business
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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
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Contact path
Verified email
Booking probability
31%
Guest openness
Selective
Sign up to generate a grounded pitch for Monkey Business Radio.
Signup to Generate a PitchWelcome 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.
Recent episodes include "Island Pickle - Interview w/ Owner Bill Russell" (29 July 2026, 52 minutes), "Island Pickle - Interview w/ Owner Bill Russell" (29 July 2026, 52 minutes), and "Category Kings" (29 June 2026, 46 minutes).
Monkey Business Radio publishes roughly monthly, with episodes averaging 44 minutes across 29 episodes.
Booking probability for Monkey Business Radio is 31%, and the host is rated Selective on guests. Monkey Business Radio requires a Pod Score of 80 or higher. Monkey Business Radio's contact route on record: verified email.
The strongest fits for Monkey Business Radio are Business & Management Consulting. Monkey Business Radio has a business audience.
Monkey Business Radio is a business podcast with 29 episodes published.
Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.
Monkey Business Radio
<p>Send us Fan Mail</p><p><b>What happens when a chance conversation leads to one of Cape Cod's most unique new businesses?</b></p><p>In this episode of <b>Monkey Business Radio</b>, Chris Collins and Dennis "Bobby...
Monkey Business Radio
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...
Monkey Business Radio
<p>Send us Fan Mail</p><p>Every so often on <b>Monkey Business Radio</b>, we like to step back and talk about one of the fundamental principles behind building a successful business. In this episode, Chris Collins and...
Monkey Business Radio
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...
Episode #1
<p>Send us Fan Mail</p><p> 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...
Monkey Business Radio
<p>Send us Fan Mail</p><p>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...
Monkey Business Radio
<p>Send us Fan Mail</p><p>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...
Episode #23
<p>Send us Fan Mail</p><p>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 <b>Alicia Conlin</b> joins...
Episode #22
<p>Send us Fan Mail</p><p>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...
Episode #21
<p>Send us Fan Mail</p><p><b>Episode #21 – Chance Favors the Prepared: Small Business Edition</b></p><p>In this episode, Rusty Dripedge and Bobby Downspout explore how preparation drives real growth in small business...
Monkey Business Radio
<p>Send us Fan Mail</p><p>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...
Episode #19
<p>Send us Fan Mail</p><p>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.</p><p>In this episode, Chris and...
Episode #18
<p>Send us Fan Mail</p><p>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...
Episode #17
<p>Send us Fan Mail</p><p>Recessions, inflation, supply chain disruptions—every business faces storms sooner or later. The question is, are you ready for them?</p><p>In this episode, Dennis Siggins draws from more than...
Monkey Business Radio
<p>Send us Fan Mail</p><p>In this episode of Monkey Business Radio, we sit down with Scott Wellington—longtime customer turned proud owner of <b>Southeast Gutter Monkeys</b>, the newest franchise in the <b>American...
Monkey Business Radio
<p>Send us Fan Mail</p><p>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...
Monkey Business Radio
<p>Send us Fan Mail</p><p>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...
Monkey Business Radio
<p>Send us Fan Mail</p><p>What if the secret to market dominance isn't competing with others, but finding spaces they've completely overlooked?<br/><br/>"On the island of the blind, the one-eyed man will be king." This...
Monkey Business Radio
<p>Send us Fan Mail</p><p> 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...
Episode #9
<p>Send us Fan Mail</p><p>Most folks go where the puck is. Visionaries? They go where the puck is gonna be.</p><p>In this episode, we dig into what it really means to think ahead in business—and how that mindset can...
Recent guests on Monkey Business Radio. Study who booked and why before you pitch.
LKN Chamber President and host of Town Talk, Lake Norman Chamber of Commerce
Director of Campus Recreation & Fitness at SVSU, Friends of the Global Fight Against AIDS, Tuberculosis and Malaria
Executive Director, Authentic Conversion
Cape Cod Gutter Monkeys
PitchCentric classifies Monkey Business Radio under these industries. Guests from them are the closest fit, and each links to the best podcasts in that industry.
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