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Episode #15 - Leap of Faith

Monkey Business Radio

Monkey Business Radio
Episode #15 - Leap of Faith
May 22, 2025
American Gutter Monkeys, LLC

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After 35 years in the corporate world, Andy Brennan hit a crossroads. At 55, he walked away from a steady paycheck and a VP-level job—and took a leap of faith into small business ownership.

In this episode of Monkey Business Radio, Andy joins Chris and Dennis to talk about the journey from burnout to business ownership. They cover the early days of Cape Cod Gutter Monkeys, the value of planning (and re-planning), and how trust, partnership, and a simple business model laid the foundation for success.

You’ll hear how Andy and Dennis built the company out of a garage, used church bulletins and radio ads to land their first jobs, and why they chose to focus solely on gutters. They also share how the franchise idea came to life when customers started asking, “Can I do what you do?”

If you’ve ever thought about leaving the 9-to-5 behind—or wondered what it takes to build a business later in life—this one’s for you.