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The Beginnings

Our Story

The CCGM Story

In the fall of 2014, Andy Brennan and Dennis Siggins started the Cape Cod Gutter Monkeys, a gutter cleaning and gutter installation company now based in Mashpee, MA.

Andy and Dennis met as freshmen at Bentley College (Waltham, MA). The housing department at the college put them together as roommates. Through the next four years, Andy and Dennis remained friends and roommates and graduated in the spring of 1981. Over the next 33 years, Andy made his mark in the printing industry, working for several companies, while Dennis started the first of a few companies that he would own in his adult life.

After college, though they headed in separate directions professionally, they remained friends, never more than a phone call away. They each married their sweethearts in 1983. Each family was blessed with three kids. And though they lived several hours apart, they often visited one another, vacationed as families, and remained friends.

In January of 2010, after 25 years of life in New Hampshire’s White Mountains, Dennis and Barbara (his wife and life-long business partner) sold their construction company and moved to their vacation home on Cape Cod…

In 2013, while vacationing in Hawaii with their wives, the two friends began a discussion about possibly starting a small business. (At the time, Andy was Vice President of Estimating and Purchasing for a large printing company, and Dennis was a “semi-retired” former building contractor.) Their discussion continued for several months, and the one topic that reverberated continuously was that gutter cleaning on Cape Cod looks like a potential home run! As a newcomer to the Cape, Dennis remembers having never seen such an underserved market as he saw in gutter cleaning on Cape Cod.

In the summer of 2014, Andy and Dennis shook hands on the deal and opened their Cape Cod Gutter Monkey account at local bank Rockland Trust. Each in their mid-fifties, they heard all the negatives; “You’re wasting your talents!”, “Is this some sort of a joke?”, “There’s not enough gutter cleaning to keep two guys busy all year long.”

By mid-2015, Andy and his wife Nancy sold their home in Walpole, MA and moved to the Cape. Both wives (Nancy and Barbara) soon left their jobs to run the Cape Cod Gutter Monkey office. Barbara and Dennis have a son now working for the company, while Andy and Nancy have one son and one daughter on board as well.  “It’s been fun!” says Nancy.

Dennis and Andy had a third roommate back at Bentley, and Bruce has worked part-time remotely as the resident web master since the beginning.  In 2021, Bruce left his job and sold his home back in Pennsylvania and move to the Cape to join the company full time!!!  Bruce’s focus is to expand the sucessful Gutter Monkey business model beyond its origins on the Cape.  Franchising is the solution.

Since 2014, with just two owners and one truck, the company has branched out and grown both incrementally and exponentially.  Through the normal processes of business life as well as the Covid and the post-Covid challenges, the Gutter Monkey family has expanded to four locations and continues to grow at a rate of 30% per year.

From humble beginnings as a start-up being run out of the garage next to the house, things have prospered.  Having outgrown three successive buildings, the guys knew they needed a “bigger boat”!  In the spring of 2022, the Cape Cod Gutter Monkeys moved into their newly constructed facility in the industrial park in Mashpee, MA!  “I love going to work every day,” says Andy. “I don’t miss the corporate world at all.”