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Monkey Business Radio

Monkey Business Radio

By: American Gutter Monkeys LLC
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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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© 2025 American Gutter Monkeys, LLC
Economics Leadership Management Management & Leadership
Episodes
  • Alicia Conlin: Building Recovery Capital & Community on Cape Cod with WellStrong, Inc
    Oct 14 2025

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    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 WellStrong Fun Run, and a big expansion: partnering as the sole wellness provider at The Bridge Center in Barnstable County.
    If you think WellStrong is “just a gym,” this conversation shows the myriad of community services behind the doors—and why it works.

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    37 mins
  • Episode #22 - Startup Strategies for a Successful Small Business
    Sep 30 2025

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    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 owners. Whether you’re just getting started or already a year or two into your journey, you’ll hear practical, real-world insights to help you build a small business that lasts.

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    41 mins
  • Episode #21 - Chance Favors the Prepared - Small Business Edition
    Aug 19 2025

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    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 for the future. They share real stories from Cape Cod Gutter Monkeys and other businesses that hit roadblocks because they didn’t plan ahead—and those that broke through by thinking one step ahead.

    Whether you're in your garage or your growth phase, this episode shows why smart, strategic planning is one of the best investments you can make. Because chance favors the prepared.

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    42 mins
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