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Monkey Business Radio
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, and empty advice to bring you the practical insights you need to grow and sustain a successful company. From candid conversations on overcoming challenges to expert interviews with those who’ve made it big, we’re here to give you the tools, tips, and motivation to build your own success story.
Whether you're starting your very first business, looking to break through the $1 million mark, or aiming to scale even further, Monkey Business Radio has something for you. Join us as we share the journey, from the humble beginnings to the highs (and lows) of reaching multi-million dollar status. Tune in, get inspired, and let’s build your dream business together!
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Episodes
23 episodes
Episode #23 - Alicia Conlin: Building Recovery Capital & Community on Cape Cod with WellStrong, Inc
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 t...
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Season 1
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Episode 23
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37:14
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Episode #22 - Startup Strategies for a Successful Small Business
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 ...
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Season 1
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Episode 22
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40:36
Episode #21 - Chance Favors the Prepared - Small Business Edition
Episode #21 – Chance Favors the Prepared: Small Business EditionIn 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 ...
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Season 1
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Episode 21
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42:27
Episode #20 - Talking Movement and Mission with Nicole Spencer
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, a...
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42:42
Episode #19 - The Small Business Five Year Plan
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 p...
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Season 1
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Episode 19
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37:14
Episode #18 - Financial Statements for the Small Business
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 los...
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Season 1
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Episode 18
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43:49
Episode #17 - Building a Recession Proof Small Business
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 reall...
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Season 1
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Episode 17
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32:04
Episode #16 - Introducing the South East Gutter Monkeys
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 ...
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46:10
Episode #15 - Leap of Faith
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
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40:05
Episode #14 - Dealing With Competition
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 pan...
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45:04
Episode #13 - The Island of the Blind
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...
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37:29
Episode 12: Funding your Small Business
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...
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34:40
The Visionary
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 unpa...
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Season 1
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Episode 9
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45:33
Valuing Your Small Business IP
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 j...
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Season 1
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Episode 8
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37:32
Valuing Our Business
In this episode of Monkey Business Radio, hosts Chris and Dennis dive into the importance of valuing your business. From financial metrics like balance sheets and P&L statements to the intangible value of In...
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Season 1
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Episode 7
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32:35
Advertising Your Small Business With Warren Palley, Palley Advertising
Advertising can feel like a guessing game, but the right strategy makes all the difference. In this episode, we sit down with Warren Palley of Palley Advertising, the mastermind behind Cape Cod Gutter Monkeys’ radio success and a key player in ...
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Season 1
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Episode 10
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53:30
Financial Literacy 101 - Part 2
Albert Einstein called compound interest the most powerful force in the universe, and in this episode, we dive even deeper into why financial literacy is the key to building real wealth. Whether you’re just starting out or looking...
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Season 1
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Episode 6
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40:20
Monkey Business Radio Trailer
Every once in a while, someone comes along and shakes up a tired industry with a bold new innovation. Monkey Business Radio is about those game-changers—the entrepreneurs who challenge the status quo and build something remarkable from...
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Season 1
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Episode 1
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1:15
Financial Literacy 101 - Part 1
This episode of Monkey Business Radio explores the power of compound interest and how financial decisions made early in life can have a massive impact over time. The Rule of 72 shows how money doubles at a consistent r...
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Season 1
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Episode 5
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42:40
Small Business Success Through Customer Service Excellence
Exceptional customer service isn’t just a bonus—it’s the foundation of a thriving small business. In this episode of Monkey Business Radio, we dive into what makes great customer service stand out, why so many businesses fall short, an...
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Season 1
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Episode 4
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53:45
Branding Your New Company
Unlock the secrets of strategic branding with us on Monkey Business Radio, where your hosts, Chris Collins and Dennis Siggins, aka Bobby Downspout of Cape Cod Gutter Monkeys, unravel the power of a strong bran...
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51:07
Debt and Debt Management for Small Businesses
In Episode #2 of the American Gutter Monkey Radio Hour, Chris and Dennis dive into debt and debt management for personal and business finances. They discuss how understanding when to use debt strategically, and when to avoid it, i...
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Season 1
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Episode 2
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47:12
Moneyball and the Art of Team Building
In this episode, host Chris Collins dives into the art of team building with Dennis Siggins, founder of Cape Cod Gutter Monkeys. Discover how Dennis applies a Moneyball-style approach to hiring, training, and empowering employees to transform a...
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Season 1
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Episode 1
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50:10
