For fans of my columns, you may notice that they are a little different than most. I try to distill universal truths into 500-word sound bites. As a motivational speaker, I tend to think in absolutes. I develop a theory based on my experiences, which I convince myself that I can turn into a teachable moment. And then I bend the narrative to make my case. Who knew that I even had the talent to do this? This is about as far away from my dream of being a rock star as you can get. 

Recently, on a very cold Friday afternoon in February, I found myself pondering something that many entrepreneurs may wonder about: Why was I not afraid to take risks? Why was I not afraid to fail? 

I began thinking about this after recent conversations with two people I have known for years. The first was with my brother Jeff who is 10 years older than I am, and the other was with a very old friend I had the great fortune of re-establishing a relationship with recently. Both of them knew me years before I had any success, and both gave me insights into their choices as well as my own decisions.

In both examples, while the appearance of their respective choices seem "safe," I must add that they both went on to have stellar careers in their chosen fields, both loved their jobs, and--just as easily as any entrepreneur--could have failed. The difference, as I see it, is that their risks were much closer to the ground, allowing a safer fall and easier pivot. In other words, and without taking away anything from their respective accomplishments, the decision to go "all in'' was less dangerous.

My brother Jeff knew exactly what he wanted to do after college. He became a New York City school teacher, a decision he made in part because he felt that a job like that would give him the certainty of an economically secure future. In essence, this was a very smart and fairly risk-averse choice. He is now retired after a 40 teaching history, and by all accounts everything financially worked out as advertised. 

My old friend Victor was a drummer who was following his dream of rock stardom and found himself at the age of 22 picking up extra cash in a peripheral job in the theater world by chauffeuring Joseph Papp around while working for Shakespeare in the Park in New York City. This opportunity led to a stagehand job. When Victor decided to walk away from his rock 'n' roll dream, he also realized that he loved the backstage theater world, and this is where he established a great career. In Victor's words: "While working in the theater world, days became weeks, weeks became years, and you realize one day that you have a career that you didn't know that you had."  

So Victor did take a risk at one point, knew when to get off the high risk merry-go-round, and again, like my brother, landed just where he wanted to be.

Then there is me.

I love rock and R&B music. It totally consumed me. I went to see every performer I could seemingly every night of the week from the age of 15 to 20 (1967-1972). As a teenager, the obsession to be in the rock 'n' roll business in any way drove me to make my career choice. I carried a guitar around with me everywhere I went and told people that I was going to be a rock star. I practiced my guitar, playing for hours on end and imagined myself playing guitar for the Grateful Dead, the Allman Brothers, Led Zeppelin, Pink Floyd, the Rolling Stones etc. I also knew one thing for certain: I didn't need a high school or college diploma, which is why I became a high school dropout. I had a crazy dream, which I had absolutely no idea how to accomplish and took risk after risk without any safety net. I had no choice. I had to have this so bad that nothing could stop me.

I was 20 when we started Twisted Sister, and, after 10 years of the band struggling in the club scene, and failure after failure, we made the big leap in 1983. And for five years, we grabbed the brass ring of worldwide fame--only to watch it crash and burn in 1988, leaving me broke and divorced. Undaunted, I remarried, had a child, and reinvented myself as a producer and manager of the band Sevendust. When I walked away from managing Sevendust, I went though yet another divorce and put Twisted Sister back together again, only to find the band's world wide popularity as well as the licensing of our classic songs, made us more financially successful then we ever were. In short: I took a very big risk, suffered a number of very big crashes...and in the end netted a very big reward. How did I know that things were going to work out?

I didn't. 

You never know, but looking back, it seems that the fear I had still didn't succeed in stopping me. I love this business and still do.

Were there sleepless nights? Of course. Were there times that I felt that I was staring down the abyss? Absolutely. Did I walk away from the music business after the birth of my daughter and assume that I was no longer able to withstand that risk again? Yes, I did. 

What the hell happened then? Why did I return yet again, to the scene of such victory and defeat? Cynics would say that it's because it's the only world I know. Wrong.

So why was I not afraid to take risks? Or to fail?

It all comes down to passion. My passion was (and still is) so great that the sheer nature of the intoxicating effects of changing the world through music keeps giving me the faith that I will succeed.

Published on: Feb 17, 2015