Monkey Business Radio cover art

Monkey Business Radio

Monkey Business Radio

By: American Gutter Monkeys LLC
Listen for free

About this listen


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!



---

© 2025 American Gutter Monkeys, LLC
Economics Leadership Management Management & Leadership
activate_mytile_page_redirect_t1
Episodes
  • Episode #13 - The Island of the Blind
    May 7 2025

    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 became the region's only dedicated gutter cleaning service by recognizing a need homeowners themselves didn't realize existed. Eleven years later, no competitors have emerged, demonstrating how identifying and owning an overlooked niche can create lasting market dominance. The hosts examine similar success stories across industries: how McDonald's revolutionized fast food with innovative service models, how De Beers created the diamond engagement ring tradition, and how companies like Rotor-Rooter and 1-800-GOT-JUNK invented entirely new service categories.

    The conversation explores how true market leadership often comes not from superior talent or resources, but from recognizing opportunities others miss. Dennis explains how this principle guided his earlier business as an innkeeper, targeting specific recession-resistant communities rather than competing in overcrowded marketing channels. The hosts also highlight how companies that prepared for unexpected market shifts—like Seafood Sam's restaurants developing delivery systems before COVID hit—can turn challenges into opportunities for growth.

    Whether you're starting a new venture or reinventing an existing business, this episode reveals how identifying genuine unmet needs and positioning yourself as the specialist can help you create a category where you're the default choice because few or no alternatives exist. It's not about being better than everyone else—it's about being the only one solving a particular problem.

    Ready to find your own untapped market opportunity? Subscribe for more insights on building successful businesses through strategic positioning and market awareness.

    Show More Show Less
    37 mins
  • Episode 12: Funding your Small Business
    May 1 2025

    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, and making trade-offs early to build long-term success. You’ll hear real-world stories, from founders who turned a few thousand dollars into multimillion-dollar companies, to legendary gambles like the FedEx founder’s last-ditch trip to Las Vegas.

    We also dive into the unique appeal of royalty-based models like franchising—where you can own your business but benefit from systems, support, and a proven brand. If you’re exploring franchise ownership or looking for a smarter way to launch a service business, this episode offers practical insights, cautionary tales, and encouragement to help you make informed decisions.

    Show More Show Less
    35 mins
  • The Visionary
    Apr 11 2025

    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 reshaped American kitchens. We also talk Cape Cod Gutter Monkeys, marketing wins (and flops), and why hitting every goal might mean your goals aren't ambitious enough.

    This one’s packed with stories, strategy, quotes, and a reminder: your vision doesn’t need to be perfect—it just needs to keep you moving forward.

    So grab your coffee, sit back, and welcome to Monkey Business Radio.

    Show More Show Less
    46 mins

What listeners say about Monkey Business Radio

Average Customer Ratings

Reviews - Please select the tabs below to change the source of reviews.

In the spirit of reconciliation, Audible acknowledges the Traditional Custodians of country throughout Australia and their connections to land, sea and community. We pay our respect to their elders past and present and extend that respect to all Aboriginal and Torres Strait Islander peoples today.