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The Gutter Monkey Story

In the fall of 2014, Andy Brennan and Dennis Siggins started the Cape Cod Gutter Monkeys, a gutter cleaning and gutter installation company 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) have since left their jobs and now run the Cape Cod Gutter Monkey office. Each of the couples has a son working for the business as well.  And the two couples still take vacations together. “It’s been fun!” says Nancy.

Another former college roommate, Bruce Duffy, has served the team as the Web Master since 2015.  Bruce has since fully partnered with Dennis and Andy in a new “parent” company; American Gutter Monkeys (AGM). Bruce has relocated to Cape Cod and is directing the franchising effort.  AGM will serve to grow this successful, proven business model beyond Cape Cod. AGM currently has three licensed partners; the Cape Cod Gutter Monkeys, South Shore Gutter Monkeys, and South Coast Gutter Monkeys.

By early 2022, the Cape Cod Gutter Monkeys, based out of the industrial park in Mashpee, has grown to ten trucks and 20 employees.  They are in the final phase of construction of their new facility, set to open in March of 2022.  For seven consecutive years, their award-winning marketing program has been recognized by the Massachusetts Broadcasters Association. 

With four successfully operating locations, the team has created the American Gutter Monkeys, a licensed franchisor, with the intent of bringing the brand to other areas of the State and beyond.

“I love going to work every day,” says Andy.  “I don’t miss the corporate world at all.”