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Corporate to Self Employed – A Personal Decision

From the desk of Andy Brennan

     Upon returning from WWII, my dad worked for the next forty years as a machinist for a local manufacturing company.  We lived a modest lifestyle, but we wanted for nothing. I grew up the youngest of five kids at the tail end of the Baby Boom. 

     I was a solid athlete in high school, and that attracted the attention of the soccer coach at Bentley College (Waltham, MA).  My freshman year, the housing department paired me with Dennis, who ran cross-country and track.  We remained friends and roommates for the duration.  Four years of Bentley business prepared me well, and I followed the path most travelled into corporate America.  My thought process was simple; if I work hard, I will have a job for life.

The path most travelled

     Throughout the years, things happened beyond my control that affected my career.  Right out of college I took a job at a small printing company, and during an ownership change, my position became a casualty of a cost containment maneuver. 

     For the next thirty years, climbing that corporate ladder was often like walking the corporate tight rope!  I elevated myself to high management positions, but I was constantly impacted by upper-level decisions.  Mergers, acquisitions, payroll freezes, constricting job market, and eventually payroll and benefit reductions severely hindered my growth and happiness, as I danced on that wire-thin corporate cable.  Job security, growth potential, and great business environment, all the things that I loved about work, had been replaced with frustration and disappointment.  I was in my mid 50’s, unhappy with my work life, and wondering how I was going to get through the next 10 years.

     In September of 2013, my old roommate and I spent a few weeks with our wives in Hawaii, celebrating our respective 30th wedding anniversaries.  While we had taken different paths in life, Dennis and I were never more than a phone call away.  I had often thought about self-employment, but 35 years of corporate life had me questioning if I had the discipline and guts to take the steps.  I asked myself, “Did my years in the corporate world provide me with the transferable skills to crossover to the self-employment world?”  Dennis had the self-confidence to start his own business right out of college. He had owned several companies and every one of them had been successful.  It was here on the sands of Maui that we first discussed the possibility of partnering together in business. 

     “To be honest,” said Dennis. “I really didn’t think you were serious about leaving the corporate world.  I thought you were just blowing off steam.”

A path less travelled

     Six months had passed since the Hawaiian vacation, and I was still working my corporate job when Dennis and I shook hands on the deal!  We began working weekends and evenings building out the business plan, company name, logos, color combinations, tag lines, marketing strategies.  We each wrote out checks and fully capitalized the business to face head on the ebbs and flows that challenge a startup business.  The process took 7 months, and I wondered if this was all necessary.  Dennis believed in this process; “This will be our first competitive advantage.”

     After all this work, I had finally come to the crossroad. Was I ready to quit the comfort and stability of corporate life and dive headfirst into the unknown of self-employment?

“It is better to take a chance in life than to live in that gray twilight that knows neither victory nor defeat.”

     For me, the answer was simple; it was finally time for me to invest in myself. I knew in my heart that with the help of a strong partner and a very supportive spouse, I would be a success. The day I gave my notice to the corporate bosses was one of the happiest days of my life. Sure, I was nervous, but it was a good nervous.  I have been an athlete my whole life, and I know it is good to be nervous before a big game. It keeps you on edge and allows you to focus on the task at hand. Yes, I was taking a big risk, but the greatest risk is never taking one.

“Don’t be greedy, don’t be stupid!”

     We started as a home-based operation, but with a rapid learning curve and high profit margins in a hugely underserved market, we quickly outgrew our home-based operation.  We purchased a small building in the local industrial park.  Despite the success and growth of the company, Dennis and I each lived on a very tight salary and reinvested most of the revenue back into the company.  Dennis and I do not take salaries that reflect our value to the company; we take salaries that reflect our commitment to the company.  This discipline is one of the keys to our success; feed the company first and yourself later. We live by a very simple motto, “Don’t be greedy and don’t be stupid”.

     We are so proud of our successful business model that we are now expanding into the franchise market.  The strong partner that Dennis was to me is what we bring to our newest partners as they make the transition from a corporate employee to a self-employed owner of their own destinies.  We have been operating for 7 years now, and with strong business discipline, an award-winning marketing program, and a visionary look at expansion, we have grown a business from $0 to annual sales close to $5 million annually, and we’re still growing at 30% per year!

     Our second territory was opened by Darrell and Cindi Ford, a couple that at one time was a customer of ours.  In a recent conversation that I had with Darrell, a former corporate manager himself, he shared these thoughts; “It took me more than a year to adjust (to the lifestyle of self-employment), but now I have more time with my family… and a lot more money.”  He added, “And during Covid, while we saw other companies going under, we were busier than ever.”  So yes, it can be done. We can leave our jobs and succeed on our own!

     After outgrowing three locations in seven years, Dennis and I are currently building our new 7,500 square foot facility, and we are still debt free. We have many family members employed who will likely carry on the success when we ease into retirement. For now, instead of worrying about being laid off, I look forward to every day of work. I am so proud of the brand that we have nurtured over the years. This is not a job; this is a lifestyle.

(Andy Brennan is a founding member and co-owner of Cape Cod Gutter Monkeys, the Gutter Monkey franchise systems, and Evergreen Band LLC. Visit Andy at

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