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PODCAST

Monkey Business Radio

American Gutter Monkeys, LLC

Welcome to Monkey Business Radio, the go-to podcast for aspiring entrepreneurs and small business owners who want to take their business from the ground up to a multi-million dollar success. Hosted by Rusty Dripedge and Dennis Siggins—better known on the Cape and Islands as Bobby Downspout—this show dives deep into the real-world strategies, hard-earned lessons, and fundamental truths behind building a thriving business from scratch.Each week, we cut through the noise of trends, quick-fix solutions,

business entrepreneurship

All Episodes

53:40

The Business of Being On Time: Tom Keyes discusses...

Monkey Business Radio ·

2026/10/04

Send us Fan Mail What do precision metal manufacturing and a gutter company have in common? Turns out… a lot more than you might think. On this episode of Monkey Business Radio, Dennis and I sit down with Tom Keyes of Keyes Quality Metals & Engineering to talk about what really makes a small business work. Tom has spent decades working with manufacturers and business owners, and today he runs his own precision metal manufacturing company. But whether you're bending metal, installing gutte...

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52:11

Island Pickle - Interview w/ Owner Bill Russell

Monkey Business Radio ·

2026/07/29

Send us Fan Mail What happens when a chance conversation leads to one of Cape Cod's most unique new businesses? In this episode of Monkey Business Radio, Chris Collins and Dennis "Bobby Downspout" Siggins sit down with Bill Russell, founder of Island Pickle in Mashpee. What began as a vision for Cape Cod's first dedicated indoor pickleball facility has quickly evolved into something much bigger—a destination built around community, entertainment, great food, and unforgettable experiences. Bil...

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45:34

Category Kings

Monkey Business Radio ·

2026/06/29

Send us Fan Mail Every so often on Monkey Business Radio, we like to step back and talk about one of the fundamental principles behind building a successful business. In this episode, Chris Collins and Dennis Siggins explore the idea of becoming a Category King—a business that focuses on one thing and becomes the company customers think of first when they need that service. Using examples ranging from 1-800-GOT-JUNK to Dunkin', McDonald's, and even Blockbuster, Chris and Dennis discuss why fo...

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60:53

Interview with Green Abundance by Design: Profit with...

Monkey Business Radio ·

2026/02/18

Send a text Season 2 kicks off with Andrew and Mike of Green Abundance by Design, an ecological landscaping company that takes a nature-led approach to designing and caring for landscapes. With a focus on native plant gardens, invasive species management, and thoughtful lawn care, they’re helping homeowners improve their properties while enriching the natural environment. In this episode, we explore the counterintuitive decisions that fueled their growth—especially creating year-round j...

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42:10

Episode #25 - Silver Tsunami On Main Street

Monkey Business Radio ·

2026/01/27

Send us a text Wayne Gretzky said he didn’t skate to where the puck was — he skated to where it was going. Demographics say the puck is headed straight into a massive turnover of small business ownership, as millions of Baby Boomer–owned companies change hands, get passed down, or shut their doors. That wave is the Silver Tsunami. In this episode, Chris Collins and Dennis Siggins (a.k.a. Bobby Downspout) break down what this generational shift means beyond the headlines — for retiring owners,...

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50:49

Episode #24 - Employment Tailwinds at the Gutter Monkeys

Monkey Business Radio ·

2025/12/10

Send us a text The labor market has always cycled up and down—but COVID erased predictability and rewrote the rules for hiring. In this episode, Chris Collins and Dennis Siggins (a.k.a. Bobby Downspout) look at how the trades have adapted, why qualified candidates are finally returning, and what that means for small-business growth in 2025. Dennis shares how he rebuilt his crews at Cape Cod Gutter Monkeys, what he’s seeing in the broader trades and union markets, and how his five-step philoso...

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37:14

Episode #23 - Alicia Conlin: Building Recovery...

Monkey Business Radio ·

2025/10/14

Send us a text WellStrong is a 501(c)(3) in East Falmouth using fitness, peer coaching, and community to support people in recovery from substance use disorder. Executive Director Alicia Conlin joins Chris Collins and Dennis “Bobby Downspout” Siggins to share how WellStrong pairs evidence-based WAM (Whole Health Action Management) with a full gym, peer wellness coaches, and “boots-on-the-ground” outreach. We talk recovery capital, accountability, employment pathways, events like the WellStron...

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40:36

Episode #22 - Startup Strategies for a Successful...

Monkey Business Radio ·

2025/09/30

Send us a text Starting a small business is exciting—but the first year is often the hardest. In this episode of Monkey Business Radio, Chris Collins and Dennis Siggins (a.k.a. Bobby Downspout of Cape Cod Gutter Monkeys) dig into the strategies that help entrepreneurs not just survive, but thrive in those early stages. From avoiding common pitfalls to focusing on the decisions that drive profitability and growth, Dennis shares lessons from decades of working with small business startups and o...

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42:27

Episode #21 - Chance Favors the Prepared - Small...

Monkey Business Radio ·

2025/08/19

Send us a text Episode #21 – Chance Favors the Prepared: Small Business Edition In this episode, Rusty Dripedge and Bobby Downspout explore how preparation drives real growth in small business. From hiring before you need to, to buying your next truck or upgrading your space ahead of demand, being ready is often the difference between thriving and stalling out. Dennis introduces his Business Growth Chart—a tool that helps business owners forecast needs, avoid self-imposed ceilings, and build ...

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42:42

Episode #20 - Talking Movement and Mission with...

Monkey Business Radio ·

2025/07/08

Send us a text Nicole Spencer has built a life around movement—not just as a runner, but as a nonprofit leader, coach, and now founder of Apex Strategy Partners. In this episode, she shares how a simple love of running became a tool for healing, leadership, and impact. From organizing a 275-mile relay from Ground Zero to Cape Cod, to raising hundreds of thousands for veterans, to helping small organizations find their footing—Nicole shows us what it means to lead with heart. Her story is a re...

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37:14

The Small Business Five Year Plan

Monkey Business Radio ·

2025/06/26

Send us a text Most small businesses never look beyond the day-to-day—or maybe a year out at best. But if you want to build real value, you need a plan that reaches further. In this episode, Chris and Dennis walk through what a true five-year business plan looks like: how to set short-term goals, when to reassess and pivot, and why defining what business you’re actually in is a critical early milestone. (Hint: Dennis thought he was in the ski business. He wasn’t.) Whether you're starting fres...

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43:49

Episode #18 - Financial Statements for the Small...

Monkey Business Radio ·

2025/06/11

Send us a text If you own a small business—or you're thinking about starting one—this episode is a must-listen. Chris and Dennis break down the three financial statements every business owner should understand: monthly and annual sales reports, profit and loss (P&L) statements, and the all-important balance sheet. From tracking seasonal trends to spotting early signs of trouble, they explain how these tools can help you make smarter decisions, grow more confidently, and build real value o...

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32:04

Episode #17 - Building a Recession Proof Small Business

Monkey Business Radio ·

2025/06/04

Send us a text Recessions, inflation, supply chain disruptions—every business faces storms sooner or later. The question is, are you ready for them? In this episode, Dennis Siggins draws from more than 40 years of business experience to share what really works when it comes to building a recession-proof small business. We talk about how to read the signs of a downturn before it hits, why keeping strong financial records matters more than ever, how to build the cash reserves that can keep your...

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46:10

Episode #16 - Introducing the South East Gutter Monkeys

Monkey Business Radio ·

2025/05/28

Send us a text In this episode of Monkey Business Radio, we sit down with Scott Wellington—longtime customer turned proud owner of Southeast Gutter Monkeys, the newest franchise in the American Gutter Monkeys network. Scott opens up about why he and his family made the leap into business ownership and what stood out most wasn’t the startup kit, the tools, or the branding—it was the culture. From day one, what mattered most to Scott was how people were treated. The respect for employees, the t...

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40:05

Episode #15 - Leap of Faith

Monkey Business Radio ·

2025/05/22

Send us a text 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 ...

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45:04

Episode #14 - Dealing With Competition

Monkey Business Radio ·

2025/05/15

Send us a text Starting a business and finding yourself surrounded by competitors? That’s not a problem—it’s validation. In this episode, Chris and Dennis dive into what competition really means for a new or growing business and how to navigate it without panicking, discounting, or losing sight of your value. From naming and branding to customer service and quality control, the conversation highlights what it takes to stand out—especially in saturated markets. Real-world stories from the Cape...

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37:29

Episode #13 - The Island of the Blind

Monkey Business Radio ·

2025/05/07

Send us a text What if the secret to market dominance isn't competing with others, but finding spaces they've completely overlooked? "On the island of the blind, the one-eyed man will be king." This powerful business philosophy—discussed by hosts Chris Collins and Dennis Siggins—reveals how smart entrepreneurs identify untapped markets and position themselves as the only solution, becoming leaders by default rather than through direct competition. Dennis shares how Cape Cod Gutter Monkeys b...

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34:40

Episode 12: Funding your Small Business

Monkey Business Radio ·

2025/05/01

Send us a text Starting a business takes more than just a good idea—you need a funding strategy that fits your goals, risk tolerance, and lifestyle. In this episode of Monkey Business Radio, we break down the four most common ways entrepreneurs get their ventures off the ground: bootstrapping with personal savings, acquiring debt, selling equity, and using a royalty-based model. We talk candidly about the financial realities of starting small—selling off personal assets, living lean, an...

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45:33

The Visionary

Monkey Business Radio ·

2025/04/11

Send us a text Most folks go where the puck is. Visionaries? They go where the puck is gonna be. In this episode, we dig into what it really means to think ahead in business—and how that mindset can drive long-term growth. Dennis and Chris unpack how to build a five-year plan, recognize your weak spots, and surround yourself with the right people (hint: not yes-men). We hear the story of Marjorie Merriweather Post—a 27-year-old who turned breakfast into big business—and how her instincts resh...

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37:32

Valuing Your Small Business IP

Monkey Business Radio ·

2025/03/27

Send us a text In this episode of Monkey Business Radio, Chris and Dennis dig into one of the most overlooked assets in small business—intellectual property (IP). From brand reputation and trade secrets to goodwill and systems, your IP might just be the most valuable line on your balance sheet. They share real stories—like how AGM built its IP from scratch, why owning vs. leasing real estate changes everything, and how iconic brands like Jordan’s Furniture and Ken’s Steakhouse show the power ...

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