Climbing Ladders: Leaving Corporate America to Start a Gutter-Cleaning Business with Andy Brennan

Andy Brennan is the Founder and Co-owner of the Cape Cod Gutter Monkeys and its parent company, the American Gutter Monkeys, which are both gutter cleaning and installation companies. Alongside his college roommate, Dennis Siggins, Andy founded the company in 2014 after a 35-year stint in the corporate world. Since then, the American Gutter Monkeys has grown and expanded with two locations in the South Shore and South Coast of Massachusetts. In addition to its dedication to delivering excellent customer service, the company hopes to help individuals shift their careers by offering franchise opportunities.

Andy joins us today to share what he has learned from running his own company after working 35 years in corporate America. He discusses his decision to start a business and explains how having a business partner helped him navigate entrepreneurship. He also describes how starting his own business changed him and offers advice to people who want to shift from corporate work to self-employment.

“When you start a small business, you won’t make a lot of money in the first year. Budget properly, work hard, and take as many jobs as you can.” - Andy Brennan

Today on Mastering Midlife:

• Andy’s background and his first job out of college
• What made Andy think about starting his own business after 35 years in corporate America
• Translating corporate skills into self-employment
• Why Andy and his business partner decided to start a gutter cleaning business
• How long it took for Andy and his co-founder to prepare and plan for their company
• The importance of feeding your business
• Gutter Monkeys’ customer base and how they generate peripheral business from gutter cleaning
• The value of over-delivering in entrepreneurship
• How Gutter Monkeys’ business and gutter-cleaning processes have improved over the years
• Their marketing strategy and why Gutter Monkeys shifted from creating infomercials to funny ads
• How entrepreneurship has changed Andy

Connect with Andy Brennan:

• American Gutter Monkeys
• American Gutter Monkeys on LinkedIn
• Andy Brennan on LinkedIn

Mastering Midlife...Together!

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