20 years of experience. I had less than 15. I couldn’t compete on paper. Resumes suck!!

Enter the A Sales Guy blog (now A Sales Growth Company).

Because of this disadvantage, I started the A Sales Guy blog in February of 2009. The idea: show people what I can do. Don’t tell them. I posted a blog every day for 712 days straight. That’s every day for almost 2 years. I wrote about every sales topic you could imagine, from leadership to prospecting, to account management, to commission plans, etc. I hit them all. With that commitment, A Sales Guy was getting noticed. It was listed as a top sales blog all across the web. My audience grew from a few 100 to 10’s of thousands. I was being asked to speak at conferences and help organizations fix their sales teams. With this momentum behind me, I told the corporate world to pound sand and started A Sales Guy Consulting (now A Sales Growth Company). I didn’t fit in the corporate world and I knew it. Just like school, structured, hierarchical systems didn’t work for me. I got out and never looked back.

Since then this hyper-active, 5-year high school flunky, ski bum, male model, corporate drop out has helped sales organizations all around the world, from Fortune 500 to startups. I’ve helped them all. I have written for Forbes, Harvard Business Review, MIT Sloans. I have 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 continually sited as one of the foremost experts in sales in the world. I’ve also written two books, Not Taught and Gap Selling. Gap Selling has been an amazing success.

Why share my story this way and open up about who I am? It’s because I believe that too many of us let life dictate to us, we don’t dictate to life. We own life, life doesn’t own us. No one should define us or tell us who we are or who we should be. We should be telling ourselves who we are and who we’re going to be. No matter where we are in life, there is no end or no failure until you give up. No one controls your success. We all have it in us to make a difference, to achieve the goals we want, to build the life we want, on our own terms.

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.

P.S. — To my H.S. guidance counselor and everyone else who didn’t have faith in that troubled kid, — “How ‘bout them apples!”